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The Teachers We Never Choose | Wisdom for your weekend
Published 3 months ago • 6 min read
The Teachers We Never Choose
July 23, 2026
Dear Reader,
Greetings from Parkwood Studios in Almost Heaven West Virginia, where it's the peak of tomato season!
As you may know, I never hesitate to humble or embarrass myself for the greater good. This week's wisdom essay is no exception.
How I Lost a Client and Found Myself
Wisdom Lesson 77
Years ago, I made the biggest professional mistake of my career. It happened with the click of a mouse.
After meeting with a prospective client named Jacob, my colleagues and I exchanged a few internal emails, discussing how the meeting had gone and whether we wanted to pursue the work. For context, Jacob was a young, intelligent, highly confident wealth manager.
The post-meeting email was part of the process. This was always how it went. Sharing observations, ideas and perceptions. It was just our normal email debrief.
Or so I thought.
Believing the conversation was staying safely inside the walls of Maple Creative, I clicked Reply All and typed ten words I'll never forget.
Do we really want to deal with this pompous asshole?
I clicked SEND.
About ten seconds later, I heard it: heavy footsteps, rapid pace.
Our office hallway was usually filled with the ordinary sounds of work—phones ringing, quiet conversations, the hum of printers. But this was different.
Two of my Maple colleagues were sprinting toward my office, their footfalls sounding like a pair of Clydesdales charging through the building. Something was terribly wrong. They burst through my doorway.
“Skip..." One of them was nearly out of breath. "You copied Jacob."
The other finished the sentence I didn't want to hear. "You just called the guy a pompous asshole."
The room went silent. I stared at them.
Then at my computer screen.
Then back at them.
"Give me a minute," I finally managed to say. "I need some time to think."
My guts instantly twisted themselves into a thorny wreath of lead. My heart pounded. And I could feel sweat gathering across my forehead and upper lip. A faint ringing filled my ears.
Actually, I needed a lot more than a minute. We needed new business. Jacob had the budget to hire us. And I had just called him a "pompous asshole."
For the next ninety minutes, I did very little except think. And pray. Pacing around the office, I replayed the meeting. Mostly, though, I replayed what it revealed about me.
I was embarrassed, ashamed and just absolutely angry at myself. How could I have made such a huge gaffe?
Then I Picked Up the Phone
Around 3:15 that afternoon, I picked up the phone. Not an email. Not a text. A phone call.
Jacob answered immediately.
"Jacob, this is Skip from Maple. I owe you an apology. Have you read your email this afternoon?"
His answer was calm, “Yeah, I have."
I took a deep breath.
"Jacob, I insulted you, and I've embarrassed myself. I'm deeply sorry. For the past couple of hours, I've been soul-searching, trying to understand not only what I wrote, but why I wrote it."
Then I asked him a simple question.
"Would you please forgive me?"
Silence.
So I continued.
“Honestly... I think I'm the pompous asshole here. That's the only conclusion I've been able to reach."
"I need to adjust my inflated opinion of myself. I need to replace my judgmental heart with some genuine humility."
Finally, he spoke, "Apparently so."
There wasn't an ounce of sarcasm in his voice. Just honesty.
Then I asked one more question. "Would you meet me at the Marriott bar this afternoon? I'd like to apologize in person and buy you a drink."
Jacob declined, "Skip, I don't think I'm up for that drink."
Then he said something I have never forgotten.
"Apology accepted. And we can move past this."
After a slight pause, Jacob continued, ”But I need you to recommend another marketing firm. Obviously, we won't be doing business together anytime soon."
He was right. I had earned that consequence.
The Lesson Beneath the Mistake
Losing the account wasn't the hardest part. Facing myself was. For the first time, I couldn't blame anyone else.
What the email exposed wasn't Jacob. It was me. My pride. My arrogance. My judgmental heart. What I saw wasn't flattering, but it was honest.
That miserable afternoon became a turning point. It humbled me—and awakened something better.
Somewhere during that season of my life, I stopped looking for impressive people. I started looking for humble ones. I stopped chasing success. I became hungry for something far more difficult to acquire: character.
I found myself seeking out friends, especially other men, whose greatest strength wasn't what they had accomplished. It was their quiet confidence rooted in humility. Those became the mentors I wanted to learn from, the role models I aspired to emulate.
The Teachers We Never Choose
A few weeks ago, I sat down with my friend Rick Barron for a conversation on The Main Thing Podcast. Rick is 77 years old. He's served in Vietnam, survived melanoma, helped build the original Macintosh at Apple, and spent more than four decades navigating the highs and lows of Silicon Valley.
Near the end of our conversation, he said something so simple I almost missed it: "Failing is probably gonna be the best lesson you're ever gonna learn."
I've been thinking about those words ever since. Because Rick was absolutely correct.
Looking back, I no longer think of Jacob simply as the client I lost. I view Jacob as one of the teachers I never would have chosen.
His refusal to hire us hurt, certainly. But his willingness to forgive … that changed me. I walked away realizing I'd gained something far more valuable than a new client. I'd been given an honest look at myself.
It wasn't the gift I wanted. But it was the gift I needed.
Something for You to Consider
Reading this, you may have thought of your own "Reply All" moment. Maybe your ghastly mistake wasn't an email. It may have been something you said in anger. Or a decision you regretted. Perhaps a relationship you mishandled.
Whatever came to mind… Don't waste it.
I'm grateful today that I didn't miss what that miserable afternoon was trying to teach me.
It changed far more than my career.
It changed me.
Continue the Conversation
What's Life Trying to Teach You? ... with Rick Barron
The best conversations don't always end when the recording stops. Sometimes they keep unfolding in our own lives.
That was certainly true after my conversation with Rick Barron. We talked about failure, resilience, humility, and why some of our hardest experiences become our greatest teachers. I found myself reflecting on our discussion for days afterward. In fact, those reflections inspired the essay you just read.
Rick Barron shares enchanting, informative stories and insightful wisdom
One of the great joys of hosting The Main Thing Podcast is getting to meet remarkable people—and then watching them continue to create, serve, and inspire long after our conversations end. Here are two projects I think are worth your attention.
📖 Jake Harriman — “Rescuing the Idea of America”
Former Marine Commander Jake Harriman (Episode 131) explores what it means to rebuild trust, strengthen communities, and recover the ideals that bring people together. It's a hopeful, thought-provoking read for anyone who believes our best days can still be ahead.
I've always appreciated stories that ask big questions without easy answers. Emma's debut novel does exactly that. Set inside the world of the British Museum, Room 18 follows an art historian caught up in a daring plot surrounding the Parthenon Marbles. If historical fiction with a dash of suspense is your thing, I think you'll enjoy this one.
And if Emma’s name seems familiar, she’s part of our podcast crew. In fact, she designed the logo and much of the visual identity for our brand.
Meaning: an acknowledgment of one’s fault or error.
More than simply admitting a mistake, mea culpa is the willingness to take full ownership of your actions—without excuses, blame, or self-defense.
Origin: Latin - meaning “by my fault"
Rather than suffering from her mea culpa, Julie found the team responded with deep respect.
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My aim is to help people get a little better at life. Interviewing the wisest people I know, I distill and share their wisdom with you by way of a podcast and this companion newsletter. I invite you to subscribe and get 2 free editions per month.
Read more from Hi! I'm Skip Lineberg, a podcaster and writer.
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