Employment vs. Self-employment

I had it made. I was running a comfortably profitable low-six-figure revenue company, and I answered to nobody but myself and customers. Growth wasn’t explosive, but business was healthy, and financially, I was doing well. So why leave it all behind?

That answer is, of course, complicated. The short answer is that after three years of medical issues, I didn’t have enough left in the tank to keep on trucking. Without any alternatives, I could have probably dug deep once more, but I decided to consider the inconsiderable: working for someone else.

Now, if you compare self-employment to working for a huge corporation, taking a 9-to-5 job is going to be a tougher sell. If, however, you compare self-employment to joining a smaller business to play a larger role, the gap isn’t so wide.

If you’re suffocated by bureaucracy and red tape at large corporations, starting a business won’t help. It will merely change the kind of bureaucracy that you deal with since, as a founder, you’ll still be responsible for business operations.

If you hate the idea of commuting to a large corporate office and working a cubicle, you can just as easily join a company that embraces remote work.

If you feel like your management is incompetent or otherwise making decisions that you deeply disagree with, starting a business can help, but working with a smaller team that more closely aligns with your values solves that just as well.

If you want to spend more time on projects that you’re passionate about instead of working only on projects to which you are assigned, self-employment won’t have a huge impact either. When you’re the boss, there are countless projects that you have to work on whether you like them or not.

If you want to work more reasonable hours, self-employment may or may not help. That will entirely be a function of how much pressure you put on yourself. Some founders have no problem working 10-30 hours per week and feeling great, but others feel they have to work 80 hour weeks. No matter how many hours you work, there’s always more to be done.

If you don’t trust your company to look after your interests, self-employment is a good bet, but there are also plenty of companies that do genuinely look after their employees. Job stability isn’t a function of the size of the company. It’s a function of how much the people running the company care about the team that supports the company.

Now, if you want to become a multi-zillionaire or be the owner of a company with its name on a building, the chances are that self-employment is your best bet, but you may discover that these aren’t great long-term motivators by themselves. It’s difficult to build a sustainable business if you only care about the superficial aspects of business.

Being self-employed is great. And it’s not so great. Like anything, there are tradeoffs. For you, the tradeoffs may be worth it. Or, they might not. Or, they may not be the right tradeoffs at this point in your life. Just don’t put self-employment on a pedestal. There are plenty of other options that are darn near self-employment without the burdens.

Having been out of the self-employment game for over a year now, I can quantifiably say that I’m happier in every way. Occasionally there’s an itch reminding me that I learned so much the first time around that I could do so much better and make a whole new set of mistakes if I tried again, but I know better. Working with a great team on products I care about is priceless.

Regardless, choose carefully, and don’t pursue self-employment for self-employment’s sake. Pursue self-employment when, no matter what you do, you can no longer silence that voice telling you to get out and create something.