The Golden Algorithm & Dancing With Uncertainty | #265

May 18th, 2024: Greetings from Austin!

+Pathless Path Meetups: In Mexico City Meetup on June 6th and Boulder sometime in July (date TBD)

+Alternative Parenting & Education Paths Research Group: I’m spinning up a pop-up research group for parents exploring alternative paths for raising and educating kids. Sign up here.

+Book: Pre-sale is live. The cover and details will change but link is here.

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#1 Golden Algorithm

The biggest benefit of embracing a pathless path is that it forces you to make decisions with uncomfortable emotions rather than making decisions to make them go away.

I didn’t have the language to describe this shift until listening to many of Joe Hudson’s Art of Accomplishment podcasts. In this one, he details his “golden algorithm,” which he has described this this three-step sequence:

#1 Name an unwanted emotion in your life.

#2 List the ways you try to avoid it

#3 Notice that every way you try to avoid it, you actually create it.

For me, this played out over and over and over again in the workplace during my full-time job era. My approach to “solving” some of my younger insecurities was to do impressive things. For ten years I jumped from job to job trying to reach some level of winning:

In quitting my job, I came face to face with a flood of emotions. It felt shitty.

I had the sense that I was doing something wrong. That I was not good enough.

But I also knew that the thing that would make me feel better, getting a job, or even going all-in on freelance Paul, was something I was not intending to do.

So I stayed with the feelings of not feeling good enough, feeling like a fool, feeling like a failure, and feeling insecure about my path….

…and eventually, it was sort of fine.

Joe has this phrase, “Joy is the matriarch of a family of emotions. She won't come into your house if her children are not welcome.”

The longer I spent on my own pathless path, the better I felt. And it was better than anything I ever felt in my twenties. It was shocking. It’s still shocking.

In my twenties, I described myself as happy. I was happy in a sense. But I was spending A LOT of effort making sure I always felt good. Between the busyness, weekend binge drinking and partying, plotting for future jobs, and vacations, I was rarely present.

It eventually caught up with me.

There’s always a reckoning.

At first, after quitting, I did stuff like try to make money and come up with stories that seemed passable for what I was doing and tried to accept that I was an alien in a job-based reality. They were half-hearted attempts that did take some of the sting away of what I was experiencing but for some reason, I knew I had to go through this.

About nine months after quitting, I was starting to feel more comfortable with all the weirdness. That’s when I decided to make what felt like a radical decision. I would no longer do anything to try to make myself feel better. I decided I would focus on doing what feels good right now.

I still had uncertainty and discomfort and no idea how I was going to make money doing what I enjoyed. But I also had a day-to-day feeling of lightness and joy flowing through me. I was having fun writing and hacking on my blog, creating random tools, and launching a podcast.

I decided I would just do that stuff and avoid the sensible stuff.

So I took massive action to lower my cost of living and buy time to figure things out. All of this seemed obvious to me. I got rid of most of my stuff and planned to head to Asia. Other people thought it was bold and crazy but to me, it felt like I was in the flow of something far more powerful.

I wish I had access to ideas like Joe’s at the time. It could have helped me understand what was happening. One of the most interesting things looking back is that about a month after arriving in Taiwan, alcohol evaporated from my life. I lost interest in it and haven’t drunk anything in 5+ years. It was not something I tried to stop, it just happened.

I didn’t think anything of it at the time but looking back alcohol was my prime coping mechanism in my twenties. It was a useful way to feel good and to avoid having to be with myself. I always had plans. It helped distract me from my inner world.

Letting go of my former approach to life and stepping into the messy emotions was pretty intense. There were a lot of feelings and I didn’t know how to handle. Some of the positive emotions like joy and exuberance were just as hard to handle as shame and fear. It was weird to like my work so much. Living in Asia was useful at this time. I was able to retreat a bit from other people, trying to get a handle on everything.

As I emerged out of that (and sort of still am many years later), I started to orient around a few principles:

1. Avoid trading off feeling good in the present for a payoff in the future as much as possible (many mistakes were still made)

2. Focus my energy on what feels good, right now and is something that feels sustainable

3. But also design most initial experiments to quit

4. Create slack in my life for reflection

This is basically what the upcoming book is about.

It’s about how my work scripts short-circuited the possibility of having joy be a primary emotion in my work. It’s about how we have embedded stories about work that hold us back from finding things that help us tap into our raw, inner ambition.

The book will be a deeper personal journey than The Pathless Path. It’s going to explain how sitting in Taipei one morning, I decided that I would attempt to devote the rest of my life to building my life only around work I cared about. And how easy it felt to decide that. I think you’ll like it.

The hardest thing about dancing with these emotions now is learning how to share them with others in a healthy way. For the most part, I try to avoid talking about these things with many people beyond my writing. I’m more comfortable with experiencing uncertainty, fear, and doubt in a detached way. They are always with me and it is okay!

But these emotions trigger the hell out of others. Many people set up their work lives to do what I did, avoid the scary feelings of not knowing what comes next. We run the golden algorithm so that we can feel safe.

I'm shocked at how many things I like and love doing now. It’s quite satisfying. But it has also taken some time and many experiments and mistakes. I honestly don’t know if most people would enjoy this journey or want to go through the inevitable dip of leaning away from our default inclinations. For me, it would have been “easier” if I doubled down on freelance consulting early on and accepted that, “Work is a struggle might as well try to make more than my former job.” I could have kept going in that mode forever. But it would have just been another way to avoid what I really wanted and craved.

Taking a pathless path is a forcing function for facing your emotions.

And it might suck.

But it also might be worth it.

+ Art of Accomplishment has a bunch of courses and is kicking off their Master Class soon. (Not affiliate, I just appreciate their work)

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#2 Some Links

Ice & Bombay: A fun super deep dive on the ice trade in the 1800s and how ice made it’s way from Boston to Bombay.

Post-Work: This was one of the deeper dives I’ve ever read on what it might be like if fewer people need to be employed in the future. It’s written by someone working in AI who cheekily titled the piece “My Last Five Years of Work.” I suspect we will have many jobs for FAR longer than anyone expects or will even be necessary because of how strong the meme of employment is embedded in almost every aspect of our world. I think tech people underestimate how deep it goes mostly because it’s the water they swim in. Despite disagreeing with the premise, I enjoyed the thorough examination of the evidence for or against neutral on the question of whether not having a job is really all that bad:

From the studies on plant closures and pandemic layoffs, it seems that shame plays a role in making people unhappy after unemployment, which implies that they might be happier in full automation-induced unemployment, since it would be near-universal and not signify any personal failing.

No One Wants To Work, Real Edition: Less than 50% of people want to work after the age of 62. Signs of increasing wealth? Lack of interest in modern work? You decide.

Is everyone in Austin Already Retired? A friend, Zac Solomon took a picture of Austin at 2 pm on a weekday that got 25M views. If you want to see the full range of work scripts running in people’s heads, the quote tweets here are great research.

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Hey! Thanks for reading…

I am not sure how you ended up here but might have stumbled upon me through my writing or podcasting on our relationship to work, a topic that has interested me for years.

If you don’t enjoy the writing, I strongly encourage you to unsubscribe below. There’s so much good stuff on the internet!! A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

But if you do want to stick around:

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Home Swapping: We’ll likely be using Kindred a bit this summer. It’s a pretty cool home-swapping alternative to Airbnb. If you want to join, use my signup code.

5.5% Savings: Use this link to get 5.5% on your savings on Wealthfront and increase your runway on your pathless path

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