Why I'm Not Selling

But I Kinda Want to Sell

Random Words from our sponsor, Public.com

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Jeff’s Random Words

This week’s podcast is about things you should know before buying a stock. I’d like to invert that and talk about selling. I’ve said a few times on the podcast that I am trying not to sell any stocks in 2024. There are a few reasons for this. First, I think when I look back at my past sell decisions, I can safely say I was impatient. Between May and December of 2023, I sold a bunch of stocks. Here are a few examples of where I would have been better off (from a returns standpoint) had I not sold:


Total Return on Sell Date

Total Return if I still held today

Cloudflare (NET)



Disney (DIS)



Digital Realty Trust (DLR)



Pinterest (PINS)



PubMatic (PUBM)



Target (TGT)



Of course, it’s natural to look back at these as mistakes. Maybe they were. I really won’t know for a long while. Some I am happy I sold because I no longer was interested in following them, for a variety of reasons. Others I think I was impatient with. Had I still owned them I would view them differently today and perhaps even have added to them. Again, I don’t know yet if that would have been the smarter decision.

Another reason I’m trying not to sell anything in 2024 is that I’ve come around to the idea of leaving the losers in my portfolio as a reminder of past mistakes. I don’t think this is always smart. If a losing stock you no longer have conviction in represents a significant amount of money, I would sell and put that cash towards a better idea. But in my case, everything I sold in ALL of 2023 amounts to about 1.5% of my invested wealth, and it served as some tax loss harvesting. 

So for me, reminders that sit in the red at the bottom of my portfolio serve a useful purpose because I’m forced to reflect on them. If they’re in my portfolio, I follow them. I’ve learned that about myself. I’ve also learned that stocks sometimes come back from the dead. By keeping them around, I can see signs of life and perhaps capitalize on an opportunity the market hasn’t identified yet.

But this explanation is not why I write this today. It’s actually because I am struggling with my no-sell rule. There are some stocks I really want to ditch. One stock, Etsy (ETSY), is actually making me angry (If I have to read about Etsy’s “right to win” one more time…). So here I am, using our newsletter as my financial therapy.

If I am being honest, I’m not sure I will make it to January first without selling anything. And even if I do, I have a feeling I’ll sell some early in 2025. This self-imposed sell restriction was more of a thought experiment than a hard rule. At the very least, I am adding friction to my process, forcing myself to slow down, which I think is a good thing overall.


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