The Time I Had to Take a Bus Home for Thanksgiving (And What It Taught Me About Options)

Hey traders,

In Monday’s post, I talked about why I sell options — because the odds are in my favor as the seller, not the buyer.

But it wasn’t always that way for me. In fact, I had to learn this lesson the hard way.

Let me take you back to a time early in my career when I was still buying options, thinking I could hit a home run and cash in big.

I was working as a young stockbroker in New York, far from my hometown of Gary, Indiana.

It was almost Thanksgiving, and I had plans to fly home looking like a Wall Street hotshot.

But before I left, a buddy and I decided to split the cost of a “sure thing” option trade. Big mistake.

We watched that option drop, day by day, until it expired worthless. That money?

It wasn’t just for the trade — it was my only way to afford a ticket home for the holidays!

Long story short, I didn’t fly home as a Wall Street big shot. Instead, I ended up pawning my stuff and taking a long, humiliating bus ride home.

That loss stuck with me — but it also planted a seed in me. It started opening my eyes to how fast you can lose everything as an options buyer. From that moment on, my mind started opening to the possibility of flipping the game in my favor.

Stay tuned for Friday, when I share another life-changing moment that solidified my career as an options seller.

Trade well,

Jack Carter

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