Credit: Lindsey Snow

Blog reader Derek Bobo asks via email:

I was wondering when and how you made the leap of faith to work for yourself. When did you know you were safe financially? What was the deciding factor, etc? I’m right on the brink but can’t seem to get myself to take the leap of faith.

Excellent question. Here’s my answer:

While a student designer at BYU, my department liked what I did with websites, so I thought I could probably make some money designing them on the side. I formed an LLC dubbed Griffio the summer before my senior year (2003), and by Christmas I was making four digits a month! (It was only $1000.) Still unsure of what I wanted to do at the time, I kept interviewing for corporate jobs, and came really close to becoming a management consultant that traveled all the time without seeing his family during the week. Glad I dodged that one.

As the playing of Pomp and Circumstance neared, I thought to myself, “Why not try this self-employment thing while you’re expenses are crazy low?” With a supportive and low maintenance wife, I was able to. So I ventured into lone and dreary adulthood on my own. I paid myself $1000 a month for the first few months after graduation (gotta save for a rainy day), and slowly lined my pockets, after gaining a reputation through lots of cold calling, in-person meetings, repeat business, and luck. Somewhere in there, I became a contributing writer. That’s the condensed version of how I started working for myself.

Regarding you’re second question, I don’t make a lot of money, so I still don’t feel “safe financially.” In fact, I’m not quite sure such a thing exists, unless of course you’re one of the few millionaires in the world who keeps their spending in check. I live a comfortable life, and indulge in a few luxuries, but that’s more because I avoid prohibitive expenses like a costly mortgage and second car payment than any piles of cash I might be making. So that has been my strategy for producing the illusion of financial security while trying to make it big—by shunning unnecessary costs. As Mark Cuban says, “The cheaper you can live, the greater your options.”

The deciding factor, you ask? I’d rather make money in life doing something I enjoy, as opposed to getting paid (sometimes well) for something I don’t enjoy. Like putting cover sheets on TPS reports.

But there is a caveat to my response. I don’t consider myself an “entrepreneur,” whom I define as someone who builds wealth for others, not just themselves. In truth, I only support my own family, with exception to a handful of American freelancers I periodically outsource work to. That being the case, I’m probably better described as “independent contractor,” “freelancer for hire,” “consultant,” or “self-employed.” Because it sounds better, I currently refer to myself as a “proprietor.” (It has a sophisticated ring to it, no?) In any case, if you’re trying to become a proper entrepreneur, there are more qualified individuals whom you should talk to. I’m really just a hack.

That said, there is more than one way to skin a cat. And I am by no means the standard of self-employment. Any Smooth Harold readers out there supporting yourself and/or others? If so, how did you do it?