I recently took myself on a solo staycation and turned it into a personal CEO Day. I plan to do a CEO Day at least once a year from now on and recommend it to others.
After spending several hours without my phone in Montana earlier this year, I wanted to see what uninterrupted time alone would feel like because I’ve never actually had it. I’m 35 years old and have never traveled somewhere that wasn’t for business or a social event with friends or family. That was a crazy realization in itself for me.
To keep it simple, I went to a beach resort within driving distance and did one day. Have to start somewhere. Before going, I worked with ChatGPT to create six one-hour sessions with the goal of identifying actions that could have an outlier impact on what I actually want my life to look like at 45.
During each session, I spent 30 minutes talking through a topic using Wispr, then gave the transcript to GPT and asked what themes I was missing, where I was contradicting myself, and what questions I should spend the remaining 30 minutes answering.
Creating the agenda beforehand and having a thought partner (GPT) challenge my thinking made the six hours much more productive. As an extrovert, six hours alone was harder than I expected, so I changed locations every session: outside, inside, the beach, restaurant and hotel room. That small change helped keep me fresh.
My biggest realization was that I’m not less ambitious than I used to be, but my definition of success has expanded. I still want to find exceptional companies and create wealth, but my marriage, fatherhood, friendships, faith and health are now equally part of the scoreboard.
I don’t believe I need to sacrifice everything to accomplish exceptional things. I need to get much better at sacrificing the things that don’t matter so I can go deeper on the things that do. It’s about becoming a better, more intentional version of who I already am.
We spend a lot of time intentionally planning offsites and retreats for the fund and our companies. I’m going to start doing the same for myself, and I think you should too.