Why Holding Is Harder Than Buying

I bought my first position in 2017 and I have held some version of it since. In that time I have sold three times and regretted two of them. What I have learned is that the difficulty was never in the decision to buy.

Buying takes an afternoon. You do the reading, you form a view, you press the button. The act is bounded.

Holding is not an act at all. It is the absence of an act, repeated daily, under conditions specifically engineered to make you act.

The asymmetry nobody prepares you for

A purchase requires one moment of conviction. Holding requires that conviction to survive roughly two thousand consecutive days, several hundred of which will feature a reason to abandon it.

Each of those reasons will be articulate. Some will be correct. In 2018 the reason was that the entire sector had been a speculative mania and the assets were worth nothing. That argument was largely right about most of the assets and entirely wrong about a few, and there was no way to know which was which from inside the year.

What actually makes it hard

The position grows, and your tolerance does not. A holding that was two percent of your net worth becomes eight percent through no decision of yours. You never agreed to hold eight percent. And the moment you notice, you are managing a position size you did not choose, with all the anxiety that implies.

Your reasoning decays. The specific argument that convinced you in 2017 will not be available to you in 2020. You will remember the conclusion and not the reasoning, which means you will be holding on the strength of a feeling that you once had a good reason.

I now write down the reasoning, with dates. Reading the 2017 version back is uncomfortable and useful in equal measure.

Drawdowns last longer than attention. A seventy percent decline that recovers in three years is, in the arithmetic, fine. Lived through in weeks, it is eleven hundred days of a number that is worse than it was.

Other people’s exits are visible. Every sale by someone else is public and every hold is invisible. The feed shows you the people who got out and never the far larger number who did nothing.

What has helped

A written rule about size. If a position exceeds a set share, I trim it back on a schedule rather than on a feeling. The point is not the specific threshold. The point is that the decision was made in a calm month rather than a violent one.

Making access inconvenient. Long-term holdings live on a device in a drawer. The friction is not a security measure, it is a behavioural one.

Separating the working balance. A small amount stays liquid on the exchange I have used since 2021 for the occasional rebalance. Everything else is somewhere I have to make an effort to reach.

Reading my own old entries. The 2018 version of me was certain this was over. The 2021 version was certain it would never stop going up. Both were confident and both were wrong, which is a useful thing to be able to prove to yourself.

The part I have not solved

The feeling still arrives. Every significant drawdown produces the same internal argument, and it is no less persuasive for being familiar.

What has changed is that I no longer expect to feel differently. I expect to feel exactly that, and to have decided in advance what I will do about it, which is nothing.

That is the whole practice. It is not conviction. It is a rule made when calm, protecting you from the version of yourself that shows up at 2am in the third month of a decline.