Trading Regrets: The Three Every Trader Lives With

In the stock market, you will always have three regrets:

"Why didn't I buy?"
"Why did I sell?"
"Why didn't I sell?"

That is the whole game, compressed into three questions. You cannot escape them. No strategy removes them, no indicator prevents them, and no amount of experience makes them stop hurting.

I have felt all three many times. But one stock gave me all three regrets in a single trade — and taught me more than any book I have read. This is that story.

Regret 1: "Why didn't I sell?"

In November 2024 I bought Netweb Technologies at around ₹2,800. The reason was clean: an ascending triangle had formed, price broke out, and the setup was textbook. I took a good position size because I had conviction in the chart.

The ascending triangle breakout that got me into the trade around ₹2,800.

The stock moved quickly. Within a short time it crossed ₹3,000. I was sitting on a clean profit.

And I did nothing.

My thinking was simple — the AI theme was strong, the momentum was strong, and I had a target of ₹3,500 in my head. Why book at ₹3,000 when ₹3,500 was coming? Booking felt like leaving money on the table.

Then DeepSeek happened.

An AI app nobody in my watchlist had been talking about suddenly rewrote the market's assumptions about AI infrastructure spending. Every AI-linked stock was sold like there was no tomorrow. Netweb fell from ₹3,000 to around ₹1,400 within roughly a month. Close to a 50% fall.

And the worst part was not the fall. The worst part was that the chart had warned me. The stock broke below its trendline on the way down. I saw it. I did not act on it.

The trendline break marked on the chart — the exit signal I saw and ignored.

That is the first regret in its purest form. Not "I lost money" — but "I was given an exit and I refused to take it."

It was a nightmare. Every time I opened my holdings, that one line stared back at me.

What I did next — and why I am not recommending it

I had two choices. Book the loss and move on, or average down.

I chose to average. My reasoning was that the fundamentals of the business were genuinely good, and that the fall was driven by a sentiment shock to an entire theme rather than by anything wrong with the company. I added at lower levels and brought my average price from ₹2,800 down to around ₹2,300.

Even after averaging, I was still sitting on roughly a 30% loss.

Then came the hardest part of the whole trade: nothing happened. The stock consolidated between ₹1,400 and ₹1,700 for about five months. No crash, no recovery. Just five months of an open loss sitting in my portfolio doing nothing.

I want to be honest here, because this is the part most people leave out of their trading stories.

Averaging down worked for me in this trade. It is not something I would tell a beginner to do. It worked because the business was sound and because I could afford to hold for five months without needing the capital. If the fall had been company-specific rather than theme-wide — a governance problem, a collapse in orders — I would have been adding money to something that never came back. Many traders have destroyed accounts doing exactly what I did here and getting a different outcome.

The technique did not make this trade work. The circumstances did. That distinction matters.

The recovery

Eventually the stock started moving. Price climbed to around ₹2,000. Then it consolidated again. Then another leg up, and finally it reached my buying price.

Then results came out — and they were outstanding. Within about two weeks the stock rallied all the way back to ₹3,000.

Five months of consolidation between ₹1,400 and ₹1,700, then the move back to ₹3,000.

I booked. Completely. Around 700 points of profit on a good position size.

After everything — the 50% drawdown, the averaging, the five months of waiting — I had turned a nightmare into a solid, real, realised profit. I should have been delighted.

Regret 2: "Why did I sell?"

The stock went to ₹4,500.

My exit marked at ₹3,000 — and everything that happened after it.

Almost 100% more, after I exited.

I could not control it. More than enjoying a profit I had genuinely earned — a profit I had waited months and held my nerve for — I sat there watching a number climb and feeling sick.

Think about how irrational that is. I made money. A lot of it. The trade was, by any objective measure, a success recovered from a disaster. And I was not happy at all.

That is regret number two, and it is the one nobody warns you about. The first regret at least teaches you something. This one just punishes you for winning.

Regret 3: "Why didn't I buy?"

The third is the one every trader knows from their watchlist. The stock you analysed, marked, and then skipped — for no good reason, or for a very good reason that turned out not to matter.

This one is dangerous in a specific way. It is the regret that creates FOMO. You miss one breakout, and on the next one you enter late, without a plan, at a worse price, with a stop you have not thought about. The regret of missing does not just feel bad. It actively makes your next trade worse.

The trap: how one regret creates the next

Here is the pattern I eventually noticed in myself, and it is the real lesson of this article.

The regret	What it makes you do next	What that causes
"Why didn't I sell?"	Book too early on the next trade	You cut your winners short
"Why did I sell?"	Hold too long on the next trade	You give back open profits
"Why didn't I buy?"	Chase the next breakout	You enter late without a plan

Every regret pushes you to overcorrect on the next trade. That is how one bad feeling turns into a losing streak. The loss is not caused by the market. It is caused by you trading the last trade instead of this one.

Why regret is unavoidable

You only ever see one outcome. You sold, so you never find out what holding would have felt like day by day — you only see the final number on the screen. Your imagination fills in the path you did not take, and imagination is always generous. The road not taken is always smooth in your head.

This is why regret cannot be solved by being a better trader. A better trader has the same information problem. They just handle the feeling differently.

The rule that keeps me sane: "Jo book kiya hai wo apna hai, baaki sab sapna hai."

What you have booked is yours. Everything else is a dream.

An unrealised profit is not money. It is a number on a screen that the market can take back whenever it wants — and in the Netweb trade, it took back 50% in a month. The only profit that has ever actually belonged to me is the profit I booked.

That line does not stop the regret. Nothing stops the regret. But it reminds me which of the two numbers is real.

What actually helps

• Judge the decision, not the outcome. Booking at ₹3,000 after a five-month recovery was a good decision. The stock going to ₹4,500 afterwards does not make it a bad one. A good process can produce a result you dislike, and a bad process can get lucky. If you judge yourself only by outcomes, you will learn the wrong lessons in both directions.
• Write the exit before the entry. If your target and your stop are written down before you buy, the decision to sell is made by the person who was calm, not the person who is watching a candle.
• Book partially. This is the practical answer to both the first and second regrets. Take some off the table at your first target and let the rest run. You will never catch the exact top, and partial booking means you are never fully wrong either way.
• Respect the trendline break. Netweb warned me before it fell. If you have a technical exit signal and you override it because you like the story, you do not really have a system — you have a hope.
• Stop tracking what you sold. Once the profit is booked, the stock is no longer yours. Watching it afterwards serves no purpose except to hurt.

Accept it and move on

The key is not to eliminate regret. It is to accept that regret is part of the game.

Every trader who has ever made money has also sold too early, held too long, and watched something they skipped double without them. The difference between traders who last and traders who do not is not that one group avoids regret. It is that one group feels it, accepts it, and takes the next setup on its own merits.

I still feel it. I felt it watching Netweb go to ₹4,500 with my money already in the bank. But I booked what was mine, and the rest was always a dream.

Frequently asked questions

How do I stop regretting trades?

You do not stop it entirely. What helps is writing your target and stop loss before entering, so the decision belongs to your planning self rather than your emotional self, and judging your trades by whether you followed your process rather than by the outcome.

Should I average down on a losing stock?

Very carefully, and rarely. It works only when the fall is driven by broad sentiment rather than something wrong with the business, and only if you can afford to hold for a long time without needing that capital. Many accounts have been wiped out averaging into stocks that never recovered. For most traders, taking the planned loss is the safer discipline.

Is it better to book profit early or hold for a bigger target?

Partial booking addresses both. Take some profit at your first target and let the remainder run with a trailing stop. You will not catch the exact top, but you also will not watch an entire gain disappear.

Why do I feel bad even after making a profit?

Because you compare your result to the best possible outcome rather than to your starting point. The path you did not take always looks better in hindsight, since you never had to live through its drawdowns. A booked profit is a success regardless of what the stock did afterwards.

Where to go next

• My Trading Journey — the longer version, including the expensive years
• Why Only 5% of Traders Succeed — why psychology beats strategy
• Ascending Triangle Pattern — the setup that got me into this trade
• How to Draw Trendlines Correctly — the signal I ignored on the way down
• Stock Market Basics for Beginners — position sizing and risk management

About the author

Written by Jithesh Shetty — software engineer and active trader in Indian equity markets since 2006. He trades intraday and swing setups on NSE and BSE stocks and writes about what actually worked, including the parts that did not. Read his trading journey or more about this blog.

Disclaimer: This article describes my personal trading experience and is for educational purposes only. It is not investment advice and not a recommendation to buy or sell any security, including any stock named above. Trading and investing in equities carries substantial risk of loss. Averaging down into a falling stock can result in significantly larger losses. Please consult a SEBI-registered investment adviser before making financial decisions. See our full disclaimer.