I salivated this morning.

There’s no more dignified word for it. I opened my portfolio before the coffee finished brewing, the way you check the weather before deciding what the day will be, and there it was: my best-performing anchor position, up fifty percent on paper. In a couple of months. And before any of the careful, systematic machinery in my head could engage, a thought arrived - involuntary, specific, fully formed:

What would a well-placed call option on this company have done?

I didn’t summon the thought. I didn’t want it. But I knew the answer to the arithmetic before I finished asking the question, and for a brief moment I felt the pull of it in my chest the way you feel a wave tug at your ankles when you’re standing where the surf breaks. Not enough to move you. Enough to remind you that it could.

I want to be honest about that moment, because I think most investing writing skips it. The genre convention is to present discipline as a settled state - as if the person writing the newsletter about systematic long-term investing has somehow been vaccinated against the desire for fast money. I haven’t been. I spent years around markets. I know exactly what leverage feels like when it works, which is precisely why the thought arrived pre-loaded with imagery. The temptation wasn’t abstract. It was arithmetic with adrenaline attached.

So there I sat, a man who writes weekly about patience, doing envy-math on his own winner.

Then I did what the morning routine actually calls for, which is to look at the whole portfolio and not just the position that flatters me.

Eight anchors are placed now. The portfolio has a shape - an early one, the way a house has a shape when the framing goes up and you can suddenly stand where the kitchen will be. And near the bottom of the page was the other number, the one the salivating part of my brain had scrolled past: my worst-performing position, down twenty-five percent. Also in only a few months.

Here is where the story is supposed to go, according to every instinct wired into the human nervous system: the winner is the good decision, the loser is the mistake, and the intelligent move is to lean into what’s working and quietly re-examine what isn’t.

Except that’s not what I felt. What I felt, looking at the position down twenty-five percent, was something closer to appetite.

Because here is the strange, true thing I have to report from this morning: the position that is down twenty-five percent is the one I believe in most. Not despite my research - because of it. My conviction in that company’s decade is higher than my conviction in the one that’s up fifty. If you told me I could only keep one of the two for the next ten years, I wouldn’t hesitate, and I wouldn’t keep the recent winner.

Sit with that for a second, because it inverts nearly everything the market’s ambient culture teaches. Cut your losers, ride your winners is practically scripture - and in a trading context, where price action is the information, it’s often right. But I’m not trading. Over a few months, price isn't telling me much about a decade-long thesis. It’s telling me about sentiment, positioning, a rate print, a rotation - weather, not climate. The down-twenty-five position hasn’t disproven a single element of why I anchored it. The market has simply repriced its mood.

And when I realized that the red position was the one I’d defend hardest at a dinner table, the temptation collapsed. Not through willpower. Through irrelevance. You can’t salivate over a call option once you’ve remembered that you don’t actually know what the next few months hold- only that a few months was never the game you were playing.

In AIWB’s earliest days, before there was much of anything to protect, I wrote an essay making a public commitment: no options, no margin, ever, in this portfolio. I codified it in writing specifically so that I couldn’t talk myself out of it later, in some future moment when the arithmetic looked irresistible.

The Greeks had a name for this maneuver. When Odysseus wanted to hear the Sirens’ song without steering into the rocks, he didn’t rely on his discipline in the moment - he had his crew tie him to the mast before the singing started, while his judgment was still his own. Philosophers call it a Ulysses contract: a decision made by your calmest self, binding on your most tempted one.

This morning, the singing started. And the rope held.

What surprised me was what surfaced next. Not a rule I recited - a memory that arrived on its own, the way old advice does, after the temptation passes rather than before it begins. Warren Buffet’s two rules. Rule number one: never lose money. Rule number two: never forget rule number one.

I used to read that as a platitude, honestly - the kind of thing embroidered on pillows in the gift shops of finance. This morning I heard it differently. Buffett isn’t promising that positions never go red; his own holdings have been cut in half more than once and he held. He’s describing a posture toward risk: never put yourself in a position where a temporary price is a permanent outcome. An anchor position down twenty-five percent has lost me nothing yet - it’s an opinion the market is offering, not a verdict. A leveraged bet down twenty-five percent is a different animal entirely. One of those structures lets conviction do its work over a decade. The other doesn’t survive long enough to find out.

I keep turning over the fact that the temptation was real and the discipline held. I used to think the goal was to reach a state where the temptation stops arriving. I no longer believe that state exists - not for me, and I suspect not for you. Strong markets will always whisper the arithmetic of the faster path, and the whisper will always be loudest precisely when the system is working, when the winner is up fifty and the imagination has material to work with.

The goal isn’t to stop hearing the song. The goal is to have tied the knots earlier, on a calmer day, so that hearing it costs you nothing but a moment of honesty with yourself.

Eight anchors placed. One up fifty, one down twenty-five, six somewhere in between, and a decade of weather still ahead for all of them. I don’t know which of this morning’s numbers will look meaningful in ten years. I suspect neither.

If you’re an investor who understands all of this intellectually and still feels the pull - I wrote this for you, and you’re welcome to explore what we’re building at AI Wealth Blueprint whenever the timing feels right.

- Christopher Cinek
Founder, AI Wealth Blueprint

This content is for educational and informational purposes only and reflects personal opinions at the time of writing. Nothing here constitutes financial, investment, tax, or legal advice. Investing involves risk, including possible loss of principal.