Multibaggers and Skeletons: Who We Think We Are

There is a person in almost every social gathering who won't pick up a hammer to hang a painting.

They know this about themselves. They've learned it the slow way, through stripped screws, uneven frames, the particular frustration of a job that looked simple and wasn't. They've made peace with it. They call someone.

The same person will open a self-directed brokerage account without hesitation.

It is about who you might get to be.

Not a better investor, necessarily. A different person. More decisive. More skilled. More right. Someone whose judgment the market has validated. Someone with a story worth telling at the next gathering rather than listening to someone else's.

The investing account becomes a place where that version of yourself might finally exist. A place where the sense of agency that can feel elusive elsewhere might finally be exercised.

Investing is uniquely seductive for this purpose.

The language sounds like expertise before any outcome has arrived. Thesis. Conviction. Position sizing. The feedback is delayed long enough to sustain the illusion. A crooked nail is visible immediately. A bad trade thesis can look like patience for months.

I had a client I had worked with longer than almost anyone else.

The relationship had been built over years, through market cycles and life events, through the kind of accumulated trust that only comes from having been there for both.

At some point he opened a self-directed account.

He mentioned it during a review. Casually. The way you mention something you're slightly proud of but don't want to oversell.

A few months later he mentioned it again. This time with more enthusiasm. He had found something, a position that had moved significantly. A multibagger. He walked me through the thesis, the timing, the return.

I listened.

The dangerous part wasn't that the first position went up. It was that it went up enough to become evidence of a new identity. He was, as a good outcome can make you feel, certain he understood something the market had only recently recognized.

Over the next several reviews he brought it up again. The account was growing, and the position continued to validate his belief in his own judgment.

Then he stopped mentioning it.

Not abruptly. Gradually. The way a topic fades when the story it was telling has changed.

I noticed the silence before I said anything about it. A few reviews passed. I waited, the way you wait when you sense something has shifted and you want the other person to find their way to it.

Eventually I asked.

Could I see the statement?

He showed me without hesitation. The multibagger was still there, smaller now, but present. Around it, a series of other positions. Each one a thesis. Each one, by the numbers on the page, a loss.

The account overall was underwater.

He didn't need me to say anything. The statement said it.

What he said, after a moment, was this:

I think I got lucky with that first one. I didn't have the discipline to replicate it. I kept thinking I understood something I probably didn't.

I didn't say I told you so.

Not because I was being polite. Because that sentence would have ended something that had taken years to build. The relationship wasn't built on me being right. It was built on me being present through enough cycles, enough decisions, enough moments when the outcome didn't match the intention, that he could say what he said without it costing him something.

The multibagger story is not necessarily dishonesty.

Every room has someone telling one. What the room never hears is the other story. The position held too long after the thesis had clearly broken. The account that grew quietly smaller while the winning trade was being discussed elsewhere.

Those stories exist behind the winning versions we rarely hear.

They just don't get told.

And told often enough, to enough people, in enough rooms, the edited story starts to replace the unedited one. The problem isn't simply that luck can masquerade as skill. It is that luck can imitate skill for long enough to make the distinction almost impossible to see from inside the story.

We don't compartmentalize as well as we think. The person who procrastinates in life procrastinates on the sell decision. The person who needs to prove something elsewhere brings that need into every trade they make.

The portfolio is not a separate rational domain. It is an extension of the person making the decisions. All of them. Including the parts that don't get mentioned at the review.

The skeletons don't disappear.

They wait. In accounts that stop being mentioned. In positions that quietly become smaller. In the gap between the story told in the room and the statement that tells a different one.

The advisor who has been there long enough holds something the client eventually loses sight of: the unedited version of themselves.

Not superior knowledge. Continuity. They remember what the client believed before the first big winner. What actually happened. What the client said afterward. What they subsequently forgot. How the pattern repeats.

The client changes the story they tell themselves. The advisor has seen the previous versions.

That is not a small thing to hold. It takes years to build the kind of relationship where someone will show you the statement. Where the silence can be noticed and the question can be asked without it feeling like an accusation. Where the admission, I got lucky, I lacked discipline, can be made without the relationship absorbing a cost it can't recover from.

Every investor has both.

The multibagger and the skeleton. The story told in the room and the one that stays in the account.

The question is whether the version of yourself you brought to those decisions is the one you think you brought.

The account doesn't lie.

It just waits until you're ready to read it that way.

Diptes Basu writes about investing, behavior, and decision-making, drawing on twenty-five years in global financial markets.

This essay reflects the author's personal views and is intended for educational purposes only. It does not constitute investment or financial advice.