Trading is a game of decisions.

When it comes to playing the markets, you’ll have split seconds where your courage and discipline are tested.

But sometimes, the real pain comes not from the trades you take, but the ones you don’t.

I’ve spent years learning this the hard way.

March 2020 was a prime example. Markets were in freefall, panic was everywhere, and opportunities were quietly emerging beneath the chaos. I had cash. I had a plan. I even had a list of stocks ready to buy.

But a couple of small, seemingly harmless mistakes — decisions that most people would make and ones that felt cautious at the time — ended up costing me more than I care to admit. In fact, if I’d acted differently, the gains could have totaled seven figures.

It’s hard to forget moments like this. It’s even harder to face them head-on. But as painful as those lessons are, they’re also priceless.

Today, I’m walking you through two trades — two gut-wrenching missed opportunities I’ve analyzed again and again. I’ve learned from them. And I want you to have the same chance to learn these lessons.

Because when markets roar higher, the real risk isn’t losing money…

It’s not making enough.

And sometimes, you just have to shut out the fear and slam the “buy” button…

Before I get into the details, I should clarify that I’m not going to read you a list of random stocks that turned into huge winners and claim them as missed opportunities. After all, it’s downright impossible to buy every single breakout — especially during a raging bull market.

Even today, you have to stay choosy and accept that you won’t catch every single hot stock. But you also have to take those trades you might hesitate to grab during the less frothy months of the year. Keep this in mind as we continue!

The missed trades I’m going to detail today are exactly that — misplayed or unfilled trades that I was actively tracking or working with in real-time.

The Windfall That Wasn’t

I’ve written before about some of the similarities between current market conditions and the late stages of the pandemic bubble in Dec. 2020 – Jan. 2021.

Today, I want to turn the clock back a little more to the height of the Covid meltdown: March 2020.

By the time the market was in freefall, I had already sold out of my short-term trades and wielded a healthy cash stockpile. But as you’ll soon see, my mistakes during this turbulent era weren’t from taking too much risk. Instead, I failed to properly assess my risks and behaved too conservatively when I should have been “all in” on the winners I correctly identified.

My mistakes during March 2020 were twofold. First, I failed to take a big swing at longer-term plays out of a fear of them taking too long to reverse and turn higher. I also didn’t take large enough risks on emerging momentum winners and took profits too early as the market bottomed out and began to rally.

Altogether, I easily left a cool million (or more!) on the table.

Let’s take a look at the first scenario: the missed opportunity.

With plenty of cash to deploy in my longer-term account, I was ready to shop for bargains as the stock plummeted in March. As the averages became deeply oversold, I put in sizable orders for Apple Inc. (AAPL), Shopify Inc. (SHOP), and a couple of other excellent companies.

I planned on holding these names for months, well aware that they might not immediately recover from their sharp drawdowns. But I made a critical error: I placed limit orders for my trades at levels around 5-7% below where they were trading at the time.

The problem with this plan is that I placed these orders the week the market bottomed. The trades never triggered, and I walked away without a single share added to my portfolio.

At the time, it was easy to be overly cautious as we endured the fastest stock market crash in history. But hindsight reveals my major errors.

First, why limit orders? These were longer-term bets on quality stocks, so it shouldn’t have mattered if they didn’t recover right away. Also, I was being greedy (or unreasonable at the very least) attempting to get these shares for lower prices.

Also, remember that I put this order in the week the market bottomed. The market (and the stocks in question) began moving dramatically higher in the weeks ahead. I still failed to add these names to my portfolio as the averages recovered — another critical mistake that led to one of my biggest missed opportunities for a solid long-term entry point in several world-beating stocks.

Popping the Pandemic Bubble

My second trading mistake in March 2020 involved a trade where I was well ahead of the curve, yet failed to take the appropriate action to maximize my profits.

While the major averages were still in freefall, I identified several recent IPOs that were bottoming out and beginning to move higher. I added two of these stocks — Peloton Interactive Inc. (PTON) and Chewy Inc. (CHWY) as short-term trades.

You might remember what happened next…

These stocks began to accelerate higher. And as the broad market bottomed out and started to flash an oversold bounce into April, PTON and CHWY were building into strong trades.

But instead of doubling down or buying calls, I took my profits off the table. At the time, I was pleased to lock in double-digit gains in a damaged market. But we now know the better move would have been to hang onto at least partial positions in these stocks, which turned into some of the biggest winners of the subsequent pandemic bubble.

PTON rallied more than 700% from its Covid lows in just nine months. And I was able to trade PTON, CHWY, and the other pandemic wonders many, many times during the advance.

But by taking gains early on these trades, I lost the chance to develop core positions in two of the year’s best stocks.

Yes, some hindsight bias comes into play during this post-trade assessment. But keep in mind, I had no other reason to jettison these shares other than my fears of another market drop that never materialized.

It’s All About Risk

Overall, I estimate I left seven figures on the table due to the mistakes I made with these trades. Thankfully, 2020 was still an amazing trading year, full of opportunities to book impressive gains — and I was able to take full advantage of the frothy conditions.

To be clear, I don’t like to dwell on mistakes or missed trades. But reviewing how I executed my trading plans (or lack thereof) can greatly improve my future results. Since we’re now dealing with melt-up conditions in the current market, reviewing my mistakes from similar periods in the past will only help me make more money in the present.

While the two trading situations I outlined for you today are very different, they both involve failures in risk management.

The main lesson here is not about taking too much risk. Instead, I was misinterpreting my risk levels and acting too conservatively when I should have been aggressive. I should have just bought AAPL and SHOP with market orders since they were longer-term ideas that I already planned on holding for many months. And when the market started recovering, I should have adjusted and bought at even higher prices. My inaction cost me dearly…

With the PTON and CHWY trades, I should have taken partial profits instead, and let the remaining shares ride. But I acted out of fear and cashed out as soon as they were showing small gains.

Once again, letting my emotions interfere with my process caused me to act too conservatively at the wrong time.

That brings us back to the current market melt up.

As I’ve said for weeks, I’m more concerned about the trades I’m not involved with right now. In melt-up conditions, your biggest risk for traders is misplaying an explosive rally.

Sometimes, you just have to close your eyes and buy. Remember this lesson as the market continues to melt higher.