All Star Options Articles

Quick note before we get into this week’s Jam Session:

Yes, volatility mean-reverts. But don’t get caught assuming that just because $VIX is printing multi-month lows, it must spike soon. That kind of thinking can get you chopped up....

The S&P 500 is the greatest trend-following strategy ever invented.

Seriously.

Think about it. All it does, year after year, is kick out the losers and add the winners. It’s systematic. Cold. Unemotional. And this is...

We’re in a bull market.

Opportunities are flying at us from all directions—strong breakouts, explosive moves, momentum everywhere you look.

And yet… many of us feel like we’re missing out.

Like we should have caught that one...

I got a call last night from my friend...

I’ve been thinking a lot lately about the role self-compassion plays in trading.

Most traders I know—including myself—are pretty damn good at beating ourselves up. We hold ourselves to impossible standards. We expect precision,...

Trying new things is hard.

It doesn’t matter if it’s a new trading strategy, a new instrument—like moving from stocks to options or options to futures—or a new way of doing research… newness brings discomfort. It’s awkward. You don’t know what...

I’ve said this before, and I’ll say it again: I never really know which trades are going to be my biggest winners.

Sure, sometimes I get a setup that checks all the boxes:

• Price action looks great
• volume confirms
• ...

I took profits today in a Bull Call Spread on Robinhood ($HOOD). The trade was working, the options didn’t expire until January, and price action was moving in my favor… so why close it now?

Let me walk you through it.

I put the trade on...

I talk a lot around here about the “Hundred-Dolla-Roll.”

For those unfamiliar, it’s a phenomenon I’ve observed many times in trading: When a stock approaches a big, round number—$100, $200, $300—for the first time, it often...

I started a local trading meetup group back in 2013. At the time, I just wanted to create a space for people like me—people obsessed with markets, charts, setups, psychology—to gather in person and talk shop.

What I didn’t fully realize at the...

This Independence Day weekend, let's seek freedom from guilt.

As a trader, I carry around a lot of guilt.

Guilt for missing a huge winner.

Guilt for not getting out sooner.

Guilt for not holding long enough.

...