When you work for yourself, your boss is probably an asshole

Bosses can suck when you’re self-employed (aka: when YOU are the boss of yourself).

It’s sort of like there’s two of you. There’s the Creator You who’s doing the actual work and then there’s the Boss You, overseeing everything, making sure deadlines are met and cash comes in the door.

The Boss You can sometimes be a real prick to the Creator You.

Always making you hustle. Working you for long hours for little to no money. Blatantly disregarding evenings and weekends.

You want benefits? You’re lucky you have a job! You’d better think about job security next time you pipe up. If you’ve got time to complain, you’ve got time to get more work done.

You were lured in with promises of spare time and money fights. There was even vague mention of travel and day-drinking as well. You didn’t believe these claims at first, but you were pointed to so many expert blog posts detailing how wonderful your new job would be. Fame! Riches! Freeeeeeeeeeeeeedom! (It helps if you say this in your best Mel Gibson, Braveheart voice).

You started out thinking this would be the best job ever. That you’d be in charge of your own destiny. You’d set the hours, work only when you felt inspired and answer only to yourself. Time off would out-weigh time spent working.

But then you started the job and things became drastically different. The opposite, in fact. Some days you can’t even claw your way out of the minutiae of administrative and operational tasks, just so you can have a second to do your actual job.

Sleep? Socializing? Television? You’ll be able pick one of those… maybe later. Heaven forbid you don’t make money for any length of time, because then you have to work even harder. Get on social media and start selling, got-dammit.

This is what happens when your boss is you. As in, you work for yourself. For most of us who do that, our bosses can be real jerks.

We start out thinking it’ll be life on easy street, full of passive income and frolicking (insert geographically-dependent daydream).

Quickly, we realize it’s far more work than being an employee at some big company. That’s because we can now only delegate in two ways. The first way is to put something further down our own to-do list and second is by paying someone else to do it (with money out of our pockets!)

We also have to come to terms with the fact that we don’t know or aren’t good at many of the things we actually need to do to run our business. Worst of all, they’re all things that have nothing to do with the sort of work we want to do. I’ve worked for myself for almost 20 years now and I still suck at: contracts, bookkeeping, remembering to send clients invoices, scheduling meetings, and working when I shouldn’t be (hell, I’m writing this at 10pm and should be sleeping).

For most of us, we also need to learn how sales and marketing work. It’s not enough that we’re good at making something, we’ve also got to connect that something with the right people. The right people being those who are willing to trade their money for our something.

It’s certainly a long and hard road, but it can be very fulfilling too. Once we “figure things out”—which I won’t even get into because it’s different for everyone—then we can actually find some freedom, more meaning, decent hours, and good pay.

But until then, when you work for yourself, your boss is probably a bit of an asshole.

The good thing is, asshole bosses don’t need to define us or our work. We don’t even need to listen to their tirades in our heads if they don’t serve us. In a culture that romanticizes entrepreneurship and paints a dream of fairy-tales and private jets for all those who try, we need to get real. It’s not for everyone, it’s a lot of damn work, and there’s no shame in having an actual boss instead of one that’s you. Doing a 9-5 job or even going back to one isn’t a failure, it’s just a single point on your own journey. Don’t force things, don’t rush things and wherever you’re at, make sure you or anyone else isn’t working yourself too hard.

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