Get ready for some good ole’ fashion tangents.
Road trips are the best thing on earth, if you do them right. Right is when you just get in the car and go. Maybe you have a couple days notice to plan for a minute, but anything over a week and it’s going to just go to crap. In fact most trips are better on a whim, depending on how complicated of a trip it is.
I believe this all comes down to expectations. When you only have a few minutes to plan something you don’t have enough time to get overly excited. You immediately get into planning/prep mode and the next thing you know you’re gone and you’re on this journey that’s going to take you to…wherever you want. If you plan too far ahead you get excited, then you worry about the weather, or maybe there has been a rogue uprising that has made it unsafe, or you see that a cruise ship is stuck in the middle of the ocean and wonder if that will be you. For me it all comes down to setting expectations.
Expectations have got to be the hardest thing on this planet to manage and setting up for disappointment is the easiest thing in the world. In fact, it’s a big ass trap. Developers and other support type roles in companies experience this all the time. As soon as you get a project, you want to impress the person that gave it to by telling them how quickly you’re able to get it out. You want them to feel like they’re in very capable hands and that you’ve got it. You let them know you can knock it out in a just a few days and boom…a couple days after your deadline and you’re still working on the project. It takes a wise person one to understand how strong their skills are and to be humble enough not to overstate them to your clients. This is something I’m trying I’m working on, and there are some great people I work with who are very masterful at this. I salute them, but I still think an epic road trip beats out all other trips any day.