There’s an investing parable about two athletes training at the same gym. One is a powerlifter, built like a tank, who trains to lift maximum weight for a single rep. The other is a marathon runner, lean and efficient, who trains to steadily improve his pace for 26.2 miles. One day the runner notices a crowd gathered around the powerlifter, cheering him on as he achieves a new PR. "I want people cheering for me," the runner thinks. "I'm going to do what he's doing." He stops his run, walks up to the loaded bar, strains to lift it, and throws out his back. What went wrong? The runner tried to win someone else’s game.
As lawyers, we do this to ourselves, whether we realize it or not, all the time.
We read about the trial lawyer who just secured a massive jury verdict and feel like our transactional practice is boring. We look at the Managing Partner who works 80 hours a week and drives a Porsche, and we feel inadequate for prioritizing our schedule to coach our kid’s soccer team. We look at the solo practitioner with total autonomy and feel stifled by our firm’s requirements.
Know what game you want to play. If you're a marathon runner, run. If you're a powerlifter, lift. But if you're a marathon runner chasing a powerlifter's trophy, you'll be a miserably mediocre runner and you'll never get the applause you're chasing.
The Dangerous Allure of Other People’s Games
Financial writer Morgan Housel calls this "playing someone else's game." His insight: most bad decisions come from taking cues from people playing a different game than we are. The long-term investor who panics and sells because a day-trader is freaking out on TV. The lawyer who measures success by billable hours when their actual game is being home for dinner with their family.
Law is particularly brutal for this. We're ranked from day one, law school class standing, Best Lawyers lists, billable hour leaderboards circulated firm-wide, biggest verdicts. The profession pushes a single definition of winning: More.
More hours, more prestige, more money.
But "More" is not a strategy. Unless your game is more for an intended reason, then more is you running on someone else’s treadmill.
If your game is building a practice that lets you coach your kid's soccer team, measuring yourself against the lawyer grinding toward seven figures isn't just demoralizing, it's a strategic error. If your game is maximizing income, lamenting your lack of family time is needless torment. In both cases, you're taking emotional cues from someone whose finish line is in a different zip code.
Comparison Is the Thief of Joy
Charlie Munger, who was a lawyer before becoming Warren Buffett's partner, had a blunt take on professional misery: "Envy is a really stupid sin because it's the only one you could never possibly have any fun at."
His point: the world isn't driven by greed, it's driven by envy. Most people aren't satisfied doing well. We need to be doing better than our neighbor.
Naval Ravikant sharpens this insight: envy is an illusion because you can't cherry-pick the good parts of someone else's life. If you aren't willing to trade your entire existence, including your family, your struggles, your baggage, for theirs, then your envy is pointless.
Munger offers a reality check: “someone will always be getting richer faster than you. This is not a tragedy.”
When we envy another lawyer's career, we're cherry-picking results without accepting costs. We want the BigLaw partner's income but not their ulcers. We want the solo practitioner's autonomy but not their cash-flow anxiety. We want the trial lawyer's verdict but not their years of 80-hour weeks.
We're envying trophies from games we didn’t sign up to play because we don’t like those games.
Defining Your Victory Conditions
Brutal honesty: I've spent years trying to "win" at being a lawyer without ever defining what winning means to me. My scorecard has been external: verdicts that impressed other lawyers, income that looked good on paper, recognition that felt validating in the moment but hollow an hour later.
Here's the trap: measuring yourself by metrics that don't matter to you. It’s spending twenty years climbing, reaching the top, and realizing the ladder is leaning against the wrong wall because someone else put it there.
And I don't regret my path. It provided for my family, led to a firm I'm proud to be part of, and gave me a library of great memories and ridiculous stories.
But I know I can do better. We can do better.
So here's the question: What game are you actually trying to win?
Not the game your law school classmates are playing. Not the game the partnership track requires. Not the game that gets you ranked in Super Lawyers. Your game. The one where the victory conditions are set by what you genuinely value, not what impresses others.
I don't have this figured out. But I know my game involves work I find intellectually challenging, time with people I care about, and the freedom to choose cases that energize me. Your game will look different. That's the point.
So audit your ambitions. Look at what you're currently chasing and ask: Is this what I actually want, or just what a "successful lawyer" is supposed to want?
Let the powerlifters lift. Let the marathoners run. Figure out your game. Then play it.
