Last week, we covered the counterintuitive lessons that flip conventional wisdom on its head. Today, we're digging into something deeper: the meta-skills that separate sustainable success from lucky streaks.

These aren't quick tricks or “hacks”. They're mindset shifts that compound over time - much like the portfolios and plans we build together.

Matt Cheng was once Taiwan's #1 junior tennis player. Today, he runs Cherubic Ventures, a venture capital firm that backed unicorns like Flexport and Hims & Hers (which returned more than 500x his initial investment).

His core philosophy comes straight from Grand Slam tennis: you win by taking three out of five sets. You don't need to win every rally. "I can't be shortsighted and let a bad play get into my head when I'm on the court. I always need to focus every second on the next swing and not the point that I had lost."

Cheng tells the story of backing Andrew Dudum, founder of Hims & Hers, in 2017. Dudum's previous venture had failed, and most of his backers walked away. But Cheng remembered: it takes three sets to win in a best-of-five. One loss doesn't eliminate you from the match.

The parallel to long-term investing is almost too obvious, except most people still don't live it. A portfolio hitting a rough quarter doesn't mean the strategy is broken. A sector underperforming for eighteen months doesn't invalidate the thesis.

The skill is distinguishing between a temporary setback within a sound approach and an actual structural problem. Tennis taught Cheng to stay present, analyze what's actually happening, and adjust without panic.

What makes this especially relevant: Cheng operates under a single-general-partner structure. He's the sole decision-maker for his firm's investments. No teammates to share the pressure. No coach to call a timeout. Just him on the court, trying to win the match.

Which brings us to the next lesson.

There's a reason Cheng's firm structure is rare. Making decisions alone is psychologically brutal.

In tennis, timeouts are allowed only for injury. You get a couple of minutes to hydrate and towel off during set breaks. That's it. The rest is you, the opponent, and the choice you make in the next three seconds.

Cheng says this trained him for venture capital in ways that team sports never could. When you can't diffuse responsibility across a group, your decision-making sharpens. You own outcomes completely.

This echoes something we saw with Vanessa Selbst's move from poker to Jane Street. She left professional poker partly because it became increasingly competitive and isolating. What drew her to Jane Street was the return to collaborative problem-solving - the culture reminded her of early 2000s poker forums, where players dissected strategies together.

Here's the tension: solo decision-making builds conviction and clarity, but isolation breeds blind spots. The best operators toggle between the two modes. They gather input, pressure-test ideas, invite criticism - then ultimately decide alone and own it.

In financial planning, we often see this balance. You're the ultimate decision-maker for your financial life. But going it alone, without challenging your assumptions or testing them against someone else's experience, is where people drift into danger. It's why we exist - not to make choices for you, but to make sure you're seeing the whole board before you move.

Kenneth Rogoff is both a chess grandmaster and a Harvard economist who's worked at the IMF and Federal Reserve. His career has been about reconciling two opposing instincts: when to move fast, and when to slow down.

Betting games - poker, blackjack, Figgie - train you to pounce the instant you spot an edge. Hesitate, and it's gone.

Chess does the opposite. It rewards cool reflection at critical moments. Rogoff describes playing chess as "almost viewing it as fighting for your life, even though you're not." The intensity forces you to control your nerves, think methodically, and resist impulsive actions.

As IMF chief economist, Rogoff opposed a 2001 bailout for Argentina. He recalls: "When the clock is ticking and you have to make a move, sometimes in chess you need to rely on intuition and analogies." But he also emphasizes the discipline of pausing before finalizing decisions. "If you don't, you just end up making mistakes."

So which is right - speed or patience?

The answer is both, and knowing which mode the situation demands. Market dislocations require fast action. Major life decisions - retirement timing, estate planning, selling a business - benefit from methodical review.

The mistake is applying one mode universally. People who always move fast make costly errors. People who always deliberate miss opportunities. The real skill is calibrating.

Chris Solarz has completed over 300 marathons, broken nine Guinness World Records, and once navigated all 468 New York City subway stops in under 23 hours.

That last one wasn't just endurance. It was optimization. Solarz and a friend spent four to five months obsessing over every detail: which minute of the day to start, which station, which direction, which route. They built a model in MATLAB that ran through trillions of solutions to find the shortest path.

"If it were purely about a recall game or pure intellect, I wouldn't be able to be at the top," Solarz says. "But if I can add in this extra little superpower I have, which is just being the most diligent over the longest amount of time, then maybe I have a chance to compete."

Today, Solarz is Chief Investment Officer of digital assets at Amitis Capital. Over 20 years, he's reviewed roughly 5,000 fund managers. His edge isn't genius-level IQ. It's a relentless, sustained effort applied systematically.

Here's the paradox: pattern recognition is the foundation of expertise, but it's also the thing that blinds experts. You see patterns because you've logged the hours. But once you see them, you stop questioning whether the pattern still holds.

Muller's "Think Twice" crosswords and Solarz's MATLAB models aren't about being clever. They're about forcing yourself to keep looking when your brain wants to stop. To check the assumption you've made a thousand times. To run one more simulation, even though you're pretty sure you've got it.

This is where most people plateau. They develop competence, pattern recognition kicks in, and they coast. The deliberate discomfort of re-examining what you think you know is what separates the good from the great.

These lessons aren't abstract philosophy. They're operating principles that show up in how we approach financial planning:

We don't panic over one bad quarter, a few quarters, or a bad year. Markets are a best-of-five match, not a single rally. A rough period doesn't invalidate a sound long-term strategy.

We challenge wins, not just losses. When a portfolio performs well, we ask whether it's skill or luck. Was the thesis correct, or did we just get the timing right by accident? If we don't know why something worked, we can't replicate it.

We optimize for "good enough" on routine decisions, and slow down on the big ones. Rebalancing portfolios doesn't require perfection. Retirement income strategies demand thoroughness. Knowing the difference matters.

We respect pattern recognition - and its limits. Experience teaches you what normally happens. But "normally" can change. The portfolios that thrived for 40 years might not be optimal for the next 40. We stay curious, even when we're confident.

We take responsibility for decisions, but we don't decide in isolation. You're the decision-maker. We're here to make sure you've considered the whole board.

The pattern across all these stories is striking: elite decision-makers don't treat games as escapes from their real work. They treat them as laboratories for skills that formal education never touches—acting under uncertainty, managing emotion, and developing intuition that moves faster than analysis.

You don't need to become a poker champion or a chess grandmaster. But the principles scale down just fine.

Stay present. Question your wins. Move fast on small decisions, slow on big ones. And remember: it's a best-of-five, not sudden death.

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