Independence isn't Utopia

It seems that more and more people have visions of someday being self-employed. There are plenty of good reasons to pursue this, but there’s also a strong case to be made for the steady reliability of a 9-to-5 job working for someone else. Having spent eight years self-employed and now the last year working for someone else, there’s pros and cons to both sides. However, many of the reasons that people use as pros to justify self-employment aren’t the least bit valid.

There are these myths that we all tell ourselves to put self-employment on a pedestal, but only a tiny amount of them hold water. For many of these, if you’re serious about making as big of a life change as quitting your job and starting a business, there are many less drastic measures you can take with much lower risk to address some of the factors that are likely nudging you towards self-employment.

More often than not, changing jobs can be a much less drastic solution that can improve your situation much more quickly and with much less stress. Sure changing jobs is difficult, but I assure you it’s much easier than striking out on your own.

  • You hate your work/job/boss/team. Self-employment isn’t the only way to fix this. It’s possible you’ll be the worst boss you’ve ever had. (I know I was.)
  • You hate commuting. Remote work is becoming increasingly common and accepted. Alternatively, if remote work isn’t an option, finding a job closer to home is going to be much lower stress than starting a business.
  • You believe there’s a better way to do things. There’s always a better way, and there’s always other teams doing it a better way. And joining a team that’s already doing it better is a wonderful learning opportunity.
  • You want to spend more time on projects you’re passionate about. This can backfire quickly. Once you’re self-employed, it’s 100% on you to take care of business. Finding time for passion projects quickly becomes even more difficult. Once I started on Sifter, every ounce of energy I had went into Sifter. The side projects I dreamed of never materialized.
  • You want more compensation. You may feel like you’re not adequately rewarded for your contribution. You may simply want to make more money. Just realize that the path to self-employment almost invariably goes through the trough of low income. If you don’t have a healthy financial cushion or the flexibility to get through that, you’re going to end up disappointed. And your financial cushion will disappear as well.
  • You want to work fewer hours or take more time off. Unless you’re incredibly disciplined, this one is a long shot. All of the pressure is going to be on you, and every day or hour you take off is one more that you won’t be making money. Sure, at some point, you can get there, but it won’t be in those first two years. That’s not to say that it’s not possible, but it’s much easier to use vacation days at a regular job than to give yourself permission to take time off when you’re self-employed.
  • You want to have a more positive impact on the world. This one is hard. Self-employment by itself isn’t the most efficient way to do this. Working on a team that’s working on a larger project is a great way to do this. Or taking less money and working for a good cause that you believe in is another way.
  • You’re tired of bureaucracy and red tape. This is another one that can be improved by working for the right company and with the right team. Being independent doesn’t relieve you of this kind of stuff. To some degree, it increases it because things like bookkeeping, taxes, payroll, hiring/firing, and more are now entirely on you.

If you want to go out on your own, make sure it’s for reasons that can’t be fulfilled by a regular job. There are plenty of great reasons to go out on your own. For me, I spent years being fascinated and obsessed with bug and issue tracking. I started toying around with ideas as a side project with zero intention of building a business, but too many people expressed and interest and encouraged me to do more. Turning it into a business was the only logical way that it could be sustainable.

I spent eight years self-employed making a good living working on something I loved, but it took a toll. I had a successful and profitable business bringing in low-six-figure revenue every year. Now, I’m working for a company that I love. I work on products I care about. I work with tools that I love. I work from home. I take more days off. I make more money. I’m surrounded by a team of really talented people that teach me new things every day. I no longer wake up in the middle of the night to put out virtual fires. I have better health insurance. Life is genuinely better in every measurable way.

Despite all of that, I still have the itch to do my own thing. It was exciting. It was always new. There was never a dull moment. It was hard work. It was a roller coaster. I know much more now. I’d make fewer mistakes. I could self-fund it entirely. I could do a much better job the second time around. I frequently daydream and wonder about it. Much of me misses pieces of it. But more of me knows better. (For now.)

Start your own business. Don’t start your own business. Do whatever you want. Just make sure it is what you want and that you’re doing it for the right reasons. Being self-employed can be great, but it isn’t all it’s cracked up to be. I imagine someday I’ll re-join the ranks of the self-employed as well, but if I do, it will be carefully considered and under no illusions that it will be utopia.