The Hardening Of The Great Softening

Miles To Go Before We Sleep

This is a weekly newsletter about the art and science of building and investing in tech companies. To receive Investing 101 in your inbox each week, subscribe here:

---

Apologies for the delayed send out. After 2.5 years, I've come the second closest to missing a week in my writing that I’ve come due to a busy work week, a retreat in San Diego, and a reunion. The last time was in October 2023 when I got deathly sick. Alrighty. Onward.

For some reason, right around summertime each year I find myself reflecting on the nature of work and my relationship with it. In August 2022, I wrote "Toil We Must." In April 2023, I wrote "The Renaissance of Rise and Grind." Each time, I find myself reflecting on the nuanced contradiction that working hard can be both empowering, and soul crushing.

Given we're kicking off the month of June, I guess its about that time for my thoughts to start wandering back in that direction.

Another thing that has been on my mind lately in this vein is a country song I heard recently. My wife was just commenting that she never realized how much I liked country music, but its one of those things that I loved as a kid, my cooler older brother didn't, and so I changed my personality. But I've come back to it over the last few years.

The song I heard is called "Buy Dirt" by Jordan Davis and Luke Bryan. The premise of the song is getting advice from an 80-year old. His advice?

"Find the one you can't live without
Get a ring, let your knee hit the ground
Do what you love but call it work
And throw a little money in the plate at church
Send your prayers up and your roots down deep
And add a few limbs to your family tree
And watch their pencil marks
And the grass in the yard
All grow up
'Cause the truth about it is
It all goes by real quick
You can't buy happiness
But you can buy dirt."

That line about finding something you love, and calling it work. It strikes me how difficult that is. How impossible it feels. And for a lot of people, it can be one of the greatest struggles they experience. That they spend so much time doing something they don't love. Why do we do that? And is it good or bad?

As most of my favorite topics are, its importantly nuanced. I'm a firm believer in working hard. But I recognize the hollowness so many people feel about the working world. And its important for people to build a better relationship with their work, sense of satisfaction, and force ranked prioritizations that dictate what type of work you're going to do.

Miles To Go Before We Sleep

The first thing I was reminded of as I started to unpack my feelings on this topic was a poem by Robert Frost, called Stopping by Woods on a Snowy Evening:

“Whose woods these are I think I know.
His house is in the village though;
He will not see me stopping here
To watch his woods fill up with snow.
My little horse must think it queer
To stop without a farmhouse near
Between the woods and frozen lake
The darkest evening of the year.
He gives his harness bells a shake
To ask if there is some mistake.
The only other sound’s the sweep
Of easy wind and downy flake.
The woods are lovely, dark and deep,
But I have promises to keep,
And miles to go before I sleep,
And miles to go before I sleep.”

I don't remember where I first read this poem, but I have often thought about it when I find myself stopping to reflect. When I've mowed half a lawn, or reached the peak of a hike but still have to get back down. I feel exerted, and spent, but still pleasantly tense with the expectation of further work to do.

I think of the impatient horse focused on the work, and the reflective narrator pondering the snow. The beauty that the work horse misses in its impatience to get to a farm, and out of the snow, is what was worth noticing. It’s the snow storm that makes the forest beautiful. The shelter needs the storm to be relevant. Life’s difficulties and complexities are what makes it important.

You can't escape a discussion on hard work without the acknowledgement that hard work is important. Mentally, physically, socially, we are programmed to feel discontent with stasis. We seek progress, and improvement. We yearn for something. For the religious folks, I often think of it this way; we are creations of "the most creative Being in the universe."

People's frustration is not with that concept; that natural pull to create and work for something. The frustration is with the environment in which they feel incapable of doing something they feel worth doing. Not something their boss feels is worth doing; they have a different value equation. But as a worker in a system, what is their work contributing to? And this isn't a new phenomenon.

What's Old Is New

I loved the book Walt Disney: The Triumph of the American Imagination by Neal Gabler. Walt Disney is a quintessential creative and builder. One of the greatest inspiration-fed storytellers. But early in the book, you hear stories of Disney's abusive father. A perpetually disappointed entrepreneur who is rarely gainfully employed, he takes out his frustration on his kids. Beating on them.

There are countless heartbreaking stories of parents who, in their own fits of personal disappointment, take it out on their children. Rather than being lifted by the accomplishment of their kids, they grow to resent them for their blank slate. Walt Disney's creativity, in many ways, grew out of that abuse. Drawing was an escape. His love for his own children, and every child, grew out of the relationship he did NOT get from his own father.

Some might reflect and say, "well, his trauma inspired one of the greatest storytellers of all time." But that's not good, right? Would we rather rob the world of Disney's empire if it meant he could have had a loving father? Would we erase Michael Jackson's discography if it meant he was raised by parents who loved and encouraged him? The answer should be yes! The fear is that many people would say no. To many, it's more important that the individual contributes to the whole than it is the individual is taken care of, despite the consequences for the whole.

Unfortunately, that hasn't been true for the majority of human history. Human's have rarely been able to do what people want to do today; follow their passions. Do what they love and call it work. Instead, people saw a direct correlation between their work and literal survival. But when I think about generations of people who simply worked to survive, I don't think we've been perpetually depressed as a society. In fact, some would say we're getting sadder and sadder.

Capitalism, for all it accomplishes, is a system that can easily emphasize enrichment of the few as a result of the work of the many. A friend of mine once said, "I'd rather have capped upside and ensure fewer people suffer. But capitalism takes the top off and the bottom off." I've written before about a mentor of mine who expressed a similar sentiment in a different way:

"Most organizational hierarchies are structured like a pyramid. Lots of people at the bottom, a few people at the top. And a lot of people like that structure, because the bottom is capped. But that, by design, means the top is capped too. To fully uncap the top, or in other words open up the maximum potential, you also have to open up the bottom. You have to open up the possibility that you might fail."

For many people, that uncapped upside is worth every risk or externality. Ambitious people often see themselves as "temporarily embarrassed millionaires." Success is not a question of if, but when. But for many people who see less and less success for them or people like them, there is a deep rooted frustration. And that frustration softens the ambition people feel, or the willingness they have to endure hard work.

The Great Softening

Last August, a song called Rich Men North of Richmond by Anthony Oliver took people by storm. And quickly it became politically polarizing; liberal and conservatives both sprinted to attach themselves for or against different aspects of the song. But by and large, it resonated meaningfully for a LOT of people. Here's just some of the message:

“I've been selling my soul working all day
Overtime hours for bullshit pay
So I can sit out here and waste my life away
Drag back home and drown my troubles away
It's a damn shame what the world's gotten to
For people like me, people like you
Wish I could just wake up and it not be true
But it is oh, it is
Livin' in the new world with an old soul
These rich men north of Richmond
Lord, knows they all just wanna have total control
Wanna know what you think, wanna know what you do
And they don't think you know but I know that you do
'Cause your dollar ain't shit and it's taxed to no end
'Cause of rich men north of Richmond”

For some people, that frustration has led to depression, anger, and feelings of hopelessness. For others, they've experienced a "great softening." In both my previous "work" pieces I touched on this idea of quiet quitting, and people deciding that work just doesn't matter as much as they thought. That phrase, “The Great Softening,” has resonated with me ever since I saw this TikTok of a "dock worker" expressing his changing views of work:

"People want to know why the supply chain is breaking down? It's because workers like me are breaking down. I don't wanna be out there unloading crates for Amazon. You know what I really wanna do? I wanna write poems. I wanna read Carl Jung and Sigmund Freud and explore the endless depths of the human experience. And you can't do that out there; on the docks. You do that in [your heart]. You do that [in your mind]. The supply chain's breaking down because we're breaking down. We're breaking down our walls. A great softening is occurring. And maybe that's not such a bad thing."

Now, people are quick to point out that the video is meant to be a joke; the guy isn't really a dock worker. But, as I've written several times, "there is a little truth in every JK." And that guy spoke truth.

So in a world where ambition can be powerful, and we want to seek truth, and build the future, what can we say about a huge swath of the world that doesn't feel that same ambition? That same drive to accelerate? Because, whether you like it or not, you can't accelerate a society despite itself. Society crumbles or ascends based on its collective ability to believe in something. The American Dream isn't a policy, or the result of a political party. It is a collective fever dream of people believing something hard enough to make it happen. But without that belief in a better life as the result of hard work, we can build all the rockets, robots, and AI we want. But society won't be lifted in spite of itself.

Lack of Tangibility

As we diagnose the feelings of helplessness, there is a myriad of social and economic factors that I don't have the time or qualification to address. In particular, I won't address it because the best context I've seen came from (I think) a Noah Smith post that showed that rather than all millennials being worse off than their parents, its more that the income inequality effect has been exacerbated. So the difference between the top 10% of millennials and the bottom 10% is much more significant than the top and bottom 10% of previous generations. (If someone knows what post I'm talking about, would love help finding it so I can address it later. I'm super bummed I can't find it.)

But if we focus in particular on how people think about work, it seems one key aspect is the lack of tangibility. I was turned on to this HBR post from Linkedin called "If You’re So Successful, Why Are You Still Working 70 Hours a Week?" Some of her takeaways really resonated with me. This is a longy, but a goody, so I'm quoting it as best I can because I think it explains a huge swath of frustrated people's feelings:

“My research shows that our tendency to overwork and burn out is framed by a complex combination of factors involving our profession, our organization, and ourselves. At the heart of it is insecurity. The 500 interviews I conducted showed a pattern: A professional’s insecurity is rooted in the inherent intangibility of knowledge work—exacerbated by the rigorous ‘up or out’ promotion system perpetuated by elite professional organizations (EPOs), which turns your colleagues into your competitors.

Exacerbating this problem, EPOs deliberately set out to identify and recruit ‘insecure overachievers’ — some EPOs explicitly use this terminology, though not in public. Insecure overachievers are exceptionally capable and fiercely ambitious, yet driven by a profound sense of their own inadequacy. This typically stems from childhood, and may result from various factors, such as experience of financial or physical deprivation, or a belief that their parents’ love was contingent upon their behaving and performing well.

As the recruiters I interviewed explained, these individuals are immensely attractive to EPOs because they are entirely self-motivating and self-disciplining. The firm in effect tells the insecure overachiever, ‘We are the best in the business, and because we want you to work for us, that makes you the best, too.’ But upon joining the firm, insecure overachievers discover that the rigorous up-or-out policy exacerbates their insecurity and their fear of being ‘exposed’ as inadequate — and ultimately rejected.

In the short term, insecure overachievers respond by delivering exceptional performance. The tendency to hard work is reinforced by the strong culture of social control created by EPOs. On the one hand, this is comforting. Some professionals I have studied refer to their firms as being like a ‘family,’ or something even more intense. As one consultant described it, ‘When I first came here, I thought, This place feels like a cult. But now I have been here a while, I think it is great.’ Taken to extremes, the insecure overachiever’s sense of commitment can lead to extreme conformity and the normalization of unhealthy behaviors.

Paradoxically, the professionals I studied still believe that they have autonomy and that they are overworking by choice. They do not blame their orgs. Instead, they blame themselves for being inadequate. Their colleagues seem to be coping, and they take that as further evidence of their own inadequacy. They do not talk honestly to their colleagues about their problems, thus perpetuating the myth of the invincible professional, which encourages their colleagues to feel inadequate in turn. If they suffer burnout, they think it is their fault. Their EPO and its leadership are absolved of responsibility, so nothing fundamental changes.

As a result, by the time insecure overachievers become leaders of their organizations, they unconsciously replicate the systems of social control and overwork that helped to create them.”

I mean, my gosh. I can't think of much recently that has resonated with me more than this. At least 50% of working people are "knowledge workers." And so many of them feel this intangibility of their work. Add on top the intensely comparative culture we've built around ambition, accomplishmentism, and social media bragging. Everyone feels a lack of tangible achievement, which causes their insecurity to flare up.

I've written before about how, in high school, I stumbled into a fondness for Russian literature. I still remember my freshmen year of college when I finally read Anna Karenina. I'll admit, much of the book didn't resonate with me; the affairs and social intrigue. But one scene in particular was, for me, what I can only describe as an ascendent spiritual experience. I was laying on a couch in the common area of my dorm building, and everything around me fell away. The people playing pool. The conversations nearby. Everything stopped and I felt completely captivated by that scene. For those of you familiar with the book, it may be simply enough to say it was the mowing scene that did it for me:

"The old man, holding himself erect, moved in front, with his feet turned out, taking long, regular strides, and with a precise and regular action which seemed to cost him no more effort than swinging one's arms in walking, as though it were in play, he laid down the high, even row of grass. It was as though it were not he but the sharp scythe of itself swishing through the juicy grass.

In the very heat of the day the mowing did not seem such hard work to him. The perspiration with which he was drenched cooled him, while the sun, that burned his back, his head, and his arms, bare to the elbow, gave a vigor and dogged energy to his labor; and more and more often now came those moments of unconsciousness, when it was possible not to think what one was doing. The scythe cut of itself. These were happy moments. Still more delightful were the moments when they reached the stream where the rows ended, and the old man rubbed his scythe with the wet, thick grass, rinsed its blade in the fresh water of the stream, ladled out a little in a tin dipper."

The longer Levin mowed, the oftener he felt the moments of unconsciousness in which it seemed not his hands that swung the scythe, but the scythe mowing of itself, a body full of life and consciousness of its own, and as though by magic, without thinking of it, the work turned out regular and well-finished of itself. These were the most blissful moments.

Levin did not notice how time was passing. If he had been asked how long he had been working he would have said half an hour-- and it was getting on for dinner time."

That satisfaction we experience from seeing something measurable that we worked out or built; that is what satisfies the creative hunger inside of us. Physical labor can often be easier to offer that feeling. But with "knowledge work," unless you feel a sense of ownership over the thing that gets built; the publication, the company, the product, it's much harder to feel that satisfaction. And so you feel empty. That feeling of insecure overachieving traps you in this intense cycle of dissatisfaction.

That insecurity comes from the fact that most of us have ceded the judgement of our work and contribution to other people. Employers, investors, partners, strangers on Twitter. We've abdicated the accountability for our output to other people. That's why, like I wrote about in The Renaissance of Rise and Grind, people have decided to "just give up." We gave up judgement to other people, and then instead of taking it back, we just decided we can't live up to that judgement; so we're just giving up.

No Judge But You

Source: Twitter

In my career, I've always found myself straddling a wide aperture of different mindsets. From private equity to public markets to venture to "indie businesses" that aren't dependent on capital. And I think the juxtaposition of all these different mindsets have been important to me. The more time you spend immersed in just one mindset, the more you start to feel that there really is only one way to be happy or successful.

Justin Welsh is one of those people that operates in a very different world than my day to day. But this tweet struck me as incredibly valuable. So many people who have ceded their judgement to "founders, VCs, and Techcrunch" fall victim to this disruption diaspora. It feels like the only way to matter in this world is to build a multi-billion dollar business revolutionizing an industry. But that isn't true.

Different strokes for different folks. Everyone is responsible for determining their own quests, and what is important to them. What they'll optimize for. This doesn't mean people can forfeit the need for any kind of quest. A life lived for oneself alone will never fail to leave the liver hollow (both the person doing the living and the organ, probably.)

I love, and return often, to a piece called "Choose Good Quests" by Trae Stephens and Markie Wagner. As they explain:

"Quests tend to manifest as an objective we center our lives around. Your quest might be to reach a specific milestone: to become a senator, to publish a book, to make a million dollars. But not all quests have an end state. You might be on a quest to maximize your net worth, or to bench-press more weight than anyone else at the gym. Maybe you’re just on a quest to have the most fun possible before you die. A far cry from refrigeration or running water, but a nice life. As you’ve probably already intuited, not all quests are created equal. In the most simple terms possible: a good quest makes the future better than our world today, while a bad quest doesn't improve the world much at all, or even makes it worse."

Unlike mythical tales of destiny, magic swords, or commanding oracles, the reality is that no one chooses your quests for you. In the paraphrased words of the Monty Python fellow in the muck, "strange women, lying in ponds, distributing swords is no basis for a system of [anything]!" Your quest is a fundamental component of who you are. It can't come from a blog, book, conference, or cocktail.

One of my favorite pieces I've ever written is called "Playing Different (Stupider) Games." In it, I talked about how different investors have different strategies. Neither are good or bad, necessarily. And I didn't decry one as strategy as the "stupider game." Instead, I put it this way:

"Stupider games are not realizing that other people are playing different games. OpenAI is playing a different game. Capital agglomerators are playing different games. Chamath is playing a different game. One of the biggest obstacles to most of the systems in the world, whether its healthcare, criminal justice, mental health, housing, or capitalism itself—all of them are filled with people playing different games.”

If you don't realize that your work is part of someone else's quest, then you're playing the stupider game. Everyone needs to wake up and recognize that they are the only ones who will be responsible for the quests they pursue. The only way to be happy is to truly take ownership of selecting that quest. But one important caution: you have to want the consequences of your quest.

Want The Consequences of What You Want

For some people when they choose a quest, they tend to villainize the quests of others. I like Josh Wolfe, and I agree with him a lot. But recently I saw a tweet of his that I disagreed with. He's famous for the saying, "chips on shoulders put chips in pockets." He believes that for people to build something truly great, they have to have an intense dissatisfaction or disaffection. He takes this to the logical conclusion that, while mindfulness and meditation may be good for individuals they are "TERRIBLE for society."

Source: Twitter

Unfortunately, I think that means that Josh is likely the kind of person who would say that Walt Disney's dad needed to beat him so that the trauma could create that dissatisfaction that gave us one of the world's greatest storytellers. The output of the individual was worth the abuse or trauma that elicited the output. The means justify the ends.

I don't agree. I think what Josh is failing to do, and what many fail to do as I've written about several times now, is appreciate the nuance. Mindfulness, or self-satisfaction, can co-exist with dissatisfaction. Rather than being mutually exclusive, these can be healthy balances of different mindsets at different times in different circumstances. Derek Sivers has a great blog post entitled "Are you present-focused or future-focused?" He touches on this kind of nuance this way:

"Your values change your focus. Being in love or making art pushes someone towards a present-focus. Ambition pushes someone towards a future-focus.

Both mindsets are necessary. You need a present-focus to enjoy life. But too much present-focus can prevent the deeper happiness of achievement. (I call this “shallow happy” versus “deep happy”.)

I wish all of this was part of a common understanding, the way we understand when extroverts want to go out for excitement, and introverts want to stay home with a book.

This concept even helps me understand myself when I’m acting out of character. If I’m acting too undisciplined, I realize it’s because I’ve stopped vividly seeing my future. I can only see the present. If I’m acting too disconnected, I realize it’s because I’m obsessed with my goals. I can see only the future."

Just like you're responsible for finding your own quest, you're also responsible for finding balance between being present-focused and future-focused. A word of caution though. People who think like Josh Wolfe, and optimize exclusively for their future-focused outlook, they can look to the late Utah billionaire Larry H. Miller for a warning. In his autobiography, that he literally finished dictating notes to his co-writer on his deathbed, he had some deep regrets:

"On May 1, 1979, he began operating Toyota of Murray in Murray, Utah, and he couldn’t know what he was beginning. Upon his death nearly 30 years later, he owned movie theaters, auto dealerships, a motorsports park with a world-class racetrack, a movie production company, an advertising agency, ranches, restaurants, TV and radio stations, a real-estate development company, an NBA franchise, a professional baseball team, an NBA arena, sports apparel stores—nearly 90 companies in all, in six states, with 7,000 employees, all under the umbrella of The Larry H. Miller Group, which produces $3.2 billion in sales annually, ranking it among the 200 largest privately owned companies in the United States.

But did you know that he worked six days a week, dawn to bedtime, for 20 years and missed his children’s youth, and that it was his greatest regret? In his own words, 'The lesson, of course, is to take care of yourself, to make time to eat and sleep and exercise. I learned that lesson too late. Yes, I would do some things differently. Aside from regrets about not spending more time with family, I would enjoy life more. I would spend more time doing the things I love to do.'"

He died at the age of 64. He didn't take care of his body. He didn't engage with his wife or children. He was a good man, and a generational business man. But at the end of his life he regretted it. He regretted not spending more time with his family. Not seeing his children grow up. The key takeaway for me from his life is if you want greatness here, you may have to sacrifice greatness there. He failed to embrace any present-mindedness because he was wholly captivated by future-mindedness.

When I wrote "Toil We Must" in 2022, there was section called "Growth Is Good" that, upon re-reading it, struck me as just as poignant to me today as it was two years ago:

I don't know about every other country but certainly in the U.S. we have a bit of an obsession with GDP growth. It's in the news all the time and we think about it constantly as a scorecard of national economic health. And it can be one important metric. But it shouldn't be such a guiding light.

"GDP measures everything except that which makes life worthwhile." (Robert F. Kennedy)

I consider myself a progressivist. I want more technology. I want more progression. I want to solve hunger and poverty, but I also want to go to different planets and virtual realities. I want everyone to find happiness and be their best selves, but to also have as much money and resources as they want.

But I'm also a big believer in personal growth, not just economic growth. I want people to be happier and working more or working less is not the deciding factor of happiness. Building a resilient mind and a rewarding life; that's what leads to happiness.

So instead of focusing on "not working hard," I wish we would spend more time learning how to "do hard work well." How do people find work they love? How do people set boundaries for what they are and aren't okay with? How do they communicate those boundaries? How do they motivate themselves when they're afraid? How do they become more self-aware of what their body needs (sleep, a walk, sunlight).

Control Your Own Destiny

I'm realizing my thinking this week has pulled heavily from my past writing. Another example that came to mind as I wrap up with this section was something I wrote a few weeks ago in my piece Tail That Wags The Dog:

"In a perfect world, investing should be an act of taking your world view and deploying capital to try and shape reality to that world view. If you believe a future is optimal, you should try to help build it. Investments become a lagging indicator of your beliefs. Often, however, the opposite happens. Whatever investments you end up making can play a big role in shaping your world view. Investments become a leading indicator of your beliefs."

I've written several times about taking control of your own destiny as well. In "Toil We Must" I ended with this idea:

"A good founder will hire a qualified person. A great founder will help all of their people become more qualified. More fulfilled. More capable. Great companies should make great people.

And often people have a hard time divorcing "extremism" or "obsession" with "greed." They quote the idea of everyone's death bed regret being, "I wish I hadn't worked so hard." But there is one other regret that is more poignantly articulated:

"I wish I’d had the courage to live a life true to myself, not the life others expected of me. This was the most common regret of all. When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even half of their dreams and had to die knowing that it was due to choices they had made, or not made."

Controlling your own destiny is reclaiming the definition of your quest in order to judge for yourself what tangible satisfaction you want to pursue. I'll leave with this final thought from a commencement address Denzel Washington gave:

"If you don't fail you're not even trying. I'll say it again. If you don't fail you're not even trying. My wife told me this great expression; 'to get something you never had you have to do something you never did.' Les Brown's a motivational speaker you made an analogy about this. He says imagine you're on your deathbed and standing around your deathbed are the ghosts representing your unfulfilled potential. The ghost of the ideas you never acted on. The ghosts of the talents you didn't use. And they're standing around your bed, angry, disappointed, and upset. They say 'we came to you because you could have brought us to life,' they say. 'And now we have to go to the grave together.' So I ask you today, how many ghosts are going to be around your bed when your time comes?"

As we all seek to do work that is meaningful. To build companies that are meaningful. To hire people to build meaningful things. Whether we like it, or not, it will always come back to an individual equation. Each person is responsible for articulating how they will judge their own life. What will matter to them when all is said and done. And as long as we continue to cede that responsibility to other forces we will remain unfulfilled. But as soon as we reclaim that responsibility, even if we fail, we will know what satisfaction truly is.

---

Thanks for reading! Subscribe here to receive Investing 101 in your inbox each week: