I’m getting ready for my 50-year high school reunion. Yes, you read that right, 50 years!

There is nothing quite like a high school reunion to remind you how quickly life moves, and how generous time can be in editing our memories. The victories get a little bigger, the embarrassing moments get a little funnier. Did I really dress like that?

And apparently, according to some of my friends, we were all much better athletes than our coaches realized.

Sadly, after five decades, none of us was called up to play in any professional sports league. As for me, I could have made it to the NBA if they’d have just lowered the hoop a foot! Alas, I’m beginning to think my pro sports dreams may be fading. Maybe there’s still a senior circuit?

Recently, as the reunion approached, I had the chance to share Sunday brunch with three old friends from my high school days. We hadn’t seen one another in a decade. Life had simply done what it does. Careers took us in different directions. Families grew. Calendars filled up. Years slipped by. We sort of stayed in touch, but not really.

Then a few weeks ago we sat down together for a meal and a long overdue catch-up. Within minutes it felt as though we had been together just the week before. It was great.

The stories came quickly, and so did the laughter. One memory unlocked another. Names we hadn’t spoken in years suddenly popped into our minds. Teachers, teammates, old flames, and questionable fashion choices all made appearances. Anyone remember bell-bottoms? Hairstyles were mostly discussed in the past tense, at least for me.

There was just as much laughter as there had been all those years ago, and just as many good feelings. I loved every minute.

That is the remarkable thing about old friends. They remember you before you had any titles, accomplishments, disappointments, or adult responsibilities. They knew you while you were still trying to figure out who you were, usually while they were trying to figure out the same thing themselves. Old friends remember the unfinished version of you, and now they get to know the slightly more finished version.

Somehow, when you are together again with old friends, all the years between then and now evaporate. You don’t have to explain every chapter in between. They know where the story began, and there is something wonderfully comforting about that.

There is something almost sacred about sharing a meal with people who have known you for most of your life. Yes, phone calls are wonderful and text messages can keep us connected. Social media lets us follow one another’s families, travels, and birthdays. But none of those things can replace being in the same room, sitting across the table, looking into each other’s faces, and hearing the laughter rather than reading “LOL” on a screen. There is a warmth that only comes from being together. It’s magical.

I see the same thing in my work. My coauthor Adrian Gostick and I spend much of our lives speaking to companies that bring their people together, sometimes flying them in from all over the world. You could argue that much of what happens at these meetings could be delivered over Zoom or Teams. But that misses the point. We don’t bring people together simply to exchange information. We bring them together to build relationships.

I’ve watched in these meetings as colleagues who knew each other mostly as faces in little boxes share a meal, laugh together, tell stories, work through issues, and begin to see each other as people rather than job titles. Trust grows differently when people are in the same room. So does belonging. And when people get to know and trust one another, they collaborate better.

That’s why I believe gathering in person is an investment in the relationships that make cultures work.

Back at the brunch table with my old friends, I felt enormously grateful to be together. We had all lived full lives. We had children and grandchildren and all had experienced joys and disappointments, successes and setbacks, weddings and funerals, good health and difficult days. Over 50 years, just about everything had happened that can happen to humans, and still, there we were, a bunch of old friends having a good time. Still able to see the young people we had once been inside the somewhat older people we are now.

I left wondering why we had we let ten years go by. It wasn’t because we didn’t care about one another. Quite the opposite. I think it happened because we assumed the friendship would always be there. That’s a mistake many of us make with relationships that matter the most.

We tend to those types of relationships for granted precisely because they are strong. There is no crisis demanding our attention. No meeting invitation popping up on the calendar. We know our old friends will understand if we don’t call this week or next. We think we’ll reconnect when we have more time, but life rarely gives us more free time. And, suddenly, ten years have gone by.

Relationships rarely disappear because of one dramatic moment. Sometimes they simply fade because there weren’t enough moments.

Friendships need care. Gratitude needs action, and sometimes it needs a place on the calendar.

My 50-year reunion reminded me that the great gifts of life are rarely things, they are people. They knew us “back when,” cheered for us, and are still happy to see us now.

No one in my class became a professional athlete, as we might have dreamed at the time, and most of us don’t have as much hair as we once did. But we have something far more valuable: great memories and friendships that have lasted across half a century.

That is something I don’t want to take for granted again.

So, please, take my advice. If you feel thankful to someone, call them. Invite them to lunch. Write a note. Make a trip to see them. Sit around a table and tell stories again. Who knows you may discover that one of your friends has joined a bagpipe band! You may not be able to recover all the years that have passed, but you can make sure that you don’t let another ten slip away. That’s the key. Just do it!

You may discover that the friendship wasn’t lost at all. It was simply waiting for you to come back to the table.

Love + gratitude,

I like to be a busy person. I’m the kind who used to answer, “How are you?” with something like, “Busy, and loving it!” as if that were an accomplishment instead of a diagnosis.

I was always doing something, always moving to the next task, always assuming my body would show up and do whatever I asked of it, no questions asked, like a reliable but underappreciated employee.

Then the doctor told me I needed shoulder replacement surgery, and that loyal, hard-working employee filed for a leave of absence.

For the longest time after surgery, I couldn’t type without looking like I was defusing a bomb, hunt-and-pecking at a keyboard. I couldn’t write with my right hand. I tried writing with my left hand, and it looked like the work of a five-year-old who had done it in the backseat of a moving Jeep … while being chased by a T-Rex.

Putting on a shirt became a full production, complete with grunting sound effects and my wife rushing in to see if I was having a stroke. Even buckling a belt, something I’d done thousands of times without a single conscious thought, suddenly required the kind of concentration I used to reserve for parallel parking in Manhattan.

The recovery process began to feel like a prescription. Not the kind you pick up at the pharmacy in a nice little paper bag with a receipt, but more the kind life writes for you when it decides you need to grow, whether you asked for it or not.

My prescription read:

Take one large dose of patience several times daily.

Complaining will not improve results.

Refills(Maybe).

We’ve been told that patience is a virtue. When I heard that in the past, I nodded along like you do with all things you have no intention of actually practicing, like flossing daily or reading the terms and conditions on your insurance policy. Virtues were things other people needed to work on. Patience, to me, sounded like a nice hobby for those with lots of time on their hands. That was, until I had no choice. After surgery my body simply would not move at the speed my mind wanted it to, no matter how firmly I asked it to.

Then I began to understand what real patience was all about.

Here’s what I didn’t expect: the amount of energy that healing takes. Not effort in the way we usually think of it. I wasn’t lifting weights, running, or pushing through workouts. I was mostly sitting on the couch, icing my shoulder, doing what appeared to the naked eye to be absolutely nothing. But my body was working overtime beneath the surface, rebuilding, repairing, knitting things back together. It turns out that takes real energy.

I’d finish a short walk down the hallway and need a nap. Not a hike, mind you, I’m talking a stroll down the hall and I felt like I’d just run a marathon. Nobody warns you about that part of healing. We don’t think of healing as labor, but it is. Quiet, invisible, thoroughly exhausting labor that somehow still leaves you feeling like you did nothing all day.

Somewhere in the middle of all that slowness, something shifted in my thinking about my body. I stopped taking small things for granted. Simply being able to write a few lines in my journal again felt like an achievement worthy of a small parade. Getting a shirt over my head without wincing felt like sticking a gold-medal landing at the Olympics. Things I had done a million times in my life, without a second of gratitude, I suddenly noticed, really noticed, every single time.

It was as if I was handed a brand-new appreciation for my right arm. My dominant hand, as it turns out, is a really important arm. No offense to my left; it’s doing its best.

And then, there came part of healing I really wasn’t prepared for: an outpouring of friendship and love. Flowers showed up at the door. Friends dropped off brownies and food baskets, get-well balloons, and even origami carrots, one of my favorites! Notes of encouragement arrived asking, “How are you doing?” and “How’s the rehab?” They came from people I hadn’t heard from in a while and from people I talk with often. When life forces you to slow down, you suddenly have time to notice things you might otherwise hurry past, and I found myself noticing just how many good people I have in my corner.

That may be the real gift hidden inside this whole patience prescription. When you can’t do things for yourself, you are reminded how much other people are willing to do for you. I have always considered myself a grateful guy, but there is something humbling about being on the receiving end of so much kindness. It made me realize that I am one of the luckiest people on the planet.

The experience also gave me a new and humbling kind of respect for people who live with the use of only one arm through war, illness, accident, or circumstances of birth, not for the twelve weeks my surgeon promised me, but permanently. These folks wake up every day and figure out daily life: buttoning a shirt, tying a shoe, carrying a bag of groceries, living their life. I had only a temporary glimpse of a fraction of what they navigate as a matter of course, and it left me in awe of what the human spirit is capable of adapting to.

Looking back now, I wouldn’t have chosen this prescription. Given the choice, I’d have picked almost any other virtue to work on. Generosity, maybe, or punctuality, something I could practice with both hands. But I’m not sure I would have learned such a valuable lesson any other way.

Patience, it turns out, is not simply a personality trait some people are lucky enough to be born with. I certainly wasn’t. But I found it is something that can be built, even against your will, while you’re frustrated and one-handed and fumbling with a belt buckle at seven in the morning. And what it can leave behind is a kind of gratitude that’s hard to manufacture any other way.

I’m grateful for the small things I never thought to appreciate before. I’m grateful for a body that is doing the slow, invisible work of healing. Most of all, I’m grateful for the people who showed up to help.

So here’s what I’m asking you to consider this week: Has life ever prescribed you a dose of patience you didn’t want but ended up needing? What did slowing down force you to notice that you might otherwise have missed? I’d love to hear about your own “patience prescription” moment. I have a feeling I’m not the only one who’s been handed this particular medicine.

With gratitude,

A wonderful CEO I worked for once reminded me that I stood on the shoulders of giants.

His point: I was where I was because of the many people who had poured knowledge and caring into me over the years: mentors, friends, teachers, and family members. These people not only encouraged me, but sacrificed and paved the way so I could go further and faster than they ever had.

Boy was he right.

I’ve thought about that a lot over the years. It reminds me that every one of us is the culmination of many influences. In fact, as the names of my own giants run through my mind right now, I can see their faces clearly and feel deeply grateful for what they did for me.

I hope, as you read this, people from your life are coming to mind. Perhaps a teacher, a parent, a coach, a spiritual leader... and I’ll bet a co-worker or a boss is on that list. I hope just thinking about them brings a smile to your face, warms your heart, and fills you with gratitude.

My parents have been gone for many years now, but they were the two biggest giants in my life: my father, John Dalton Elton, and his beautiful, talented wife, Irene Tanner Elton.

My parents always seemed larger than life. I’m the youngest of five boys, so even in my earliest memories they were already fully formed grown-ups, bigger than the rooms they walked into.

My dad was well-established in radio, first as an announcer and later as a station manager. He had a wonderful baritone singing voice, and my mother was his accompanist. If there was a piano in the room, they’d perform. Always dressed to the nines, they made quite the impression. The spotlight just seemed to find them, and they never disappointed.

We grew up with music in our home, at church, in the car, and at nearly every gathering we attended. I was wrapped up in their voices, their talent, and their love of performing. What made it even more special was that they always took the time to explain the music to me and the stories behind the songs.

I can still hear my dad’s voice singing the Tom T. Hall country classic, “I Care.”

Here are a few lines:

When you have a bad cough and you can’t go out

When you sleep in the dark and there’s something out there

I want you to know I care

I must admit I always thought he was singing that song just to me. Years later, I discovered all four of my brothers felt exactly the same way. And while Tom T. Hall’s original recording is wonderful, my dad’s version had more heart. I’m not biased, it’s simply true. Just ask my brothers; they’ll tell you the same thing.

I Care is an old country song, mostly forgotten now, but it lives on for me in a very special way. (Treat yourself and look it up on your favorite music app.) It opens with a child’s small worries: a broken toy, a rainy day, nowhere to go. Later verses turn to life’s harder moments: being sick or scared, lying awake in the dark. And every time, the song comes back to the same reassuring place: there’s someone who cares for you, no matter what.

“I want you to know I care. I care, I do, there’s no one like you.”

When Dad sang and Mum played that song and sang that promise, no matter how old I was, I became a little boy again, trying to be good, trying to do the right thing, even when it was hard.

I Care is not a spiritual song, but it’s obvious the writer, Hall, was a man of faith. I grew up in a spiritual family, not just because we went to church, but because our home was filled with devotion, music, family, laughter, and love. And whenever Dad sang these words …

“I mention your name when I’m sayin’ my prayers”

… I knew I was in my parents’ prayers and in their hearts. What better gift could a child get?

Then the song reaches its final promise, and it still lands squarely in my heart, whether I hear it with the ears of a six-year-old or now, six decades later.

“I want you to know I care... I love you so much.”

Every time, it gets me. (I’m not crying, you’re crying.)

I’m the luckiest guy I know because I had a mum and dad like Dalt and Irene Elton. One thing I never doubted: they loved me unconditionally. And when Dad sang “I care” each time, I knew they’d always be there for me. I was never alone.

As for Dalt and Irene, you couldn’t separate the two. There was no Dalt without Irene and vice versa. There would be no song without the piano. They were married for sixty-five years, and it was the greatest love story I have ever known. They were my parents, my friends, my giants.

Thank you, Mum and Dad. Thank you for caring for me and loving me so well.

Now, who are the giants in your life, the people who made it possible for you to see further, dream bigger, and become the person you are today? I’d love to hear your stories.

With gratitude,

I love history because it reminds us that great leadership rarely looks the way we expect. Time and again, history shows us that the right person often emerges when they are needed.

One of my favorite historical figures is Winston Churchill. It was my English grandfather who first made me appreciate him. And without a doubt, Churchill was certainly a character. He had a razor-sharp wit, an iron will, and a personality that could fill a room. More than that, he became the right leader for one extraordinary chapter in history.

In May 1940, Winston Churchill became Prime Minister of Great Britain. He was 65 years old and widely distrusted, even disliked, by many members of his own party. To some, he was a reckless has-been who had already squandered his best political years. Just weeks earlier, most of Parliament would have laughed at the idea that he should lead the nation. His time, they believed, had passed.

Then France fell. The German Luftwaffe filled the skies over England. Suddenly, Britain needed a bulldog who was willing to stand before the nation and declare that surrender was not an option.

Churchill was, by nearly every account, a difficult and complicated man. He was stubborn, moody, impossible to manage, and known to drink too much and sleep too little. In peacetime, many considered him unfit to lead. But in wartime, his strengths stood out. His resolve steadied a frightened nation and helped rally its people through one of history’s darkest hours.

Then, in July 1945, just two months after victory in Europe, the British public voted him out of office.

He hadn’t failed; quite the opposite. He had exceeded almost everyone’s expectations. But the war was over, and the country needed a different kind of leadership. It needed someone who could rebuild housing, find a way to offer healthcare to all, and return hope to ordinary life.

Churchill was the same man, and the season had changed.

I think about that often because I believe we sometimes get leadership wrong. We tend to picture leaders as one type of person: confident, commanding, certain, always out front. We hire for that image, promote for it, and, worse yet, compare ourselves against it. And when we don’t fit the mold of a “leader,” we conclude that maybe we’re just not leadership material.

But leadership is not a single personality type. It’s a fit between a person and a particular season.

Take Abraham Lincoln. Before becoming, arguably, America’s greatest president, he lost bids for the state legislature, for Congress, and for the Senate, twice. By almost any standard, he was no rising political star. He was just a man who kept trying and kept falling short, again and again.

Then the nation fractured in two. America needed someone who could hold together a fragile coalition without tearing it further apart. They needed someone patient enough to absorb relentless criticism, humble enough to surround himself with rivals who often disagreed with him, and steady enough not to panic when everyone around him were losing their heads. The crisis revealed why Lincoln was exactly the leader that particular time required.

What strikes me most about both Churchill and Lincoln is that neither man reinvented himself to meet history. History revealed the value of who they already were.

I think that’s the part we often miss in our own careers.

I’ve spent much of my working life alongside my dear friend studying what helps people and teams thrive. One lesson has become abundantly clear: leadership is not a single way of being.

Some seasons will call for you to be a motivator, someone who can walk into a discouraged room and remind people why their work matters. Other times call for a steady hand, for you to remain calm in the middle of chaos and help everyone else breathe a little easier. Some seasons will require deep compassion, for you to be a leader who can guide exhausted or anxious people with empathy. And, sometimes a team might need you to deliver the hard truth that everyone else has been avoiding.

None of these is the best leadership style. They’re all important, just for different seasons.

I think many of us underestimate potentials leaders because we’re comparing their natural strengths to the wrong situation. The quiet, steady person on your team who rarely raises their voice may not look like a leader during a high-energy sprint. But put them in the middle of a crisis, and watch how the entire room relaxes because they’re in charge. Likewise, a high-energy motivator may be too much during a calm, technical season where precision is needed. But give them a discouraged team that has lost its confidence, and they may be exactly the person who restores hope.

And as for you, if you’ve ever thought, “I’m not really leadership material,” I’d gently push back. You may not be the leader for every room, nobody is. But you may be exactly the right leader for a particular team, a particular challenge … perhaps the one in front of you right now.

The same principle applies when we’re looking for people for our teams. My advice: quit hiring and promoting for one static idea of “leadership.” Instead, ask a better question: What does this team need right now? Is it entering a season that requires stability or one that needs bold change? Does it need someone who can rebuild trust, or someone who can push them to higher performance? When we’re honest about what a situation requires, we might even discover the right leader is already on the team.

Churchill was the right person for one enormous challenge at one extraordinary point in history. That was enough. And he understood his strengths and weaknesses in his own unforgettable way. Near the end of his life, he quipped that he was “ready to meet [his] Maker,” but whether his Maker was “prepared for the great ordeal of meeting” him was another matter entirely.

So here are a few questions I’d invite you to sit with this week:

What season is your team in? What do they need from you as their leader?

And, also consider, is there’s someone who works for you whose particular strengths have been overlooked because they don’t match the stereotype of what a leader is supposed to look like? Could they step up now?

Sometimes the right person has been standing there all along, their moment just hadn’t arrived yet.

I’d love to read your comments.

With gratitude,

🎙️The Culture Works Podcast

The Latest Episode

The Culture Works Podcast dives deep into the evolving dynamics of leadership and workplace culture. Hosted by bestselling authors and leadership experts Adrian Gostick and Chester Elton, this show brings real conversations with C-suite leaders, HR changemakers, and cultural innovators. From recognition and psychological safety to AI disruptions and hybrid work, every episode helps today’s leaders thrive—not just survive. Whether you’re leading a team of five or five thousand, discover practical insights to build cultures that connect, perform, and endure.

In our latest ep, Chester & Adrian chat Carol MacKinlay, CHRO at Pebble, one of the oldest and largest employer of record providers in the world. In this conversation, Carol shares what she learned about transparency when the headlines are bad, why “talent density” beats headcount every time, how customization is the future of HR, and what CHROs should be thinking about right now that they probably aren’t. She also serves on the board of Exodus, which went public in January of last year. Candid, practical, and genuinely funny, this one will stay with you.

The Culture Works podcast ep with Carol MacKinlay.

Let me ask you something.

Have you ever met someone who could walk into a room full of good news and find the one thing that was wrong? Someone who, no matter what was going right, was always keeping score of what was missing?

I’ve been that person — in certain seasons of my life. And I’ll bet you have too.

That habit has a cost. Not just to your mood, but to your life. To the relationships you neglect, the moments you miss, the warmth you never let in. Nobody captures that cost more vividly than Charles Dickens did in A Christmas Carol — a story that is, at its heart, about what a life without gratitude actually looks like.

The man who kept the coins and lost everything else.

Ebenezer Scrooge isn’t a villain. He’s something sadder: a man who used to know happiness and forgot how. Life wore him down, as it does to all of us, and somewhere along the way he stopped giving, stopped connecting, stopped feeling. His only remaining pleasure was counting his money.

In a single night, three spirits force him to see what that choice has cost him — and what it will cost him forever if nothing changes. The last ghost says nothing at all. He simply points to a neglected grave with Scrooge’s name on the stone, and to people who joke about his death because they are relieved he is gone. A life not worth remembering.

Scrooge falls to his knees and asks the question we would all ask if we were honest enough:

“Are these the shadows of the things that Will be — or only of the things that May be?”

That question is everything. Will be or May be?

Dickens doesn’t answer it for him. He lets Scrooge answer it with action. The future isn’t fixed. The ghost isn’t handing down a sentence. It’s offering a gift in the disguise of a nightmare: it is not too late.

And then he woke up laughing.

Here is my favorite moment in the whole story. The morning after the spirits, Scrooge doesn’t wake up weeping with guilt or making solemn resolutions. He laughs — like a man who just had something handed back to him that he thought was gone forever.

“I am as light as a feather! I am as happy as an angel!”

Nothing around him had changed. Same city. Same cold. Same counting house. But he was looking at all of it differently. He was grateful — grateful to be alive, grateful for the chance to make it right.

And then he acted on it. He bought the biggest turkey in the shop for his struggling assistant. He visited the nephew he had avoided for years. He gave to the poor. He showed up.

This is the thing the story gets exactly right: Scrooge didn’t just feel grateful. He expressed it! And that is when everything changed — not just for the people around him, but for him. He became happier not despite the giving, but because of it.

Gratitude that stays inside you is just a feeling. The moment you act on it, it becomes a life.

Scrooge spent decades focused on what was wrong, what was missing, what was threatening. He got to keep the coins and lost the warmth. When he finally changed, he didn’t become naive or pretend the world was perfect. He simply started seeing it fully — and responding to it generously.

That is the whole lesson. A life with gratitude is not a softer life or a less clear-eyed one. It is a richer one. More connected. More meaningful. More worth remembering.

For Scrooge, it happened in one night.

For the rest of us, it takes longer. But the invitation is the same: look around you. See what is actually there. Then do something about it.

So — what are you grateful for today?

Take a minute. Write it down.

🎙️The Culture Works Podcast

The Culture Works Podcast dives deep into the evolving dynamics of leadership and workplace culture. Hosted by bestselling authors and leadership experts Adrian Gostick and Chester Elton, this show brings real conversations with C-suite leaders, HR changemakers, and cultural innovators. From recognition and psychological safety to AI disruptions and hybrid work, every episode helps today’s leaders thrive—not just survive. Whether you’re leading a team of five or five thousand, discover practical insights to build cultures that connect, perform, and endure.

In our latest ep, Chester & Adrian chat Carol MacKinlay, CHRO at Pebble, one of the oldest and largest employer of record providers in the world. In this conversation, Carol shares what she learned about transparency when the headlines are bad, why “talent density” beats headcount every time, how customization is the future of HR, and what CHROs should be thinking about right now that they probably aren’t. She also serves on the board of Exodus, which went public in January of last year. Candid, practical, and genuinely funny, this one will stay with you.

The Culture Works podcast ep with Carol MacKinlay.

“What’s most important to you in your life?”

I’ve become convinced that our calendars reveal more about our values than our words do.

A few years ago, a friend asked me a question that seemed simple enough: “What’s most important to you in your life?”

At the time, I was busy writing, speaking, traveling, and building a career that I genuinely loved. But when she asked what mattered most to me, I answered immediately with something that had nothing to do with my work.

“My family,” I said. And I didn’t hesitate.

But this friend, Ayse Birsel, (pronounced Eye-shay) has a gift for asking follow-up questions that seem straightforward

until you try to answer them honestly.

She nodded and asked something that made me uncomfortable. “If family is what matters most,

what are you doing to design your life that way?”

I really wasn’t sure how to answer. I had goals for my career. I had plans for books I wanted to write, clients I was serving, and speeches I was going to give. My work was filled with intention. But when it came to the people I loved the most, I realized I was mostly hoping things would work out.

I was not alone in that. Most of us know what matters to us, but we don’t always live that way.

If you ask people what’s really important to them, you’ll hear familiar answers including friends, family, faith, health, service. The problem isn’t identifying what we value most, it’s designing our lives around those things.

For instance, if someone says family is their highest priority, but spends every evening and weekend glued to their electronic devices answering every request that comes in, what is their real priority? If someone says serving others matters most, but rarely get out of their office, does it really occupy a meaningful place in their life? If friendship is paramount, but most coffee dates get postponed and phone calls become “maybe next week,” what story is the calendar telling?

I’ve become convinced that our calendars reveal more about our values than our words do.

That realization changed something for my wife Heidi and me. We started having conversations about the kind of memories we wanted our children and grandchildren to carry with them. We wanted to go deeper than the occasional holiday photo or quick family gathering, but to curate rich experiences that would become part of our family’s story.

Eventually, those conversations led us to purchase a small lake house in upstate New York. Nothing extravagant, just a place where people could gather in the summer (and mice over the winter).

Since then, every year our family has gathered together there. Stories are told and meals stretch long into the evening. Grandchildren learn to fish and siblings reconnect. Phones get put down and conversations pick up.

Those memories didn’t happen by accident but because, at some point, we stopped saying family was the most important thing and we started designing our life for it.

And since this is the Gratitude Journal, what fascinates me is that this same principle applies to gratitude. Most of know gratitude is important to our happiness and that of people around us, but we treat it as something spontaneous. We say thank you when we remember. We express appreciation if we aren’t too busy. We assume people will know how we feel about them.

In other words, we leave gratitude to chance.

But if family needs intention, gratitude does too.

The people I know who are exceptionally grateful don’t simply feel gratitude more often than the rest of us, they have built habits around it. They send notes of appreciation every day. They make calls to those they care about and express their gratitude for what they mean to them. They observe milestones and they create traditions of celebration.

Grateful people don’t wait to feel grateful, they design gratitude into their lives.

I’ve come to believe that a meaningful life is built from small intentional choices repeated over time. That might be the choice to call versus putting it off. The choice to visit versus watching the game. The choice to say thank you versus assuming they know what they’ve done.

It’s about the choice to make room for what matters before life crowds it out.

At the end of our lives, people won’t remember most of the things that kept us busy, they’ll remember how we made them feel. How do you want to be remembered? Make your goal to be someone who helped others feel seen, valued, appreciated, loved.

That’s why I think Ayse’s follow-up question mattered so much. She didn’t just ask, “What do you value?” Most of us already know the answer to that. She pushed me to answer,

“What have you designed your life around?”

Often, there is a gap between the two. And closing that gap may be one of the most important things we ever do.

Thank you for supporting our little newsletter. I’d love to hear what you’re intentionally designing into your life right now.

With gratitude,

🎙️The Culture Works Podcast

Most organizations treat HR and marketing as separate worlds. Nate Brock, CHRO and Head of Marketing at Lincoln One Federal Credit Union, decided to knock the wall down between them, and the results speak for themselves:

Enjoy the trailer here and check out the full episode wherever you enjoy listening.

I went to the airport carrying more weight than my suitcase.

I’ll be honest about something I don’t always admit publicly: I was in a bit of a down mood that day. Things were weighing on me, and I was, uncharacteristically, letting it bring down my normally upbeat outlook.

I made it to the security line earlier than I probably needed to and moved through with the shortcuts that come with 2.7 million miles on United. Having an hour to kill, I settled into their lounge.

That’s when I noticed an older woman, sitting by herself.

It was easy to see she was nervous. I was curious about her story, so I sat down next to her and started a conversation: something about the weather, how crowded the lounge was. It doesn’t really matter, we just started talking.

She shared that she normally travels with her husband and was quite nervous about going it alone. She had already called him several times. When I asked where she was headed, it turned out we were on the same flight, so I offered to make sure she got to the gate on time.

After a few minutes I slipped away to stretch my legs. When I came back, she was genuinely surprised I’d returned. She said she’d been waiting and hoping.

We got to the gate and I arranged for her to board in the first group with me, and once we landed I waited for her and made sure she met her daughter at the curb. We said our goodbyes, and she kissed me on the cheek and said something that stopped me in my tracks. “I believe in angels, and today you were my angel.”

I must admit, I was feeling pretty good about myself. Wanting to pat myself on the back a little, I called my lovely wife Heidi and told her the whole story.

Heidi paused. “Ches, do you remember when I dropped you off at the airport this morning? You were all weighed down with worry.”

I did.

She said, “I can hear it in your voice. You are feeling better. Right?”

I was.

“Chester. You weren’t her angel; she was yours.”

That hit me like a lightning bolt.

Of course, my wise better half was right. My new friend had given me several gifts that day: the gift of service, the gift of perspective, and the gift of peace of mind.

That’s the thing about kindness and service. We think we’re the ones giving something away. But more often than not, we end up receiving far more than we offer.

When we show up for the people around us, walls come down. We remember that beneath all the noise and division and worry in the world, most of us are simply trying to get through the day and hoping someone will show us a little grace.

I’ve come to believe that the universe has a way of sending us exactly the right person at exactly the right moment … not just for them, but for us too.

So I’ll ask you: Who have been the angels in your life?

I know you have stories like this, and I would truly love to hear them. Share this with a friend who might need the reminder today.

I am grateful for you.

That number stopped me cold.

Over the last several years, Adrian Gostick and I interviewed psychologists, researchers, and business leaders while researching our book Anxiety at Work. One finding came up repeatedly:

The most resilient people practiced gratitude consistently.

Gratitude helped people regain perspective, strengthen relationships, and create emotional steadiness during uncertainty.

Leaders often underestimate how much calm, recognition, and appreciation shape team resilience.

That’s one reason we created the Anxiety at Work Resilience Training program — practical tools leaders can use to reduce anxiety, build trust, and strengthen resilience inside their teams.

Explore the course

A few years ago, my brilliant friend Ayse Birsel (one of the world’s great designers, whose work hangs in the Museum of Modern Art) said something to me that I haven’t been able to shake: “If you leave something important to chance, chance usually wins.”

What Ayse was talking about encompasses our work, family, legacy, and all the things we say matter most but never quite get around to designing into our lives with purpose.

And that truth also applies to gratitude.

I call this phenomenon accidental gratitude. We express appreciation when it’s convenient and reach out when the mood strikes. We assume the people we appreciate and love — our teams, our friends, our families — will just know how we feel.

Here’s the hard truth: they don’t. Not the way they need to.

My friend Robert Waldinger and his colleague Marc Schulz have spent decades running the Harvard Study of Adult Development, one of the longest studies on human happiness ever conducted. They have found that the single greatest predictor of a long, healthy, and fulfilling life is not your wealth or power, but the quality of our relationships.

And here’s what nobody tells us: relationships don’t maintain themselves. They need intentional nurturing. When you leave them to chance, something starts to fade, often before you even notice.

Think about the people who matter most to you. A mentor who changed your trajectory. A friend who showed up when everything fell apart. A colleague or boss who believed in you before you believed in yourself. Family members who love you unconditionally.

When did you last tell them what they mean to you?

I’m not trying to make anyone feel guilty. I’m trying to wake us all up, myself included. Because accidental gratitude rarely happens in one big missed moment. It’s cumulative. It’s the birthday call you meant to make and forgot. The thank-you note you composed in your head but never put in the mail. The coffee date that keeps getting postponed until it disappears from the calendar forever.

That’s how relationships that could have become extraordinary drift into something forgotten altogether.

I had a friend once who I admired. He would reach out every few months with a quick text asking how I was doing. It was great hearing from him, and I responded almost immediately, sharing the good in my life, the bad, the struggles, and the hopes. But every single time, the conversation stopped there. He sent no response. It was radio silence until the next check-in a few months later.

At first, I found it confusing and a little hurtful. Then my wise wife Heidi gently said something that stuck with me: “He’s casual with his relationships.”

I realized how easy it is for all of us to drift into that pattern. To “check in” without really checking in. To stay loosely connected without ever fully showing up. To be appreciative of someone without really expressing sincere gratitude.

Let’s not be casual with the people we care about. Let’s not leave gratitude to chance or assume people already know how much they matter to us.

So what do you do? Thankfully, it’s simpler than we think:

1. Put it in the Calendar.

Who are you having breakfast with this week? Lunch? Dinner? Who needs a phone call? A text? A handwritten note that shows up on a random Tuesday just because you were thinking of them? Put in in your calendar and your odds are much better that it will happen.

2. Do it Now

When someone’s name pops into your head (and it will) act on it right then. Pick up the phone or send a text or write out a card. Because that thought is an invitation, and every time we ignore an invitation we’re saying no to a relationship that deserves a yes.

3. Keep it Small

We often feel like gratitude needs to be some grand gesture. It doesn’t. The Harvard research backs this up: it’s small, consistent acts of showing up that create the greatest connection. That could be a weekly call or a monthly coffee meeting. A message that says: Hey, I was thinking about you and what you mean to me. That’s what meaningful relationships are made of. You can even go old school and knock on their door!

Here’s what I know after decades of researching gratitude and recognition with my wonderful friend and coauthor Adrian Gostick: you cannot build a life that matters accidentally. In our book “Leading with Gratitude” our research found there are two parts to real appreciation: seeing and then expressing. At its heart, gratitude is something you do. Intentionally and consistently and on purpose.

At the end of the day, people won’t remember your title or your accomplishments, but they will remember how you made them feel. Do you make them feel seen and valued? Do they know they matter to you? That only happens when you design it that way.

So here’s my challenge: Who is one person whose name keeps coming to mind? Reach out today. In fact, right now.

I promise you, it will be appreciated.

Thank you for your support of our little newsletter. I hope it made a difference for you today. Have a wonderful rest of the day and week. I am cheering for you!

With gratitude,

“I’ll be grateful when things get better.”

It’s a thought I’ve had a lot lately; maybe you have too.

But what I’ve learned, often the hard way, is that gratitude is not something we wait for but something we need to reach for, especially when life gets difficult and the days feel dark.

In fact, I think that’s when gratitude matters most.

Research continues to show that gratitude is one of the most powerful tools for building personal resilience. Studies have found that practicing gratitude can reduce stress, improve sleep, and help people recover more effectively from adversity by broadening their perspective and strengthening emotional resilience.

In other words, gratitude doesn’t make us ignore the pain but carry it better.

When life gets heavy, I often find myself thinking about our little lake house in the Adirondacks. It’s my happy place, and I love being there any time of year. I appreciate the natural beauty, the trees, the water, and the calls of the birds, especially the loons. That always calms my soul. It reminds me that the universe is vast and beautiful.

There’s something about walking the quiet trails around the lake with no agenda or noise or even my phone. It’s just me and the trees, water, and time. The Japanese have a beautiful term for this: Shinrin-yoku, or “forest bathing.” It’s the practice of immersing yourself in nature; not to strip off your clothes and wash in the woods (heaven forbid), but to simply be one with the forest. I love that, and it works for me every time.

Studies show that spending time in nature can lower stress hormones like cortisol, reduce anxiety and depression, and improve mood and energy levels. It sure does for me. When I’m out on those trails, my problems don’t magically disappear, but they do seem to get more manageable. I gain perspective.

The trails through the trees remind me there is still beauty in the world, and a lot to be grateful for.

One of the biggest misconceptions about gratitude is that it’s all about how we feel. “I feel grateful my boss recognized me,” or “I feel grateful it’s finally spring.” That’s part of it, sure. But after all the research I’ve done with my coauthor and numerous books we’ve written on the subject, I’ve come to believe gratitude is far more powerful when it becomes more than something we Do. When gratitude becomes action, it becomes who we are, especially in hard times.

Here are a few simple practices that I hope might help:

• At the end of each day name three things (even small ones) that went right.

• Right now, reach out to one person you’re grateful for and tell them why.

• This week, commit an hour to take a quiet walk with no phone and no noise, and notice what’s good around you.

• Most importantly, write down what you are grateful for.

Gratitude becomes more real when it’s visible (a journal is always a good idea).

These aren’t big gestures, but they are intentional choices. I call it “Gratitude by Design.” And like anything that matters, these small acts compound when practiced consistently and made part of your routine.

So, what should you do when life gets hard? When things feel uncertain, it’s important to find the ritual, habit, or reflective moment that works for you. For me, I turn to gratitude … paired with a quiet trail and a little perspective.

Yes, hard times will come. That’s part of the deal, especially lately. We are all dealing with something. But gratitude, when it is designed, practiced, and lived, can help us move through those moments with a little more strength and clarity and hope.

Helpful Hint: When things feel heavy, consider one small thing you can choose to be grateful for.

Thank you for your support of our little newsletter. We are grateful for you.

More often than not, the things that truly last don’t come from big moments. They come from small ones, repeated over and over again.

Think about water for a moment. One drop doesn’t do much. But keep those drops coming day after day, and eventually you get something powerful enough to carve a hole through a rock.

That’s always amazed me.

Which brings me to something fascinating: a beehive.

Think about it for a moment. Thousands of bees, each doing something so small it almost seems insignificant. One bee flies out, gathers a tiny bit of pollen, and returns. Then another goes, and another. Day after day.

It seems so small, yet together, they create beautiful, delicious honey. Something so lasting that jars of sweet honey have been discovered in tombs from Ancient Egypt, still perfectly preserved.

Here’s what makes it even more amazing. A worker bee lives just five to six weeks during the summer. In that short life, she will travel 500 miles or more, flying from flower to flower. And each trip she will carry less than a drop of nectar. Almost nothing. In fact, a single bee will produce about one-twelfth of a teaspoon of honey in her entire life.

To make just one pound of honey, thousands of bees will combine their effort, visiting millions of flowers. And all those tiny efforts add up to something extraordinary.

There’s a lesson there for all of us in our leadership, in our organizations, and in our lives.

My coauthor and friend Adrian Gostick and I have a database full of examples showing how small moments of gratitude can transform teams and lives. We’ve written numerous books on the subject, including our latest, “Leading with Gratitude.” Over the last two decades, we have compiled the data and the stories that all point to the same truth: It’s not the big things that define a culture; it’s the little things.

A thousand thank-yous and small moments of recognition will move the needle more than any big initiative. And a leader who pauses and asks, “What’s going on in your world?” can do more good than the best benefit program ever designed.

On their own, these moments may feel small, but over time they shape cultures.

One of the habits I’ve tried to live by is this modest one: never eat alone. When I grab a meal out, I try to invite someone. When I have a minute in the city for coffee or hot chocolate, I ask someone to come along. And I try not to make it about business, I ask about them, i.e., “How’s your family? What’s been going well for you lately? What’s been hard?”

You’d be amazed how much 30 minutes of genuine attention can mean to others. We all just want to feel seen and heard.

Here’s a simple three-step practice that has helped me over the years. I learned it from my dad, who was a master at making people feel good and building lasting relationships.

• First, notice the good. Look for what people around you are doing well (big or small).

• Second, say it out loud. Don’t assume people know they’re valued, tell them (and be specific).

• Third, choose your response. In real time, choose appreciation (especially in stressful moments).

Why This Matters

Cultures built on recognition and gratitude are more productive, more innovative, and far better at keeping their best people. And lives built with gratitude are more resilient and happier.

So maybe the question isn’t, “What big thing should I be working on?” Maybe it’s simpler: “Who can I invite to coffee today? Who can I thank? Who can I notice?”

It worked for my dad, and it works for me. My dad has been gone for more than a decade now, but he’s still talked about often as someone made the people around him feel seen and heard.

If you want to be remembered, start small.

Thank you for supporting our little newsletter. It means the world to us. And please share your stories of how small things have made a big difference in your life.

With gratitude,

A few years ago, I found myself in a workshop led by , a brilliant designer and author of Design the Life You Love. She’s known for helping people rethink their lives and work.

At one point, Ayse (Eye-Shay) paused, looked at the group, and asked a question: “Who are your heroes?”

Then she pushed us, “I want six.”

That felt like a lot. But something interesting happened. Once I started thinking about it, the names came quickly. My list were: my father, John Dalton; my wife, Heidi; Scott O’Neil (now CEO of LIV Golf); Winston Churchill; Joseph Smith (the founder of my religion); and Martin Luther King Jr.

I chose very different people, from different eras and different walks of life. But they weren’t random. Each one represented something I deeply admire.

My dad stood for joy, humor, and the ability to show up for people. Heidi taught me unconditional love and unshakable faith; Scott O’Neil to assume positive intent; and Winston Churchill grit and the refusal to give up. Joseph Smith reminded me of faith and service, while Martin Luther King Jr. stood for mission-driven purpose that is deeply held and lived out loud.

After we wrote down our lists, Ayse looked at me and said, “Here’s what I know about Chester …” And then she listed those exact qualities I’d listed in my heroes. She said I was all about joy, love, faith, optimism, courage, and purpose.

Then she smiled and said something I’ve never forgotten: “If I’d asked you to list your values, Chester, you might have struggled. But when I asked you who your heroes are and what they believed, your values became self-evident.”

Isn’t that fascinating?

Over the years, my coauthor and I have asked leaders all over the world Ayse’s question, and we’ve noticed a trend. No one ever lists a hero’s ability to make money or their big house. Not once.

What shows up every time is something much deeper. We respect character and service, or courage and love for others. We don’t admire what people have; we admire who they are.

Which leads to the real question: Are we living the qualities we admire? Are we becoming the kind of person someone else might put on their list someday?

We will never become a true hero because of a flashy accomplishments, but because of how we show up in the small moments: When we listen, encourage, stand firm for something good, or believe in someone else before they believe in themselves.

So please, take a few minutes now and write down your six heroes and what they stand for. What does that reveal about you?

Then, take it one step further. Who might you be a hero to? Because whether we realize it or not, someone is always watching. Someone is learning from how we live, how we lead, how we love.

Then, consider what that asks of you. Should you be a little more patient? A little more encouraging? A little more present? Being someone’s hero is not about being perfect, no one ever is, but it should be about being intentional in how you show up for them.

Thank you for being part of this community. Your support of The Gratitude Habit means more than you will ever know.

With gratitude,
Chester

Three messages arrived over the course of three days.

The first came from a dear friend letting me know his mum had passed away. The next day another message arrived from a different friend, another mother gone. Then a third note came through from a friend I hadn’t seen in a while. His message was short and sobering. His health had taken a turn, and he was being moved into hospice.

Three hard messages in three days.

Moments like that have a way of reminding us of that time catches up with all of us. None of us live forever, despite what stories on our news feeds might promise us. And when our time does come, what we leave behind, and how we are remembered, matters more than we might like to admit.

When my friend shared the news about his health, my wife Heidi and I went to see him. We didn’t go with advice or solutions; we certainly didn’t have any answers. We simply went to be there with him.

That turned out to be just what he needed.

We sat and talked for some time. He shared stories about his family, his friends, and his career. As it turns out, we had met on a project I had done for his company. It now feels like a hundred years ago. But what struck me most about our conversation was how often it returned to the subject of service.

My friend talked about the students he had worked with during his career. He spoke about charities he had supported and causes he cared deeply about. He shared stories of refugees he had helped settle into a new life in this new country. Over and over the conversation came back to people. It was clear how much he cares about others, especially the underdog.

When people needed help, he showed up.

By Western standards, my friend might not be wealthy. He doesn’t have fancy cars or a grand house. But sitting with him that day, it was obvious that he was richer than most of us will ever be. His life has been a rich legacy of service, and he is loved and appreciated because of it.

When my other friends spoke about losing their mothers, their memories carried a similar theme. They didn’t talk about status or accomplishments. They talked about love and service. They spoke about mothers who believed in them when they were young, who cared for them when they struggled, and who saw something special in them long before the world ever noticed.

That is what those great women will be remembered for.

Their stories reminded me of my own father, John Dalton “Dalt” Elton, who passed away many years ago. After his funeral, family and friends shared story after story about him, especially about how he made them feel.

My dad had a special gift for lifting people up. He left them laughing and feeling better about themselves. If you were having a bad day, you just needed a little dose of Dalt Elton. Somehow, he had a way of helping you see things a little more brightly.

His answer to the question, “How are you doing?” became legendary among family and friends. With a huge smile he would say, “If it got any better, it wouldn’t be fair!” And then he would laugh. Soon everyone around him would be laughing too.

It was infectious.

But Dad had another gift as well. When people were hurting, he also showed up. He would visit friends in their sorrow, sit quietly with them, and just listen. And before long, he would find a way to bring a little laughter back into the room.

I guess you can say Dalt Elton made people feel loved. And to me, that is a legacy of service.

There is a quote often attributed to Marian Wright Edelman that I have always loved:
“Service is the rent we pay for the space we occupy on this earth.” Albert Schweitzer wrote something similar: “The purpose of human life is to serve, and to show compassion and the will to help others.” And perhaps my favorite reminder comes from Martin Luther King Jr.: “Everybody can be great… because anybody can serve.”

Lately I have found myself wondering what people might say about me someday when I am gone. Will they talk about deals I closed when I was in sales? Will they talk about the books Adrian and I wrote or the speeches we gave? Or will they remember something else, something more simple. Will they remember that I showed up when a friend was grieving? That I took time to listen? That I tried, however imperfectly, to serve the people around me?

In the end, our legacy will not be measured by our achievements or titles. It will be measured in lives we touched, kindness given, and the quiet moments when we showed up for someone who needed us.

Because when everything else fades away, it is not success people remember.

It is service.

Now, I turn this around to you. I’m guessing there is someone in your life who could use a little of you right now. So, I encourage you to call that friend you have been meaning to check in on. Pay a visit to someone who might need company. Sit for a while and simply listen.

Show up.

Because the legacy that matters most is not built in boardrooms or balance sheets. It is built in living rooms, hospital rooms, and quiet conversations between friends. The hugs and the shared tears remind us we are not alone.

I would love to hear your stories. And thank you for supporting our little newsletter. It means the world to us.

With gratitude,

There’s a reason Gordie Howe was known simply as Mr. Hockey.

For decades, he wasn’t just one of the best players in the world, he set the standard for what greatness looked like: strength, skill, durability, and toughness. He even had his own version of a hat trick: a goal, an assist, and a fight, all in the same game. I love it.

Gordie Howe was the definition of a complete player. He was tough, skilled, and always there for his team. His career spanned five decades and almost 1,800 games. When he first laced up his skates, players didn’t wear helmets and goalies didn’t even have masks. By the time he retired at age 52, hockey was filled with fiberglass sticks and players who had grown up idolizing him.

But this isn’t really a story about longevity; it’s a story about love.

In organizations, I see this play out all the time. The leaders who endure aren’t the ones chasing applause. They’re the ones who still care deeply about the mission long after the spotlight fades. In his prime, Gordie Howe dominated the National Hockey League, collecting Hart Trophies, Art Ross titles, and Stanley Cups. He scored 1,805 points over those five decades playing, averaging more than a point a game from the 1940s to the 1980s. Yet despite his dominance of the game, he combined grace and class in a way that made him unforgettable.

To watch him play was to witness a legend in motion.

Of course, as it always does, time caught up with him. In his later playing years, he did slow. The league got faster. Younger players grew bigger and more skilled. And yet, Gordie kept playing.

Why? Because he still loved the game.

When the rival World Hockey Association formed, Howe laced up with the Houston Aeros, and later the Hartford Whalers. He wasn’t chasing legacy at that point; he was chasing joy. I love that. When it’s no longer about the trophies, it becomes about the game itself.

Then came one of the most beautiful chapters of all: Gordie played professional hockey alongside his two sons, Mark and Marty. A father sharing the ice with his children: not in a backyard rink or a weekend league, but at the professional level. I’m pretty sure that’s never happened before and probably never will again. That’s not ambition. That’s gratitude on ice.

Years later, long after most people would have settled comfortably into retirement, Howe did something almost mythical. At age 69, he stepped onto the ice for a single shift with the Detroit Vipers of the American Hockey League. One shift. One last thank-you. One more expression of love for the game that had given him so much. I wish I had been there to see it.

What makes the story even richer is the humility that surrounded his greatness. Wayne Gretzky would eventually break many of Gordie’s scoring records, yet he called Gordie Howe the greatest player ever. In turn, Gordie Howe called Wayne Gretzky the greatest. There was no ego and no insecurity among the two best players of all time, just respect, gratitude, and grace.

There’s a lesson here for all of us.

My coauthor and I could probably have stepped off the stage years ago and settled on a beach in Bali.. Instead, we still find ourselves climbing onto planes, walking into conference rooms, and standing on stages with leaders around the world. Why? Because we love the work. We love helping leaders become better versions of themselves.

At this point in our careers, we’ve had enough applause and kind words to last a lifetime. What keeps us going is that we are still growing, learning, and stretching. We are still trying to get better at serving the people who trust us. The leaders we work with feel the same way. The best ones don’t show up because they have to. They show up because they care.

Being the best can be a worthy goal. But if being the best becomes the only goal, we miss something essential. Gordie Howe reminds us that when you truly love what you do, success doesn’t define your joy, purpose does. And when purpose drives you, retirement doesn’t look like escape. It looks like choosing when and how you lace up again.

So here’s my invitation. If recognition disappeared tomorrow—if the titles and the money were gone—would you still love the responsibility? Would you still lace up?

Because when you love the game, gratitude to be able to play it never retires.

Thanks as always for your support of my little newsletter.

Grateful you’re here,

There’s a wonderful saying: If you want a new idea, read an old book. One of the oldest books still read today is Don Quixote, published in 1605 by Miguel de Cervantes. It tells the story of a country gentleman named Alonso Quixano who reads so many tales of knights and heroism that he decides to become one himself. He renames himself Don Quixote, mounts his scrawny horse (Rocinante), recruits a loyal companion (Sancho Panza), and rides off to defend the helpless and right the wrongs of the world.

I love a good old book.

Most people remember Don Quixote for tilting at windmills he believes are giants. He’s a foolish old knight charging at imaginary enemies and has become a bit of a punchline.

But the older I get, the less ridiculous he seems, and the more necessary.

At heart, Don Quixote is a dreamer. He looks at the dusty, ordinary world and decides it should be better. So, he becomes someone who believes in honor, justice, and courage. He reinvents himself as a knight not because the world asks him to, but because the world needs him to.

That’s the part that inspires me. I find it beautiful.

Quixote doesn’t wait for the world to change before he shows up differently. He treats inns like castles and peasants like royalty because he believes they could be. In leadership terms, he models the behavior he wants to see. He brings the future into existence and takes others along on his dream, his adventure.

What strikes me most is that his “madness” is moral. Unlike so many in the modern world (and probably the old world too), he is not driven by power or profit. He has a sincere desire to defend the weak and live by a code where character still matters. In a cynical age, that might make him look foolish. But in my book it makes him rare and wonderful.

In my life, and I’m sure in yours too, there have been moments when it felt like it would have been better to just throw in the towel. Nothing will change, I thought. So, why bother?

But then we’ve all had our better moments, when we decide to keep trying no matter how hard things are.

For me and my coauthor Adrian Gostick, one of those times came more than two decades ago. We were working for a corporation and decided to write our first book together. No one had done anything like that before, and certainly no one was asking us to. But we knew it would be a good thing for the company, and it would help get the word out about the innovative work our firm was doing with clients.

We might have hoped for a little appreciation of our ingenuity, instead most of what we got was pushback. Some people thought it was a waste of time, others a vanity project. One senior executive argued that he would support it if we put the retired CEO’s name on it as the author (even though the man had moved to another country!).

We could have given up or given in; we didn’t. And you know what? We wrote it, and it did pretty well. That first book sold 40,000 copies. So we wrote another. And that one sold 100,000 copies. A few years later we wrote a book that sold half a million. Today, Adrian and I have coauthored 17 books, sold more than 1.5 million copies, and have spoken all over the world.

That first book was our windmill. We charged at it, and it changed our lives.

Now back to our noble knight, Don Quixote, and the ending. Near the close of the novel, our hero regains his sanity. He renounces his knightly identity and promises that there will be no more quests, no more dreams of justice and adventure.

And not long after that… he dies. That detail has always haunted me.

Symbolically, Cervantes seems to be saying that when the dream dies, the person goes with it. Indeed, when we stop believing that things can be better—when we stop imagining nobility, courage, and goodness into our work and our relationships—we may keep breathing, but something vital inside us shuts down.

I’ve seen this in organizations. I’ve seen it in leaders. I’ve even seen it in myself.

Most of us start out with a purpose. We want to make things better for ourselves, our team members, our customers, our communities, our families. Yet over time, many of us get tired of tilting at windmills: tight budgets, unsupportive peers or bosses, company politics, and so on. And slowly, the dream shrinks.

It’d argue it’s time to stop bemoaning what could be, and start proclaiming, This is how it is going to be!

When Don Quixote did that, he would climb onto Rocinante and ride straight at the problem. He was never guaranteed a win, but he cared enough to try. And so should we.

Yes, to dream is to risk embarrassment. We might even fail publicly. There were plenty of people watching sales of our first book and hoping it would bomb. We didn’t care. We knew that someone has to believe in a better version of the world before it exists.

That belief is what changes everything.

So yes, Don Quixote charged at windmills. But maybe the real question is: what happens when we stop charging at anything at all? Life without dreams becomes dull and gray.

Don Quixote didn’t teach us to fail, he teaches us to care enough to pick a cause (something worthwhile) and to give it our all.

In a world that often rewards cynicism, that may be the bravest lesson of all.

Leadership always begins with belief. In our work with organizations building high-performance cultures, we’ve seen the same pattern: when leaders stop dreaming, performance shrinks. When leaders model courage, teams follow. There is more about how belief shapes culture here

So I ask you now: What windmills are worth tilting at in your world? What part of your life could use a little more nobility and courage? When you find it, please don’t give up. Now more than ever, the world needs more dreamers. We need more Don Quixotes.

We need you.

Thank you for supporting our little newsletter. It means the world to us. Please share your story, I’d love to hear it.

With gratitude,

*The quote is often attributed to Isaac Bashevis Singer, Nobel Prize winning author

Thank you for reading my little newsletter. With gratitude,

I’ve spent my career studying what makes great teams great — and it turns out it’s rarely complicated.

Recognition. Accountability. A little more gratitude.
A little more clarity.

This space is where I share ideas to help leaders build cultures that deliver results and still feel human.

If that matters to you, you’re in the right place.

This month, we’re bringing Top of the Stack back—and the book sitting on top of mine is one every leader should be paying attention to.

The Book

Quantum Progression (The Quantum Leap Edition)
by Valerie Capers Workman

Why this book matters right now

There’s a lot of noise around AI.

Is it good?
Is it bad?
Is it going to take my job?

Valerie cuts through all of that with a simple truth:

AI will not replace you.
It will replace the way the job gets done.

This isn’t a competition between you and the person next to you.
It’s a competition between you and your resistance to change.

That idea alone earns this book a spot on Top of the Stack.

About the author

is the former VP of People at Tesla and former Chief Talent Engagement Officer at Handshake. She’s a licensed attorney with a career spanning Wall Street, Capitol Hill, and Silicon Valley—and she’s been featured in Forbes, The Wall Street Journal, Fortune, and CNBC.

More importantly, she knows how real work actually happens inside organizations.

One idea that really stuck with me

Valerie talks about quantum progression—and it’s not about climbing a ladder.

Careers aren’t linear anymore.
They don’t move in neat steps.

Progress looks like:

• moving sideways to learn

• stepping back to move forward

• making intentional jumps based on where you’re trying to go

AI accelerates that process—but only if you engage with it.

A simple place to start with AI

If AI feels intimidating, Valerie’s advice is refreshingly practical:

Don’t overthink it.
Just start asking questions.

How can I do this better?
How can I prepare smarter?
How can I communicate more clearly?

Whether it’s ChatGPT, Claude, Gemini, or another tool—the point isn’t perfection.
The point is participation.

The leadership takeaway

AI won’t replace emotional intelligence.
It won’t read the room.
It won’t build trust.

That last mile?
That’s still on you.

But leaders who combine tech fluency with human-centered skills will move faster, make better decisions, and lead with more confidence than those who don’t.

Final thought

If you’re thinking, “This all feels a little late for me,” hear this:

It’s not too late.
But the clock is ticking.

The only real risk now is standing still.

🎧 Prefer to listen?
This post is also available as a podcast episode.

📚 Want the book?
Quantum Progression is available now—order one for yourself and one for a colleague who’s navigating change.

Feed your brain.
Stay curious.
We’ll see you next month on Top of the Stack.

In this edition of Top of the Stack, Chester reviews How to Know a Person by David Brooks — a powerful book about seeing others more deeply at work and in life.

He also briefly highlights two bonus reads:
• The Coaching Habit by Michael Bungay Stanier (10-year anniversary edition)
• Don Quixote by Miguel de Cervantes — a reminder of the power of dreamers

This isn’t a traditional book club. Think of it as a reading briefing — one book to explore deeply, two more to consider adding to your own stack.

Featured Book: How to Know a Person — David Brooks

Why this book matters for leaders, listeners, and humans.

Key ideas:

• Seeing others deeply reduces conflict

• Listening to understand vs. listening to respond

• The power of the pause and better questions

If one of these books belongs at the top of your stack, let me know — or bring it into your own book club and conversations.

The Gratitude Table is a small, invitation-only circle—ten leaders, gathered for six months of honest conversation. No stage. No slides. No performance.

Just people who care about how they lead, how they show up, and how gratitude actually works when the work is real and the stakes are high.

We’ll meet once a month. The rhythm will stay simple and familiar. One person brings a real issue into the room. The rest of us listen, ask questions, and reflect. Advice comes later—if it comes at all.

My role isn’t to teach or lecture. It’s to host the conversation, slow us down when needed, and notice the patterns that emerge across our shared experiences. The learning comes from the table itself.

A few expectations, named up front:

What’s shared here stays here.
There’s no selling, no pitching, no posturing.
Titles don’t matter much at this table.
You don’t need to be impressive to belong.

Some months will feel light. Others won’t. That’s normal. Gratitude isn’t about pretending things are fine—it’s about noticing what’s real and choosing how we respond.

This circle has a clear beginning and a clear ending. Six months. When it’s complete, we’ll close it with intention and gratitude for what we created together.

Thank you for accepting the invitation.
I’m looking forward to sitting at the table with you.