What You Should Do Most at the Peak of Life Is Not Keep Climbing Higher

A while back, an older buddy invited me out for dinner, and we got talking about the Nine in the Fifth Place of 乾為天 (The Creative) — 飛龍在天 (Flying Dragon in the Heavens). He said he’s right at that spot right now, and it’s making him anxious instead.

I call him an older buddy, but he’s not actually old — just in his early 40s. He’s in the internet industry; his company got acquired a few years back, so he’s got a pile of money and a solid reputation.

You’d think this would be the most triumphant time of his life.

But he told me he’s been really stressed lately.

I said, “You’re financially free and you’re still anxious? What’s that supposed to mean for the rest of us slaving away?”

He said it’s not about the money. Wherever he goes these days, everyone’s fawning over him — people hang on his every word, and every idea he has gets hyped up. But he’s feeling more and more unmoored. “I can’t tell if I’m actually that good,” he said, “or if everyone’s just going along with me because I’m rich and famous now.”

When I heard that, my respect for him went through the roof.

I said, “If you’re thinking that way, it means you haven’t let it go to your head. A lot of people in your position would already think they’re invincible.”

He gave a bitter smile. “That’s just because I’ve seen way too many people fall.”

What Does It Feel Like to Fly High in the Sky?

The Line Text for the Nine in the Fifth Place of 乾為天 (The Creative) reads: 飛龍在天 (Flying Dragon in the Heavens), 利見大人 (It Furthers to See the Great Person).

The Nine in the Fifth Place is the fifth Yao (Line) of 乾為天 (The Creative), and it’s the most auspicious line in the entire hexagram — the ancient term “the honor of the ninth five” comes right from this line. The dragon has soared into the sky, free and unbound, able to summon wind and rain. It stands tall, sees far, and can do whatever it pleases.

Applied to life, this is the point where your Career is thriving, your status is solid, and your influence is at its peak.

What’s it like to be in that state?

People listen when you speak. Offhand comments get jotted down immediately by the people below you, carried out like imperial edicts.
People help when you act. Whatever you want to do, resources, connections, money — they all flock to you on their own.
You feel like you can do anything. Things that used to feel impossible don’t seem hard anymore. People you could never win over before are now currying favor with you.

Is that feeling good? Of course it is. Who wouldn’t love that?

But here’s the problem — it feels so good that it’s easy to get carried away.

You start to think everything works out because you’re so talented. You forget that a lot of things succeed not because you’re amazing, but because your current position, the resources in your hands, and the platform behind you are holding you up.

Wait until the day you step down from that position, and try to do the same things again — you might not be able to pull them off.

That’s the trap of 飛龍在天 (Flying Dragon in the Heavens): the higher you fly, the harder it is to tell if you’re flying on your own, or if the wind is just carrying you.

The Nine in the Fifth Place of 乾為天 (The Creative) looks like it’s all glory and fanfare, but it hides the truth that things reverse when they reach their extreme. The seed of decline after prosperity is almost always planted at the very moment you feel most triumphant.

The Most Common Mistakes That Trip People Up at Their Peak

As the saying goes, things reverse when they reach their extreme; prosperity is followed by decline. Everyone knows this saying, but when it comes to their own lives, barely anyone truly believes it.

I’ve seen so many people fall from their peak.

The reasons they fall are all different, but when you boil it down, they all come down to the same few mistakes.

Thinking you’re invincible.

This is the most common one. When someone finds success in one field, they start to think they can succeed in every field.

They make it big in internet tech, so they jump into investing; they make money investing, so they move into brick-and-mortar businesses; when the physical business flops, they pivot to blockchain.

In the end, they lose their grip on their main business, and all their side ventures tank too.

That’s not to say you can’t cross into new fields — it’s just that when you do, you need a clear head: in a new field, you’re a beginner. The experience you had before won’t necessarily work there.

With 飛龍在天 (Flying Dragon in the Heavens), you’re flying in your own sky. Swap to a different sky, and you might not be able to take off.

Being unable to take opposing opinions.

When you stay up high for too long, your ears start to “pick and choose” what they hear.

After listening to too many nice things, you can’t stand to hear the hard stuff. When someone raises a disagreement, your first thought isn’t “does what they’re saying make sense?” — it’s “how dare they question me?”

Little by little, the people around you who tell the truth get fewer and fewer, and the bootlickers multiply. Everything you hear is what you want to hear; everything you see is what you want to see.

By the time you notice the problem, it’s already too late.

That’s why the ancients said 利見大人 (It Furthers to See the Great Person). Even when you’re a flying dragon in the heavens, you still need to “see the Great Person.” What kind of Great Person? People who dare to tell you the truth, people who are even more capable than you, people who are willing to throw cold water on your ego.

Only that way can you stay clear-headed.

Forgetting to leave yourself a way out.

A lot of people at their peak only ever look up, never down.

All they think about is: how do I climb another rung? How do I make more money? How do I get even more influence?

Hardly anyone stops to think: what if I fall? Do I have a way out? Can I land safely?

Look at all the entrepreneurs and officials who’ve gotten into trouble — how many of them were brought down by someone else? Most of them let success go to their heads and forgot to leave themselves an escape route. They charge full speed ahead, and by the time they reach the edge of the cliff, they realize they can’t hit the brakes.

乾為天 (The Creative) has six Yao (Lines) total. 飛龍在天 (Flying Dragon in the Heavens) is the fifth line. There’s still one line above it — 亢龍有悔 (Arrogant Dragon Brings Remorse).

What does that mean? It means no matter how high you fly, there’s always somewhere higher. But that higher place isn’t a good thing — it’s “remorse.”

That’s why smart people start preparing while they’re still flying high. Preparing for what? Preparing for how to come back down.

What Should You Do When You’re Standing Tall?

So what should you actually do when you’re at the 飛龍在天 (Flying Dragon in the Heavens) stage?

I think there are a few things that matter more than charging even higher.

First, guard your core foundation.

This is the most essential lesson of the Nine in the Fifth Place of 乾為天 (The Creative) — no matter how high you fly, your roots can’t be cut.

Whatever it was that got you where you are, hold onto it.

If you built your success on making great products, keep making great products; if you got famous from writing, keep writing; if you made it by being sincere with people, don’t turn slick and calculating.

A lot of people, once they’re successful, start to look down on the “skills that got them started.” They think this thing is too lowbrow, that thing is too much work — “I’m a big shot now, I should be doing big things.”

End result: the big things never pan out, and the skills they started with are gone too. They end up with nothing.

Don’t lose the thing that puts food on your table. It sounds simple, but not many people actually live by it.

Second, make a few friends who dare to tell you the truth.

The higher you climb, the less truth you’ll hear from the people around you.

It’s not anyone’s fault — it’s just human nature. When you’re in a position of power, people naturally weigh their words before they speak to you: will this offend him? Will he be upset?

That’s why you have to actively seek out people who’ll tell it like it is. It might be an old friend, a senior mentor, or even that most straightforward employee on your team.

Once you find them, treasure them. Don’t get mad every time they say something hard to hear. Get mad once, and they’ll never say it again.

利見大人 (It Furthers to See the Great Person) doesn’t mean you should go schmooze with higher-ranking officials or richer people. It means you should seek out people who can keep you grounded.

Finally, think ahead about how you’ll walk the downhill path.

This might not sound nice, but it’s practical.

No one stays at their peak forever. You’ll come down eventually — either by choice, or by force. If you come down on your own terms, you get to choose how and when. If you’re forced down? All bets are off.

So while you’re at your peak, you need to start thinking: when I step down later, how will I support myself? What backup plans do I have?

Is it having enough savings? Training a successor? Building a second career track?

Don’t wait until you’ve already fallen to think about it. When you’re falling, you might not have the strength to plan anymore.

Final Thoughts

That older buddy told me later that he’d figured it out.

He said he’s planning to hand over the day-to-day operations of the company and stay on only as an advisor. Then he’ll spend more time with his family, and do the things he’s actually interested in.

“I used to always think about making it bigger, making more money,” he said. “Now I realize — so what if it’s bigger? So what if I have more? No amount of size or money can bring back the feeling of having a simple meal with my family ten years ago.”

I said, “So after 飛龍在天 (Flying Dragon in the Heavens), you’re choosing to land gently back in the fields.”

He laughed. “Landing is better than crashing, that’s for sure.”

Yeah, exactly.

A lot of people think the goal of life is to keep flying higher and higher, the higher the better.

But that’s not really true.

The goal of life isn’t how high you fly. It’s whether you can fly when you’re supposed to fly, and land when you’re supposed to land. Whether you can fly beautifully, and land steadily.

飛龍在天 (Flying Dragon in the Heavens) is wonderful, of course. But what’s even more impressive than flying high is being able to fly up, and then come back down safely.

And once you’re down, being able to keep on living well.

Wen Laoshi often says that the wisdom of the I Ching (Book of Changes) isn’t about teaching you how to win — it’s about teaching you how not to lose.

At the position of the Nine in the Fifth Place of 乾為天 (The Creative), being able to hold steady and also step down gracefully? That’s true skill.

Being able to think about how not to lose, even when you’re a flying dragon in the heavens? That’s the real mark of greatness.