Flying Dragon in the Heavens: When Career Hits Its Peak, the Biggest Threat Isn’t Rivals but Yourself

How do you seize career opportunities? That’s a question so many people have asked me.

But I’ve noticed something even more interesting — most people don’t fail to catch opportunities; they fail to hold onto them once they’ve got them.

A while back, an older acquaintance invited me out for dinner. I call him “older,” but he’s not really old — just in his early 40s. He works in internet tech; his company got acquired a few years back, so he’s got a nice sum of money and a solid reputation. By all rights, he should be at the most triumphant point of his life.

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

I said, “You’re financially free and you’re anxious? What’s that supposed to mean for the rest of us grinding day in and day out?”

He said it’s not about money. He said everywhere he goes now, people kiss up to him — every word he says gets listened to, every idea he has gets praised. But he’s feeling more and more unsure of himself. “I can’t tell if I’m actually good at what I do,” 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, “The fact that you’re thinking this way means you haven’t let success go to your head. A lot of people in your position would already think they’re invincible.”

He gave a bitter smile and said, “That’s because I’ve seen way too many people fall from this height.”

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What Does "Flying Dragon in the Heavens" Feel Like?

The line text for Nine in the Fifth Place of the Qian (The Creative) hexagram reads: 飞龙在天，利见大人 (Flying Dragon in the Heavens, It Furthers to See the Great Person).

This is the most auspicious line of the Qian hexagram, and one of the most famous lines across all 64 Hexagrams. The dragon has soared into the sky, free and unbound, able to summon wind and rain at will. It stands high, sees far, and can do as it pleases.

Applied to life, this is the phase where your career is thriving, your position is secure, and your influence is at its peak. Put simply, it’s the state you land in after you’ve seized a big career opportunity.

What makes the Nine in the Fifth Place of the Qian hexagram so special? It holds the central position, is in proper position, and occupies a place of honor — it sits in the middle of the hexagram, balanced and unbiased; it is a Yang Line in a yang position, a perfect fit; and the fifth line is the most revered position in a hexagram. It has the favor of timing, the advantage of place, and the support of people all at once.

What’s it like to be a person in this phase?

First, people listen to everything you say. A casual remark from you gets jotted down immediately by those below, and carried out like a royal decree.

Second, people line up to help you with whatever you do. If you want to start a project, resources, connections, and money all come flocking to you on their own.

Third, you feel like you can do no wrong. Things that used to feel impossible now seem easy. People you could never win over before now come currying favor with you.

Does this feel good? Of course it does. Who wouldn’t love feeling this way?

But here’s the catch — 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 your success doesn’t come from your own skill — it comes from the position you hold, the resources at your disposal, and the platform behind you propping you up.

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

That’s the trap of "飞龙在天" (Flying Dragon in the Heavens) — the higher you fly, the harder it is to tell if you’re flying on your own power, or if the wind is the one carrying you.

That’s also why so many people end up falling even faster after they’ve seized a career opportunity. The opportunity gives you height, but that height can also cloud your judgment.

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The Three Most Common Mistakes People Make at Their Peak

I’ve seen far too many people fall from their peak.

The reasons they fall are all different, but if you boil them down, they come down to three mistakes.

First mistake: Thinking you’re invincible.

This is the most common one. When someone finds success in one field, they start thinking they can succeed at everything.

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.

By the end, they’ve lost their grip on their core business, and all their side ventures have lost money too.

I’m not saying you can never cross into new fields. What I’m saying is, when you do cross over, you need to stay grounded — in a new field, you’re a beginner. The experience you had before might not apply here.

When you’re a "flying dragon in the heavens," you’re flying in your own sky. Swap skies, and you might not be able to take off at all.

Second mistake: Tuning out opposing opinions.

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

After listening to too much flattery, you can’t stand hearing hard truths anymore. When someone raises an objection, your first thought isn’t “Does what they’re saying make sense?” — it’s “How dare they question me?”

Little by little, fewer and fewer people around you will tell you the truth, and more and more will just suck up to you. Everything you hear is what you want to hear; everything you see is what you want to see.

By the time you realize there’s a problem, it’s already too late.

That’s why the ancients said "利见大人" (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 aren’t afraid to throw cold water on your ego.

Only then can you stay clear-headed.

Third mistake: Forgetting to leave yourself a way out.

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

All they think about is: How can I climb even higher? How can I make even more money? How can I build even more influence?

Hardly anyone stops to think: What if I fall? Do I have a backup plan? Can I land safely?

Look at all those entrepreneurs and officials who end up in trouble — how many of them were brought down by someone else? Most of the time, they 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 a cliff, they realize they can’t hit the brakes.

The Qian hexagram has six lines total. "Flying Dragon in the Heavens" is the fifth line. There’s still one line above it — 亢龙有悔 (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 in the “flying dragon in the heavens” phase. Preparing for what? Preparing for how to come back down.

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Three Things You Should Do at Your Peak

So what should you actually do when you’re in the “flying dragon in the heavens” phase?

I think there are three things that matter more than pushing to climb even higher.

First thing: Guard your core foundation.

Whatever it was that helped you seize your career opportunity, hold onto it.

If you built your success on making great products, keep making great products; if you got where you are by writing, keep writing; if you earned your place by being sincere with people, don’t turn slick and calculating.

Too many people, once they find success, start turning their noses up at the skills that got them there. They think this skill is too low-end, that work is too hard — “I’m a big shot now, I should be doing big things.”

End result: the big things never pan out, and they lose the skills they started with. They end up with nothing on either end.

Times change, and methods get simpler over time. But one thing never changes — don’t lose the thing that puts food on your table.

Second thing: Make a few friends who dare to tell you the truth.

The higher you climb, the fewer honest voices you’ll have 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 speaking to you: “Will this offend him? Will he be upset?”

That’s why you have to actively seek out people who will tell you the truth. 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 won’t say it again next time.

To tell if someone can go the distance when a career opportunity comes their way, just look at whether there’s still anyone around them who dares to speak the truth. If everyone’s just kissing up, they’re not far from a fall.

"利见大人" (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 help you stay grounded.

Third thing: Plan for the downhill ahead of time.

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

No one can stay at their peak forever. You’ll have to come down eventually — either on your own terms, or against your will. If you come down on your own, 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? Having trained a successor? Having built a second career path for yourself?

Don’t wait until you’ve already fallen to think about this. By the time you’re falling, you might not have the energy to figure it out.

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A Few Final Words

That older acquaintance 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 work on things he’s actually passionate about.

He said he used to always think about making the business bigger, making more money. Now he realizes — so what if it’s bigger? So what if there’s more money? No amount of size or money can bring back the feeling of having a simple meal with his family ten years ago.

I said, “So after being the flying dragon in the heavens, you’re choosing to land back in the fields on your own terms.”

He laughed and said, “Landing is better than falling, any day.”

Yeah, exactly.

A lot of people think the goal of life is to keep flying higher and higher, as high as you can go.

But that’s not really true.

The goal of life isn’t how high you fly — it’s whether you can fly when it’s time to fly, and land when it’s time to land. Whether you can take off beautifully, and land safely too.

"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.

The Nine in the Fifth Place of the Qian hexagram isn’t just about how to fly high — it’s about how to stay clear-headed once you’re up there.

When you’re the flying dragon in the heavens, and you’re still thinking about how not to lose? That’s true mastery.