Once you’ve found success building and selling something on the internet, no matter how small, the incentives of the internet machine will nudge you to think that the most important thing is to optimize, scale, and grow.

That may be the right path for you but I want to convince you that there might be another path.

I want to share my version of how I’m playing something Packy McCormick calls the “great online game.” A version that focuses on building a life where 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 a full-time job.

What follows are five principles that have emerged that have guided my path. They have emerged slowly and organically. Only now do some of them seem obvious. I fully expect that they may morph over time. These principles serve as a compass for me as I navigate the infinite possibilities of the internet.

I think that nearly everyone, including people on the default path, should develop their own principles. This is because the stories of how we think about our work and lives are outdated, one based on a 1950s reality. This story worked in a time in which people worked for one company in their life when growth rates of 5% were normal, and most women didn’t work.

The trap of this story is that it actually works in the first few years of anyone’s career. Many companies still believe in this story and this is why the first five years of your career are still filled with promotions and a clear career path. Anyone that’s made it past that point, however, knows the truth. That there aren’t many clear career paths left and because of slowing growth rates, competition and politics are more central to getting ahead than some may think.

Developing your own principles and strategy is the only choice left if you don’t want to play those games. For the self-employed, developing your own game and set of principles is not a choice but a necessity. It is the only way to survive over the long term.

Here are five principles that help 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 two straight years.

After a strong year of sales, 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. I was even invited to an accelerator program for proven course creators to make this happen. I could see the path and had a reasonable level of confidence that I could 4-5x my course sales if I wanted to.

But then I challenged myself, “what would you do once you had that money?” I realized I would write. I then reflected upon the fact that I could simply do that now. I was already making enough to support myself and still save a little money each year.

With this in mind, I decided to make a commitment. In 2021 I would write a book. This would be a way to commit to what I claimed to care about and also be a way of testing out this principle of “coming alive over getting ahead.”

My course has remained steady but has not grown much more than the previous year. However, the act of committing to writing a book has been one of the most thrilling commitments of my life. I’ve never felt so alive, challenged, and excited about anything I’ve worked on.

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 plan to walk away from that choice.

Principle #2: Don’t Be Attached

While my online course continued to succeed, I realized that I had come to expect that income.

With a few hours of maintenance per week, I was able to keep a profitable business running while writing my book and studying Chinese full-time for a three-month stretch. In one of those months, I even worked with a client to run a four-week consulting skills bootcamp which led to my best month since being self-employed. Then in May, the sales of my course tanked, likely driven by a change in the google search algorithm, people returning to the office after covid restrictions, and travel for the summer.

These kinds of ups and downs would be terrifying if I had a high fixed-cost lifestyle or if I had not experienced them before. To anyone that’s been self-employed for a long period of time, they learn to deal with these shifts. Here is an example of some various swings in different income sources I’ve experienced over the past five years.

With this in mind, I try to make sure that I’m not assuming that any of these income sources are permanent. I’ve embraced a visualization exercise where I go through an exercise of visualizing all my digital properties and revenue streams evaporating and then asking “am I okay?”

When my consulting course struggled for a couple of months after doing so well for more than a year, I was able to reflect on the fact that I’ve started from scratch in the past and I could do it again.

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

About a year into self-employment I realized I really want to stay on my path longer than my initial plans for a one-year experiment. I realized that if I wanted to commit to this path, I needed a better strategy for earning money than only freelancing.

Freelancing is one of the best ways to get started with self-employment. It enables you to leverage your existing skills while giving you more flexibility with time to spend on other things you want to work on or to simply work less. This worked well for me. I had much more time to work on creative projects but realized that following that path was a lower-income and precarious version of my previous path.

I wanted to embrace an antifragile approach, one in which I would not be as susceptible to stretches without income or to shocks in the broader economy. Freelancing is one of the best ways to make money in a strong economy, but it’s also one of the quickest things to disappear when companies are cutting costs.

With that in mind I set out to focus on two goals:

  • Earn money in as many different ways as possible
  • Build a portolio of income streams that act as a high probability “floor” of income

This lowered my income in the short term but boosted my confidence and resilience. Knowing how to make money in a number of different ways gave me practical skills and an expanded imagination about what I could do to make money.

While I had a hard time realizing it at the time, my overall income also steadily increased over time with this approach. I now have had at least three sources of income generate over $200 for more than a year and have had at least six income sources for longer than that.

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 and three months with more than $10,000 per month. 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 and experimenting. I find the process of turning ideas into my head into things that can be helpful for others to be fun. This is a unique advantage in the world that is emerging and I’m fully aware of this.

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 shared in this conversation with me – any one of which could have unexpected payoffs.

With my newsletter and podcast, both started as ways of sharing what I was up to and without any intentions of turning them into businesses. I didn’t promote them or share them widely because I wanted to be able to quit without people noticing. Tim Ferriss took this strategy with his podcast. He told himself that he would do six-episode and if he was having fun and didn’t hate it, he would keep going.

Conventional wisdom says to grow fast, to take advantage of every launch. However, that increases the odds that you end up doing something you don’t want to do. My approach has been to take a slower path. Five years into this journey, almost everything I’m doing I want to be doing and this has been from a series of incremental “yeses.”

I recently launched a freelance consulting skills course. This course was the result of helping a couple of freelancers that were doing work for me level up my skills. I realized I was having a lot of fun helping them be better and they were finding the information and feedback useful. I had validated both the idea and the feeling. That second part is often ignored. Too many people don’t think about the fact that once they build something that makes money, they have to spend a lot of time doing that thing. I only built the course because I enjoyed helping people become freelancers. Right now it’s still a small bet but when the opportunity emerges to take it somewhere else, I will consider it and if it feels right, I’ll say “yes.”

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 proactively volunteered to help fix people’s computers and help with resumes, job searches, and interviewing. After I graduated I helped people make career changes and write essays for grad school. At my jobs I always took on extra roles to help with training and coaching.

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 you balance yours gives with your takes. 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.” Eventually, I realized it was better to create my own game rather than try to swim upstream.

So I experimented. I started a career coaching business on the side. I started writing. I eventually went out on my own and was able to be the kind of freelancer I wanted to be. I had more time to spend helping people for fun without feeling like an idiot (though sometimes it still feels silly to do things for free).

As I continued to do this and built an audience through my writing, people starting sending me thank you notes. I received one note from someone that I had a conversation with a few years earlier. She told me that her conversation with me completely changed her mind on what she wanted to do. Now she was doing something she loved and wanted to thank me for the inspiration. I’d be lying if I said that these 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. Appreciation was something that surprised me but it felt true. Leaning into that and realizing that it is something I need but can also be fuel is a powerful thing to know.

A couple of years ago I did another exercise in which I had to write down my “purpose.” The person that created it said to keep writing versions until you cry. I thought it was silly but I’m always open to trying new things. It worked and this is what I landed on.

Connect as a real friend to people to give them the courage to create, help simplify the world to enable people to imagine new possibilities, and continuously be more brave in discovering the people and things that matter in my own life

I know that my desire to help others might be a little pathological and after reading Adam Grant’s Give and Take it seems that I’ll probably succeed financially a little less. But I don’t buy his argument that this is something to fix. I have realized that I want to design a life around making this weird quirk a great part of my life. I know that it undermines my ability to be financially successful sometimes and that’s okay.

I’ve just decided that it 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 way more fun and I hope I’ve convinced you to find your own game worth playing.



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