Category: Leadership - Page 2

The Hardest Thing a Leader Can Do Is Nothing

Posted on May 6, 2026June 4, 2026 by Team Simon

Most of us became leaders because we’re good at solving problems. We walk into a room full of chaos and we see the path forward. That skill is real, and it got us here.

But there’s a kind of conversation where that exact skill becomes the obstacle.

Someone on our team asks for a few minutes. They start explaining a challenge with a project. And somewhere in the first 60 seconds, we start building the solution. We’re still nodding. We might even be making good eye contact. But we’re already three steps ahead, constructing the answer we’re about to deliver.

And then we deliver it. And the person across from us says “yeah, thanks” in a way that means something else entirely.

What they needed wasn’t our answer. What they needed was to feel not alone. And we skipped straight past that to the part we’re comfortable with.

The listening-only conversation is exactly what it sounds like. Our entire job, for the duration of it, is to understand, not to fix. Someone is overwhelmed, frustrated, or stuck. And what they need most is a leader who can stay present long enough to let them get to the real thing.

Because the real thing is almost never the first thing they say.

Here’s a move that sounds almost too simple to work: before any difficult conversation begins, ask one question. “Do you want me to listen, or would you like help solving it?” Research on therapeutic communication shows this single question reduces the speaker’s distress immediately, because it gives them agency in the exchange. We’ve handed them the wheel before we’ve even started.

Then we listen. Not for gaps in the logic we can fill. Not for the moment our solution becomes relevant. We listen for what’s underneath. “Tell me more.” “What else?” “What does that feel like from the inside?” We go one level deeper each time, and we let the silence do its work between questions.

Simon has noticed this pattern especially at senior levels: the more authority we carry, the heavier our words land. A casual reaction from a senior leader can spiral into a week of anxiety for someone three levels below. Which means our instinct to jump in and reassure, to problem-solve, to move toward resolution, isn’t neutral. It’s weight. And sometimes the most generous thing we can offer is to put that weight down and just be present.

We can even say it directly at the start: “I’m here to understand, not to fix.” Four words that give the other person permission to keep going past the surface version of the problem.

The leaders we remember for a lifetime are rarely the ones with the sharpest answers. They’re the ones in whose presence we felt safe enough to say the true thing.

Every Leader Can Destroy Culture. Here’s a Simple Way to Prevent It

Posted on February 13, 2026February 13, 2026 by Team Simon

“As leaders, we have no right to take our leftovers to people,” said Garry Ridge.

Leftovers. It’s the perfect word for that negative energy we sometimes carry as leaders from one interaction to the next. The frustrating conversation that still echoes in our head when we show up to our next meeting. The disappointing news we haven’t quite processed. The rough morning we haven’t shaken off.

Garry Ridge knows a lot about the impact what’s going in an a leader’s mind can ripple throughout a culture. He was obsessed with culture for the 25 years he led WD-40. And whatever he figured out, worked. Under his leadership, WD-40 grew from $300 million to $3.5 billion in market value while sustaining an extraordinary 93% employee engagement rate. That’s more than success. That’s creating a culture where people choose to bring their whole hearts to work.

Garry did a live Q&A with our Optimism Library subscribers where he shared perspective about what it takes to be the leader we wish we had. “We are just these humble human beings bumbling our way down this pathway of life, and in the bushes are these thieves that come and grab us”—envy, anger, impatience, all those forces that pull us away from who we truly want to be. “For a minute we might feel okay in those bushes, but if we don’t remind ourselves to get out and get back on that bumbling path, we’ll never get to our destination.”

This is about more than being kind, though kindness matters deeply. This is also about performance, about building something that lasts. Scientists call it “emotional contagion,” the reality that a leader’s mood inexorably ripples outward, shaping individual performance, team dynamics, and ultimately, results. (Recent research from MIT Sloan Management Review reveals that leaders everywhere often amplify workplace stress rather than absorb it. A recent analysis published in The Leadership Quarterly confirmed what all too many of us have felt before – leader stress creates an enormous drain on the cognitive and emotional resources of entire organizations, making it harder for everyone to do their best work.)

But here’s the beautiful part: we can choose a different path.

Garry’s Simple Practice That Changes Everything

Garry carried something with him for all 25 years: a small card that he attached to the cover of his notebook with a single question:

“Am I being the person I want to be right now?”

Below that question lived his list: “grateful, caring, empathetic, reasonable, listener, fact-based, balanced, curious, learner, throws sunshine not shadow.”

Before walking into meetings, during difficult moments, or when he felt himself getting pulled off course, he’d glance at it. If the answer was no, the list below reminded him of the path back. This was his simple way of catching himself before he carried frustration from one conversation into the next, before he let a bad morning become someone else’s bad day.

Your Turn

Imagine what corporate cultures would be like if more of us created our own version of Garry’s practice. What if, throughout our day, we ask ourselves: “Am I being the person I want to be right now?”

Try it. Also write down the qualities that define the leader you aspire to be.

Keep it somewhere you’ll see it—on your notebook, your desk, your phone’s lock screen. Before walking into a meeting, glance at it. Before responding to a difficult email, take a look. When you feel a bad moment threatening to spill into someone else’s day, pause and read it.

No leader is perfect. We can’t get it right every time. This is about intention, about consciously choosing who we want to be, moment by moment.

The people we lead don’t expect us to be perfect. They expect us to want to be present. To care about what kind of leader we want to be. They want the best we have to offer…not our leftovers.

If You Ever Second-Guess Yourself in Meetings, Try This

Posted on February 4, 2026February 4, 2026 by Team Simon

Every single one of us has a question, idea, or a perspective that has the power to profoundly impact a meeting—whether it’s unlocking a solution, clarifying confusion, or offering a perspective that will shift the entire conversation.

If only we could have shared it in the meeting instead of keeping it to ourselves.

This struggle is more common than you might think. Last year, we asked our community what keeps them up at night. Across industries and experience levels, one response appeared again and again—and it surprised us. Not “leading through a crisis” or “handling difficult conversations” or “earning a promotion.” It was: “I second-guess myself in meetings.”

At some point in our careers, most of us grapple with imposter syndrome, the persistent fear that we’re intellectually inadequate or about to be exposed as a fraud. Early in his speaking career, Simon experienced this himself. But he learned something profoundly simple: We’re in that meeting because someone already asked us to be there. Our worth has been recognized. The vetting happened. We passed.

“In my early days on stage, I’d be at these amazing conferences with incredible speakers, and I’d think, ‘What am I doing here?'” Simon said. “Then I remembered that somebody else already vetted me. I didn’t have to prove I was worthy of being there. Someone else had already decided I belonged on that stage. So either they were an idiot or I should trust they know what they’re doing. I chose to trust that they knew what they were doing.”

The same goes for the people who hired us and invited us to these meetings.

If we can’t learn to trust the people who chose us to be in the meeting, we risk treating every meeting like an audition or every comment like a test. We exhaust ourselves trying to prove our worth over and over.

The good news is, there are practical strategies that can help: grounding yourself physically and deep breathing, preparing a single question in advance, and contributing early in the meeting rather than later. (According to Google’s Project Aristotle, the longer we wait, the more we overthink; once we’ve spoken once, it becomes easier to speak up again.)

But the most powerful shift starts with a simple reminder.

The next time self-doubt surfaces during a meeting, pause, take a breath, and tell yourself: “Someone already said yes to me being here.”

Then ask: “What do I have to contribute right now?”

Someone already opened the door. Now walk through it.

The 60-Second Leadership Trick That Boosts Confidence When Uncertainty Is Everywhere

Posted on January 22, 2026February 13, 2026 by Team Simon

If there’s one thing every experienced leader knows, it’s this: the higher you climb, the more you’re asked to lead through ambiguity. This has never been truer than right now.

AI is opening possibilities we couldn’t have imagined a year ago. Global dynamics are shifting, creating new opportunities and challenges daily. The strategies that seemed solid last quarter are evolving into something better by lunch. And through it all, your team is looking to you, seeking that steady presence called confidence.

Most leadership advice tells you to “stay positive” or “trust your gut.” But what happens when you need something more concrete, more actionable?

Team Simon has a different approach, one that sounds counterintuitive but is backed by both neuroscience and Simon’s own experience: Stop running from your worst-case scenario.

Instead, rehearse it out loud until it bores you.

Why Your Brain Needs This Right Now

In times of rapid change, our brains naturally work overtime trying to protect us. They run simulations of everything that could go wrong, keeping us stuck in analysis paralysis. But here’s the beautiful paradox: when we deliberately engage with these scenarios instead of suppressing them, we take back our power. We transform anxiety into action. We reclaim our confidence not by denying uncertainty, but by proving to ourselves we can handle whatever comes.

This is about building genuine, earned confidence. The kind that doesn’t crumble when things get hard. The kind that lets you sleep at night and show up fully for your team in the morning.

Make the Monster Mundane

Here’s the specific practice: Take that scenario playing on loop in your mind and voice it dramatically, like you’re directing a scene from an over-the-top action movie. Out loud. With theatrical flair.

“The product launch faces unexpected challenges. Some clients hesitate. The board has tough questions. I’m standing in a conference room navigating a difficult conversation about our investment and timeline while competitors move fast. I’m being tested. The team is watching how I handle this.”

Say it again. Add dramatic pauses. Make it theatrical. Repeat until the emotional charge transforms into something familiar and manageable.

This is about training your brain to recognize that even challenging scenarios are navigable. Simon uses this technique before major talks, transforming nervous energy into focused readiness. As he puts it: “Uncertainty kills confidence because our brains catastrophize silently. Instead of suppressing it, voice it dramatically… Repeat until the drama fizzles.”

Your Brain on Rehearsal

This practice is grounded in exposure therapy, a well-established psychological technique. Research published in the Journal of Anxiety Disorders demonstrates that repeated exposure to feared scenarios, even through imagination and verbalization, transforms the emotional intensity of those fears. Your amygdala, the brain’s alert system, learns to recalibrate its response.

Neuroscience research shows that when we silently ruminate on challenging scenarios, our brains activate stress responses. But when we externalize and repeatedly rehearse these scenarios, we engage different neural pathways, ones associated with cognitive control and emotional regulation. We move from reactive to responsive.

Dr. Michelle Craske, a leading anxiety researcher at UCLA, has shown that repeated exposure works precisely because it updates our brain’s assessment of what we can handle. When we rehearse and the catastrophe doesn’t materialize, our confidence naturally rebuilds. The challenge becomes manageable.

Why Courage Isn’t a Solo Act

This practice becomes even more powerful when combined with another truth Simon champions about leadership courage. He often says: “I do not believe that courage is deep internal fortitude. Dig down deep and find the courage. I just don’t think that’s true.”

Instead, Simon has discovered that real courage, and the confidence that accompanies it, comes from relationships. “The people I’ve met who truly have courage, courage that we don’t have. If you ask them, why did you do it? They all say the same thing. Because they would have done it for me.”

So pair the worst-case rehearsal with that leadership buddy, that one person you can be completely honest with. After you’ve rehearsed your challenging scenario into familiarity, share it with them. Not for solutions, but for perspective. As Simon puts it: “All you need is one person in your life, one who says to you, I gotcha. I gotcha. If this whole thing goes sideways, I’ll still be there with you. Or they’ll put their hand on your shoulder and say, you got this.”

How to Actually Do This

Here’s what this looks like: Block 15 minutes on your calendar. Find a private space: your car, a conference room, a walk outside. Voice your specific challenging scenario with theatrical energy. Don’t just think it; perform it. Make it so dramatic that it becomes almost comedic.

Then ask: “Okay, and if that actually happened… then what?” Walk through your actual response plan. Who would you call? What would you do first? How have you navigated challenges before?

Do this regularly when you’re facing major uncertainty. The goal isn’t to convince yourself nothing will ever be difficult. It’s to prove to yourself that whatever comes, you’re capable of handling it.

Confidence isn’t the absence of uncertainty. It’s uncertainty that’s been looked in the eye, rehearsed, and transformed into fuel. When you can narrate your challenging scenario with the same energy as a dramatic movie trailer, you’ve taken back your power.

The uncertainty isn’t going anywhere. But your relationship with it can transform entirely.

What’s one scenario on your mind right now? Give yourself 60 seconds today to narrate it out loud. You might be surprised how quickly clarity emerges.

Struggling to Find Work? Here’s One Thing That Actually Works

Posted on January 16, 2026February 13, 2026 by Team Simon

Everyone knows the feeling of sending out résumés into the void and hearing nothing back. It’s exhausting. It’s demoralizing. And it makes you wonder if there’s something wrong with you.

There isn’t.

Working at The Optimism Company, we often hear from people in this exact moment who reach out for advice. And here’s what breaks our hearts: They’re doing everything they’ve been told to do. They’re working hard. They’re persistent. They’re following the rules.

But what if the rules are wrong?

What if the path to meaningful work isn’t about sending more applications, but about having one real conversation? What if your next opportunity isn’t hiding in a job posting but in a relationship you haven’t built yet?

Here’s what we know, and what the research confirms: The people who find work that matters don’t chase jobs. They build relationships.

The Truth Hiding in the Numbers

The data tells a remarkable story: 70% of jobs are found through networking, not through the applications we obsess over. Even more striking? Only 7% of job applicants get referrals, yet referrals make up 40% of new hires.

When someone vouches for you, when someone knows your story, you don’t just have a better chance. You have a fundamentally different kind of chance.

But here’s where it gets really interesting, and hopeful.

You know how we’re told to lean on our closest friends and family? Turns out, that’s not where the magic happens. A landmark study from MIT, Harvard, Stanford, and LinkedIn involving 20 million people discovered something beautiful: The connections that change our careers aren’t always our closest ones. They’re what researchers call “moderately weak ties.” These are acquaintances, people we don’t know super well yet, connections just outside our inner circle.

Why? Because these relationships give us access to entirely new worlds. They open up new information, new possibilities, new ways of thinking that our closest friends, who already know what we know, simply can’t provide.

Sociologist Mark Granovetter figured this out back in 1973, and it’s been confirmed over and over: The person who changes your life might be someone you barely know.

What If You Changed Just One Thing?

Imagine for a moment that instead of sending another application into the void, you did something different. Something that felt less like begging for a job and more like being human.

What if you reached out to someone whose work lights you up, not to ask for a job, but simply to learn from them?

This is curiosity. This is connection. This is one person saying to another: “I see what you’re doing, and it matters to me. Can you help me understand how you got there?”

This approach has a name (informational interviewing), and research from the University of Minnesota shows it does something powerful: It doesn’t just help you gather information. It fundamentally increases your confidence in your ability to connect with others. It opens doors you didn’t even know existed. Studies confirm that people who network with genuine curiosity land higher-quality jobs. They find work that actually aligns with what matters to them.

Because when you approach someone with real curiosity, you’re not asking them for something. You’re offering them something rare: the chance to be helpful, to be valued, to share what they’ve learned.

Try questions like these:

“How did you figure out what mattered most in your career?”
“What surprised you most when you first started in this field?”
“Looking back, what advice would you give to someone just beginning this journey?”

These aren’t interview questions. They’re invitations to real conversation. And real conversations change things.

Why Connection Wins (Every Single Time)

Think about what happens when you send an application online. You become a PDF. A list of bullet points. A file in a folder alongside hundreds of other files that all look basically the same.

But when you reach out with genuine curiosity? Everything changes.

You become a person.

Here’s what happens when you approach your search through connection instead of transaction:

You discover what matters (before anyone else does).
Informational interviews unlock insider knowledge you simply cannot find anywhere else. You learn what skills actually matter in the day-to-day work, not just what’s listed in job descriptions. You hear about the challenges organizations are facing before they even know they need to hire for them. You become someone who understands, not just someone who wants.
You become unforgettable.
People don’t remember the person who asked for a job. They remember the person who asked thoughtful questions, who listened deeply, who made them feel valued. When you approach networking as learning rather than asking, something shifts. You’re not another desperate job seeker. You’re someone they want to help.
You gain access to possibilities no one else can see.
Here’s a fact that should change how you think about everything: As many as 70% of jobs never even get posted. They’re filled quietly, through conversations, through connections, through someone saying, “You know who would be perfect for this?”

When you build real relationships, you’re not just finding jobs. You’re finding opportunities that don’t exist yet for anyone else.

Here’s What You Can Do Today

You don’t need to overhaul your entire approach. You don’t need to become someone you’re not. You just need to start with one conversation.

Close this article. Take a breath. And think of one person (just one) whose work genuinely excites you. Someone who’s doing something you’d love to understand better. It doesn’t have to be someone you know well. In fact, research suggests it’s often more powerful if it isn’t.

Now, reach out. Today. Right now if you can.

Keep it simple. Keep it human:

“Hi [Name], I came across your work on [specific thing] and it really resonated with me. I’m exploring [field/career] and would love to learn from your experience. Would you have 15 minutes for a brief conversation? I’m particularly curious about [genuine question you actually want to know].”

No pressure. No hidden agenda. Just honest curiosity.

That’s it. That’s where everything begins.

The Pattern We Keep Seeing

Research from Lee Hecht Harrison shows that the average job seeker talks to about 25 decision-makers before landing their next role. But here’s what matters: Those 25 conversations aren’t random. They’re not applications thrown into the void. They’re relationships. They’re people who know your story, who see your potential, who might just think of you when an opportunity emerges.

That’s not luck. That’s what happens when you show up as a whole person, not just a résumé.

5 Life-Changing Leadership Books That Aren’t Actually Leadership Books (According to Top Leaders)

Posted on January 9, 2026January 9, 2026 by Team Simon

Leadership isn’t about org charts or management systems. It’s about people. Understanding them. Inspiring them. Creating spaces where they feel safe enough to be fully human.

The leaders who built the most enduring companies—the ones who transformed entire industries—didn’t get there by studying tactics. They got there by understanding humanity itself.

When you stop looking for leadership lessons in “leadership books” and start looking in human stories, something shifts. You stop managing. You start inspiring.

According to lots of well-known leaders, the stories about butlers, rowers, and captains navigating storms can teach you what no business framework can: what it means to be human under pressure, in community, facing the unknown.

Here are five books that top leaders—from Netflix’s Ted Sarandos to Google’s Sundar Pichai to Microsoft’s Satya Nadella—swear by. None of them are written by Stephen Covey, and none of them are found in the business section. All of them are about what it means to be human.

1. Typhoon by Joseph Conrad

Ted Sarandos, Netflix Co-CEO

Ted Sarandos doesn’t read management books. He reads novels. And his favorite is a 122-year-old story about a ship captain caught in a storm.

“It doesn’t sound like a management story on the surface, but I think it’s the most powerful leadership story I’ve ever read,” Sarandos told CNBC this week. “I read it over and over again because I get something different in the book every time.”

Here’s why: Real leadership isn’t tested when everything goes according to plan. It’s tested when the storm hits. When you have incomplete information. When the pressure is crushing and the decisions are impossible.

That’s when you discover what kind of leader you really are.

Conrad’s captain makes impossible choices under unimaginable pressure. And somehow, he brings his crew through. Not because he has all the answers. Because he stays present, stays human, stays committed to his people even when everything is chaos.

When Sarandos first read Typhoon two decades ago, he thought the captain was reckless. On later readings, he discovered profound lessons about leading through uncertainty—exactly the situations leaders face when their carefully laid plans fall apart.

If that’s not a metaphor for modern leadership, we don’t know what is.

2. The Gene: An Intimate History by Siddhartha Mukherjee

Sundar Pichai, Google CEO

What does genetics have to do with leadership? Everything, if you’re Sundar Pichai.

The Gene is the story of how scientists unraveled the mysteries of heredity, from Aristotle’s early theories to the Human Genome Project. It’s about discovery, ethics, and what it means to be human at the most fundamental level.

So why does the CEO of one of the world’s most powerful tech companies recommend it?

Because the best leaders understand that innovation is about understanding humanity itself. Where we come from. What makes us who we are. The ethical questions that emerge when science gives us god-like powers.

Mukherjee, a Pulitzer Prize-winning oncologist and writer, weaves together science, history, and deeply personal stories. He explores not just what genes do, but what they mean—for individuals, for families, for society.

For Pichai, who leads a company developing AI and technologies that will reshape human experience, these questions aren’t academic. They’re urgent. Understanding the biological blueprint of humanity helps him think more deeply about the technological blueprints Google is creating.

3. The Boys in the Boat by Daniel James Brown

Satya Nadella, Microsoft CEO

Imagine nine working-class boys from Depression-era America, none of them wealthy, none of them privileged. They’re rowers. And in 1936, they did something impossible: they beat the world’s elite teams and won Olympic gold.

This is the book Satya Nadella turned to when he became Microsoft CEO. Not a tech book. Not a strategy guide. A story about teamwork.

“A wonderful illustration of the importance of teamwork, which was a core part of my focus out of the gate as CEO,” Nadella said.

The rowers discovered something called “swing”—that magical state where nine individuals move as one, where the boat seems to lift and glide effortlessly. It only happens when ego disappears and trust takes over.

Sound familiar? That’s leadership.

4. The Remains of the Day by Kazuo Ishiguro

Jeff Bezos, Amazon Founder

“I learn more from novels than from nonfiction,” Jeff Bezos has said.

His favorite? A heartbreaking story about a butler who gave his entire life to serving with dignity, only to realize, too late, that he’d sacrificed his humanity in the process.

The Remains of the Day is a novel about regret. About loyalty to outdated systems. About the cost of never questioning authority. And for Bezos, it became something profound: a framework for how to live.

He calls it his “regret-minimization framework.” When making decisions, he asks: What choice will I regret least when I’m 80 years old?

The butler, Stevens, couldn’t change. He couldn’t adapt. He couldn’t question. And he lost everything that mattered. Bezos learned the opposite lesson: Hold on to your vision, but never be imprisoned by the past. Know when to preserve and when to revolutionize.

5. How to Talk So Kids Will Listen & Listen So Kids Will Talk by Adele Faber and Elaine Mazlish

Simon Sinek

Here’s something Simon always says: Leadership is like good parenting.

That’s why one of his favorite leadership books is a parenting manual from the 1980s.

“It’s not a traditional leadership book, but it’s one of the best,” Simon says. “It teaches you to ask open-ended questions like ‘What do you love?’ or ‘When do you come alive?’ to draw out people’s passions and build real trust. I recommend it all the time.”

Think about what great parents do. They listen. They validate feelings. They ask questions instead of giving orders. They create safety so their kids can take risks, make mistakes, and grow.

Now imagine if every leader did that.

As Simon puts it: “It’s like a bright yellow guide to human connection.”

What book changed how you see leadership? We’d love to hear your story. Because the best insights don’t come from textbooks—they come from each other. Feel free to reach out at [email protected].

How Mastering These “Insignificant” Moments at Work Can Change Everything

Posted on January 9, 2026February 13, 2026 by Team Simon

Many of us spend years chasing the wrong things as leaders. We obsess over engagement surveys, invest in elaborate wellness programs, and architect perfect org structures. Meanwhile, the real drivers of how our teams feel—and how they perform—are happening in the three-second interactions we barely notice.

According to new research led by Ioannis Kratsiotis, lecturer in organizational psychology at the UK’s Manchester Metropolitan University, creating really good days at work don’t require major changes or perfect conditions. They’re simply created through small everyday moments that help people feel free, capable and connected.

The Five Moments That Actually Matter

Kratsiotis identified five moments and interactions that can help colleagues foster “a sense of autonomy, a sense of competency, and a sense of connection:”

1. THE SUPPORT MOMENT

Brief check-ins and quick offers of advice help people feel connected and supported, lifting mood and motivation throughout the day.

Do this: Before you finish each day, reach out to one person—not to assign work, but to genuinely offer support or connect.

2. THE PROGRESS MOMENT

Feeling effective is one of the strongest drivers of wellbeing, and recognizing small wins builds competence that carries into the rest of the day.

Do this: Start meetings with “What’s one thing you made progress on this week?” Send quick messages when you notice forward movement.

3. THE AUTONOMY MOMENT

A sense of freedom in how we approach work plays an important role in how we feel each day, and showing trust strengthens relationships while helping people maintain focus.

Do this: When assigning work, separate the “what” from the “how”: “Here’s what needs to happen and why. I trust you on the approach.”

4. THE CONNECTION MOMENT

Short moments of genuine connection can change the tone of the entire day and help you both leave work feeling lighter and more energized.

Do this: Show up 2 minutes early to virtual meetings. Ask one non-work question each week. Send appreciative messages with no request attached.

5. THE RESTORATION MOMENT

When people feel drained, often one of their basic needs isn’t being met, and restoring balance matters more than maximizing any single need.

Do this: When someone seems stuck, ask: “What do you need right now? More clarity, more freedom, or someone to brainstorm with?”

You can’t fake these moments or delegate them to HR. They require you to be consistently present, genuinely interested, and willing to slow down enough to notice what your team actually needs.

Some days you’ll forget. That’s human. What matters is the pattern over time. We have more influence over daily experience than we sometimes realize, and by paying attention to the small moments that shape our day, we can create more days that leave people fulfilled at work and refreshed at home.

Why Boredom Is a Leader’s Best Friend

Posted on January 9, 2026January 9, 2026 by Team Simon

Here’s a question for you: When was the last time you were truly bored?

Not frustrated. Not waiting in line scrolling through your phone. Not filling every micro-moment with a podcast or email check. But genuinely, profoundly bored—staring at nothing, thinking about everything, with no agenda whatsoever.

If you’re like most leaders, the answer is probably “I can’t remember.” And that’s precisely the problem.

At Team Simon, we love studying what makes great leaders great. We’ve explored the power of purpose, the infinite mindset, and why leaders eat last. But one of the most counterintuitive insights we’ve encountered is this: boredom itself is essential to visionary leadership.

The Boredom Walks That Changed Everything

Simon discovered this recently through a conversation with Elle Cordova, a polymath who transformed lockdown isolation into viral poetry and music. Elle shared her secret weapon with him: “boredom walks.”

“She calls them ‘boredom walks,'” Simon says, “leaving the phone behind to let ideas bubble up.” No destination. No podcast. No productivity goals. Just walking and being present with whatever thoughts emerge.

In our hyper-connected, hyper-productive world, this sounds almost rebellious. But here’s what Elle understood: creativity doesn’t happen in the frenzy. It happens in the gaps.

The Wisdom of Sitting Still

Simon shares another formative experience: “I once got advice to go to Central Park, grab a coffee, sit on a bench, and just watch people for an hour. No agenda, no notes. It sounded absurd at the time, but he was right.”

Think about what that advice required: giving up an hour of “productive” time to do absolutely nothing measurable. For most leaders, that sounds impossible. Our calendars are packed. Our teams need us. There’s always another fire to put out.

But that’s exactly why boredom is so powerful. It creates space for rumination—the kind where your brain connects dots it couldn’t under pressure.

Why We’re Addicted to Busyness

Remembering his conversation with Elle, Simon says, “we laughed about America’s ‘vomit reaction’ to boredom. We’re addicted to stimulation, convinced idle time is wasted.”

This addiction isn’t accidental. Our brains crave the dopamine hit of busyness—the ping of a notification, the satisfaction of checking off a task, the feeling of being needed. We’ve built entire cultures around glorifying “the hustle” and wearing exhaustion as a badge of honor.

But here’s what we’re missing: in a world of AI and endless productivity tools, human innovation comes from what machines can’t replicate—curious, unstructured thought.

Elle learned card counting for blackjack not from apps, but from daydreaming about probabilities. When Simon struggled writing Leaders Eat Last, it wasn’t another meeting or research session that unlocked his breakthrough. “A walk in New York and a friend’s call pulled me through,” he recalls. Boredom forced the clarity.

What Boredom Does for Leadership

A bored leader is a reflective leader. And reflection is where transformation happens.

When you create space for boredom, you:

Reconnect with your WHY: The daily grind can obscure your deeper purpose. Boredom strips away the noise so you can hear what truly matters again.

See patterns others miss: Your brain needs idle time to process information and connect seemingly unrelated ideas. Innovation lives in those connections.

Shift from reactive to visionary: You’re not just responding to the urgent—you’re envisioning what’s possible.

Model trust and confidence: Teams follow leaders who have the courage to pause and think deeply, not just react constantly.

Without boredom, we default to finite games—chasing short-term wins and metrics over meaning. But when you embrace the infinite mindset, boredom becomes your ally for trust-building and innovation.

One Leadership Habit That Will Transform Your 2026

Posted on December 23, 2025December 23, 2025 by Team Simon

Imagine a world where work doesn’t drain us, but fills us. Where Monday mornings feel like possibility, not punishment. Where we don’t just tolerate our teammates, we’d go to battle for them. That world exists. And it starts with the choice to stop building teams of stars and start building teams that trust.

There’s a stat Simon loves to cite, and it reveals everything about what makes teams truly great: teams of average performers consistently beat teams of high performers. Not sometimes. Consistently.

We obsess over hiring stars, the top 1% individuals with killer résumés and metrics. We chase the people who shine brightest in interviews, who have the most impressive achievements listed on LinkedIn. But here’s what happens when you stack them together without trust: they fracture. They compete internally, hoard wins, focus on personal glory.

Average folks? They prioritize the team. They serve each other, share credit, cover weaknesses. That’s the secret sauce for real outperformance.

Simon has seen it in action with groups he’s studied. The “stars” burn bright alone but dim in ensembles. The everyday players, bonded by mutual devotion, win marathons.

Why This Matters Now

We’re entering 2026 carrying the weight of years that asked too much. We’re tired. Our teams are tired. And in that exhaustion, there’s a temptation to look for the hero, the superstar who’ll save us all.

But salvation doesn’t come from one brilliant person. It comes from many good people choosing each other, again and again.

When Simon taught, he stacked his top performers on one team. They fought over credit, complained about slackers in his office. “My grade, my work,” they’d say. The average team? They covered for each other, focused on the group grade. They won every time because they trusted, they teamed.

Why does this surprise us? Because our metrics worship individuals. We celebrate the person who closed the biggest deal, hit their numbers, got the promotion. But leadership’s job isn’t to crown winners. It’s to build the container for collective magic. It’s to create the space where people feel safe enough to serve something bigger than themselves.

The Habit: Ask One Question Every Time

Here’s the one leadership habit that will transform your 2026, and it’s beautifully simple: every time someone on your team has a win, ask them one question: “Who helped you?”

Not as an afterthought. Not casually. But as the first response to every success.

Then, and this is critical, publicly recognize those helpers by name. In the team meeting. In the Slack channel. In the email to leadership. Make the assist as visible as the goal.

When Elizabeth closes the big client, don’t just celebrate Elizabeth. Ask her, “Who helped you?” Then send a message: “Elizabeth landed this client, and she says it wouldn’t have happened without Jake’s research, Maria’s introduction, and Tom covering her other accounts. That’s what winning looks like here.”

Do this every single week. Every win. Every milestone. Every success.

Watch what happens.

People will start helping each other more because they know it will be seen. They’ll stop hoarding information because collaboration gets recognized. The quiet contributors, the ones who always made others better but never got noticed, will finally feel valued. And your stars? The good ones will lean into it. They’ll realize their legacy isn’t what they achieved alone, but who they brought up with them.

What Changes

This one question reshapes everything. It shifts you from scorekeeper to culture guardian. It changes what people compete for. Instead of fighting over individual glory, they’ll compete to be the person others name when asked who helped.

You’re teaching your team what you value. And when you consistently value mutual devotion over individual brilliance, you build the trust where average people choose to serve each other. That’s how you create a real team, not just a group working together.

Teams that trust outperform every time.

The Choice Ahead

As we head into 2026, most leaders will keep doing what they’ve always done. They’ll chase the next superstar hire. They’ll celebrate individual metrics. They’ll wonder why their talented teams underperform.

You can choose differently.

You can be the leader who builds something rare: a team that actually cares about each other. Where people show up not just for the paycheck, but for the people. Where the work matters because we’re doing it together.

“Leadership is not about being in charge,” Simon says. “Leadership is about taking care of those in your charge.”

Your team doesn’t need more stars. They need you to see the constellation they’re already forming. They need you to illuminate the connections between them, to make visible all the quiet acts of service that make the magic possible.

One question. Every win. “Who helped you?”

That’s how you transform 2026. That’s how you build the world where work fills us instead of draining us.