Money, Guilt, Shame & What Matters | #140

🤔 Pondering the questions on work, life & what matters

May 7th, 2021: Greetings from Taipei! Boundless hit 4,000 subscribers this week. I am humbled by how many people have decided to follow along with my writing, creating, and vagabonding journey as I navigate life off the default path. I remember sending out an early newsletter to about 100 people and being terrified. What if someone dislikes what I write?

What I’ve found instead is a small but growing group of deeply curious humans from around the world who are thinking about many of the questions I explore in this newsletter. I appreciate you.

👉 I am considering a number of experiments for the rest of 2021, including bringing on someone part-time to help me with a number of projects. If you are interesting in helping with editing the book I’m writing, or helping out with marketing for my consulting skills business, or editing videos, please reach out!

💻 What happens when you take a year off from medicine and your YouTube channel gets > 1.5 Million subscribers? Do you leave medicine? What is your identity? What does your mom think? Check out my interview with Ali Abdaal where we dive into all these questions. (Podcast | YouTube)

🙏 A special shoutout to Tyler and Rowan who became paid supporters this week. If you’d like to join them you can do so here or you can just share the newsletter with a couple of your friends

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#1 Invisible Shame Monster

One thing I absorbed from the culture I grew up in was that someone who didn’t make a lot of money or that spent their time at something deemed a “low-skill” job was of questionable character. There were always carve outs for people you might become acquainted with, but generally people that had more money were better people.

If you only could understand one thing about American culture it’s that money is the most important thing. We say all sorts of other things about what matters but when it comes down to it the fastest way to get respect and admiration is to be rich. Our reaction to an infectious disease was to deliver four rounds of financial stimulus to the economy. Our biggest celebrities are now billionaires getting divorces rather than movie stars getting divorces.

People have a lot of feelings about money and I’ve written about how money is often just a placeholder for deeper anxieties about life. It seems people will amass millions of dollars before they try to stare the feelings that make them stressed in the face. Many people seem to get the money but never satisfy the worry. A successful real estate investor still worries about being poor1:

“If somebody tries to screw me over, I think back to all the people who screwed my father out of money, and I react very viscerally to it because I am afraid of being poor still.”

When I started talking to people about their relationships to work I was surprised to find many of these emotions. One person had hundreds of thousands of dollars in savings but when I suggested he consider a break to get a handle on his work-related depression it was as if I suggested he cut off both of his arms.

If you ever had doubt about human motivation, watch someone lose their job. Someone without any interest in changing their work circumstances will be be filled with the energy needed to build the pyramids. One of the saddest things for me was when I started coaching people. I saw this motivation drop from 100 to 0 as soon as the person secured employment. If we could harness this energy we could solve most of our biggest problems in a couple weeks.

Both of these people are acting reasonable given our culture. To be unemployed or without work is to be looked upon with suspicion. Something must be wrong with them, right?

The hidden force of work: shame

One thing that surprised me when I shifted away from a work formula that optimized for income growth was how shameful I felt. The voice in my head said, “you are a bad person.” I know this is crazy to feel but this also means many of those people terrified of taking time off from their job were judging the risks accurately.

Shame impacts everyone’s relationship to work. When we are successful on paper, fear of shame keeps us locked in our jobs and when people are not succeeding they feel like something is wrong with them. Here are selected quotes UK citizens fighting poverty:

“I’m ashamed I can’t provide for my children.”

“I don’t like people seeing me go to the food bank.”

“I feel I’m doing something wrong.”

“I find myself apologizing all the time.”

“Falling into debt is like drowning.”

“I’m humiliated waiting for items that have reached their sell-by date.”

Yet instead of staring these emotions in the face we march along in cargo cult lockstep talking about job creation, retraining people, giving people monetary incentives to “pull themselves” out of poverty and so on. What if we took a minute to talk about how terrible everyone seems to feel?

I wanted to be rich

When younger, I remember answering the question “what do you want to be when you grow up?” with one word. Rich, I wanted to be rich. I don’t know how I came up with that but I remember adults being impressed.

If I could talk to my former self I might ask, “and then what?”

I once talked to a college student that told me he was leaning towards working in finance rather than applying to a PhD program because the salaries in finance were higher. He reasoned that this was what society valued more and that it was smart to do what society valued most.

Why do we accept this kind of formula so quickly?

One of the things that I’ve realize from living abroad is that our economic systems shape a lot of our work beliefs. If the economy is booming (like it was for the boomers during the “great boom”) it would make a lot of sense to believe in a script that says work hard and you’ll be set. If your economy delivered stagnant wages, like in Taiwan and other countries stuck in the middle-income trap, you’d come to believe that more government support might make sense and that not spending beyond your means it the only way to live. If your economy shifting to only working for knowledge workers or those with investments, you might come to believe that hanging out online, shitposting, and investing in meme stocks is a better use of your time than getting a job.

Obsession with money isn’t all bad. I tend to agree with the Tyler Cowen view of progress that more economic growth is better for the world and this probably requires hacking some of our normal human motivations of greed, status, guilt and competition. However, we forget that traditionally work was about taking care of our family and community and replace it with a game of “he or she that dies with the most stuff wins” as Jim Rutt likes to say. We split the world into a fake high-skills vs. low skill2 dichotomy and look upon anyone who is struggling or steps away from the steady ratchet of more is more with suspicion.

This hardly seems worth the costs

Guilt vs. Shame

I think Brene Brown’s definitions of shame and guilt can be helpful here in helping us to make sense of this,3 First is shame:

Shame: The intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging – something we’ve experienced, done, or failed to do makes us unworthy of connection.

Brown doesn’t think shame is helpful. She thinks it “is much more likely to be the source of destructive, hurtful behavior than the solution or cure. I think the fear of disconnection can make us dangerous.”

In other words, we can’t really solve shame. Compare that with guilt.

Guilt: Holding something we’ve done or failed to do up against our values and feeling psychological discomfort.

Guilt is actionable and this is why most people work - they want to create, think and help others.

I went into one of those paths where money is bountiful as long as you stay on the path. The issue is that a lot of the work feels utterly pointless. One study found looked at unemployed or inactive people and found that after eight hours of work and up to 16 hours or work there were substantial benefits to personal well-being. The crazy thing is that many people work 50+ hours in jobs like consulting and never reach that feeling like they are doing enough or anything worthwhile. The late David Graeber called these “bullshit jobs.”

I had guilt but no amount of hours making slides seemed to satiate it. My definition of value was different than creating PowerPoint slides for men in suits. I felt guilty because I felt like I was bullshitting myself, not doing anything I claimed to value. Yet what held me back? Shame. Our wage based reality is filled with invisible shame particles that are always there and you can sense that if you step off the default path you might not be love. You might not belong.

I’ve talked to people whose families stopped talking to them because they switched to the “wrong” path. For most people it’s usually more subtle. You don’t get disapproval from friends and loved ones, but constant interrogation. Why do you have to be this way? Why can’t you be like everyone else?

One of the most amazing things that happened when I started writing online was that people started reaching out and telling me that my words had a profound impact on their life. I probably get about one or two of these notes per week now. It’s the biggest driver for me to keep going. This past week one person told me my writing made him feel like he had a friend as he was about to leave his job. Another person messaged me to say that my podcast has given her and her husband comfort while dealing with his unemployment.

I don’t feel guilty anymore because I feel like I am following through on what I claim to care about. Shame however? I still don’t feel perfect. I’ve learned to ignore it but it’s still very obvious that leaning against money and acquiring stuff still makes other people uncomfortable.

Who has the wheel?

Shame is at the steering wheel of our work lives.

We stay in bullshit jobs for years because we know one person saying you are “useless” will crush you. People struggle to find work they would be good at because they are too busy punishing themselves for not being good enough. To top it off we become so resentful of feeling this way we judge others who are either struggling or taking a different way.

This is a huge tragedy of the commons.

Take back the wheel. At the individual level the most interesting things seem to happen for people when they shift away from the more = better script and lean into the values that actually care about even a little. Lean into your guilt that you aren’t doing what you care about and ride that through the inevitable shame of trying something new.

I still battle feelings of stupidity for leaving the path that makes sensebut it has so far been worth it. I continue to write because of how many people seem to struggle with these same feelings in all kinds of places and types of work around the world.

I’m here for you all. You’ll always belong here.

And to my younger self": “hey buddy we didn’t end up rich but we ended up with something a lot better. Just be patient and follow your curiosity. You might be surprised at where it takes you.”

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#2 Ali Abdaal On Balancing The Identity of a Youtuber & Doctor

I interviewed Ali Abdaal this week who I’ve been lucky to get to know over the past year. He’s got an incredibly successful YouTube channel with more than 1.6 million subscribers that has more or less solved his “money problem.”

Last year he took a year off from medicine and leaned into the creator economy and doubled down on his online business. We didn’t dig into how we did it (there are plenty of other interviews where he goes into that) but some of the deeper questions like:

  • What would his mom think if he left medicine?

  • Why is he so attached to prestige metrics?

  • What does it feel like to know you want medicine to be a “side” thing?

  • Now that money isn’t the biggest issue, how does he decide what to do?

You can listen here in your favorite podcast app or here on YouTube:


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