You Can Never Really Be Your Own Boss (And That’s a Good Thing)

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“It must be great to be your own boss!” Over the last few months, as the Pangea Marketing Agency has taken off faster than I expected, I’ve heard this sentence more than I ever expected. Don’t get me wrong – it’s incredibly flattering and I respond with polite confirmations. You know the sort: “yes, it’s pretty great, I’m very fortunate!” And, yes, indeed, I really am very fortunate.

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What goes unseen is that I’m juggling a full-time day job, the marketing agency, and board game projects like Tasty Humans. I’ve had a wide variety of work experiences and I have to tell you something I’ve found out.

You can never really be your own boss.

Obviously, putting a sentence like that in bold, you know I’m not about to give you a Tony Robbins style speech. No, I’m here to shatter myths like my name’s Adam Savage. I’m here to set expectations sensibly so you can live a life of relative comfort while you strive to become your best self. It’s true, I’m a big fan of self-starting and hard work, but I’m not a fan of false prosperity gospel.

So let’s put to bed this “be your own boss” cliche that I hear all the time online and offline.

Even Corporate CEOs Have Bosses

Let’s say you’re a yuppie in the 1980s. You smoke in your office and wear suspenders and stripes. At the age of 27, after working 90 hours a week for years on end in a high finance firm, you earn a VP title. You’re on track to become the CEO of JP Chase Fargo.

Cut to 2007 where you’re testing the strings on your golden parachute. Yeah, you made it to the CEO position, but you never became your own boss. No, indeed, the Board of Directors tells you what to do all the time.

You consider angling for the Chairman of the Board position, but she seems miserable. She’s reporting to all the shareholders and doesn’t really have many viable strategic options either. She’s at their mercy.

You’ve kicked around the idea of buying a 51% stake in the company, but even then, you’d still be subject to the whims of the market. Everybody’s a part of the market, so this abstract thing that would rule your life and limit your actions has no face. You can’t call anyone out or bargain with it.

All this is to say that no matter how high up you get in a traditional company, you’re always reporting to somebody or something. This isn’t a bad thing, and I’ll explain this later.

Want to Be Your Own Boss? Don’t Become an Entrepreneur!

“Be your own boss doesn’t mean becoming the CEO of JP Chase Fargo, Brandon.” Okay, and I get that. As a member of the millennial generation that wants to become entrepreneurs because of the misdeeds of the CEOs of JP Chase Fargo, I can relate. However, I can tell you from firsthand experience that entrepreneurs are not their own bosses either.

Entrepreneurs report to their clients. If they don’t have clients, they report to their customers. If they never deal with their customers directly, they report to market demand. Their viable money-making options are limited by the iron law of product-market fit.

Even if you found a way around the inexorable law of product-market fit, you’d still have some bosses. Among my many bosses includes the Tennessee Department of Revenue, and for that matter, the Internal Revenue Service. I have to play nice by the rules of my local city as well as Hamilton County, Tennessee. Even in my own business, I report to bureaucrats at various different levels of the government. And Tennessee, true to Southern tradition, plays it pretty fast and loose on laws and regulations.

Again, this is not a bad thing. It’s simply something you must accept.

Even World Leaders Have a Boss

“Okay smart guy, but what if I become the government?” Sure, let’s run with this idea. Even politicians cannot act with impunity. They have to win over a coalition of voters. Donald Trump may be the President of the United States, but he also has a boss. Multiple, in fact. Their names are Wisconsin, Michigan, Ohio, Pennsylvania, and Florida.

Even if you’re a dictator, like Kim Jong Un, you have a boss, too. You see, being dictator comes with a lot of perks, so you have to have people protect you or else you will be overthrown. In this sense, Kim Jong Un’s bosses are any generals or other key government personnel who prevent a coup. This is not just my personal belief. This is, in fact, a studied and published fact in political science. Here’s a reputable, if insouciant, pop-sci book that does a good job of explaining it.

You Can Never Escape Accountability…But That’s Actually a Good Thing

The key takeaway here is that you can never escape accountability. All human begins are connected. We are in the world together for better or for worse. For that reason, it’s really important to build connections and try to help people.

Look, I know working for someone is hard. Sometimes you don’t know what they want. Sometimes they are unreasonable. Other times, they are outright mean. Bad bosses outnumber good bosses by a ratio of like 10:1. Indeed, it’s my hope that I’m not among the 10 for my interns and contractors.

In most situations, though, you can find a way to finesse it. You can find a way to live and work well. A few exceptions, of course, are when communication breaks down to an irreparable level and gross indecency of the type that I’d prefer not to spell out.

You Don’t Want to Be Your Own Boss…You Actually Want Purpose, Self-Expression, and the Ability to Control Your Work

It’s no secret that most people hate their jobs. Again, this is not a Brandonism – about a third of people would call themselves “engaged at work” according to Gallup. So what actually makes a difference? According to Harvard Business Review, it comes down to three basic qualities: purpose, self-expression, and experimentation.

When people want to “be their own boss,” it’s a cry that they feel out of control. They don’t feel like their work matters, our their voice matters, or that they have any say. Seriously, if you have a desire to be your own boss, keep asking “why” until you get to the root of the desire. It will probably be some variation of these three things.

People need to feel like their life has a purpose. To constantly repress your true desires is to suffer. The ability to experiment at work, to my ears, sounds like freedom from micromanagement and the ability to choose your own path.

Not every job will offer you the ability to pursue these three things. Not everyone will have the privilege to chase one that does either. If you’re stuck in a job you hate, I’m here to say that running away may or may not actually fix your problems. You have to do the hard work of introspection!

And let me say just one more thing. There is dignity in any work you do, including the act of looking for work. You don’t have to be your own boss to live well. You don’t have to have a flashy job to make a difference.

Final Thoughts

We are all connected. Everyone’s actions affect other people. We live in a world where no one can truly be their own boss. This is a good thing – it means we have to play nice with one another!

When you say to yourself “I want to be my own boss,” I want you to challenge that statement. Ask “why?” Keep asking until you get to the emotional root of your desires. It when you reach the roots that you can see what you really want. This gives you the freedom to chase what you truly desire 🙂

One thought on “You Can Never Really Be Your Own Boss (And That’s a Good Thing)

  1. So true!! As someone who went from the corporate world to working as an independent contractor, I’m surprised by what I miss about my former job. For example, I used to hate the office and look at it as a prison, but now I look back and miss the the constant camaraderie – the great conversations, laughs and commiseration you get just by being around other people. Being an independent contractor or ‘your own boss’ is like being a lone wolf, and you have to work hard to re-establish that sense of community. The other thing is I miss is having someone else to help spot-check you – whether it’s giving feedback to an email or helping you brainstorm new ideas. Being your own boss comes with its own advantages and disadvantages, and you just have to keep in mind that the grass is always greener on the other side.

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