We turn it over in our head. We ask a few more questions. We look for one more data point. We check with another person whose opinion we respect. We wait for the timing to feel right.
And still, we hesitate.
We tell ourselves we need more information. More time. More certainty.
Indecision usually grows from very human places. Fear of being wrong. Fear of being blamed. Fear of choosing a path that can’t be undone. Fear of embarrassment.
Add decision fatigue to the mix and postponement starts to feel reasonable.
Meanwhile, the cost of waiting accumulates quietly. Teams stall. Momentum fades. Confidence erodes. What began as a thoughtful pause turns into drift.
Most leadership decisions are made without perfect information. Progress rarely waits for certainty.
So, what is our hesitation really telling us?
Sometimes, it’s a clear no. A request pulls us away from what matters most. We don’t like what we see, but we’re not sure why. Maybe a partnership doesn’t sit right with our values. In these moments, extended thinking isn’t searching for clarity. It’s searching for a way to explain our decision.
Other times, we hesitate because the decision stretches us. It introduces uncertainty. It raises our visibility. It asks more of us than we feel ready to give. Growth decisions usually feel uncomfortable before they feel right.
At some point, the data stops improving and the waiting stops helping.
Start small. Take a step that tests the decision rather than locking it in. Forward motion reveals new information…something thinking alone can’t.
A decision that turns out to be wrong isn’t failure.
It’s feedback.
And feedback points us toward our next decision.
“Whenever you see a successful business, someone once made a courageous decision.” — Peter F. Drucker
Photo by ChatGPT’s new image generator, which is way better than prior versions of the tool.
In sales, there’s an old saying that has echoed through offices and training rooms for decades.
Always be closing.
It’s meant to keep the salesperson focused on their end goal. Keep the deal moving forward. Stay alert to opportunity. Maintain momentum.
Over the years, I’ve come to believe leaders need a different version of that advice.
Always be coaching.
As a leader, your mission is to develop the people who will come after you. You lift others through quiet, daily work that helps them grow. Your job is to bring out the best in yourself and in the people who will eventually step into your role. Coaching drives growth and keeps it moving forward.
Coaching your team is a way of saying, “Your future matters to me.” Coaching your children says, “I believe you have more inside you than you can see today.” And coaching yourself acknowledges the simple truth that growth must continue throughout life, especially for the leader.
Great coaches do more than explain ideas. They create space for practice. They help others turn new knowledge into muscle memory. They offer challenges sized just right for the moment. They ask questions that change how a person thinks about a problem. They reveal a new angle or a new path forward when something feels unsolvable.
Coaching takes learning to the next level. You learn something. You put it into practice. Then you pass it on. Teaching anchors the lesson. It deepens the insight. It turns wisdom into a gift you can hand to others.
Coaching doesn’t require perfect knowledge. It requires humble generosity. Share the insight you gained from yesterday’s challenge. Share the questions that helped you see an issue more clearly. Share the perspective that lifted your confidence when you needed it most.
Leadership is a relay. Someone handed the baton to you. One day you’ll hand it to someone else. The best leaders prepare the people who will run ahead long after they’ve finished their leg of the race.
Who have you coached today? This week? This month?
This is your responsibility. Your opportunity. Your mission.
Ideas and wisdom often arrive with familiar roots.
My views on leadership come from my lived experiences and lessons I’ve learned from great builders and thinkers like Andrew Carnegie, Peter Drucker, Tom Peters, Ken Blanchard, Marshall Goldsmith, Zig Ziglar, Stephen Covey, Jack Welch, Seth Godin, Jeff Bezos, Gary Vaynerchuk, Tim Ferriss, Jocko Willink, James Clear, and countless others.
I’ve also worked with amazing managers and mentors over many decades, including a few who taught me what not to do.
Since I find myself often returning to these lessons, I thought it would be useful to write them down in a list for easier reference.
Leadership Foundations
1. Leadership begins in your mind long before it shows up in your actions.
2. Self-awareness is a leader’s first and most enduring responsibility. Know how your actions land, then lead on purpose.
3. Character outweighs credentials over the long haul.
4. Integrity compounds like interest. The longer you hold on to it, the more it grows.
5. Values are the compass that keep you on course when circumstances shift.
6. Humility is the strength to put others first.
7. Influence comes from trust, not job descriptions.
Vision and Direction
8. A leader’s vision must be big enough to inspire, but clear enough to act on today.
9. Clarity reduces fear. Ambiguity fuels it.
10. Momentum builds when people see the destination and believe they can reach it.
11. Vision is not just what you see. It’s what you help others see.
12. The clearer you are about the goal, the less room there is for fear to grow.
13. Purpose is the map. Storms are just temporary detours.
14. Belief in the destination turns small steps into powerful strides.
15. Every action should feel like part of the same bigger story.
16. Sometimes waiting is the boldest move you can make. Strategic patience is powerful (and extremely difficult).
People and Relationships
17. The right people in the right roles multiply results beyond what you can imagine.
18. A culture of respect will outlast a culture of urgency.
19. Listen like the person speaking might hand you the missing puzzle piece.
20. Pass the applause to others but keep the accountability close to your chest.
21. Trust is invisible, but when it’s gone, everything feels heavier.
22. Relationships need regular deposits of attention, not just withdrawals of effort.
23. Helping someone else win creates a tailwind for your own success.
Decision-Making
24. Good decisions blend facts, values, and the courage to act.
25. The first idea is often just the trailhead. Walk farther.
26. Energy without wisdom burns out. Wisdom without energy gathers dust.
27. Choose the option you can defend in the daylight and live with in the dark.
28. A quick, small decision can open doors a perfect plan never reaches.
29. It’s easier to fix a wrong turn early than to build a new road later.
30. Never cash in tomorrow’s credibility for today’s convenience.
Resilience and Adaptability
31. A setback is a classroom, not a graveyard.
32. Flexibility is a skill, not a personality trait. Practice it.
33. Change is the proving ground where talk becomes action. Priorities sharpen, assumptions get tested, and leadership shows up in decisions, owners, and dates. If nothing changes (no decision, no owner, no date) it was only talk.
34. Adapt your tactics, but never your core.
35. The best views are earned with effort you once thought impossible.
36. Challenges test your limits so you can discover you’re stronger than you ever imagined.
37. Sticking with it usually turns “almost” into “done.”
Growth and Learning
38. The best questions are the ones you don’t yet know how to answer.
39. The moment you stop learning, you stop leading. Sometimes before you notice.
40. Pride blocks the front door to growth. Curiosity leaves it wide open.
41. Ask for feedback before circumstances force it on you.
42. Teach your knowledge, always remembering that your actions teach your values.
43. Every conversation nudges someone closer to, or further from, their best self.
44. Failure carries lessons that success hides. Corollary: High water covers a lot of stumps.
Impact and Legacy
45. Success without significance is empty.
46. The influence you have on people’s lives will outlast your achievements.
47. Your legacy is written in the lives you touch, not in the titles you hold.
48. Leadership is something you borrow from the future. It must be returned in good condition.
49. The most meaningful titles are the ones people give you, not the ones on your nameplate.
50. Think in decades when deciding what to plant today.
51. Your success is multiplied when others stand taller because of you.
52. The best proof of leadership is when growth continues without your hand on the wheel.
53. Leave every place and every person better than they were when you arrived.
Communication & Culture
54. Say the quiet part kindly and clearly. Clarity without kindness bruises. Kindness without clarity confuses.
55. Stories travel farther (and faster) than memos. Stories move people. Memos inform them. Stories turn intention into action.
56. Consistency in small signals (tone, timing, follow-through) builds culture faster than slogans.
57. Meetings should create movement. Reserve live time for decisions and collaboration. End with owners and dates. If it’s just a podcast, send an email. If only two people need to talk, make it a call and give everyone else their time back.
58. Celebrate progress out loud so people know what “right” looks like.
59. Honesty scales when leaders go first. Name the hard thing and show how to address it.
60. Culture forms around what you tolerate as much as what you teach.
Execution & Accountability
61. Strategy stalls without a calendar. Put names and dates on intentions.
62. Start now. Ship one useful thing today. Ride the wave of momentum that follows.
63. Priorities aren’t what you say first. They’re what you do first.
64. When everything is urgent, nothing is important. Choose the one thing that unlocks the next three.
65. Inspect what you expect. Review, refine, and recommit in frequent loops.
66. Own the miss publicly and fix it quickly. Speed heals trust.
67. Scoreboards matter. People work smarter when progress (or lack thereof) is visible.
Faith, Purpose & Centering
68. Quiet time isn’t empty time. It’s where courage and wisdom refuel.
69. Purpose steadies the hands when the work gets heavy.
70. Gratitude turns pressure into perspective.
71. Servant leadership begins by asking, “Who needs strength from me today?”
72. Hope is a discipline. Practice it especially when results lag.
Leading Through Change & Uncertainty
73. Name the uncertainty. People handle the unknown better when it has boundaries.
74. Trade predictions for scenarios. Prepare for several futures, not just your favorite one.
75. Replan without blame. The map changes when the terrain does.
76. Communicate more than feels necessary. The vacuum of silence fills quickly with speculation.
77. Keep experiments small and reversible, so learning is fast and affordable.
78. Endurance is contagious. Your calm can be the team’s shelter in a hard storm.
Coaching & Talent Development
79. Grow people on purpose. Make development a standing agenda item.
80. Coach with questions that build judgment and ownership.
81. When you delegate the result, delegate the authority to achieve it. Authority and responsibility should be in balance.
82. Set intent and boundaries. Agree on check-ins. Then step back so the team can step up.
83. Size stretch work to the person’s readiness. Provide the right challenge, real help, and visible sponsorship. It’s okay if they reach the result by a different route than yours.
84. Build a bench before you need one. Succession begins on day one.
Supportive Organizational Behavior
85. Make it safe to disagree. Invite the view that challenges yours.
86. Credit ideas to their source. Recognition fuels contribution.
87. Write agendas as outcomes, not topics.
Systems Thinking & Process
88. Correct the mistake and improve the system that allowed it.
89. Turn recurring work into checklists and rhythms so excellence is repeatable. Then automate it.
90. Map the flow of work end to end. Prune any step that adds no value. Unblock the rest.
91. Measure what matters. Review it at a pace that improves the work.
Stakeholders & Customer Focus
92. Start with the customer and work back to today’s priorities.
93. Define success in customer outcomes, then align processes, metrics, and rewards.
94. Close the loop by telling people what changed and why.
Conflict & Courageous Conversations
95. Address tension early while the knot is small.
96. Separate the person from the problem. Aim at the issue, not the identity.
97. Put the real issue (the skunk) on the table. Agree on facts before you debate fixes.
Energy & Well-Being
98. Protect time for deep work and recovery so decisions are sharp.
99. Model healthy boundaries. Your example sets the team’s norms.
100. Choose a sustainable pace over heroic sprints. Consistency wins the long game.
Leadership is a skill to be learned and practiced over a lifetime. It grows through steady reflection, small improvements, course corrections, and new discoveries. These reminders pull us back to what matters when life and work get noisy.
Whether you lead a company, a classroom, a project, or a family, your influence reaches far beyond the moment.
The truest measure of leadership is the people we serve and the leaders they become.
Photo by Marcus Woodbridge on Unsplash – I love the idea of a lighthouse showing the way, standing firm and steady especially when the waves are their scariest.
It’s like having a guy working the door at a nightclub, deciding who or what gets in.
We assume we already know everything, so we stop listening. We nod politely. But inwardly we’ve already dismissed the person speaking. Or the article. Or the correction.
There’s often good reason for our defensiveness. Being wrong about something important can have real consequences. Our ego is trying to protect us from the genuine discomfort and potential costs of being mistaken.
The paradox is that the very thing protecting us from being wrong in the moment often prevents us from being more right in the future.
What if instead of having a bouncer who turns everyone away, we hired a smarter gatekeeper? One who doesn’t just protect us from being wrong, but actually helps us get better at being right?
What if we treat new information, even the stuff that contradicts what we think we know, as an invitation?
An opportunity to level up. To upgrade our understanding. To sharpen our thinking.
What happens when we level up? Our predictions start getting more accurate. Our explanations become clearer and more useful to others. We catch our own mistakes faster…sometimes before they even leave our mouth. We become more curious about the very areas we feel most certain.
The next time someone disagrees with you or presents information that challenges what you believe, pause before your ego’s bouncer slams the door.
Ask yourself, “What if they’re right? Can I learn something new?”
This doesn’t mean accepting everything that comes your way. But you can listen. Examine the ideas. Question them. Test them against what you know.
That’s true intellectual courage.
And it’s the only way to keep growing in a world that never stops changing.
“It is impossible for a man to learn what he thinks he already knows.” – Epictetus
I don’t remember a lot from Mrs. Olsen’s first grade class. One event that stands out is the day we planted a bunch of seeds in a garden. First grade Bob enjoyed digging in the dirt, making small seed holes, dropping each seed into its place, and writing the plant names on popsicle sticks that we plunged into the dirt next to the seeds.
Then came the bad news.
We wouldn’t be able to see the plants we’d planted until weeks later, and they wouldn’t reach maturity (whatever that meant) for at least a year.
To a first grader, weeks (and especially a year) meant forever. First grade Bob was extremely disappointed. I never saw the plants that came from the seeds we planted that day. It would be decades before adult Bob would go to the trouble of planting seeds or transplanting potted plants into a garden.
Recently, I watched an Essential Craftsman video where he planted 25 new trees. He worked the soil, designed a hand-made watering system, dug 25 holes with exactly the right spacing, brought in a truckload of special soil, mixed it with his existing soil, and then carefully placed each tree in the ground.
At various points in this multi-week project, he worked alongside his grandsons, his wife, and one of his good friends. He said that working with them over the years, especially his wife, had made him a better person.
The finished line of trees looked amazing and will look even better over the next 10 – 20 years.
He reflected that it’s easy to take for granted the shade we enjoy from trees planted decades before. The journey from seed to shade provider is a long one, but it always begins with the person (or Nature) planting that seed.
So, what kind of “shade” are we planting today? Is it the kind that shelters others through encouragement, love, wisdom, opportunity, or sacrifice?
The things we do now may not seem significant in the moment. They may never fully bloom while we’re around to enjoy them. A kind word to a child. A story passed down. A habit of generosity. A newly taught skill. A quiet act of integrity. These are the seeds we plant for the future.
Sometimes, like first grade Bob, it’s easy to get frustrated when we don’t see results right away. We live in a world that loves fast feedback and instant gratification. But shade trees don’t grow overnight. Neither do strong families, good character, or traditions worth passing on.
What if our job, the most important job of all, is to plant and build for a future we’ll never see? To create a little more shelter for the people coming after us?
Few will notice what we’re planting. But that’s okay. We do it anyway. And someone else will get to rest in that shade.
That’s the kind of impact I hope to make. Something that lasts beyond my lifetime, even if no one remembers exactly which trees I planted.
So I’ll keep planting. I’ll keep building. I’ll keep encouraging…investing in the people I know will grow far beyond me.
Because someday, someone will enjoy the shade I may never see.
Adult Bob loves that.
“If your plan is for one year, plant rice. If your plan is for ten years, plant trees. If your plan is for one hundred years, educate children.” – Confucius
I sat down recently to write a letter to my cousin (technically my first cousin once removed), who just started basic training in the Air Force.
What began as a quick note turned into something more. A personal reflection, a bit of a manifesto, and a stack of lessons I wish someone had handed to me when I was just setting out.
By the time I hit “save,” I realized this may be worth sharing with any young person taking their first real steps into the adult world.
The letter was full of life updates, jokes, birthday party planning, movie recommendations, and the occasional 10-year-old version of myself asking random questions. But the main message was you can do hard things, and you’re not alone.
What follows are some ideas that come from years of learning, leading, failing, and reflecting. These are lessons for anyone who finds themselves on the edge of something new.
Leadership begins and ends in your head. Most of your real battles are internal. That voice in your head? It can lift you up or hold you back. Especially in an environment full of rules and pressure, how you think will define who you become. Supportive self-talk, resilient thinking, steady choices. These are the foundational traits for leadership.
Start before you’re ready. Showing up takes more courage than people realize. You will rarely have everything figured out before you begin. Your best opportunities for growth will come from figuring things out while under pressure. That discomfort you feel is a sign that you’re on the edge of growth.
Do the next right thing. When life gets overwhelming (and it will), it helps to stop trying to solve everything all at once. Pause. Breathe. Do the next right thing. That’s enough. The bigger picture tends to take care of itself when we’re faithful and focus on the next indicated step.
You belong here. The feeling that maybe you’re not ready, or that someone else would be better suited for the challenge in front of you. That’s normal. But it doesn’t mean you don’t belong. The truth is you do belong. You’ve earned the right to be where you are. And you’re growing stronger every day, even if it doesn’t feel like it in the moment.
Respect is the foundation of everything. Not just the kind of respect that comes from rank or titles, but the kind you live out through humility, consistency, and quiet honor. When you offer that kind of respect, you build trust. And trust is what makes people want to follow your lead.
When the going gets tough, remember why you started. Every hard day will test your resolve. Every early morning, every setback, every lonely hour…these are the places where you’ll either lose sight of your purpose or anchor more deeply into it. Purpose doesn’t remove difficulty, but it gives meaning to the difficulty. And that’s enough to carry you through.
Discipline equals freedom. I shared this piece of advice that comes from Jocko Willink, former Navy SEAL, war veteran, and a powerful voice on discipline and leadership. He says, “Discipline equals freedom.” The more discipline you have, the more freedom you gain.
Discipline gives you control. Over your body, your mind, and your choices. Freedom to choose your future. Freedom to trust yourself. Freedom to follow through, especially when motivation fades.
You won’t always feel motivated. That’s okay. Stay disciplined. Show up. Do the work. That’s how you earn freedom. One decision at a time.
“Don’t wish it were easier. Wish you were better.” A classic quote from Jim Rohn. There’s no shortage of obstacles. The goal isn’t to escape them. It’s to grow strong enough to rise above them. The learning curve is real. Learn, adapt, overcome…become better and things will become much easier.
About those movie recommendations I mentioned earlier. It’s probably more accurate to call them story recommendations. Stories about honor, resilience, human ingenuity, and the willingness to keep going when things are difficult.
We Were Soldiers, an amazingly good movie about strategic servant leadership (which is my preferred style of management), bravery, and the love that comrades in arms have for one another. It’s a great tribute to the men who fought (many who gave their lives for the guy next to them) and their brave families back home. I think I’ve seen it at least 25 times and I’m happy to watch it anytime. Each time I watch it, I tear up in at least 2 or 3 places in the movie.
Ocean’s 11 and The Sting, two films that focus on creative problem solving and teamwork…though our “heroes” in these movies are con men and thieves.
The Princess Bride made the list. The value of honor (even among combatants), mixed with the comedic and spoofy scenes make it a classic. Even in a world of duels and danger, kindness, respect and loyalty still matter.
I suggested Seveneves by Neal Stephenson. A science fiction novel (my favorite genre for at least the past 10 years) about human survival, adaptation, and rebuilding civilization after catastrophe. The premise is that an asteroid causes the moon to shatter. What starts out as an oddity in the sky becomes a calamity as the moon breaks up into a ring and then begins to rain down to Earth (something they call the Hard Rain). Great sci-fi, lots of human ingenuity and adaptability, and a story that covers about 5,000 years. It’ll take some time to read, but it’s worth it.
Two books by Andy Weir. The first is The Martian (which became a movie starring Matt Damon), and the second is Project Hail Mary. Andy wrote The Martian in 2011 and self-published it on Amazon. It picked up fans and became a bestseller without an “official” publisher. His second book was called Artemis (takes place on the Moon). It was good, but not quite as good as The Martian (which is a high standard, so I’m probably being unfair).
His third book was Project Hail Mary. This one is also being made into a movie, starring Ryan Gosling. It is excellent.
The big thing about Andy’s books is that they are scientifically accurate. His characters deal with extremely complex challenges that require thinking and ingenuity to overcome. He writes in a way that entertains and teaches things you never knew.
I love that Andy wrote his first book from beginning to end without any publisher involved. Nobody was there to tell him what he was doing was the right thing. He believed in himself, believed in the story he was telling, focused on the work, delivered a high-quality product, and proceeded to find his audience one reader at a time.
All these stories reflect truths about the path ahead. Your journey will be hard. You’ll need grit, creativity, and perseverance. You’ll need others (family, friends, mentors, even strangers). More often than not, the tools to overcome life’s challenges will come from within yourself, quietly shaped by the stories you carry and the habits you form.
Whatever new thing you’re stepping into, whether it’s basic training, a new job, a cross-country move, or a new phase in your life, know that it’s okay to be unsure. It’s okay to feel stretched. Just remember your “why,” do the next right thing, and keep showing up with courage.
And who knows? Maybe decades from now you’ll be the one writing a letter like this, passing along what you’ve learned…
In high school, I had the good fortune of running cross country under a man named Mr. Smuts. Our coach and my 11th grade AP U.S. History teacher. He was the kind of leader who quietly influenced growth in those around him.
He didn’t bark commands or demand the spotlight. On race day, while other coaches were shouting themselves hoarse, Mr. Smuts would position himself at the mile markers. Calm, steady, present. As we passed, he’d simply call out our split times. No cheering. No panic. Just numbers.
We didn’t need anything else.
He had trained us so well that those times were all the feedback we needed. We knew what they meant. We knew what he expected. And we knew he believed in each of us (even the slow guys, like me).
When we crossed the finish line, sometimes ahead of the competition, sometimes not, he’d quietly remind us that the real opponent wasn’t the other team. It was the clock. It was ourselves.
That quiet challenge made us better. Not just as runners, but as young men.
Mr. Smuts embodied a rare approach to leadership. Seeing others more than being seen. His confidence in us was contagious. His calm became our calm. His consistency helped us believe that showing up and giving our best effort, day after day, was enough to grow into something exceptional.
For a bunch of teenagers full of energy and bravado, his presence could have been drowned out by flash and high school nonsense. But instead, we listened closely. We trusted deeply. And we ran harder.
His leadership style reminds me of a line from the Tao Te Ching:
“When the best leader’s work is done, the people say, ‘We did it ourselves.’”
That’s exactly how it felt. We crossed those finish lines thinking we had pulled it off on our own. Only because he had quietly laid the foundation beneath our feet.
True leaders create space for others to rise.
The Tao Te Ching calls it wu wei, effortless action. Like a river flowing around rocks instead of smashing into them. Doing the right thing at the right time and then stepping back to let the results take root.
Ronald Reagan once said, “There is no limit to what a man can do or where he can go if he doesn’t mind who gets the credit.”
This could have been written about Mr. Smuts.
He led in a way that called attention to others rather than himself. His approach shaped how we performed, how we grew, and how we learned to lead ourselves. His impact showed itself in the confidence he helped us build and the standard of excellence we still carry with us today.
The next time you find yourself in a leadership role at work, in your family, or on any team, ask yourself:
-Am I trying to be the hero, or trying to build others up?
-How can I lead with quiet influence?
-Can I let go of credit and trust the process I’ve helped shape?
The best leaders don’t stand in front of their people. They stand with them, sometimes just off to the side, calmly calling out split times as the race unfolds.
And when it’s over, they nod to themselves, knowing they’ve done their job.
The rest of the story: Mr. Smuts earned his doctorate in Leadership and became Dr. Smuts not long after my time at Cerritos High School (Class of 1984). He went on to become the school’s principal and ultimately the school district’s Superintendent of Schools for many years, before retiring in 2012. He continues to enjoy his retirement years.
Dr. Smuts is a leader who inspired (literally) thousands of kids (and adults).
This video provides a brief glimpse of this truly inspiring and gentle man in 2012 as he prepared to retire. It also highlights my high school campus that looks very much like it did four decades ago.
“Time heals all wounds,” people say when someone we love dies. It’s a phrase offered like a Band-Aid for a broken bone. Well meaning, but inadequate for the depth of what we’re facing.
For those who have lost a daughter, a son, a spouse, a parent, a sibling, a dear friend, the truth is something different. Time doesn’t heal. It changes things, yes. It allows us to move, to function, to smile even, but it does not erase their absence. That lives inside us, a permanent resident.
When I searched for quotes and stories from others who had walked this path before me (writers, psychologists, fellow travelers through loss), I discovered that my feelings aren’t unique or abnormal.
The bereaved across time echo the same truths I’m living.
I’ve heard that grief follows a pattern of denial, anger, bargaining, withdrawal, and finally, acceptance. That may all be true. It sounds like a clean process. Just a series of steps we must go through to get to the other side.
But that path has no clean endpoint. It can stall, restart at the beginning, skip and repeat steps while never reaching a conclusion. The grieving process never ends. We merely learn to function with our grief, and we do so in our own way, as imperfectly as we do everything else in life.
Author Jamie Anderson found words for what many of us feel but struggle to express: “Grief, I’ve learned, is really just love. It’s all the love you want to give but cannot. All that unspent love gathers up in the corners of your eyes, the lump in your throat, and in that hollow part of your chest. Grief is just love with no place to go.”
This captures exactly what happens when we reach for the phone to call them or save up a story we can’t wait to tell them. Only to remember a second later that they’re gone.
Grief isn’t a single event but a series of small realizations, each one a fresh cut.
C.S. Lewis, after losing his wife Joy, wrote about the persistence of absence: “Her absence is like the sky, spread over everything.” In his book “A Grief Observed,” Lewis documented what it feels like to live inside loss. “No one ever told me that grief felt so like fear. I am not afraid, but the sensation is like being afraid. The same fluttering in the stomach, the same restlessness, the yawning. I keep on swallowing. At other times it feels like being mildly drunk, or concussed.”
This is the lived experience of a body trying to process what the mind struggles to accept.
Joan Didion echoed this truth when she lost her husband, John Gregory Dunne. In “The Year of Magical Thinking,” she wrote, “Grief turns out to be a place none of us know until we reach it. It’s a foreign country with its own customs, its own weather, its own bewildering geography.”
There is no timeline. No tidy arc where pain transforms into peace according to some predetermined set of rules.
Dr. Lois Tonkin, working as a grief counselor in the 1990s, discovered a different truth about what healing actually looks like. A client whose child had died years earlier drew her a picture showing how her grief had initially filled her entire life. A small circle almost completely consumed by loss.
But over time, something unexpected happened. The grief didn’t shrink. Instead, her life grew larger around it. There was now space for new experiences, relationships, and meaning alongside the loss. This became known as Tonkin’s Model of Grief.
Like a tree growing around a piece of metal embedded in its trunk. We don’t absorb or eliminate the foreign object. We grow around it, incorporating it into our new shape.
This model shows us that time doesn’t diminish our grief. But it expands our capacity to hold other things along with it. Some days our grief surprises us with its suddenness. A song, a scent, a birthday or anniversary, seeing a classic car they used to drive. Other days we’re living fully in the expanded space around our grief, discovering we can hold both the wound and the wonder.
We must learn to carry the sharp pain of their absence while having gratitude for the gift of having known them at all. Our capacity to feel gratitude for the life we shared can provide much needed comfort, even though we’ll never stop missing them.
Some of the most tender truths come from those who’ve lost children. Elizabeth Edwards, who lost her 16-year-old son Wade in a car accident, offered this reminder, “If you know someone who has lost a child, and you’re afraid to mention them because you think you might make them sad by reminding them that they died, you’re not reminding them. They didn’t forget they died. What you’re reminding them of is that you remembered that they lived, and that is a great gift.”
Writer Megan O’Rourke, in her memoir “The Long Goodbye” about losing her mother, captured the peculiar contrasts of grief. “You look fine. You act fine. But inside, you are not fine. And you know it will never be the same.”
This is the hard reality of grief. The simultaneous existence of functioning and not-functioning, of healing and not-healing, of being okay and not-okay. We learn to carry both states, often within the same moments.
So no, time does not heal all wounds.
Time teaches us that we can be broken and whole simultaneously. That we can miss someone terribly and still find reasons to laugh. That love doesn’t end with death. It merely changes form, expressed as the very grief we wish we could escape.
In learning to live with our wounds, we hopefully discover something about ourselves. Our capacity to grieve deeply is evidence of our capacity to love more deeply than we ever thought possible.
And maybe that’s the real truth about time and grief.
“Blessed are those who mourn, for they shall be comforted.” – Mathew 5:4
“The Lord is near to the brokenhearted and saves the crushed in spirit.” – Psalm 34:18
Sometimes the hardest limits aren’t what we believe we are…but what we’ve decided we’re not.
Leader: I’m hitting a wall. No matter how hard I try, something’s stuck. Coach: Where? Leader: Connecting with my direct reports. The one-on-one meetings. All the details. I’m just not wired for any of it. Coach: You sure? Leader: I’ve never been good at connection. I’m not super technical. I’m not touchy-feely. I’m not a detail person. Coach: Sounds like you’ve got your “not” list down cold. Leader: Isn’t that just self-awareness? Coach: Could be. Or maybe you’re protecting yourself with that list. Leader: I’m not trying to be someone I’m not. Coach: Are you avoiding someone you could become? What if the growth you’ve been chasing is on the other side of “I’m not”? Leader: What if I do all that work and don’t like what I find? Coach: Then you’ll learn something real. But what if you find a strength you didn’t know you had? Leader: That feels like a stretch. Coach: Growth usually does.
“Ego is as much what you don’t think you are as what you think you are.” – Joe Hudson
We usually spot ego in people who overestimate themselves. Their arrogance and swagger enter the room before they do.
But ego has a quieter side. It hides in the limits we quietly accept. Not in who we think we are, but in who we’ve decided we’re not.
“I’m not technical.” “I’m not good at details.” “I hate public speaking.”
These negations, the things we distance ourselves from, might feel like declarations of strength and clarity.
But often they are boundaries we’ve unconsciously placed around our identity. Once we’ve drawn these lines, we stop growing beyond them. They protect us from challenges, discomfort, and the hard work we know will be required.
Leaders who define themselves by what they aren’t often:
-Avoid feedback that challenges their identity.
-Miss chances to adapt or grow.
-Choose the path of least resistance.
-Struggle to connect with different types of people.
-Dismiss skills they haven’t developed (yet).
If you’re feeling stuck, ask yourself:
-What am I avoiding by saying, “I’m not that”?
-What am I protecting by holding on to that story?
-What might open up if I let it go?
Sometimes the next chapter of growth begins not with a new strength, but with a willingness to loosen our grip on the stories we tell ourselves.
If you want to grow as a leader—or help others grow—it’s not enough to ask, “Who am I?”
You also have to ask, “What am I willing to become?”
I received an email from Noah Kagan this week. Not because we’re personal friends, but because I subscribe to his newsletter. Noah, the CEO of AppSumo, often shares practical insights and thought-provoking questions from his journey in the tech world.
This particular message stood out. He talked about being fearful for his 10-month-old daughter’s future. With all the chaos in the world, the deepening divides, the rise of AI and robotics, the general noise of modern life, he wonders what kind of world she’ll inherit.
But instead of spiraling into worry, Noah laid out how he’s choosing to respond: by creating clarity, limiting distractions, and doubling down on the things that matter most. He’s building a foundation, not just for his own peace of mind, but for his daughter to inherit.
His email reminded me of a quote often attributed to Mark Twain: “The future is in the hands of a generation that isn’t ready for it.”
We didn’t have AI, social media, or the internet back in Mr. Twain’s day. But even then, concerns about “the next generation” were nothing new. Parents, teachers, and elders across every era in history have wondered if the next generation is truly ready.
Noah’s concern isn’t just that the next generation might be unprepared. It’s that the world itself might be too broken to navigate well. But history offers some perspective.
Every generation has faced challenges. Wars, famines, political collapse, pandemics, technological upheaval, moral drift. And yet, the world moves forward. Somehow, each generation rises to meet its moment…even if their preparation feels lacking.
We don’t get to control the future, but we do influence it by how we live, what we model, and what we choose to pass on. We can’t predict what our children and grandchildren will face, or how they’ll respond. But we can teach them how to think, how to hold on to timeless values, and how to walk through hardship with strength and grace.
It’s natural to worry.
Let’s not forget that hardship doesn’t cancel out beauty.
Struggles don’t erase joy.
There will be triumphs ahead, too. If we’ve taught them well, they’ll learn to spot their small victories, celebrate them, and then pass along what matters to those who come after.
The future always arrives in the hands of the young—and the young are never quite ready. But then again, neither were we.
Grandpa Bob Encouraging Leadership 
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