All Star Options Articles

Due to the shortened trading day, we're going to cancel the Live Options Jam Session for this week.

But I didn't want to leave you without a quick update on positions that exited this week, as well as updated stops.

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.

Guilt for using the wrong strategy.

Guilt for being late to a major turning point.

It’s a long list. And it’s heavy.

This guilt doesn’t just live in the rearview mirror. It follows me into the next trade. It clogs up my decision-making. It makes me hesitate when I should act. It whispers, “Don’t screw this one up too.”

Can you relate?

Lately, I’ve been working on something that I think might help: forgiveness.

Not the fluffy, wishy-washy kind. But real, honest, intentional forgiveness.

Forgiveness for not being perfect.

Forgiveness for being human.

Forgiveness for not catching every move.

Because here’s the thing — I can’t catch every trade. It’s impossible. Especially in a bull market like this one, where new setups are popping up everywhere. There will always be winners I miss. There will always be hindsight that makes me wince.

But carrying all...

Today's trade follows a similar pattern of late --  High, tight consolidations continue to break out.

I've got another one here that is setting up for a breakout and I'm taking advantage of a recent pullback to get positioned at advantageous prices.

I had a thought this morning while considering a few trades:

Maybe part of why I still struggle at trading sometimes is because there’s a part of me that really, really wants to follow an instruction manual to be successful.

In other areas of my life, that mindset serves me well.

I don’t know how to cook—but give me step-by-step directions, and I thrive. When we used to get HelloFresh boxes delivered, I crushed those meals. I followed the instructions, made something delicious and useful for my family, and felt like a total champ.

Following the instructions = success. I like that. I crave that.

But trading isn’t like that.

I can lay out a well-thought-out plan—how to select the trade, how to size it, how to manage it—and still lose money.

The market doesn’t care that I followed the recipe.

There’s no gold star just for executing cleanly.

And yeah, I know a successful outcome in trading is supposed to mean I followed my plan with discipline. I know.

But that doesn’t make a loss feel any better. Which leads to the uncomfortable question I’ve been sitting with:

If I only thrive when I have a proven...

I'm traveling to Toronto with JC, Steve, and the rest of the team in September. It only makes sense that I should continue adding Canadian exposure to my portfolio. 

I wouldn't want to be an impolite guest, would I?

Today's trade is in a speculative Minerals Miner from Canada.

You remember Vanilla Ice. Don't pretend you don't.

He has nothing to do with today's trade, but the name of the stock reminded me of him.

Broker-Dealers are showing incredible strength right now, I want to get long the chart that looks the best of the lot.

Today I closed a winning trade. Booked a gain. The kind of thing I tell others (and myself) to celebrate.

So why do I feel bad about it?

Maybe “bad” isn’t the right word. More like unsettled.

Here’s the situation:

The stock had started to break down a bit on the daily chart, so I followed my process and exited. Textbook move, right?

But here’s what’s bothering me…

The stock is still above its 50-day moving average.

It’s still in a hot sector.

And I had January 2027 calls. That’s over 18 months until expiration!

With that much time, why did I feel the need to micromanage?

This is one of those moments where the trade was technically breaking support, yes — but the bigger question I’m sitting with is: Did I kneecap this trade too early? Did I cut off a potential monster winner because I was too zoomed in?

My risk was defined. I could’ve ridden it longer.

Maybe smaller sizing would’ve helped me let it breathe?

Maybe I’m just overthinking? (I do that.)

But one reminder that helps bring me back to center:

I can always get back in.

Just...

PROGRAMMING ALERT: I’m launching a new weekly show on StockMarketTV.com called What Are My Options?

It’s a 30-minute(ish) show where I take your requests for options strategies on your favorite stocks. I’ll drop a lesson or two along the way, and sometimes I’ll just riff on the philosophy behind options trading.

The first episode airs Tuesday, July 1st at 3pm ET—and I’ll be doing it live every Tuesday after that. It’s meant to be interactive, so I hope you’ll join me!

Lately, I’m noticing more people talking about how the market has “come too far too fast.” Some are even licking their chops, ready to jump in short and try to catch what they’re sure will be an “epic reversal.”

This kind of talk makes me uncomfortable.

Not because I disagree that a pullback could happen — anything can happen. But because I know the psychology behind this kind of positioning. It’s not usually about...

Today's trade goes into the "Hard Trade" bucket. 

I'm buying a stock that has rocketed up 30%+ in just 7 trading days.

But... it has only just cleared overhead resistance which might be the "all-clear" signal from the control tower to ignite the rocket boosters.

As a trader, I live by boundaries.

Stop losses. Profit targets. They’re there for a reason. They say, “This is as far as I’m willing to go.” They define my comfort zone — both for risk and for reward.

If a trade moves beyond my stop, I start losing more than I’m okay with.

If a stock races beyond my upper price target, I start to worry it’s overextended and due for a sharp correction.

These aren’t just technical lines on a chart — they’re psychological lines in the sand. And as much as I know they’re important, I’ll admit: boundaries are hard for me.

Sometimes I break them.

Sometimes I blur them.

Sometimes I forget why I set them in the first place.

And the more time I spend in the markets, the more I realize:

Trading teaches me about far more than markets — it teaches me about me.

Every time I ignore a stop loss or stretch a target, I’m not just failing as a trader — I’m revealing something deeper about how I operate. Because when I struggle to hold boundaries in my trading, it’s usually because I’m struggling to hold boundaries in other parts of my life, too.

In...

From a recent Strazza Letter, Steve mentioned: 

Semis just failed to complete a top relative to the broader market and are now reasserting their leadership.

If this risk-on group is in good shape, then stocks are likely to perform well in the future. So this is a positive development from a broader market perspective. 

So today's trade is in a lesser known semiconductor name that is atop the relative strength leaderboard.

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“You don’t need to take reckless risk. But you do need to stop treating your inner-knowing like it’s a dangerous enemy.”

That line’s been bouncing around in my head all week.

I talk all the time about the importance of having a plan and sticking to it. Because, truthfully, trading without a plan is just gambling with a more expensive costume on. I need a framework — some sense of what I'm trying to do, what I'm risking, and what outcomes I'm aiming for.

Planning is visualizing.

When I build a plan, I’m creating a map of what could happen — the likely, the unlikely, the hoped-for, and the dreaded. Mapping out scenarios helps me prepare emotionally and financially for what may unfold.

But sometimes, the market veers off-script. And in those moments, another voice enters the chat.

It’s not part of the plan.

It’s not in my trade journal.

It’s not even easy to explain.

But it’s real — and it’s been right more...