For some reason, "working for yourself" or "being your own boss" is a fantasy for many people.

People use this fantasy to sell the idea of starting a business. Be your own boss! Answer to nobody! Work on your own terms! And so on.

The fantasy of "being your own boss" exists because people contrast it with working for someone they don't like. Or with working at all.

The allure of working for yourself is that you only work as hard as you want to, on things you want to work on, and you get one hundred percent of the benefit.

Oh, and also, you're your own boss, which means you're the best boss ever. Right? Well... not always. Because there are three aspects of working for yourself that are ironically quite annoying.

These are the following:

  • Being your own boss means being your own employee
  • You're also the president of your own board
  • You are your own principal (and usually only) investor

Being Your Own Boss Also Means Being Your Own Employee

I love being my own boss, because it means I have no boss. But I hate being anyone's employee. Including being my own employee!

As I once told my last boss... I don't think I'm a very good employee. I don't like taking instructions, I don't like doing things in any way but my way, and I sometimes just don't like doing anything at all. That's why I quit to do my own thing, and at most to be a consultant who can quit at any time.

Being a "boss" (which I used to be, and which I sometimes still kind-of am, when consulting) means I have to lay out visions, plan usage of resources, and hire and fire.

I also have to deal with minutiae like a staff member not showing up, or one who wants to take naps, knock off early, or just not do any work.

Unfortunately, being my own boss, means I have to manage myself when I'm being a lousy employee.

Just as I've been in the past, when I work for myself, I'm rebellious for no reason, I don't like working too hard, I take breaks too often, and I fail to execute on plans until the last minute (or until it's too late).

Often, as my own boss, I know what I should be doing. But as an employee, I prefer to do other things.

Basically, it's fun being the boss, unless I have to manage myself!

You're Also the President of Your Own Board

Being my own boss — and not having any investors — means I'm also the president of my own board.

I only know conceptually what a board does, from other board members I know. To me, the high-level summary (which is what they revel in, these board types) is that it seems like they sit around approving budgets and strategic plans, and basically taking in money for seeming wise. (Sounds fun!)

But one important thing I know a board does is approve CEOs, or recommend that they be dismissed.

As president of my own board, I have to constantly ask myself: Am I really the best person to be running this company?

Who came up with this plan? Isn't it time the CEO came up with a new one? And excuse me, but have we ever had a budget?

What is the CEO actually doing??

And frankly, that's a hard question to answer. On the one hand, nobody is as invested as I am, so I'd be the ideal CEO. On the other, I can definitely think of people I'd rather be the CEO of my company. If only I could afford them!

You Are Your Own Primary Investor

Finally, as well as being my own employee and my own president, I'm also my own investor. And usually the only one.

So as my own principal investor, I look at the things I, the CEO, am doing, and think: Wait, is this really where I, the investor, should be dumping my money?

Rather than build websites and apps, should I just

  • Buy a house in a fast-growing city an let it out as an Airbnb?
  • Buy a Bitcoin, at one of the times when it's cheap?
  • Start a consulting company of some kind?
  • Go get a job, you lazy bum?

Frankly, all those sound like good ideas. I don't really know. We tend to tell life stories retrospectively. I can't predict the future. And that's maybe why I should fire myself as CEO. (...Do you want the job?)

There are Definitely Upsides to Being Your Own Boss

This is all ignoring the many, many upsides of being my own boss.

I chose the business I'm in — digital media and apps — specifically because it suits my needs. It's 100% flexible with regard to time and location, and it doesn't require any interaction with clients, customers, or suppliers.

I get to write. I love writing. And people write in to me, and say "thanks". There's absolutely nothing better than that. (Feel free to do so, if you like.)

You might choose the business you're in for totally different reasons. Maybe you want to employ people, maybe physical products give you joy, or maybe there's a particular industry you want to serve.

Being able to choose exactly what you want to do — presuming there's a market for it — is the reason we become our own boss.

Just don't fool yourself that it's everything you may imagine it to be.