Principles For The Long Game | #146

aka the great online game...

June 26th, 2021: Greetings from Hualien. Lockdown is extended a few more weeks here but the cases have been dropping. Hopefully, things start looking better next month.

🎧 I published a podcast episode with Jenni & Lisa Dazols, a nomadic couple from San Francisco who has spent the last year in Taiwan with their two kids. We talked about leaving their jobs, living abroad, self-employment & financial fears


Principles For The Long Game

Once you’ve found success building and selling something on the internet, every incentive nudges to double down or shift to teaching others to do the same.

This game doesn’t interest me. The version of the great online game I am attempting to play is one in which I build a life in which I can work in different ways to pay the bills, have plenty of time for creative pursuits, and don’t have to be tied to full-time job. I will share the rules that have emerged overt the last four years but I don’t advise trying to play my game. You should develop your own.

The reason to develop your own game with unique rules is that most of us are unconsciously opting into the default story of life and work, one based on a 1950s reality. This story increasingly falls short and has made us a bit blind to the fact that almost everyone with a knowledge economy job is already working 100% remotely, with slight differences on where people are allowed to sit Monday through Friday.

This story still works well for the first few years of anyone’s career but struggles to match the reality of how most people live. Developing your own principles and strategy is the only choice left if you don’t want to feel the tension between how you want to live and what society is making you feel like you should do.

For the self-employed developing your own game is the only way to survive over the long term but for more and more people on what appear to be traditional paths, this is the only way you will be able to stay sane too.

Here are the five working principles I’ve developed to guide my path.

Principle #1: Coming Alive Over Getting Ahead

In April of 2020, my strategy consulting skills course started taking off. This was a weird moment because it took off at the same time I started dealing with extreme fatigue following complications from a tooth extraction. My course was selling like hotcakes and I was either wandering around the canary islands talking to doctors or sleeping in bed. This is one of the weird things about being a self-employed creator. Your financial reality can shift dramatically in a short period of time and often due to things outside of your control.

I had spent hundreds of hours to get it to that point but it was never my intention to hit a monthly revenue goal. I genuinely thought it would be fun to figure out how to create an online course (If you want to go much deeper, the full story is here). If you had talked to me in January of 2019 you might have thought my principles of keep doing stuff I like, give generously, and don’t work too much were pretty stupid because I had made less than $3,000 doing so in a year. Two years later I’ve somehow made a decent American salary for the last couple of years.

In December I reflected on my success with StrategyU. My inner consultant knew that the obvious solution was to double down, add more courses, level up the marketing, create more content, and see where it goes. But I decided that writing a book and learning Chinese were a little more interesting.

If a choice emerges between spending more time on making money but means I’ll have to cut back on some of the things I like doing like learning, writing, and connecting with people, I tend to walk away from the upside.

Principle #2: Don’t Be Attached

For the last six months, my success with StrategyU continued. With a few hours of maintenance, I was able to keep a very profitable business running while writing my book and studying Chinese full-time. In April, I had my best month since I’ve been self-employed. Then in May, something changed. My sales nearly evaporated. It was likely a mix of remote work ending in some places, platform changes for ads from ios, and marketing strategies that are no longer working.

These kinds of ups and downs would be terrifying if I had a high fixed-cost lifestyle and had not gone several months in 2018 without making any more. It would also be more surprising if I had not seen these kinds of swings in other things I do (with varying levels of control):

Every month I go through an exercise of visualizing all my digital properties and revenue streams evaporating and then asking “am I okay?” Seeing my consulting course struggle for the past couple of months has made this real. Earlier this year I thought there was a chance that I could double my success of last year and this week I am hoping for 70% of last year’s results.

But I blew it up in my head last month already. I prepared for this.

Principle #3: Build An Income Floor & Optimize For Income Streams

About a year into self-employment I realized I wanted to extend my path indefinitely. I realized that freelance consulting was becoming a more precarious version of a full-time job and that I needed to lower my risk. I decided to shift away from consultant towards trying to make money in a bunch of different ways.

This lowered my income but boosted my confidence and resilience. Knowing how to make money in a number of different ways gives me practical skills and an expanded imagination when it comes to adapting to the world and what I need to do to make a living.

This strategy does not correlate with steadily increasing income but it has raised my income floor. In my first year of self-employment, I had high earnings but it was inconsistent. I had six months with less than $2,000 income. The second-year I shifted away from consulting and had seven months with less than $2k income. The last two years? I’ve made at least $2k every month.

This is much more valuable for the game I’m playing as it dramatically lowers the odds that I will run out of money and gives me more freedom to walk away from any type of work I don’t want to do without feeling like I might go broke

Principle #4: Start Slow & Keep Trying Things

I like trying a bunch of different things for a few reasons. First, I genuinely like creating new things. I find the process of turning ideas into my head into things that can be helpful for people's fun. Second, it keeps things interesting and also exposes me to a number of different ways of engaging in the world such that I can help others do the same. Finally, it helps me build a portfolio of “small bets” as Dan Vassallo has written about - any one of which could have unexpected payoffs.

With this newsletter and my podcast, both started as ways of sharing what I was up to. I didn’t promote them or share them widely because I wanted to be able to quit without people noticing. Conventional wisdom says to grow fast but that increases the odds that you end up doing something you don’t want to do. For the most part everything I’m doing now has been from a series of incremental yeses.

Later this month I’m launching a freelance consulting skills course sharing how I work with clients and learnings from working with some of the freelancers I’ve hired. This might seem insane to you if you only knew about the recent fragility of my other course but given my game, I hope you can see what I’m up to.

I’m launching the course as a small repository of lessons and case studies on how to do freelance as an ex-strategy consultant approaches freelancing. So far 34 people signed up already so it seems like there is some interest. If I have fun doing it and there is demand, I’ll expand it. Maybe next year I’ll be writing about how this course took off in 2021.

Principle #5 Make Friends. Be Helpful

This is the most important principle and the one that makes everything else more fun. Yet, it is also the one where I struggle the most.

I’ve always been the person that likes helping other people. In college I helped fix people’s computers and help get people jobs. After I graduated I helped people make job changes and update their resumes. At my jobs I always took on extra roles to help with training and coaching other people.

It was fun. But the world tells you that these are silly things. People tell you, don’t get taken advantage of. Adam Grant writes books showing how to avoid being a pathological altruist and to make sure your transactions are fair. Others ask “why you don’t charge?” You spend your time at work helping your struggling colleague while you watch the skilled politician land another raise.

I was cynical about this for a while. I wanted the working world to change. I wished there were paths for people to progress and get raises while remaining a front-line manager. My first blog was called “better working world project.” I was naive, that’s not how it works. You can only be nice and generous despite the incentives and I didn’t have the energy to swim upstream.

When I left and started writing more people were writing me notes thanking me for what and telling me to keep going. A few times I’ve received notes from people a few years after they read something I said or after talking with me and telling me that I made a difference in the their life. Those moments are fucking awesome.

I did an exercise in which I had to rank my “yearnings” or the things we really crave. My top two were appreciation and freedom, which is to say I give because it helps me meet one of my needs. It’s just that its a lot easier to do on my current path.

I know deep down that my need keeps me doing things that undermine my ability to make more money and I feel silly about that a lot.

Yet I’ve decided its something that matters

The Bottom Line

I don’t know what will be paying the bills next year but the longer I play this game the more confident I become. It could all blow up at any second, but the whole point of the game is to enjoy the journey. I spent ten years on a path where I was always focused on the next project or the next step.

This is more fun and I hope you find your own game worth playing.

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