When I listen to my own podcasts, I am often surprised at how I don’t fully remember everything from the conversation. This can be embarrassing until you realize that this happens in many conversations. We remember how we feel during rather than the words being spoken.

I recorded an episode in 2021 with a friend, Kris Abdelmessih. After finishing the conversation I remember being excited about what we talked about but it wasn’t until listening to it a second time that I realized how many great ideas I took from the conversation.

What follows below is a link to our conversation as well as eleven ideas that resonated with me.

Meet Kris

Kris Abdelmessih has one of the most unique perspectives on life and works I’ve stumbled across in the past few years. He uses his experience as a trader to look at decision-making and work investments through the lens of options, pricing, and other financial models.  I enjoy his perspective – unlike other financial types, he seems to have a proper appreciation of non-work / non-productive time.

We explore his recent break from trading, his creative journey writing on the internet, and finding his people, and he challenges me to think differently about how I’m spending my time with my work.

The conversation dramatically shifted how I’m thinking about the possibilities of my path.  If you are on a self-employed path, this is a must-listen. We talk about:

  • Financial insecurity and its relationship to the creative path
  • Using creative pursuits online to make friends and make your life better
  • How to think about the options in an emerging space like the creator ecosystem
  • The challenges with using an “options mindset” to make career decisions
  • His experience spending time and teaching kids
  • Brainstorming options for his next adventures with work

Eleven Lessons On Valuing The Solo Path

#1 I used to believe in Creativity, Inc.™

Early in my career I never thought of myself as creative. Creative people had titles like “creative director,” or sold paintings, or did crafts with their friends.

Now I realize that turning information into stories that resonate with people is also a certain kind of creativity. One that I can use in many different ways and that I can improve at over time.

Another kind of creativity is being able to navigate modernity. Landing interviews, figuring out how to complete bureaucratic tasks, and getting accepted into grad school all require a certain kind of creativity. I don’t like being creative in this way but can I do it? If needed.

#2 “You realized you didn’t have to be dissatisfied”

You don’t know what you don’t know. When I was working on my former path, I thought that being dissatisfied was part of work.

On the podcast, Kris said to me that on my current path I learned that “I didn’t have to be dissatisfied.” I never thought about it that way.

I’m not sure what this is worth but it’s definitely a superpower for knowing when to stay no to the projects that might drain my energy.

#3 A job is a kind of work where its harder to get fired

When I was employed I didn’t behave as if this were true. I worried too much about doing what everyone else was doing instead of putting all my energy into doing the things I was good at. It’s clear now that if I took a job I’d behave much differently.

People undervalue looking at life from different perspectives and this is one of the biggest reasons to experiment with structuring your life in many different ways.

#4 Turning a one-way door into a two-way door

Many people fear leaving their jobs because they might not be able to ever get their jobs back. Some believe that if you leave for too long no one will hire you. This might be true in some places but it is definitely less true than in the past.

Almost everyone that leaves their job or embarks on a new path almost immediately recognizes the one-way door that they thought they walked through is definitely a two-way door. Many people continue to dabble in that old world either as freelancers or on their own but many never end up going back through it.

#5 Undervaluing Space

Kris was surprised by how valuable it was to take time just to think and reflect on his life. Something about full-time work makes this hard. Or at least, that was my experience. I’ve written about valuing space and my experience in the first few months in Taiwan, where I couldn’t find any work and embraced the opportunity to walk around and read in parks.

On my current path, I build in sabbaticals and extended breaks because I know that is what keeps me energized. I haven’t come close to burning out or considering leaving my current path once and continuously cultivating time and space for reflection is a big reason why.

#6 You play the games that the people around you play

We both reflected that we got sucked into money and promotion games that we never would play now. Before I left my job I was fighting for a promotion and a raise and was upset that they were not giving it to me. I haven’t made 50% of what I made in that job in almost five years but I have plenty, I’m happy, and I know for sure I’d never play those games again.

#7 Cutting expenses is lowering your cost of personal capital

When I first quit my job in New York and again in Taiwan when I couldn’t find remote freelancing work, I cut my spending a lot. The story I told myself about this was about financial fears and insecurity about money.

Kris said. “oh you were lowering your cost of personal capital.”

I like this lens. From this perspective, anything I spent my time on would have to meet a much lower bar for “approval” by the internal investment committee in my head. When your personal cost of capital is low, you can “invest” in much riskier projects and ones that can’t be valued clearly.

This was probably one of the biggest reasons I was able to make a shift from freelancer to the creator economy stuff I’m making money from now.

#8 “If you make money every day you are leaving money on the table”

Kris shared this popular quote in trading circles. It resonates with how I’m trying to approach my path. When many people talk about leaving their jobs, they talk about their desire to “replace” their income.

If I had focused more on freelancing I could have done this. However, I realized within a year that I wanted to play a longer game and learning a bunch of different skills, finding work I liked doing and living in different ways was going to help me much more in the long run.

#9 Translating “normal” expenses into dream life scenario expenses

Self-employment exposed a clear tradeoff between money and time. When I see a car, I see the equivalent time I could spend not working. When I hear about a home someone has bought I think about the life experiences it could buy me instead.

There are a lot of Teslas in Taiwan. When I see someone driving it on a commute from the office, all I can think about is the two or three years traveling the world that money would fund instead.

If you start to think about a lot of purchases like this, pricing them in the “dream life” scenarios you imagine, it might expose hidden possibilities in your life right now.

#10 Portfolio Theory of Indie Creation

One of the most interesting examples Kris shared was a perspective from portfolio theory. If you are thinking about creating something as an individual, it can be easy to overlook the value the higher value it might have if it were part of a broader portfolio of content.

For example, he could create a course on options trading and it might do well but if he did this for a company like Robinhood it might have even more value for both parties.

I value working on my own but this made me realize I’m probably a bit blind to obvious opportunities where I and another person or company would both be in better positions if we figured out how to partner.

As more people become self-employed, enter the creator economy, and dabble in this broader new economy, the possibilities will continue to increase. Developing a better view of how I might fit into all of that is going to be something I reflect on more deeply in the coming months.

#11 “highest and best use is…”

Kris mentioned that it’s clear that the economy says his “highest and best use” is doing something in finance but he has a hunch that he hasn’t quite figured out his broader highest and best use.

To me, this seems like the ultimate and real work of our lives. Many people are content to accept the economic answer (and for some people that may be their best use) but I am not. I have a hunch that my highest and best use is continuing on this journey and seeing where I might be useful along the way.

The hardest part about this is that if you don’t let the economy decide, you can’t measure or prove that you are right.

Jeremy Finch from The Fire Jar Summarized This Convo Too


Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here



    Want To Join 5300+ People For A Weekly Reflection On Work, Life & Philosophy?