Calibrating Your Process: Should You Track Your Trades? Even The Ones You Don't Make?

My thoughts on keeping tabs on the ones you sold or never bought

This investing thing is hard.

It can be difficult to separate skill from luck, so as investors, we’re always trying to develop some kind of pattern recognition.

Lately, I’ve been thinking about a deceptively simple question:
Should you track your sold positions? Or the ones you passed on?

It’s a messy question. There’s nuance, psychology, and a lot of hindsight bias. I try not to fall into the trap of “resulting” (as Annie Duke describes in Thinking in Bets), but that doesn’t mean I ignore outcomes altogether. Sometimes the best way to refine your process is to revisit your decisions with honest reflection.

I’ll go over some of my thoughts and at the end of the post, I’ll share what I do. Enjoy.

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Tracking Positions After You Sell

There are many valid reasons to sell. Below, I outline a few that come up in my own process—along with examples.

Thesis Busted

Your original thesis isn’t playing out. Not just being “early”—but fundamentally wrong.

Maybe the company’s competitive position was weaker than you thought. Maybe growth was lower, costs higher, or you simply overestimated your understanding of the business.

In that case, I think selling is a win.

Example: I bought MTLO.v, then realized I had it wrong. I didn’t care where it went after—I just wanted out.

Trust in Management is Broken

Sometimes, the issue is management.

If I don’t trust management to make rational, shareholder-friendly decisions, I’m out. That could mean poor capital allocation, being overly promotional, lacking capital markets savvy—or worse.

Example: I sold QIPT because I didn’t trust that leadership could navigate operations or capital allocation effectively. That doesn’t mean I’d never own it in an arbitrage context, but not as a core holding.

Positioning & Portfolio Rules

This one is more mechanical. Maybe a position gets too large relative to your portfolio, and you trim it—regardless of thesis.

Example: I trimmed VMD in early 2023 and CPH in 2024 simply because I felt overexposed.

Valuation

This one seems to have the most polarizing effects.

Of course at some point things get too expensive to justify holding. If you are quantitative investor, there is a good chance you sell “early”. This can be pretty hard to endure especially if you post about it on X. If it’s something that is currently popular, you will get put on blast.

Example: I trimmed XPEL starting in the $40s and continued selling as it pushed past $100. I looked dumb for a while—but I was following my process.

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Tracking Positions You Pass On

Do you track companies you almost bought—but didn’t? It depends on the type of pass.

Cursory Passes

These are stocks I glance at and immediately discard: Maybe it’s a junior gold miner, a large cap tech stock with a 10x Price/Sales ratio, a biotech stock that moons due to a positive phase 3 trial result, something in some other part of the world that I will never invest in, etc. Could you imagine if you are one of the lunatics very thorough investors who goes A through Z on SEDAR. You pass on thousands of business. Imagine trying to track that.

Close Calls

For me, I would have to feel like I know the business and the bet in order to track it after I pass. I just pass for a small reason. Examples of “close call” pass reasons:

• Slightly rich valuation

• Ownership structure concern

• Waiting for clarity on a risk

• Hoping for a pullback that never comes

This category is worth watching—because it reflects where your filters are most sensitive.

Examples:

• FTG.to in mid-2023. I thought the market would punish them for digesting an acquisition.

• VHI.to in late 2023. Solid story, met management, but I waited for a pullback that never came.

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Grading the Decision: What Matters?

If you track positions, how should you think about outcomes?

Timeframe is Everything

If you sold stock in a company at $10 and a few weeks later it’s at $12, was that a bad decision? I mean it went up another 20%. That’s 20% you left on the table. How about if it’s goes to $20 in a year? That’s another 100% gain on when you sold. Or worse, it multi-bags after you sold. These can be soul crushing. It’s hard enough to find a multi-bagger, so having it slip out of your hands can take a toll on a person.

These are assuming that the stock goes up. But what if it goes down? You sell at $10 and it drops to $8 or $5 or even lower. Then selling was the right decision with hindsight, right?. But we live in a world of probabilities. So maybe that bet wasn’t actually a bad bet and you should make similar bets understanding that they all don’t perform well.

How about if the stock goes sideways for an extended period of time, say 3-4 years. Maybe it was expensive and has to grow into it’s multiple. Many investors view hanging onto a stock during this time as bad. I think it’s nuanced. Yes you could sell and try to find another stock that will perform well. In doing so you may find something that performs well, you may also find something that performs poorly. No investor bats 1.000. Another thing that happened is you may have taken on more risk by adding a new position. If you knew the existing business and management well, then it will take time and energy to find a place to put that capital.

What You Did With the Capital

If you sell something and it drops 20% but use the capital to buy something that drops by more than 20%, you didn’t make a good decision with hindsight.

If you pass on something that outperforms your relevant index, but what you keep in your portfolio does even better, then you make the right decision.

Maybe you just sit in cash after you sell something. Over an extended period of time, cash will underperform the markets, so that’s something to consider.

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What I Do

Here’s how I handle this in practice.

I Keep a Decision Journal

This is the one habit I’d recommend to any investor.
It keeps me honest about why I made a decision, before hindsight creeps in.

I use Journalytic, but you can use pen and paper, Notion, spreadsheets—whatever works. I used to use pen and paper like a boomer.

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Cursory Passes

I don’t track these. Trying to do so would be overwhelming—and pointless.

Thesis Busted

I generally don’t track these after I sell. I like to just move on and use this to recalibrate my analysis process.

There are times when I want to see if my thesis being busted is as dire for the business as I think it was. Many times with microcaps with limited financial resources, a break in the thesis could mean a financing on poor terms.

Broken Trust in Management

If it a company where I don’t trust management or my thesis was busted then I move on and forget about the company. I may use it as a data point for something to watch out for in future business analysis, but I don’t look at the stock price.

Positioning

If I trim a position but it remains in the portfolio, I will track the sale. This is less about the specific bet or outcome and more about portfolio construction. Meaning should I loosen up my position sizing rules or button them down a bit more. Since I still have a position, then I’m tracking the stock regardless. This incremental effort is minimal.

Valuation

If I sell because of the valuation then tracking it may make sense. Again, this is very personal. If you are an investor that has a hard time owning “expensive” stocks then watching something continue to march higher can be torture. Remember 2021? Things that made no sense, continued to make no sense for quite awhile. This is where timeframes need to be calibrated.

I know we are all trying to learn and adapt to markets. But if you can’t own something because it’s too expensive, but can meet your financial goals owning something else, who really cares. I mean if you are running money, you must take such things into consideration, but if it’s just your capital, it’s really just your rules. The pendulum for increasing valuation lasts many years and unless you time the top, you are early and may beat yourself up for no reason.

Positions I Pass On

I track the ones where I did real work and passed for a marginal reason.

These still sting. But they teach me where my process might be too conservative.

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Final Thoughts

Psychology Matters

Even if the odds are in your favor, if I can’t sleep or feel like one bad move could knock me out, I’ve sized too big. Staying in the game is the only rule that matters long-term.

Personal Capital vs. Running Money

All of this is based on managing my own capital.
If I were running money for others, maybe I’d think differently. Probably. But I’ll never know for sure.

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How Do You Track?

That’s my process. It’s imperfect, always evolving, and tuned to my psychology.

I’d love to hear how you handle it. Do you track trades after you sell? What about close calls?

Thanks for reading.
– Dean