JULY 16, 2026

Ambition’s second act

Last weekend I found myself watching livestreams of Jay-Z’s three sold-out concerts at Yankee Stadium for the 30th anniversary of his first album, Reasonable Doubt.

I distinctly remember the first time I heard Jay-Z on an underground mixtape in the summer of 1995, before his first album even came out.

His voice was so different than other rappers. It was high-pitched and a bit squeaky and stood out when compared to say, Notorious B.I.G. or Method Man, who were dominating the airwaves at that time. I was immediately hooked and wondered if/when we would hear more from him.

A few months later, I moved to New York having just graduated college. I rented a studio apartment in a brownstone home at 441 State Street in Brooklyn and took the train uptown to Columbia every day for grad school.

In a strange coincidence (which I would learn about later through his interviews and song Empire State of Mind), Jay-Z actually lived just a block away at 560 State Street in those same years.

Back in 1996, when the internet was new, we still listened to CDs and tapes, and social media didn’t exist, you likely never heard of Jay-Z unless you were an intentional follower of east coast hip hop music. No record company would sign him, so he bootstrapped the independent production and distribution of Reasonable Doubt, which, even when released, sold only 43,000 copies in its first weeks.

So, watching him thirty years later this weekend, thinking about how in that timeframe he reinvented himself from a local street dealer to independent music artist to record executive to entertainment/sports/spirits mogul to ultimately global icon, my mind went to something much deeper than just a trip down memory lane with his songs.

I found myself thinking about time, and in particular, mine.

For a few moments, it felt as if three decades of my life had blended into each other. I wasn’t watching a concert in 2026 as much as I was remembering the young 22-year-old I was, who first bought that CD and all the possibilities he imagined his life might hold.

I tried to remember what ambition looked like for me back then, and what, if anything, came of it. And I started to think about today, asking myself: what does ambition look like for the second half?

We stop comparing futures

I’ve always been someone who struggles with imagining the future.

I’m much more attuned to looking backwards. I like to reminisce and remember. While others daydream about their futures, I enjoyably get lost in the past.

While this approach can be useful for learning from prior mistakes and having a strong memory, it doesn’t lend itself well to strategically playing the long game.

Ultimately my long game goals get accomplished, but that’s largely due to time passing and me constantly pivoting. I’ve just never been the guy who was comfortable mapping out a five-year plan for his life. Sometimes not even a one-year plan.

But when we’re young, that’s okay. There’s always time. We can imagine things without planning and still know we have runway. If we get stuck in comparison, we know that everyone else is also still mostly in their potential phase.

And then somewhere along the way, the comparison quietly changes. We can no longer compare futures, so we begin comparing lives.

Think back to the people you started alongside in life: maybe in a class, your freshman dorm, or your first job. Everyone seemed indistinguishable in their potential.

Thirty years later, the randomness of who ended up where can seem to calcify into something that feels like a verdict on what a good life really is.

And this isn’t about envy or wanting someone else’s life. Rather, it’s something deeper: enough life has happened now that we’re no longer comparing possibilities. We are comparing the choices, tradeoffs, and circumstances that shaped the lives we’ve actually lived.

Not being able to go backwards and yet (in my case) often wanting to mentally live in the past as opposed to facing the future, indeed invites a lot of questions to reflect upon.

The questions change

One of the privileges of coaching leaders is having a front-row seat to the questions others ask at different stages of life.

I’ve found that early in our careers, the questions are usually rooted in external validation, such as:

How do I get promoted? How do I prove myself? How do I become successful?

Over time, the questions become profoundly reflective:

Am I spending my time on what matters most? What have I been chasing all this time? What kind of legacy am I creating? If I could live these last twenty years differently, what would I have done differently?

These are less questions of ambition and more ones of perspective. The paradox is that only after living can you actually see the shape of your life. This is why regret is such a challenging mindset to conquer.

As much as you would have loved to have done certain things differently, you couldn’t have, with the consciousness you had at that time. And you wouldn’t even be considering these thoughts were it not for having already made those past decisions that led you here.

What nostalgia may be trying to tell us

My fascination with the past has always made me easily nostalgic. It’s a reason why I couldn’t get enough of the Jay-Z concert and why I love reading history, and why I often will scroll through thousands of old family photos as a fun hobby.

One day I learned that the word nostalgia comes from two Greek words: nostos, meaning “to return home,” and algos, meaning pain.

That made sense to me. Unlike my wife and many of my friends, who can look at the past with appreciation but not attachment, I often would ache for those days. And in a strange way, I didn’t want to let go of the ache because it was the only way to make sure I didn’t forget and just move on.

For most of my life I assumed this was a flaw or a sign of weakness; that I was too emotionally connected to events in life and that success was all about being stoic and constantly running toward the future.

Now I’m not so sure. I’ve started to wonder whether nostalgia is useful by asking us to pause and take inventory of life. Perhaps it provides a valuable reminder to notice which parts of our younger selves still deserve a place in our future.

For instance, think of how much more curious and optimistic and seemingly invincible that younger self was. Maybe those were qualities we aren’t meant to outgrow as we age.

In this way, nostalgia isn’t just about reminding us of past events but actually reconnecting us with who we once were. And I wonder if it arrives at the exact moment we need it, to help guide us through the confusion of not knowing what our next act should be.

A different kind of ambition

In watching those concerts and reflecting on Jay-Z’s arc, I realized he also fueled his rise through the nostalgia of his life. Perhaps he didn’t imagine at 26 what he would be now at 56; or maybe he did. But listen to any of his lyrics and you find that he’s constantly reflecting and sharing stories from his prior acts as a way of guiding himself to the next reinvention.

I think there’s a lesson there that applies to all of us, which is to take the time to remember your stories, share them and don’t push them away in the ambitious hunt for more. They are the very things to honor for your next ambition, not erase.

In our first half of ambition, we asked: “What can I become?”

But in the second half we ask, “Given who I’ve become, how do I want to live now? And, how do I make room in this second act for the best of my younger self?”

These are very different questions: the first is about building a life. And the others are about understanding it, not just letting it pass you by.

Sure there are paths we’ll never take and versions of ourselves we’ll never become. But there are still stories to build on, people to love and courage to contribute to the world. And that second half of ambition doesn’t have to be about becoming someone entirely new. It may just be about finally living with the wisdom you’ve earned and can finally apply with ease.

Until next week, all my best,

Nihar

P.S. Back in 2021, I wrote an article about Jay-Z’s induction into the Rock and Roll Hall of Fame for Forbes. If interested, here’s the link:

Five Lessons For Founders And CEOs From Jay-Z’s Rock And Roll Hall Of Fame Induction Speech