How I Choose What to Work On

I get asked often how I choose what to work on. From the outside, I can see why people ask. The projects I work on are fairly wide-ranging, from coding CruiseSheet to writing blog posts to random adventures and building things.

Things make a little more sense when you understand that making money is only a secondary priority for me. I do like to make money, but I will never do something I don’t want to do for money. Google could offer me $1M for a year of work, which is a life-changing amount of money to me, and I would not take it.

Now, that’s a massive luxury. Through mostly sheer luck, I happen to be in a position where I can do whatever I want and survive. I have few expenses and some skills that ended up becoming valuable even though it wasn’t at all clear they would be when I began learning them.

If I had a family and I needed to put food on the table and didn’t have the skills I have, I would gladly mop toilets to provide. I don’t believe that I’m above any sort of work. The point is that along the spectrum of trading freedom for money, I’m way over on the freedom side.

I don’t recommend that you prioritize freedom over money any more than I recommend you like blue better than red. It’s an entirely personal preference. I think it’s important to recognize what your preference is and to live in accordance with it.

To be honest, I don’t even care whether my work is likely to make money or not. The first version of CruiseSheet, which still underpins the current version, had no way to make money. I wrote my blog for many years without making a dollar from it, even indirectly.

I love working for work’s sake, and I like doing things other people aren’t doing. If you look at all of my current projects, they follow that. No one has built a cruise agency like CruiseSheet. My books are pretty unique (though not entirely). While there are a lot of coaches out there, I suspect that the type of advice I give is very different.

When I am really excited about a project or really want a certain outcome, I find it easy to pour my time into it. I don’t need much motivation, and I tend to do my best work. My feeling is that if I am fully engaged in something, I am most likely to create something that is valuable to others.

At the same time, I like money and I recognize that the easiest way for me to get money is to monetize the things I work on. I try to do that in a way that is a clear win for the person paying. CruiseSheet always offers the lowest prices I’m contractually allowed to offer. My books are pretty cheap. My blog is free, but once in a while links to something that earns me money. My coaching is expensive, but I have a long track record of producing great results for people.

To the absolute infuriation of my marketing-minded friends, I don’t spend much time on marketing. When I write a book, I just plop it out on Amazon, write a blog post, and move on to the next thing. I usually don’t even link to my coaching page when I mention it in blog posts. The truth is that if my life was full of marketing tasks I would enjoy it a lot less, so I’m happy to take the financial penalty.

I’m not sure there’s any actionable advice in this post. If your priorities are like mine, I suspect you already have a similar decision making process. If your priorities are different, you should probably be doing something different. But at least now it will make sense when I open an art museum, put out a rap album, or spend a year making the best LED candle ever made.

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Photo is a weird piece of art at the Frieze festival in NY. Pretty funny scene there, but there was some good art (not sure I’d count this in that category, but I thought it would make a good blog photo).