Brand New

What is your brand?

It's a simple question, one I thought I had down cold. But when someone I respect asked me that last week, I questioned what I thought I knew. I had an answer, but it lacked the punch of conviction.

Since then, I've been thinking about elevating my brand. I want to think of myself as a Rolex. It's my era of Rolexification: a brand that represents craftsmanship and quality, endurance, resilience, and investment-worthy value. As I navigate my own journey to figure out 'what's next,' I realize my brand needs to be solid. I need to exude confidence and poise, something upleveled to represent what you get when you invest in me.

The same person who asked about my brand also reminded me to go back to basics. StrengthsFinders basics. I've been given no fewer than six copies of StrengthsFinder 2.0 over my career; that’s roughly one every three years. Ironically, I couldn't find a single copy in my apartment. Off to Amazon I went.

But this time was different. I wasn't playing for a team where I needed to understand others' strengths and weaknesses. I was on a team of one, and my strengths are my brand.

It's amazing how familiar tasks can have profoundly different meanings when circumstances change. Completing StrengthsFinder for the sixth time became the highlight of my day and the dinner table conversation. I felt like I'd unlocked knowledge about myself I never knew, more powerful about speaking to my brand. I went back with a highlighter, filing away nuggets for my mental "Reminder to Self" folder:

"You alone have a billion-dollar potential. Think of your strengths as your biggest financial asset."

"When life finds you in a dark place, your best friend is always your strengths."

"When you make the most of your strengths, there are no limits to what you can do and how you can lead."

Here's what this taught me: I sort of understood my strengths before, but I wasn't explaining them in a way that was Rolexifying my brand. I wasn't elevating myself for what I know I'm capable of. Not in a "give this to me on a silver platter" kind of way, but rather: these are my strengths, and I'm a billion-dollar institution if you want to take a piece of my equity. 

Knowing your strengths is one thing, but having the resilience to rebuild with them is another.

Yesterday marked the 24th anniversary of September 11th. While I was on a run - with One World Trade Center in my direct line of sight for miles - questions about my brand racing through my brain, I was transported back to that exact day 24 years ago.

I was a freshman in high school, first period, Mr. Perkin's science class. The weather was much like my running day - fall in the air, summer holding on. A classmate arrived late, announcing something had happened in New York City. A plane hit a building. Class resumed until fourth period, when we watched history unfold.

At fourteen, I had no dreams of living in New York City. I didn't understand this city's strength or how those events would reshape the world. Now, 24 years later, I'm here raising a child, and this city has returned stronger than ever. Living here is a masterclass in reinvention: it demands everything from you, then gives you the grit to handle anything. Every subway delay builds patience, every rent check builds determination, every small victory feels monumental because you earned it against the odds. This city doesn't let you stay comfortable; it turns your worst days into your origin story.

If I'm going to rebuild my brand, I'm choosing to draw inspiration from a city that refuses to stay down. New York didn't just recover - it evolved. It didn't try to become what it was before; it became something better. Its brand transformed from tragedy through resilience into renewed strength. Just like the city, I'm not starting over - I'm leaning into my existing strengths to become a version of myself I might never have discovered without this catalyst.

And as I’ve been thinking about this more and more I realized: this whole ‘evolve under pressure' thing isn't just a me problem - it's generational.

This got me thinking about my generation's relationship with reinvention. We Millennials have been shaped by capstone moments that forced constant adaptation: 9/11 during our formative years, Facebook's arrival as we were graduating high school, the 2008 financial crisis as we were entering our early professional years, a pandemic while juggling family and mental health, and now, hello, AI!

Think about it: at pivotal life moments, we've faced world-reshaping events, yet we've adapted, endured, and moved forward. 9/11 changed how I think about security… everywhere. Facebook redefined social connection and identity. The 2008 crisis stunted our homeownership and career stability. The 2020 pandemic interrupted our prime earning years and reshaped our family and job choices.

As a parent, I want my daughter to be more successful than I ever was. But I also want her to inherit a world where being successful doesn't mean constantly bracing for the next economic curveball. Looking at my peer group, we've had it pretty damn hard. What if our brand isn't despite these disruptions, but because of them? What if our superpower is actually our ability to reinvent?

But here's what's been nagging at me - 

Everyone's worried about the future of work and AI disruption, but why is no one talking about us? We're so concerned about "our country's boys" and trade school alternatives, but what about the prime Millennials caught in the squeeze?

Picture this person:

This person doesn’t have deep technical skills, but they’ve worked their way up in an industry ripe for AI disruption. As the company focuses on doing more with less and sharpen their pencils, this person is suddenly wondering: "Is this it? Is this the end of my professional run?"

I suspect this persona hits close to home for many of us; not a one-size-fits-all situation, but with parallels too strong to ignore.

Here's what I think we’re not talking about: We talk about retraining and reskilling like it's simple, but when you're 38 with a mortgage, two kids in school, and aging parents to think about, you can't just hit pause on life to learn Python. The 22-year-old who can pivot to trade school? That ship has sailed. The flexibility to take a pay cut while you retrain? Not when you're supporting a family.

We've made rational life choices - buying homes, having kids, or investing in our children's education - within the economic reality we inherited. Now we're being told those very choices might have painted us into a corner just as the next technological tsunami hits.

I once jotted down a quote that stuck with me:

“The best regulations are life lessons.”

In other words: you can regulate behavior with laws, but you can’t regulate wisdom - that only comes from living, failing, learning, and carrying those lessons forward. Our generation’s rules were, and still are, being written in real time, through trial and error, and those lessons became our operating system.

I've invested in understanding technology and branding myself as semi-AI-proof for future chapters. But the anxiety is real. We're the generation that's supposed to be in our prime earning years, carrying the economic load for our kids (and maybe our parents), and we're facing potential career obsolescence at the worst possible time.

So while everyone debates the future of work in abstract terms, some of us are asking much more immediate questions: How do you evolve your brand when evolution feels like a luxury you can't afford?

This is something I want to dig deeper into in future editions of Is This It?. I can't be the only one thinking like this, right? I have to imagine this squeeze is going to impact all of us at some point, one way or another. How are others in similar situations preparing? 

Look, I could spiral into doom and gloom about all of this generational pressure, but that's not my brand either. While I'm figuring out how I (we) navigate this squeeze as a generation, I'm also focused on something more immediate: how I want to show up in the world right now. And that branding is a bit more physical 💪🏼.

Sunday evening brought our annual tradition: watching the MTV Video Music Awards. This year, I found myself uttering the same bewildered questions my parents asked during my prime MTV years: “What is this?” and "What is going on?"

But then Ricky Martin took the stage.

At 53, receiving the Latin Icon Award, he was singing live, dancing with seemingly twenty-something joints, his body chiseled, his face showing natural lines that suggested care but also graceful aging. I was genuinely impressed. From a branding standpoint, I thought: that's how I want to age. Not fighting time, but evolving with it - authentic, confident, still very vital.

My brand needs to be as much physical as intellectual. I want to show up with great ideas, enjoy active moments with my daughter when I'm older, move like I'm her age, and maybe someday embrace those fine lines… because they represent years of wisdom and better-defined character.

So here's what I'm learning: authentic branding isn't about perfection or staying the same. It's about resilient evolution… like New York City post-9/11, like our entire generation's relationship with constant change, and even like Ricky Martin at the ripe age of 53. The punch of conviction comes not from having all the answers, but from knowing your strengths and adapting to thrive no matter what comes next.

That's a Rolex-worthy brand. That's a billion-dollar institution worth building on.

The weekly section where I will call out a fraction: something that felt like progress this week (like a fraction forward) and a fiction: something that turned out to be a distraction or illusion. 

🎯 Fraction: Golden from K-Pop Demon Hunters has been on heavy rotation in our house, and it’s officially become our go-to dance party anthem. My daughter and I spin, jump, and laugh like no one’s watching and while she may not remember these living room concerts years from now, I know I will. It’s a fraction of pure joy I’ll carry with me long after the song fades.

🎭 Fiction: The New York Times tried to tell me I’m not a Scorpio. Apparently, because of the Earth’s axial wobble, the constellations have shifted and our zodiac signs are “wrong.” I believe the science, but I refuse the rebrand. I know I’m a Scorpio. Everyone who knows me knows I’m a Scorpio. You can move the stars all you want, but this is one identity I’m not reinventing.

If this week’s edition gave you that punch of conviction, don’t keep it to yourself. Share it with a friend or colleague who’s working on their own brand evolution. The bigger this community grows, the more power we all have to evolve and thrive together.

Until next Friday,
Chris

Next Week: A story that’s still writing itself.

Curious what my top 5 strengths are? Here’s the foundation my brand is built on.