The Activated Leader™ | Issue #51

In this issue:

Before anything else

Most leaders don't need more information.

They need a stronger relationship with their own judgment.

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I want to tell you something that happened in Barcelona this week.

My brother and I were walking through the city. No agenda. Morning light. Coffee in hand.

And I kept catching my dad in him.

In his laugh. In the way he gestured when something surprised him. In a particular expression I hadn't seen on anyone's face since we lost him.

My dad who's gone.

And instead of just being there with all of that, instead of letting it matter the way it deserved to, my brain handed me a to-do list.

Client follow-ups. Revenue projections. Is the business growing fast enough. What if the money runs out.

I've been a coach long enough to know exactly what that was.

That wasn't ambition. That wasn't responsibility.

That was armor.

Achievement as Armor

High achievers don't talk about this enough, partly because it's hard to name something that's also genuinely a superpower.

The drive is real. The results are real. The identity you built around producing is not fake.

But for a lot of us, underneath all of that, is something we've never said out loud:

Work is the place where I have control.

And life, real life, the grief and the love and the mortality and the uncertainty of it, doesn't give you that.

So we do what we're good at. We optimize. We stay busy. We produce and achieve and build.

And we call it drive.

Because that's the most socially acceptable name for it.

Our entire culture has infrastructure for this. Mentors, frameworks, goals with metrics attached. There are industries built around helping you achieve more.

There is almost no infrastructure for what you do when you've achieved it.

Where mine came from

I grew up the youngest of eleven. Money was always scarce, not as an abstraction, as a daily reality.

In my early twenties I was sleeping on an air mattress, eating peanut butter and Earl Grey tea, neither need refrigeration, building a business from nothing.

I learned that work was safety. That producing meant surviving. That if I stopped moving, things fell apart.

That was true. For then.

I wrote an affirmation card. Read it every day. Ten grand a month. Car of my dreams. House of my dreams.

I did every single thing I said I was going to do.

Retirement funded. Kids' college paid for. A career at Google and Microsoft and then a practice I built entirely on my own terms.

That version of me on the air mattress didn't need to be silenced.

She needed to be updated.

The scarcity she was protecting against isn't the reality anymore. But that nervous system didn't get the memo.

So when I spend money on a trip, or slow down for a week, or let something matter more than my output, it fires.

And it hands me a to-do list in the middle of Barcelona.

What I was actually running from

Here's what I've been sitting with since that walk.

The to-do list wasn't about the business.

The to-do list was about how much that moment mattered.

Because if I let it fully land, if I let in what it meant to be with my brother, catching my dad in his face, feeling time do what time does, that's a lot to hold.

And holding it doesn't give you anywhere to put the energy.

So the noise fires up. The productivity anxiety. The money worry. The is-this-responsible spiral.

Easier to feel guilty about not working than to feel the weight of grief.

Easier to feel anxious about revenue than to feel the brevity of the moment you're actually in.

The self-judgment wasn't accountability.

It was an escape hatch.

I think this is what's underneath a lot of the work I do with leaders. Not the strategy pieces. Not the career planning. But this:

What are you using your achievement to avoid feeling?

What opened up when I stopped

I put the phone down. I stayed with it.

Not perfectly. But enough.

And here's what was waiting on the other side of the armor:

My life looks like a movie.

That's not a brag. It's a recognition I hadn't let myself have.

The affirmation card I wrote at 22, I have that life and then some. And I'm in Barcelona. And my dad is somehow there in the way my brother laughs.

When the noise finally went quiet, that's what was there.

Not a crisis. Not emptiness.

The full weight of a life that is genuinely good.

The gnawing that sends high performers back to the desk, back to the hustle, back to the next milestone, that's not ambition.

That's withdrawal from a very familiar substance.

It served us. It got us here.

The work now isn't rejecting it.

It's knowing when it's running the show versus when it's serving you.

And building, slowly, the capacity to let the important things be as important as they actually are.

What's Activating Me This Week

Listen

Tim Ferriss's interview with BJ Miller, the palliative care physician, "The man who studied 1000 deaths to learn how to live".

The question he asks his patients about what they want their last chapter to look like is the same question every high achiever should ask themselves now, while there's still room to answer it differently.

Try

Once this week, just once, when the productivity anxiety fires, don't redirect it.

Ask it:

What am I trying not to feel right now?

You don't have to fix the answer.

Just know what it is.

Your Activation This Week

Time doesn't wait for the right quarter.

The people you love are aging whether your revenue dashboard is green or not.

The question I'm carrying out of Barcelona isn't about my business.

It's simpler and harder than that.

What would I do with this week if I trusted that I've already done enough to deserve it?

Sit with that one.

Until next Saturday,

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