January 2026

Calm Seas Don’t Make Sailors

A while back I texted one of my best buds, Don, who I used to skate with, saying I was thinking about starting up again. My concern, I told him, was that every time I would go for a run, I couldn’t convince myself to hurl my body at the ground, so maybe I wasn’t ready.

When I finally did start skating again, I was reminded that it can be embarrassing to get in front of everyone, not be very good, and fall on your ass a lot. And as I just realized my largest loss ever in the market, I’m here now to fall in front of you this month.

I heard Tony Hawk say in an interview, “I don’t like getting hurt; I’m just not afraid to,” and I like that.

I’m not one of those “pain doesn’t bother me” dudes. Pain, both physical and emotional, hurts and I avoid it just like most rational people. Problems can arise from too much avoidance and not leaning into some discomfort from time to time.

I can remember early on having to spend a whole weekend wondering if I was cut out for trading after dealing with several large losses. There have been times where I thought about not skating or continuing this site because of the struggles that I have to overcome each time.

I can tell myself that I’m not very good or that things aren’t coming easily or quickly enough to me. We all deal with this form of self-talk, so it’s important to recognize it and have a plan for how to deal with it.

Don’t just blindly accept it. Maybe even try to prove it wrong.

All Pain, No Gain

Okay, so usually, when I’m talking strategy on here, I’m referring to the selling of options. What we’re about to discuss is buying options and the dangers associated with doing so.

With this being a riskier strategy, and one that I obviously haven’t figured out yet, I have chosen not to explain or recommend it on this site as of now. I hint at it from time to time as some of my biggest wins this year came from buying calls. But as we’re about to see, it’s also the cause of my largest loss ever.

Here’s the drama. Bezos dumped a bunch of his Amazon stock, causing the price to dive back in September. These things happen, and sometimes they’re even planned well in advance as was the case here, so I jumped in thinking it was a good entry point.

So far, so good – except I make two small adjustments to my trading plan.

You see, I have the tendency to get a little nervous sometimes and close out these types of trades for a quick profit early on, only to watch them continue to go in my favor, essentially leaving money on the table. A common phrase you’ll often hear is, “Let your runners run,” and I was attempting to adopt it as I tired of feeling the FOMO.

Secondly, I had also picked up a little tip on how to slowly add on contracts over the course of weeks or months instead of going in heavy all at once, thinking I had timed it perfectly. It was described as dating the contract for a little bit, adding on one or two here and there as things move around, before committing and marrying it after some time, once the trade has proven to be successful.

These two seemingly harmless changes created a perfect storm in my portfolio that I didn’t have the sea legs for.

I slowly added on contracts, but sorta lost track as I was doing this between two different accounts. Before realizing it, I was over-leveraged. I had opened too many contracts and had way too much money at risk. To my credit, I did close half of the position in advance, but chose to let the other half ride. I bought these in September and they expired in January, leaving me to believe I had plenty of time.

But time comes for us all.

At the end of October, an earnings report was released and Amazon has great news for investors, causing the stock to skyrocket and the calls I bought were now at a profit of around $7,500, a return of 150%!

My thought process was that, surely now investors will pile in as it’s been riding the bottom for a bit. Lots of articles and several analysts raising their price targets by +$50, not something you see very often! Everyone and their mama was talking about how undervalued it was.

“The markets can stay irrational longer than you can stay solvent.” – John Maynard Keynes.

Then suddenly, for some reason, the nation seemed to collectively remember that our President was besties with our #1 pedophile. I was under the impression that we’d known this for a while. In the past few months, the markets have been temperamental as people seem to disagree with that relationship, understandably.

So what started as a $7,500 gain turned into a $4,606 loss. This is, no doubt, a hard lesson, major setback, and something I won’t soon forget. I’ve been in this play since September, so that’s a lot of ups and downs and what ifs that I’ve been dealing with on a daily basis. I’m glad to get this over with.

I have a renewed love for the safety of selling options after this experience. In November I said, “Some people only sell Cash Secured Puts far below the stock price in an attempt to never get assigned, effectively using only their cash to make money without owning shares. This is cool.” And this is exactly what I’ve been doing and I’m back to pulling in consistent profits again.

We’re gonna fail, that’s inevitable. What’s important is what you do afterwards.

In unrelated news, do YOU want to learn how to become a Hot Shot Options Trader?! Purchase one of my courses to unlock the secrets that hedge funds don’t want me to tell you!!

“The fool who knows his foolishness is wise at least to that extent, but a fool who thinks himself wise is a fool indeed.”
-Dhammapada, a collection of sayings by the Buddha.

Bio-Dome

There was a $150 million experiment in the 90s where they tried to simulate our ecosystem in a biosphere in the Arizona desert. It was a prototype for a future colony on Mars.

The environment thrived in the beginning. With everything under complete control and away from the chaos of the real world, they experienced vigorous growth, with many plants exceeding expected sizes.

But, what they soon discovered was the daily chaos of our environment was actually beneficial for the ecosystem. They found out the hard way that trees need wind to stay strong. Trees develop what’s known as stress wood, or reaction wood. When stressed by wind or other foreign objects, they trigger a change in their cellular structure in order to grow this stronger wood. This leads to their resilience.

The roots also suffered from what they called, “lazy root syndrome.” When wind pushes against a tree it creates tiny tears and stresses at the base of the trunk and in the roots. This causes the tree to send down extra nutrients and growth hormones to thicken the roots and push them deeper into the soil to anchor the tree. In the windless dome, this didn’t happen, causing the roots to stay shallow and weak.

The trees couldn’t stand on their own and the project was a failure.

You see my point with all this. Weave discomfort into your life.

Monthly Roundup

In January, I made… oh, wait, I’m down $3,461.

I made $1,145 but I gave back $4,606.

Here are the trades. As you can see, I sold a lot of Cash Secured Puts this month in an attempt to crawl my way back out of this hole.

I may not be green in the markets, but I’m green on the news!

So needless to say I’m at odds and ends.
But I’ll be stumblin’ away, slowly learning that life is okay.
Say after me,
It’s no better to be safe than sorry.

Take on me,
Chris

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