Debunking fears of self-employment (Part 1)

There are a lot of people who might want to start their own business, but it sounds too scary. I can relate to this. I think it’s important to examine some of these fears and figure out a new way of thinking about them.

For example:

  • Being self-employed is too risky.
  • Being self-employed (in America) makes it too hard to get health insurance.
  • Being self-employed causes you to make less money than you would make working for a company.

Let’s look at these assumptions…

Self-employment is Too Risky.

It’s true that if you’re self-employed, you don’t have a steady paycheck. Every dollar you make has to come from the sweat of your brow; it’s not like working for a company where it’s possible to just coast for a while without working too hard, and then on payday you collect your full paycheck like every other week.

However, especially in “this economy,” working for someone else is pretty risky, too.

After all, if you work for a company, you can get laid off. At any time. Often for reasons that have nothing to do with whether or not you’re good at your job.

Worst of all, if you spend too long at one employer, you run the risk of your skills becoming stagnant. There’s nothing worse, especially in the fast-paced information economy that we are living in now, than to be stuck with obsolete skills and a mindset of inertia and helplessness. If you spend 30 years working for a company and then get laid off at age 55, and all you know is an increasingly narrow band of knowledge that only applies to what goes on at your specific (former) company…well, that’s a terribly difficult spot to be in.

Which risk would you rather take? The risk of trying to do something you care about and working for yourself (and possibly failing and losing your house), or the risk of “playing it safe” by working for one employer (and possibly ending up with less money, less fun, less worthwhile experience…and still being stranded at age 55 with few marketable skills, and still losing your house)?

I’m 30 years old. In the past year, two of my high school classmates died. (One after a lifelong struggle with cystic fibrosis, the other from a sudden-onset infection of antibiotic-resistant pneumonia.) The point of mentioning this is – life is unpredictable. There are no guarantees in this world. Why do you want to spend your life doing something you hate, only to drop dead at your desk three days before retirement?

Sometimes the riskiest move is to keep playing it safe.


  1. You are dead on with this post. The extend of social conditioning goes far deeper than I realized. I made the very same mistakes you are talking about, I stayed at one company far too long, which has resulted in stagnation of my skills and missing out on the new technologies and trends. People want proven experience even for low paying freelance jobs.

    For the IT industry, if you work at a large corporate environment, it is inevitable to get stuck in a narrow focused niche, not learning any new skills and becoming obsolete in the fast paced tech world. By the time you get laid off, your skillset will not be enough to qualify for a lot of jobs (including freelance and consulting gigs). People who work at startup environments or smaller shops where they do everything are better off. Corporate cubicle is like disease that kills you slowly.