A Learning a Day

A friend who is a lifelong New York Knicks fan has been eagerly following the New York Knicks these playoffs. Watching them sweep the 76ers and cruise back into the Eastern Conference Finals got me thinking.

Last year, the Knicks also made the Eastern Conference Finals — their deepest run in years. They lost to the Indiana Pacers. Then they fired their coach.

Their coach, Tom Thibodeau, had gotten them further than they’d been in a long time. Why change it?

But the pattern keeps showing up. The Chicago Bulls fired Doug Collins in 1989 after he’d taken them to the Eastern Conference Finals for the first time in 15 years. They replaced him with his own assistant, Phil Jackson. Phil Jackson instituted the “triangle offense”, a significant departure from the way they played. Six championships followed.

Similarly, the Golden State Warriors fired Mark Jackson in 2014 after back-to-back playoff appearances for the first time in decades. They hired Steve Kerr, who had never coached before and upset their players. Four titles followed.

In each case, the previous coach had done something real and hard. They’d built the culture, changed the trajectory, earned genuine loyalty. That’s what made the decision so difficult. And that’s also exactly why it had to be made — because what got them there wasn’t going to take them further.

The Knicks will likely not win it this year — both western conference finalists look formidable. But the decision to change already looks like the right one.

This shows up in companies and individual careers too. The skills and habits that create early success can quietly become the ceiling. Recognizing that — and doing something about it — takes a different kind of courage than just grinding harder.

What got you here won’t get you there.

“No one tells you running is 10 percent cardio and 90 percent negotiating with the voice begging you to quit.” | David Dack

Beautifully put.

And applicable to nearly every hard thing we attempt in our lives.

I recently started building products focused on healthcare affordability in the US. As I was ramping up on a new space, the biggest question that sparked my curiosity was: how did we get here? I plan to write about this weekly with the goal of chronicling the decisions, accidents, and breakthroughs that built the US healthcare system.

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In 1940, only 9% of Americans had health insurance. A decade later, it was nearly 50%. By 1960, almost 70%.

What changed? A wartime wage freeze.

In 1942, FDR signed the Stabilization Act — freezing salaries to combat wartime inflation. With millions of men at war, labor was scarce and wages were surging. The freeze was a blunt fix for an urgent problem.

But benefits were exempt. So employers competing for workers did the logical thing — they competed on health coverage instead. Henry Kaiser, owner of a construction company who was branching out into shipyards, was among the first to figure out how to cover his workers comprehensively, keeping his shipyard workforce healthier and more productive. Others followed fast.

Then in 1954, the IRS codified a tax exemption making employer health contributions tax-free for both employer and employee. A $500 health plan was now worth more than a $500 raise. The economics became self-reinforcing.

For millions of Americans, this was transformative. A factory worker in Ohio who had never seen a doctor in her adult life suddenly had coverage. She went in for a check-up. They found something early. She lived another 40 years. That story played out across millions of households.

In 1944, when jobs lasted a lifetime, few thought to ask the obvious question: what happens when you leave?

The answer took decades to arrive — and it shaped everything that came after.

Next week: Henry Kaiser’s health plan for his shipyard workers became something far larger. You almost certainly know his last name.

In the Netflix documentary “Court of Gold,” Steve Kerr — who won three championships as a player with the Chicago Bulls and four more as coach of the Golden State Warriors — shares a fascinating reflection on what winning cultures have in common.

A sheer intensity that comes from competitiveness and playing to win.

A sense of joy and fun while doing so.

And a genuine happiness when others on the team succeed — a collective delight in watching every person around you flourish.

It’s a lovely articulation. And when I reflect on my favorite team experiences, I find all three were present too.

“Examine the lives of the best and most fruitful people and ask yourselves whether a tree that is supposed to grow to a proud height can dispense with bad weather and storms; whether misfortune and external resistance…do not belong among the favourable conditions without which any great growth even of virtue is scarcely possible.” | Friedrich Nietzsche

The challenge and discomfort define the path.

I had the opportunity to attend our 10-year graduate school reunion recently. One of the themes that kept coming up for me: reminiscing about moments of impact.

For example, I met with someone and we swapped memories. I remembered a piece of advice they’d given me that was key to my response to an important question in a final round interview that led to my internship. They remembered something I’d done that had helped them and a few others in a meaningful way.

Neither of us had much memory of our own contributions — but we remembered the other’s vividly.

There were other stories like this throughout the reunion. A moment of kindness that left a deep imprint. A small act of help that had meant everything at the time.

Two things struck me. First, it’s easy to underestimate the impact we’ve had on others in certain moments — and overestimate how much they remember what they’ve done for us.

Second, in a moment of need, an act of kindness lands differently. The imprint it leaves is deep and lasting.

“You might entertain the notion that this concept of the shadow is somewhat antiquated. After all, we live in a much more rational, scientifically oriented culture today. People are more transparent and self-aware than ever, we might say. We are much less repressed than our ancestors who had to deal with all sorts of pressures from organized religion.

The truth, however, might very well be the opposite. In many ways, we are more split than ever between our conscious, social selves and our unconscious shadow. We live in a culture that enforces powerful codes of correctness that we must abide by or face the shaming that is now so common on social media. We are supposed to live up to ideals of selflessness, which are impossible for us because we are not angels. All of this drives the dark side of our personalities even further underground.

We can read signs of this in how deeply and secretly we are all drawn to the dark side in our culture. We thrill at watching shows in which various Machiavellian characters manipulate, deceive, and dominate. We lap up stories in the news of those who have been caught acting out in some way and enjoy the ensuing shaming. Serial killers and diabolical cult leaders enthrall us. With these shows and the news, we can always become moralistic and talk of how much we despise such villains, but the truth is that the culture constantly feeds us these figures because we are hungry for expressions of the dark side. All of this provides a degree of release from the tension we experience in having to play the angel and seem so correct. These are relatively harmless forms of release, but there are more dangerous ones, particularly in the realm of politics.

We find ourselves increasingly drawn to leaders who give vent to this dark side, who express the hostility and resentment we all secretly feel. They say things we would dare not say. In the safety of the group and rallied to some cause, we have license to project and vent our spleen on various convenient scapegoats. By idealizing the leader and the cause, we are now free to act in ways we would normally shy away from as individuals. These demagogues are adept at exaggerating the threats we face, painting everything in black and white terms. They stir up the fears, insecurities, and desires for revenge that have gone underground but are waiting at any moment to explode in the group setting. We will find more and more such leaders as we experience greater degrees of repression.” | Robert Greene, The Laws of Human Nature

I found myself reflecting this from three angles at once — thinking about my own shadow, about the pressure to conform that shapes a child, and about what that pressure does to society over time.

In every case, awareness remains the first step.

I’ve been asked a lot recently what it’s like to switch from a big company to a small startup. The analogy I keep coming back to: it’s like moving from F1 to Rally.

In F1, the racing is high-telemetry, high-precision. You have metrics for everything. You know the track — the turns are predictable, the speeds are calibrated, the causes are understood. And you go lap after lap after lap, optimizing seconds. There is risk, but existential risk is rare. There is a fundamental predictability to it.

That’s also how it works in a big company. A large part of the job is staying on that track and continuously working away on shaving off seconds.

Rally is something else entirely. Fast turns, unexpected turns. Moments where you’re flying off a bump — exhilarating — and then you realize you need to make a sharp right the moment you land, because if you don’t, you’re off the track. No telemetry. No map you’ve memorized.

That’s what being in a small company has felt like. The highs are real. The lows are real. The amplitude of both is much higher. And existential risk is real too. It requires a different mental calibration — because you can be just a few turns away from being off the track.

I hesitate to call it “fun,” because it’s a certain kind of fun. It won’t be for everyone. It depends on what you’re seeking and what your risk threshold is.

In the spirit of ending with another car analogy, your mileage might vary.

“Behind any vehement hatred is often a secret and very unpalatable envy of the hated person or people. It is only through such hate that it can be released from the unconscious in some form.” | Robert Greene, The Laws of Human Nature

You can always count on Robert Greene to say it as it is.

A few days recently where I found myself unable to think through a problem that was, objectively, pretty straightforward. The thinking was just muddled. In both cases, all it took was a good night of sleep and a run to clear it.

This got me thinking about resets — and how they work like fractals.

At the start of the year, after a real break, most of us come back with unusual clarity. What matters, what doesn’t – health, family, etc.

Then the day-to-day sets in, the noise accumulates, and that clarity slowly fades.

But it’s not just annual. The same thing happens at the start of a quarter, a week, a day. And then the pattern repeats.

The act of living — processing signals, good and bad, all day long — is an exercise in getting our heads muddled.

Our job is to keep finding the rituals that clear it.