"亢龙有悔 (Arrogant Dragon Brings Remorse): Why It’s Easier to Lose Investment Gains Than to Earn Them"

How do you hedge investment risks? It’s a topic everyone talks about, but few really get to the bottom of it.

Have you ever met someone like this?

They grind like crazy when they’re young, clawing their way up from the bottom, going through hell and pulling off win after win. By their 40s or 50s, they’ve got money and fame—by all accounts, they’ve lived a full, successful life.

But they just can’t stop.

Their company keeps growing, their bank account keeps swelling, but they’re more exhausted than ever. You tell them to take a break, and they say they can’t—they just can’t slow down. Ask them why, and they can’t even put it into words. Maybe it’s habit. Maybe they’re scared they’ll fall behind the second they pause. Or maybe… they just think they can climb one rung higher.

And then what happens?

Then a lot of them crash and burn on that “one more rung.” Everything they built in the first half of their lives, they lose in one go in the second half.

Isn’t that such a waste?

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亢龙有悔 (Kàng Lóng Yǒu Huǐ): What exactly is the remorse about?

The top line of the Qian Hexagram (Nine at the Top) has a four-character Line Text: 亢龙有悔 (Arrogant Dragon Brings Remorse).

The dragon has flown too high, and now it’s full of regret.

These four characters are fascinating. It doesn’t say “the arrogant dragon meets misfortune” or “the arrogant dragon suffers disaster.” It says “有悔” — remorse, regret.

Why regret?

Because this isn’t a natural disaster—it’s a self-inflicted mess. No one did this to you; you chose it. You knew you were already at a great height, but you wanted to go higher. You knew it was time to pull back, but you couldn’t rein yourself in. Only when you come crashing down do you kick yourself: *If only I hadn’t been so greedy*.

But there’s no such thing as a regret pill in this world.

Look at those entrepreneurs who implode, those officials who get taken down, those people who lose everything on bad investments. How many of them failed because they started with nothing or had too few resources? Most failed because they were *too* successful—so successful they thought they could handle anything, that no risk was too big.

And then it all falls apart.

What Nine at the Top of the Qian Hexagram really describes is one of the most common pitfalls in investment risk: people who’ve already made money are the most likely to think they can beat the odds.

The character “亢” (kàng) means excess, extremity, being unable to stop. A dragon that’s flying perfectly well in the sky insists on pushing higher and higher. As it climbs, the air gets thinner, the winds get stronger, and soon it can’t even turn back.

That’s 亢龙有悔 (Arrogant Dragon Brings Remorse). It’s not that the sky is out to get you—it’s that you’re the one marching yourself off a cliff.

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Why do people get “亢” (arrogant/overextended)?

Why would anyone trade the steady glory of a Flying Dragon in the Heavens for the mess of an Arrogant Dragon?

I’ve thought about this a lot, and I think there are three main reasons.

First reason: path dependence.

Whatever method made someone successful, they’ll keep using it forever.

People who succeeded by overworking will keep overworking. People who succeeded by taking risks will keep taking risks. People who succeeded by schmoozing and networking will keep schmoozing and networking.

They never stop to question the method, because it worked every single time before. They just figure: *If I just push a little harder, I’ll reach the next level*.

But they forget: times change, circumstances change, *you* change. What worked before might not work now. The risks you could absorb back then, you might not be able to absorb now.

This is the most common trap in investing. You make a killing in one bull market, decide you’re a stock market genius, and do the exact same thing next cycle—only to lose every penny of your profits. It’s not that the market changed. It’s that you got stuck in path dependence.

When you were young, you had nothing to lose. If you failed, you could just start over. What about now? You’ve got kids and aging parents to support, and hundreds of employees counting on your company for a paycheck. Can you really afford to lose?

Too many people never do that math. They think they can still gamble, and then they lose it all in one hand.

Second reason: identity anxiety.

This might sound a little out there, but it’s the truth.

A lot of people have been “strivers” their whole lives. Their entire sense of self is built around “I’m a hard worker” or “I’m a successful person.” If they stop striving, stop being successful, they don’t know who they are anymore.

Tell them to retire, to take it easy, and they’ll feel miserable. They’ll think they’re useless, that society has left them behind. So they have to keep running forward—even if they’re exhausted, they have to keep going. Because if they stop, they lose themselves.

This isn’t greed—it’s fear. Fear of losing your identity, fear of being ordinary.

But here’s the thing: isn’t everyone ordinary? No matter how impressive you are, you’re still just a regular person.

Third reason: the people around you keep pushing you forward.

When you’re at the top, you’re surrounded by people. These people rely on you for their livelihood, for their own success. If you stop, what happens to them?

So they’ll keep hyping you up, painting grand pictures of the future, handing you new goals to chase. They’ll say, “Boss, you’re incredible—our next target is the Fortune 500!” They’ll say, “Big guy, you’re so talented, it’d be a shame to stop now!”

Hear that enough, and you start to believe it. You think, *Maybe they’re right. I can pull off one more big win*.

But have you ever stopped to think—if it all fails, who’s left holding the bag? *You* are. The people pushing you forward? They’ll just find another boss to leech off of.

That’s why, the more you’re surrounded by cheers and applause, the more you need to keep a clear head.

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How to avoid becoming an “Arrogant Dragon”

Easier said than done, right? Everyone knows when to call it quits in theory—but when you’re actually up there, no one wants to step down.

But not wanting to doesn’t change anything. Rules are rules. They exist whether you believe in them or not.

Let me give you three pieces of advice—see if they make sense.

First piece of advice: find the “ceiling” of your life.

Everyone has their own ceiling. This ceiling isn’t set by your ability—it’s set by your luck, the era you live in, and your personality, all mixed together.

You have to know where your ceiling is. That doesn’t mean you can’t do anything once you reach it—it means you don’t bash your head against it trying to break through. You’ll just hurt yourself for nothing.

How do you find it? Simple. When you’ve tried to climb higher several times in a row and can’t move an inch, when you realize the cost of going higher is more than what you’d gain—chances are, that’s your ceiling.

When you hit the top, don’t force it. Enjoy the view from up there. It’s way more meaningful than bashing your skull against a wall.

Second piece of advice: build a “loser’s mindset.”

What’s a loser’s mindset? It means before you make any decision, you first ask: what’s the worst-case scenario, and can I live with it?

Average people think, *How much will I make if this works out?* Smart people think, *How much will I have left if this fails?*

This isn’t pessimism—it’s clarity. It’s also the core rule of investment risk management: think about losses first, gains second.

Look at people who’ve had long, successful careers. Not a single one is a reckless gambler. They might look like they’re taking risks, but every step is calculated: *What’s the worst that can happen? Can I handle that?* If yes, they go for it. If no, they walk away.

Why does the Arrogant Dragon have remorse? Because before he flew up, he never thought about how he’d get back down. By the time he wants to come down, he can’t.

Third piece of advice: cultivate a “second identity” while you’re at your peak.

What’s a second identity? It’s who you are, outside of your current role.

For example: you’re an entrepreneur, but you’re also a parent, a spouse, a hobbyist photographer, a volunteer for a charity. All of those are your second identities.

The more of these identities you have, the less likely you are to get “亢” (overextended). Because even if your main career falls apart, you’ve got other things to do, other ways to feel valuable.

The scariest thing is when a person only has one identity their whole life. Strip away “boss” or “leader,” and they’re nothing. Of course they can’t stop—if they do, they lose everything.

So while you’re still at the top, pick up a few more hobbies, make some friends who have nothing to do with your job, spend more time with your family.

These things might seem useless day to day. But when it’s time for you to step down, they’re your parachute.

There’s a term in investing called “diversification.” Life works the same way—don’t bet all your worth on one single thing. Lay down a few extra paths. It never hurts.

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A few final thoughts

I know a senior guy, in his 60s, used to be the CEO of a huge company. After he retired, he spent every day fishing, doing calligraphy, and looking after his grandkid. He’s having the time of his life.

Someone once asked him, “You used to run such a big company—can you really stand being this idle?”

He said, “Why wouldn’t I? I was busy back then because I needed the job. Now I don’t need it—why would I still be busy?”

The person asked again, “Don’t you miss it at all?”

He said, “Miss what? The glory? The fanfare? Having people fawning over you everywhere you go? Honestly, it was great. But when the show’s over, you step off the stage. You can’t stay up there your whole life—there are so many people waiting in the wings. Besides, being in the audience is nice too. Watching other people put on a show is way easier than performing yourself.”

See? That’s a person who gets it.

Times change, and methods get simpler. But one thing never changes: climbing up is hard, but climbing down is harder. Climbing up takes skill. Climbing down takes wisdom.

亢龙有悔 (Arrogant Dragon Brings Remorse) doesn’t mean you can’t reach the highest point. It means once you get there, you have to know how to get back down.

Knowing when to advance is easy. Knowing when to retreat is hard.

Plenty of people can charge forward. Very few can step back when the time is right.

And the truly impressive ones? They’re always the latter.

Wen Laoshi often says that every one of the 64 Hexagrams of the I Ching is teaching you about “measure.” Cross that line, and even good things can turn bad. 亢龙有悔 (Arrogant Dragon Brings Remorse) from Nine at the Top of the Qian Hexagram is the perfect example.

So stop obsessing over going just a little higher.

Good enough is good enough.

The people who can climb back down are the ones who truly made it to the top.

And as for how to hedge investment risks? It boils down to one sentence: know where your ceiling is, step down when you reach it, and don’t overstay your welcome.