Intro

Hi friends — this letter was supposed to focus on self-definition, both internal and external, and motivation. However, that became very long with many rabbit-holes, so I decided to focus this one on just one of the rabbit-holes: self confidence and lifestyle creep, particularly as it related to material possessions.

Now four newsletters in, there are over 75 people—more than 15 of whom I’ve never met in person, and some of whom I’ve never corresponded with— subscribed. If you’re one of the people I’ve never met, please feel free to reach out!

Readings

The Self Confidence of 4th Grade Girls

A few weeks ago, Jessica Mauser, a corporate real estate managing partner and broker from the Bay Area, chaperoned her daughter’s 4th grade class field trip, a 2-night camping excursion. Because of COVID and parents holding their children back for various other reasons, the ages of these girls ranged from 9 to 11. Wrote Mauser, “Some girls still secretly think unicorns “slay” and other girls who brought an entire Sephora store worth of skin care [sic].“

Mauser tweeted numerous notes from the three days she spent as a fly on the wall for the 18 girls in her tent. One theme in particular stood out to me: The lack of self-definition each girl had, and how it affected behavior in a group setting. Mauser described girls who, in a group, would not stand up for themselves or each other. Girls who allowed incredibly harsh words to be said, until someone cried. Then, the whole group would be sympathetic and supportive:

Mauser went on to posit that instilling a “quiet confidence” in children is a potential antidote to this lack of accountability. When a reply asked Mauser to expand her thoughts, she replied:

These tweets had me reflecting on my own sense of self, what I take pride in because it looks good to the groups I hold dear versus what I take pride in because it makes me, and only me, proud. To be clear, I think neither of these forms of pride is bad in a vacuum. I’m quite proud of the groups of people and causes I associate myself with, and my friends’ values are ones I admire. The trial by jury often leads to positive results, and I think there’s a natural tendency to default to it. There’s a reason people say you’re the average of the 5-10 people you spend the most time around. And that’s a great reason to be deliberate about the people we spend our time with. However, I’m starting to realize that this “values by group” approach, even when “optimized,” can be a trap, for reasons I’ll detail below.  

My home base is now Charleston, South Carolina. I work for an investment firm with no outside investors. Half of the partners at our firm don’t have any sort of online profile, including LinkedIn. At a local networking event, a Yale grad who moved here a few years ago told me to never ask someone, “What do you do for work?” (which I’ve written about previously) because it will mark me as an outsider. That’s in sharp contrast to places like San Francisco, New York, or Boston, where most of my friends are living. To make a long story short, almost nothing I do personally or professionally needs to be performative. This can be a huge blessing or a huge curse, depending on how I use it. More below.

Money as a Default Motivation

I am not particularly motivated by money, consciously. I think this stems from the fact that I don’t think I deserve particularly nice things. It also helps that the hobbies and items that make me happy are not expensive. I like going to the movies, eating sweets, and reading good books and articles. Most of these can be done for low costs ($20/month unlimited movie passes, candy bought in bulk or eaten at the office, PDFs). I’ve never really cared about cars, clothes, or clubbing.

Recently, though, I’ve been pegging progress to the dollars stashed into my retirement accounts, the points in my credit card and hotel rewards programs, and the pieces of furniture in my apartment. (I just bought a side table for my couch!) Reading the above tweet made me realize I’ve been dopamine hacked to feel accomplishment from the possession of countable objects. This, in and of itself, isn’t a bad thing. I actually think it’s quite healthy to start taking pride in my retirement savings, for example. However, it’s gotten me thinking about the less objectively-good, money-focused or money-adjacent metrics of success and how they creep into our lives.

In a lot of ways, my professional development has been an iterative process through which I realize a nice thing, while unnecessary, is a huge unlock. This process began right before I left for college, when my mom dragged me to Macy’s and bought me two suits. “You’re going to Harvard, you’ll need these,” she said. I was confused, since those two suits were worth more than the entire rest of my wardrobe combined. “You’ll get it once you’re there,” she said. She was right.

This adoption of socially-acceptable habits continued as I got older. It led me to buy my first pair of shiny dress shoes, my first table at a night club, and my first tuxedo. While each of these purchases hurt when I made them, they were all worth it. If I could go back in time, I’d buy them all again in a heartbeat. (Well, maybe not the night club table.) Some items — like the tux — were preemptive, items I bought because I anticipated the lack of it being an impediment. Others were reactive. For example, I bought the shiny shoes after I noticed a well-connected alum in his 60’s overtly stare at my leather sneakers. I could flash the same educational credentials, exercise the same manners, and leverage many of the same connections that he could, but my lack of $200 shoes impeded my ability to connect with him. While style and polish of footwear is a stupid reason to judge a person, and one that our generation rarely cares about, I realized it is a gatekeeping item nonetheless. I vowed to never let an old man use my shoes to judge me again.

This example seems silly, at first. What does the taste of a man near retirement reveal about lifestyle creep in mid-20’s young adults? I think it reveals the psychology of lifestyle creep: People use material items as proxies for certain qualities (fitting in, having one’s life together, personality). We all experience being judge based on material items (or lack thereof). Then, we start anticipating all possible ways our material possessions can be judged. For example, I think most well-dressed guys our age can tell a similar story about a girlfriend or crush who mocked their hoodie/t-shirt/raggedy shoes. Enter: button-up short-sleeve shirts, all-white leather sneakers, and chino pants.

It took me awhile to articulate why this tweet bothered me so much. It finally hit me this weekend: I wasn't raised to consume very many expensive things, so every expensive habit is one I consciously adopt. And adopting expensive habits feels wrong. But, as described above, some expensive things are worth paying for. To help navigate these conflicting emotions, I now classify material possessions into three categories: Inherently valuable, contextually valuable, and narrowly valuable.

• Inherently Valuable: Something that is self-evidently worth buying, even if no one else sees or uses it. Most often, personally, this means something that improves my long-term health.

  • Primary example: I bought my first $200 pair of sneakers, New Balance Fresh Foam 1080s. These are much more comfortable and supportive than my previous, 3-years-old sneakers, and my foot and knee pain disappeared within a week of wearing them.

  • Other examples: retirement account savings, a good mattress, good food, exercise class or gym membership.

• Contextually valuable: Something that, while not used daily, is worth buying because it “pays for itself.” This could be socially, economically, or from personal enjoyment.

  • Examples: very nice clothes (particularly ones worn only on occasion), membership to a social club, going out for drinks with coworkers.

• Narrowly valuable: Something that would classify as a “want” more than a “need” in Junior Achievement terms. The non-economic value ascribed is highly personal and zero for many.

  • Examples: nice car, going to a sports game, jewelry.

This is clearly not a perfect system. Some categories overlap; some categorizations are hugely dependent on factors like job, location, and social circle; others are totally up to personal preference, etc. And sometimes a contextually valuable buy turns into an inherently valuable one. For example, owning some nice clothes has made me start to appreciate the nuances of fashion more, and I get greater enjoyment from putting together a good outfit. However imperfect this system is, though, I’ve found it very useful as I consider what to spend my monthly paycheck on.

I originally wanted to make this a meditation on money and why we prioritize it, but this is pretty long already, so I’ll call it here. (Spoiler: As you get older, it’s the easiest way to compare yourself to everyone else.)

Conclusion

As mentioned previously, I’m largely geographically and professionally removed from the games a lot of my peers are playing. I’m working in a place with no bureaucracy that, I think, can help my achieve my professional ambitions if I earn them. I’m not judged for the shoes I wear, how expensive my haircut is, or the car I drive. I don’t have to dress like a New Yorker or do performative tasks to be noticed by my boss because we sit next to each other every day. Right now, I have the blessing of self-definition usually afforded to people much farther along in their careers. I’m determined to make the most of this privilege. That said, I’ll probably end up in a more superficial physical location if our firm does as well as we hope.

I have a feeling I will return to these themes — what makes me happy vs. what makes others happy, and to how balance each — more frequently as I get older and have more responsibilities. I speed-ran through my psychology towards nice things and how it developed in undergrad, which could be an entire essay unto itself. I’ve also been thinking a lot about how things like family, romance, and physical location affect everyone differently. I’ll save that for later.

My Best,

Sam

PS: I’m planning to be in NYC, San Jose/SF, and Boston quite a bit over the summer, for both work and fun. If you’re in any of those cities, please reach out. I’d love to catch up and meet for coffee/drinks/dinner.