Every year, my dad and I go on a father son trip somewhere for the weekend. We go wherever he wants to go. This year we are going to Chicago – I’m heading out in about an hour. In the past, we’ve gone to Las Vegas, Los Angeles, San Francisco, San Diego, Austin, Miami Beach, Las Vegas again, and a few other places.
I think Chicago will be perfect for us. Our goal is just to hang out. This afternoon we are doing the Chicago Architecture Foundation River Cruise, having a drink with my long time friend Jeff Hyman (my very first VC investment was in his company Career Central, which ended up changing it’s name to Cruel World, which was fitting for its ultimate demise), and then dinner at Swift & Sons.
Tomorrow morning I’m going for a long run, we are going to the Cubs game, getting a tour of Wrigley Field, and then having dinner at Coco Pazzo with Troy Henikoff (who runs Techstars Chicago) and his wife Kristin. We are heading home Sunday morning.
There will be a lot of chocolate ice cream. It’s our favorite food and we will have it at least twice each day.
Maybe we’ll have it three times on Saturday if they sell it at Wrigley Field.
My only regret about my father son trip with my dad is that we’ve only been doing it for a decade. I wish we had started 40 years ago. If you are a father and your son is at least ten years old, I strongly encourage you to consider this tradition. If you are a son and you are at least 20 years old, I encourage you to take the initiative and just start doing this with your dad.