I used to measure success by what I built.

Now I measure it by how I showed up.

That shift changed everything.

The First-Half Metrics

In the first half of my career, I measured success the way everyone told me to:

  • Title (Did I get promoted?)

  • Team size (How many people do I lead?)

  • Revenue (Did we hit the number?)

  • Projects shipped (What did we deliver?)

  • Recognition (Did people notice?)

These metrics made sense. They were clear. Measurable. Comparable.

And they worked - for a while.

I climbed. I achieved. I built things I'm proud of. By those metrics, I've succeeded.

Why Those Metrics Stop Working

Somewhere in my mid-40s, those metrics started feeling hollow.

Not wrong, exactly. Just... incomplete.

I'd hit the number, ship the project, get the recognition - and feel a strange emptiness afterward. A "what now?" that I couldn't quite name.

The metrics that drove me in my 30s weren't answering the questions I was asking in my 40s.

What does this all add up to?

What am I actually building here?

What will matter when I'm gone?

Achievement metrics can't answer those questions. They measure what you did. Not who you became. Not what you meant to people. Not what lasts.

The Second-Half Question

The question that's reshaping how I think about success is this:

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

Not on my LinkedIn profile. Not in my performance review. Not in my obituary even.

Just... at a dinner with former colleagues. When my name comes up. What do I want them to say?

Bad Answers vs. Good Answers

When I first asked myself this question, I noticed something uncomfortable.

The first answers that came to mind were achievement-focused:

"He shipped a lot of projects."

"He scaled the team to 500."

"He got promoted to VP."

Those aren't bad things. But they're not what I actually want people to remember.

When I pushed deeper, different answers emerged:

"He made me feel valued as a human."

"He helped me figure out my own path."

"He never forgot what it felt like to be where I was."

"He showed me it's okay to bring your whole self to work."

"He made me feel less alone."

Notice the difference?

The bad answers are about what I built.

The good answers are about how I showed up.

The Leader I Remember Most

The leader who shaped me most wasn't the one who shipped the biggest projects or had the most impressive title.

It was someone who took time to know me as a human. Who asked about my life, not just my work. Who made me feel like I mattered - not just my output.

I don't remember all the projects we shipped together. I remember how he treated me.

That's when I realized: legacy isn't about what you build. It's about how you make people feel.

And that's a completely different way of keeping score.

How to Start Living Toward Legacy

Legacy sounds like something you think about at the end of your career. A retirement consideration. A late-stage concern.

I don't think that's right.

Legacy is built in the small moments, every day. It's built in how you treat the person who reports to you. How you show up in meetings. How you respond when things go wrong.

It's not a someday thing. It's a today thing.

Here's how I'm trying to live toward legacy now:

1. Ask the question regularly.

I come back to "What do I want people to say about me in 20 years?" often. Not obsessively. But enough to keep it in front of me.

It reorients my priorities. When I'm tempted to optimize for achievement, it reminds me to optimize for impact.

2. Notice the gap.

When my answer to the question doesn't match how I'm actually living, I pay attention. That gap is information.

If I want people to say "He made me feel valued," but I'm rushing through 1-on-1s to get to "real work" - there's a gap. Time to adjust.

3. Choose presence over productivity.

Legacy isn't built by being efficient. It's built by being present.

The five extra minutes to really listen. The meeting where you put your phone away. The conversation where you're fully there.

Those moments compound. They're what people remember.

4. Remember what it felt like.

I try to remember what it felt like to be early in my career. Uncertain. Overlooked. Wondering if I belonged.

That memory keeps me grounded. It reminds me to treat people the way I wished someone had treated me.

The Shift

Here's the shift I'm trying to make:

From: What did I achieve today?

To: How did I show up today?

From: What did I build this quarter?

To: Who did I impact this quarter?

From: What will my resume say?

To: What will people say when I'm not in the room?

This isn't about abandoning achievement. I still want to build things that matter. I still want to be excellent at my work.

But achievement without legacy is hollow. And legacy is built in how you show up, not what you ship.

The Question for You

In 20 years, you'll be at a dinner with people you used to work with. Your name will come up.

What do you want them to say?

Not what they'll say about your title or your projects or your revenue numbers.

What will they say about YOU?

How you treated people. How you made them feel. What you modeled. What you stood for.

That's legacy.

And the time to build it is now.

-Michael

 

The 5 Questions for the Second Half launches February 26.