Sell a long term position when one of these is true:

 


You already hit your “freedom number.” If the goal is reached and you are locking in lifestyle security, reducing risk, or shifting into more stable assets, selling can make sense.


The fundamentals broke, not just the price. Revenue model changes, margins deteriorate, leadership issues, regulation, or the company loses its edge. If the business is no longer what you originally bought, it is not a “hold,” it is a new decision.


They lost their moat and fell out of the top tier. If they are no longer one or two in the space, and competitors are clearly winning, that is a real reason to exit.


Permanent capital loss risk is rising. Too much debt, weak balance sheet, dilution, shrinking market, or “hope” is the strategy.


Risk rules were violated. If you use a stop-loss or max drawdown rule (example: 25%), you follow it. A long term timeframe is not an excuse to ignore risk management.


Opportunity cost is too high. Even if it might recover, your money could work harder elsewhere in a stronger business or better trend.

 

 

In short: Do not sell just because you are scared or because the headlines are loud. Sell when the goal is met, the thesis changes, the moat is gone, or risk management demands it.

 

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Sell a long term position when one of these is true:
&nbsp;
<ul>
<li>
You already hit your &ldquo;freedom number.&rdquo; If the goal is reached and you are locking in lifestyle security, reducing risk, or shifting into more stable assets, selling can make sense.
</li>
<li>
The fundamentals broke, not just the price. Revenue model changes, margins deteriorate, leadership issues, regulation, or the company loses its edge. If the business is no longer what you originally bought, it is not a &ldquo;hold,&rdquo; it is a new decision.
</li>
<li>
They lost their moat and fell out of the top tier. If they are no longer one or two in the space, and competitors are clearly winning, that is a real reason to exit.
</li>
<li>
Permanent capital loss risk is rising. Too much debt, weak balance sheet, dilution, shrinking market, or &ldquo;hope&rdquo; is the strategy.
</li>
<li>
Risk rules were violated. If you use a stop-loss or max drawdown rule (example: 25%), you follow it. A long term timeframe is not an excuse to ignore risk management.
</li>
<li>
Opportunity cost is too high. Even if it might recover, your money could work harder elsewhere in a stronger business or better trend.
</li>
</ul>
&nbsp;
&nbsp;
In short: Do not sell just because you are scared or because the headlines are loud. Sell when the goal is met, the thesis changes, the moat is gone, or risk management demands it.
&nbsp;
Subscribe and watch more videos here: https://www.youtube.com/@EarnYourLeisure
Join the EYL community for deeper training and a more detailed approach: https://www.eyluniversity.com
Join the number one stock club in the world: https://www.ianinvest.com
Invest Fest | August 7-9, 2026 Grab early bird tickets now: https://www.investfest.com

Welcome to The Earn Your Leisure Podcast. Rashad Bilal and Troy Millings will be your host. Earn Your Leisure will be giving you behind the scenes financial views into the entertainment and sports industries as well as highlighting back stories of entrepreneurs. We will also be breaking down business models and examining the latest trends in finance. Earn Your Leisure is a college business class mixed with pop culture. We blend the two together for a unique and exciting look into the world of business. Let’s go!! #earnyourleisurepodcast

Earn Your Leisure

When To Sell a Stock

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