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Blog Your guide to financial planning and retirement
March 31, 2026 • 7 minutes
At some point — often quietly, often gradually — something shifts. The work that once energized you starts to feel heavier. The wins don’t land the same way. The edge you relied on doesn’t feel as sharp.
And yet… you keep going. Because that’s what successful people do, right? But recognizing when to retire may be the more important question.
In his book From Strength to Strength: Finding Success, Happiness, and Deep Purpose in the Second Half of Life, social scientist and author Arthur C. Brooks offers a different perspective, one that challenges the deeply ingrained belief that success means holding on as long as possible.
Instead, Brooks makes a compelling case that many of us are staying too long in one phase of life (late career), and missing the opportunity to thrive in the next (retirement).
Brooks describes two types of intelligence:
Fluid intelligence tends to peak earlier than we expect — often in our 30s or 40s. That doesn’t mean decline. It means transition.
As Brooks writes, “When you are young, you have raw smarts; when you are old, you have wisdom. When you are young, you can generate lots of facts; when you are old, you know what they mean and how to use them.”
The people who flourish long-term aren’t the ones who cling to their old strengths.
They’re the ones who recognize the shift and move with it.
If this transition is so natural, why don’t more people embrace it? Because it’s not just about work. It’s about identity.
So we stay. We double down. We push harder. We try to recreate a version of ourselves that worked before.
And in doing so, we often miss something bigger: the chance to evolve into a version of ourselves that could be even more fulfilled.
Brooks describes this tension directly.
“What I found was a hidden source of anguish that wasn’t just widespread but nearly universal among people who have done well in their careers,” he writes. “I came to call this the ‘striver’s curse’: people who strive to be excellent at what they do often wind up finding their inevitable decline terrifying, their successes increasingly unsatisfying, and their relationships lacking.”
There’s a simple equation Brooks offers: “Your satisfaction is what you have, divided by what you want.”
At first, success works exactly as expected. You achieve something, and it feels good. But over time, something changes. What you want expands faster than what you have. The bar keeps moving.
And the reward? It fades faster too.
“Humans simply aren’t wired to enjoy an achievement long past,” Brooks writes. “It is as if we were on a moving treadmill; satisfaction from success lasts but an instant.”
This is why so many people keep going even when it no longer feels right.
Another goal. Another milestone. Another year.
Because, as Brooks puts it, “the goal can’t be satisfied; the success addict is never ‘successful enough.’ The high only lasts a day or two, and then it’s on to the next success hit.”
Most people never stop to calculate what staying past that point is actually costing them.
The real risk in our 50s isn’t leaving the work force too soon, it’s transitioning or retiring too late.
When we hold on too long:
The irony? The people who plan retirement or transitions early often have more freedom, not less.
Moving on isn’t always about “retiring” in the traditional sense.
It can be about reallocating your time, energy, and purpose. For some, that might mean:
The goal isn’t to stop contributing. It’s to contribute in a way that aligns with your strengths and who you are now.
As Brooks writes, “Devote the back half of your life to serving others with your wisdom. Get old sharing the things you believe are most important.”
And more simply, “Get old sharing the things you believe are most important. Excellence is always its own reward, and this is how you can be most excellent as you age.”
If success and achievement aren’t the center anymore, what is? The answer is both simple and challenging.
As Brooks writes, “Satisfaction comes not from chasing bigger and bigger things, but paying attention to smaller and smaller things.”
And that shift is reinforced by how we define a meaningful life.
As he explains through the idea of résumé versus eulogy virtues: “Résumé virtues are professional and oriented toward earthly success… Eulogy virtues are ethical and spiritual… Your eulogy virtues are what you really would want people to talk about at your funeral.”
This is the reorientation.
Even our definition of progress changes. “As we grow older,” Brooks notes, “we shouldn’t accumulate more to represent ourselves but rather strip things away to find our true selves — and thus, to find our second curve.”
This is exactly the kind of decision Boldin is built for. Not just, “Can I retire earlier?” but:
With Boldin, you can model these scenarios in real time — seeing how changes to income, spending, timing, and goals affect your future.
Running scenarios in the Boldin Planner enables you to try on different possible futures — and see what really fits.
The question isn’t: “Have I squeezed every last drop out of this phase?”
It’s: “Is this still the highest and best use of my time and energy?”
And just as importantly: “Do I have a plan that lets me move forward with confidence?”
Because the truth is:
Strength isn’t holding on tight to the life you know now. It’s knowing when to shift. And having the clarity — and courage — to do it on your own terms.
As Brooks captures in a more personal reflection: “From my drive to be superior to others, deliver me… From allowing my pride to supplant my love, deliver me.”
That’s the deeper shift.
Many people stay in the wrong phase of life too long — not because they want to, but because they don’t have a clear path forward. But with the right perspective — and the right tools — you can make intentional, confident decisions about what comes next.
That’s what it means to go from strength to strength.
Not by holding on. But by moving forward.
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