At HealthPro, we recently started having some company culture discussions. The general idea is that a company will always have some culture, and that you can influence what it becomes by being aware of it and proactively discussing it. After a general brainstorming session together, we started discussing things in Slack (“Work As If Remote”, right?)

The value that we were discussing was “Try new things / Don’t be afraid to make mistakes”. One of Kyle’s questions that seemed to get a lot of response was “What’s the most spectacular failure you’ve been a part of? What did you learn from it?”

I liked my response, so thought I would share it with everyone now.

My Story

One thing that I did in 2011 that was a pretty big failure in my mind was unsuccessfully trying to go on a cross-country RV trip.

I had some money saved up and the startup I was working for had folded (which is probably a failure story itself), and thought it would be good to get away from everything and travel out west and try to play a lot of Ultimate. I thought that I would need a small RV to make living work (and could maybe code or something in there), so traveled several hours to Kentucky based on a Craigslist ad to buy a 22-foot 1987 Winnebago Minnie Winnie. My (now) wife drove me there and followed me back in one very long day.

When driving back, we stopped at a gas station, and the RV wouldn’t start! We waited a bit and it started up again, but I was loath to stop it again. When we got home after about ten hours of driving round-trip in the summer, I was pretty exhausted.

I am not mechanically inclined, so considering driving across the country in a 25-year-old RV was not really that exciting. I kind of freaked out and sat in the basement for a day or two. I signed up for a conference in Colorado that I was going to drive to that week, but didn’t end up going and so lost out on the money that I put into it.

The RV sat in the driveway through the winter. After nine months I put it up for sale.

The woman who ended up buying it has the foresight to have a mechanic appraise it, which seems like a smart thing to do. They said it had some roof damage, so I ended up selling it to her for about $2000 less than what I bought it for. The mechanic also said that there was essentially no oil in the thing, so it was lucky that I didn’t burn up the engine with the several hour drive from Kentucky. I was glad to be finally rid of it, but it was a fairly expensive mistake.

Obviously in the grand scheme of things, it was not that big of a deal. Instead of going on the trip I used the rest of the savings to start some independent work, which launched my consulting business. If that is the worst thing that happens to me, then I would consider myself very fortunate.

Lessons Learned

First, get vehicles checked out if you aren’t sure about them.

I realized that there were easier and cheaper ways to make the trip that I wanted to take. I could have taken my pretty well-functioning car and bought a tent and camped out. The gas certainly would have been cheaper (30 MPG vs 10 MPG.) Plus, I would have saved the capital outlay and potentially loan interest of purchasing another vehicle.

Do the simplest thing that could possibly work. Instead of making the big trip first, make smaller trips to figure out if I like it or not and I can come back easily if there are any complications. While having the conference as a deadline pushed me to action, I might have made worse decisions because I tried overcomplicating things early.

Last, play to your strengths. Buying a super-old RV that I didn’t know much about and that I would need to maintain was not in my wheelhouse.