The Pathless Path with Paul Millerd
The benefits of getting clear on your relationship to work, and how
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Before it was cool, Paul became a “solopreneur” who quit his job, found meaning, and built a life with a radically different relationship to work. He chronicles that journey in his popular book “The Pathless Path” and with his paid community, which I’m a part of. I find Paul’s approach to work surprisingly practical and soulful. Here’s our interview.
Johnny: You encourage folks to get clear on the question: “Why do you work?” When folks get honest with themselves, what are the reasons you most commonly hear?
Paul: The interesting answer here is that there is no common answer. The most common reaction is something like “oh wow, this is actually a pretty deep question. There are a lot of layers here.” The average worker will work 80,000 hours or so in their life and the number of hours people spend thinking about their relationship with work is much less. Some of the surface-level answers people give are money, duty, sacrifice, to do challenging things, to make a living and so on. There is no wrong answer but often work is serving deeper needs that we don’t notice. Our deeper desires like being appreciated, being loved, being respected. These are important to realize too, because they can help you understand when they are missing and also when someone might be trying to take advantage of you.
Johnny: If the answer is “money” or fulfilling the role of a provider, what do you ask that person next?
Paul: I just keep asking, “What else?” I don’t think people realize how much we attach to work. We put moral judgment on work. We can feel that by the guilt or shame we feel when we are without a job or work. People have tremendous anxiety if they aren’t “doing things.” Where does that come from? People rarely think about it. In the US, we are suspicious of people not doing their fair share. We have elaborate government programs to test if people are taking advantage of the system. In other countries, like the UK and places like East Asia, standing out too much is shamed. I found it interesting in Taiwan when a train crashed that the head of the rail system immediately resigned. You’d never see that in the US.
The follow on questions I like to ask after all this digging are “is that enough?” and “Is this the life you actually want?” For many people, it’s not. People say work is for money but deep down they desire a much different setup for their life. It can be hard to realize you are playing the wrong game
Johnny: A lot of folks want to be a solopreneur for the autonomy it gives them. At the same time, a lot of folks find social media soul sucking. Do you see folks carving paths as solopreneurs without social media? If so, what do those look like?
Paul: I left the corporate world because I didn’t want to be soul sucked and am on this new path trying to do the opposite. I use some social media because I find it generative and enjoyable. If you are using something that drains you, that’s incredibly risky. It will undermine your chances of staying in the game, which is the whole game. Since I come from consulting, I know many freelancers build a solid life without social media. You don’t need more than a few clients to make that work. In that setup, social media can be a distraction.
The key here is to be honest about what you want, the kind of work you are willing to do, and what it requires. If you are trying to build an audience, you WILL need to use social media. The key is figuring out:
Pragmatically, which ones are effective in serving me? Twitter used to be a great place for me. Now I don’t find it as generative for my thinking or a good source of ideas.
What can I use such that it makes my life better? I mostly saw social media as a way to build a life. If I was meeting great people in person consistently, that was the only metric I cared about. At certain points, I found that on LinkedIn and Twitter.
Social media “scenes” always change. There have always been places where the nerdy internet types have found each other. It was Quora and then Medium and then even Linkedin and then X and now I see a lot of people in places like Warpcast and Substack Notes.
Generally, question the assumptions. If you are running a script like “I must use social media and it will suck” you are already doomed. Don’t do that to yourself. Start with your own interest and the life you actually want to build and find work and activities that fit into that.
Johnny: For folks thinking about exploring different career choices, you give them a menu of options for taking time to explore (e.g. taking an afternoon off to think about their relationship to work, convert employee work to contractor work to create flexibility, do a sabbatical). Can you walk me through the options you see folks having success with, from least to most intense?
Paul: Sabbaticals appear to be the most potent work-psychotechnology. Consistently people are able to get a broader perspective on their lives, reconnect with themselves, discover lapsed hobbies, and generate new ideas for their life. Some go back to their jobs but many don’t.
Save for a sabbatical like you save for a fancy dream home. It’s worth it.
Almost everyone I talk to wishes they took one earlier.
At the most basic level, the thing I want people to experience is that many of us are going through the motions of our life. A “wander” without a destination for two hours is a great way to notice that your brain is constantly pointing you in specific directions and craves having a plan. What does it feel like to not have a plan? Is it terrifying? If so it might be worth experiencing. Often it’s ALSO exciting and people want to follow it despite it being unsettling.
Johnny: A lot of books espouse ways to test a new startup idea every week. You ask folks to constantly feel into what kind of work they want to be doing. How do you make a practice out of feeling and answering that question? How do folks figure out what “good work” looks like for them?
Paul: Be ruthless about what you don’t want to do. This can be hard because it often means letting go of things that might generate money or other things you should do. For example, the question about solopreneurship and social media. Assuming you MUST do those things is such a bad starting point. I embrace my own framework of “ship, quit, learn”:
Ship something as fast as possible
Design it to quit within the first few weeks or first month
Learn: The only goal is to see what the experience tells you.
Finding writing for me in 2018 was beautiful and devastating. I knew I wouldn’t be able to make money but also knew it was something I loved so much. I had to tinker with a lot of stuff on the side to make money and make sure I found stuff that was “good enough” in that it didn’t drain me but wasn’t too much time such that it took away from writing.
From 2018 to 2021 90% of my “work time” was spent writing and I made about $3k from it. I got by on about $35-45k from various things I did on the side and it was enough.
Johnny: How can folks find you and your stuff?
Paul: My book is at pathlesspath.com
And the newsletter is at newsletter.pathlesspath.com
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