During one of my morning deep work blocks, I was at my computer, wrestling with the same question I kept circling back often in those early months of An Intentional Age. What was the right approach for this thing I wanted to build? Some blend of strengths assessments, decades of activating and maximizing ideas and people, and a dream I hadn’t quite said out loud yet: to actually live the way I kept telling other people to strive towards.
So I went looking through much of what I’d written in the past, trying to figure out what An Intentional Age actually was. Not what I wanted it to be. What it already was, buried in a decade of proposals, half-finished pieces, and drafts I’d started and left somewhere in the middle.
I wasn’t looking for inspiration. I was looking for evidence. Which of these pieces actually carried the thing I was trying to build now, and which ones were just noise from a version of me still figuring out the destinations and journeys.
It’s a strange exercise, reading yourself at a distance. Some of it felt like eavesdropping on a stranger who happened to share my name. Some of it felt uncomfortably familiar, the same worry wearing a different outfit, showing up again a decade later as if no time had passed at all.
Most of it didn’t survive the read. Good sentences, wrong century. But one article kept surfacing, insisting on itself in a way the others didn’t.
I’d written it at fifty-three, for a venture called Aging Outside the Lines that never quite found its market footing. The piece was titled “Transition to Purposeful Work,” and it was about finding your mission after a career ends the way you expected it to keep going.
Reading it again, I didn’t recognize the man who wrote it. It was honest, well-constructed, sincere. What struck me was what it leaned on.
Five other people’s frameworks, cited one after another. Covey. Rick Warren. Sinek. Two more. My own contribution to five hundred words about finding your purpose was, essentially: pick one of these that speaks to you, and do the work. I wasn’t offering my own read of the crossroads I was standing at. I was pointing at other experts’ maps and hoping one of them fit.
The article ended with a promise I hadn’t earned yet: “More on this story and the paths that emerge, as you learn about me.” I remember writing that line and meaning it completely. I also remember, underneath meaning it, a quiet suspicion that I didn’t yet have the story worth telling. So I borrowed five that did.
Years passed. Real leadership roles, ones I earned and grew into, but never a venture that was fully mine to build. Then An Intentional Age. An actual founder’s journey, this one, with real scar tissue behind it instead of a mission statement borrowed from a bookshelf.
When I came back to that old piece to rebuild it for An Intentional Age, the borrowed frameworks were suddenly visible for exactly what they were. Scaffolding. A voice standing behind other voices because it wasn’t ready to stand on its own yet.
Here’s why I’m telling you this now, instead of just quietly rewriting the piece months ago and moving on.
Harvard Business Review just published something by David Lancefield naming a risk facing every leader who has folded AI into how they work. You can hand off your judgment, your voice, your presence, he argues, in small transfers that each seem inconsequential on their own. Then one day you look up, and the thinking in the room isn’t quite yours anymore.
His example is a CEO reviewing a town hall speech her team had drafted with AI, built from her own past remarks. Technically sound. Measured. Safe. And not actually hers, because it reflected the version of her the company already knew, rather than responding to what this particular difficult quarter actually required.
Lancefield breaks this down into four plain questions leaders can ask about any piece of work in front of them.
Does this decision carry real stakes, the kind where your judgment on trade-offs and consequences has to lead. Does this communication carry your intent and your standards, the kind where AI can help you organize it but shouldn't decide what you actually mean. Does this moment need your physical, human presence, the kind no digest or summary can substitute for. Or is this simply repeatable, low-stakes work, the kind that frees up your energy for the other three.
Most days, most leaders never ask themselves these questions at all. They just move through whatever’s in front of them, and the categories blur together without anyone noticing the difference.
I did the same thing at fifty-three. I just used a bookshelf instead of a chatbot.
This is the pattern I watch for now in the executives I advise, and it rarely looks dramatic when it’s happening.
A leadership team walks into a quarterly review having read an AI-generated summary of the numbers in advance, and whatever the summary chose to emphasize becomes the lens the whole room reasons through, before anyone checks it against what they actually know about the business.\.
Somewhere else, a difficult message goes out under a name and a title, built from an outline that sounded confident and reasonable, and it lands flat, because people can always tell when words didn’t cost the sender anything to write.
And sometimes it isn’t a decision or a message at all. It’s contact. A leader stops sitting in on the unscripted conversations and starts reading only the polished recap afterward, and slowly the recap becomes the whole relationship. The hesitation before an answer, the comment made once and never repeated, quietly disappears, because no digest was ever built to capture it.
Neither failure looks like a crisis in the moment. Both are the same quiet transfer, just wearing different clothes. Something that used to require your judgment starts running on autopilot, and nobody notices the handoff because nothing goes visibly wrong right away.
The tool changes. The habit underneath it doesn’t. Reach for whatever already sounds authoritative, because trusting your own unfinished read of the situation feels too exposed.
The tool changes. The habit underneath it doesn't.
For me it wasn’t really about the frameworks themselves — it ran underneath real leadership roles, starting at Bose in the mid-nineties and continuing through Microsoft and various SMBs, roles I earned and worked hard to keep growing within.
Even there, the same quiet habit kept showing up. Deferring to whoever already sounded more authoritative. An executive’s read on a decision that was actually mine to make. An established process, a framework someone more credentialed had already written down, instead of my own. The judgment was there. It always was. Trusting it out loud just felt riskier than borrowing someone else’s version instead.
That belief never fully left. It got better at hiding, learning to wear more respectable clothes as I climbed, until it stopped sounding like doubt at all and started sounding like professionalism.
I don’t think this is only a story about me, or even only a story about leadership. Whatever chapter you’re standing in right now, wherever the doubt shows up for you, the mechanism is usually the same. Something in you decides you’re not quite there yet, and goes looking for something else, anything else, safer and already-approved, to stand behind instead of your own read of the moment. I find it at the highest levels, in the honest exchange with those executives I coach.
At fifty-three, one of its better disguises was within my marriage. I told myself I was being responsible. Protecting Julie, protecting our financial security, choosing the more sensible path over the riskier one.
Some of that was completely true, and still is. Julie and our financial stability were both real considerations, both worth protecting, and I don’t think any less of myself for weighing them carefully.
But the doubt used that truth as cover. It wasn’t really about her, or about financial security in general. It was about whether I believed I had anything of my own worth saying yet, dressed up as caution so it would sound like wisdom instead of a lapse in courage.
There’s a study Lancefield cites in that same piece. The people who leaned hardest on AI to draft their essays weren’t writing worse work. They just didn’t feel like it was theirs anymore, because the thinking that shaped it had happened somewhere other than in their own heads.
That’s the part that tracked for me rereading my own fifty-three-year-old writing. It wasn’t shame, exactly — it was distance. The specific, strange feeling of reading something clearly signed with my name, in a voice I couldn’t quite locate as mine. No AI involved, but yet the same separation of self. Old me from new me.
If you’re building something right now, a company, a keynote, a hard conversation you’ve been putting off for longer than you’d like to admit, here’s the one thing I’d actually ask you to try before your next high-stakes call or draft.
Before you bring in AI, or a colleague, or anyone else, write down your own diagnosis first. What you actually think is going on, and why. It doesn’t have to be polished. A few honest sentences is enough.
Then hand it over and ask whoever, or whatever, you’re working with to challenge it, not to write it for you. Let your read get tested. Don’t let it get replaced before you’ve had the chance to trust it. I am doing that with my writing at this moment.
Ask yourself the real question underneath Lancefield’s four categories. Is this a moment where my judgment, my voice, or my presence actually needs to lead. If the honest answer is yes, do the first rough version yourself before anyone or anything else touches it. If the honest answer is no, hand it off completely, and spend the time you just freed up on the work that genuinely needed you.
I finally kept the promise I made at fifty-three. It took a decade longer than I expected it to, and for most of that decade I would have told you I was simply busy building a career, not quietly waiting to believe I’d earned the right to say what I actually thought.
Every bit of that decade turned out to be the material the earlier version of me didn’t have yet, and couldn’t have borrowed from anyone else no matter how many books he cited.
What have you filed under not ready yet, that you might actually be ready to say?