Don't Overthink It

I told you about my boss who wouldn't drive in the snow, but I actually have two bosses -- brothers, Mike and Steve. They inherited the company from their father, and they're accustomed to a wealthier lifestyle than I am. Aside from our money, though, Steve, Mike and I share a common boyishness. We rely on our wives and our heroes to tell us when to pretend manliness, but left on our own we just quote Bill Murray, make poopy jokes, and play Businessman.

At the end of the day yesterday I went to Steve's office where they both were talking and I said, "You know I really have nothing much to do tomorrow. Mind if I take it off?" They told me that it was a bad idea because

a. I shouldn't tell my bosses I have nothing to do, and

b. I shouldn't let my staff see me taking a slow day off because it might cause them to panic, thinking the company is faltering

To be the boss is to be critiqued and analyzed - every decision is an illustration of your own beliefs, fears, hopes. When I'm mercilessly assessing Mike and Steve, I try to remember the seven people I manage are assessing me, too. I mean, I use very unnatural sports metaphors like, "Well, sometimes you gotta play hurt," or I'll make one of them stand there while I show off my amazing spreadsheet skillz. I hope they don't have cruel nicknames for me, but I have one for Mike: Crazy Eye.

If you write a two-paragraph email to Mike, you can be damn sure he didn't read the second; go ahead and fill it with invective or confess to white-collar crimes. He's always advising me to "use my gut" and "don't overthink it." So it surprised me when I first learned he was becoming a pilot. Flying involves maps, coordinates, clear communication, and 3D thinking that I just didn't associate with him. But when he's into something, he really gets it.

So, this afternoon Mike comes to me and says he's going to test-fly a plane he's thinking about buying, and would I like to go. "So long as you're caught up on your work," he says. "Well," I say, "I certainly have a lot to do. A lot. But I think I can carve out 80 to 200 minutes."

We took off from Portland and landed at a small, regional airport, then took off again and landed back at Portland. We had an instructor with us who, at one point, seized control of the aircraft when we were in (alleged) danger of hitting another plane on approach to the small airport. Without warning he put the plane into a hairpin 180 that felt like the right wing had reached the end of its leash. Later Mike explained to me that he wouldn't have hit the other plane, so that's very good.

Here are some shots from the Friday I had to come in to work.