Tim talks about his life being a series of 6-month experiments and 2 week evaluations, and some other bits at the end. In response to a question from a listener about how one can decide what passion or vision they should follow, Tim responds by with the above, and that the term passion (and vision) is loaded and almost meaningless. He instead goes on to say that a way to quickly narrow down to a few options that which you might want to pursue for say a 6-month experiment is as follows: list out the things that you (think you) are better than your friends at. And there’s a start.

This got me thinking about this same thing for myself. As I find myself nearing a crossroads where I’d like to really shift into a similar trial by experiment type of world. Traveling and geo-arbitrage included—rather, emphasized.

Here’s my list:

I’m really glad that Tim brought up the concept of pick something that you’re better than your friends at. It gives you motivation to at least start somewhere. It’s so easy in the digital age to quickly find a video of someone doing what you’re trying to do, but 10x or 100x better than you already, and then getting discouraged. However I think that there’s something to at least starting and getting out there. For instance, if you read a good book on how to be productive, and then want to become a YouTube personality and start releasing productivity videos, but notice that there are 20 people already there and some of them have 100K subscribers, you might be discouraged. But if you have the motivation to start, and the knowledge that you will be helping someone in some way, as well as helping yourself…and the understanding that you are in an experimental mindset, and that you will learn and grow and become better with practice… then you will actually start, and actually have a chance to become that 10x / 100x performer.

I’m leaning towards heading out from this current experiment to start a new one.

My major concerns are really two:
1. The fear of loss of some intangible feeling of interpersonal equity that I’ve built up by taking on this job.
2. The financial aspect that I will have no guaranteed income for an indeterminate amount of time.

Mitigating factors for these two:
1. I had quit this organization earlier this year with the intent never to return. I took on a snap job just because it sounded interesting. It is interesting, and very high visibility. But it has a lot of the same elements of the overall organization that I disagreed with and encouraged me to leave in the first place. And the job hookups for the future would be (likely) similar to the environment I’m in now.
2. Not super worried. I do have some income sources, but in order to make this lifestyle permanent I would need to develop a source of income, preferably automated. Lest I be forced to capitulate and come back to some type of 9-5. I think that’s what I really fear the most… having to revert to a 9-5 or something just to make ends meat. But with this new experiment and geo-arbitrage I’m looking forward to I don’t think this would be a huge concern. I will make it.

There are other, more administrative concerns, that I can easily bulldoze through on a weekend of planning, but the two above are really the only things stopping me.