🤑 When to Sell? Strategies to Secure Your Profits

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This is Yoann—I hope you're doing well!

Today, we're going to try to answer a question every investor asks themselves:

When should I sell my assets?

When should you sell your assets?

Introduction

Investing just for the sake of investing doesn't make much sense.

We generally invest for a very specific reason, such as:

• Preparing for retirement.
• Funding your children's education.
• Traveling.

Or for more vague but equally important reasons, like buying yourself time in the future (my personal reason).
That means at some point, you'll need to sell your investments to finance your projects.

However, sometimes it can be relevant to sell your assets even if you don't directly need the money.

Should I sell my Nvidia shares because they’ve skyrocketed? Should I sell my Alibaba shares because they’ve dropped sharply?
We'll explore a few reasons that might lead you to sell shares or any other asset—and a few strategies you can use to sell these assets and generate profits.

A few warnings:
- This list is not exhaustive.
- These are not strategies for day traders who buy and sell multiple times a day or week.

Why sell an asset?

Reason 1: an emergency, you need cash

This is the worst reason and you should avoid it at all costs. Selling investments out of necessity—not by choice—should never happen.

Unfortunately, this situation may occur for various reasons, and that's OK; you just need to bounce back. In short, your safety net is supposed to be there to prevent this kind of situation.

Good to know: If you absolutely need cash and the only solution is selling your shares or life insurance policy, consider a lombard loan. It lets you borrow money by pledging some of your assets (such as shares). During the loan term, you only pay interest and you have to repay the whole loan at the end.

Reason 2: it was planned

You’re retiring, buying a new home and need a down payment, paying for your children’s education, etc.

Not much to add here. There are strategies to optimize your portfolio as retirement approaches, but that's not today's topic. We'll cover it another time.

Reason 3: the investment was a mistake

Sometimes you have to say goodbye to a bad investment.

You need to be able to accept a loss and not get too attached to an asset. This applies to everything: crypto, stocks, life insurance policies with high fees your banker pushed you into, even real estate.

Reason 4: to seize a better opportunity (arbitrage)

I’ve sold some of my stocks/ETFs several times to take advantage of an opportunity in another stock.

Example: when Meta’s share price crashed in 2022, I sold some of my red stocks to buy Meta shares. I preferred selling losing stocks to “benefit” from the capital loss for tax purposes.

The logic: investing in stock X by selling stock Y at a loss may earn you more in the long term.

Reason 5: to rebalance your portfolio

If you’ve set percentage targets for your portfolio’s different assets, you may need to rebalance if some explode.

If crypto rockets, they might represent 50% of your portfolio. In this case, it’s wise to sell some and buy stocks or ETFs.

No rule on how often—I do it 2–3 times a year, sometimes less. A simple Google Sheet keeps track.

Reason 6: to generate profits and cash—or to reinvest later

Some sell to generate profits and reinvest later when prices are lower. This is “profit taking” or “take profit.”

The idea: buy an asset, set a sale price to realize a profit. Example: buy 1 bitcoin at $30,000, sell at $60,000, profit of $30,000.

Some profit taking strategies

I’m in the “forever DCA” camp—so I buy regularly and rebalance occasionally. DCA (Dollar Cost Averaging) means investing the same amount at regular intervals, for less stress.

Here we’re covering long-term strategies, not short-term trading.

What is profit taking or take profit?

Buy an asset (stock, crypto, bond), set a price at which to sell and take profits.
Example: buy 1 bitcoin at $30,000, sell at $60,000.

What are the advantages and drawbacks of profit taking?

• Removes emotion and bias, locks in profits, buy back cheaply.
• But markets are unpredictable: you may miss further upside if the asset keeps rising.
• Transaction costs and taxes can add up, especially for stocks.
• In crypto, you can convert to stablecoins to avoid fiat conversion and taxes.

@hts-cm’s strategy

“Scale-out”: sell gradually as prices rise.
Example: sell 25% of bitcoins at $70,000, then 10% every additional $10,000. Adjust figures for your case.

Fixed profit target: Pick a percentage or amount—commonly 20–25% profit is a good selling point.

Changing fundamentals: When a company’s growth slows, sell some shares bit by bit.

Scale-out to secure initial capital: When the price doubles, withdraw 50% or your initial investment. On the remainder, take 25% out each time the price doubles again.

Bonus: buy and hold forever (or almost)

Buy and never sell except when truly needed or to rebalance. DCA lets you buy at various prices and smooth your average price over time.
Good to know: Many platforms let you automate profit-taking strategies or set price alerts.

Conclusion

I hope this edition helps clarify your asset-selling strategy.

My advice for beginners: don’t worry too much about selling, especially if your investment horizon is long. Set up your strategy and stick to it—the profits will follow.

Yoann ❤️

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