When Is Enough Enough?

The Missing Finish Line

Growing up, my parents had a beach house.

Not a fancy one. A lived-in one. Sandy floors. Damp towels slung over the back deck railings. A garage fridge with an extension cord run from the house, nicknamed the magic fridge, always stocked with beers by Friday.

Everyone was welcome on weekends. Friends. Friends of friends. Cousins who showed up unannounced. By Friday night the house was full. By Sunday afternoon it emptied itself, like the tide pulling back.

If you know my family, you know we love people. We love a good party. We love a night that stretches longer than planned.

But there was always a moment.

It might be midnight. It might be later. The music a little too loud. The conversation looping. Someone opening another beer when no one really needed it.

That’s when my father would yell from somewhere in the house:

“When is enough enough?!”

Loud enough to cut through the noise.

The party didn’t end immediately. It rarely did.

But something shifted. People laughed. Someone turned the music down. A few folks grabbed their flip-flops.

It was framed as a question.

Everyone knew what it meant.

And it stayed with me.

I think about that line a lot now.

Because somewhere along the way, most of us lost the ability to ask it.

Not about parties. About work. About money. About how much striving is actually required before we are allowed to exhale.

We were taught how to start races.We were never taught how to recognize the finish line.

So we keep running.

We add hours because we can.

We defer joy because it feels responsible.

We tell ourselves we will reassess next year, or once things settle, even though things never really do.

What’s strange is that for many accomplished people, the danger is not scarcity.

It is momentum without intention.

We are misaligned, and we have lost our sense of when enough is enough.

Here’s the part no one says out loud.

For a lot of us, nothing is actually wrong.

The career worked. The money mostly worked. The life, on paper, worked.

And yet the motivation that used to carry you feels thinner. The goals do not land the same way. You keep pushing, but you are no longer sure what you are pushing toward.

Psychologists call this the arrival fallacy, a term popularized by Tal Ben-Shahar.

It is the belief that once you reach a milestone, you will finally feel satisfied. Settled. Done.

Except the feeling does not last.

You adapt. Quickly.

So you set the next goal. And then the next one. Often without stopping to ask whether the race is still worth running.

No one rings a bell when you arrive.

There is no announcement that says, “You’re good now. You can ease up.”

So most of us don’t.

Developmental psychology backs this up.

There is a point in life when the question quietly shifts from What can I build? to What actually matters now?

The problem is that our culture never updates the scoreboard.

We keep measuring ourselves by hours, output, titles, accumulation of wealth and stuff, even when those metrics have stopped feeding us.

So when people say, “I feel restless,” or “I should be grateful but I’m not,” or “I don’t know why I’m still pushing this hard,” it is not shameful.

It is a signal.

Here’s where I’ll say something slightly irreverent, because it’s true.

Most people I know who feel restless are not restless because life is objectively hard. They are restless because they have been doing the same thing for a long time, and something in them knows it is time for a change.

They have learned the system. They have proven themselves. They have stayed longer than required.

And now there is a low-grade irritation. A nagging sense that it is time to switch the race.

One client put it this way:

“I’ve been focused on the same work for the past ten or twelve years. I’m getting to the end where I’m not sure I can keep doing this same thing.”

Not burned out.

Not in crisis.

Just at the edge of knowing something has to shift.

He came to our session with an idea already forming. Exploring a small business opportunity with his nephew. In one focused hour, we peeled back all the reasons he could say no.

What emerged underneath was clarity.

He wasn’t leaving his current position.

He was exploring with intention and curiosity.

He was staying employed while searching for what’s next and what could be.

That’s the moment this writing is about.

The nagging sense that you’re still running, even though you’re close enough to home to feel the urgency.

Enough feels suspicious in a culture that worships momentum.

But momentum without intention is just inertia with better branding.

At some point, continuing to push is not noble.It is just unexamined habit. Something we’ve been doing for so long we stopped asking why.

There is also research showing that once basic needs are met, control over how you spend your time matters more to well-being than more money.

Which explains a lot.

People do not fantasize about bigger spreadsheets.

They fantasize about owning their mornings. Their energy. Their calendar.

In other words, what most of us are really asking is not How much more can I make?

It is How much longer do I want to live like this?

And that is a very different question.

I don’t think “enough” is a number.

I think it is a decision.

A moment when you stop outsourcing your stopping point to culture, comparison, or fear.

A moment when you ask yourself the same question my father asked a group of happy, slightly over-served people sitting on the front fence:

When is enough enough?

Not because you are done living.

But because you are ready to change the race and live on purpose.

— Carolyn

For the curious, not the convinced

If you want to go deeper on this idea of enough, and the shift underneath it, here are a few places to explore:

• Die With Zero by Bill Perkins

• Start Late, Finish Rich by David Bach

• Research on time affluence by Ashley Whillans

• Work on happiness and adaptation by Daniel Kahneman

• An earlier edition of The Vital Shift, The Ego Shift, where researchers call this transition generativity and I called it the moment your ambition gets smarter