My new book, The Long Game, is now available for pre-order. Inside, you’ll find reflections from 30 investors who have endured multiple market cycles and lived to tell the tale. It explores how to filter out the noise that fuels doubt, manage the fear and greed that sabotage decisions, and anchor yourself to principles that truly compound wealth over time. The book ships at the end of February 2026.
In October 1915, British explorer Ernest Shackleton set out on one of the boldest expeditions in history: crossing Antarctica on foot. Inspired by Roald Amundsen’s South Pole success, Shackleton saw this journey as the final great prize of Antarctic exploration.
He and twenty-seven crew members sailed aboard the Endurance, pushing through the treacherous Weddell Sea. Then the pack ice closed in.
At first, it was gradual. Days turned into weeks as the ice tightened its grip. The ship groaned under pressure. The crew waited, watched, and hoped—even when they knew hope was thin.
On October 27th, Shackleton gave the order to abandon ship.
They stepped out onto the ice, temperatures plunging to minus twenty-five degrees Celsius. No rescue was coming. Survival was uncertain.
One crew member later recalled that Shackleton stood calmly on deck, cigarette in hand, “serious but somewhat unconcerned.” No melodrama. No visible panic. He encouraged each man as they climbed down:
“Don’t forget your diary.”
“Bring your banjo.”
All twenty-seven survived.
Over months, Shackleton led them across drifting ice, through open seas in a lifeboat, and eventually to safety. It remains one of the most extraordinary survival stories ever told.
When I recently reread Alfred Lansing’s Endurance, I couldn’t help but see Shackleton’s ordeal as a powerful metaphor for investing—specifically, for what I call the problem of the “second self.”
The Two Selves Inside Every Investor
Think about investing on a calm Sunday afternoon.
There is a version of you who thinks clearly. This self has read Buffett and Munger. It understands that markets are volatile in the short run. It believes in compounding, patience, and discipline. It creates a thoughtful, rational investment plan.
This self is steady.
But then the market falls 20%.
Suddenly, another version of you appears.
This second self checks the portfolio before breakfast. It scrolls through bearish headlines. It constructs convincing arguments about why this time is different. It begins to question everything.
And here’s the unsettling part: this second self is not foolish. It is eloquent. It can build airtight cases for panic. It can make the calm version of you feel naïve.
Every investor carries both selves.
The first self builds the plan in moments of clarity.
The second self must live with that plan when the world feels like it’s collapsing.
And those are very different conditions.
Process vs. Pressure
We talk endlessly about having a process—an investment philosophy, asset allocation, risk framework.
But there’s a quiet truth we rarely acknowledge:
Designing a process is intellectual.
Following it under stress is emotional.
The first is strategy.
The second is character.
Ancient Indian philosophy offers a word for this steadiness: sthitaprajna—a person whose wisdom remains undisturbed by sorrow, pleasure, fear, or attachment.
When Arjuna asks Krishna what such a person looks like, the answer is not about intelligence. It is about equanimity. A mind that does not swing wildly with circumstance.
For years, I thought this was an ideal reserved for saints or philosophers.
Now I think it describes the gap most investors spend their careers trying—and often failing—to close.
Knowing Your Second Self
No one can teach you how to conquer your second self.
You can only observe it.
You can only understand it.
You can only build a relationship with it over time.
That relationship is forged slowly, across many market cycles.
The next time markets fall and you feel urgency rising inside you, pause. Ask:
Which self is guiding me right now?
Shackleton standing on that sinking ship was not fearless. He had simply built enough understanding of his fear that it did not overpower his judgment when it mattered most.
That is the real long game—in investing and in life.
Not eliminating fear.
Not pretending volatility doesn’t matter.
But knowing yourself deeply enough that when the second self arrives—and it will—you recognize it.
And you are not surprised.
That quiet self-awareness is where compounding truly begins.