“It must be nice to be your own boss.” As a self-employed person, I hear this a lot. Problems: (1) it’s not true, and (2) if it were true, I would hate it.

The Feeling of Bossness

The sensation that swept over me as I walked out of my last corporate job was unforgettable. I was free. Free in a way I’d never even considered. Yes, I’d considered self-employment before, but somehow the abstract idea of self-employment never did it justice. I felt exhilarated, self-aware, vulnerable, and even a little transgressive.

Was I now, after all this time, my very own boss?

At that moment I realized that not only was I free, but I had been free all along. As I walked away from the 1970s office building to which I’d grown accustomed, it occurred to me that I should have walked away sooner.

Most Americans are brought up to believe that the key to a good life is a steady job. Before I was laid off from my last job in 2008, I had simply been negotiating life under false pretenses.

Truth: you do not need a job. It just so happens that steady employment is the most comfortable and convenient option for the risk-averse.

Free, I was. My own boss, I was not.

The Essence of Bossicitude

In typical usage, a “boss” is a malevolent dictator hired by an “organization” ostensibly to make people less happy than they might otherwise be. Witness The Googles:

1. a person in charge of a worker or organization.
“I asked my boss for a promotion”

So, friends, I ask you: when you toss off the fetters of gainful employment forevermore, doest thou automatically–by dint of being in a state of non-employment–become a “boss,” much less your own boss?

I’m my own grandpa boss!

Stuff and nonsense. You are not your own boss any more than Dwight Latham is his own grandpa. The lack of a school marm doesn’t make you a nun, and the lack of a direct supervisor doesn’t make you a boss.

Let’s think about a few typical forms self-employment can take.

  1. Freelancing – As a freelancer, you work on a gig basis for small to medium sized jobs. This work is typically of a sort that can be done largely independently, without the help of others. Installing and customizing a Wordpress website is a good example of a freelance gig. Sure, you can quit at any time, but that’s true of any job short of slavery: technically you can quit, but in practical reality, you are beholden to your client. As a freelancer, you are not your own boss.
  2. Contracting – Contractors are probably the most common type of self-employed professional. A contractor can work on any kind of job, big or small, and often in the context of a larger team. The main difference between a contractor and a traditional employee is that (1) the work is typically understood to be temporary (but in practice can often stretch on for years), and (2) the employer is technically barred from telling the contractor how or when to do the work, so long as the work itself is completed according to the stipulations of the contract. Contractors, like freelancers,
    are beholden to their clients. Furthermore, unlike a freelancer, a contractor can’t simply quit at a moments notice without pentalty: there is a contract to fulfill. As a contractor, you are definitely not your own boss.
  3. Consulting – Consulting is often confused with contracting in conversation, but the two are very different things. Freelancers and contractors both perform actual work for a client. This could be any kind of job, really, but in almost every case it boils down to wage work. Consulting is different: a client asks your advice, and you provide that advice for a fee. I’ve done consulting gigs that were as simple as a single phone call with an investor, or as involved as a multi-month investigation into a company’s larger product ecosystem. This kind of work is rare, however. Most people who call themselves consultants are really contractors. If you’re a true consultant, however, you can make a good case for being your own boss.
  4. Selling a product – If you’re making a living by selling your own product, there’s a good chance you’ve crossed the border into the Land of Boss. Whether your product is a widget, gizmo, app, website, or serial manga printed on rolls of toilet tissue, your days are governed only by market forces and your own drive to succeed. I’ve made the better part of my living selling software products and web advertising for some time now, and the level of freedom and autonomy is much higher than freelancing, contracting, or consulting. I definitely feel like “my own boss” when I work in this capacity. It’s hard work with significant risk, but well worth it.
  5. Investing – If you are one of the tiny minority of people who is able to make a full-time living solely by investing your own money (and no, running a brokerage doesn’t count–that’s a job), then you have reached the pinnacle of Bossvana Zen Master. You are the boss of yourself, and probably the boss of lots of other people who rely on your investment for daily business operations. There’s significant risk involved, but it can be mitigated, and you are ultimately responsible for your own success or failure. I invest my savings, of course, but those investments are nowhere near sufficient to be a full-time living. Chances are, if you are reading SolidSmack, you are probably not in this category. (If you are, give us a call.)

Most self-employed persons have conventional third-party bosses. There is a pretty low chance that, as a self-employed person, you will ever truly be your own boss.

Good Boss, Bad Boss

What if your boss literally went everywhere you went, watched everything you did, and critiqued it in real time? What if everything you said, everything you did, ever email you wrote, and every YouTube video you watched was under the ever-watchful eye of your Own Personal Lundberg?

If that sounds like the eighth circle of Hell, you’re in luck! Being your own boss is not just like that, it is literally that. Congratulations! You are now your own boss, and simultaneously the worst boss who ever lived.

I’ve been self-employed for a long time. During those years, some of the time I’ve worked for others, and some of the time I’ve worked for myself. There are advantages to both. In the end, however, the important question is never whether or not you are your own boss, but whether or not you want to be.

If you decide, after all this, that you do want to be your own boss, just make sure you’re a good one.


Adam O'Hern is an industrial designer, designing products ranging from laptops to power tools, classroom toys to bathroom fixtures, and pro audio gear to guitar tuners. In 2008 he founded cadjunkie.com, and in 2010 co-founded EvD Media with Josh Mings of SolidSmack.com, and the two collaborate on the EngineerVsDesigner.com podcast.