Is it safer to work for yourself?


Safety and security are important components of anyone’s life, whether physical (we won’t be mugged or assaulted), financial (we will have enough to eat, have shelter), or any other metric.

But when it comes to less universal metrics, people’s attitudes toward safety become more personal. And one way that we can see this is in our individual attitudes toward self-employment.

Lifestyle design and self-employment

A thread that runs through many of the authors and blogs that I read is a focus on a self-directed life . Tim Ferriss, author of “The 4-Hour Workweek,” popularized what is known as “lifestyle design,” the idea that you can craft your own life in the manner that is true to you. Chris Guillebeau, author and founder of the World Domination Summit (which I’ve written about before), puts this more epigraphically right on his front page:

“You don’t have to live your life the way other people expect you to.”

This sort of thing appeals to me in spades, of course, as I think it would anyone who is interested in what the Unlikely Radical project is about. So, it would seem a necessary by-product of this is working for yourself.

Chris G., a self-employment proponent if there ever was one, draws a direct line between self-employment and security:

“What is risky? Whether you work a “real job” or strike out on your own, relying on someone else is risky.

What is secure? Creating your own freedom through side projects, independent work, instant consultancies, and creative self-employment of all kinds.”

Intellectually, I can’t argue with this argumentation. Working for someone else implies a certain level risk. You could be laid off, but are certainly at the mercy of what your employer wants to do. Whereas, when you work for yourself, no one can fire you. Sounds straightforward.

The risks of self-employment

But there is a flip side to this that seems equally compelling to me: When you work for someone else, you don’t need to worry about where the money is coming from. You go in, you do what they ask of you, and at the end of the week or two weeks or month or whatever, you are given a paycheck. Show up, do work, get paid. Rinse, repeat.

Whereas, when you work for yourself, you might be constantly searching for your next gig. There are no “vacation days” when you work for yourself. The hustle never ends. There is an immediacy and urgency to doing work that is largely absent when you work for someone else.

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Now I’m not saying that you “mail it in” when you work for someone else and only work hard when you work for yourself. But I want to acknowledge that the every day realities of working for oneself could potentially be a major source of stress. What if the sales stop rolling in? What if no one wants to buy what you’re selling? You need to figure this out. Every. Single. Day.

Jon Acuff makes this point in his excellent book “Quitter“. He makes the case that when you quit your (desk) job, you trade your one boss for lots of bosses: the boss of the mortgage, the boss of the electric bill, etc. All of those “bosses” need to be answered to, and you need to figure out how you’re going to placate them.

Your temperament makes the final call

What’s interesting to me is that whichever side you fall on the job-as-safety question appears to be informed by your own temperament and life history.

Have you had to deal with job insecurity? Have you found it difficult to hold on to a job? Have you been fired (maybe more than once, for whatever reason)? Have you had difficulty with finding a job when unemployed? If this describes your situation, then it’s not hard to see how self-employment might seem more safe and secure.

Equally though, what if you’ve been gainfully employed for years without trouble? What if you’ve had steady income and no job difficulties?  What if you’ve gone from job to job without so much as a gap? Then the safety and security gets kind of turned around. It may seem safer to not have to worry about where your next paycheck is coming from.

This is where I’ve always found myself. Intellectually I feel that self-employment is superior and less scary, but emotionally, working solely for myself fills me with a sense of terror. I’m not saying that I let that terror stop me entirely, but it’s my baseline here.

Not one or the other

Now, there are nuances to this argument. For example, if you were to build your own passive income source, you wouldn’t need to wonder where your next paycheck is coming from. And the binary nature of this argument isn’t satisfying. Why not work for someone else as well as work for yourself? Why not work part-time for a company, and then supplement that with your own work? It’s not an either/or.

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But whichever method of working that feels safer to you says more about you than some absolute ideal. There is no right answer, except the one that works for you.

But enough about me. Do you feel more secure when working for yourself or for others?

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