Hammerin's All I Know To Do

By: Kristen Heaney

He built an empire, conquered challenges most people can’t even fathom, and yet something still feels just out of reach. The next deal, the next venture, the next milestone, surely that will be the thing that makes it all feel complete. But what if the very drive that got him here is also what’s keeping him from feeling satisfied?

Arthur Brooks calls it the Striver’s Curse - the relentless pursuit of achievement that, while outwardly celebrated, can quietly erode one’s sense of fulfillment. We see this often - those whose success has brought them extraordinary wealth, influence, and responsibility, but who remain tethered to an insatiable drive for more.

For some, this manifests as an unyielding desire to expand their business or investments, even when the existing enterprise is straining under the weight of its own complexity. For others, it’s the compulsion to exponentially grow their wealth, despite the reality that their family office already struggles to manage its current scale. The paradox of success is that the very striving that built a legacy can also become the force that destabilizes it.

I get it, as the daughter of an entrepreneur, and business owner I struggle with it too. The nagging feeling that I should be doing more. The allure of the next idea to expand and improve...its exhausting.

And exhilarating all at once.

I recently read, Andrew Wilkinson's book Never Enough, - he describes his own flirtation with this endless chase:

“When does it end? You make $1 million, you want $2 million. You make $2 million, you want $10 million. You make $10 million, you want $100 million. The goalposts never stop moving, and you never arrive.”

Journalist and author David Brooks (How to Know a Person), reflecting on Carl Jung’s insights, observed that “the achievements which society rewards are won at the cost of diminution of personality.” The external validation—the accolades, the influence, the expansion—often come at an internal cost. At a certain point, even the most successful among us begin to feel a hunger for something deeper, something enduring. “Eventually, the costs become too high,” Brooks writes. “The person at the end of this task realizes there is a spiritual hunger that’s been unmet…a desire to leave some legacy for others.”

The danger is that, without clear and compelling markers of success in stewardship and legacy-building, many high achievers default to what they know: conquest, expansion, accumulation. The rush of another deal closed, another investment secured, another complexity mastered can mimic the rush of a dopamine hit—something akin, in a way, to addiction. Lyrics of the Dave Matthews Band song, Looking for a Vein hauntingly illustrate this drive:

“What if I strike it? Rich as I wanna be.

Will it set me free or be just another hole to dig?

But I can't give up on this.

Always trying to break on through.

This air is choking me.

But hammerin's all I know to do."

How can you break free from this cycle? How do you redefine fulfillment so that you’re not just endlessly digging, but instead actually building something intentional?

One antidote, as Arthur Brooks suggests, is the shift from placing a primary value on fluid intelligence—the quick-thinking, problem-solving mind that drives many high achievers—to crystallized intelligence: the wisdom and mentorship that comes with experience. This is the shift from accumulation to contribution, from building wealth to stewarding it well.

But without clear definitions of success beyond financial expansion, it’s easy to get stuck in the endless chase. The key is finding the dopamine hit in preparing something sustainable for future generations and preparing them to steward it, in crafting a shared vision, in investing in the intangibles of relationship and meaning, and in designing structures that allow your wealth to serve you rather than consume you.

You have the choice: keep hammering away at the walls, searching for the next big thing - or step back and celebrate; You've already won the game of success, and can now create a new definition of success, pursuing areas of life that bring you true and lasting meaning. That's a game worth winning - no hammer required.