Paycheck Envy, The Creator Game, Leaning Out | #231

July 15th, 2023: We just completed our two-week trip to the northeast, our first with our daughter. It went smoother than expected and I’m a little less nervous to travel now. We are spending a final week in Austin before heading back to the northeast for the summer. Our tentative plan is to come back to Austin at the end of fall but we have been feeling adventurous, so who knows!?

The Squad

NYC Meetup July 25th: I’m co-hosting a meetup with Khe Hy in ten days in NYC. Come by, I’d love to meet some of you. RSVP here please.

Virtual Sabbatical Event July 27th: Join Michelle Varghoose, Paul Millerd, Tobi Ogunnaike, Cécile M, and Matt Yao in a curiosity-driven conversation discussing all things sabbatical-related! RSVP here.

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#1 Paycheck Envy

The worst fate in the modern world is to go a month without an income. People do all sorts of things to avoid having to go without an income and do all sorts of things to recreate an income when they don’t have one.

I’ve started noticing that people feel more comfortable with steady flows of money coming into them rather than having a higher amount of money sitting in a bank account or having it be the result of a single financial event.

Consider the following popular business goals:

• Obsession with “MRR” (or monthly recurring revenue) in software products

• Boring businesses with monthly “cash-flowing” assets

• Real estate that produces cash flow from rental payments

• Passive income from digital products

We might call this paycheck envy, the tendency to glorify opportunities that produce steady cash flow over opportunities with higher economic payoffs.

I’m not immune either. I’ve written about how creating a diverse range of income streams (despite some being quite small) has been an explicit goal. But am I deluding myself? Am I wasting time chasing a monthly recurring $100 when I could just try to spend more time thinking through what it make take to sell a $25,000 workshop to a company doing work I enjoy? I’d only have to do that once every 20 years to equal the impact of a recurring $100 revenue stream.

What I think is going on is that people are seeking permission in the form of money to live their lives. I sense that the default path way of working, mostly in the form of salaried employment, has shaped the reality of most adults so fully that we see any sort of existence outside of this as suspect.

If this is true, we are placing money first and foremost above the practice and art of living life. We see some evidence of this from the reluctance of people with more than enough money to stop or work less before they hit the formal retirement age. We also see in many retirees who have saved a lot, the shocking data that most spend down very little of what they saved for retirement. Just like we have sunk costs, it seems we have sunk incomes. They are earned in the past and therefore can’t serve our needs in the present.

Personally, I struggled with this a lot in my first two years of self-employment. I operated my life as a CFO, ensuring that expenses were below income. But looking back this was irrational. Not because there was any economic opportunity at stake but the fact that I realized quite soon after quitting my job that I was super excited to be on a new path and wanted to stay on it!

I was putting all my psychological effort into leveling up my inner game but I was scared as hell to spend a dollar on myself if I hadn’t earned. I was stuck in paycheck envy hell.

One thing helped me reframe this. Someone (I really forget who, so if it is you, let me know) told me, “Consider your savings a gift from your former self.” It was a powerful shift in my thinking and helped me become a little less attached to my own money stories. Try a thought experiment. Instead of your current job or working situation, imagine you spend five years working in a different country, company, or industry. It quickly becomes obvious that the amount of money you’d have now would definitely be different. Run this thought experiment 100 different times and you start to feel that the amount you have was not in fact destined by God but more random than you might have liked to admit before this paragraph.

And this is the hard thing about money in general in today’s world. Everything does feel a bit random. It seems like every millennial knows someone who accidentally got rich by joining the right startup at the right time, realizing enterprise sales can be wildly lucrative, or being born with the psychological makeup that makes working in finance or law less painful.

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#2 Games

My rough idea for a second book is something tentatively titled “The Creator Game.” It’s still in the early stages but I’m starting to sense a very vague feeling in the distance that I’m starting to see a bit better. I’ve been going down the rabbit hole of games as a whole research area and it’s pretty interesting. I recently listened to a podcast with this podcast with C. Thi Nguyen on Ezra Kleins Podcast which led me to his book, Games: Agency as Art (that’s the book link but you can read his papers, which are very similar, for free here)

I love the idea of a game as a way of practicing agency and it gets to the heart of what I was thinking about with my tentative title. Here are some quotes that stood out:

In ordinary practical life, we usually take the means for the sake of the ends. But in games, we can take up an end for the sake of the means. Playing games can be a motivational inversion of ordinary life.

And when we play games, we take on an alternate form of agency. We take on new goals and accept different sets of abilities. We give ourselves over to different—and focused—ways of inhabiting our own agency.

We can change our in-game ends easily and fluidly. We can adopt new ends, which will guide our actions for the duration of the game, and then drop them in an instant. When we play games, we take on temporary agencies—temporary sets of abilities and constraints, along with temporary ends. We have a significant capacity for agential fluidity, and games make full use of that capacity.

In some sense, the motivational world described by traditional economics—one in which identically motivated rational actors compete with one another—is false in the actual world, but true in game worlds. When games work, they can sometimes present us with the world as we wish it could

I sense work, especially paths like mine are all about embracing a game stance toward the world. How do take agentic actions with different kinds of work, at different times, in different phases of your journey? This is incredibly hard, of course, as the biggest challenge is the presence of infinite options.

Excited to dig in more with this and see where it takes me.

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#3 Post-Sandberg - Is It Time To Lean Out?

Had a wonderful conversation with Dr. Dawn Baker about crafting an unconventional life despite going to medical school. We talked about:

1. Dealing With a Brain Tumor: Dawn shares her health crisis, where she was diagnosed with a brain tumor. This event served as a wake-up call and led her to reevaluate her life and career.

2. Leaning Out: Dawn discusses her decision to "lean out" of her career in medicine and how she and her husband intentionally designed their lives to prioritize their personal needs and desires over traditional career expectations.

3. Financial Independence: Dawn and her husband followed the financial independence movement, which allowed them to reassess their career paths. They realized they were financially independent around the time their baby was born, which opened up new possibilities for their careers.

4. Homeschooling & Living Off Grid: Dawn shares her experience with homeschooling her daughter, which she views as an unconventional path that aligns with her philosophy of “leaning out.”

Also here are some quotes that stood out from the conversation:

• Infertility and Career: 29:02 - "I feel like it's too late if you say well the critical time is when you're building a family is to lean in because of the typical age that you are and like the type of career path that you're on at that time that's the assumption she's making there but she is absolutely not addressing the fact that 13 percent of couples in this country are infertile and worldwide infertility is going up in professions like medicine and probably law…it's at least double that."

• Men Leaning Out (Timestamp: 37:02, Link): "I get men coming up to me and they say exactly what you're saying where they're like well you know I don't want to do the traditional thing either but it's less acceptable in certain circles for men to be like well I don't want to achieve and I don't want to make the most money and be the breadwinner."

• Financial Independence (Timestamp: 40:02, Link): "We started figuring out that we were actually financially independent and that opened up the realm of for me especially what I could do with my medical career."

• Homeschooling (Timestamp: 43:02, Link): "When my husband first said to me that he wanted to homeschool I thought he was crazy because I really didn't know anything about modern homeschooling."

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