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# The psychology of selling winners too early
- URL: https://www.investingvisuals.io/the-psychology-of-selling-winners-too-early/
- Published: 2026-07-05T14:00:50.000Z
- Updated: 2026-07-05T14:00:50.000Z
- Author: Jan (Investing Visuals)
- Tags: Investing visuals

### Introduction

When I ask fellow investors about their biggest mistake, it's nearly always "*selling a winner too early*." Myself included. At some point during our investing journey, we all seem to fall for it.

Which made me look into it more deeply, to understand the psychology behind it and prevent myself from falling into that trap again. For me, my biggest mistake was selling Tesla, which I invested in back in 2019.

The stock had a nice run, and I was up 350% on my position, so I sold, feeling like a genius. Only to see Tesla's stock take off in the years after. If I would've held, it would be a 25 bagger today.

![](https://storage.ghost.io/c/2b/10/2b10b2a9-bdc4-46ee-82c1-3e1e62e4af14/content/images/2026/07/This-one-stock.png)

### The psychology 

Selling winners too early comes down to **prospect** **theory**: losses feel roughly twice as painful as equivalent gains feel good. So the moment a position is up, your brain can flip into protection mode.

Then there's **regret** **aversion**. Watching a winner keep climbing after you sold it feels like failure, and the brain hates that more than missing the gain itself. So it takes the easy route: lock in the win, feel smart, move on, and don't look back.

I could be wrong about when the right exit is. We all can be. But I think the answer isn't willpower but **structure**. What has really worked well for me is defining my exit criteria before I buy, grounded in business fundamentals, not price relative to your cost basis. Price is not the thesis, the business is.

Doing so makes it easier to cut the weeds and water the flowers.

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**One-pagers*

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How they make money

## Latest articles

Portfolio update: all the highlights from June, including my buys, sells, thoughts on semi's and software and a lot more. 

[Portfolio update June: moving money toward bigger potential gainsThroughout the month, my focus has shifted significantly: I’ve rotated a sizable part of my portfolio into positions I believe have a much better risk/reward.![](https://storage.ghost.io/c/2b/10/2b10b2a9-bdc4-46ee-82c1-3e1e62e4af14/content/images/icon/Investing-Visuals-8653d366-c188-4cbc-aa84-1614a925de4a.png)Investing VisualsJan (Investing Visuals)![](https://storage.ghost.io/c/2b/10/2b10b2a9-bdc4-46ee-82c1-3e1e62e4af14/content/images/thumbnail/Cover-page-Portfolio-13f064f8-948b-41e3-ba90-8b161ef214f3.png)](https://www.investingvisuals.io/portfolio-update-june-moving-money-toward-bigger-potential-gains/)

Another portfolio update covering a new memory related position I opened in early June, breaking down why I bought it, my buy price and portfolio weight. 

[Why I bought this memory stockBack in April, I wrote a deep dive about the AI memory industry. The more I dived in, the more bullish I became for a number of reasons: \* The industry is dominated by just three companies: Micron, SK Hynix & Samsung \* Each GPU generation needs exponentially more memory \* The are very![](https://storage.ghost.io/c/2b/10/2b10b2a9-bdc4-46ee-82c1-3e1e62e4af14/content/images/icon/Investing-Visuals-48b32fd2-52ef-4f49-983f-5a7eeb7c1b3e.png)Investing VisualsJan (Investing Visuals)![](https://storage.ghost.io/c/2b/10/2b10b2a9-bdc4-46ee-82c1-3e1e62e4af14/content/images/thumbnail/Cover-page-Portfolio-1-b5d0cc8c-cc66-4f2b-987c-dbae7ab79a4c.png)](https://www.investingvisuals.io/why-i-bought-this-memory-stock/)

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## Up next

It's been a while since I published an industry special. It may have been quiet, but I've been working hard on my next deep dive, which covers the **energy** **industry**. I'm particularly proud of it because it's in co-development with a community member who works in the sector and provided a lot of valuable insights.

It is focused on AI data center energy in particular, because that's the main growth engine and the reason I believe there are some very interesting investment opportunities to be found, if you know where to look. The deep dive will be out this week!

And that concludes this week's newsletter. Thanks for reading, and have a wonderful day!

\~ Jan

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