I Hit $350K in Assets and Still Couldn't Sleep Easy | The Trap of 'How Much Is Enough?'

The Day I Screenshotted My Brokerage Account

One day in 2025, I opened my Rakuten Securities app and saw that my total assets had crossed ¥50 million — roughly $350,000.

I fist-pumped. For real. It had been about eight years since I started investing seriously. I got into investing after a career setback, and my first goal was to surpass the ¥30 million I owed on my mortgage. Once my assets exceeded my debt, I’d be “net positive.” That milestone came and went, and eventually I found myself at ¥50 million.

I took a screenshot and saved it to my phone. Not to show anyone — just for me.

And then, maybe three seconds later, my brain went: “Please don’t drop below this number.”

Joy and fear, arriving at the exact same time. The moment I reached the milestone, the fear of losing it kicked in. The version of me who started investing eight years ago would never have predicted that.

Then Trump’s Tariff Shock Hit

I barely had time to celebrate before President Trump’s tariff announcements sent markets tumbling.

My portfolio dropped below ¥50 million almost immediately.

“I literally JUST got there!” was all I could think. But I didn’t change a single thing about my investment strategy. That’s my one unbreakable rule, regardless of the number in my account: keep contributing, don’t sell, don’t try to time the market.

Was I disappointed? Sure. But I also figured it would recover eventually. Nobody can actually guarantee that, of course. But when you choose index investing, you sign up for this kind of ride. I felt restless, but I wasn’t rattled. There’s a meaningful difference between those two things.

The Trap of “How Much Is Enough?”

When I first started investing, my goal was simple: get my assets above my ¥30 million mortgage balance. Once my net worth was positive, I’d feel secure. That was the plan.

I crossed ¥30 million. Okay, that felt pretty good. But then my brain automatically moved the goalposts: “¥50 million — THAT’s the real number. Once I hit that, I’ll really feel safe.”

Well, I hit ¥50 million. And I don’t feel safe at all.

I’m pretty sure if I hit ¥100 million (about $700K), I’d immediately start thinking “but ¥200 million would be so much better.” The human brain doesn’t resolve anxiety with account balances. That’s just not how it works.

Here’s the funny part, though: it doesn’t feel safe, but it still feels good when the number goes up. I’m fully aware of the contradiction. No peace of mind, but genuine happiness when assets grow. If you invest, I think you probably know exactly what I mean.

Index Fund Numbers Feel Like an Illusion

There’s another reason the anxiety doesn’t go away. The volatility of stock-based assets — especially index funds — is just brutal on your psyche.

If I owned a $350K rental property generating steady monthly income, I think I’d feel much calmer. The number on the screen wouldn’t swing around. But with index funds, your portfolio can move $3,000-$7,000 in a single day. ¥50 million last month, ¥47 million this month. Totally normal.

So unrealized gains start to feel like… not quite real. Like a number in a video game. You haven’t sold, so it’s not profit. You haven’t sold, so it’s not a loss either. Schrödinger’s portfolio, if you will.

This “can I really call fluctuating numbers an asset?” problem is something that probably never fully goes away as long as you keep investing.

$350K in Assets and Nobody to Talk To

Here’s something that’s surprisingly hard about having a decent-sized portfolio: you can’t tell anyone about it.

I don’t talk about my asset balance with coworkers or friends. Ever. Years ago, a boss of mine used to talk about his investments and net worth constantly. As the listener, I felt exactly zero positive emotions. It was just “cool story, bro — so are you buying dinner tonight or what?” This is part of why I check my portfolio alone at 4 AM — it’s the only time I can process these feelings.

That experience taught me to keep my mouth shut. Money talk creates problems. If a junior colleague sincerely asks me about investing, I’ll help. But I never bring it up myself.

My wife knows the rough numbers, but when I told her I’d crossed ¥50 million, her response was essentially “oh, nice.” We have different temperature settings when it comes to money enthusiasm. That’s fine, really — but it means the excitement and the anxiety of investing are things I process alone.

Honestly? This blog is my outlet. The things I can’t say to anyone in real life, I write here. If you’re reading this, that alone means a lot to me.

Making Peace with Permanent Anxiety

After writing all this doom and gloom about never-ending anxiety, I should mention: I’ve actually reached a kind of acceptance recently.

The anxiety won’t disappear. No dollar amount will make it go away. I’ve accepted that as a baseline truth.

So the real skill isn’t eliminating anxiety — it’s refusing to let it control your behavior. Feel restless, but don’t panic. Watch the market drop, but don’t stop contributing. See your unrealized gains shrink, but don’t sell.

After eight years of index investing, I’ve finally internalized this: emotional control is the single most important investing skill. Not technical analysis. Not stock picking. Just the ability to observe your own emotions and not let them drive your decisions. It’s unglamorous, but it’s everything. That’s exactly why I stopped trusting my own judgment and automated the whole process.

Will FIRE Make the Anxiety Disappear?

I do have FIRE as a goal, for the record. But honestly, I suspect that even after reaching financial independence, the anxiety won’t hit zero. If I quit my job, a new fear will be waiting: “Is it really okay to draw down my assets with no income coming in?”

The shape of the anxiety changes, that’s all. As a salaryman: “Is this salary enough?” After building wealth: “What if I lose it all?” After FIRE: “Can I really sustain this withdrawal rate?”

Maybe that’s just fine. A life with zero anxiety probably doesn’t exist.

So What’s the Point of Investing Then?

If you’ve read this far, you might be thinking: “If the anxiety never goes away, what’s even the point?”

Here’s what I’d say: the anxiety doesn’t go away, but the joy absolutely grows. The happiness I felt screenshotting that ¥50 million balance was real. Watching the line on my portfolio graph trend upward over eight years — that thrill hasn’t faded.

And more importantly, my options in life have expanded. Knowing I could quit my job tomorrow and survive for years — that’s a kind of psychological freedom you can’t put a price on. When my daughter needs something for her education, I don’t have to hesitate. When work gets unreasonable, I can think “worst case, I walk away” — and actually mean it.

The anxiety doesn’t go away. But compared to the version of me before I started investing, I’m holding a lot more cards.

If you can make peace with living alongside the anxiety, that’s enough. At the very least, I can tell my past self with full confidence: “The anxiety never goes away — but you’ll be glad you started.”

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