When Do You Burn All of Your Processes Down and Start Over?

Last updated: July 8, 2025

It’s been quite a week, my friend.

Last week I started to feel sick, undoubtedly catching the plague my children have had for the past 2 weeks. I was the last one to fall.

Happily, I’m feeling better, but my entire week was thrown into disarray.

And it’s during the disarray that you see the cracks in your processes. While mine are pretty good, I’m growing tired of some of the tools I’m using.

In-fact, earlier this week on social media, I posted that I’m moving most of my operations to Notion from Airtable.

This is probably surprising, considering not 5 months ago, I wrote a piece proclaiming the exact opposite.

So what changed, and why am I deciding to make the transition despite the considerable technical debt?

When asked on Threads what inspired the change, I responded with this:

Over the last year or so they’ve made changes that took features away from paying customers, and added features to the free plan that paying customers STILL have to pay for.

Just feels like they’re not interested in helping small business owners anymore.

I like Notion because it’s flexible, used by a lot of people, and has been adding great features (like automations).

I also feel like I know what I’m paying for, and when I’m paying, when I pay for Notion.

And while that’s mostly the case, there are a couple of other reasons.

For one, I find myself spending most of my time in Notion these days. I’ve already moved a bunch of my operations there, and people I work regularly with, like RSS.com, and my assistant, Jordan, already work in Notion.

I’ve also moved family stuff into Notion, and it was very easy to share that stuff with my wife.

When I do open Airtable, it now feels cumbersome. I can’t view everything I need to view in one spot (even with interfaces), and it’s slow.

But, while this certainly feels like a major move (that I still need to make the checklists for), it’s actually a smaller part of bigger changes I’m making moving into 2024.

See, my entire tech stack is changing. Here are the switches I’m making:

1. Organization and Ops: Airtable to Notion
2. Podcast Recording: Riverside to Squadcast
3. Projects/Task Management: Todoist to Things 3
4. Scheduling: Calendly to SavvyCal (probably, in this case)

I’ll likely write about this in greater detail in future articles, but taking out task manager (which I feel like I change a little too often), I’m moving to Squadcast because it’s now including with my Descript subscription, and I’m displeased with the direction Riverside is going in.

And the switch to SavvyCal is related — they have very tight integration with Squadcast, which is one of the most important parts of my guest-booking workflow.

Of-course, all of this requires considerable changes — so why now?

It’s a combination of cost-savings and frustration. I’ve been increasingly frustrated with Airtable, which is what pushed me to test Notion in the first place.

I don’t like how much I’m paying for Airtable, and like even less that they seem to be taking more features away from the plan I’m paying for.

Couple that with the fact that Notion is more affordable, even with full-access guests, and that they just rolled out their own Automations, and it felt like a good time to jump.

All of the moves will save me $450 annually, and will end up saving me time too. Not bad.

So when do you burn it all down and start over?

I think it’s when the frustrations start getting in the way of you working efficiently.

If what you have is working, and you can continue to afford the tools you use, leave them be.

But if your processes suddenly start fighting you, or there’s a consolidation of tools (like with Descript/Squadcast), you should consider changing.

It’s also worth noting that you’re likely not rebuilding your entire process stack like I am. But if you are switching a couple of things all at the same time, you likely don’t have to repeat some of that switch work.

For example, Moving from Airtable to Notion will requirement me to update my Guest onboarding automation anyway — so I’ll be able to update it both for Notion and SavvyCal.

If you’re worried about the level of effort — well don’t worry. I’ll be documenting that for you 🙂