I signed on to my first job the Tuesday after Labor Day 2001. I quit my last one, the Friday before the same weekend of this year.
The euphoria wore off on Wednesday. On Thursday, I decided that the biggest challenge of working for yourself was not knowing if you had done a good job at the end of the day or not. For over fifteen years – including the years I was in grad school – I pretty much knew the answer to that question every single day. If I thought that my boss (“advisor,” when I was a grad student) was feeling good about me, then I could check the day off as a success. Otherwise, I knew I had to work harder.
Granted, this fantasy that I could, in fact, walk out each day hoping to have actually made a positive difference in my boss and employer’s lives, wore off as I got older. In recent years, I had lowered my hopes a bit – I figured that as long as my boss wasn’t going to fire me, I was doing fine.
When you are your own boss though, things get a bit more complicated. I am a very harsh critic, of many things, including people who report to me. Which now includes – and is limited to – me.
For many months, I have been working away at offering my services as a tech consultant to a variety of nonprofit and other mission-based organizations. Along the way, I have received a great deal of support and learned a lot about myself. Somewhere in the spring of this year, I learned something very critical – that you can’t run a business, or even pretend that you are, after-hours. There are no weekend warriors among entrepreneurs. That’s what hobbies are for.
Some “clients” started threatening to pay me. I began to see the possibility of taking those scare-quotes off.
I also learned that I was my own “MVP.” For a long while, I had known that I wasn’t a very good employee. I have more than once had a senior leader in my company end our conversation by telling me that I needed to stop disagreeing with him/her because he/she had a bigger title than I did. When I couldn’t hold my counsel, I got fired.
What exactly would I do instead, though? If I had a company, what would it sell? The best minds of my generation are busy making prettier digital billboards. Some are selling handbags and nicer vacations; others are helping you find Katy Perry videos faster, hopefully before you even knew you wanted to watch one. The Internet is one big circus, with a well-lit XXX arcade around every corner. Being a carnie was no fun. I was in theater once; it’s good for the sex and then it gets boring. These bazaars didn’t have a stall where I could hang a shingle up without feeling less ennui than I had found behind the average office desk. I had no way to justify quitting a good job, without feeling like a slacker.
Then it came to me, in a flash. What I was selling, or would like to sell, was myself. To be more explicit – the product I had in mind was, simply, my vision of a different world where technology was used more effectively for the collective good. I wasn’t hawking anything more tangible than the value that I believe that I, and people like me, can bring to a socially conscious marketplace. That’s what I was going to validate, and find customers for, and bring to fruition, as an entrepreneur.
In short order, I gave notice, got myself the domain name Digital Strategies, created a Twitter handle, and spent two days teaching myself enough graphic design skills to make a business card. If you are trying to change the world, and want a good website to do it with, give me a call. (Hurry! We should have changed the world yesterday.)
On my fourth day of self-employment, I had quesadillas for lunch that my wife had made. Crisp, cleanly cut, stuffed with mushroomy goodness. Much wouldn’t have been possible, and many possibilities would have been much less fun, if it weren’t for a constant companion.
Lunches made with love notwithstanding, a downside about working for yourself is that you have to make an effort to find people to small-talk to. A workplace comes with a panoply of built-in conversations. The microwave and coffee machines are always buzzing. There’s someone at the front desk. Even your annoying co-workers will form a distraction that gives you a reason to look away from the desk and allow your mind to wander.
On my sixth day, I could swear I was sitting in front of the computer for so much time at one stretch, I was getting physically sick. So now my dog gets walked a lot more often. She approves of my new adventures.
On the tenth day as a free agent, I signed my first contract.
Shit. Back to work.