7 Things I’ve Learned About Being Your Own Boss

“Man, it must be great to be your own boss.”

I hear this statement a lot.

There is something sacred in our American, capitalistic, independent, damn-the-man culture about the idea of starting your own company. It’s in our blood. It will always be considered a sacred occupation.

Yet, like a lot of things we hold sacred, being your own boss isn’t all it’s cracked up to be.

Let’s start with that phrase. When you own a company, you ARE NOT the boss. Your customers are. Add up your customers and that’s how many bosses you have. You thought having one boss was tough? Try having 20 or 50 or 100.

If your primary motivation for becoming an entrepreneur is to “be your own boss,” don’t do it. Please.

I’m not writing this to scare you away from starting a business. In fact, you would be hard-pressed to find a stronger advocate for entrepreneurialism than me. I’m writing this to share some of the things I’ve learned.

Last year I wrote a post just 90 days after starting Verge Videos. Here are some things I’ve learned since then:

1. Nothing is more important than the work. And nothing is easier to get distracted from.

We moved into our office in January. In September, we put a sign on the front. We jokingly ascribed a “minimalist aesthetic” to the interior because we didn’t have time to decorate. We were too busy working.

I see a lot of businesses spend an incredible amount of time trying to create or fix things that don’t directly relate to the work. I’m not just talking about decor and t-shirts either. Processes, policies, font choice, strategies, brainstorming…there are a thousand things we could have done. And honestly, a lot of them would have been more fun and easier than cranking out work every day.

2. Done is better than perfect. 

Perfectionism is a horrible strategy for growing a business. I’m still trying to accept this one. Every video we push out the door has at least one thing I want to tweak. And just let me say, this has absolutely nothing to do with the competency of our team. They do amazing work, better work than I could ever do. No project will ever be perfect. The anxiety I have about releasing imperfect work into the world is a problem with me, not the work.

3. Don’t spend time doing something you should be paying someone else to do.

My accountant was shocked when I said I wanted him to handle all of the “back office” financial stuff for our company. He said most entrepreneurs he deals with want to do it all themselves. They tell him, “I took an accounting class in college, I can figure this out.” I took a lot of those classes getting my MBA, but my time is better spent growing the business than banging my head against the wall trying to figure out what counts as a Section 179 deduction.

4. One hour of taking care of yourself is worth at least double that in productivity.

It feels so counter-intuitive to spend an entire hour of your day exercising or reading or journaling or blogging or cooking or whatever it is you do to stay sane. But that hour pays dividends far beyond an equal hour of sending emails or surfing Facebook or sitting in meetings or pretending to be doing something important. I have to constantly remind the workaholic in me not to feel guilty about spending this hour taking care of myself. Then I remember all the late nights and early mornings I invested in starting this business. And I don’t feel guilty anymore.

5. Fit work into your life, not the other way around. 

This truly is one of the main perks of being an entrepreneur.

Not everyone has this option and I feel very blessed to have the flexibility of fitting work into my life instead of arranging my life around work.

Yet, despite the benefits, I find it even harder to turn work off because so much responsibility rests on my shoulders. The pressure you feel as an entrepreneur can be overwhelming. I did freelance work for three years prior to going out on my own. Freelance is different. When you’re freelancing, you have your full-time job to fall back on. Unless you get fired, that paycheck is coming every two weeks. As an entrepreneur, it’s your responsibility to make sure you and your people get paid. This keeps me up at night more than anything else.

6. Iteration is key to moving quickly.

Iteration is the act of repeating a process with the aim of approaching a desired goal. “I’ll send you this now, it’s not perfect, but you get the idea, send us your feedback. Trust me that it will be better on the next version, in the interest of making progress.”

This relates to the point about perfection. It’s scary to send a half-baked project or idea to a client. Sometimes they don’t get it. But that first knee-jerk reaction can provide real insight into what needs to change.

7. There’s no way I could this without the support of my wife, best friend, and top advisor

To say I’m a lucky man would be the understatement of the year. The support, advice, and encouragement Mandy gives me is invaluable. She is a badass business woman, and if she were running this thing, we’d probably be a Fortune 500 company by now.