Your style doesn’t serve your life. And markets are ruthless about exposing that.
I’ve never heard this articulated quite this way before, but once you see it, you can’t unsee it.
I knew someone who was a devoted student of classical value investing. A true believer. He quoted the greats, talked about patience, talked about virtue, talked about “doing things the right way.”
Recently, he was sentenced to six years in prison for insider trading.
When you read the court filings—when you actually listen to the motives—it becomes painfully clear what happened. This wasn’t about greed in the cartoonish sense. It wasn’t some adrenaline-fueled gamble.
It was desperation created by mismatch.
He cited the same things everyone cites when the mask finally slips:
Taking care of family
Making sure a parent’s mortgage was covered
Ensuring stability and recognition
All reasonable human needs.
But here’s the uncomfortable truth:
If your style truly worked for you, you would never have needed to abandon it.
Style Is Not an Aesthetic Choice
This is the part people refuse to confront.
Investment style isn’t about identity.
It isn’t about ideology.
It isn’t about sounding smart at dinner.
It is a tool for converting time, stress, and risk into outcomes.
And if the tool cannot close the gap between:
what you need
what you want
and what your life actually demands
then eventually the pressure forces a rupture.
Some people blow up accounts.
Some people lie to clients.
Some people reach for information they “shouldn’t have.”
The form differs.
The cause is the same.
The wildest risk is not volatility.
It’s not drawdown.
It’s not even leverage.
The wildest risk is operating inside a framework that cannot satisfy your real constraints.
Because once the gap becomes unbearable, people don’t calmly rebalance.
They jettison.
And the jump is rarely graceful.
If your style requires:
constant external validation
moral flexibility under pressure
or “one exception” to make the numbers work
then the problem isn’t discipline.
The problem is that your style doesn’t serve your life.
And markets are ruthless about exposing that.
Fantastic piece. The mismatch between what investment styles promise versus what they actually deliver is rarely discussed openly. I tried implementing a value investing strategy a few years back but needed liquidity for a real estate opportunity, which revealed this exact tension between theory and pratcice.