You’re Going to be Self-Employed Anyway

I was born in 1981; as of this writing I am 28 years old. So I know nothing of this world, but I’m told that employment used to look like this:

  • You paid attention in high school so you could go to a good college.

  • You went to a good college so that you could get a good job.
  • You picked (or were picked for) a company right out of college, and started in an entry-level position.
  • You stayed with your company for another 30-40 years, moving gradually up the corporate ladder.
  • You retired at age 60, and the company provided you with a living until you died.

Like I say, I’ve never seen that. That world doesn’t exist any more. Here’s what I saw in high school:

  • Success is unrelated to attending a good college, or even to attending college at all. Bill Gates & Michael Dell were both household names when I graduated. Meanwhile my parents and all of my friends’ parents had college degrees, and most seemed to be in soul-sucking dead-end jobs. A college degree doesn’t seem to prevent a good job, but it doesn’t seem to guarantee it either.

  • So-called “entry level” jobs all require 2-3 years of experience in similar work. You can’t get into a company without having already taken the time on your own to pick up experience.
  • Entry level jobs don’t lead up the corporate ladder. Programmers stay programmers and manager stay managers. Both move from company to company, but very rarely does anyone move up.
  • Your company doesn’t pay for your retirement. The company puts some money into a 401(k), and you’re in charge of managing your own retirement. Pensions are gone.
  • You don’t stay with the same company for 30 years. In most jobs today, someone who’s been there 10 years is unusual. In fact, you’ll probably keep this job no more than 3-5 years; you’ll either be downsized, or you’ll decide to move on.

Can you really call it employment?

In this situation, it doesn’t really make sense to think of yourself as an employee of your current company — they certainly don’t feel any loyalty to you. It makes more sense to think of yourself as self-employed, on a 3-5 year contract with your current company. Be aware that in a few years, you’ll be needing to find another client. So you’ll want to make sure your skills are up to date, that you’re in touch with the job market, and that you have a good reputation in the marketplace.

Work like an athlete

There is a class of people who have been operating like this for years, so it may help you to think about professional athletes. Peyton Manning knows that he could be traded away at the end of the season, so it’s in his best interest to be as good a player as possible. He plays well for his current team because his value would be lower if he didn’t, but his concerns for his team are secondary. His primary concern is making sure that Peyton Manning looks like he’s worth several million dollars; helping his team win is the best way to ensure that.

Likewise, you never know when your company might be acquired, go bankrupt, or have a round of layoffs. If you get downsized, wouldn’t you rather be in the top round of draft picks?. So even if you’re happy with your job and don’t want to start your own business, it’s worth the effort to figure out what your presence looks like on Google, to put up a professional website for yourself, and to brand yourself on Twitter as someone competent in your field.

Resources For Further Reading
Quit Today, Pay Cash, Don’t Retire, Die Broke was one of the first books to acknowledge the change in employment that’s been taking place, and to provide concrete recommendations for adjusting to it. Stephan Pollan assumes that you will remain as an employee, so this is an excellent book for someone who is interested in sticking with E-quadrant monetization.

Rich Dad, Poor Dad Robert Kiyosaki (or perhaps more accurately, his “Rich Dad”) observed the same phenomena as Stephan Pollan, but recommends a different approach to it: since working for a corporation is no longer secure, why don’t you own a corporation? His writing is certainly on the lower end of average, and I grade him D on “clear communication”, but he does explain a point of view that’s critical to understand if you wish to monetize yourself without a job. Rich Dad, Poor Dad Book Review


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  • What a great post, and particularly prescient at this moment in my life, where we’re moving across the country and trying to figure out how we’re going to make ends meet when we get there.

    Thanks, as always, for your fabulous wisdom.