scorecardYes, it can suck to work for 'The Man.' But so can working for yourself!
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Yes, it can suck to work for 'The Man.' But so can working for yourself!

Henry Blodget   

Yes, it can suck to work for 'The Man.' But so can working for yourself!
Careers3 min read
  • Some Gen Zers are so horrified by millennials' work-life that they plan to work for themselves.
  • Self-employment can be great! But it's no panacea.

I gather that some Gen Zers are so appalled by the working woes of millennials that they've sworn off working for "The Man" and, instead, plan to go into business for themselves.

That can, in fact, be an excellent career decision!

But it can also be a stressful, disappointing, and difficult one — and one that may be significantly less financially rewarding than working for an existing organization.

And working for yourself does not actually come with one big benefit that most people assume it does — namely, not having a boss.

We all have bosses, even CEOs, and even people who work alone, for themselves, at home.

Who are the bosses of people who work for themselves?

Their clients.

How do I know this?

I started a company, Business Insider, 16 years ago — and, before that, for many years, I worked "for myself," as a freelancer, blogger, and consultant.

And believe me, client bosses can be just as demanding and unreasonable and annoying as actual bosses — in fact, even more so.

For example, client bosses can ghost you. They can reject the work you give them and demand that you make it different or better. They can be insanely nit-picky and critical. They can demand that you work nights and weekends. They can Slack you from their yachts and insist that you slave at your desk until their job is done. They can yell at you. They can blame you for things that aren't your fault. They can promise you raises and referrals and then renege. They can even fire you — without warning or severance!

And when client-bosses do these things — and you feel you've been treated unfairly — you can't go to HR for help. Because when you work for yourself, there is no HR.

Serial founder Elon Musk once described starting a company as "eating glass and staring into the abyss" — a quote he said he borrowed from a friend.

Nvidia founder and CEO Jensen Huang recently said he wouldn't start a company again, if he had to do it over.

"At that time, if we realized the pain and suffering and just how vulnerable you're going to feel, and the challenges that you're going to endure, the embarrassment and the shame, the list of all the things that go wrong, I don't think anybody would start a company," he said. "Nobody in their right mind would do it."

(I respectfully disagree with just how categorical Elon and Jensen are here: Starting a company is indeed hard, but it can also exhilarating and fun.)

Maybe you'll say, well, when I work for myself, I will not have a client-based business, because I do not want to have a boss.

For example, you might say, I will travel the world in my van and post pictures of myself on Instagram and live on the ad revenue. Then I won't have a boss!

Yes, actually, you still will have a boss. Many, in fact.

Your bosses in that case will be Instagram and its algorithm (which, unlike a human boss, you have zero control or influence over) and your fickle "followers," who, in exchange for their attention, will demand that you keep posting ever-more-fabulous and differentiated adventures, lest they shift their eyeballs to any of the millions of other people who want to avoid having bosses by traveling the world and posting pictures on Instagram.

True, your Instagram bosses won't be annoying in-person humans who insist that you be such-and-such-a-place at such-and-such-a-time and then micro-manage you and otherwise make your life miserable.

But they'll still be stress-and-anxiety provoking.

As, more generally, will be this business of going into business for yourself.

In fact, there's no better way to appreciate the joys of a steady paycheck from "The Man" than going into business for yourself.

You just show up and do enough work that you don't get fired and they pay you and maybe even give you benefits?

You don't have to compete with all the other organizations and people who do what you do, hustle for new clients, do and deliver great work, make and keep your clients happy, get your clients to pay their bills (different than making them happy), manage the concerns, lives, feelings, needs, and egos of your employees, make sure there is enough money to pay your employees and all your other expenses, and do all this while juggling your own life, feelings, and bills?

Put it that way, and working for The Man doesn't sound so bad!

This isn't to say that working for yourself can't be great. It can.

It's just to say that, unless you're lucky enough to have a big pile of savings, a trust fund, or rich parents or friends who pay for everything, it will be hard to find any work or way of working that doesn't occasionally create stress, inconvenience, annoyance, or financial concerns.

This includes both working for yourself and working for The Man.

Have work-related questions? Send them to!