How I Choose What to Work On

A reader, “Moo”, asked me to write about my process for entrepreneurship and how I choose what to write on. Despite being a lifelong entrepreneur and being relatively successful at it, I don’t write a lot about it because I routinely make decisions that trade money for other things (freedom, autonomy, quality of life, stubborn insistence on what I want a product to be, etc). I suspect that most people who want entrepreneurial advice are more interested in making money than the things I prioritize.

I don’t really even know if I’d suggest my method for other people, since it’s pretty tailored to me and my preferences, but I’m happy to share it in case it gives anyone anything to think about.

If there were a core principle of my method, it would be that life is amazing and my goal is to maximize experiencing life. You need a certain amount of money to do that, and increasing amounts of money make even more things possible, but often these come at the cost of increased stress, reduced time with loved ones, or doing work that doesn’t matter to you.

With that in mind, I will only ever work on things I want to work on. I would rather be poor than make a lot of money doing something I hate, and I think my history of actions (readable on the 15+ years of blog posts I’ve written) prove that. If I were giving advice I’d probably encourage someone to choose the most profitable thing out of all of the things they want to do, but that’s not necessarily advice I’d follow.

If you do something you love, you will become good at it much faster than something you don’t love, and when you are good at something you will have some opportunity to commercialize it. For example, I blogged for many years making zero dollars, but I did it because I liked doing it. Then I wrote books because I wanted to get some ideas down, and blog readers bought those books. So even though blogging didn’t seem to have any commercial potential, it ended up making money in the end. I don’t take new clients anymore, but when I was spending time coaching I was able to make $500-600 an hour. Pretty good for a guy who just writes about how he lives his life and offers some guidance to others who want a similar path.

When I first built CruiseSheet, it never occurred to me that it would make money. I just wanted to have a list of cruises ordered by the best price per day, and as I chipped away at it week by week it eventually became a real successful business.

Of course, many other things I’ve done, even those that seemed like they could make money, didn’t make anything. I spent a lot of time building a new blogging platform that I wanted to exist, and it eventually died after making no serious amount of money. I spent months designing the most realistic fake candle, all of which are in my own house. I made a social task platform and got a reasonable adoption, but never crossed the gap to making money on it.

Most people choose money first, I choose activity first and then try to find a compatible way to make money on it. If it makes sense and works, that’s great. If it doesn’t, it doesn’t really matter because I wanted to do it anyway.

Part of the reason I’ve been able to do this is because I’ve always designed my life such that it can benefit from having money (pinball arcade rooms and all that…) but is also compatible with having no money. For around seven years I lived on the side of the road in an RV and spent most of my money on the cheapest flight deals I could find, and this was well before #vanlife was fashionable. The truth is that I was no less happy then, mostly because the important aspects of life (time with loved ones, working on meaningful projects, etc) were fulfilled. Part of why I don’t preach my method of entrepreneurship more loudly is because I know most people aren’t willing to live that lean.

On the other hand, I am always willing to charge for what I do. It seems that a lot of people who work on what they want to work on never feel comfortable charging. To me that feels like the right flow… work on something because it matters, and when it can create enough value for others, get rewarded with some of that value.

Once I have a business, my priority is to make it the best possible option for the user, even if that means I make less. For example, at CruiseSheet we include the taxes and fees in the price. No other cruise agency does that, so I’m sure we lose a lot of head-to-head comparisons, but I don’t really care because I think it’s disrespectful to a customer to sneak fees in at the end. When I screened people for coaching I would say no to people who I didn’t think I could deliver overwhelming value for, and have encouraged people to quit if I think it’s in their best interest. My judgment isn’t always right, but it makes life simple when the method is “build the right thing, charge something reasonable”.

Within each business, I consider top priorities as well as what I most want to work on. For example, in CruiseSheet I spend a lot of time building out small features that don’t really matter but that are interesting to me. I like to think that they add up to make a nice site, but maybe no one ever notices. If something becomes urgent, though, I will focus on it. Last month we had an email deliverability issue that caused some major customer service issues, so it was all hands on deck to close out tickets, make things right, and to build better systems for the future.

Most of the time I work on what I want to work on, but since I do like success and having the business grow, I’m often most excited about some sort of task that has profit-generating potential. My more successful entrepreneur friends would probably disagree on that point.

I also spend a lot of time not working. I’ve seen enough people burn themselves out and waste all day doing unimportant tasks that I don’t feel tempted to fall into the same trap. I generally do some productive stuff every day, but I also play pinball any day I can, spend 1-2 hours drinking tea, sleep a full 8 hours a night, spend time with my wife, use the steam room and pool, etc. Besides just ensuring that I have a good life, this keeps me fresh and motivated, and gives me a lot of slack if something urgent comes up that needs 8+ hours a day.

Because my methods are based on principles (or maybe some sort of genetic presets), they haven’t changed much as I’ve become more successful. Other than a three year stint where I worked like crazy, mainly to build the habit and learn how to do it, this has been my attitude. Fulfillment, satisfaction, and mental health always comes first, and then traditional success comes next. I certainly haven’t reached the levels of financial success that some of my friends have, but I don’t envy them either. They’ve made the trade-offs that are right for them, and I’ve done the same.


Picture is from Nanortalik, Greenland! I went on a cruise there with some friends and I jumped in the ocean and swam to an iceberg with my friend Todd!

I’m on another cruise (A 27 day from Los Angeles to Sydney via Honolulu, NZ, and a bunch of South Pacific islands), so I’ve got a lot of time to write blog posts. Send me questions and I’ll make them into blog posts…






10 responses to “How I Choose What to Work On”

  1. Adam Ruggle Avatar
    Adam Ruggle

    Thanks Tynan, I appreciate hearing more about your mindset and hope you enjoy the extended cruise.

    1. Andrew Avatar

      Tynan, I appreciate this article as well and getting into your mind set about what you work on. How do you choose what is “worth” the money to trade money for whether it is autonomy, quality of life or other things?

  2. Gavin Avatar

    More mindset posts would be appreciated. I was reading a Scott Young (or possibly Cal Newport) article about goal setting, and how he broke it down for a complete beginner was interesting. Good goal setters have such discipline that it’s easy to dismiss the advice to ‘just do it’, because that is what they habitually do (as do their friends and social group).
    I wondered if there were any habits or mindset that you have, that when you meet people outside your social circle, they struggle to comprehend something that you think is normal. I know this is a difficult thing to answer, and you’ve briefly tocuhed on it before in your podcast and others articles (such as you not buying into advertising). Cheers, Gavin.

  3. Adam Avatar

    I’d be interested to get an update to this post: considering the current landscape of interest rates (IBKR margin rates are now 7% or more)

    1. Tynan Avatar

      Might write one, but a quick update: I no longer use margin heavily, except as a buffer against overdrawing my checking account, which allows me to keep more of my money invested. It’s just not right for this high-interest climate. My investments are still the same, though.

  4. JR Avatar

    This is where you have contributed a lot of value to my life and I’m sure the lives of many others – by living and spreading this mindset and a comfort with making unconventional life choices based on certain core principles. You have been an inspiration for many and a trailblazer. That is true ”success”.

  5. Mads Phikamphon Avatar
    Mads Phikamphon

    Since you are asking for questions, I would love to hear more about Cruise Sheet. Especially how you have grown/done marketing for Cruise Sheet (I have a site for finding model trains and it’s suffering from me loving programming far more than marketing).


  6. Alex Avatar

    New Kit list ?

  7. Miguel Marcos Martinez Avatar
    Miguel Marcos Martinez

    Kevin Kelly nailed it when I heard him say something like “The only productive way to answer what should I do now is to answer the question ‘who should I become’? Succinct and meaningful.

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