Years ago when I was leading an organization, one of the managers on my team asked for a one-on-one to talk about something he wasn't sure he was allowed to say out loud.

He told me he thought he was done climbing.

He was a good manager - respected, effective, doing meaningful work. He wasn't burned out. He wasn't unhappy. He wasn't heading for the door. But he had reached a level he genuinely liked, and when he looked at what came next - the bigger role, the wider scope, the pressure of leadership at the next tier - he didn't want it. He wasn't sure he was supposed to admit that. So he brought it to me, half asking my permission and half asking whether something was wrong with him.

He had come in ready to defend a position. In his mind, we were having a career-development conversation about whether he was still committed.

We weren't.

Here's what I've come to believe, from that conversation and from many like it since: most of the career-decision conversations executives are having are the wrong conversations.

Two frames dominate the way senior professionals think about their next move. The first is should I stay or should I go - the loyalty-versus-opportunity frame, weighed on some internal scale that never quite balances. The second is what should I do next - the options frame, where you line up the offers or the paths and try to reason from the outside in.

Both frames assume the decision-maker is a fixed point, evaluating options. Both skip the question that would actually make the decision resolvable.

The question underneath both of them is who am I becoming, and does this decision serve or refuse that?

I didn't ask my team member what he wanted to do next. I asked him what was important to him.

He told me about his family, and about a child at home with real needs and about wanting to be present for those needs in a way that a bigger role would have made harder. He told me about how he actually experienced pressure - not that he couldn't handle it, but that he didn't want to spend the next decade in a version of himself that was managing it constantly. He told me about the parts of his current job he loved and the parts that drained him, and it turned out the parts he loved were mostly about developing other people.

What was underneath his question wasn't a career problem. It was an identity that had gotten clearer than the org chart could account for.

Once he named that identity out loud, the what should I do question resolved in about ten minutes. He didn't need a new job. He needed his current role to bend around who he was - which turned out to be arrangeable. A set of responsibilities that let him keep growing without moving up, that gave him more of the work he loved and less of the work he didn't, that fit the shape of the life he was actually trying to live.

He stayed in that adjusted role for years. He was very good at it.

I've thought about that conversation a lot since I left that team. Because the mistake he almost made is the mistake most of us in the second half of career are being invited to make: to answer a what question before we've answered a who question. To treat a decision as a resolvable problem when what's actually happening is that our sense of ourselves is trying to catch up to what our lives are trying to become.

Discernment - the Catholic tradition's word for the interior work of figuring out what God is asking of you - has a specific ordering that matters here. Identity precedes activity. Being precedes doing. You don't start with the options and reason toward yourself. You start with yourself and reason toward the options. And when you do it in that order, decisions that felt stuck become simple, because the criteria have changed. You're no longer optimizing across a set of possibilities. You're asking a single question: does this fit the person I'm becoming, or does it require me to be someone else?

That's why so many executives get stuck in career transitions that shouldn't be complicated. They're pushing hard on a decision, and the decision isn't moving, because they're pushing on the wrong lever. The lever isn't the what. It's the who.

If you're sitting with a decision right now that won't resolve, the question probably isn't the one you think it is.

You're probably not stuck on whether to take the role. You're stuck on who you'd have to be to take it, and whether that person is someone you want to become.

Ask a different question. Not what should I do next. Not should I stay or should I go.

Ask who am I becoming, and does this decision serve or refuse that?

The answer, when you find it, tends to make the rest simple.

Coming next Tuesday: On why "who am I becoming?" is a harder question than it looks - and the two specific traps that make honest people answer it wrong. One shows up as an answer that sounds ambitious. The other shows up as an answer that sounds deep. Both of them stall the work before it starts.

What I'm Reading

Two books shaped how I think about this. Read together, they sit in productive tension with each other, and the tension is where the real work lives.

Working Identity: Unconventional Strategies for Reinventing Your Career (Herminia Ibarra) Ibarra is an INSEAD professor who has spent her career studying how executives actually navigate transitions - not how they think they will, but what happens in practice. Her core argument is that identity isn't something you find by thinking about it; it's something you discover by acting. You have to try on possible selves before you can know which one fits. It's the best professional-behavior lens I know on career reinvention, and it's a useful corrective to the temptation to over-think a transition into paralysis.

Let Your Life Speak: Listening for the Voice of Vocation (Parker J. Palmer) Palmer is Quaker, not Catholic, but his line - "Before I can tell my life what I want to do with it, I must listen to my life telling me who I am" - is the cleanest single-sentence statement of the argument this essay makes. He goes the opposite direction from Ibarra: less action, more listening; less experimentation, more attention to what's already trying to speak. Both are right. The productive tension between them is where a lot of real discernment actually lives.

One Ask

If this essay landed for you, I want to ask a favor.

Think of one person in your life who is sitting with the wrong question right now - someone stuck between staying and going. Someone lining up options that won't resolve. Someone who has told you, in so many words, that they can't figure out what to do next.

Forward this to them.

Not with a big pitch. Just: "This made me think of you. Might be worth ten minutes."

That's how this work grows - not through algorithms, but through one person handing it to another because they thought it might help. If Ad Alta Weekly ends up meaning something in the second half of your career, it will be because someone else forwarded it to you first. Pay that forward now, or subscribe here if someone just forwarded this to you.

In fieri. Ad alta. In the making. To the heights.

Michael

Ad Alta Weekly - vocational discernment and integrated leadership for the second half of the climb. Reach me anytime by replying to this email.