I've spent 30 years leading in media, marketing, and tech. Now I'm building something completely different.

Here's why.

The Setup

I’ve led teams of 100 people to hundreds of people at Adobe. I've been there for almost two decades, minus an 18-month detour that taught me more than I expected (more on that another time).

By most measures, I've succeeded.

I've led teams through 3 market crashes. Survived 3 acquisitions in 12 months. Built systems that are still running years after I moved on. Hired hundreds of people, developed leaders, shipped projects that mattered.

I have four sons, a marriage of 21 years to Suzanne, and a life that looks - from the outside - like it's working.

And it is working. I'm not writing this from burnout or crisis or desperation.

But somewhere in the back half of my 40s, the questions changed.

The Shift

I started asking questions I didn't expect to be asking at this stage:

What if the path forward isn't up?

What if success isn't the goal anymore?

What would I do if money wasn't a factor?

What do I want people to say about me in 20 years?

These aren't the questions I thought I'd be wrestling with at 47. I expected to be thinking about retirement planning, kids' colleges, maybe a promotion or two before winding down.

Instead, I'm thinking about calling. About legacy. About what the second half of life is actually for.

And I started building things.

Not for work. Not because anyone asked me to. But because I couldn't NOT build them.

Deacon Life - a community for Catholic deacons.

Emmaus Disciples - spiritual formation and community for people on the journey.

And now this: Lead & Keep.

The Tension

Here's what I want to be clear about: I'm not unhappy. I'm not burned out. I'm not running away from something broken.

But I'm also not sure I'm supposed to be doing the same thing for the next 20 years.

I'm in transition. Still leading my team - fully present, not checked out. But also building toward something else. Something that feels less like climbing and more like calling.

It's a strange place to be. Successful but questioning. Grateful but restless. Honoring where I am while building where I'm going.

If you've never felt this tension, this space might not be for you.

But if you have - if you're somewhere in the middle of a similar wrestling match - then welcome. You're in the right place.

Why "Lead & Keep"

The name comes from a question I kept asking myself:

Can you lead successfully AND keep what matters?

Because somewhere along the way, we got sold a false choice.

Drive results OR care about your people. Climb the ladder OR stay true to yourself. Build your career OR build your life.

I've watched leaders choose one side and lose the other. I've watched people optimize for success and end up empty. I've watched people protect their humanity and get passed over.

And I've spent 30 years trying to do both. Not perfectly. But intentionally.

Lead & Keep is about that "&."

  • Lead successfully AND keep your people (not burn through them)

  • Lead successfully AND keep yourself (not lose yourself to the role)

  • Lead successfully AND keep your integrity (not compromise to climb)

  • Lead successfully AND keep building toward what's next (not get stuck)

It's possible. Hard, but possible.

What This Space Is

Lead and Keep is for leaders in the second half who are asking similar questions.

It's NOT a "quit your job and follow your passion" space. That advice is easy to give and hard to live - especially when you have a mortgage, four kids, and people depending on you.

It IS a "how do I honor where I am while building where I'm going" space.

It's honest. No bull. Still figuring it out.

I'm not writing from the other side of some transformation. I'm writing from the middle of it. Which means I might be wrong about some things. I'll definitely be learning as I go.

But I think there's value in that. Most leadership content comes from people who've already "made it" and are looking back. This is different. This is real-time. This is "here's what I'm learning while I'm learning it."

What's Coming

Over the next several weeks, I'll be posting about the questions I'm wrestling with:

  • The questions nobody warns you about in your 40s

  • Why "too late" is usually a lie

  • What you build when nobody's watching

  • The money question that changed everything for me

  • Why legacy matters more than achievement in the second half

I'm also building a guide called "The 5 Questions for the Second Half." It's a framework for leaders who are successful but questioning - a way to sit with the questions that matter instead of rushing past them.

It launches February 26 (my 48th birthday). Sign up below if you want to get it free when it drops.

Eventually, I'm building a cohort - a small group of leaders navigating this transition together. Not a course. A community. More on that later.

If This Resonates

If you're successful but questioning...

If you're building something on the side that nobody asked you to build...

If you're wondering what the second half of life is supposed to look like...

You're not alone. And the questions you're asking aren't a crisis.

They're a call.

Let's figure it out together.

- Michael

The 5 Questions for the Second Half launches February 26. Sign up to get it free.