Not Done Yet – Lessons from The Long Middle

There’s a moment in every career when the chase slows—but the questions sharpen. For those of us in our late 40s and 50s, watching Boomers extend their tenure while companies bet on AI-native Millennials, that moment has arrived with particular urgency.

Midlife is when the universe grabs you by the shoulders and says: I’m not f***ing around. — Brené Brown

You’re no longer climbing simply to climb. You’re asking what the view is for.

You start listening more than proving.

You think in terms of systems, not sprints.

You realize what feels like the middle might actually be the part where your best contributions begin.

I used to imagine that moment as some future “Second Act.” Now I recognize it as now.

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⏳ Accumulated, Not Obsolete

I’ve spent most of my working life building at the edge of change. Some of that was digital—transforming marketing systems, launching new product lines, growing teams across industries from defense to climate tech. Some of it was human—coaching people through transformations, asking better questions, reframing the “why” of the work.

It wasn’t linear. It was iterative.

Each chapter demanded more perspective, more pattern recognition, more discernment.

And while the early years taught me the rules, it’s the long middle that taught me which ones were worth keeping.

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🧠 The Hidden Value of Midlife Leaders

This week I was struck by Chip Conley’s reflection on becoming Airbnb’s “Modern Elder” in his 50s. He wasn’t there to code or scale—he was there to solve problems the founders didn’t even know they had.

While Brian Chesky and his co-founders understood technology and growth, Conley brought something irreplaceable: deep hospitality wisdom. He created the nine quality standards that turned amateur hosts into professionals. He designed the “Hospitality Moments of Truth” classes that taught hosts how to create memorable experiences, not just provide beds. Most crucially, he bridged Airbnb to the traditional hotel industry—facilitating dialogues with major chains that could have been adversaries.

The results spoke for themselves.

During Conley’s tenure, nights booked nearly doubled in 2015, reaching 78 million. More telling: Airbnb’s Net Promoter Score climbed to 50% higher than the hotel industry average. Guest review rates hit 70%—nearly triple the traditional hotel industry’s 20-25%. Revenue was on track to hit $1 billion.

This wasn’t coincidence. It was the compound effect of institutional wisdom applied to disruptive technology. That’s not something you can automate or outsource to a 25-year-old, no matter how brilliant.

Peter Richmond learned this at 50, though not by choice. After decades as a celebrated journalist—writing for GQ, interviewing Muhammad Ali and Kobe Bryant, living the expense-account lifestyle of 90s magazine culture—he was let go. The teaching job he took at a private school paid a fraction of his former salary.

But something unexpected happened. When offered a chance to interview Claire Danes for a magazine story, Richmond turned it down. His editor was shocked. His students were baffled. His answer revealed everything: he found his students and their ideas more interesting than celebrity culture.

Years earlier, while reporting on aging, Richmond had interviewed a psychiatrist who shared findings from a long-term study: men who aged most gracefully often took divergent work paths in their 50s and 60s, abandoning successful careers for entirely new ones. At the time, it was just a quote. At 50, it became a roadmap.

Richmond had spent decades perfecting the craft of drawing stories from famous people. Now he was helping young minds craft their own stories. Same skills, deeper purpose.

Both men discovered what I’m learning: the long middle isn’t about starting over—it’s about integration. Taking everything you’ve built and asking not ‘What’s next?’ but ‘What matters most?’

But here’s where the conventional wisdom gets it wrong.

Facing the economic reality of longer-working Boomers and AI-favored Millennials, many voices insist Gen X has only one choice: go entrepreneurial or get left behind.

That’s a false dichotomy.

Not everyone wants to be an entrepreneur—and they shouldn’t have to be. The corporate world still needs someone to bridge the Boomer-Millennial gap. Someone has to be the integration specialist who translates between generations, the AI implementation guide who understands both technology and human change management.

The path forward isn’t about rejecting organizational structures—it’s about strategic repositioning within them, or finding new structures where accumulated expertise becomes indispensable rather than obsolete.

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🔄 My Career Has Been One Long Iteration

Without diving into the résumé, here’s what I’ll say: I’ve done a lot of firsts—the kind that came naturally to those of us who built the digital infrastructure most companies still run on.

First platforms.

First teams.

First content engines.

First product launches.

But I’ve also been the one to stick around after the firsts—

To systematize what worked.

To mentor others.

To simplify the overcomplicated.

To stop chasing “scale” when what we needed was resonance.

That’s what the Second Act teaches you.

Sometimes growth means deepening, not just expanding.

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🛠 Second Act Skills That Matter More Now Than Ever

If you’re navigating this generational squeeze in your 50s, here’s what I think matters most:

🔍 Institutional memory: Knowing when it’s not a bug, but a loop you’ve seen before

🧭 Systems perspective: Seeing around corners without needing to run faster

🎯 Strategic clarity: Saying “no” more often, and “not yet” even more

🤝 Cross-generational mentorship: Building others without building ego

✨ Context integration: Turning work into story and story into signal

These are not things AI will replace. These are the things AI will need you for. When machines can generate infinite options, human judgment about which options matter becomes invaluable.

The Thread That Connects

Earlier this year, I wrote about three essential leadership skills AI cannot replace: Cooperation, Delegation, and Asking the Right Questions—drawing heavily on Lynda Gratton's research on cooperation as today's essential power skill.

What I'm realizing now is that these aren't just individual skills—they're the foundation of what makes midlife leaders uniquely valuable. The cooperation imperative Gratton describes? That's exactly what Chip Conley brought to Airbnb—bridging the gap between tech founders and traditional hospitality. The delegation mastery I explored? That's what Peter Richmond discovered in teaching—transferring not just knowledge but authority to young minds. The ability to ask the right questions? That's what distinguishes institutional memory from mere experience.

These skills don't diminish with age—they compound. And in an AI-accelerated world, they become the bridge between technological capability and human wisdom.

The professionals thriving in their 50s+ aren't just leveraging individual expertise—they're the ones who've mastered cooperation across generational and technological boundaries. They're not just experienced; they're integration specialists.

This is why the false dichotomy between "go entrepreneurial or get left behind" misses the point entirely. The most valuable role for midlife professionals might be exactly where they are—if they can position their accumulated cooperation skills as the missing link in organizations struggling to bridge generational and technological divides.

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🎯 Closing Thought

If you’re not done yet, good.

You’re not supposed to be.

Second acts aren’t about reinvention for reinvention’s sake.

They’re about integration.

They’re when your skills meet your values.

When your work stops just being impressive—

and starts being true.

The long middle isn’t where careers go to wind down. It’s where they finally wind up to their real purpose.

Thanks for reading. I’ll see you next week.

Madam I’m Adam

A version of this article originally appeared on AdamMonago.com on 7-August-2025.