I was pumped to go into the office on Monday.
It was the first business day of 2026. I was ready to high-five the team, grab a coffee, and get the year moving.
But Sunday night, I got a notification: Your new laptop is scheduled to arrive Monday by 12:00 PM.
We’ve had some porch pirate incidents in my neighborhood lately. If I went to the office, that box would be sitting in my lobby, unattended, for 6+ hours.
So, I ran it through the Financial Zen Decision Matrix.
It’s a simple mental filter I use for everything from daily logistics to massive investment decisions. It looks like this:
OPTION 1: STAY HOME
UPSIDE: Risk of theft drops to 0%. I get my laptop safely.
DOWNSIDE: I miss the energy of the first day in the office.
OPTION 2: GO INTO THE OFFICE
UPSIDE: I get to start the year with the team!
DOWNSIDE: I come home to an empty porch, file a police report, fight for a refund, and wait weeks for a replacement.
THE FILTER: Which downside is worse?
It wasn’t even close. Missing one day at the office is a bummer. Getting my laptop stolen is a nightmare.
So, I stayed home.
This logic applies directly to your money.
Take Concentrated Stock, for example. We see this all the time – someone works for a successful company and 80% of their net worth is tied up in employer stock.
They hesitate to sell because they think, “What if it goes up another 50%?”
Let’s run the Matrix:
OPTION 1: Diversify (Sell the stock, buy a diversified portfolio)
UPSIDE: You eliminate the risk of a single company ruining your financial future. You secure your wealth.
DOWNSIDE: If the stock goes to the moon, you miss out on “maximum” returns. You get rich, but maybe not “buy a private island” rich.
OPTION 2: Don’t Diversify (Keep it all in one stock)
UPSIDE: If the stock doubles, you look like a genius. (Concentrate to get rich, diversify to stay rich).
DOWNSIDE: The company cooks the books, faces a scandal, or the market shifts. The stock goes to zero. You lose it all.
Think this doesn’t happen to “good” companies?
Silicon Valley Bank: Went from the 16th largest bank in America to seized by regulators in 48 hours.
WeWork: Valuation collapsed from $47 billion to bankruptcy, wiping out employee equity.
Wirecard: A blue-chip fintech darling that went to zero due to fraud.
Lehman Brothers & Enron: The classics.
The Filter: Which downside is worse?
“Missing out on extra gains” sucks. “Losing your entire life savings” is a life reset.
Therefore: Diversify.
The actual outcome doesn’t matter. Even if you hold the stock and it does double, it was still a reckless decision. You just got lucky.
Smart financial planning isn’t about chasing the highest upside. It’s about eliminating the catastrophic downside.