10 Pitfalls of Being Your Own Boss

It's a beautiful Sunday afternoon in August. All over the Bay Area people are out having fun in the sun. Me, I'm just sitting here trying to work. It's not going very well. I've spent the last half hour fixated on a couple of hawks gracefully riding the warm air currents above the majestic coastal redwoods. It looks like fun. Sigh.

My wife (also working) just texted, "On my way home. What's for dinner?"

Welcome to my life – the life of a boss, a small business owner. Not what you expected? Me neither. But I've been at it for 11 years and it's a little too late to backpedal now. The door doesn't really swing back the other way, not after that long. At this point I'm the only one who would ever hire me.

I know how sad that sounds but don't cry for me. I'm actually pretty content. It's just that there are a few things I sort of wish someone had told me before I pulled the plug on a lucrative executive career and jumped to the other side – you know, the one where the grass is always greener.

Related: Win or Lose, Competition Always Makes You Stronger

Would it have mattered? Probably not. Nevertheless, here are 10 things I know now that I wish I'd known then.

Self-discipline – what's that? Even after decades in the corporate world, the amount of self-discipline required to work entirely on your own – especially at home – was a real culture shock. Forget about forcing yourself to work; forcing yourself not to work is even harder. It takes real discipline not to be on 24x7.

The expenses really add up. The Fed says there's no inflation. I want some of what they're smoking. Health insurance, self-employment tax, income tax and payroll tax alone will eat you alive. Federal, state, local – all the bureaucrats have their hands in your pockets.

You become the house slave. It doesn't matter how much you work or how many X chromosomes you have. If you're the one that works at home, you're the one that gets stuck with most of the housework. Don't ask me why; that's just the way it is.

It is lonely at the top. What I miss most is the camaraderie, the relationships, the friendships, going out to lunch or for drinks after work with the gang. My dog is great but she just lies there.

There is no safety net. Everyone who works in corporate America should thank their lucky stars that, with rare exception, no matter how badly they screw up, someone is always there to bail them out. Even if you get fired you can go somewhere else. When it's your gig, you work without a net.

It is way harder than it looks. Maybe your passion is marketing, accounting, recruiting, engineering, design, web development or cooking. That's nice. Now you get to wear all the hats. You can outsource some of the work but you are still the chief everything officer. Running a business is harder than it looks.

There's nobody to dump on. You know the old expression "$#*! rolls downhill?" When you're your own boss it's as if there's an enormously powerful fan at the bottom of the hill that blows everything right back at you.

Related: Neurotic? It's a Good Thing.

It's a thankless job. I guess everyone gets a charge out of being recognized for a job well done or getting a bonus for exceeding expectations. It's like hitting a homerun or scoring a touchdown when you were a kid. Patting yourself on the back is just not the same.

It still feels like work. This may sound a bit naïve but you'd be surprised how many people get it in their heads that working for themselves is going to be different. It never occurs to them that it will still feel like work … because it is. You still have to do everything you hated about your job and then some. Surprise.

You may end up working for a loser. There's really no way to sugarcoat this so I'm just going to say it straight out: everyone isn't Bill Gates. Business success requires troubleshooting, problem-solving and decision-making skill. It takes perseverance, self-motivation and guts. It takes a lot of things that most people don't have.

Still, there's something to be said for experiencing all that on your own. I mean, who am I to deprive you of all the pain and frustration? Besides, there's an awful lot of fun and fulfillment, too. Good times, bad times. Yin and yang. That's life and, you know, I wouldn't have it any other way. I take it all back. Working for yourself is a blast, a trip, a walk in the park. Go for it.

My work here is done. Time to start on dinner.

Related: What Makes a Great Boss?