Embracing Experiments of Living | #284

December 21st, 2024: Greetings from Connecticut, and happy holidays! I’ll be pausing next week’s issue to take some time to write my annual review and likely return on January 11th. Enjoy this picture from a hike we did in Phoenix earlier this week:

⁠As it is useful that while mankind are imperfect there should be different opinions, so is it that there should be different experiments of living; that free scope should be given to varieties of character, short of injury to others; and that the worth of different modes of life should be proved practically, when any one thinks fit to try them⁠⁠. - John Stuart Mill

In my first job, they told us we had two weeks of vacation. I didn’t like this.

I walked over to my boss sometime in September and said, “I’m going to take five unpaid vacation days in December.”

“Uhhh can you do that?”

“I don’t know, but I don’t have any vacation days left and I already booked my flights home for the holiday.”

He laughed a little, shrugged, and said, “Umm, okay. We’ll figure it out, I guess.”

It took me far too long to realize my enjoyment in testing the limits of reality might be better suited for self-employment.

In college, after attending my first Chemistry class, I realized that the professor was reading the text verbatim from the slides. I could download them after class and read them on my own time. While my peers said things like, “I want to go to all my classes so I’m getting my money’s worth,” I asked myself, “What if I didn’t go to any of the classes all semester?” It seemed like a fun experiment. I ended up with a B+. Not bad.

When I decided to apply to graduate school, I knew I would have to take the GMAT test, the SAT for business school. When I started looking into it, I saw that my #1 choice, MIT, accepted the GRE. I had taken that by chance right after grad school and had done pretty well. When people apply to business schools, especially the top schools, they apply to 5-10 of them. Most people see the schools as interchangeable and applying to more lowers the odds of failure. But if I wanted to do this, I’d have to spend months studying for the GMAT. One Saturday, I checked out a GMAT study book from the library and opened it in my fourth-floor Allston, Massachusetts apartment. Looking at the practice test, I thought, “What if I just use the GRE and only apply to one school?” My score was good enough but probably not the best I could do. I ended up getting in.

I’ve always done these kinds of “tests” in my life. I look forward to the “finding out” that results from taking different approaches to things that others around me. The cool thing about being self-employed is not that this is easier (of course it is), it’s that it is a useful orientation toward life, one that helps me avoid getting stuck, keeps me open to opportunities, and helps me enjoy the journey.

Here are some examples of things I’ve tried:

• Types of work: Optimizing for different kinds of work rather than maximizing income, launching all sorts of various “offers”: workshops, virtual cohorts, training, online courses, paid newsletters, and communities (most of which “failed”). I’ve gotten paid for affiliate deals, content, sponsorships, digital products, consulting, advisory, gifts, writing, contract work, being a TA, running on-the-street surveys in NYC, and more.

• Breaks from work: Taking a month off from all work, only working on projects that energize me after nine months of freelancing after quitting my job, taking every seventh week off as a reflect and wander week for two years

• Long creative projects and other non-financial “work”: Spending time on things that may or may not make money: books, online courses, giving talks, helping other people, writing, following my curiosity

• Work Rhythms: Working at different times during the day, shifting work approaches monthly, seasonally, and yearly. Not having a structured workweek (six years). Embracing a structured workweek (1 year). Working on the weekends and exploring during the week. Working in a co-working space. Working at home. Working at home with a baby. Working 2-3 day weeks after having a child.

• Location: Living abroad with a long-term lease. Living nomadically. Living in three different countries for a month in between leases. Moving and selling all my stuff multiple times.

I had someone asking about “reinvention” this week after they finished The Pathless Path. They wanted to know “how” to do it.

My response was a shorter riff on the above. I said that reinvention is, “a slow process, but ultimately involves doing things differently than you have been doing.”

I thought it might be worth expanding on this.

Reinvention is an interesting thing. It is something people talk about like a discrete event but I’m not sure you can pin down any sort of start or end to a “reinvention.” Nor even be conscious that one is underway.

Whether we want it to be or not, most of life is an ongoing reinvention. Sometimes slower, and sometimes faster.

The key thing that makes it hard and challenging and something people talk about is the second part from above: you start doing things differently.

You start behaving differently from the people around you. You’ve always done things a certain way but now, you don’t quite do it that way. Others notice. Or at minimum, you are aware that others could notice and that you suspect some of them are not saying anything about it. You may feel tension in some of those relationships. On top of that, you’re confused. Who the hell are you? You are acting in ways that aren’t congruent with a narrative you had about yourself. You feel unmoored. As you try new things, you make new tradeoffs, where the costs are clear but the benefits are less clear. Something is underway. You might want to stop it but it doesn’t seem like there’s a choice anymore.

If you deny natural change long enough, you will eventually be thrown head-first into this process, which may not always end well.

I like my current path because it’s forced me to exist with all of this almost all the time. On my previous path, I was blissfully ignorant, which was nice, until it wasn’t.

My current path nudges me to be aware that change is happening and to lean into it. It’s not always fun but it does seem to give me some general feeling of active engagement and responsibility for my life, which is far better than the disaffected passivity on my previous path.

My biggest takeaway? It’s not that scary and I’m so grateful for everything I’ve learned. I think more people should be leaning into the natural change underway in the universe (and their lives) and be running their own experiments. It could be as simple as taking a different route to work for a week or as complex as living abroad for a year.

The more things I’ve tried, the more I realized I wasted a lot of time in my twenties doing the same thing each week. I mistook changing jobs as a way of shaking things up, when in reality all I was doing was changing my title on LinkedIn. It’s one of the few regrets I have: I should have run more experiments.

What I’m really saying: try stuff.

This sort of approach works for many things. My friend Calvin Ross gave similar advice to someone who told him they wanted to quit their jobs but didn’t know “what they wanted”:

So if you’re serious about figuring out what you want, don’t try to think your way to an answer. Stay curious and try more stuff. Trust that your meandering will help you learn about yourself and eventually guide you to a more enjoyable path.

I love that last line.

Trust that your meandering will help you.

When. I look around I see too many people with zero meandering in their lives. Zero experiments.

What if you bumped that up to 5%?

What might you learn?

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I want to leave you with this passage from John Stuart Mill from his book On Liberty who wrote quite eloquently about the value in finding out how to live in 1856:

Nobody denies that people should be so taught and trained in youth, as to know and benefit by the ascertained results of human experience.⁠⁠ ⁠⁠But it is the privilege and proper condition of a human being, arrived at the maturity of his faculties, to use and interpret experience in his own way.

It is for him to find out what part of recorded experience is properly applicable to his own circumstances and character. The traditions and customs of other people are, to a certain extent, evidence of what their experience has taught them; presumptive evidence, and as such, have a claim to his deference: but, in the first place, their experience may be too narrow; or they may not have interpreted it rightly.

Secondly, their interpretation of experience may be correct, but unsuitable to him. Customs are made for customary circumstances, and customary characters; and his circumstances or his character may be uncustomary.

Thirdly, though the customs be both good as customs, and suitable to him, yet to conform to custom, merely as custom, does not educate or develop in him any of the qualities which are the distinctive endowment of a human being.⁠⁠

T⁠⁠he human faculties of perception, judgment, discriminative feeling, mental activity, and even moral preference, are exercised only in making a choice. He who does anything because it is the custom, makes no choice. He gains no practice either in discerning or in desiring what is best. The mental and moral, like the muscular powers, are improved only by being used.⁠⁠

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🎄 Merry Christmas

I’ve been having fun and hanging out online since 2015. I’ve somehow figured out how to hack a living doing things like this for more than seven years and taking off a lot of time around the holidays without having to pull unpaid leave shenanigans anymore.

If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work. If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community.

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