Working for yourself is not freedom.

The myth of the entrepreneurial good life.

Talking to some of the founders I’ve met over the past six months, I’ve encountered an overwhelming majority who want to found businesses to achieve freedom and a work-life balance. Their idea is that if they became their own boss, life would be a lot easier. It’d be simpler. It’d be more relaxing.

I can see the appeal in this. It’s a lifestyle that gets pushed around a lot by entrepreneurs who post photos on Instagram captioned “today’s office” — and it’s always a beach in Thailand.

In my experience, entrepreneurship is not like that. It’s not an easy, free lifestyle. It’s the furthest thing from being low pressure. And you do not give up having a total asshole for a boss. Just doesn’t happen. Because working for yourself is the hardest career you could ever choose.

If you’re successful, and you grow your business to the right size, and you dedicate years of your life to slogging through the shit, you can reach freedom and happiness. You can sit on a beach with your laptop and have a care-free life. But it takes a long time.

And if you’re building a startup because you want a work-life balance and total freedom and hours of R&R time, I have some bad news. You’re not going to make it.


Let’s start with the money.

When you work most other jobs, you work for a paycheck. You can sit down at the start of the month and write out a budget, everything you’re going to do with your cash. You have a pretty decent idea of what you’ll be paid, and you can make some decisions around that.

If you work X number of hours, you’ll be paid Y. It’s an easy equation. It’s a million miles away from entrepreneurship. Because when you start your own business, and you’re relying on it for your main source of income, that equation becomes a lot more complicated.

If you’re bootstrapping, you’re staring at a CRM, working out how much money is in the pipeline, which deals you can close, and what your business’ cashflow looks like. You’re matching that against your bottom line. And then you’re trying to guess the safest amount that you can withdraw to pay for your lifestyle.

That’s what I do at my consulting company and at Creatomic.

In the beginning, a bootstrapped startup lives hand-to-mouth. You have to be prepared to deal with that. Which is tough, because it means your lifestyle is going to be hard to plan in advance, and your quality of living will rise and fall with your revenue. It’s unavoidable. You will need to start making good decisions about money.

At this point, you either begin to find ways to cut corners in your own life to fund your business, or cut corners in your business to fund your life. The first option is the right one, but it’s tough. The second option is the easy one. It will ruin you.

If you’re a funded startup, it’s a little different. You’re not trying to scrape together enough money for your salary, because you know where it’s going to come from. What you are trying to do is give your business enough runway, and that’s a whole other bucket of pain.

Side note. If you’re running a startup that’s taken on investors, you are no longer your own boss. You’ll find that out when you start disagreeing with the money.

I know this sounds depressing. If you want to feel good, go right ahead and skip to the end of the post. I promise it’s not all doom and gloom.


Okay, still with me? Let’s talk about time. I hear from founders who want to tell me that they’re chasing the dream of entrepreneurship because they want to take control of their time, and have a lot more of it to spare. Again, I’m sorry, but that’s not what starting a business is like.

For most people just getting a company off the ground, the number one resource that you have is time. It’s a risky asset, because you never have as much as you think, and it can disappear tomorrow. But it’s all you’ve got. In the first few years of your business, you will sink hours and hours of your time into running your company.

When you take time away, and you try to switch off, you’re going to be acutely aware of what isn’t being done. Aware of the tasks that aren’t being completed, the clients who aren’t being called, and the products that aren’t being refined. No matter how hard you try to shut your mind down, it will rarely happen.

Since it’s the one resource you can keep pumping in, no matter how low the money gets, you are going to constantly worry that you aren’t giving enough.

Seriously, keep scrolling and I’ll make you feel better about your life choices. I’m almost done.


Haven’t given up yet? Awesome. There’s one more thing. That “be-your-own-boss” thing. If you think that being your own boss is going to be nicer than working for someone else, you will be sorely disappointed.

Everyone who’s worked for someone else has encountered one of two types of bad bosses at some point in their lives.

  1. The asshole boss. You know the kind. They wait by the elevator with a clipboard and mark the time you get into the office. They dump a bunch of papers on your desk at 5:00 on a Friday arvo. They don’t give you a pay rise or a promotion and they never remember your birthday.
  2. The boss who doesn’t give a shit. They don’t challenge you, they let you turn up late, they never give you quality feedback, and you never learn anything. Most of the time, you feel like they wouldn’t particularly care if you came into work at all. Which in turn, makes you feel like your job doesn’t matter.

You’re about to become one of those two types of bosses. When you work for yourself, there’s no middle ground between them. You’ll either give yourself way too much slack, and never have any control, or you’ll hound and pound yourself to the point of insanity.

You will learn to treat yourself in a way that you would never treat your staff. You will yell at yourself and criticize yourself to such an extreme that it would be grounds for a harassment law suit from anyone else. When I first started my communications firm, I would catch myself whispering in my own head about how close to failure I was.

It’s not healthy, and it’s not a good thing, but more than anyone else at your startup, you will be aware of the crushing pressure and the ticking clock and the need to stay afloat. The rest of the team? They’re turning up to their jobs. You’re putting your life on the line.


If you’ve battled through all that and you’re still reading, congratulations. I have some good news for you. No matter how hard it is, being an entrepreneur is worth it. Founding your own business is worth it. Growing a startup is worth it. You have the opportunity to build something incredible, something unique that could only have come from you.

You have the opportunity to charge of your own career and take responsibility for your destiny. No amount of failure or hard work or tough times can take that away from you. When you’re making something for yourself — trust me, it feels a lot better than making it for someone else.

I’ve been on this ride for a long time, and I don’t regret it. I could do anything else, and I’d still choose to be an entrepreneur, to work every day trying to grow my businesses and build.

If you go into entrepreneurship fully understanding that it’s going to be difficult, that it’s going to take years of your own time and a lot of late nights, that it’s the hardest thing you’ll ever do, you are going to be okay. You can embrace the tough parts of it and appreciate the good.

And maybe, just maybe, if you get far enough and you work hard enough, you can end up on a beach with a laptop, drinking cocktails and running your business the way you want.

But if you go in there thinking that you’re about to get your dream lifestyle out of the gates and live free, there’s a rude awakening around the corner.


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Jon Westenberg has appeared and published in Business Insider, Inc.com, TIME and dozens of other publications, talking about startup entrepreneurship, writing and innovation. Jon has helped hundreds of businesses worldwide grow their audience and take control of their future. Jon is an investor, an entrepreneur and a digital publisher. He is the founder of Creatomic, a globally recognized communications firm.

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