Joe Casabona

AI and The Emperor's New Clothes

2026-10-03T00:00:00Z

Perhaps you know the story of The Emperor's New Clothes. The quick version is these guys trick the Emperor into thinking they made him clothes that only smart people, or those fit for office, can see. So as to not look stupid (or unfit), he pretends to see the non-existent clothes and goes out in them.

Everyone else buys into this story too. To not look stupid, they pretend to see the clothes. It's not until a child points out, "he hasn't got anything on," that everyone realizes the farce. The crowd catches on...but the Emperor and his noblemen keep pretending. The moral of the story is people will go along with a lie to not appear stupid.

I've been thinking about this story a lot lately for something else that's been fashionable in certain circles: training AI to "sound like you" so it can write for you.

How AI Writing Is Supposed to Work

A person will feed everything they've written, or some voice notes, into their favorite AI tool. They will tell the AI to look at how they write, and the sorts of words they use and punctuation, and maybe even add some personal stories.

Then they can feed the AI a half-baked idea and tell the AI to write an article that "sounds like them." Some people might even have a separate skill in AI to check for AI slop¹.

The end result is they have a piece of writing that should be indistinguishable from their actual writing.

Does It Actually Work?

I can't say it never works; I haven't done the legwork to determine that. But my very strong suspicion is it only works in certain use cases. The main one being you're writing some step-by-step guide where the steps don't change very much. But even then, you can add prose...like a personal story or analogy...to the beginning to help people understand the guide.

Even if you're a bad writer, suddenly being a good writer doesn't sound like you. It will sound too polished and inauthentic.

Most of the time, especially if you're a gifted writer, people will be able to tell that you didn't write piece. It's the equivalent of whatever the dead-eyed look in AI-generated images is.

So why do people keep doing it?

No One Wants to Look Stupid

The Emperor's New Clothes ends with the Emperor saying, "This procession has got to go on." Either because he wants to keep believing that he's wearing clothes, or because he wants to keep up the facade that he is wearing clothes, he keeps going.

Most people who are using AI to write for them probably really want to believe that the writing sounds like them. It's such an incredible time saver to not have to write your own thoughts.

Some suspect it doesn't but believe eventually it will. And some probably don't care because they want to check a box.

But in any of these cases, there's likely also the fear that they'll look stupid. They don't want to admit that instead of just putting in the effort to write every day, they tried to take a shortcut and it didn't work.

Much like the Emperor, they feel, "this procession has got to go on." But it doesn't have to.

How to Use AI in Your Writing

I've written possibly ad nauseam about why using AI to write for you is bad, mmkay. I've also written about what you should think about anytime you use AI to replace a human being.

But if you want to use AI in your writing process, here are a few approaches:

Use It for Copy Editing

This isn't a foolproof plan, because AIs are not human and they don't think. They can't tell you if something will resonate with your audience. But they are word calculators and can tell you if what you wrote makes sense.

I will have it recommend specific changes, citing the line number. Then I will determine if the change is worth making.

Turn a Voice Note Into an Article

I've softened my stance on this over the last year, because this was also a "no" to me. You can't fully trust that what the AI will output is a 100% true representation of what you've stated...especially when it's interpreting what you've said from transcript only, not intonation.

But I also recognize that the blank cursor is my best friend, and seeing the words appear on screen is the best way for me to process my thoughts. This isn't the case for everyone, and if I'm going to keep toeing the line that writing is thinking, spending 20 minutes talking through something is most certainly thinking².

The important bit here is that you review its output and make sure it captured your points, in a way that you'd word it. I would say something like, add headlines and punctuation, but never reword anything I say. Use only the words I used in the order I used them.

Use It to Pull Thoughts Out of Long Transcripts

Something that I'll use it for isn't the writing part, but the ideation part. I'll have it look at podcast episodes I was on, coaching calls, or even regular calls, and pull subjects I can write about, along with summaries of the points I made.

This prevents what can be time consuming for people: figuring out what to write about. When speaking off the cuff, you probably say a lot of good stuff, but you're in the moment. That moment is gone when you go to write. This approach helps you.

Why This Is So Important to Me

Some people might be wondering why I care so much about this. On the surface level, it's about time. Why should I read what you couldn't even bother to write yourself? It's a completely selfish move on the part of the orchestrator of the piece.

It's also disingenuous. If they really didn't care if people knew AI wrote for them, the AI would get a co-author byline. But they know that will hurt their credibility.

But on a deeper level, I'm worried that since the advent of social media, we've been marching further and further away from the ability to critically think.

Getting opinions from people who have no business stating their opinion is one thing; taking it at face value because they don't care to fact-check it, or it's what they want to believe, is another.

And when we don't do our own writing, we're taking it one step further. We're signaling that we don't care to think about what we're putting into the world. Example: this article took me about an hour to write. But I was thinking about it for a couple of days.

We can look at eras throughout history and point to incredible, humanity-defining works. The Homeric epics. The Bible. The Declaration of Independence. Countless works of fiction.

I'm worried that one day, we'll look back at this era and realize we didn't create anything that transcends the current moment. That we won't have something that lasts 3 years, let alone 3000, 300, or even 30.

The real question is: will we realize that using AI to write for us hurts us, like the child who knew the Emperor wasn't wearing anything, or will we act like the Emperor in the name of trying not to look stupid?

Footnotes

Though...this should be unnecessary if you've properly trained it, right? ↩
Saying, "Claude, I want to write an article about AI writing and here's my hot take. Write it for me," is not. ↩

A New Engine for Casabona.org

2026-09-26T00:00:00Z

I got a harebrained idea after talking to my friend James Laws, who recently changed his entire website.

The idea is simple: I just want a nice place to write. With my WordPress site, I write in Obsidian, push it to WordPress, and then end up fighting the editor to make sure everything looks OK. When I want to make even simple changes, they feel hard.

I was a WordPress developer for years, and even small changes seemed arduous because of the technical debt I've accumulated¹.

I just want a nice place to write. So I decided to convert casabona.org to flat markdown files.

A Man with a Plan

The first thing I needed to do was come up with a plan. The site is 20+ years old and there are many links, images, and redirects to consider. I suspect things will break, but I really want to limit the breaking.

So my plan, with the goal being all of my essays/thought pieces living at casabona.org, was this:

Build the casabona.org flat files site, and make sure the URLs/permalinks exactly match the format from the casabona.org WordPress site.
Move any essays from the WordPress site to the flat files site.
Move essays on streamlinedsolopreneur.com to casabona.org and set up redirects.
Move a select number of pages (/now, /uses, /about) to the flat files site.
Move all important WordPress pages and forms to streamlinedsolopreneur.com.
Create a fully static version of the casabona.org WordPress site to live at archive.casabona.org.
Create a redirect engine for all old casabona.org pages, assets, and redirects.

Just writing that out sounds daunting. I love a good web development project, but since I'm no longer in web development, this was neither worth my time, nor worth hiring out.

The WordPress site was largely fine (random editing issues / tech debt aside). I just wanted a change. And I could make that change, thanks to Claude Code.

How I Used AI in This Site Migration

First, I did an analysis of my site traffic, using Claude's built-in browser and looking at both Ahrefs and Google Search Console / Google Analytics.

The AI surfaced a lot of good information, including old domains I didn't renew that now redirect to...undesirable... sites. So I reviewed everything there and came up with a general redirection plan.

Then I reviewed a list of all the essays on streamlinedsolopreneur.com myself, and created a list (or really, a date range) of what I wanted to move over.

Honestly, from there, I took those assets and handed them to Claude Code. It used a pre-existing open-source engine to do the markdown conversion, scraped the articles from the WordPress sites, and created a local site for me to test.

Then it created the static site from the current WordPress site (which would have taken days using leading WordPress plugins), and after testing locally, deployed both the main site and the archive to Netlify.

I also added search thanks to a library called Pagefind, which is super neat!

After reviewing the redirect plan one more time, and testing everything in the staging environment, I pointed the domains over to Netlify from my WordPress host, Pressable.

I uploaded the page and form exports from casabona.org to Claude, which pared them down to just what was needed. It also generated the redirect file for streamlinedsolopreneur.com.

Once I was satisfied with my test, and the AI's automated testing, I disabled the casabona.org WordPress site to make sure nothing new relied on it².

After a couple of days with no errors, I determined that I could delete the Pressable site.

This is the first article published with my new method.

How I Publish Articles Now

I've written exclusively in Obsidian for about a year now³. I want to keep doing that without wiring up GitHub into a folder in the vault.

So I also had Claude Code create a simple Obsidian plugin that allows me to write as I normally do, then push the markdown file (with the appropriate front matter for the markdown-to-html conversion engine) to GitHub.

I have Netlify automatically deploy from GitHub, so when I push the file, it gets published. No fighting the editor.

What's Left

The last couple of things I know I need to do:

Fully test the forms and pages that moved over to streamlinedsolopreneur.com.
Test publishing articles with and without images.
Update a page (like /now).

I'm also thinking about what credit usage on Netlify looks like. I've upgraded to the $9/mo plan for 1,000 credits and that should be more than sufficient. I was able to reduce my Pressable bill by 60%, saving over $400. But if updates and deploys are resource-intensive, I'll need to figure something out.

I really like the flat file model though.

I suspect there's still a bunch of testing I need to do, and probably some edge cases I haven't thought of.

What's Next

Something I did for the WordPress casabona.org was make a "feed" of my published work from around the web. This also allowed me to share links and photos, since I'm not on most social media anymore.

So aside from testing, I have another project in the back of my mind for my feed. It would live at feed.casabona.org and be an RSS aggregator, as well as allow me to post, Twitter-style. Maybe even add the Fediverse⁴.

It feels weird not having a WordPress-powered site after all these years. But it was a complicated and largely unnecessary system for what casabona.org is...which is now finally just a nice place to write.

I recognize this could also be the curse of knowledge. But I've also resorted to using Claude Code to make WordPress code changes lately (with my review, of course). ↩
This was a safe way to easily restore the site if things broke spectacularly. ↩
It's even usurped my beloved writing app, Ulysses. ↩
You know, if anyone actually figures out what it is. ↩

What is Conscientious AI Use?

2026-09-06T00:00:00Z

One of the most frustrating experiences for me as a parent is asking my kids why they did something and them responding, “I don’t know.” There are a number of reasons they might say it.

Maybe they think they’ll get in trouble if they tell me why they did it. Maybe they did it to protect a sibling from getting in trouble. Maybe they don’t think, “because I wanted to,” is a good enough reason.

But it’s mostly because kids have no impulse control. There’s very little friction to go from “I should do this” and actually doing it. And there’s even less thinking.

Over the last couple of years, I’ve noticed this same trend with using AI. AI apps are getting more powerful, easier to use, and literally everywhere¹. There’s no friction to use them. And there’s potentially even less thinking.

Why We Use LLMs Too Much

About a year ago, my wife provided me with two examples of AI use: one was super good, and one was not.

The super good use was designing my birthday cake. She described what she wanted, and then gave the design to an incredible local baker to actually make. She had an idea, but couldn’t execute it in a way that would clearly communicate to the baker what she wanted.

The not so good one was using it to come up with a scavenger hunt for our kids at the local trail. When she told me, I responded (bluntly), “You couldn’t come up with 10 things for them to find?”

Now look — I get that she’s busy and we had a lot to do that morning and it was going to be a fun activity for our kids. It was, as you could imagine, a pretty good list. But that’s not the point. The point is that she didn’t even think about not using it. It was easy and it was a task it could do.

I fell into this trap a few months before that; I was talking to it on my phone, asking it questions instead of thinking about them myself. But instead of creating a benign game for my kids, I ended up taking my business in the wrong direction.

I, like so many other people past and present, was taking the easy way out; but I was also tolerating substandard work. Luckily, I realized before it was too late.

When we’re not conscientious about how we’re using AI, we risk using it for important stuff (like critical thinking, articulating opinions, or work that requires taste and judgment). And then everything we do becomes substandard.

So how do we make sure we’re thinking about our AI use?

What is Conscientious AI Use?

The shortest possible answer to this question is this: You don’t blindly use AI to do stuff. And the goal of using AI should go far beyond, “I don’t have to do it anymore.”

But it’s a little bit deeper than that. Earlier this year I was having a conversation with a friend about how it seems people are getting “AI-Brained.” They struggled to function without using AI to help them.

This led me to write 4 warning signs you’ve got AI Brain Rot, and I think it’s one of my most important blog posts to date. I would strongly recommend you read the whole thing, but the 4 signs are:

You use AI reflexively without thinking through a problem yourself first.
You skip talking to people and instead ask AI questions humans should be answering.
You have no skin in the game because you’re just blindly asking AI to do things.
You treat AI as an advisor or coach.

In that article I go on to explain why these are very bad paths to go down, and how you can prevent AI Brain Rot. I even built a quiz to help you figure out which area you are highest risk for². But something missing from that article is the other side: a set of principles for using AI conscientiously³.

How to Use AI Conscientiously

There are 3 rules for using AI conscientiously:

#1: AI is for tasks, not craft. I will die on this hill. If you’re using AI to wholly create something for you, you are not using it conscientiously. And I’d argue it’s not really yours.

There is a nuanced difference in using it to assist you in creating something. But it’s not the same as something like Photoshop because Photoshop will not try to predict what you want it to do.

Instead, we should use it to take repetitive tasks off of our plate, or do things that have clear and verifiable outcomes. Some examples are:

Move tasks from our inbox to our task app
Do verifiable research on a topic (as in, cite sources that we can then check)
Write scripts to connect to other services (the scripts don’t change when the models change).

#2: AI cannot replace judgment. Asking it for “advice” and seeing what it comes up with betrays conscientious use because it means we’ve forgotten that it’s not actually judging anything — it’s just giving you a statistically likely answer.

As the models get more impressive, it’s easy to think that has shifted, but it has not. It will make a calculation that the answer it’s spitting back at you “looks” like some advice a human would give; but if you’re asking it judgment questions, it’s probably not. Just ask the hikers who had to be rescued after using AI to plan their hike.

#3: There should always be a goal for AI use beyond “I don’t have to do it anymore”. This is really the core tenet of Conscientious AI Use. I put it 3rd on the list because we need to remember 1 and 2 before we even get here.

But once we do, we can keep in mind the best uses for AI and then determine, based on our goals, if we should use AI for the task. I have more here, but I developed a 3-question test for this exact purpose:

Does this task actually need to be performed? If it doesn’t, then neither you, nor AI, should do it.
If it needs to be performed, ask, “what is the goal of the task?” Without knowing the goal, you cannot possibly know if AI is actually helping you with it.
Then finally, “how can I measure if and how AI is helping me with this task?”

Understanding that AI is for tasks, not craft, that it doesn’t have any ability for judgment, and that we should have a clear reason for using AI combines to create Conscientious AI Use.

Who is Conscientious AI Use For?

I’d love to say Conscientious AI Use is for everyone. I firmly believe it should be for everyone.

But the truth is if you think AI is the end-all-be-all, that you have a “team” of “agents” “doing” your work for you, that you refer to AI as people and that it is your employee, I’m not going to convince you otherwise.

I refer to this as being AI Blue Pilled, and if people want to keep believing that AI is capable of thinking for them, I’m not going to change their hearts and minds until they choose to unplug from the proverbial Matrix⁴.

But, if you’ve gotten this far, I suspect you are not AI Blue Pilled. If you know AI can help you (because it can), you’re just not sure, you’re in the right place.

If you’re worried about becoming overreliant on AI to the point where you’re not thinking for yourself, this is for you.

This will serve as your guide for thinking about how you use AI, and what you use it for.

That way, when someone asks you why you used AI for the task, or if using AI actually helps you accomplish your goal, you’ll have a better answer than, “I don’t know.”

Seriously. I don’t need an AI coach in my CGM app telling me why I saw a blood sugar spike after I ate ice cream, Stelo. ↩
Mine is “no skin in the game” ↩
At this point, I should give credit to my friend Jen and my mastermind group, who coined the term “Conscientious AI Use” for me. ↩
Though I guess in this case, the scenario is slightly closer than we’ve ever been to the actual Matrix. ↩

Automation vs. AI: Which One Should You Actually Use?

2026-08-24T00:00:00Z

Something my brother Phil and I would do before I had kids was travel to go to concerts. We’d go with a couple of friends, grab a hotel room, and enjoy the show.

One time after check-in and before the show, we decided to grab some food. And since we were college students with limited funds, we got a box of Pop Tarts. And since the hotel didn’t have a toaster, I used the microwave.

I’m not sure if you know this, but the instructions say to microwave a Pop Tart for 3 seconds. I set it for 2 minutes. That was a mistake.

As you can imagine, the Pop Tart was burned to a crisp and the smoke alarm went off. All because instead of reading the instructions or using a more appropriate tool, I used something too powerful.

I’m noticing this trend with automation and AI; people are starting to use the terms interchangeably. But they are different, and using AI for a simple process automation is kind of like microwaving a Pop Tart.

What’s The Difference Between Automation vs. AI?

From a purely “common use case” standpoint, automations make things happen based on some inciting incident, called a trigger. An example I use commonly is, If it’s sunset in December, turn on the Christmas lights. Sunset is the trigger. Turning on the Christmas lights is the action. There’s a “condition” to only do it in December. This is very predictable. You can look at the month and know if and when the Christmas lights will turn on.

AI has largely been used as a program you can “chat” with to find information, process data, or do other things you probably shouldn’t use it for.

What makes this confusing is that LLMs can be used for automation, and are increasingly being used as such thanks to tools like Claude Cowork. So to really differentiate between the two, I want to borrow a term I learned from Emily Mabie over on LinkedIn.

Traditional, pre-ChatGPT era automations (think Zapier, Make.com) are Deterministic Automation. You know the input and the output, and the process runs exactly the same every time.

I’m referring to automation via LLMs/AI (or AI “agents”) as Interpretive Automation¹. The scope of the task is broader, and the automation is run by an interpretive algorithm, which means that the output may change slightly (or dramatically) each time.

So the difference between Automation vs. AI in this context is that Automation is “Deterministic.” AI is “Interpretive.”

When You Should Use Deterministic vs. Interpretive Automation

Now that you know the difference, when should you use one over the other? Here’s a simple test.

The 4 components of deterministic automation are triggers, actions, conditions, and timing. Think about these when you’re considering which to use. Then ask yourself these questions:

Does this always have the same input (trigger)?
Does it always have the same result (actions)?
Is there little to no decision-making when it comes to the input and output (conditions)?
Do I need it to run consistently (timing)?

If the answers to all of these are yes, you need deterministic automation. On the other hand, if the input, output, or decision-making are not straight-forward, interpretive automation is the way to go.

In my opinion, most business automations would be better served by deterministic automation.

Why Deterministic Automations Are Better for Solopreneurs (and Most Businesses)

Automations are best when they are predictable and reliable. By definition, interpretive automations are not that, as the AI might change how the algorithm interprets an instruction.

With deterministic automation, when the trigger happens, the actions happen every time — and predictably. When a deterministic automation tool does fail, it does so “loudly”…that is, it will tell you when it errors because it’s very clear on what an error is. You’ll usually get an email, and then if it fails enough, the automation will turn off and you’ll get an email about that too.

Now, something that AI can do is sometimes verify the results by “looking” at them. This is helpful, but also not consistent (and unnecessary if you know what the results will be).

A couple of other drawbacks of interpretive automation are that errors may not be surfaced at all…especially errors with the results. AI is sycophantic, which means that it will agree with you for each individual pushback. That feedback may not impact the next run though.

Those probably can be fixed with better instructions (“fail loudly,” “don’t just agree with me, verify the end state”). But there’s one drawback that none of us can do anything about.

Interpretive Automations Can Change with the Model

When the LLM model changes — and therefore the engine running the automation — the automation can also change. We’ve seen this a bunch of times over the past year especially. We even have leadership at Claude recommending resetting your LLM’s memory with every model upgrade.

I experienced this with a few skills in Claude, where the model changed and the results of the skills changed…which means I had to change the skill.

If you’re doing something your business relies on, you should ask yourself: “if this breaks suddenly, how much time am I willing to invest in fixing it?”

Conversely, deterministic automation tools are very reliably backwards compatible. When something changes, those changes are communicated well ahead of time, and when the change is made, things don’t break immediately.

That’s the kind of reliability you should have with your business automations.

Examples of Deterministic Automation vs. Interpretive Automation

I’ve already mentioned the Christmas lights example as a good deterministic automation. What about some related to your solo business? Here are a few that are perfect for deterministic automation:

When I add a new contact in Notion (trigger), send a new task to Todoist (action)
When someone books a clarity call with me (trigger), tag them in Kit.com (action)
When I update a status in Notion (trigger), send an email to my VA (action)

All of these are straightforward, predictable, and happen the same every time.

Now a couple of interpretive automations:

Scan my email inbox for tasks. This one is interpretive because there’s no clear trigger; I get emails throughout the day. There’s also no obvious way to find tasks. It takes the interpretation of an LLM to determine what is or is not a task.

Review and score emails I sent to my mailing list over the past week. This pulls emails over a rolling timeframe and applies a score based on several factors (opens, clicks, unsubscribes). Could I do this with deterministic automation? Possibly…but it would heavily depend on what Kit.com (my ESP) exposes to Zapier.

Create assets and upload any new podcast episodes to RSS.com. This one looks at the status of episodes in Notion. If they’re marked “Ready for Publish,” the LLM grabs the transcript, creates a basic description and gathers show notes, then uploads everything to RSS.com.

This one technically could be done with deterministic automation. In fact, there’s a very clear trigger (status change), condition (status is “Ready for Publish”) and end state (episode is uploaded). However, there are a lot of factors in making it run smoothly:

I need to essentially write code to work with the RSS.com API.
I need to host the videos somewhere Zapier can access and then upload.
I still need to call some LLM to process the transcript.
I need to give a lot of context to the LLM and/or Zapier.

In this instance, creating an interpretive automation on my computer that can access all the files was better. It also used Claude Code to write a script to talk to the RSS.com API. That script will not change, so the main mechanism for the end state is still intact, even if models change.

It’s All About Conscientious AI Use

The main takeaway here isn’t that you should only use one or the other. It’s that you should be conscientious about which you choose. Are you just blindly giving things to an LLM because it’s easier? Because you haven’t thought about it?

Or because you don’t know much about deterministic automation tools like Zapier?

Interpretive Automation and AI can be great for a lot of things, but you need to do what will be most reliable for your business…especially if you’re a solo business owner.

Footnotes

I have not seen this term used, but trust I’m not the first person to use this framing. ↩

What Abigail Adams Showed Me About Shallow Thoughts in the Age of AI

2026-08-17T00:00:00Z

The publication In Pursuit is doing a fantastic series on all of the presidents and the women behind them for America’s 250th anniversary, and I’ve finally been able to catch up on them.

The article about Abigail Adams by Joseph J. Ellis taught me a lot about her, but it’s something in the opening paragraph that struck me the hardest (emphasis mine):

There were no cellphones, no internet, no instant forms of communication. There were, however, letters, which often took weeks or months to arrive. The act of writing a letter was therefore a more deliberative process than composing an email, more like writing a speech than having a chat, more a projection of your deepest thoughts than your immediate impulses.

Abigail and John Adams both bought journals in which to write and keep their letters to each other. They knew given John’s position that those letters might be of some interest.

I’ve been thinking about this sort of idea a lot during my Year of Digital Detox — but really just the instant, constant connection. Not the deliberate part.

Ellis is obviously correct: since 1776, communication and writing have gotten far less deliberate. And it’s negatively impacting our ability to think.

AI is Making This Worse

Where loads of thought would go into letters, today, with AI, more words are being written with the least amount of thought possible. I’ve adopted the saying, "writing is thinking," and this is just another argument for it.

More people are talking about how they’ve trained Claude to sound "just like them"¹, and how they can just fire off an idea and the "agent" can just write an article and publish it for them.

There are also websites like Outrank that basically remove you from the process completely. You tell it some keywords, and it will write and publish articles for you so you can be found online.

The people who use this are putting their name on something they’ve literally put no thought into. It’s like saying you should get credit for The Odyssey because you had the idea to make it into a movie.

That’s not really even my point though. My point is that, while slop is a side-effect of the "AI writes for me" revolution, the real danger is we’re no longer thinking about problems. We’re putting effort into getting noticed for solutions we haven’t considered further than just a prompt.

The good news is that while more people are doing this, it will be easier for you to stand out.

How to Stand Out

The Yankees² just called up George Lombard Jr., a 21-year-old kid, to be our starting shortstop. And so far, the fanbase has been quite taken by him.

Yes, he definitely has the skills. In 11 games, he’s demonstrated baseball IQ that seems increasingly rare in the sport. But he’s only 11 games in. So why is he standing out so much?

Because compared to the parade of errors and issues we’ve seen from our shortstops for several years now, he looks like an absolute veteran player.

I think the same is true of writing; when most of the writing is shoddy, shallow thoughts fired off quickly (or prompted), the good writing will stand out.

To me, thoughtfulness will be a true differentiator in the coming years. With the world’s information at our fingertips, and any answer + explanation readily available, the smartest will not be the people with the most information, but the most thoughtful.

It’s incredible that we have so much more power than any other time in human history, and the majority of users pursue it to think less, not more. To say more without really saying anything.

After all, to quote Qui-Gon Jinn, "The ability to speak does not make you intelligent."³

We need to be more like Abigail and John Adams. Think deeply about a topic and write it down. Don’t outsource your thoughts to a machine.

AI writing is already starting to get old; imagine how it’s going to look in 250 years.

Spoiler: it doesn’t, no matter how much they wish it were true. ↩
Yes, dear reader. It’s another baseball analogy. ↩
A Star Wars reference too?! I’m on fire! ↩

Not Sure Where to Start? The 4 Systems Every Solopreneur Needs

2026-08-12T00:00:00Z

I remember the first time I went to see my accountant. I was around 19 or 20, and figured it was time for me to treat my side hustle of building websites as an actual business.

I had been reading books on how to start a business, and one talked about the Shoebox Method for accounting: just shoving all of your receipts into a shoebox for your accountant to sort out later.

That sounds like madness, but I thought I’d play a little joke on my accountant (a family friend) and tell him that’s what I was doing. I’ll never forget the look on his face — wide eyes, mouth agape, cold sweat forming on his brow — before I told him I was just kidding and had a spreadsheet, to go with a folder of the receipts in my bedroom (slash office).

Even back then — over 20 years ago — I knew the importance of having some system. I was a pretty sloppy kid, but in my business and school work, I was very organized.

I knew I had to be if I was going to be good at anything.

Years later, before I got connected with my now long-time accountant, Rachel, I actually met with someone local who told me my accounting system was so good that he didn’t think I needed him. My strong suspicion is that he didn’t want to do small business accounting, but it was still a nice compliment.

To be honest with you, I didn’t think I was doing anything special. Surely everyone thought in this way, right? How can they spend the least amount of time creating something great?

But last year I did a series of customer calls that made it very clear this was not a common trait.

“I Don’t Know Where to Start”

Throughout these calls, I got perhaps the most important feedback I’ve gotten since moving away from web development:

I read all your stuff and I’m always like, this sounds awesome, but I don’t even know where to start or how to ask.

And it came up more than once. So today I want to show you where to start. I’ll walk you through 4 systems every solopreneur should have:

Admin Work
CRM (and Client Experience)
Content
Idea Generation and Capture

Let’s start with Admin Work.

System #1: Admin Work

This is first because it can potentially have the biggest impact. You should have a system for capturing your daily work:

Calendar events
Notes
Tasks
Actionable Items from meeting notes

Luckily there are default apps for pretty much all of these — but a system isn’t just a bunch of tools. It’s making them work together. Specifically:

How can you protect the time on your calendar so you can do your best work?
How are you capturing tasks into a task manager you actually use?
Are you able to quickly capture notes and put them someplace where they don’t get lost to history?
How are you getting your most important action items from meetings while still being fully present?

The reason so many different tools exist is that this is a very personal process. For example, I gladly pay for Fantastical every year because it handles large numbers of calendars the best, and I have 20+ calendars across my personal and work life.

When I do my weekly budgeting, I can hide all calendars except my Bills calendars (as the name suggests, what day each bill is due, and how much it is). During work hours, I only see the calendars that impact my work day. Outside of work, I only see personal/family/school calendars.

The same thing goes for tasks and notes. I love Obsidian for notes because it’s so versatile. But I have friends who feel (like I once did) that it’s too complicated. They use the default notes app on their phone because that’s what they know they’ll actually use.

As you build this system, it’s important to know the answer to this question:

When do you work best? Optimize for doing your best, most focused work at these times.

One great way to figure this out is through something called task journaling. You set out to perform 3 tasks in a day, and check in with yourself throughout the day to see when you’re feeling most vs. least productive.

When it comes to info gathering and review:

What will help surface the information you need when you need it?
What will help you capture information quickly so you don’t forget it?
What will help simplify, not overcomplicate, your process?

Your Foundational System

The reason we covered this one first is because it’s foundational. You should use your task manager for all tasks, not just specific ones. You should keep all of your notes in your notes app. And a good system for email and calendar management will affect all the work you do.

One way to keep your admin systems on track is to have a weekly planning session, where you review tasks, appointments, and notes.

Every other system can build on what you have for admin work. A really good example is the CRM System.

System #2: CRM

CRM stands for Customer Relationship Management, and most simply, it’s a way to capture, nurture, and convert leads into customers/clients. While entire industries and enterprises are based on this niche, your CRM does not need to be a complicated system.

I always recommend starting with something simple so you actually use it. Big honkin’ CRMs can be super overwhelming and require a lot of access to other accounts right off the bat. This is exactly what prevented me from actually implementing a CRM in my business for a long time — until I built something basic in Notion. You can use Trello, Notion, Google Sheets, or whatever works best for you. If you do want a complete, soup-to-nuts solution, HubSpot is free to start, which makes onboarding pretty painless.

The idea here is you want a way to track people who could potentially buy from you, or have bought from you. I use my CRM to keep everything from contact history to personal notes, and videos I’ve sent them.

This ensures that you’re building relationships, but also that you’re following up and showing people you’re the solution they need, when they’re ready for it.

Don’t underestimate the act of following up.

In 2025, I added $20,000 to Q4 simply by following up with leads from earlier that year. Most people won’t “just reach out” when they need you. Most need a nudge from time to time.

A few simple requirements:

People should be able to fill out a form and automatically get sent to your CRM.
Have a way to set reminders about follow-ups so you don’t forget.
Track status — this will allow you to see how effective your outreach and sales calls are.
Make it something you’ll actually use!

Start simple at first. If a Google Sheet is where you’re comfortable, then do that. You can always upgrade later. Especially since Sheets exports to csv, which is a near-universal format for table data.

Let’s talk about forms

The way I see it, in this context there are 3 kinds of forms:

Call scheduler. These are your warmest leads, and people who have a very real chance of giving you money. These will allow you to send the call booking info to your CRM so you can track tangible calls.
Mailing list opt-ins. A way for people to join your mailing list, giving you a way to nurture them and get them to book with or buy from you when they’re ready.
Lead capture forms. This allows people to raise their hand and say they want to work with you.

Depending on the CRM you choose, many of these forms can be built-in or easily automated with Zapier.

You can get more recommendations and the entire Solopreneur Systems Starter Kit here.

Client Onboarding/Experience

Something I considered adding to this was a “Client Experience” system, but after careful consideration, I determined that each niche, and each solopreneur, likely has a fairly personal approach to client onboarding. However, there are some things you should consider as you build yours out:

First, what’s something you’ll actually use?
How is the system communicated to the client? In other words, what are you doing to manage expectations?
How much technical knowhow and support will they need to use your system?
Are you trying to be clever when clear will do?
What actually serves your clients best and how can you balance that with what works best for you?

System #3: Content Creation

If you’re a solopreneur, you’re likely creating some sort of content: videos, podcast, articles, newsletter, etc. Having a good system in place for this is important to be consistent without feeling overwhelmed.

Much like with Client Experience, each solopreneur’s content creation process looks different. That’s why Standard Operating Procedures (or SOPs), good tools, and process automation are really important here. Think about:

How you capture ideas (more on that in the next system)
What the idea approval process looks like
How you’re tracking the status of multiple pieces of content
What tools you use to create the content
How the content is getting edited and reviewed
How and when it’s getting published
What goes into publishing it
How you’re promoting it
The ultimate goal of the content

I want to address that last point first because it will dictate how often you publish and on what platforms. It should also determine your CTA — and how people who follow that CTA get into your CRM.

My goal is always to get people on my mailing list…maybe you could tell because there are multiple CTAs in this article. If your goal is growth, maybe asking for likes, subscribes, and comments on YouTube is more important.

The Publishing Process

Having a system that allows you to look at your content schedule, review everything, and then record is really important for you to batch content. Otherwise, you’re just running around every week going, “What am I going to talk about? How am I going to talk about it?” And that increases the length of the content creation process.

I recommend setting aside one day every week to create the content. My dedicated recording day is Monday. I have no meetings, and the kids are out of the house (even in the summer) so I know it will be quiet.

Once you know your schedule, you should consider the tools you are using to create the content. What works best for you? Is it your iPhone? Do you prefer yapping?

And how is that content getting edited and reviewed? In my system, editing is really easy because I do a lot of stuff on the front end to make sure I don’t have to edit on the back end.

I recommend creating a Standard Operating Procedure (SOP) for this.

Creating Your Content SOP

Since this process can be so different per person, it would be a good exercise for you to figure out your own by creating your SOP. There are likely several stages of the process, so what I recommend is for each stage, record a video of you performing the work, and narrate what you’re doing. You can use an app like Tella or Loom.

For each video (or SOP), you should go through 4 things:

What is the purpose of the task?
What are the inputs? As in, what data do you need to perform the task? What does this look like at the beginning?
What are the steps you need to take to perform the task?
What is the output? As in, what is the end state, after you’ve performed the task.

Once you do this for the task, take the video, transcribe it, throw the transcript into Claude or your favorite LLM, and ask it to write out the steps. Then review it for accuracy.

After that — congrats! You have your first SOP.

Repurposing Content

I want to talk about repurposing for a second, because it seems like a slam-dunk way to get more mileage out of your content, and it can be. But we need to remember one important rule: make content for the people on the platform.

As much as LinkedIn wanted video to work, people on LinkedIn didn’t want video. So repurposing long-form video into short-form on LinkedIn (or even cross-posting from TikTok to LinkedIn) is probably a waste of time.

I like to repurpose ideas, not necessarily the content. So if I have an idea, say, about how to create a planner in Notion for your content creation system, I’ll write the tutorial. I’ll record the video using the tutorial as an outline but not necessarily a script. I’ll use the headlines in the tutorial for the broad strokes of a short-form video. I’ll take the main beats and turn it into a LinkedIn post.

This is far better than recording the video, and having AI generate the tutorial, and having AI clip parts of the video out of context to post. Each piece of content should be able to stand on its own.

On AI

I’ve basically written a treatise on using AI in creative work. The line is going to be different for everyone, but I firmly believe AI shouldn’t touch any of my content until post-production. Systems help us stay consistent, not a word robot creating vanilla cake that we add some icing to.

My entire Solopreneur Systems Starter Kit has a comprehensive section on content creation, where I also suggest systems for writing, podcasting, and video production.

System #4: Idea Generation and Capture

For our 4th and final system every solopreneur should have, I want to talk about idea generation and capture. We all have ideas, after all.

Now, you might be wondering why I didn’t include this in either Admin work or Content Creation. Notes, tasks, content ideas. Seems like it would slot in nicely in either of those systems…or both. And that’s the real reason it’s its own system. Ideas can go into admin work, content creation, or CRMs.

Maybe you think of a solution for a client, or a type of client to reach out to. Maybe it’s a follow-up idea. I would say these belong in your CRM, not as part of admin work or content creation.

Second, not every idea should be clogging up the work that you’ve fully vetted as work you should be doing. A lot of ideas solopreneurs have throughout the day are either things that should be back-burnered or thrown out. As my friend Alex Sanfilippo says, we need to “keep the main thing the main thing.”

But that doesn’t mean those ideas should be lost in the void. I mean…they need a chance, right?

The most important part of this system is the ability to capture ideas quickly and conveniently. Most people think, “if the idea is good enough, it will come back to me.” That is demonstrably not true (for most people). I operate under the assumption that if I don’t capture it now, it’s gone forever. As I was writing this, Seth Meyers said this exact thing on The Lonely Island and Seth Meyers Podcast:

For any young person who is a writer, I cannot tell you the value of what Andy did there. Anytime you have dumb ideas that you’re like, well, I won’t forget these. They’re too dumb. Writing it down, emailing it to yourself, having a rolling just notes app on your phone for the dumbest ideas.

…The amount that I go to bed being like, oh, that’s…good, but I’m so tired I’m not going to write it down now. And then you wake up and you’re like, well, gone forever.

So what do you need for a good idea capture system? First, it’s worth thinking about these questions:

What devices do you use (and usually have on you)?
What apps do you use to take notes?
What apps are you using with other systems we’ve outlined here?
Do you prefer to write, type, or talk ideas?
How do you evaluate ideas?

As with any of these systems, it’s only good if you use it. For example, a crucial part of my system is being able to capture ideas hands-free. Often I’m driving, managing kids, or walking the dog and don’t always have a free hand. I know I can shout to Siri. If Siri fails, I can also push the action button on my Apple Watch, which will activate Whisper Memos.

You can see me walk through my entire voice capture system here:

My general recommendation is to have 1-2 clear ways to capture ideas, and make sure they always go to the same place, that way they’re easier to review.

Using Your Systems

When I bought my first expensive fountain pen, a friend of mine asked if I was going to use it, and if I was going to leave the house with it.

It seemed like a ridiculous question. “Of course I am. It would have been pointless for me to spend all this money on a pen just to look at it.”

The same thing goes with your systems. You can build a fancy, super complicated one based on someone else’s template…but if you’re not going to use it, all you’ve done is waste time and money.

I obviously have strong opinions about how my systems work, and I wanted to share with you how I save 14+ hours per week, and how I run a solo business without things like client follow-ups falling through the cracks.

I also know this can be overwhelming, and my systems weren’t built in a day. They evolved over time, and are still evolving today. That’s why I wanted to include the simplest viable version of these systems — to give you a starting point.

My recommendation is to pick one system — the one that feels the most urgent — and implement the simplest version. See how it feels, then tweak it to make it something you’d actually use.

If you’re not sure which system to start with, I created a simple, 60-second quiz to help you figure it out.

Fill it out, and I’ll tell you where to start, and exactly how to get started…plus you’ll get the full version of the Solopreneur Systems Starter Kit.

Start Here Before You Build: Simple Solopreneur Systems That Actually Work

2026-07-06T00:00:00Z

I found myself in a rare position yesterday morning: I didn’t know what I was going to write about for this newsletter. The best I had was a vague idea about the point I wanted to make.

Then my youngest daughter, Abby, asked me a very pointed question: “Daddy, is that girl really on fire?”

We were listening to Girl on Fire by Alicia Keys; if you’re unfamiliar, the refrain includes the statement “this girl is on fire” 9 times.

When I said no, Abby said, “why does she keep saying it then?” I explained that being on fire could mean being very passionate about something. She then asked me what “passionate” meant.

“Caring a whole lot.”

She forced me to take this statement and put it in the simplest terms possible. This is something I’ve been thinking about a lot.

It can be easy to get sucked into the big complicated setups that some solopreneurs (including myself) have. The massive, multistep Zaps, the “team” of Agentic AI Agents™ doing your work so you don’t have to, quality be damned.

But before you do something fully automated and complicated, two things need to happen:

You need to understand the simplest form of the problem.
You need to know the building blocks.

My 4-year-old didn’t know “this girl is on fire” could mean anything besides the most literal meaning. So I first had to explain metaphors: what was literally being said meant something different.

Then I used a word she didn’t know: passionate. So I had to explain the metaphor using simpler terms. That’s when she understood…the girl that was on fire cared a whole lot about something¹.

You can do the same thing in your business. Before going off and creating a complicated process, system, or automation, break down the building blocks:

What are you doing?
Why are you doing it?
What information do you need?
What is each step in the process?
What parts require your unique skills?
What parts are predictable and routine?

Once you have these answers, you can start building the system. Start with creating a central place to keep track of the process: the steps, the statuses, the information you need, all in one place.

Then you can start building automations, or yes, even AI skills, to help you do the work.

I feel like I got a little lucky yesterday. Girl on Fire happened to be playing, for the umpteenth time that week. My daughter happened to ask me that question as I was thinking about my newsletter. It was a nice bit of inspiration exactly when I needed it.

But…I fully admit that if I didn’t know what point I wanted to make, you wouldn’t have read that story. Even when I don’t have the full picture, my system helps me understand my overall goal. That makes it easier to find the inspiration.

Now, if you read this thinking, “that sounds great Joe, but I’m still unclear on where to start,” I can help. Use the form below to join my mailing list, and get the Solopreneur Systems Starter Kit — 4 systems every solopreneur needs to get started, and exactly where to start.

I later learned that in this particular song, it was more about the empowerment of being free from a world falling apart around her. ↩

Why Repurposing Is the Solopreneur’s Smartest Content Move

2026-06-29T00:00:00Z

Over the weekend, I saw Toy Story 5, which I highly recommend. You will probably cry.

While sitting through the obnoxious amount of ads and previews (about 30 minutes’ worth and enough that all three of my kids asked, “when will the movie start?”), I noticed something about the movies. Many of them were covering a lot of similar themes:

Going to a faraway land
Keeping your memories
Remembering childlike play
Feeling nostalgia

Further, I was able to see the threads of other movies in these new ones. Similar stories, new audiences.

We’re seeing the same thing with what are largely believed to be the two summer blockbusters: The Odyssey and Spider-Man: Brand New Day. Characters and stories that have been repurposed for a new medium, audience, and generation. Brand New Day is loosely based on the comic story arc from nearly 20 years ago.

Last week I mentioned how you can effectively repurpose. But what I didn’t mention was that repurposing can also be iteration.

Repurposing the Same Idea

You have a kernel of an idea, and you can repurpose it for different audiences, using different analogies, or just rephrasing it slightly to make it land better.

That’s what all of the movies above have done. That’s what West Side Story did with Romeo and Juliet. That’s what O did with Othello. And that’s what you can do too.

Here’s an example: I’ve been preaching the idea that “faster isn’t better, it’s just faster.” The argument for a lot of people using AI for things they shouldn’t use AI for is just that: “Well, it lets me do it faster.”

I’ve repurposed this idea several times across my newsletter, blog, talks, podcast, and social channels. I’ve changed the delivery slightly each time, finding new analogies or ways to make my point land, including:

Talking about rushing a throw in baseball (trying to make the play faster than you need to) leads to more errors, not fewer.
Cooking an egg as fast as possible doesn’t lead to a better-tasting egg. It leads to a burnt egg.
One I just thought of right now: would you rather have sushi from a sushi restaurant or a fast-food place?
My favorite one: you can skydive without a parachute to do it faster. But you won’t find anyone who said when they did it, it was better.

The point is this: reinventing the wheel every time you create content is time-consuming. I think it’s necessary to come up with new ideas and new content, but every piece of content you create shouldn’t be new.

I just spent weeks writing a near 10,000-word resource for solopreneurs. You better believe that’s getting repurposed. It’s probably going to power 90% of my content this summer.

Newsletters that turns into lots of different content

These articles (which start as my newsletter) usually get turned into podcast episodes and LinkedIn posts. They also serve as inspiration for YouTube videos. But in each instance, I’m also iterating on the idea. Reading this newsletter verbatim wouldn’t make a good podcast episode. It would make an even worse YouTube video.

So I need to repurpose, but I also need to mold it for the medium and the audience. Just like someone reading The Odyssey on screen wouldn’t be a summer blockbuster. It would likely be unwatchable.

Can you Repurpose More?

As we approach July, I want to borrow an idea from my friend Austin. Think about the content you’re creating for the month or the next few months; how much of that is new? Can you make even 10% of it repurposed?

And if you need help, I’m cooking something up — a system that will make it so you’re only spending 2 hours per week on your content. Interested?

Join my mailing list below to get notified!

A Simpler Content System for Busy Solopreneurs

2026-06-22T00:00:00Z

Last week the parish carnival was in town. It’s one of my kids’ favorite summer events so we got the weekly pass, which ended up saving us $120 (seriously, we were there like 60% of the time it was open).

At several points, my kids all wanted to do something different, and since the carnival was confined within church and school property, where I knew a decent percentage of the community, I felt comfortable letting them do their own thing within reason. My oldest was the only one completely out of sight, and she knew where I would be.

I posted up in a spot where I could see the other two, and where I knew to look for my oldest. As time passed, keeping an eye on each of my littles, scanning for my oldest, and trying to maintain conversations, I started to feel overwhelmed.

I guess I should mention at this point that my wife was working three of the four days, so I was mostly flying solo.

This seemed like the best method for me…until the last day. That day, I switched to a different approach: my oldest could still go off on her own if she wanted, but instead of constantly scanning for her, we had regular check-ins at designated spots. I also had some friends keeping an eye out for her. My littles did adjacent attractions. And I made sure we spent more time all together thanks to food. Even though we were there the longest, I felt the least overwhelmed because I wasn’t doing too much.

I decided to put a better system in, and do less. I recently started doing the same thing with my content — and because I know how hard it is to get ahead with content as a solopreneur, I’ll share how you can too.

Paper & Smoke May Go Up in Smoke

One project I was really excited about at the beginning of the year was the companion publication to my yearly theme, The Year of Digital Detox. I figured I would have a podcast and a blog/newsletter, where I would talk about several things:

My experience trying to rely on tech less
Doing more things in the analog world

As with any project one’s excited about, I started off strong. But after a while, I started publishing less and less. I didn’t find a good groove, and the amount of time I was putting into the articles was disproportionate to the work I should have been doing. The podcast fell off much faster because I was thinking of just doing spoken versions of the articles, but I couldn’t get over how Substack handles podcasts vs. articles.

Another part of it is I’m not playing the “Substack” game. I left most social media to avoid having to play the algorithm and engagement game, and Substack seems to have added that in…and I hate it.

But ultimately, it’s because Paper & Smoke became a completely discrete content property, and everything else I’m producing fits into a content system, making it easier for me.

Effective Repurposing

I feel very strongly that when you repurpose your content, it should be fully yours, and it should fit the format of the platform you’re posting on. But that doesn’t mean fully reinventing the wheel.

My process is generally:

Write long-form articles (because writing is thinking).
Record a version of those articles for the podcast. Usually I’ll add more conversational asides to those.
Take the essence of the article and make it a LinkedIn post. Here is where I’ll use AI to pull out the main point, then evaluate what I wrote to see if it has a good hook and clear CTA.
Review the articles for good “show me” candidates that I will turn into videos.

Something I may experiment with is taking the videos and using AI to turn them into written tutorials. But I need to be really, really sure that what it produces isn’t slop.

Those are the platforms where I’m most active, and Paper & Smoke doesn’t really fit into that process because the content is so different. But it’s also too much for me to have both right now.

Knowing When Something Is Too Much

I’m doing a slight pivot in my business to focus more on client work — what we would have called “productized services” in 2017. But it’s really about having a clear system and deliverables for the people I can help.

I already have a good body of content to pull from, and a wealth of ideas in Notion and Obsidian. My focus needs to be:

Clarifying my offer to show people why it’s a no-brainer to hire me
Working on building my audience, exposure, and reach to generate leads
Creating content that serves 1 and 2

I know that, and I’m using the summer to completely optimize for those 3 things. This will look different for you. But if you’re anything like me, I’m guessing you have a few ideas you’re really excited about.

You need to figure out what will best help your business right now, so you can gain the time and space to do the side projects that excite you.

There may be a time in the future where having a separate publication that I grow and monetize — the very model Substack is built for — makes sense. I trust there will be.

But right now I’m trying to do too much — like letting all 3 of my kids be in different places at the carnival and trying to keep an eye on all of them at the same time.

The Fewest Links Philosophy: How to Build Automations That Don’t Break

2026-06-15T00:00:00Z

There’s a children’s game in Philly / eastern PA that’s called “Whisper Down the Lane.” Pretty much the rest of the USA calls it “Telephone.” If you’re unfamiliar with the game, a bunch of kids sit in a line, and the first person whispers something to the second. Then each kid subsequently whispers what they hear to the next person. The last person in the line then says what they hear out loud.

The entertaining part is seeing how much the message changes from the first to the last person. Maybe “The New York Knicks won in five” turns into “In New York: kick, run, drive.” The more people, the less likely the original message stays intact. The more complicated the message, the less likely it stays intact.

Or maybe you just have a chaos agent who changes it completely.

I was thinking about this game while thinking through a core philosophy I’ve mentioned a few times but have never fully explained: my Fewest Links philosophy.

It states that when it comes to automation, the fewer links in the chain, the better. And while Telephone¹ is fun when the message changes, with business automations it could lead to big problems.

An Automation That Was Too Clever by Half

Here’s one time an automation really bit me, and cost me possibly dozens of email subscribers.

When I first started using Kit.com (formerly ConvertKit), I didn’t like the way the forms looked…so I decided to make my own using WordPress, then set up a Zapier automation to send the info from the form to ConvertKit. This is despite ConvertKit having embeddable forms, and paid solutions like Gravity Forms having ConvertKit integration.

I failed to do two things. The first was to save the data in WordPress, so even if the zap failed, I’d have a backup. But hey, I tested the zap and it worked…so we’re good, right?

Right?

About a month later, I noticed that literally no one had signed up for my mailing list. I thought that was weird because sure, November is maybe slow; people are unsubscribing more than joining. But I’m usually good for a handful per week. So I decided to investigate.

That’s when I noticed the second failure: I forgot to turn the zap on. So people were filling out a form that didn’t save the info, nor did that info get sent to ConvertKit. I could have just used an embeddable ConvertKit form — one link in the chain — but instead I decided:

Custom form -> Zapier -> ConvertKit, and the Zapier link was broken. And it cost me mailing list subscribers, and my mailing list is the main way I sell my products and services.

Of course, the “fewest links” path was super clear here, and I decided to ignore it. What about in other instances, where it may not be as clear?

How to Figure Out the Fewest Links

Remember that the goal is always the fewest possible links — the shortest path. That doesn’t always mean a short path. Here’s an example:

This is my call router for Cal.com. Depending on the type of call, I want to take different actions. So this looks complicated, but the alternative would be 4 discrete zaps that all do the same exact check. This is actually the fewest links, because it prevents errors, and it prevents zaps from “colliding” and multiple outcomes from happening.

If, instead of Booking Created, Cal.com had a trigger called Booking Created From Specific Event, it might be simpler to have 3 zaps and then exclude the Fallback.

So how do you figure out the shortest path? There are a few ways when you’re starting out.

Look for Built-In Automations

The first is definitely the simplest; some apps will offer built-in ways to do intra-app automations. Notion, Airtable, and ClickUp, for example, all give you ways to automate inside the app. When I click a button in Notion, add a row to a different database. When I update a status in Airtable, send an email. When a new task gets added in ClickUp, automatically assign it.

These are definitely the fewest links. It’s 2 links within the same app, and while nothing is unbreakable, these have the least likelihood of breaking. And if they do, the onus is very clearly on one company to fix them².

Look for Direct Integrations

If you need to get two apps working together, look for direct integrations before going to something like Zapier. A direct integration is more reliable because it doesn’t need an intermediary connector.

For example, Notion has direct integration with Google Workspace and Slack. So I don’t need a Zap to send a message to my contractors when a row is updated in Notion. I can have Notion do that automatically.

Todoist has direct integrations for Gmail and Spark, making it easy to move tasks out of email and into Todoist. Obsidian has a browser-based web clipper, so I don’t need Zapier or some other third-party “highlights” app to send interesting quotes and articles to Obsidian.

The combination of built-in automation and direct integrations can also be very powerful. Again, everything is happening inside of the primary app. But what about when there aren’t direct integrations?

That’s when we look at automation tools like Zapier, Make, or even an LLM. But we want to take a simpler approach first.

When Using Automation Tools, Look for the Most Specific Triggers and Actions

In my Cal.com example, I talked about why that complicated, multi-branch automation is actually the simplest version: because there’s not a more specific trigger I can use.

For example, with Google Drive, there are triggers for “New File” and “New File in Folder.” The latter allows me to have a simpler automation because now I won’t need to filter, search, or take some other action that could lead to a false positive or complete failure.

When using triggers (the things that kick off automations) and actions (the things that happen after an automation gets kicked off), you want the most specific versions possible to remove ambiguity and prevent having to add extra steps for filters.

It’s only when there’s not a more specific trigger or action that you move to a more generic version…which will likely increase the number of links in the chain.

Now, if you do start to get super complicated with a tool like Zapier, there may actually be a simpler method…though it won’t seem like it at first.

Look at First Party APIs

I really thought about putting this at number 3 instead of last, but the truth is, this could be the most complicated…or at least it used to be.

Recently I was wondering if I’d be able to create a Claude Skill that would check a Notion table for any podcast episodes ready to be published, then send everything over to my host for that show, RSS.com, and schedule them. RSS.com has a pretty great API, so I decided to give it a shot.

And you know what? It worked. Like gangbusters. Claude referenced the API documentation, then built a skill to work with it. The chain goes:

Claude -> Notion -> RSS.com.

Doing this with Zapier, it would have taken many steps, even more tests, and a hope that my rubber bands and toothpicks hold up. OH, and I’d rely on a lot more services: Notion, Google Drive, some other AI feature, and multiple webhook calls.

With the app that Claude made, it runs automatically, pulls everything from one source (locally on my computer), and if it breaks, it can diagnose and fix the error.

Stop Playing Telephone With Important Workflows

No matter what you’re building, the best way to make sure you have the fewest links in the chain is to start simple. Try automating one part of a workflow first, then seeing how it goes before adding onto the automation, or adding a new automation.

The alternative is to create a long chain of complicated actions that will result in the wrong outcome, or even worse, no outcome at all.

Footnotes

I’m from New York. ↩
When things like this break, it’s easy to blame the “other” app. “We can’t do anything — they have to fix it.” Sometimes it’s true. Other times, both parties have blamed the other app. ↩

What’s The Simplest Action You Can Take?

2026-06-08T00:00:00Z

I remember the first time I went to see my accountant. I was around 19 or 20, and figured it was time for me to treat my side hustle of building websites as an actual business.

I had been reading books on how to start a business, and one talked about the Shoebox Method for accounting: just shoving all of your receipts into a shoebox for your accountant to sort out later.

Even back then — over 20 years ago — I knew the importance of having some system. I was a pretty sloppy kid, but in my business and school work, I was very organized.

I knew I had to be if I was going to be good at anything.

Something I hear often is, “your systems and automations look great, but I have no idea where to start.”

Back in 2003-ish, I was faced with the same problem regarding accounting. Before that, I wasn’t really tracking anything because I barely had expenses. I hosted my client websites on a web server I set up at home.

As things evolved into something that resembled an actual business with real income, expenses, and W9s, I knew I needed a system to track my expenses. So I set up a spreadsheet with 2 sheets: Income and Expenses.

I also had a binder with receipts, in case I needed them.

Today that system looks vastly different, and I’m using actual software and an accountant. All of my expenses go on a single card that is connected to the accounting software. But only after I started with that simple system.

So how can you do the same thing? I recommend these steps:

Think about where you spend the most time.
Take a single task or process you do manually.
Ask, “How can I make this slightly easier?”

That’s it. You take one simple step towards an easier process. Here’s an example: When I started batching podcast episodes, I would lose track of where I was with each episode. So I set up a simple Google Sheet with Guest Name, Status, and Publish Date.

That’s it! That was the seed that sprouted into a nearly fully automated system. When I hired my podcast editor, I would move files into Dropbox and then manually email the link to my editor.

Thanks to that first spreadsheet, I was able to set up an automation: when the status changed to “Ready for Edit,” email Joel.

The same thing could be said for cold outreach, my CRM, my YouTube channel, idea generation, and email inbox management.

But you still need to start somewhere. So your homework: take a single task you do, and ask yourself, “How can this be easier?”

I want to know what you come up with. Comment below and let me know.

Explain How You Work: The First Step to Automating Your Business

2026-06-01T00:00:00Z

Back when I taught Computer Science at The University of Scranton, I was tasked with teaching what most faculty viewed as an unenviable course: Computer Literacy.

It was a required course that all freshmen had to take, and we didn’t teach software development in it. It was essentially “intro to computers.” I really enjoyed teaching it.

It was a way for me to teach 18-year-olds about the evolving landscape of the online world. They’ve since changed the course to combine it with 2 other courses, but I would love the chance to talk to students about LLMs.

One class I remember clear as day is when I was teaching them how to use WordPress.com to set up a personal website — an asset I felt every young person should have in the early 2010s. I was telling them the difference between a “post” and a “page,” which is something I had done possibly hundreds of times before…mostly to people somewhat familiar with WordPress already.

As I finished this well-rehearsed description, I looked out over a sea of neutral-at-best faces in a classroom quiet as a church. One student mercifully ended the stunned silence by raising her hand and saying, “I have no idea what you just said.” About half of the class vigorously agreed.

It was at that moment that I realized I never had to explain this to someone who didn’t have at least a general idea of what pages and posts were. That single class changed my entire perspective on both teaching, and how I explain how to do something.

When We Explain, We Scrutinize

Part of the problem was that my explanation was never scrutinized by someone completely unfamiliar with WordPress. It was either WordPress people, or clients having me do the updates…they didn’t really need to know anyway.

I somehow went multiple years without the incredibly helpful exercise of explaining this fundamental feature. See, when we finally do explain something to someone completely unfamiliar with the process, three things happen:

We examine something we’ve done possibly so much we don’t think about it anymore.
We need to justify our approach.
We are forced to clarify our position.

In other words, we open ourselves up to feedback — both from ourselves and from others.

Kids Are Really Good at This

When I became a dad, I made a promise to never say, “because I said so.” I hate arbitrary and capricious rules, and “because I said so” is the epitome of arbitrary and capricious. If you can’t explain why you are doing something, you shouldn’t do it. I’ve broken this rule only a few times, each time either taking back the rule/punishment or taking the time to explain to my kids why I did what I did¹.

But rules that apply to them aren’t the only times they ask “why.” They have no preconceived notion of why something should happen, and “because I’ve always done it that way” doesn’t make any sense to them. I’ve learned a lot in my kids’ pursuit of answers, and my desire to answer them accurately.

It’s this childlike wonder that we need to take to our own systems and processes as solopreneurs and small business owners.

What Exactly Are We Explaining?

At this point you’re probably thinking, “Joe, we’re nearly 600 words into this and I don’t know what you want me to explain.”² The answer is simple, but maybe not easy: I want you to explain how you work.

When we’re in the thick of it, getting our business up and running, or launching a new project or product, we can live in a mode where we’re doing more reacting than planning. But if we want a less chaotic, more predictable business, we eventually need to understand what we’re doing.

This is what allows us to set up reliable, automated systems for repeatable work. So for this exercise, I want you to pick just one task. That’s it. Pick something that you do often.

Then you can explain how you do it and why.

Two Ways You Can Explain How You Work

When you explain how you perform a task, you should do it for two audiences:

Yourself, so you can review what you do, if you personally need to do it, and if it needs to be done at all.
Others, so they can either learn how to do it your way, or provide feedback on how you can do it better.

Stating the goal is important here because this is how we determine what “better” means. Not in a Simon Sinek “find your why” way, but in a “what’s the point of me doing this” way. If you don’t have a good reason to do something, you can save a lot of time by not doing it.

In both instances, you should fire up your favorite screen recorder. Lots of people use Loom. I personally like Tella because it’s super polished and very flexible.

Then state what the task is, how it starts (the starting point), and the result (or end point). You should also state why you’re performing this task, and what you hope to achieve from it.

Then, perform the task while narrating what you’re doing. Include as much as possible:

Apps, websites, and other tools you use
What kind of authentication you need
Any place the data you’re working with starts and ends
How long it usually takes you
Fields you need to fill in
“Gotchas” or variations on what could happen
Potential errors you’ve come across, even if they’re not shown on screen
The expected result
Any errors that do occur (keep talking through them)

…and anything else you can think of. These are going to be fairly universal in any task you record. There are a couple of differences that can occur based on audience.

When Recording for Yourself

When you’re recording for yourself, either to review or just to remember how to do it, you can also include:

How you feel doing the task: Do you like it? Hate it? Wish there was an easier way?
A quick tools assessment: How do you feel about the tools you’re using? Do you need all of them? Are you paying too much for one? It’s good to make these verbal notes in the moment.
Efficacy: If you’ve been doing it for a while, how effective is it with respect to your goal? Be honest with yourself here. If it’s new, what are you going to look for to determine if it’s effective?

Adding these three bits will give you more context if/when you go back and review this. It’s easy to forget why we started doing something in the first place, or to deal with the pain of using a tool because it’s easier than switching.

When Recording for Other People

The process will slightly change when recording for other people. Depending on who that audience is, you could still state the efficacy, but how you feel and the tools assessment should be framed slightly differently.

If you’re recording it strictly as a Standard Operating Procedure (SOP) for a VA or contractor, you can leave all of that stuff out. Make it as factual as possible — you don’t want to get the most important stuff lost in the weeds of internal metrics and feelings.

If you’re recording it for a coach, peers, or a mastermind group, you want to frame everything to elicit feedback:

When you talk about how you feel, focus on the things you like and why you like them. You can signal you’re still open to suggestions though. With frustrations, ask point-blank: “if you know a better way, let me know.”
With tools, talk about why you use them and if you need them or not. Again, ask, “if you know a better tool or know a better way to use this tool, I’d love to hear about it.”
For efficacy, state your goal and ask them if it’s reasonable, what seems to be working, and what isn’t. Ask them if they think something is missing, and if that goal is on-point, knowing what they know about you.
Ask them if they’ve tried something like this and how it worked out for them.
Finally, tell them they can ask as many clarifying questions as needed.

In this instance, when you’re not recording this specifically for an SOP, you want to give the recipient(s) as much context as possible without biasing them one way or another.

Getting Clarity

The magic comes in the clarifying questions. Just like when that student told me how confused she was, the clarifying questions can reveal blind spots and assumptions you’ve made.

One time, I was explaining my marketing copy and positioning to my mastermind group, when my friend Becky said, “You keep saying podcaster, but I don’t consider myself a podcaster. I consider myself a business owner who has a podcast.”

This statement changed everything for me: how I describe my services, the niche I talk to, and even the processes I help people with. Getting a second (or third) set of eyes can be hugely helpful — especially if you’re open to honest feedback and they’re willing to give it.

Are You Struggling With Your Tasks?

Because of this, I want to extend an offer to you: I want to provide feedback on how you work.

If you’re a solopreneur or small business owner, and you perform a task on a regular basis, I’d love to see how you do it. Bonus points if you feel it could be done better but you’re not sure how.

Using the form below, record a video and submit it. If your video gets selected, I’ll publish my feedback on my YouTube channel³ (I’ll also send it to you separately, and invite you to collab if you’re on YouTube).

Some considerations:

Pick a single task to record. I’m not reviewing entire workflows.
Try to keep the video between 5-12 minutes.
Make sure to obscure any personally identifying data you don’t want me to see. I’ll try to scrub it before I publish, but we may have different ideas of what should be scrubbed.
Make sure your screen is legible, and I can hear you clearly. Quality will matter here.
You do not need to be in the video, but you can be if you’d like.

I hope I’ve shown you how monumentally the act of explaining how I work has helped shape my business. I want you to see those same benefits, and I’m excited to see how you work.

I’ve also explained to them that sometimes I need them to do something without question, and they can ask later. “Do it now I’ll tell you later” is vastly superior to “because I said so.” ↩
Is that a sign of bad writing or decent storytelling? ↩
Not all videos submitted will be selected, but I will try very hard to personally respond to all of them. Videos selected will be published based on my publishing schedule, so I will not be able to provide a live date until after I’ve recorded a response. ↩

The Solopreneur’s Guide to Protecting Your Time From Everyone Who Wants It

2026-05-24T00:00:00Z

When I was in high school, I wanted people to like me. I thought being really nice was the way to do that, so any time someone asked me for a favor, I was much more apt to say yes than no.

Nowhere was this more obvious than in the lunch room, where every day my freshman year, a classmate we’ll call Jordan asked me for $1. Jordan was a pretty popular guy, so I figured if I gave him a dollar at lunch when asked, he might ask me to hang out with him outside of the lunch room.

But of course, that didn’t happen. He just knew he could get money out of me every time he asked, so he asked. One day, an actual friend of mine asked me why I kept doing it, so I decided to stop.

Jordan came up to me and said, “Yo my man Joe, lemme get a dollar.” I said, “Sorry Jordan. I’m not doing this anymore.” He was annoyed. But eventually he stopped asking. And my status in high school didn’t change at all.

Now, reading this as an adult, it’s probably incredibly obvious to you what Jordan was doing. It was very little effort for him, and if he didn’t spend the money, he probably ended up making $40-50 off of me and I got nothing in return.

But the truth is if you’re a solopreneur, you probably have a Jordan in your life. The client who calls you with every little thing. The “friend” who texts you to look at something real quick. Anyone who emails you where you feel you need to respond right away.

Because when you respond right away, you stop what you’re doing — something you should probably be focusing on — to do something on someone else’s todo list. And people adjust accordingly. They message you when they need something done now, instead of giving you some wiggle room to fit it into your schedule.

They are now spending your time. And unlike the money I gave Jordan that I was able to make back building websites, you can’t get more time back. But just like my situation with Jordan, you can put a stop to it.

How to Gain More Control Over Your Own Schedule

The way I see it, there are really 3 ways to gain control over your own schedule:

Protecting your most productive time
Determining what tasks you absolutely need to get done in a week
Using the right tools to help you

Let’s start with the first thing.

Protect Your Most Productive Time

Three summers ago I had a huge problem. Because I wasn’t working every day, I made my schedule as open as possible. I figured if people were meeting with me, or recording a podcast with me, I should accommodate them.

As a result, on my actual working days, I rarely had even 2 straight hours to work on my business. By the end of the summer, I was stressed and felt deeply behind on work.

The worst part is I already knew what a good day looked like for me. During the school year, I had my no-meeting days, and my dedicated meeting blocks. But I changed that for the perception of being more accommodating. I knew I couldn’t make that mistake again, so when the next summer came, I actually got more strict about meeting.

I pre-recorded a bunch of podcast interviews, and only made myself available to meet on Tuesday afternoons. I didn’t do a make-up day if I was off on a Tuesday. For anyone who couldn’t do those times, we handled it asynchronously. That summer went MUCH better. But crucially, I didn’t lose any work because of my modified schedule. People understood.

When you control your schedule, you can protect your most productive time, and people aren’t just grabbing times on your calendar. So here’s what you can do.

Figure out when you work best. You can do this by task journaling, checking in with yourself throughout the day, or just reflecting on when you feel sharpest and most productive. Once you figure it out, protect that time at all costs. Block it off on your calendar and be very, very stingy about giving that time away to other people.

Then, figure out when you generally feel least productive. I pick afternoons because between 2-4pm I struggle to find the motivation to get work done. Meetings, events, webinars, and coaching calls are a forcing function for me.

Once you have those two things, there are two approaches you can take:

Use time blocking on your calendar. Add events like “Deep Work” or “Productive Time” at your best hours.
Use a scheduling app with available hours for people to meet with you and use that calendar when people suggest meetings.

The most important thing: stick with this schedule. Protecting your time is crucially important if you’re going to get work done.

Determine Your Most Important Tasks

Once you know when you’ll get your best work done, you need to fill that time with what requires your best work.

I like to plan my entire week on Sunday mornings. I’ll write down all of my appointments, personal obligations, and projects I need to work on for the week. Then I’ll start to fill in my week.

I will plan 3 tasks per day; tasks with a higher level of effort go on the days when I have the most free time¹. For bigger projects, I’ll also try to break them down into smaller tasks, and I’ll group similar tasks (like recording content) together so I’m not switching contexts a lot.

The exercise will also help you determine how much wiggle room you have in a week. Things do come up, emergencies happen, and sometimes an actual friend reaches out and needs some help. But when you know your most important tasks — the non-negotiables you need to get done — you can prioritize them to ensure at least those get done.

Use the Right Tools to Help You

What’s the line? The road to hell is paved with good intentions? We can plan and try to protect all we want, but ultimately we might need a little help.

I already mentioned using a scheduling app to make sure people can only book meetings during your preferred meeting times. But there are other tools and systems you can use to protect your time and do your work better.

There are apps like Raycast’s Focus Mode that will help you stay focused by closing distracting apps (like email and social media). Or, just using the Do Not Disturb function on your phone and computer to kill notifications.

For something stronger, physical devices like The Brick can prevent you from getting distracted by your phone. That way, you have to walk to a device and scan it if you want to use your phone.

But it’s not just about blocking distracting apps; you can also leverage tools and automations to do your work better.

Tools like SaneBox or Claude can help you better manage your inbox so you don’t feel like you need to be in it all the time. And even simple automations can help you free up your time from easily repeatable process work so you can do your best work.

If you’re not sure where to start here, I recommend using the Task Audit Matrix to sort out what you need to do vs. what you can automate.

Try the Task Automation Matrix

Keep More of Your Time Yours

I wish I could tell you that Jordan and I ended up becoming better friends or that I saw him years later and he apologized for taking advantage of my generosity. But the truth is we didn’t really talk all that much in high school, and I haven’t seen him since graduation.

That’s the thing about a seemingly simple ask: most people think because it’s easy for us to do something, it doesn’t have much of an impact on our day or our work. But a quick ask for them can derail us.

With this process of protecting your schedule, determining your non-negotiable tasks, and using the right tools, you’re ensuring that your day is mostly yours, and you’ll work in a way that works best for you.

Once you put that signal out there that you respect your time, and manage expectations, other people will too.

Note here: I do block off my most productive time, but some things, like school obligations and childcare can affect how many working hours I have in a day. ↩

What SNL Taught Me About Solopreneur Automation

2026-05-11T00:00:00Z

I was watching Noah Kahan, the SNL musical guest over the weekend, when I came to a realization about why I’ve had a pretty big resurgence in my interest in the show lately.

Yes — part of it is the 50th anniversary last year and the increased media coverage around the show. Part of it is the sketches are available on YouTube and Peacock+, and easier to watch.

Doing It Live

But it’s more than that. And it wasn’t until I watched the last few musical guests (something I usually skip) that I realized why. On SNL, you’re really doing it. It’s live. You need the talent. You need the skill. And you need the confidence to excel, and be willing to mess up.

I know I’ve been talking about AI a lot lately. Seems like everyone in our space has. But it’s against this backdrop that I was thinking about SNL. Noah Kahan sang live and it was impressive. So did Olivia Rodrigo. It’s a requirement for the show, and the one time someone didn’t, they were universally panned for it.

The sheer force of effort needed to do a single show is amazing too. You basically have a week to write and rehearse the entire thing, with some changes coming during the final dress. You need to be prepared.

AI Cannot Replace This

Then there are people who are too scared, or lazy, to make any decision without the help of AI. “Well I’m not good at this — Claude is better,” or “I’ve trained it in my voice so it’s OK.” This is how one gets worse, not better. By not practicing something, you’ll never get good at it. By not continuing to do something, you’ll get worse.

Couple this with a fantastic article I read called The task is not the job, and you’ll see why I’m finding even more inspiration in what SNL is doing. People still want human interaction. They want human relationships, and they want human experiences.

As solopreneurs, we’re better positioned than many to offer these. We can tell people, “when you hire my company, you get me.” But I also understand that many turn to AI because they don’t feel they have the time to do everything.

Automate The Process Tasks

So what can you do? You use AI and automations for process stuff — your planned, repeatable tasks that can run in the background as automated systems. You don’t have to do them, freeing up your time to do the work that truly matters.

An example from SNL could be the structure of the show: cold open, monologue, usually a pre-taped sketch, etc. They don’t need to start from scratch every week, so they can focus on writing that fits the format. It’s also the dozens (or maybe hundreds) of processes they have for costumes, makeup, set design, and everything behind the scenes that we don’t see.

I feel like we’ve lost the thread on this. And much like we’re better positioned for deeply connective work, we’re more susceptible to losing our businesses to AI. Not because people replace us with Claude, but because we let what makes us truly valuable atrophy.

I’ve been thinking of a way to combat this. Just a few years ago, the main problem was, “I don’t know what I can automate.” Today, it’s “everything seems automateable, from emailing clients to creating video.” In other words, the problem is distinguishing what in our process should be automated.

A Possible Solution

So I’m working on a new cohort called Automation Foundations. It’s designed to help you automate the planned, repeatable stuff so you can focus on connecting with your customers, and solving their problems in a way a glorified word calculator can’t.

If you’re interested, join the mailing list below to learn more…

4 Warning Signs You’ve Got AI Brain Rot (And How to Prevent It)

2026-04-25T00:00:00Z

Picture this: you wake up and you have this weird feeling…but you can’t quite put your finger on it. This feeling of doubt…like you’re struggling to think clearly. Like you’re in a bit of a brain fog.

“I’m sure it’s fine,” you think. Some coffee will clear that right up.

You go about your day. You notice you have an issue with your website. You ask Claude, “My website isn’t displaying my podcast episodes the right way. Can you fix it?” Of course! Claude pinpoints the problem and then asks if you want it to deploy the code for you.

A little later, you need to write an article. You ask Claude, “Based on my 10 best-performing articles, what should I write about next?” Claude gives you a list of pretty good ideas, then asks if you want it to draft one of them for you.

After a meeting with some people in your mastermind group, you realize that you need a better product. So you ask Claude, “Based on what you know about me, my area of expertise, and what I’m currently selling, can you come up with something new for me to sell?” Claude comes up with a great idea for a digital product, then asks if you want it to create the outline or slides for it.

At the end of the day, you’re talking to your partner. “How was your day? What did you do?” And that’s when the feeling solidifies: you have a vague idea of what you’ve checked off your list…but you don’t really feel like you’ve done anything.

…so you ask Claude.

How are YOU Feeling?

You probably had 1 of 2 reactions to that story: deep resonance, as I did recently. Or complete skepticism.

If you had that first reaction, you’re ready to hear this. If you had the second, you’re not. But hopefully I’ve planted a seed. Come back when you’re ready.

Or maybe there’s a 3rd option; you already have a good handle on your use of AI, and you don’t need this. I thought I did, until I tried Claude Max. It’s pretty impressive, but a few days in, I had this sinking feeling. The same one I had last year, when I was asking regular old Claude everything.

“Am I asking AI to do too much for me?”

When AI Does Too Much For Us, Our Brain Atrophies

My friend and I were at an event recently where we talked, among other things, about how too many people are experiencing AI Brain Rot. Where they literally can’t do anything without asking AI first.

You might think it won’t happen to you. And maybe it won’t. I don’t know you. But here’s what I’ve seen solopreneurs use it for over the past few months:

Coming up with, writing, and publishing articles on their behalf
Using it to write responses to people seeking their advice
“Thinking” of questions they should ask their audience
Having it come up with questions they should ask during webinars and workshops
Thinking of and creating products
Using it to “have a conversation” with deceased relatives¹

You’ve probably heard that your brain is a muscle. It’s not. But it is true that if you don’t use it, you lose it. By having AI do more thinking for you than you do for yourself, you will lose the ability to think critically…and to do anything well.

We’re all different; we have different thresholds, skills, and standards. But I want to share with you what I think are 4 warning signs that you’re experiencing AI brain rot.

#1 You’re a Reflexive User: You Can’t Think About Something for More Than 5 Minutes Before Running to an LLM for “Advice”

This is the first and biggest. During a talk I gave at Podfest 2026, someone asked me how to know if you rely on AI too much. This was my answer: if you can’t think about something for more than 5 minutes without going to AI, you rely on it too much.

It seems like we’re being much more productive, but the opposite is happening: we’re doing things with no direction. That’s a poison pill for solopreneur systems. But there’s something even worse happening.

If I were to put it more extremely, I would say it’s just like any other chemical dependency: you don’t feel like you can function without it².

We need to be able to sit in problems and think about them. Not just for a few minutes. For 20, 30, 60. Maybe more. This is an exercise we should practice regularly.

Running to AI at the first sign of friction, coupled with our increasing inability to be bored, is having a terrible effect on our collective ability to think critically.

The next time you have to solve a problem (what article to write, some part of your customer journey, how to talk to your kids about something), I want you to leave your phone in a different room, take out a pen and paper, and just spend 20 minutes thinking about it.

#2: You’re a People Skipper. You’re Not Talking to the People Who Matter

The second is that you’re letting AI act as a proxy for talking to actual people: customers, stakeholders, business partners, or mastermind members.

We need to remember that AI is a massive word calculator. It’s really advanced autocomplete. It’s the best contextual search we have. It is not human.

When you ask LLMs something and then treat it as a problem your audience has, you’re not serving your audience. You’re serving yourself. Instead, take out the old pen and paper and write down 5 questions you have for your audience, customers, stakeholders, etc.

Then actually email those people those questions. Create a survey or a poll. Get real feedback. Have actual calls with people. I promise you can use an LLM after that to:

Find primary sources on the problems they have
Summarize and process the data you’ve gathered
Show you interesting data points

Doing it later is important because then you’re not getting fictional analysis. You’re doing it with real data, from real people — which is what you have to do, unless the LLM is your target customer.

#3: You Have No Skin in the Game

The final reason might be the most tangibly impactful: you have no skin in the game. And the reasoning is simple: you didn’t actually come up with it, so you care less.

It’s like a poker game without real money, or a scrimmage game where you’re not keeping score. There’s nothing to play for. When we don’t have something driving us, we’re less likely to commit.

How does this shake out with AI? Well, let’s say you have it come up with a content strategy. You’ve trained it on your YouTube channel, told it what works and what you want to do, and it comes up with 20 ideas for you to start with. But creating videos is a heavy lift. And sure, it gives you a title and maybe a synopsis, but you’re not clear on how to execute this.

Because it’s something else’s idea. I fell into this exact trap. I thought it was great that it could analyze my content — everything on my podcast, YouTube channel, blog, and newsletter. But then instead of just telling me the insights, it came up with this deep plan that focused too much on a single aspect.

Because the ‘work’ was already done, I decided to give it a try…but I realized I didn’t care about most of what it came up with. So instead, I broke out a notebook, and wrote down 50 of my own ideas.

Then I used the LLM to compare the ideas against what performed well, and picked 10 to start with. Once again: using AI to supplement your thinking with data, not do the thinking for you.

And if you’re worried you’re slipping into the cold embrace of AI brain rot, don’t worry. It’s not too late.

#4: The Empty AI Advisor. You Turn to AI for “Coaching” or Advice

This is also very dangerous and combines the previous 3 signs. Instead of thinking about a problem (Reflexive Use), you run to AI instead of taking to a person (People Skipper), to get advice or a plan that no person has put any thought into (No Skin in the Game).

It’s important to remember that AI doesn’t think. It doesn’t have opinions. And most importantly, it’s designed to placate us. It will agree with you at the sign of any pushback; that’s not a coach or advisor.

That’s a sycophant.

How to Prevent AI Brain Rot

AI brain rot isn’t permanent, and it’s preventable. Here’s what to do.

I think the most important thing you can do is create a set of rules about what you’ll use AI for. I’ll share mine in a minute, but they are all informed by the 5 pillars of my AI Philosophy.

My AI Philosophy

Don’t use LLMs for thinking work
Don’t refer to what LLMs do as “thinking”
Don’t personify LLMs
LLMs/AI are computers, and they are best for doing computer things
Remember the cardinal rule of programming: computers do exactly what you tell them to do.

With that, here are my rules…

Rule 1: Use the Computer for Things Computers Are Good At

This includes crunching a lot of data, transcribing meetings, processing written notes, and updating apps like Notion and Obsidian with my work, not its work.

We are living in an incredible time where we can literally have the full context of all of our meetings, calls, and conversations at our fingertips. THEN we can have a very smart computer process all of that data for us. This is a great use for AI.

…just remember to take your own notes too.

I will also use it for coding. I have complicated feelings about it, and there are guardrails you need. But it’s very effective at writing code (after all — it’s basically speaking its native language here).

I’ve used it to write simple plugins, web apps, and even an iOS app — something I have no personal experience doing. As a former Software Engineer, I try to be very clear in my requirements, think about how a human will use the software, and test rigorously. But LLMs, especially ones like Claude Code, have gotten really really good at coding over the last year.

Rule 2: Think About the Problem You’re Trying to Solve for at Least 30 Minutes Away From a Computer

When I’m thinking through a problem, I like to either:

Go for a walk
Write in my notebook at my writing desk or front porch
Plan at my whiteboard

The important bit is that you’re not doing it at a place where you can get distracted, or give up and go to the LLM. This will give you time to sit in the problem and come up with your own solution.

It will help you “work out” your brain so it doesn’t atrophy. But I know what you might be thinking: “I log ideas on my phone, and I have the LLM app on my phone too.”

Don’t worry…I have a solution.

Rule 3: Remove It From Your Phone

I know this is a big ask. But much like with social media, always having it on you means you’ll start to use it more as a companion than as a program. You have a random thought and you decide to ask the LLM. You’re struck with inspiration, and you start using the LLM as a “thinking buddy” — a hilarious moniker to me because at that point neither party is actually thinking.

That doesn’t mean you can’t use your phone to help you think through stuff. If I want to take the output from Claude (like analysis of data, for example) with me, I have it save a file to my Obsidian Vault or to Google Drive.

For capturing, I have a completely separate transcription app: Whisper Memos³. That way I can record my thoughts completely and then work with them later. This includes having Claude or some other AI thing summarize it.

The idea here is to remove the temptation of running to it for everything.

So now that you know how to recognize AI Brain, and how to prevent it, what does your life look like?

Fast Forward A Month

You wake up feeling refreshed, and ready to tackle the day. That nagging feeling you had a few weeks ago is gone. You actually feel like you’re doing your best work…that your work days aren’t just a fog of vague prompts and even more vague output.

You notice an issue with your website. You ask Claude to fix it; Claude obliges. It’s very good at writing code because it’s a computer doing a computer thing.

You need to write an article. You ask Claude to analyze your website and YouTube analytics to show you the best-performing articles. Then you ask it to summarize 10 customer research calls you had with actual people to find the objections they had, and cross-reference them with your articles. You take that data and write out 20 article ideas. You pick your favorite and get to work.

The product that Claude came up with last month is a dud. So, using those saved customer research documents, as well as comments on your content and emails from your audience, you ask Claude to find the problems your potential customers are saying they’re having, using actual quotes from the source material.

Claude puts it all in a document, which you convert to audio; you go for a walk, listening to it and thinking through how you can best serve your audience.

At the end of the day, you talk to your partner. They ask, “So, what did you do today?” Unlike last month, you have the answers. You came up with a bunch of article ideas and wrote one. You came up with a product that should actually solve a problem for your customers; now you’re working on a 3-question survey to get feedback on it.

This time, you don’t need to ask Claude what “you” did, because you did the actual work of running a one-person business. And you left the computer stuff to the computer.

Look. I know we all grieve in different ways. But part of the grieving process is acceptance. My gut is that this will prolong the grieving process (or at least, prevent you from fully accepting reality), and I spoke to a couple of psychologists who agree. ↩
We are already seeing this. People who say, “Oh, my AI is down; I guess that’s a sign I should take a break.” I take breaks when I want, and when AI goes down, I keep working. ↩
Though, full disclosure, AudioPen just revamped their app and I’m a lifetime member of that, so I’m stoked to try it out. ↩

Two Weeks with Claude MAX: A Solopreneur’s Honest Review

2026-04-20T00:00:00Z

For all of my talk about how terrible LLMs (AI, colloquially) usually are, it might seem surprising to you that I shelled out $100 for a month of Claude MAX*, and will likely do it again.

But my beef with LLMs isn’t that they exist. It’s almost entirely the way people are using them, which is almost directly a result of the way AI advocates talk about them.

Case in point: Cal Newport’s latest podcast episode, Is Claude Mythos Terrifying? | AI Reality Check, completely debunks what Anthropic’s CEO said, proving that the “terrifying” risks existed not only in the previous version of Claude, but in much less capable LLMs.

My AI Philosophy

As a reminder, these are the principles of my AI philosophy:

Don’t use LLMs for thinking work
Don’t refer to what LLMs do as “thinking”
Don’t personify LLMs
LLMs/AI are computers and they are best for doing computer things
Remember the cardinal rule of programming: computers do exactly what you tell them to do.

It’s important to keep in mind that LLMs are word calculators. Autocomplete that’s really advanced. The most contextual version of search we’ve ever had.

When you remember those core principles, it becomes easier to determine what LLMs should and should not do for you.

So with all of that, what am I using Claude MAX for? I use it for Computer things.

How I’m Using Claude Max in my One-Person Business

Here’s a short list of concrete solopreneur tasks I’ve used it for:

Number Crunching: Looking at analytics across my podcast, blog, YouTube channel, and newsletter, and seeing what topics are most popular. I used this info to also help with keyword research, as my general SEO strategy has been bad.

For example, my most popular blog post ever is a review I did on sleep headphones. It’s so misaligned with what I do I can’t even think of a good CTA, and there are no affiliate links in it (which is, I suspect, why it was so popular).

Processing Customer Research and Feedback: Uploading lots of coaching and customer research calls to find patterns in speech, how my customers talk, and any objections they have.

Aligning on My Goals: Using those crunched numbers and found patterns, I’ve come up with a general content strategy where the LLM creates “buckets” of content for me based on what works.

An extremely important distinction on the content strategy is that it’s not suggesting content ideas. Just “themes” based on what’s worked for me in the past. With the themes, I will get out a notebook and write 20-50 actual topics or ideas I have, then feed those into the Content Strategy skill, and have the LLM sort my ideas into the predetermined buckets and flag anything that doesn’t fit into those buckets so I can either refine, nix, or do it anyway.

Content Packaging: Using all of the above, I have projects and/or skills to help take the content I’ve come up with and create packaging (titles, descriptions, thumbnails if needed). It also makes sure that I’m using all of my stated keywords in some way.

Why This Works

All of these things are possible because of two things:

A much bigger context window and Claude doing clever things to keep the context over long chats.
The ability for Claude Cowork to access folders (one of which I’m calling AI Memory) and connectors like vidIQ, Notion, Senja, Supernormal, Todoist, HubSpot, and more.

Giving an LLM the ability to access as full a context as possible makes its answers “smarter,” but it can also crunch data better, which is really the crux of what I’m using it for.

Other Helpful Use-Cases for Solopreneurs

A few other ways I’ve found it helpful:

Copy Editing: This is a long-standing use-case. It never touches my work; it only proofs and suggests changes. It’s just a lot “smarter” now because it has much more context and data.
Deep Research: Mostly it surfaces a large number of primary sources for a piece I’m working on. Something worth mentioning is I never read the summary alone. I read the summary, then go to the sources that seem the best and pull all of my references from there.
Coding: I have feelings about this, but it’s been really good at code. After all, it is a computer speaking the language of computers.
Call Summaries: Cowork has scheduled tasks. Every day at 6pm I have it check my email for Gemini Notes + Supernormal for other call notes. I have it summarize everything, and add my action items to Todoist.
Calendar Management: My calendar app, Fantastical, has MCP, So it can access all of my calendars without giving the LLM direct access to all of my accounts.

Example: Adding Yankee Games to My Calendar

One pretty cool thing I used Cowork for was putting all weekday afternoon Yankee games on my calendar. I usually don’t realize the Yankees are playing an afternoon game during the work week until after I have a conflict. So I had Claude:

Go out and get the Yankees’ full schedule.
Determine the games between 11am and 6pm ET Monday – Friday.
Put those dates on my primary calendar so they’re blocked in Cal.com. I also know not to schedule meetings at those times.
Add the entire schedule to a separate calendar called “Yankee Games.”

Once I fixed a sandboxing issue (that is, a security issue preventing Claude from going to any website), it worked flawlessly. This saved me a ton of time for so many reasons…one being it’s not really a task I needed to do.

Shortcomings

Now, it hasn’t been perfect. Far from it; it still does that LLM thing of making stuff up, forgetting directives, or overzealously suggesting too much. It even made a change to Notion I didn’t want it to.

One of my shortcomings is that I don’t think I’ve read its output as carefully as I should or could have. One of my tasks for this week is to audit everything in the AI Memory folder and make adjustments — something I can do without an LLM because it’s all plain text written in English.

On balance, it has saved me a ton of time and enabled me to do more targeted work than I would have…effectively and efficiently. Combing through all of my analytics, for example, isn’t something I would have done well, if at all.

Solopreneurs Should Trust Their Gut

That said, I want to make this really clear: I trust my gut more than the LLM’s output. Some of the rules I have are baked in to keep me accountable and remind me of decisions I’ve made. But it will often focus too much on a rule or concept (like everything pointing back to my Solopreneur Sweep).

Because ultimately, the cardinal rule of programming still applies: computers do exactly what you tell them to do.

*I know MAX is a plan, but the context of “more expensive plan” is important here.

Efficiency Isn’t Enough: What Every Solopreneur Gets Wrong About Productivity

2026-04-16T00:00:00Z

Beatles drummer Ringo Starr talks about how he moves his arms as little as possible when playing the drums. He said, “It’s all in the wrist.” This can seem counter to what many drummers do — which is to gesture with their arms wildly. I’m definitely guilty of that. The point he’s making is this: why would you waste your energy flailing your arms around when you’re most effective playing primarily with your wrists?

Your goal as a drummer is to keep the beat and tempo for the rest of the band. But aside from that, you’re a better drummer when you know it’s all in the wrists.

Depending on your drum set, you de facto have to move your arms (like to reach far-off cymbals)¹. But you want to conserve your energy for the most important work…especially if you’re playing long shows. Playing with your wrists is both effective and efficient.

In business, we often hear about what’s “efficient.” “Can I do this thing faster?” But efficient doesn’t always translate to effective…so is it really efficient?

So as solopreneurs, how do we figure out if we’re “playing with our wrists,” so to speak?

Know the Goal

You can’t measure efficacy until you know what makes something effective.

I was…having a spirited debate…with someone who built an “AI agent” to “write” for them. They train it on their thoughts and it presents ideas. The ideas get approved, and the LLM writes the article. A few rounds of feedback, and boom. Published article they didn’t write a word of².

This is incredibly efficient. But one answer I couldn’t get was: what’s the goal? Is it to convert people to their mailing list? Get people into their membership? Hire them?

And are the articles the LLM wrote doing that? Because if not, you’re just efficiently creating slop. You’re not being effective. And worse, you spent a ton of time building an engine that doesn’t work.

So step one is define your goal. Once you know the goal, you can measure both efficiency and efficacy against it.

Do the Thing Yourself First

When I first started playing the drums, I didn’t use my wrists at all. I flailed my arms about, trying to do cool fills without really understanding that my goal was to keep the beat³. But as I learned more about how to play, I understood that wrist action created better drum beats, and allowed me to move about my kit faster.

You don’t know what’s efficient or effective until you know what you’re doing. Until you understand what works and how it works. If you’ve ever spent a bunch of time developing an online course just to launch it for no one to buy, you know this.

Maybe the way you did it was super efficient. But if no one buys it, it’s not effective. Instead, you want to test your content with your audience, run a live training so you can get feedback, refine, iterate, and then launch it.

That brings me to my last point.

Optimize for the Goal

Once you do something a few times, you should have a good understanding of how it can effectively achieve your goal. That’s when you start to optimize. Automate parts of it so you can focus on the tasks that require your brain and your voice. Delegate tasks that require a brain, but not yours.

For example, instead of manually copying scheduled calls into your CRM, you can use Zapier or built-in automations. Instead of designing thumbnails or other graphics, you can delegate that out to a designer.

Delegating YouTube thumbnails is one of the best things I did to free up my time for a few reasons:

They are important so you want to get them right
I am bad at making YouTube thumbnails
I would spend a lot of time on them

My goal with YouTube is to get people to watch my content and sign up for my mailing list. I know good packaging (title and thumbnail) is the most important thing to get people to click…but good content makes them stay until the CTA. Now, I have someone working on good packaging, so I can focus on creating better video content.

When you automate and delegate in the name of your goal, you will have much better outcomes.

Efficacy is the Ultimate Efficiency

Ringo Starr is in his mid-80s, and is still touring, playing 2-hour shows while playing the drums and singing (which by the way, is really hard to do).

In a recent interview, he credited his longevity and health to eating broccoli. But if he went out there every night playing the drums in a way that looked cool but burned a ton of energy, he wouldn’t be a very good performer…at least not for very long.

As you approach your solopreneur business, this is something you need to keep in mind: efficiency isn’t just doing something faster, and efficiency alone isn’t going to help you achieve your goals.

You need to be effective. That’s the ultimate form of efficiency.

Ringo also keeps his drum set simple. ↩
They said it was important to have a “human in the loop,” but really this is more like the human looking at the loop through a telescope. ↩
…and occasionally, play a cool fill. ↩

The Framework I Use to Decide If a New Tool Is Worth It

2026-04-14T00:00:00Z

Over the last week or so, I’ve introduced several new tools that I’m either trying or evaluating.

One is a tool of my own creation, based on my task journaling process, called Daily Three. The second is Claude MAX, to see what the latest and greatest actually gets me (more on that in a different piece).

The third tool I’m trying is Wispr Flow, after weeks of hearing about how great it is. This one has the potential to usurp my absolute favorite voice transcription app: Whisper Memos.

One quick note is that Wispr Flow is much more expensive than Whisper Memo, so I don’t intend on keeping both, and Wispr Flow really needs to prove its worth.

This sort of conundrum is one that solopreneurs run into all the time. We start to wonder if there’s some tool that will help us be more efficient, so we start trying new things — and upending our current workflows — without thinking about efficacy.

So what do you do when you think a tool can help you, and you want to properly evaluate it…then maybe add it into your current system?

What Job Does The Tool Have?

The very first thing you need to do is answer the question what job the new tool has. Of the three I mentioned, Wispr Flow is really the only tool that might replace a long-standing tool in my system.

The job here is “allow me to quickly capture ideas, and send it to the right place based on context.”

Once you know the job, you start making it do that job. What you should avoid is just “playing” with the tool to try and “sell” yourself on it. Actually use it in your processes instead of the current tool, and see how it goes.

Wispr Flow actually can’t do a lot of what Whisper Memos does for me…like keep the recorded audio, send it to an email address (which I then pass-on to Obsidian), or integrate with Zapier. But it can do a lot more, so I’m wondering if that could improve my process.

Is The Change Worth It?

And that’s the second part of the evaluation equation: is the change in your process worth it? As long as it does the job both efficiently, and effectively.

For example, if I can record my audio while Wispr Flow transcribes it, and I don’t need to jump through hoops, great! Maybe I can just talk directly to Obsidian this way. The fewer links in the chain, the better.

But I need to figure out quickly if it’s not going to make more work for me. I don’t want to trade efficiency — being able to talk to my computer faster — with efficacy, which would be the tool doing the job it has well.

The best-case scenario when you do this is the new tool slots right into the old tool’s spot. You’ve either saved money, or can accomplish the job faster, or have access to some new features that will help you.

Second best is you decide your old tool still works well. You’ve spent a little time evaluating, but you’ve decided your current setup is as good or better.

But the last scenario — that you should switch, and you’ll need to rework your system — is where the trouble comes in.

How to Make the Switch

What exactly to do here is nuanced and depends on how crucial the system is, and how many moving parts you have, but the goal is to not break everything.

When I switched from Dropbox to Google Drive, it was shockingly simple. I maintained both services for a bit, until I was able to update my automations.

Switching from Calendly to Cal.com was a little harder, but worth it. I had to update links, automations, and emails that went out, on top of migrating all of my calendars over.

If you’re going to do this, you should consider:

Every place that relies on the current tool
If you’ll need to update any links
If you can maintain both services for a while

The bigger the change, the more it has to be worth it. If I ever move podcast hosting platforms, for example, it’s a monumental change that will require lots of updates in several places, plus testing over at least 1 month to make sure nothing breaks. I’m going to need feature parity at a minimum, plus long-term cost savings and/or better features.

Wispr Flow might be different — if I decide to switch at all.

What shiny new tool are you looking at right now? Did you define a job for it? Comment and let me know!

What High CO2 Levels Taught Me About Fixing My Business

2026-03-30T00:00:00Z

We’re coming out of a long, cold winter, and I’ve gotta say, I’m pretty excited about it.

There was one point where we were all just feeling super sluggish — and more than just that kind of “it gets dark at 5pm” sluggish. Like a weird, can’t keep our eyes open, brain-foggy kind of sluggish. I didn’t think anything of it…until I went away on a trip and immediately stopped feeling it.

I Didn’t Understand What Was Happening

I started to think it was our environment, and from the depths of my brain, remembered that higher CO2 levels could cause brain fog and tiredness. So I got 2 air quality monitors for the house.

And you know what? Our CO2 levels were high. Not dangerously so, but definitely higher than they should have been. Luckily, there was an easy fix.

In Germany, they have a practice called Lüften, where they open all the windows in their house for 5-10 minutes. This airs out the house, reduces humidity, prevents mold, and yes…exchanges CO2 for Oxygen. They do this even in the winter.

Once we started opening our windows (something we now precede by saying we must “Lüft”, the German word for “air”), things got better. We feel better, we sleep better. We manage to stay up to watch The Pitt after the kids go to bed.

All of this started because we tried to understand the problem by asking the question, “why do I feel sluggish when I sleep at home…but not in a hotel?”

Do You Understand Your Business?

Maybe you’re feeling tired and overwhelmed in your business. Simultaneously stressed about the work you do, but also that you don’t have enough income coming in.

Maybe it’s that you feel like you’re working through dinner or soccer practice. You haven’t seen your partner for more than 10 minutes because you have too much to do.

This is not a normal way to run a business — not even a solopreneur business where you feel like you have to do everything yourself. But you can’t fix it until you understand the problem.

Know Your Time, Tasks, and Tools

Luckily, I have a solution for you. It’s called The Solopreneur Sweep, and we look at 3 important aspects of your business to see what we can clean up:

Your Time, by reviewing your calendar
Your Tasks, by reviewing what you actually do in a week
Your Tools, by reviewing what you actually use vs. what is a distraction

Later this week I’m releasing a full video that walks through the entire method, but here’s the general idea. To protect your time to do the most important work, you need to:

Create chunks of uninterrupted time for you to do work
Make sure your task list isn’t dictated by other people
Assign jobs to your tools, and stop wasting money on tools you don’t use

The Solopreneur Sweep will help you understand the problems in your business so you can start to fix it.

It will be like a breath of fresh air.

Right now, I want you to start thinking about which of these three things (your calendar, your task list, your tools) are the biggest hurdle for you.

And if you want to know as soon as the Solopreneur Sweep video is published, join my mailing list:

Daily 3 Task Journal: A Simple System for Understanding How You Work

2026-03-23T00:00:00Z

My absolute favorite task manager is Todoist. I’ve been around the block and used all the major ones — from Remember the Milk to OmniFocus and everything in between. Todoist is the best for me.

But a task manager only tells part of the story — it tells us what we got done.

It doesn’t tell us anything about how we were feeling that day. How many tasks we moved or ignored. How many we checked off just so we’d stop seeing them.

And it shouldn’t. I use Todoist so I know everything I have to do. I don’t use it to dictate my work day.

Instead I use two systems for keeping track of that stuff. One is my weekly planning session (I’ll talk about that in a different article).

The other is my Daily 3 Task Journal.

How to Task Journal

The premise is simple:

Pick 3 (and only 3) tasks to perform that day. The idea is that if you get those 3 tasks done, you consider the day successful. They can be as big or as small as you’d like.
About halfway through your day, check in with yourself on the progress. Ask how things are going, what you’ve gotten done, and what you’re struggling with. You can be as verbose, or as curt, as you’d like. Just make sure to capture thoughts on how you’re feeling.
At the end of the day, assess your work. Did you complete the 3 tasks? Why or why not? What was effective? What distracted?

The idea here is to track not only what you intend to do in a given day, but the events throughout the day that helped or hindered you.

Maybe you didn’t get everything done because you had too many meetings. Or people kept interrupting you. Maybe you bit off more than you could chew (something that happened to me on Friday).

Maybe you just weren’t feeling it.

If you did get everything done, maybe it’s because you had 3 uninterrupted hours to get your crucial work done. Maybe your energy levels were high because you slept great the night before. Or maybe you picked easy tasks because you knew you wouldn’t be able to do anything too deep, as I did last Thursday — the day after I got home from a conference.

What’s the Point of Task Journaling?

If you do it right, you’re getting a handle on how you work — so that you can build a better system that saves you time.

Knowing how productive you are in a day, and what aided or prevented you from getting all of your work done, allows you to structure your days better. Deliberately limiting yourself to 3 tasks per day forces you to identify the 15 most crucial tasks (assuming a 5 day work week).

Then you can move or stack meetings. Block off time for deep work. Say “no” or “it can wait” to the things that aren’t in those 15 tasks.

Daily 3 App

This method is so important to me that I actually used AI to create an iOS app for it. It’s called Daily 3 Task Journal, and it sends me 3 push notifications:

6:00am — What 3 tasks do I need to accomplish today?
12:00pm — How am I progressing?
6:00pm — How did I do?

Importantly, you can only ever add 3 tasks, and they don’t roll over. I also have widgets for the Home Screen, lock screen, and Standby mode. I added Shortcuts support (natch) so I could easily export the entries to my Daily Note in Obsidian.

It’s worked so well for me that I decided to submit it to the App Store and it’s available as a beta on TestFlight.

If you’re not an iPhone user, or you’d prefer not to download an app, I also have a Notion Template. You can get both by joining my mailing list here:

You can also use whatever tool you prefer. The method is the important part. It can serve as the foundation for better work that gives you time and space to do the things that really matter.