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.
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).
For about three years I worked really hard on a startup called Sett. It's a blogging platform that did a lot of things very different, and, in fact, is still the blogging platform that my blog runs on because I'm totally unwilling to give up the features that I've gotten used to.
At the same time, it was a commercial failure, barely making more money than it cost to run the servers, and certainly not enough to compensate Todd and I for the work we put in.
I also run a site called CruiseSheet. It's not wildly profitable, but it does consistently turn a profit, and I even have an employee to do all the daily tasks. These two startups are very different, and I've learned a lot through doing them.
The first thing I learned is that traditional "startups" are overglorfied, at least from my perspective. They seem to have morphed to become quite formulaic, and VC money has essentially turned them into "create your own job" instead of "create your own business". Obviously this is speaking in broad strokes, but it's how the definition seems to have shifted in San Francisco.
This month I started writing down my goals for the very first time. There have always been things I really want to do, but somehow I never bothered to write them down. At first I thought I was just being pragmatic. After all, I already know what my goals are. How is it going to help if I write them down?
But now I've realized that I was actually scared of the future. Writing down your goals forces you to look into your own future, and that can get scary. Not only do you have to know what you really want, but you also have to confront the idea that it's not going to happen unless you start working towards your goals.
I've always wanted to start my own business. Ever since I remember myself, I've been daydreaming about being a successful entrepreneur, being my own boss, and more recently, making a positive contribution to the world. But the ugly truth is that none of this is going to happen unless I start taking action right now. Writing down my goals forces me to confront the harsh reality and actually start working towards my future.
I know that things will get tough at some point. They always do. But persisting through hardship is what separates successful people from those who never manage to get anything done. I've learned this myself the hard way. But now that I write down my goals, I know exactly what I'm struggling for. And I won't stop until I get there.
I write down my yearly, monthly, weekly and daily goals. Most of my monthly goals are small steps towards my yearly goals, my weekly goals are small steps towards my monthly goals, and so on. If what I'm doing this month won't help me get where I want to be at the end of this year, should I really be doing it?