I’m not sure where I read it, but I recently came across this quote: “It’s not that good entrepreneurs are comfortable with risk, they are comfortable with uncertainty.”

I think there is something to that. Of course there is risk involved with starting your own business, but there is risk in everything. Before Chuck and I started Sharp Analytics I had a good job that paid well. I didn’ really take a big risk when we started Sharp because I didn’t have to quit my job at first. I spent a few months of long nights and weekends trying to get things going at Sharp Analytics while I kept plugging away at my day job.

After a few months of working both jobs and saving everything I had made on the side, I was ready to leave the comfort of a steady job and try my hand at entrepreneurship with Chuck. I remember talking to my wife about whether or not I should quit. Her instinct was to say no but she made the mistake of telling me to call our friend Rick, a successful entrepreneur. She told me that if Rick thought it was a good idea then I could quit.

I’ll never forget that call. We only talked for a few minutes and Rick didn’t really ask me any questions about the business. All he needed to know was that I was going to do something on my own. I remember he asked me what the worst-case scenario was and he asked if I would be able to get a job doing more or less what I was doing now if the business were to fail. When I said that I thought I probably could get a job he said, “Then you are asking the wrong person. I would tell anybody to quit working for someone else and start a business.”

At the time, I thought I was taking a risk. But the truth is that it wasn’t much of a risk. And the risk that did exist was calculated and mitigated. Calculated because I knew what the worst-case scenario was and it wasn’t that bad. Mitigated because I had some personal savings and because the job market was pretty strong at the time. So in hindsight, I don’t think I took much of a risk at all. I did, however, leave the certainty of a regular paycheck and steady work, the certainty of a job description and knowing who reported to me and who I reported to. I had MS Project telling me what to do most days. I had a lot of certainty. I gave that up for a lot of uncertainty.

And though startups tend to focus on cash (or the lack of it), the uncertainty we faced was more than just the uncertainty of a paycheck. Chuck and I did not know what we were doing. I need to track down our business plan from those days and compare it to what we actually did because I’m sure it would be very entertaining. We ended up landing a client that was huge for us and we were scared to death. We hoped we could do what we promised but we didn’t know how we were going to accomplish it. That’s material for another post, but let me say that I nearly had a nervous breakdown but we ultimately delivered what we promised a little later than we’d hoped. It was a miracle.

The truth is that we iterated through strategies until something finally clicked and it clicked just in time. And all along the way, we dealt with uncertainty on issues as core as “What do we do?” to “What do I do?” to “How do we work together?” and we got really good at being comfortable with the uncertainty and figuring out how to make it all work.