Freestyle Mentality

I was a little bit nervous the night before I held my first Superhuman event in Las Vegas. People had paid a fair amount of money and had traveled long distances for an event, but I hadn’t planned anything. It was very important to me that everyone have an amazing time at the event. Still, I restrained myself from trying to plan out what I would say.

The few times I’d go to a conference or workshop that was carefully scripted, I was disappointed. If you already know what you’re going to say and don’t intend on having an interactive experience with the audience, you may as well just put it up on video.

This is how I do almost everything, and have been doing it for years. I don’t think that it is the right strategy for everyone and I am very aware that it has weaknesses, but it works great for me and I wouldn’t do it any other way.

My basic premise is this: I want to develop my skills and mind to the point that I can execute at a high level at a moment’s notice, even if I’m doing something that I don’t normally do. I focus on root skills that are broadly applicable rather than specific one-time-use skills or plans.

For example, when Todd and I went to Japan for the first time we didn’t book anywhere to stay until the night before the flight. We figured out everything we wanted to do once we got there. I’ve done a number of trips in the same way, and often change my plans at the last minute.

Every first date I went on in the couple years preceding meeting my wife was just me and the girl sitting at tea talking. No activity to distract.

When I write books I just sit down, make a quick malleable outline, and start writing. With blog posts I just write down the title and start going, rarely doing any significant editing.

If I’m building something on the island or at my house, I just get some tools and materials and figure it out along the way.

This approach means that I sometimes have to revise. I’ll build something and then realize it’s too tall so I have to cut something down. I’ll write a blog post and then realize it’s not good enough to post so I have to scrap it. There were a few things at my first Superhuman event that should have gone more smoothly, so I changed them for the next year. It’s not a perfect system.

It has its advantages, though, and for me they overshadow the disadvantages. I am extremely able to adapt, because my plan was never that rigid to begin with. I planned (the week before) a seven day train trip for my friends and I. When we arrived at the ferry dock to see no ferry waiting for us due to a typhoon, I spent a few minutes and made a new plan. If I was totally reliant on a written plan I would have freaked out.

I’ll still get nerves when I’m about to freestyle something big that matters to me, like a live event, but this method decouples the work and performance of putting an event on. I know that I’ve done the work in my life to have the answers for people, so I don’t have any serious anxiety or stress about it. When I was on my Japan trip it didn’t matter to me that something went wrong, except that I was really looking forward to going to the island that we couldn’t reach.

General domain confidence is valuable, but the freestyle method gives you general confidence. I know that because I have a strong set of fundamental skills, I’m likely to be reasonably good at just about everything as a beginner. I’ve gotten a lot of compliments at my performance at tea ceremony, but it’s not because I’m actually good at it, it’s because I’ve learned how to learn quickly, how to move somewhat gracefully, and how to remain calm and on track when a make an error.

Some people do much better as planners, and that method is no worse than the freestyle method. Each comes with its own pros and cons, and its up to the individual to determine which suits them better. For me, though, I’ll keep freestyling.


Photo is an amazing tea-themed hotel at Mengdingshan in China. They had all sorts of crazy tea rooms that you could use, like this one on the roof.

My next Superhuman event is going to be in Vegas in a few weeks. After that I’ll plan a Budapest one soon!

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