Your Insecurities, Not Mine | #162
November 20th, 2021: Greetings from NYC. I’ve had a whirlwind of a week, wandering around the city meeting many various readers and friends I’ve met online and through this newsletter over the past couple of years. It’s immensely energizing to be meeting people in person again. I will be off next week for Thanksgiving and hopefully will have some good news about a book launch date when I return!
Shoutout to Jeff for inviting me over to cowork, sauna and hang out at this new climbing gym in Brooklyn!
#1 The Only Choice Is To Go and Find Out
A lot of people reach out to me to talk about their relationship to work. It’s been fascinating to see how differently people think about their jobs, work, and how they grapple with the decision making process of doing something like leaving a job.
When you step off the default path, you become a dumping ground for all people’s insecurities about work and life. Sometimes this is simple. Someone might say, “I could never do that.” Others mention their money insecurities, their fear of free time, uselessness, or fear of failure. I always agree with these people becuase I also have some dose of these fears. Yes you are correct, but for me it’s still worth it.
One unique type of inquiry I get is when people start explaining my situation away in a story that makes sense to them. The type of sentence is always the same: “Don’t you think you can do what you are doing because ______________?” This used to make me defensive but now I know that what is happening is people are telling me their own fears.
What people often list are my credentials or past work experiences. While I have some advantages, people give far too much credit to these for enabling my current life and work. Many people still have a mental model of the world that says impressive degree = money and successful career. If I wanted to become a full-time freelance consultant and maximize my income, my past credentials would matter much more.
However, you know I’ve taken a longer, slower, stupider path, working on my mindset, trying and failing many things, grappling with insecurities, and trying many more kinds of work than I would have to if I were merely trying to maximize income.
Why? Simply, I have a ton of fun doing it this way.
This is my actual advantage. My psychological wiring as someone with a relentless need for freedom and autonomy over my work and life, a relative comfort with not fitting in, a willingness to compromise almost all material comforts for more time, and a sense of joy when I’m tinkering with software and computers.
When I talk to other people who are 100% convinced of this kind of life or path or are determined to move in this direction, we don’t spend any time talking about reasons why it is impossible or hard or even about their fears. Instead, we share strategies, we talk about some of the challenging experiences of being on a pathless path in a default path world, and send out subtle invitations for deeper friendship. While the people that tend to talk about their fears or explain away my ability are are almost uniformly well paid professionals, these people, the weirdos, are from all countries, backgrounds, and financial situations.
Many of the people I’ve met that are on the pathless path have done so from an early age. These stories don’t get told as often because they don’t involve a dramatic leap or a major crisis. They have just always been figuring it out as they go.
The deeper you go into a successful career and the more money you make, the harder it is to step away from that path. While this shouldn’t be the case mathmetically, it seems to be one of the most consistent patterns I’ve seen.
A couple months ago someone said to me, “aren’t you afraid of not knowing what to do with your time?” This wasn’t a question about me. I said, “that’s your fear, not mine, right?” He nodded. I explained how I came to figure out how I liked to spend my time and how self-employment forced me into a daily examination about what mattered and learning to deal with financial trade-offs. He bought all of it. He believed me that it wouldn’t be a problem. Yet he still wouldn’t really know unless he faced the situation in reality.
It’s a mistake to look at other people’s paths and then convince yourself that’s exactly what you want or tell yourself a story that you could never do it. There are endless reasons we can deploy to make ourselves feel comfortable.
While stories of others can be good models, we all have different needs, wants, desires, and psychological wiring. Leaving the default paht is really a journey of finding yourself, figuring out who you are and then trying to continue playing the game that makes sense for you. This is quite hard but to many people its worth giving up almost anything to try.
A related short thread I wrote this week on some of the meandering I was involved in over the past few years:
#2 Filtering Information
I had a great conversation with Tom Morgan in New York this week. I reached out to him after listening to his conversation on Jim O’Shaughnessy’s podcast, infinite loops.
I immediately recognize someone else that had gone through burnout and was on the other side of things trying to make sense of his new perspective on the world. I dove into a bit of his writing he’s doing or a financial firm and plan to read a lot more of it. I wanted to share one of his recent newsletters on framing wisdom as our ability to filter information.
The universal principle that comes out of all of this is of the power of your filter. Perhaps the simplest and best definition of wisdom I’ve heard is “knowing what information is important.” This kind of knowing is not solely done in the intellect. Data is constantly being fed into your unconscious, then cross referenced against your experience. The handicappers who have seen thousands of horses have expertise: the ability to filter downwards from 40 variables to the 5 that matter, rather than commit the reverse error of building abstractions upwards to confirmation bias. This is what’s behind the counterintuitive idea of “exformation” from The User Illusion (insights here). The value of information is determined by what’s discarded in the process of creating it. Purely as an illustration, this article represent a distillation of roughly 400 hours of reading and 6 years of thinking. The synthesis of these ideas may merely prove to be confirmation bias, but they are deeply resonant with me. And that’s the crux of the filtering process. That resonance hints at an internal alignment around values. You can intuitively detect it when you read it, when you hear it, and when you speak it. Shepherd wonders if what we hear as “eloquence” is actually people who are letting the words emanate from their whole selves.
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