Q&A Mailbag | #207
December 11th, 2022: Greetings from Austin. Covid kicked my ass this week and nothing was done. I started feeling better today and wanted to get to write and ship some things I’ve had in backlog, namely a few questions people sent me that I said I’d respond to via email. I’m also hoping to ship some half-baked essays I’ve had sitting around all year in the coming week before heading out for the holidays.
I’ll be taking off December 24th and the 31st from the newsletter and am planning on reflecting on this crazy year, writing some recaps, and trying to figure out where to focus for 2022.
+ Ali Abdaal released a conversation with me earlier this week on his Deep Dive Podcast. I always have interesting conversations with him and this was no exception (though I missed Taimur!) - Check out the episode here.
#1 Mailbag Questions
I wondered if you have any tips on how to recreate the social atmosphere when you're not working. Kind of like how when you go to work, you hang out with the same people and make friends there? I'm a bit nervous about missing that piece.
This is a great question and probably one of the things that you should worry about if you plan to leave a traditional job.
When you have a job and colleagues you like, going into an office can be a glorious thing. My first job at McKinsey was like this. I worked in a research office with many driven and curious young people and looked forward to getting into work every day. The inside jokes were epic and nerdy energy was unmatched.
But we get older and that kind of thing can be hard to sustain. The big companies where everyone knows each other’s families and catch up at the grand company picnic just don’t quite exist anymore in today’s workforce. If you are serious about your career you know the truth: you need to move jobs to stay relevant.
But anyone who has shifted jobs or worked remotely for an extended time also knows the harsh reality: most of your work “friends” disappear into your memories as soon as you move on.
When you decide to do something like work for yourself, you start to anticipate and then experience an empty hole in your life, which is also the upside of indie life. You can start from scratch and build up your own world, all around your own preferences. You don’t have to be friends with bob from accounting just because bob from accounting happens to be sitting next to you every day. You can play long-term games with long-term people.
I think this has gotten easier, especially with more people sharing online but when I first left the default path I had the sense that I was a loser. I’ve written a lot about this and I understand it now. Society places a lot of status on people that maintain full-time jobs and is default skeptical of anyone who dares to try another way. We aren’t going to change that but it’s good to be aware of.
This is why at first it’s important to quickly find at least 1-2 online or in-person friends who are not only accepting of your path but enthusiastic supporters. The way I did this was to write and share online. I sucked at this at first. I published two newsletters to less than 100 friends and family in my first six months of working independently.
But in that group, I found out I had a handful of people who believed in me. People that responded to my emails with enthusiastic support. The hard part about this is realizing that most people, even the people that really do care about you will ignore your stuff. This is a normal thing and I think more to do with people’s insecurities about creativity, work, and other issues those people haven’t quite worked through than their actual interest in what you are doing. Most people are lurkers in life.
In that first year, I realized if I wanted to make self-employment work I would need to bootstrap friends and a broader community I would want to be a part of.
This was quite a big shift away from the transactional mindset of the career world where you basically accumulate a lot of favors by being in the right networks that you can potentially cash in sometime in the future but don’t really translate to long-term friendships and relationships.
Here’s a bunch of other stuff I did even before leaving the job that really seemed to help me over the long run.
I wrote online under my name. This one seems obvious but it wasn’t to me at the time. I posted a few articles on LinkedIn and random people in New York reached out to hang out. These led me to meet with groups and other people in New York.
I reached out to a coach on LinkedIn in New York City because it seemed like she had similar interests. I proposed we host a small dinner and I used that as an excuse to invite a few other people who I was interested in meeting. As Nick Gray says, hosting events is the ultimate life hack
I cold-emailed people and told them I liked their work. People really like this and you’d be surprised at how rare super thoughtful emails are.
After quitting my job, I hosted two dinners in Boston around the future of work and then invited people in my coworking space and to a couple of online groups I was in
I opened my calendar for what I called “curiosity conversations” and then invited people I was interested into book calls with me. People were fascinated that I just opened my calendar to strangers. I did this for five years from 2017 to 2022, talking to over 400 people. At first, I’d have very few bookings and by the end, I had a few every week. I’ve become friends with some of these people years after talking in those initial conversations.
I started a podcast and invited people that inspired me. I remember thinking Tom Critchlow was an incredible human and was sort of nervous to talk to him in one of my first podcast episodes. He is of course, but I was putting him on a pedestal. Now I consider him a friend and he’s someone that’s helped me think deeper about my path and I’ve been lucky to get to know him better.
I chose nomad locations based on people rather than career prospects the entire time. I went to Bali because I met Jonny and I thought we might hit it off (I was right). I also went to Mexico during the pandemic to stay with him and ended up attending his wedding on the beach. I stayed in Taiwan because of Angie. I came to Austin because I had met some cool people online here. Making money is important but building lasting relationships is probably more important on this kind of path.
I’ve reached out to people via Twitter to meet in dozens of cities around the world. I’ve met people in Taiwan, Bali, Spain, Portugal, Mexico, New York, Austin, Seattle, San Francisco, Boston, and others. I’ve probably met 100+ people through the internet in person which has led to all sorts of serendipitous opportunities and relationships.
Hosted a pop-up event in Austin earlier this year and invited people on my mailing list and on Twitter. As I’ve built an audience it’s gotten a lot easier to meet people that already have high odds of vibing with me and Angie.
The other thing worth mentioning, which is probably obvious at this point is that I really do like people and love connecting with new people. If you don’t like connecting with new people, especially online, working on your own may be really challenging. You can overcome this but you really do need to build your own mini-bubble of people on unconventional paths who don’t demand you to explain yourself by simply existing. It’s too exhausting and never really ends.
Hi Paul! Curious to hear your thoughts on this if you’re able to provide some perspective. I am on the Pathless Path, and yesterday I received news that my brother-in-law got a promotion. Immediately my jealousy kicked in, so I began to examine some of my thoughts
I guess my question is: How do I not resent him + his promotion? I’m also struggling with how to recognize it, especially since my own views around achievement/status/value/worth are changing
This is a good question and I think I’ve dealt with this too.
For me, it’s very clear that I’ve chosen a path with less guaranteed money in the short term for positive upsides only I see and may never be able to prove, let alone that translate into money. This is a big price to pay and can be painful because you not only know what it feels like to receive praise and affirmation on a traditional path, but you see your peers or family members succeeding and reaping the rewards.
My college and business school classmates are crushing it right now. I see them buying million-dollar homes and sometimes I think, god I should have switched to BigTech, I’m a moron.
But then I remember. I really like this path and there was a real cost I paid to work on nonsense for jerks for far too long.
You are probably sensing that you will never have something like a promotion to prove you are crushing it. This is true. This can feel crappy, especially in a country like the US where the common knowledge is that money = success. It can also feel crappy that you are doing work you feel is more substantial or at minimum less bullshit than your previous job and be a bit upset that you can’t as easily generate traditional rewards yet.
You can never solve these things. Maybe the culture will shift a little. I definitely think it’s headed in this direction. But for now, we live with the remnants of boomer myths of work where promotions, titles, and pay are the ultimate markers of a life well lived.
You’ve chosen your path because you reject that and yours matters to you in some deep way. You need to reflect on those things and remind yourself what they are.
Write them down maybe.
For me it’s pretty simple:
The aliveness I feel being able to have a bit more space and control over my life is substantial
Being able to take a bike ride in the middle of most days of the year without ever telling anyone or ever worrying about a boss is worth $1 million per ride. For the last couple of months, I usually go to the gym and sauna every day around 2:30. I don’t get much done after that anyway.
I work at home every day, rarely have meetings, can work whenever I want, and get to spend a lot of time with my wife who does the same.
The ability to have flexibility in how much I work makes me much more excited about having a daughter. I’ve probably taken off 70-100 days a year for the last several years and I expect to do the same or more in the upcoming year. Knowing I can make it work with this flexibility is really empowering and removes a lot of anxiety about how we will handle the ups and downs of childhood.
Creating your own n=1 path is an exciting adventure in itself and feels much more “real” than anything I ever experienced before 2017.
The right to be wrong. This is underrated. Having your entire reputation at stake gives you a radical sense of ownership and responsibility. This might be freedom?
I’ll always be slightly envious of people who are amassing fortunes in random middle-manager jobs but I’d probably never trade lives with them if you gave me the chance.
#2 On Manners
“A dying culture invariably exhibits personal rudeness. Bad manners. Lack of consideration for others in minor matters. A loss of politeness, of gentle manners, is more significant than is a riot.” ~Robert A. Heinlein
"I never thought I would see the day when having good manners would be an asymmetric opportunity"
I loved this because it’s why I’ve enjoyed writing and sharing online so much. Being nice to other people pays and other people are really nice to me too.
In the northeast where I grew up and worked, cynicism was normal. I didn’t know this wasn’t great for me until I stopped being cynical. With the vulnerability of my new path and many of the health challenges I’ve experienced over the years, I slowly became more patient with others and the world. I didn’t want to dunk on others or make cynical comments about everything. I realized it was a trap driven by insecurity rather than any sort of noble pursuit of truth. We think by being right we will be good but most of the time people just think we are an ass. As I softened into myself a bit I was able to channel a deeper earnestness and optimism that feels more genuine and sustainable.
A lot of people think they need to engage online like they are at war. This is probably because this is still how a lot of people talk to others in the real world. Most people LAPR TV performers. People think any comment is a two-sided debate. These conversations are always silly and never have an end. They are even worse if they involve hyper-aggressive people who get joy out of bullying people into submission.
I didn’t know how much I loved talking about ideas until I found other people online who get exhausted by these bullies too. The magic of conversing online is that you can mute, unfollow, and block the bullies and have a more interesting conversation with hyper-curious weirdos who aren’t on some weird political crusade but really just want to learn.
So next time you want to debate, don’t do it. Just keep asking questions.
More from Jim
Shoutouts (Short notes from Sponsors)
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#3 Paul Lecrone Makes Epic Videos
I love rooting for people and nothing gets me excited like someone who really gives a shit about what they do. Paul cares. And it’s cool. He made my intro for the pathless path video podcast and it’s amazing. Like everything he does.
Befriend him, hire him, retweet him. Here you go:
#4 David Kadavy - Can You Ever Make It?
I wrote about David’s essay “Can You Ever ‘Make It’?” in an earlier issue where he wrote about the challenges and upshot of the solo path:
Take it from me, a ten-year veteran self-employed creator: If you are looking for security or reassurance, I do not recommend this line of work. However, if you are burning with curiosity – if your heart and intuition lead you to do things that don’t make sense – well, then you don’t really have a choice in the matter, do you?
We had a deep conversation about this on my podcast and it was a great conversation. We talked about:
15+ years as a solopreneur (a maven!)
Mini-lives as a way to experiment
How travel is overrated and amazing
Why you can never “make it” but it can get easier
How David found work “being me” for a living
Why he bought a house after being anti-house for so long
Self-publishing and earning more over time (hope to follow his lead!)
Check it out here:
Thanks For Reading!
I am focused on building a life around exploring ideas, connecting and helping people, and writing. If you’d like to support my journey, the best ways are to:
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I can’t wait for you to start writing more about being a dad and the pathless path. I’m supporting a young family with a full-time job but currently experimenting with small bets to one day support us all working on my own. Let’s start a group of chronically uncertain dads on the pathless path 😂.
You and Angie are going to make awesome parents! :')