A Field Guide to Self Employment

After more than ten years in the web industry, Guerilla Labs began as my full-time employment on October 1, 2013. As I sit here at one and a half years, I want to look back and and share what that journey has been like.

I get asked questions all the time about starting a business, and I am no expert, but I’ve come to realize that my experiences – the specific decisions, considerations and results – are valuable to a lot of people looking to start their own things. So, this is an attempt to lay those items out in as clear a manner as I know how. It has become pretty lengthy, though (who knew I’d learned so much!), so I broke it down into multiple posts – listed at the bottom of this page.

Please remember that I’m just one guy, and what worked for me might not necessarily be the best plan for you. Also, I’m no lawyer, so, you know, this shouldn’t be construed as legal advice.

The Fear

I had been thinking about starting my own business since I was in high school. Well, thinking may be a little strong since I never actually took the time to think about what kind of company I would start – daydreaming would be more accurate. But, here I was nearing my mid-thirties, and I had never stepped out on my own. Why?

The fear.

The fear of not having a “great idea”, of not being good enough, of not finding work, of not bringing in enough money, of being exposed as a pretender, of failing. That’s a lot of junk to get through. Sitting on this side of things, it’s easy to look back and realize how long I let those fears paralyze me – and, yet, also realizing those things aren’t real. The security that comes from working for someone else is an illusion.

And, yeah, I still fight the fear every week. This afternoon, I sit here writing about my experience, and while I’m recognizing all the things that have gone right a little voice in the back of my mind tells me that my most recent job was my last. But it’s a lie. If I can get past the paralysis, get up and do the work, then it still may not work out. Sure, that’s part of it. But there’s a really good chance that it will.

Why are you doing this?

Just like security is an illusion when working for someone else, there are plenty of illusions to be careful of when starting your own business. Freedom, money and time are the big ones. So, let’s settle this right now. Yes, I have more freedom, but I still have clients I must answer to (and bills to pay). Yes, I have more time with my family, but I have to be really careful with the jobs I take to not give that away (as I did during a few periods of the last year). But no, I don’t have more money, yet — and I may never make up the money I gave up to make this life a reality.

So, why are you doing this? Be sure to be honest with yourself, because you have to know what you’re willing to sacrifice.

If you’re doing this to spend more time with your family, are you (and they) ok in giving up on a certain level of income you may have become accustomed to over the years? If you want to make more money, are you willing to work longer hours or take on employees (and perhaps not get to do the work you’re most drawn to) in order to get there?

Take a long look in the mirror. Now let’s get started.

Table of Contents