Archive • Weekly Wisdom • Buttondown

Life moves through us.

October 11, 2025

I just got back from an overseas trip with a friend. When I travel, I’m reminded how little control I actually have and how freeing that can be. Flights get...

October 2, 2025

Courage doesn’t arrive all at once. It’s not something you can hoard, like jars of my mom’s strawberry preserves in her pantry, or wads of cash in the bank....

September 28, 2025

Leaders love to play the hero. We swoop in, cape flapping, to save the day. It feels noble. It feels productive. It feels like we’re proving our worth. And,...

September 25, 2025

My last post was about the myth of hustle. This one is about what comes next. Because life doesn’t end with hustle. There’s a better way. I don’t live...

The Myth of Hustle.

September 21, 2025

Hustle culture is seductive. Wake up earlier. Work later. Push harder. Stack the wins. Build the empire. It’s preached from stages, glorified on social...

Patterns tell the story.

September 18, 2025

We repeat what we don’t repair. Every leader I know has blind spots. Patterns they’ve built over time. Some of them help us survive. Some even help us...

The invisible weight.

September 14, 2025

Most leaders don’t realize how heavy it’s gotten until they stop moving. The late nights. The back-to-back calls. The decisions that pile up faster than you...

What We're Really Wired For.

September 11, 2025

One of the most underestimated parts of high performance isn’t strategy, skill, or discipline. It’s connection. Not networking. Not appearances. Not “how...

Feelings and Facts.

September 7, 2025

Emotions can feel like facts. True story. When I’m angry, it feels like someone must have done something wrong. When I feel disrespected, it feels like the...

The Danger of Autopilot.

September 2, 2025

I’ve learned the hard way that one of the biggest risks for leaders isn’t a lack of skill, resources, or even time. It’s cruising on autopilot. When you’ve...

5 Years from Now.

August 27, 2025

One of the biggest traps I’ve fallen into over the years is assuming that the version of me standing here today is the final draft. I know I’ll grow and...

Be the Solution.

August 20, 2025

I’ve been coming back to this mantra a lot lately: “Be the solution, not the problem.” Not because I’ve nailed it, honestly, it’s the opposite. I’ve had a...

Surviving bad days.

August 13, 2025

Disclosure: I’m not a medical doctor or a therapist and this is not medical advice. Just my personal experience. I am, however, a (mostly) normal human being...

When hustle becomes a cage.

There’s a moment, quiet and usually private, when we look around at our life and realize, this isn’t working anymore. Maybe the calendar’s packed. The bank...

August, sweet August.

Julius Caesar got July. Augustus Caesar got August. But, we get something better: an invitation. August is a threshold. Not quite summer, not quite fall. The...

Leading change.

You’ve made it through six weeks of hard questions.You’ve faced what’s changing in you.You’ve challenged the need for certainty.You’ve re-evaluated your...

Burn the map, keep the compass.

At some point in every leader’s journey, the plan stops working. The map you’ve been following (quarterly goals, hiring strategy, product roadmap) suddenly...

Your team is watching.

Here’s something most leaders underestimate during change: Your team is always watching. And, they believe what you do more than what you say. It doesn’t...

Stability ≠ Stagnation.

I’d like to kill a myth that keeps too many leaders I’ve met stuck: Stability and stagnation are not the same thing. Sometimes we act like they are.We think...

Who you take with you matters most.

Let’s talk about the people around you. When you’re leading through change, one of the hardest truths to face is this: Not everyone who's been part of your...

Certainty is a false god.

Most leaders I coach crave clarity.They want the roadmap, the plan, the playbook.They want to know. But here’s the hard truth about change: Clarity rarely...

Change behind the change.

Change isn’t what’s happening in your company.Change is what’s happening in you. Most leaders think change is external. New team, new product line, new...

Day Thirty: That's all folks.

The last 30 days of writing have reminded me of something simple but powerful: when you speak from the heart people lean in. I didn’t set out to inspire...

Day TwentyNine: Your best life.

Your best life isn’t out there somewhere, waiting to be discovered. It’s not hidden in a dream job, a perfect partner, or a five-year plan. It’s right here,...

Day TwentyEight: What it really takes.

Confidence doesn’t come first. Risk does. We wait around, hoping to feel ready, to feel sure, to feel confident enough. But, that moment rarely shows up on...

Day TwentySeven: An inside job.

Don’t be surprised if the breakthrough feels a lot like wandering. Like losing your bearings. Like standing in unfamiliar territory with nothing left to...

Day TwentySix: Break down or through?

We spend most of our lives trying to hold it together. We grip tightly to control, image, and certainty like they’re life rafts. Because in some ways, they...

Day TwentyFive: Who the?

People matter most. More than metrics. More than profit. More than the shiny vision deck or the strategic plan. At the end of the day, what we’re building,...

Day TwentyFour: Soul-full work.

Work is good for the soul. Not just for what it produces, but for what it reveals. It’s easy to think of work as a means to an end. Something we do to earn,...

Day TwentyThree: Your best days.

It’s easy to believe that the best parts of life are behind you. Especially, when you’re tired, when things haven’t gone according to plan, or when you’ve...

Day TwentyTwo: What it's really about.

Here’s the hard truth: it’s not about you. And, I don’t say that to diminish what you’re feeling. Nope, amigo. I say it to set you free. People carry so much...

Day TwentyOne: A fair fight.

Some fights aren’t loud. They don’t look like yelling or swinging or standing on a stage. Some fights are quiet. Hidden. Internal. Like fighting to believe...

Day Twenty: Size 13s.

I don’t have a clue what it’s like to be you. I don’t know what you’re carrying, what you’ve been through, or how heavy it’s been lately. But I know this,...

Day Nineteen: A little distance, please.

Setting boundaries isn’t about being cold or distant or difficult. It’s about being clear. It’s about telling the truth, first to ourselves, then to the...

Day Eighteen: Becoming a good friend.

It’s easy to talk about the kind of friends we want.Much harder to talk about the kind we’re becoming. We want people who are loyal. Who stick around when...

Day Seventeen: The unholy holy.

People will let you down. It’s not a matter of if, it’s when. And you’ll let them down, too. Not because you're heartless. Not because they’re careless. But,...

Day Sixteen: Leading from the center.

Leadership isn’t just strategy, it’s soul. Anyone can learn frameworks, build a playbook, stack wins. But, real leadership, the kind that endures, the kind...

Day Fifteen: Only good will come.

Let’s be honest, sometimes it doesn’t feel like anything is working. Our plans fall apart, the people disappear, the ground moves beneath us, and we’re left...

Day Fourteen: Falling.

We fall in love.And we fall into depression. Same language. Fall. As if there’s no choice in the matter. As if gravity has its own way with us. Here’s the...

Day Thirteen: Folks in the rearview.

Some friendships aren’t meant to last forever. That doesn’t mean they weren’t good, or right, or necessary. It just means we’ve outgrown them. Growth changes...

Day Twelve: Inner work.

We all want results. Growth. Peace. Purpose. Love. But here’s the truth: none of it lasts if we’re not willing to do the inner work. I’m talking about the...

Day Eleven: Managing the World.

Most of us are tired. Frustrated. Stuck.And we don’t always know why. But, if we’re honest, we can trace it back to a familiar loop: Fix. Judge. Compare. We...

Day Ten: A divine spark.

I reckon old Count Lev Tolstoy, the Russian author and aristocrat, was onto something when he wrote these words over a century ago: “People usually think...

Day Nine: Your personal soundtrack.

Thinking for yourself is a lost art. Most people don’t do it. They just mirror whoever’s loudest. Or, chase whatever sounds certain. But clarity doesn’t come...

Day Eight: Knowing.

There’s a version of you that already knows. Already knows how to walk through the season you’re in. Already knows how to let go without guilt.How to hold...

Day Seven: A holy ache.

Not every story ends the way we hoped. But every soul carries the spark of redemption. As long as we’re breathing, reinventing ourselves is possible. For...

Day Six: Change.

Almost half the people who reach out to me for coaching aren’t looking to get slightly better.They’re desperate for change.They’ve hit a wall.Something’s...

Day Five: This little light of mine.

There are no perfect people.We’re 0 for 107 billion on that one. Every single person you’ve ever met, even the ones who look like they have it all together,...

Day Four: Mirror-Moments.

“The kinder and more thoughtful a person is, the more kindness he can find in others.” Tolstoy nailed it. It’s not just true of kindness. It’s true of love....

Day Three: Adventurous.

My word for the year is explore. I chose it because I’ve tipped into the second half of life. And, what’s being asked of me now feels different. Less about...