Everyone tells you what to do in your 20s and 30s.

Work hard. Build skills. Climb the ladder. Prove yourself. Provide for your family.

The path is clear. The metrics are obvious. The questions are straightforward: How do I get ahead? How do I succeed? How do I win?

Nobody prepares you for the questions that hit in your 40s.

The Questions I Expected

At 47, I thought I'd be asking questions like:

  • How do I plan for retirement?

  • Which college can we afford for the kids?

  • Should I push for one more promotion?

  • How do I protect what I've built?

Practical questions. Planning questions. Optimization questions.

And yes, I ask those too. Four sons heading toward college will do that.

The Questions I'm Actually Asking

But those aren't the questions keeping me up at night.

These are:

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?

Is this what I'm supposed to be doing with the second half of my life?

I didn't see these questions coming. Nobody warned me about them. There's no playbook for this.

In your 20s, everyone has advice. In your 40s, everyone assumes you've figured it out.

You haven't. You're just asking different questions now.

Why These Questions Feel Disorienting

The first-half questions have clear answers. Work harder. Make more money. Get promoted. Ship the project. Hit the number.

The second-half questions don't work like that.

What if success isn't the goal anymore? can't be solved with a strategy doc.

What do I want people to say about me in 20 years? can't be measured in a quarterly review.

Is this what I'm supposed to be doing? doesn't have a right answer you can look up.

These questions require a different kind of work. Not problem-solving. Sense-making. Not optimization. Discernment.

And most of us were never taught how to do that.

We were taught to climb. Not to ask whether we're on the right mountain.

The Difference Between a Crisis and a Call

When these questions first hit me, I thought something was wrong.

Am I having a midlife crisis? Am I ungrateful? Am I just bored?

I've since learned to see it differently.

A crisis is when something breaks and you're scrambling to fix it.

A calling is when something deeper is trying to get your attention.

They can feel similar on the surface. Both involve disruption. Both involve uncertainty. Both make you question what you thought you knew.

But the energy is different.

Crisis energy is frantic, desperate, reactive. You're running FROM something.

Calling energy is persistent, patient, directional. You're being drawn TOWARD something.

The questions I'm asking don't feel like crisis. They feel like calling.

Not a call to burn everything down. Not a call to quit my job and move to a beach.

A call to pay attention. To build something on the side. To honor where I am while preparing for what's next.

What I'm Learning About Sitting With Questions

My instinct—trained by 25 years of problem-solving—is to answer questions as quickly as possible.

Identify the problem. Analyze the options. Make a decision. Move on.

But these questions don't work that way.

What do I want people to say about me in 20 years? isn't a problem to solve. It's a question to live with.

What if success isn't the goal anymore? doesn't need a quick answer. It needs time. Reflection. Conversation.

I'm learning to sit with questions instead of rushing to answers.

To let them work on me instead of trying to work on them.

To trust that clarity comes from living the questions, not just thinking about them.

This is uncomfortable for someone who's built a career on having answers. But I think it's the right kind of uncomfortable.

The Questions Are the Point

Here's what I'm starting to believe:

The questions you're asking in your 40s aren't a sign that something's wrong.

They're a sign that something's right.

They're a sign that you're paying attention. That you're not just drifting through the second half on autopilot. That you're taking seriously the question of what your life is actually for.

The first half is about building a life.

The second half is about asking whether it's the right life—and having the courage to adjust if it's not.

That's not a crisis. That's wisdom.

You're Not Alone

If you're asking questions like these, I want you to know: you're not alone.

I'm asking them too. And based on the conversations I've been having, a lot of people our age are asking them.

We just don't talk about it. Because we're supposed to have it figured out by now.

We don't.

And maybe that's okay.

Maybe the second half isn't about having answers. Maybe it's about having the courage to ask better questions.

I'm building a guide called "The 5 Questions for the Second Half." It's a framework for sitting with these questions intentionally—not to answer them quickly, but to let them shape what comes next.

It launches February 26. I'll send it to you free if you sign up below.

In the meantime, let me ask you:

What questions are you asking that nobody warned you about?

-Michael

The 5 Questions for the Second Half launches February 26.