“Every career has a midnight hour. The smart people exit at five to twelve.”
– Sanjay Khosla

Relevance Reboot is a series of personal essays on technology, work, and staying relevant later in life. Many of us reach a point in our careers where the questions begin to change. These essays are my attempt to think out loud about personal relevance: how it fades, how it’s renewed, and how to notice the difference.

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I’m often asked by people I don’t know, “What did you do for your career?” The emphasis is on did, with the obvious assumption that whatever I did is past tense.

It doesn’t really bother me, but it does reveal something familiar, especially in technology. There’s an unspoken belief that age and relevance move in opposite directions. Ageism is real. I’ve seen it. I’ve felt it. It’s unfair and pretending otherwise doesn’t help anyone.

But there’s another uncomfortable truth I’ve seen – not all relevance is taken from us. Some of it quietly expires while we’re not paying attention.

When I turned 60, I made a conscious decision not to let age alone define my trajectory. I’ve always liked Clint Eastwood’s line about “not letting the old man in,” not because it’s macho, but because it reminds me that disengagement is often a slow drift, not a sudden fall.

After nearly four decades in technology and cybersecurity – from the US Navy to Fortune 500’s, big governments to tech startups, and board director to advisor roles – I’m still excited by new technologies. But excitement isn’t enough. Staying relevant as my beard turned gray has required something harder: repeatedly putting myself back into a learning posture, even when it’s uncomfortable.

More recently, working at the intersection of cybersecurity and AI forced me back into that learning posture. I had to admit what I didn’t know and relearn how to learn. I went back to school in a way I hadn’t in years, and while I’m certainly no expert, the experience reinforced something important for me: relevance isn’t about what you’ve already mastered, it’s about your willingness and ability to master what comes next.

That’s where things get uncomfortable.

I’ve watched smart, experienced, and capable people, both friends and colleagues I respect a great deal, reach a point where the world around them changed faster than their internal models. I don’t say that with arrogance. I say it because I’ve caught flashes of that same risk in myself, and that recognition is unsettling. It’s frighteningly easy to rely on instincts that once served you well but no longer fit the environment.

The technology world is a fast-moving train where the shelf life of expertise is far shorter than most of us want to admit. Experience still matters, but only when it’s paired with curiosity and renewal. The danger isn’t age. The danger is assuming that yesterday’s playbook still applies by default.

@Tom Quinn told me, “I think it’s important to hold the mirror in front of yourself every day and ask, ‘Would I hire you?’” Answering that mirror with brutal self-honesty is where the real work begins. It forces you to separate reputation from relevance and tenure from traction.

I don’t pretend to have a single litmus test, but there are a few signals I personally stay alert to.

I’m probably still relevant when:

• People seek my input because it helps, not out of politeness or courtesy
• My ideas spark debate rather than nostalgia
• I can influence outcomes through insight, not just my title or position

And I worry when:

• I talk more about what I’ve done in the past than what I’m working on today
• I avoid new tools instead of wrestling with them and investing the time to learn them
• Younger colleagues stop asking me what I’m working on, or what’s next

I certainly don’t think relevance is about clinging on indefinitely. Rather, it’s about staying engaged – while you’re still learning, still useful, and still honest with yourself. A few close friends and I even have a quiet agreement we jokingly call the 5-to-12 rule, a way of helping each other notice when their engagement starts to fade, especially when the person drifting may not see it themselves. It’s not about forcing an exit. It’s about awareness and having the dignity and choice to decide what comes next before circumstances decide for you.

I’ve always liked @Jane Lute’s description of this stage of a career. She calls it: “Clearing brush and creating opportunities where we can for the next generation. Making connections and offering advice when asked, and sort of a ‘down in front!’ message to ourselves to let the younger folks make their way and their mark.”

That framing resonates with me. It acknowledges experience without clinging to it. It recognizes that relevance sometimes means stepping back just enough to let others step forward: while still being useful, connected, and engaged.

Reinvention can be a powerful source of renewed relevance. Some of the most fulfilled people I know have deliberately pivoted from industry to industry, operator to advisor, practitioner to mentor, and full-time execution to selective contribution. The key is making those transitions while you still have options, not when the industry makes the decision for you.

The technology world can be unforgiving, especially to those who stay too long without evolving. But starting over doesn’t have an age limit. Purpose doesn’t come with an expiration date. If you’re still learning, still curious, and still adding value, staying in the game isn’t denial, it’s engagement.

I plan to keep working for as long as I love the problems I’m solving and as long as I’m willing to learn new domains. And most importantly, as long as I’m genuinely useful to the people and organizations I support.

But I also promise myself this: I will listen. I will keep asking hard questions of myself and looking in that mirror. And when my own midnight hour approaches, I hope I’ll remember Sanjay Khosla’s advice – and exit at five to twelve, with clarity, humility, and my reputation intact.

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This essay reflects my personal views and experiences and do not represent the views of my employer or any organization I am affiliated with.