A newsletter for executives, founders, and senior leaders navigating the second half of career - from Michael Halbrook, deacon and builder.

Welcome to Ad Alta Weekly.

This is the first issue of what I'm committing to as a weekly perspective on vocational discernment, career transition, and integrated leadership.

Every Tuesday morning, you'll get one essay - substantive but not exhausting, professional but not corporate-generic, informed by my Catholic faith but written for anyone thinking seriously about what their work is actually for.

Ad Alta is Latin for "to the heights." The name is from Saint Pier Giorgio Frassati's Verso l'alto - his signature exhortation, written on his last photograph before his death at twenty-four. He was canonized last September, alongside Saint Carlo Acutis, during the Jubilee of Youth. Frassati wasn't calling people away from ordinary life. He was calling them to ascend through it. That's what this newsletter is about.

I'm glad you're here. Let's begin.

The Next Climb

I've spent this year publicly telling a story about integration.

The story goes something like this: For nearly eighteen years, I built at Adobe - and for a dozen years before that, in other roles in media, marketing, and tech. For the last several months, alongside that day job, I've also been building: a Catholic prayer formation company with my wife, a leadership perspective for builders in transition, a serial novel that launched on Easter Sunday, and a deacon's desk for essays and homilies. In May, I left Adobe to bring all of it under one roof. 

In the language I've been using: I'm not pivoting. I'm integrating.

I still believe that framing. But I've noticed something worth naming, six weeks into this new arrangement:

Integration is not one decision. It's an ongoing climb.

I thought that when I left Adobe, the hard work of integration was mostly done. The professional identity had come home. The vocational threads had converged. All that remained was execution.

I was wrong.

The integration I named on May 8 was real. But it was a first summit, not the mountain. Beneath it, I've discovered, there's more territory. And the territory ahead isn't about arriving at integration. It's about continuing to lean bravely into it.

Here's an example:

Last week, our son Matthew left for Air Force Basic Training. On the morning of his departure, before we drove to the airport, our family gathered in the kitchen. Two of our other sons, Andrew and Joseph, stood with Suzanne and me as I prayed a prayer for a departing service member and a blessing over Matthew.

I've prayed blessings over hundreds of people as a deacon - over strangers at the parish, over friends leaving on pilgrimage, over families about to move away. It's a small liturgical act, done thousands of times a day by clergy around the world.

But this time it was my son, leaving for a major step into adulthood.

And in that moment, I was not a deacon doing a blessing while also being a father saying goodbye. I was both, fully, at once. The prayer I said was the Church's prayer, but I was also the father praying his own words underneath it - please protect him, please bring him home safely, please let him become the man he is meant to become. Both prayers were one prayer. Both roles were one role. There was no seam.

I don't think I could have done that even a few years ago. Not because I wasn't a father then, and not because I wasn't a deacon - I was already both. But because for years I lived with an invisible partition between them. Deacon Michael was one person. Dad Michael was another. Adobe Michael was a third. Each showed up when it was his turn.

Last week in the kitchen, none of them took turns. All of them stood there together with Matthew. And what I felt was not the strain of holding multiple selves at once. What I felt was relief.

Integration is not a state you achieve. It's a climb you keep making.

For years, I caught myself still feeling like I needed to hide parts of me from certain audiences, wanting to present a more polished self professionally than I actually am, wanting to leave the diaconate at the office door when I show up to certain meetings, wanting to leave the professional at home when I show up in the sanctuary, wanting to keep the writing separate because it feels vulnerable to admit that I'm working on a novel and a consulting proposal and a Sunday homily on the same day.

Each of those temptations is a small refusal to climb.

Frassati's verso l'alto was not about escape. He was a mountaineer - he loved the adventures outdoors with his friends. He knew that climbing is done through terrain, not around it. When he called his friends to the heights, he wasn't calling them out of their ordinary lives. He was calling them deeper into them - deeper into the friendships, the work, the mountains they were already on, but now with their eyes lifted.

For those of us in the second half of career and life, this is the invitation that keeps deepening: not to escape what we have built, but to climb higher through it.

Higher, not by adding more work. Not by accumulating more titles or ventures or platforms. But by refusing to keep parts of ourselves separate. By letting the leader and the parent and the person of faith all show up in the same meeting, in the same conversation, in the same email, in the same blessing. By being willing to be seen as one integrated person, even when the culture around us keeps insisting that professional and personal and spiritual should be different files on the desktop.

The next climb, I'm learning, is further leaning bravely into the integration.

Every time I do it - every time I bring more of myself into a room where I would have brought less - I feel something loosen. I also feel something risk. Those two feelings are related. What loosens is the burden of managing multiple selves. What risks is the possibility that showing up whole will cost me something with someone who preferred the partial version.

But the alternative is a smaller life. And I don't think any of us actually wants that.

If you're reading this, you're probably somewhere in your own version of this climb. Some transition, some redirection, some inner sense that the next thing being asked of you is not smaller but more.

Verso l'alto. Not away from what you have. Through it. And onward.

Coming next Tuesday: An essay on the specific tension between career discernment and identity - and why the two conversations most executives are having about their next chapter are the wrong two conversations.

If this landed with you, please forward it to someone in transition. If someone forwarded it to you, subscribe here.

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

Michael