Life is pretty good at building prison cells around us without us even noticing.
Think about it. You pick a major in high school or university, and suddenly you’re locked into a path. Switch from literature to physics? Good luck, you’re basically starting from scratch. That’s one wall up.
Then in your 20s, you get a mortgage. Now you need to earn enough to pay it back every month, plus all the other stuff you’ve accumulated: car payments, furniture, subscriptions. The freedom to quit your job and chase something else? Gone. Another wall up.
You land a good job with promotion potential. Stick around and you’ll climb the ladder, make more money, get that nice title. But it comes with constraints: 9-to-5 hours (or worse), limited vacation days that need approval, maybe even asking permission for a bathroom break. You lose the independence to design your own schedule. Another wall up.
Then there’s family, friends, and what everyone expects from you. Marriage, kids, the white picket fence. All meaningful commitments, but they lock you in place. Fourth wall up.
Now you’re standing in a room between those four walls. And here’s the thing, it’s incredibly hard to escape because you have real commitments you need to honor. You’ve trapped yourself with your own lifestyle.
So what do people do? They think about breaking free. “If I start my own business, I’ll work when I want, design my own schedule.” That’s one wall down, right? “And if I do well, I’ll make real money without waiting for promotions. Maybe my partner could even stop working.” Another wall down.
Sounds good. But here’s what nobody tells you.
Most people just build themselves a new prison.
They escape the corporate cage and manually construct another one, placing each brick without even realizing it.
What a Prison Business Looks Like
So people decide to escape by starting their own business. Finally, freedom! Except... here’s what actually happens.
I actually lived this as a freelance web designer early on. Build a site, get paid, then immediately start hunting for the next client. No client? No paycheck. Want to take a week off? No paycheck. I gave up quickly because I didn’t know how to find clients, but honestly, even if I’d figured that out, I’d still be on the hamster wheel.
That’s a prison business. Here are more examples:
The brick-and-mortar trap: You open your dream store or studio. Sounds great until you realize you need to be there when customers show up. You can’t take a vacation unless you hire employees and delegate everything, which many people never get to. You’re tied to a location and a schedule, sometimes with a loan hanging over your head from day one.
The time-for-money trap: Many yoga teachers only get paid when they teach. In an industry that doesn’t pay super well, you end up working a ton just to sustain your lifestyle. Taking time off? That’s lost income you probably can’t afford.
The endless acquisition trap: Whether in-person or online, some businesses require you to constantly find new clients to make sales. It’s exhausting. You’re always hustling, always convincing, always chasing the next person through the door.
Here’s the brutal truth: you traded one boss for twenty bosses, your clients now dictate your schedule.
But Wait, Is a Prison Business Bad?
Not necessarily. If you’ve always dreamed of owning a flower shop or teaching yoga, go for it. Do something you enjoy, something that brings you fulfillment. You’ll gain stress, sure, but you’ll also gain purpose. You won’t have regrets down the line.
Just don’t expect it to make you more free than a regular employee job. Be honest with yourself about what you’re chasing: passion, freedom, or both.
What a Freedom Business Looks Like
A freedom business might feel like a prison at the beginning. Most of the time when you start, you need to hustle and grind and put in the hours anyway. The difference is in the design.
A freedom business is one where:
You can make more money without working more hours
Your pricing model lets you make a good living without working 60-hour weeks
You have flexibility to design your schedule because the nature of the work allows it
Your expenses stay flat as you grow (serving 8 clients doesn’t cost more than serving 2 because you’re already paying for the tools anyway, your profit margins increase as you scale)
Here are some examples:
Digital products: Create an online course once, sell it repeatedly. The work is upfront, but once it’s built, each new customer doesn’t require more of your time.
Membership communities: Monthly subscriptions for access to content, resources, or live events. Recurring revenue with mostly asynchronous delivery.
AI-powered SaaS: With the rise of AI, more solopreneurs are creating tools people pay monthly subscriptions to use. Build it once, serve thousands.
Premium positioning: A friend of mine, the first business coach Rosie and I hired, now charges tens of thousands of dollars to work with him (lucky us, we worked with him when he was getting started and paid much less!). His track record allows him to charge premium rates, which means he doesn’t have to chase new clients every month.
Content platforms: Building a YouTube channel is a long game, but it can generate nice revenue for “just” filming videos. Plus, once you’ve grown an audience, you can create new products for them.
My on-demand yoga platform and online yoga school gave me real independence. I traveled through 15 countries while running them. The work was mostly asynchronous, maybe 30% live calls, 70% on my own time. That wasn’t luck. I designed it that way from the start.
I’ve tried plenty of other things: blogging (great model, couldn’t stick with it), a t-shirt brand (too saturated, lacked the marketing chops), a podcast with 120+ episodes (tons of freedom but couldn’t scale it). The pattern? I kept trying models that offered freedom, even when I failed at execution. Better to fail at something designed for freedom than succeed at building your own cage.
When those projects didn’t work out, I could pivot quickly because I wasn’t trapped. That’s the advantage of designing for freedom even when you’re still learning execution.
Questions to Ask Yourself
These questions will tell you everything you need to know about whether you’re building freedom or a cage:
If you’re thinking about starting a business:
Can I eventually detach my income from the hours I work?
Will clients need this once, or repeatedly? (Repeat customers = higher lifetime value)
Can I deliver this with schedule and location freedom?
What can I delegate to buy back my time?
If you’re already running a business:
Can I work when I want, or do my clients dictate my schedule?
If I don’t work, am I still making money?
If I stop marketing, how fast does my income hit zero?
How many clients do I need weekly to hit my income goal? Is that number realistic?
These answers show you exactly where you are. From there, you can work on solutions: change your delivery model, adjust your pricing so you need fewer clients to make the same money, create boundaries around your availability, delegate strategically.
For Those Still in Corporate
Don’t jump at the first shiny opportunity. Ask the right questions from the start. Get educated: read books, listen to podcasts, read this newsletter 😉. Many entrepreneurs made these mistakes and talked about it. Use their experiences.
Now my websites run on a model that keeps clients long-term instead of constant acquisition. My coaching and consulting mix live calls with asynchronous work. I specialized and niched down so my pricing means I don’t need 30 clients to make it work. Each decision was intentional, not because I’m smarter, but because I learned what prison feels like.
The Bottom Line
If you’re chasing passion and don’t care about more freedom? Go for it. Being miserable at work is... miserable. You need to do something you enjoy, something that brings you fulfillment. You’ll gain stress, but in the long run it’ll be worth it.
But if you’re chasing freedom? Be intentional about how you design your business from day one.
Don’t just escape one prison to build another. Design your freedom from day one, even if it takes a few tries to get the execution right.
If you’re reading this and realizing you might be building (or already stuck in) a prison business, or you’re not sure how to design for freedom from the start, let’s talk. I help people get clarity on exactly these kinds of decisions.
What are your thoughts? Are you designing for freedom or accidentally building a cage? Hit reply, I read every response.