I saw a young-looking guy today driving a very nice work truck, pulling a dump trailer. I was right behind him when he stopped at his jobsite—a house getting a new roof. He had to back that trailer into the driveway, right up to the roofline, but he just couldn't quite make the geometry work.
He backed in, went badly crooked, and pulled up. Then again. Two, three, four times. He was getting faster and more frantic with each pull-up. Meanwhile, the neighborhood traffic was piling up. There was a car behind me and three more on the other side of the road, all waiting on this guy to figure it out.
I could practically feel the heat radiating off him. He was sweating bullets, gripping the wheel, painfully aware of the audience accumulating around him. Finally, he jammed it into a "good enough" spot, and the waiting traffic zipped by him without a second glance.
I’ve been that guy. I think we all have.
You have to get this trailer backed in, or that piece of equipment loaded, or such-and-such horse to settle down, and if you’re being honest with yourself... you are completely out of your depth. You are out of your skill level for the job at hand, and now you have witnesses.
Sure, if you had ten minutes and an empty parking lot, you could do it. But the pressure is real, and it grows with every ticking second as a new and impatient observer pulls up to the bumper. You can’t get the trailer to back in a straight line to save your life—and in that moment, with your heart hammering in your ears, it feels like your life is actually on the line.
But there is nothing wrong with that. In fact, it’s necessary.
Things are never going to be perfect. You just have to find a way to sit in that hot seat, deal with the pressure, and get it done ugly if you have to. I think that kid in the truck is better off for that little backup fiasco. He paid a little tuition in sweat and shame today, but he bought a lesson he won’t forget.
December 28, 2025