Past Passport

Past Passport

What I Got Wrong About Options

On risk, restraint, and learning later than planned

Joseph Pickett's avatar
Joseph Pickett
Jan 29, 2026
∙ Paid

About 160 million Americans invest in the stock market. I’m one of them. I’d spent years assuming that buying stocks was the “safe” default, without really thinking about how open-ended that risk actually is.

For years, I lumped “options” in with risky day trading — swinging for a left-field fence 400 feet away. Making money fast, but possibly losing it just as fast. Accounts like that can blow up in an hour.

But I was wrong.

What surprised me last fall was this: options don’t always increase risk. In some cases, they do the opposite - they force you to define your risk tolerance upfront.

Instead of discovering an undefined risk after the account blows up, you decide ahead of time what you’re willing to risk to make a certain gain. The trade is built from that pre-determined limit.

That realization at an older age shifted how I think about markets and my role in them. I’m not cut out for a high-adrenaline win followed by a soul-draining loss. I need a structure that survives my mistakes -…

User's avatar

Continue reading this post for free, courtesy of Joseph Pickett.

Or purchase a paid subscription.
© 2026 Past Passport · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture