The question high achievers never ask


Here's a question most people never get asked:

What would be enough?

Not "what do you want?" You've answered that a thousand times. Not "what are your goals?" You have spreadsheets for that.

Enough. The number, the title, the lifestyle where you could exhale and say: this is what I was building toward. I'm here.

If you're like most high achievers, that question just short-circuited something.

The most successful people I know have never defined enough.

They can tell you exactly what they're chasing. The next milestone. The revenue target. The promotion.

But ask them what would actually be enough - what would allow them to stop climbing and start living - and you get a long pause.

It's not that they can't answer. It's that they've never been asked.

There are reasons for this.

Today's economy doesn't want you to define enough. Enough is bad for business. Enough doesn't drive Q4 numbers. Enough doesn't get you to click "buy now."

The message everywhere is the same: there's always another level. More revenue. More impact. More.

And if you're someone who's good at achieving? That message is intoxicating. You've built your whole identity around being someone who reaches the next thing.

Defining enough feels like admitting you can't hack it at the next level. Like you're settling. So you don't define it. You just keep pushing.

But here's the thing about undefined "enough":

It's a trap.

Without a definition of enough, you're running a race with no finish line. Every win becomes a starting point. Every achievement gets a 48-hour shelf life before the restlessness returns.

Hit the number? Move the goalposts. Get the title? Eyes on the next one.

Your nervous system never gets the signal that you've arrived. Because you never tell it what "arrived" is.

I'm not talking about complacency.

I'm talking about the difference between climbing with intention and climbing on autopilot.

When you've defined enough, you can still choose to go beyond it. But it's a choice, not a compulsion. You're climbing because you want to, not because you don't know how to stop.

When you haven't defined enough, every pause feels like falling behind. Rest feels like laziness. Satisfaction feels suspicious.

So what does "enough" actually look like?

It's different for everyone. But here's a place to start:

Enough is waking up without dread. It's having time for the people who matter. It's doing work that means something to you.

The point isn't the specific answer. The point is having one.

Stoicism offers a practice: negative visualization. Imagine losing everything - your status, your wealth, your title. What would remain?
Then flip it: imagine having everything you're currently chasing. The number. The recognition. The success. Now what? Would you finally be satisfied? Or would there just be another goal?

If there's always another goal, you haven't defined enough. You've just defined "next."

Here's what I've learned, mostly the hard way:

Enough isn't a ceiling. It's a foundation.

When you know what enough looks like, you can build from sufficiency instead of scarcity. You can say no to opportunities that would impress everyone but drain you.

Undefined enough keeps you hungry. Defined enough keeps you free.

This week, sit with two questions:

What would a content life look like? Not your "best" one. Your enough one. And how would you actually know when you're there?

Second Summit Brief by Clif Mathews

Second Summit Brief is a weekly letter for high-achieving leaders who’ve realized the summit they climbed isn’t the one they want to stay on. Each edition blends reflection and strategy to help you see the patterns keeping you stuck and find the clarity, courage, and integration that define your own second summit.

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