The Chapterization of Life

What do you consider to be the happiest time in your life?

The definitely-not-widely-accepted U-shaped happiness curve suggests that we are the happiest in our youth, and then again in our retirement years.

The question of happiness is depressing to consistently dwell on, but my time of peak happiness was probably either the senior year of university or the senior year of high school, which is interesting to me because they are fundamentally different stages of life with very different quests, concerns, and characters.

In university, I had an active social calendar, ran a student club that I was fully engrossed in, and I was generally experiencing my first taste of independence. In high school, I had a very fun group of lovable homies, I lived with my parents, and altogether I had a pretty narrowly defined world. These two very different times in my life had completely different circumstances, but when I reflect on these times, I really appreciate the diversity of experiences I had. Conquering different problems in different arenas is exciting.

One of the principles of modern happiness theory, which I agree with and find intuitive, is that novelty and new experiences tend to bring happiness.

Stumbling on Happiness describes this concept as habituation – wonderful things are especially wonderful the first time they happen, but their wonder wanes with repetition. The book mentions how separating events with time and introducing variety can reduce the diminishing characteristics of utility. In our everyday lives, I suppose this is like comparing the first vs. tenth helping of turkey, the first vs. tenth week of summer break, or perhaps the first vs… fifth… drink of the night?

Managing the frequency of events and spacing them out is a good way to manage your reward system and keep things feeling interesting. Consuming or experiencing something in rapid succession can make it lose its luster extremely quickly.

Novelty and diverse, new experiences also impact our perception of time. Months and years can feel like they’re flying by if you’ve been going through a familiar and habitual routine.

I do not think it is a good thing to be able to look back on your last few years and perceive the past to be blurry.

The foreshortening of the years as we grow older is due to the monotony of memory’s content… Apprehension is vivid, retentiveness strong, and our recollections of that time, like those of a time spent in rapid and interesting travel, are of something intricate, multitudinous and long-drawn-out.

William James, 19th century psychologist and philosopher

Philosopher William James suggests that time tends to pass by quicker if you live a monotonous life.

I think there are implications here for life planning. If we can contend that living life is inherently “good” and submit to the limitations of mortality, then perhaps one way to live a long life is to distort our perception of time. We can do this by introducing variety, treading past our comfort zones, and embracing the unknown.

There is a scene in Billions, which I know is highly stereotypical for me to like, where Taylor Mason (pre-character assassination) is deciding whether to go to a family event or an extravagant holiday work party. Chaotic neutral protagonist Bobby Axelrod offers up the use of his helicopter to overcome the problem, as well as his advice: “You only get one life, so do it all.”

A Life of Many Chapters

Reflecting on the diversity of my high school and college experiences, as well as my past few years in New York has made me think about the “chapterization” of life. It has also taught me about the power of anticipation – why looking forward to the next chapter can feel so exciting.

After a relatively monotonous chapter of life (the weekends in New York were great, but the weekdays were incredibly the same), I now want to seek out new, novel experiences. After delaying gratification for so long, I’ve come to believe that extreme delay puts too much confidence in the unknown. We don’t know if our health will hold up or what we will be like in the future; it’s hard enough knowing what we are like in the present.

It is my perspective that planning a life with distinct, different chapters is one way to create novelty and do more of it all. When I think about the vastness of the earth and the number of different permutations of life there have been, are, and will be, I get a little anxious thinking about how narrow my life perspective has been. If atheists and Drake are correct in that humans only have a singular mortality, then I think it would be a shame if I only got to experience the life that was most conveniently set up for me.

Life is naturally set up in stages (commonly… childhood, education, work, retirement), but the elongated chunk of work doesn’t appear to allow for a lot of diversity or change. It may be true that the most Americans have 11.7 jobs before turning 48, but only ~30% of Americans have lived in three or more states in their life, and only 43% have ever lived outside of their current state, which suggests to me that people are naturally disposed to relatively static lives.

Here are the life stages and chapters I would like to try before I die:

• Sabbatical
• Living abroad with my significant other
• Digital nomad (working remotely while traveling)
• Extended travel by myself
• Extended travel with a group of friends
• Raising kids (including sub-stages of raising infants; toddlers; teenagers)
• Work
• Retirement

In list form, this actually isn’t too different from a normally constructed life, which is pretty comforting.

I think where this potentially becomes more interesting is in planning to have multiple careers (which is different from just having multiple jobs). As part of my obsession with becoming a polymath and novelty, there are a number of career paths and ideas I want to pursue before I die:

• “Solo” entrepreneurship
  • It’s one of my main hypotheses that I am able to work my hardest when my incentives are fully aligned and I am the primary stakeholder. Digital content and direct-to-consumer e-commerce are the two paths that seem scalable, don’t require raising outside capital to get started, and don’t require deep technical expertise (these low barriers being both good and bad).

• Educator
  • I really enjoy teaching and giving the gift of knowledge – I’ve written guides my entire life and I enjoy packaging information in concise and helpful ways. I’ve always thought teaching to be a fun vehicle to exercise “intellectual empathy”, while helping you cement your understanding of something. I can see myself pursuing the gamut of teaching channels: YouTube videos, digital content course, or being a professor / lecturer later in life.

• Musician
  • Ever since I was 25, I had the dream of becoming a modestly successful musician. This is a super interesting side-quest in my life and producing music (mostly electronic, house, bedroom pop) has occupied a significant amount of mind-share since I started doing it. I think I prefer music just as a dimension of my life, as opposed to my sole source of passion (like Ron Swanson / Duke Silver), but we’ll see, because it is incredibly consuming. Creating art is one of the most fun activities I’ve done and I totally understand why so many people devote their lives to it.

• Author / Writer
  • Writing is perhaps the first interest I truly cultivated growing up. I think this is because I only knew English as a kid, so I wanted to make damn sure I was good at it. I would love to further explore this later in life and can see myself becoming a columnist, taking this blog more seriously, doing comedy writing, or putting together a fiction novel.

• A less stressful finance / capital allocation role
  • As a recovering finance dude, it’s hard to hypothesize when I’ll actually enjoy the idea of working in finance again, but I do fundamentally think investing is interesting. You’re making bets about the future and trying to understand business. I can see myself participating in a lower-stress family office type role or low-stake venture capital role – I mean, ideally, I’d just be managing my own money.

• Non-profit / Philanthropy
  • One thing I really miss from being in school was the extra-curriculars. When the time is right, I’d love to get involved with a cause or initiative that I’m aligned with and develop a sense of community around.

We may not actually be able to have it all, but I’ll give it a shot for my life and let you know how it goes.