I Had Cash and a Plan in 2020. I Still Sold at the Bottom.

I had cash ready. I had a plan written down. I still sold near the bottom in March 2020.

I’ve held positions for over a decade, and I’d like to tell you that experience protected me. It didn’t. Years before the crash, on some forgettable Tuesday, I’d written myself a rule: if the market falls hard, buy more. I even kept cash aside for exactly that. I was, on paper, the disciplined investor everyone tells you to be. And when the moment came, I did the opposite of my own instructions. I sold. Not everything, but enough to matter, and near enough to the low that I still wince about it.

For a long time I blamed the plan. Maybe it wasn’t detailed enough. Maybe I needed a better framework, a smarter allocation, a newsletter. But the plan was fine. The plan was almost embarrassingly simple and completely correct. The problem was that it needed my permission to work — and in a crash, the version of me that could grant that permission wasn’t in the room.

A plan you have to decide to follow isn’t a plan

Here is the uncomfortable thing about written plans. We write them calm. We read them scared. Those are two different people using the same handwriting.

The calm version knows that downturns are temporary, that trying to time the bottom is a mug’s game, that the whole point of a long horizon is to sit through exactly this. The scared version knows only one thing: the number is red and getting redder, and doing something — anything — feels better than sitting still. Behavioral researchers have spent decades measuring this gap. The pain of a loss lands roughly twice as hard as the pleasure of an equivalent gain. You are not weak for feeling it. You are human, and the market does not grade on a curve for good intentions.

So a plan that says “buy when it feels safe” is worthless, because it will never feel safe. A plan that says “stay the course” is worthless, because staying the course is precisely the decision your scared self is least equipped to make. If following the plan requires an act of courage in the moment, you have not written a plan. You have written a suggestion, and you will overrule it the second it costs you something.

Pre-commit the trigger, not the intention

What changed for me was small and boring, which is usually how the good changes look.

Instead of writing intentions, I now write triggers. Not “buy more when there’s a good opportunity,” but a specific level: at a 20% drawdown, deploy the first tranche. The market either hits that number or it doesn’t, and it does so whether or not I feel brave that week. A level is not a mood. It removes the one input — my nerve — that has failed me most reliably.

The second change was to stop trying to be a hero. I used to imagine deploying all my cash in one perfectly timed move at the exact bottom. That fantasy is why I froze: the stakes of getting it wrong felt enormous, so I did nothing until the fear flipped me the other way. Now I buy in tranches. Something at −20%, something at −30%, something at −40% if it gets there. I will never nail the bottom, and the tranches mean I no longer have to. Each buy only has to be right about direction, not timing. If it keeps falling, good, the next tranche is cheaper. If it recovers, good, I already started.

Remove the decision from the moment

The deeper principle underneath all of this: the job of writing something down is to leave your future self as little to decide as possible.

When the order size is already set, the levels are already chosen, and the cash is already earmarked, the scared version of me isn’t asked to be courageous. He’s asked to follow instructions that a calmer, better-informed person — who happened to be me — left behind. That is a much smaller ask. Discipline stops being a feeling I have to summon and becomes a checklist I merely have to not abandon.

And there’s one more thing that sounds trivial and isn’t: keep the rules where the fear lives. A plan in a drawer, or a document you have to go find, loses every time to a red headline on the phone in your hand. Put the rules on the same screen where you panic. Read them before you touch anything. The friction of one calm re-read has saved me from more bad moves than any amount of willpower ever did.

Boring is the strategy

None of this is clever. There’s no edge here, no signal, no secret. Pre-commit the level. Split the buys. Size them in advance. Keep them visible. It is deliberately, almost aggressively boring, and that is the entire point. The exciting version of investing is the one that sells you certainty in a moment when certainty is impossible — and it’s the version that talked me out of my own plan in 2020.

I still made the mistake I’m warning you about, with cash in hand and the rules already written. So I’m not writing this from a mountaintop. I’m writing it as someone who finally understood that the plan was never the weak link. I was. The fix wasn’t to become braver. It was to build something so dull and so automatic that bravery was no longer required.