The Day I Hit Sell on a $14,000 Loss — My Hands Were Shaking

The Numbers on My Screen Turned Red Every Day

This happened when I was still brand new to investing.

I bought shares in a telecom company. And not just a small position — I put almost all my available cash into it. Looking back, that was insane. But at the time, I just wanted to make a lot of money, fast. That’s all it was. I was acting on pure greed. You could dress it up with fancy words like “concentrated investing,” but that’s not what it was. I wanted to get rich quick. Plain and simple greed.

The stock started dropping the moment I bought it.

Every time I opened my brokerage account, red numbers hit me in the face. Minus ¥300,000. Minus ¥500,000. Minus ¥1 million. Eventually, the loss ballooned to ¥2 million — roughly $14,000.

The “it’ll bounce back soon” phase had long since passed.

I kept checking the price because I wanted reassurance. First thing in the morning on my phone. Again during lunch at the office. Again on the train ride home. “Please let it have recovered a little,” I’d think as I opened the app. But the more I checked, the more anxious I got. And yet I couldn’t stop. Not checking felt even worse. Looking back, it was borderline compulsive. (I still check my portfolio every morning at 4 AM, but the feeling is completely different now.)

“I Just Want This to Be Over”

The reason I decided to cut my losses wasn’t some rational, calculated decision.

“I just want this to be over.”

That was literally it.

I’d poured most of my funds into that one stock, which meant I couldn’t trade anything else while it sat there bleeding. There was no guarantee it would recover. It could keep dropping.

But more than anything, I simply couldn’t take seeing those red numbers every single day anymore.

At night, lying in bed, the thoughts wouldn’t stop. Should I just accept this loss? Maybe it’ll bounce back if I wait a little longer. But what if it keeps dropping? Questions with no answers, spinning in circles in my head.

In the end, I let my emotions take the wheel. It wasn’t a cool-headed investment call — it was pure desperation to escape the pain. I hit the sell button.

My hands were shaking.

The moment I pressed it, what hit me first was relief. “It’s finally over.” I felt a weight lift. The loss hurt, but at least that daily suffering was over.

But almost immediately, another thought crept in: “What if the stock goes up after this?” The idea of watching it climb after I’d sold — I couldn’t face that. I didn’t want to look at the market anymore. Looking back, I completely lacked the ability to think long-term.

Why That Particular Stock?

So why a telecom stock, of all things?

It was a smaller company that offered budget SIM cards and internet provider services. The major carriers like NTT Docomo and KDDI were already trading at high prices. I deliberately avoided those and picked a smaller company that I thought had more room to grow.

I even analyzed the P/E and P/B ratios before buying. I’d built what I thought was a solid thesis.

None of it mattered.

No matter how much knowledge you have, no matter how thorough your analysis, the market moves however it wants to move. The scenario I’d constructed in my head — “it should go like this” — was completely useless. I learned the hard way, to the tune of $14,000, that knowledge and real-world experience are two entirely different things.

A Level 5 Character in a Level 50 Dungeon

If this were an RPG, I was a Level 5 character who’d wandered into a Level 50 dungeon.

Concentrated bets on individual stocks? Even professionals blow up doing that. A complete beginner throwing almost everything into a single ticker had no business expecting to win. I may have had some knowledge. I knew what P/E and P/B ratios were. But knowledge and experience are entirely different things. Just like reading a textbook doesn’t make you capable of performing surgery, the ability to stay calm in volatile markets can only come from experience.

If I’d lost even more, I honestly can’t imagine what would have happened to me. In a way, maybe I was lucky it was “only” ¥2 million. In hindsight, if I’d held on for another year or two, the stock would have recovered. But staying invested while deep in the red, unable to do anything else with my money, for an unknown period of time — I didn’t have the mental fortitude for that. Not back then.

I Walked Away from Investing for Five Years

After cutting my losses, what I did was… nothing.

I didn’t try to win it back. I couldn’t — there was no basis to believe I could. I’d thought it through, analyzed the numbers, made my pick, and lost. The idea of doing the exact same thing again and expecting to win? That just didn’t compute.

Besides, I genuinely hated losing money. I just wanted to stop.

Deep down, I think I already knew. Short-term gains weren’t the right path. Steady, long-term growth was the real answer. But at the time, I didn’t have the mental bandwidth to make that switch.

I walked away from the investing world entirely. For about five years.

I didn’t delete the brokerage app from my phone, but I barely opened it anymore. I just couldn’t bring myself to look. My savings grew naturally during that time — maybe because I wasn’t throwing money at stocks, I spent less on unnecessary things. Honestly, I just didn’t want to think about investing at all.

During those years, I cooled off. I came to terms with the fact that I was playing way above my level.

Five years later, I started buying high-dividend stocks. Small amounts, spread across multiple names this time. Instead of going all-in on one ticker, I split my money across several, keeping each position small. That alone made an enormous difference for my mental state.

Then I discovered NISA and iDeCo (Japan’s tax-advantaged investment accounts), which led me to index fund investing. That transition — from panic-selling individual stocks to learning to stop thinking and love index funds — was the real turning point.

From a ¥2 million loss to index investing — it took me over five years to get there. The long way around. But without those five years, I don’t think I would’ve been able to accept the “boringness” of index investing. As I wrote in The First 3 Years Were Boring, getting burned on flashy individual stock picks is exactly what made the quiet, steady rhythm of index fund contributions feel just right.

”It Was a Good Learning Experience” Is Just Something We Tell Ourselves

People who take big losses in the market often say things like:

“It was tuition for the school of hard knocks.” “A valuable learning experience.”

I want to believe that too. I really do.

But honestly? It doesn’t feel that way at all.

I still remember the pain of that loss. I still have regrets. ¥2 million — how many family vacations was that? How many experiences with my kid? What could I have bought for my daughter? I think about it sometimes.

“Tuition” is just a word people use to comfort themselves about past mistakes. If I actually wanted to learn about investing, I could have read ten books instead of losing $14,000. The public library is free.

I Decided to Stop Trusting My Own Judgment

The biggest lesson that failure taught me: stop trusting your own judgment and emotions.

Index funds have historically gone up over time. Meanwhile, the value of cash worldwide has been steadily declining. I aligned myself with these facts. Instead of relying on my own analysis or predictions, I decided to ride the wave that history has already proven.

Monthly contributions are fully automated. I removed any space for my emotions to interfere. Whether the market goes up or down, the contributions execute mechanically. Back when I trusted my own analysis, I lost ¥2 million. That’s exactly why I now trust the system over my own judgment. When Trump’s tariffs later wiped $50K from my portfolio, I didn’t flinch — because the system was doing the thinking for me. Since switching to this approach, my investment-related stress has dropped dramatically.

My Current Investing Style Is Built on That ¥2 Million

My investing these days is boring by design.

I contribute a fixed amount to index funds automatically every month. When markets crash, I keep contributing. Steadily. I haven’t sold a single share since 2018, and the unrealized gains keep compounding. I still check my brokerage account every day — I enjoy looking at it. But I never change anything based on what I see. Back then, checking the price made me more anxious every time. Now I look at the numbers and just think, “The system is running.” Same daily habit, completely different meaning.

Back then, my Level 5 character got wiped out in a Level 50 dungeon. That’s exactly why today, I’m grinding experience points in a zone that actually matches my level.

The ¥2 million loss wasn’t a “good experience.” It still hurts.

But because of that pain, I have zero hesitation about my current approach: trust the system over my own predictions. Having lost ¥2 million by overestimating my own analysis, I now let history and structure do the work.

If you’re reading this and you’ve just taken a big loss on individual stocks — I want to say one thing.

Don’t try to win it back by force. If you don’t have a solid reason to believe you can recover it, it’s okay to walk away for a while. During that time away, you’ll learn where your real level is. And when you eventually come back, you’ll make smarter choices than before.

At least, that’s how it worked for me.

This article reflects personal experience and is for informational purposes only — not investment advice. All investment decisions are your own responsibility.