I got an email this week with a question I get a lot:

“I’m up 280% on a position. Should I sell and realize the gains? I don’t currently have another stock I’d want to put the money back into. How should I think about taking profits?”

Making money in the market is what we’re all after right?

So why when it actually happens do we panic and start questioning whether or not we should take it?

In my experience, there’s two main reasons for this. The first is valid. The second is our financial system’s fault.

First is taxes.

No one wants to pay Uncle Sam more than necessary.

Valid. 100% agree.

The second?

Fear and uncertainty.

Time to bust that.

The short answer — yes.

However, the mistake most people make when a stock is up big is that they don't have a plan for what to do when it happens.

They bought it, it went up, and suddenly paralysis kicks in.

What typically happens:

But there is a better way.

When I'm up more than 50% on a position, I take 25% of my shares and sell them to lock in those gains. If/when the position climbs another 50%, I take another 25% off.

I keep doing this until I've pulled out all the money I originally put in.

Because at that point, I'm playing with the house's money and not my own.

Every dollar I still have in that position is now pure profit. Every gain from that point forward is pure upside. And if the stock tanks tomorrow, I've already won.

This is how you stay in the game without triggering large tax bills, or losing profits to the next market downturn.

The biggest mistake I see investors make?

They're up 100%+ on a stock and start to think they're a genius.

So they keep buying, and simply hold.

And hold. And hold.

Then the stock pulls back 40%. Or 60%. Or it gives up all the gains it made.

Until they’re right back at square one.

Except now they've experienced what 100% gains feels like, and breaking even feels a lot like losing.

Take the example of META stock (Facebook) in 2022.

That year, the stock suffered a historic plunge, dropping roughly 64% and bottoming out at ~ $90/share in November.

This represented a staggering 76.7% decline from its September 2021 high of over $382/share.

This proves the market doesn’t care how smart you think you are.

It doesn't care how much research you did or how ‘right’ your thesis was on the way up.

The investors who build real wealth are the ones who have a plan, follow it, and don't negotiate with it no matter what the market is doing.

You don’t have to use my 25% rule. Feel free to create your own.

But please, have a plan for taking profits.

Now let’s talk about what to do with them.

Here's where my strategy differs from a lot of other investors.

When I take profits from a single stock, I don't look for the next single stock to put the money into.

I put it into my S&P 500 ETF.

Or QQQM. Sometimes both.

Here's why:

The S&P 500 has averaged ~10-12% annually since the 1930s.

That's not a guess. That's based on 100+ years’ worth of data.

If I know I can reliably get that return in a broad, low-cost index fund over a long period of time, for me, that's the baseline everything else gets measured against.

Every individual stock I own has to clear that bar to earn its place in my portfolio.

I only hold a single stock if I have deep conviction that company is going to outperform the S&P over a specific timeframe, for a specific reason I can clearly state.

Not a ‘vibe’. An actual investment thesis.

If I'm taking profits from Google and I don't have a new conviction play, the money goes into SPMO or QQQM. That's where it was heading eventually anyway.

The mistake I see over and over?

Someone is up big on an individual stock, they sell all of it and put the whole thing into another single stock they think is going to the moon.

Except that new stock goes sideways. Then they panic, pull their money out and try and pick another one.

Then that one might do well for a little then start to tank.

They repeat this process over and over again. Each time losing a bit (or a lot) more money.

Remember the definition of insanity?

“Doing something over and over again and expecting a different result.”

That's not investing. That's trading.

I want to be direct about something.

Contrary to what people online will have you think, study after study shows the same thing: the overwhelming majority of traders lose money.

Not ‘some’ traders. Not ‘bad’ traders. Traders, as a category.

The ‘people’ on the other side of the successful trades you hear about?

They’re institutions with algorithms, decades of data, and zero emotion.

You trying to outperform them consistently, year after year, in my opinion is not a strategy. It's a bet with terrible odds.

If you want to hold a portion of your portfolio in individual stocks you believe in, fine. I hold 5-6 in my own portfolio.

In all honesty, I think it can be a smart growth move, especially if you’re young and have a long runway ahead of you.

And sure, some people get lucky.

They pick a stock or couple of stocks (like $35 Sandisk) and think “I’m a genius”. “I’m better at this than everyone else”.

Next thing they know they’re eating a big ole’ piece of humble pie when the subsequent 2-3 stocks they pick do the complete opposite and tank. Eating up all those gains they just got done bragging about.

Before you buy any individual position, ask yourself:

“Do I genuinely believe this company is going to beat X number, over my investing horizon, for a reason I can defend out loud?”

If the answer is yes, buy it.

If the answer is "I think it might go up," put the money in the S&P or total U.S. stock market. You have a literal 100% guarantee that money is going to go up and to the right over 20 years.

That's the opportunity cost.

Keep it as your North Star when you’re thinking about where to put profits.

Pick one individual stock in your portfolio and run the comparison.

Look up what day you purchased it. Then check what VOO, SPMO or VTI returned from that same date to today.

Finally, look at what your stock returned.

No judgment either way. Just know the number.

That's what investing from a place of awareness looks like.

If this clicked, forward it to someone sitting on big gains with no plan for them. This might be exactly what they need.

Your wealth hype girl,

-Charlie

📌 P.S. If you haven’t seen the emails, enrollment for the next Quiet Wealth Academy ends tomorrow, May 19th. This is my signature, live, 4-week small group investing program to help get you unstuck and actually on a path to achieve your financial independence faster.

If you’ve been waiting for someone to hold your hand through the whole investing process and get you started on the right foot, or help you find fees and other hidden costs that would be costing you $1,000s, keep an eye on your inbox. I only open it to 30 people.

🏦 How to build massive wealth by (legally) lowering your taxes — this book was my Bible when it came to learning the latest tax reforms and strategies to maximize tax savings and work towards my goal of an (almost) tax-free life.

📊 Here’s the inflation breakdown for April 2026 in one chart — due to the ongoing Iran war, it may be awhile until things stabilize. This breaks it all down by category so you can see what you’re actually paying the most for.

🎥 What $100/month will get you in 30 years — in this video, I break down the real numbers behind investing just $100/month, and show you how small, consistent growth can turn into serious wealth over time. If you’ve ever felt like you don’t have ‘enough’ money to start, this just might change your life.

🐷 On the farm: Our barn got concrete! This weekend we’re buying the lumber needed to start building out the horse stalls and pig pens, as well as the wash stall and tack/feed room. The only downside? Wiping concrete dust off the dogs’ feet 5X/day. 🤪

📈 On the market: One of my favorite finance YouTubers, Professor G, just did a video calling this the missing piece to the 3-fund portfolio. Watch this and consider adding it for even faster growth.

📬 From my inbox: A subscriber was confused on which 3 ETFs to put in her portfolio, and she pointed out, “you say something different in your video vs. email”. And that’s true, but it’s for a reason. I try my best to change up the investments I think people should look into and research on their own so they have options. If I only ever talked about VOO or VTI for example, people may think those are the only S&P 500 and total U.S. stock market funds out there. Personal finance is personal, and a fund that works for me, may not work as well for you. As they say, variety is the spice of life!

You can’t change what you don’t acknowledge.

If your way of tracking your investments looks like my brother’s room growing up, it’s time to get your s$%^ together my friend!

My Stock Tracker & Portfolio Balancer does exactly that.

It's a simple Google Sheet, fully customizable, and it costs less than 2 cups of ☕️.

Once you’ve got everything in one place, ask yourself: is my most tax-inefficient investment sitting in my most tax-protected account?

If not — you've just found some hidden money!

That's it. 20 minutes. Could be worth $1,000s over the next decade.

If you want to sit down together and map out your specific asset location strategy — which investments go where based on your exact accounts, income, and tax situation — that's exactly what my 1:1 private strategy sessions are for.

No pressure, no pitch. Just your numbers and a clear plan.

Disclaimer: this content is for educational and informational purposes only, and is not legal, financial or investment advice. Always do your own research before investing, and consult a licensed professional. Charlie and OJD LLC are not responsible for any losses or decisions made based on this content.