When are you going to get a real job?

Back in college, I decided to start my own web design business. Frankly, I had absolutely no idea what I was doing. The only thing I knew is that I wanted to build websites for people and I wanted to do it on my own.

At the time, I was interning at the faculty and staff technology resource center (a fancy name for IT department), and it gave me access to the web developers who oversaw the university website.

Everyday (instead of working), I’d be pestering the crap out of them for advice, always eager to learn a little more — to understand.

I have to thank my first few clients because the websites I designed for them were pretty horrendous, but I learned a lot:

  • What I thought they wanted vs. what they actually needed
  • People’s preferences for classic design vs. trends
  • The importances of meeting deadlines
  • Not to undervalue my services
  • How to communicate setbacks and delays
  • A million other things that are just as important

Overtime, I built myself a decent little freelance business. Like so many independently employed people I found cash-flow to be the most difficult problem to solve. Feast or famine was a common occurrence.

It was during these periods of temporary poverty that I started to get asked a question that would follow me around for years to come:

“When are you going to get a real job?”

It took a lot of different forms:

  • Subtly sending me job listings
  • Mentioning companies that were hiring
  • Alluding to a future where I’d be gainfully employed
  • Condescending replies when I’d say what I did for a living

Worse yet, many of these came from my most trusted inner-circle; friends, family, and even mentors. I got sick of defending my choices, and I didn’t understand why they couldn’t just be supportive.

I even caved a few times over the past ten years. I worked at corporations, small businesses, startups, and nonprofits. I took positions in marketing, sales, development, and operations. Nothing ever made me happy.

I’d start out with enthusiasm and an intention to make the position my own, give it my all, and try to find something about each job that I loved. Afterall, according to everyone around me, this is what I was supposed to be doing right? I thought it was just a matter of perspective.

Inevitably it wouldn’t work out. There wasn’t the same feeling that I had when I was working for myself. Sure I had a steady paycheck, but that insatiable drive was missing. It was replaced with an empty feeling.

No matter how great the company, how cool the office, how big the salary, or even what my responsibilities were, I was missing the thing that I loved.

It’s not surprising, because working for someone else removes a lot of the different responsibilities and choices that you have when you work for yourself.

You’re often required to specialize in one thing rather than having to handle a dozen different things. You can’t make meaningful decisions without consulting someone ahead of time. You’re freedom of action is a sliver of what it is when you’re working independently.

Most importantly, even if you bust your ass and do an amazing job producing extraordinary results, you’ve just poured a lot of working capital into a company that you probably don’t even own a share of.

I’ve come to learn that working for myself isn’t a choice, it’s as much a part of who I am as my own name. It’s a core part of my identity. It’s what drives me to get out of bed each day and keeps me motivated.

Come hell or highwater I’m determined to succeed. Sometimes I’m terrified, sometimes I’m broke, and sometimes I think about going back to work for someone else.

To put my livelihood in someone else’s hands.

But I can’t.

Like anything else that you love irrationally, it’s not something that I can control. When I got my first taste in college, I was permanently changed. Like a caged bird that’s been released into the open outdoors, I won’t give up this exhilarating feeling of complete freedom. Going back feels like prison.

Everyone has dreams, both big and small. You might want to run a food-truck, create a clothing line, solve the energy crisis, build software, design a videogame, or become a buddhist monk. I don’t care what it is, everyone has something that they desire. Something that calls to them.

For me it’s this.

I just launched my own company from the ground up. I’m bootstrapping my business and everyday I’m grateful for getting to work on something that’s entirely my own. My destiny is in my own hands.

I don’t want to wake up someday and realize that I’ve lived my entire life in the service of someone else’s vision. I want to pursue my own.