A Lesson in Entrepreneurship From Playing Chicken With a Squirrel

The following is a blog entry I originally wrote many years ago, for humor value. Re-reading it again this morning, I realized it illustrates at least one personal, striking lesson in entrepreneurship. 

I went to college in the early 90's in East Texas, where a man is often equated with the truck he owns. I say 'often', because if it were 'always', then my roommate John would have been the biggest, nastiest, most gargantuan creature of all time. And he would have smoked and rattled. To get back and forth between our house and school (or maybe it was suggested by their home owner's association), John's family gave him their big, old, 1974 Ford Extended Cab pickup, formally known as The Guck. Now remember in 1974, American automobiles were BIG. 1974 was the first year for the extended-cab, so Ford made that BIG, too. And it had a camper. A BIG camper. This gargantuan beast was so big, we actually measured the carport before his parents brought it up, just to be sure it fit. We ended up with about an inch to spare – but we measured twice just to be sure.

The technology was classic simple 1970's era automotive, but when we sat down in that thing to go to school in the morning, it still felt we were settling into the cockpit of a 747 for a transcontinental flight. Wipers – check. Mirrors – check. Ignition! Now when this beast roared to life, any birds, squirrels, and small children in the area scrambled for cover. A high-velocity plume of blue smoke blasted through the rear of the carport, and we were ready to make it to our 8:00 class.

I don't know why I was always driving (perhaps because I always wanted to fly 747s or something), but I'd often pilot the Guck through the (luckily) expansive streets of Nacogdoches, Texas on those mornings, headed for the University and welcoming the daily challenge of finding a parking place large enough where we could still open our doors if anyone unwisely parked on either side of us. I'd have to psych myself up a bit, but I was always ready. If I'd had a pair of goggles and an aviator helmet, I'd have had 'em on, right along with my characteristic grin (or was that a grimace? Whatever.) I took my job seriously, and I was good at it. John would generally sit in the passenger seat and get a few minutes more studying in on the way.

I remember one fall morning very well. The sunlight was streaming down through the trees to the leaves on the street in a camouflage pattern. The air was crisp and cool, and the birds were out, gathering a few more provisions for the coming winter. Unfortunately, as it turns out, so were the squirrels.

I don't know if I saw the squirrel first, or if he saw the Guck (or maybe it's massive shadow just blocked out the sun), but evidently he took his nut-gathering activities every bit as seriously as I took my job of piloting the Guck. We were clearly both determined, focused, and ready that fall morning. He started out across that street, and I immediately felt my heart rate increase, vision narrow, and stomach tighten.

Now I used to advise my physics lab students that the mind is an incredible instrument. The amount of mathematical calculation required to determine the correct location to put your glove to catch a baseball, for instance, is huge – but your mind does it all unconsciously, and FAST, when someone throws one to you. In this case, my unconscious mind had already done all the math for the intersection of the Guck's trajectory with the squirrel's path, and it was going to be OK. John must have started to sense something, too – he glanced up briefly. I'm not sure what was going on in the squirrel's mind.

By this time, that squirrel had made it to the middle of the street, and suddenly, he invalidated all of that unconscious computation I'd done, and turned 90 degress to his left – and charged straight for the Guck. Now if the Guck really were a 747, I could just picture all kinds of master alarms going off, buzzers and flashing red lights, and a pleasant voice saying 'Terrain! Pull Up!'. As it turns out, my conscious mind was doing all of the buzzing and flashing, and the voice there just screamed 'STOP!!!!'.

And so I did. In lightning-fast, adrenaline-induced reaction, I somehow removed my right foot from the gas pedal and placed it directly onto the brake pedal, in record time. And hard. Now it was the Guck's turn to react. All four wheels locked up, and we slid, turning sideways in the road as we did so. There was smoke. There was screeching of tires. There was bouncing and rattling, and more smoke, and the Guck's engine died. Everything in the cab was flying around, and then just as abruptly, everything finally settled down and came to a halt, just in time for Mr. Squirrel to turn 90 degrees back to the right, and continue on his original journey to the other side of the road.

As I picked everything up off the floor, took a deep breath, and restarted the Guck, John looked over at me as if to silently and casually question what it was I might have been doing. I just blurted “MAN, that was one SPECTACULARLY STUPID squirrel to play chicken with THIS truck!”. 

John turned the page before casually responding. “He won, didn't he?”

There are a few lessons in there, but the one that sticks out in my mind today, as the end of 2016 approaches, is this: As an entrepreneur, self doubt is the enemy. It will Mess.You.Up. (Well, maybe not you - but definitely me!). That squirrel had ALL KINDS of reasons to doubt he'd win that game of chicken, and I, in the Guck, had exactly zero -- yet who won? I'm a pretty introspective guy, and I'll readily admit that the business decisions that I regret the most are those where I let self doubt get the best of me. As one example that I've talked about quite a bit, I shut down DriverDev in 2005 -- on our single most profitable day ever -- because I didn't think I knew how to scale it further. That one was particularly seductive, because it felt a little like going out on top -- but how far could I have taken it if I had figured that out?  Other similar organizations have, and done quite well. That was a long time ago, and I've grown significantly in this regard since then, but self doubt is still something I have to really work to keep at bay.

Shortly I hope to get back to blogging about Google Calendar Charts, in the form of a tutorial, but for now, whether it's playing chicken with a squirrel or a business decision, I'd love to know YOUR story. Is there a time you, like me driving The Guck, let self doubt (perhaps ridiculously) get the best of you? Or even better, where you DIDN'T let self doubt get the best of you, even when it was well warranted and completely rational?  Please share in the comments!