Are You the Sisyphus of Business Operations?

One of my favorite lines from 30 Rock comes from Jack Donaghy: “I’m the Sisyphus of Reaganing.”

If you know the reference, it’s brilliant. Sisyphus was condemned to push a boulder up a hill for eternity, only to watch it roll back down every time. Futile labor as punishment for his hubris.

Sound familiar?

You escaped the 9-to-5 grind with the hubris to think you could build something better. But now you’re trapped in your own version of eternal punishment:

• Every Monday, you’re back to fighting the same operational fires you “solved” last week
• You keep manually doing tasks you swear you’ll automate “when you have time”
• Your team asks the same questions over and over because nothing is documented
• You work weekends to catch up on the work you couldn’t finish during your week of interruptions
• You check email at your kid’s soccer game because you’re terrified something will fall apart

The boulder keeps rolling back down.

Unlike Sisyphus, You’re Not Actually Cursed

Here’s the good news: You didn’t anger Zeus. Your situation isn’t permanent cosmic punishment.

Your problem is completely fixable—you just need to know what to fix and how to break the cycle.

The way I see it, you can “get the boulder to the top of the hill” through 3 fixes:

1. Documentation Having SOPs means you’re not reinventing the wheel or struggling to perform routine tasks every single time.
2. Automation For repetitive tasks, you can make the machines work for you, ensuring your business keeps moving even when you’re not at your desk.
3. Delegation You don’t need to do everything for your business, nor should you. But you need systems that make delegation actually work.

I call it the D.A.D. framework.

When you have these 3 things in place, everything becomes clearer. You know what to prioritize. You can spend your time wisely.

As a result, you’re not constantly putting out fires, working long hours, or checking your email at the playground.

The boulder stays at the top of the hill.

But Here’s the Problem Most Business Owners Face

You know you need documentation, automation, and delegation. Everyone tells you that.

But it’s hard to know:

• Where you’re struggling the most
• What you should work on first
• Which tools actually solve your specific problems
• How to implement any of this without making your current chaos worse

That’s where most people get stuck. They start a documentation project, get overwhelmed, and abandon it when client work gets busy.

Or they buy an automation tool that sits unused because they don’t know how to set it up properly.

You need expert guidance, not another generic productivity course.

Introducing: The Control Room

You’re stuck pushing boulders… what you need is mission control for your business operations.

Here’s how it works:

Submit questions anytime via video, audio, or text about any business process, tool integration, or workflow challenge. Get expert responses within 48 hours with specific recommendations for your situation.

No appointments to schedule. No waiting weeks for availability. Just ongoing access to systems expertise when you need it.

What you get

• Documentation Templates: Stop starting from scratch—get proven frameworks for documenting your processes.
• Automation Roadmaps: Step-by-step guidance for connecting your tools and eliminating manual work.
• Delegation Systems: How to hand off work confidently without it coming back wrong.
• Tech Stack Strategy: Which tools to use (and which to dump) for your specific business.
• Troubleshooting Support: When something breaks, get expert help to fix it.
• Accountability: Keep your systems projects moving forward.

Why this works

I’ve spent 20+ years building systems that actually work. I’ve helped dozens of business owners break their Sisyphus cycle and build operations that run smoothly without constant oversight.

More importantly: I’ve lived this. I know what it’s like to feel trapped by your own business. I had a panic attack when I couldn’t balance business and family life.

And I know exactly how to build your way out.

About Me (Joe Casabona)

I’m Joe Casabona, a systems and automations coach helping overwhelmed solopreneur parents save time and create more space in their lives.

With over two decades of experience in web development, teaching, and podcasting, I know how to streamline the chaos of running a business while balancing family life.

I’m lucky that I have the technical skills. But I also had to learn, because in 2020 I had a panic attack.

I was struggling to balance running a business during the pandemic and raising 2 kids, while my wife was working even more hours as a nurse in an ICU.

One day it got to me. I was sitting on the floor of my kitchen, crying. That’s when my 3 year old came over to me with a bottle of water and told me, “It’s OK daddy. Everything’s going to be OK.”

I felt broken. Like I failed as a dad. And I made a promise to never let it happen again.

So I decided to finally hire a VA. Build more automations. Take anything I didn’t personally have to do off my plate.

A year later, we welcomed our 3rd child into the world, and I took 6 weeks off for paternity leave…and my business was fine.

I know what you’re probably thinking here: “Well, that’s great for you. I don’t have a tech background.”

But my experience from the development and teaching worlds give me the unique perspective to teach you how to add these systems without feeling completely lost.

Get a Front Row Seat to How I Work

No matter where you’re stuck, I’ll help you get back on track. On top of support, accountability, templates, and tech stack, you’ll get a behind the scenes look at how I work and build systems.

I’m constantly trying to things to see what works and what does. I’m always building new automations and trying new tools. Those things take time — but it doesn’t have to be yours.

I’ll share everything I’m learning and building with you as part of the Control Room.

• He’s been involved at all levels. 10/10 recommend.

  Joe has been incredibly helpful to work with. He helped me transition from hosting one podcast to taking over another one, how to integrate both shows together, and how to maintain both audiences. Joe also bring a wealth of knowledge about the podcast industry in general. It seems like he’s been involved at all levels. 10/10 recommend.

  Colter Bloxom

  Relationship Advice Podcast

Get started for $99/month

Normally, this level of support costs $600+/month. But because this doesn’t require any live calls, I can deliver all of the benefits of personalized support at a fraction of the cost.

If you’re ready for…

• Clarity on your biggest roadblocks
• Proven strategies to save time and scale your business
• Expert guidance from a long-time podcaster and automator
• Accountability to see your plans through

… all on your schedule, you need the Control Room.

• His expertise is invaluable…

  From the get-go, Joe pinpointed areas for improvement and provided actionable advice that will undoubtedly streamline my workflow. His expertise is invaluable, and I’m confident that the investment in his coaching will save me both time and money in the long run. If you’re serious about taking your podcast to the next level, Joe is the coach you need!

  Laura Brazan

  Grandparents Raising Grandchildren

Ready to Take Control of Your Business Operations? Join The Control Room

Stop pushing the same operational boulder up the hill every day. Get the expert guidance you need to build systems that actually stick.

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