Two Totally Different Careers I’m Considering

I’ve gone through a lot of cycles of expansion and consolidation. I make a ton of progress, but then I circle back and solidify it, making sure that the gains will stay with me and that I’m unencumbered enough to do the next thing.

Now I’m in the curious position of having reached all of the goals that actually matter to me. Sure it would be great to have more money or to visit more countries or have more adventures, but I’m self-aware enough to know that each of those areas will produce diminishing returns.

My ongoing campaigns like coaching, writing, and CruiseSheet don’t require huge amounts of effort. I could certainly spend a lot more time on CruiseSheet, and I do plan on ramping up to some extent, but it doesn’t seem clear that I can fruitfully fill up months with CruiseSheet work.

So I’m thinking about doing something totally new. Here are my two ideas and why I am considering. I may do one or both of them, something totally different, or nothing new at all. I often consider things with no pressure or prejudice, just to think about what it would be like.

1. Become a Rapper

I like rap music a lot. Not as much as some people, but classical music and rap music are the only kinds of music that I like, and I’m really into both. I sing a ton of rap karaoke, sometimes in front of large audiences, and have been freestyling by myself for almost 20 years.

I also have good connections in the rap world. Not enough that I’m going to get a free pass or anything, but I am very confident that if I made an album I was proud of, I could get it in front of some of the top labels, producers, etc.

My thesis is that the rap world is pretty weak right now, and that I have all of the time in the world to make a rap album. Most of my time is at my discretion and I’ve built really good work habits. It is nearly inconceivable to me that I couldn’t make a really good album in one year. I have a lot to learn, but I think I already have some relevant skills.

If I do this my goal would be to create a rap album that I liked and to open for a B-list rapper or better. I think the biggest challenge would be finding my unique voice/angle, but I have some ideas on it.

2. Build an Art Museum

There was an artist called Ogata Gekko who I really like. He made Japanese Woodblock prints around the turn of the 20th century, and his were the first woodblocks that really drew me in and made me learn about the art form.

I first saw him in the Honolulu Museum of Art (excellent musuem!), and immediately checked online to see if maybe one day I could afford one of his woodblock prints. I was shocked to find that many were around $100, and I bought one.

Now I have several of them and am always on the lookout for new good ones.

I am thinking about building the Ogata Gekko Museum of Asian Art. It would primarily be his work, but I could also have works from other artists.

The idea behind this one is that for somewhere in the realm of a few thousand dollars, plus working out a clever deal for some space, I could actually run an art museum. His stuff is respected and famous enough that most major art museums have some, and I think it’s really relatable for visitors. I would buy all the art myself and put it on loan to the museum, so that if it all fails the worst case is that I have a lot of art that I like.

I suspect that having an art museum would open a lot of doors. Maybe I could loan my art to other museums. Maybe they would loan me their art. Maybe it would just put me into some interesting circles. I’d have a cool space that I could use to help educate people on art and even do things like Japanese tea ceremony.

I’ve actually started working on both of these, to see if either of them really grab me. I’ve written a couple raps, have written ideas for many more, and have begin writing down clever or funny lines I come up with when I freestyle. I’ve also started buying many more Gekkos when they come up for sale.

Who knows if I’ll do either or both, but it’s a useful exercise to think outside of the box, even if it’s a rather large box you’ve created for yourself.


Photo is from a Justin Timberlake concert…. or maybe of me performing at a rap concert in the future. Who can be sure?






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