How long should you hold index funds before selling?

As long as possible. After eight years of holding without selling a single share, my unrealized gains grew to $130K. The hardest part isn't picking the right fund — it's resisting the urge to sell when you're in the green.

What should I do when the stock market crashes?

Keep your automatic contributions running and don't touch anything. During the COVID crash, I was down $2,000-$5,000 but kept buying — and those discounted shares became some of my most profitable purchases when the market recovered.

Why is it harder to hold when your investments are up?

Because unrealized gains feel like free money you could lose at any moment. At $13K in gains, the urge to cash out was almost physical — way stronger than the anxiety during actual market crashes. But selling means you'd need the courage to reinvest a lump sum, which most people don't have.

I Haven't Sold a Single Index Fund Since 2018. My Unrealized Gains Hit $130K

$130K in Unrealized Gains. But What I Remember Most Is Wanting to Sell at $13K

I started dollar-cost averaging into a total US stock index fund in 2018. About $1,000 a month. It’s been eight years now.

I haven’t sold a single share. Not once. Not when COVID crashed everything and I was staring at $2,000–$5,000 in unrealized losses. Not when my gains hit $13,000 and every cell in my body screamed “take the money.” Not when Trump’s tariffs wiped $50K from my portfolio and I still chose to do nothing. I haven’t even touched the settings on my automatic contributions.

The result? About $130,000 in unrealized gains.

I know. Sounds almost fake. But here’s the thing — I didn’t do anything special. I just never pressed the sell button. That’s all. And somehow, that was the hardest part.

The Early Days Were Pure Anxiety

I’ve written about those early months before, but let me be a little more honest about how I actually felt: terrified.

$1,000 a month. $12,000 a year. Getting sucked into a fund I barely understood.

The first few months, my balance barely moved. Sometimes it went down. I’d put in a thousand bucks and watch my balance go up by nine hundred. A savings account wouldn’t do that to you. At least with cash, the number doesn’t shrink. And here I was, voluntarily feeding a thousand dollars a month into… what, exactly?

“Is this actually going to grow?”

I was full of anxiety. That’s the only way to describe it. A vague but undeniable unease that showed up every time the next contribution date approached.

But I didn’t stop. I’d blown it with individual stocks before, and I knew — deep in my bones — that trusting a system was better than trusting my own instincts.

COVID Hit and My Resolve Wobbled

2020. The COVID crash.

I opened my brokerage account and saw unrealized losses of maybe $2,000 to $5,000. I don’t remember the exact number. Or maybe I’m choosing not to remember.

“Is this going to be okay?”

That one thought just kept cycling through my head. The news was screaming “historic crash” every single day, and nobody knew where the bottom was. Should I pause my contributions? Should I sell everything and buy back in at the bottom?

But then a moment of clarity hit.

Dollar-cost averaging means you keep buying when prices are low. If the market’s down, that same $1,000 buys more shares. You’re getting a discount. Selling now would be like walking out of a clearance sale empty-handed.

The COVID dip turned out to be shorter than anyone expected. When my portfolio swung back to green a few months later, one thought rang through my head: thank god I didn’t sell.

A person standing before a calm sea

The Scariest Moment Wasn’t the Crash — It Was the Gains

Here’s something that might surprise you.

The moment I wanted to sell the most during these eight years wasn’t during the COVID crash. It was when my unrealized gains crossed $13,000.

I wanted to sell so bad.

If you’ve never invested, this might not make sense. But sitting on $13,000 of “free money” is psychologically brutal. That’s a family vacation. A new laptop. Something nice for my daughter. There’s a $13,000 bonus dangling right in front of you, and you’re choosing not to grab it.

When you’re in the red, things are weirdly simple. You can’t sell at a loss (well, you can, but it feels wrong), so you just wait. No decisions to make. But when you’re in the green, your brain splits in two: “sell now and lock in the profit” starts fistfighting with “hold and it might grow more.”

People say selling winners is the hardest part of investing. They’re right. It’s a specific kind of suffering that you only understand once you’ve been there.

The Embarrassingly Simple Reason I Didn’t Sell

So why didn’t I sell at $13,000?

Iron discipline? Unshakeable faith in long-term investing? Nah. The reason was way simpler and way more embarrassing.

Say I sold and $20,000 landed back in my bank account. Then what?

Would I have the guts to dump that $20,000 back into index funds in one shot?

No. Absolutely not.

Monthly contributions of $1,000? That I can do on autopilot. But taking $20,000 in cash and clicking “buy” all at once? I don’t have that kind of nerve. Taking a position I’d built up over months and months of patient contributions, blowing it up with one click, and then starting the slow climb all over again from zero?

No thanks.

So I didn’t sell. Not because I was disciplined — because I was scared. Not exactly inspiring, right? But in investing, the unglamorous choice often turns out to be the right one.

An empty road stretching toward the horizon

The One Rule: Never Touch the Settings

There’s another reason I survived eight years without selling.

I decided from the start that I wouldn’t trust my own judgment.

My past mistakes taught me that whenever I tried to think my way through investing, things went wrong. So when I started index funds, I made one rule: never touch the settings. No matter what.

News says a crash is coming? Ignore it. Social media says it’s time to take profits? Ignore it. I check my brokerage account every morning, but I never touch the buy or sell buttons. The system runs itself. Same day every month, same amount gets debited, same fund gets purchased.

Over eight years, I’ve heard every kind of market prediction. “Shift to cash.” “Rotate into this sector.” “Get out before the crash.” I ignored all of it. I never panic-bought extra shares either. Just steady. Painfully, boringly steady.

Boring? Yeah. But boring built $130K.

The View From Eight Years Later

I wish I could show present-day numbers to the version of me who was screaming “sell!” at $13,000.

$130,000. Ten times what I almost cashed out for.

If I’d sold back then, I would’ve pocketed $13,000 and thrown away $117,000. A nice dinner in exchange for a down payment on freedom.

I’ll be honest: even at $130K, the urge to sell isn’t zero. I’m human. The bigger the number gets, the louder the voice that says “lock it in, retreat to safety.” As I wrote in ¥50 Million and Still Anxious, reaching a milestone doesn’t make the anxiety disappear — it just changes shape. There might be a day when $130K drops to $100K. A day when $30,000 evaporates overnight.

But I know something now that I didn’t know before. If I sell, I’ll never get back to the same place. And as long as I keep letting the system run, time does the heavy lifting for me.

A Message to My 2018 Self

If I could say something to the guy who started all this eight years ago — the same way I’d talk to my younger self about investing in general — it’d be two things.

The importance of holding. And the importance of trusting the system instead of your own brain.

These are things only someone who spent eight years doing nothing can say. And in a weird way, eight years of doing nothing earned me the right to say them.

The hardest part of investing isn’t picking the right fund. It isn’t timing the market.

It’s not selling. That’s it.

A man sitting on a bench, deep in thought

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