The Vagrant

The Inner Journey of Leadership

  • Longlisted for BookPal’s OWL (Outstanding Works of Literature) Award

A few years ago I got a note from Dan Rockwell, asking if I might be interested in writing a book with him. I get a lot of notes like that. But this was Dan Rockwell! I immediately said yes, and we got on the phone. We’d never spoken before.

Dan described the premise he had in mind: a young man, up-and-coming executive material, who is unexpectedly fired and moments later has an unsettling encounter with a homeless man. Complications and catastrophes ensue as the young man basically loses everything: a modern-day story of Job, sort of. With a moral that centers on the word, “humility.”

As Dorothy Boyd says to Jerry Maguire, he had me at hello. Dan and I clicked instantly, I fell in love with the story idea, and that was that. This book is the result, and I’m still in love with it. I hope you enjoy it.


The Vagrant Reviews

“A lovely tale of humanity and humility, wrapped in a fast, engaging read. The Vagrant will spark leaders of every kind to reflect on who they are.”
Daniel H. Pink, #1 New York Times bestselling author of The Power of Regret, When, and To Sell Is Human

“A modern-day fable of self-reflection and transformation, in the spirit of Charles Dickens’s A Christmas Carol … sure to be a lasting favorite not only for fans of leadership but for anyone who loves a great story of fall and redemption.”
David Bach, 10X New York Times bestselling author of The Automatic Millionaire and The Latte Factor

“Every leader eventually arrives at a fork in the path. The easy road is seductive but leads to a crash. The tougher road—the road of genuine self-reflection—is the one that leads to lasting impact. The Vagrant is an excellent roadmap to that greater path.”
Nido Qubein, president of High Point University

“There is so much insight packed into this little story! The connections, themes, and implications are so subtle and so powerful, I wanted to slow down so I could take it all in—but it pulled me along, like a riptide of revelation, right to its astonishing conclusion. Now I’m reading it a second time—and taking notes.”
Dondi Scumaci, author of Designed for Success: The 10 Commandments for Women in the Workplace

“The most dangerous flaw a leader can have is the one they refuse to see. In this immensely compelling narrative, world-renowned leadership authority Dan Rockwell and master storyteller John David Mann bring us a tale of blindness and vision, fall and ultimate redemption—and in the process help us take a really good look at ourselves.”
Bob Burg, author of Adversaries into Allies and coauthor of The Go-Giver

The Vagrant has everything a great leadership parable needs: believable characters, vivid writing, and a fabulous twist that will stay with you long after you turn the last page.”
Ken Blanchard, coauthor of The New One Minute Manager® and Leading at a Higher Level

“While information is abundant and readily available, true wisdom is scarce and difficult to obtain. The Vagrant closes this wisdom gap, revealing that a leader’s past does not have to define his future.”
Orin Woodward, New York Times bestselling coauthor of Launching a Leadership Revolution, Inc. “Top 50 Leadership and Management Experts”

“Our opportunity to lead others is predicated on our ability to lead ourselves. This book may be the wake-up call you’ve needed your entire career.”
Mark Miller, VP High Performance Leadership, Chick-fil-A, Inc., Wall Street Journal bestselling author of Culture Rules

The Vagrant takes you on a journey of authenticity that will transform your leadership. If you’re ready to do the personal work, the journey starts here.”
Skip Prichard, national bestselling author of The Book of Mistakes: 9 Secrets to Creating a Successful Future and CEO of OCLC, Inc.

“A modern-day fable of self-reflection and transformation from two incredible storytellers. Mann and Rockwell will keep you on the edge of your seat from the first page to the last.”
Marshall Goldsmith, New York Times #1 bestselling author of What Got You Here Won’t Get You There, ranked “#1 Leadership Thinker in the World” by Thinkers50

“A compelling story, a surprise ending, and a powerfully valuable lesson along the way. The Vagrant is a great book from the dynamic duo of Mann and Rockwell.”
Jon Gordon, 10x best-selling author of The Energy Bus and The Carpenter

“Leadership starts with the relationship we have with ourselves. The Vagrant provides a compelling exploration of one man’s powerful journey of self-discovery. An inspiring and meaningful read filled with insights for anyone interested in becoming a more evolved leader.”
Betsy Myers, fm executive director of Center for Public Leadership at Harvard’s Kennedy School of Government, founding director of Center for Women & Business, Bentley University

“Spell-binding! Mann and Rockwell have made an invaluable contribution to leadership development in the contemporary world.”
Brandon Webb, founder of SOFREP Media, former head instructor at the Naval Special Warfare sniper school

“If you’ve had your fill of leadership books, take one more step with this one! The Vagrant teaches aspects of leadership I haven’t seen covered in anything else I’ve ever read. It will leave you with new questions and powerful insights that will stay with you long after you turn the last page.”
Beverly Kaye, Wall Street Journal bestselling author or Love Em or Lose Em, 2022 Industry Legend Award recipient, Institute for Corporate Productivity (i4CP)

The Vagrant gets to the heart of leadership in a fresh, powerfully engaging way. An inspiring read for any leader aspiring to lift their contribution profile to new heights.”
Douglas R. Conant, New York Times bestselling author of The Blueprint, former CEO of Campbell Soup Company, founder and CEO of ConantLeadership

The Vagrant is a fable you’ll want to read over and over, that will wake you up to the power of self-awareness. Dan Rockwell and John David Mann make us reflect on who we truly see when we look in the mirror and what may be holding us back. This book will inspire a transformation in all leaders.”
Hubert Joly, senior lecturer at Harvard Business School, former chairman and CEO of Best Buy, bestselling author of The Heart of Business: Leadership Principles for the Next Era of Capitalism

The Vagrant is an irresistible, powerful guide to getting to know yourself. As every entrepreneur knows, business success is all about relationships—and if you don’t know yourself, how on earth can anyone else get to know you, like you and trust you?”
Rabbi Daniel Lapin, president of the American Alliance of Jews and Christians, author of Thou Shall Prosper: The Ten Commandments for Making Money

The Vagrant is a gripping parable that takes you on a journey of self-discovery and leadership. Through the eyes of the protagonist, we are reminded of the importance of humility, empathy, and the value of each and every individual, no matter their status in life. This book offers a refreshing perspective on leadership and the power of human connection. It inspires us to look beyond the superficial and embrace the complexity of our fellow human beings. I highly recommend this book to anyone looking for a thought-provoking and inspiring read.”
John Ramstead, president of Alpha Principle and host of the Eternal Leadership podcast

The Vagrant is a cautionary tale that draws us to reflect not only on who we are but also how we are perceived. Without humility and teachability, we may tend to drift from one situation to the next, angry and wondering what happened. Want to stop self-sabotaging? Read this story! Its truths may seem harsh—but they will set you free.”
Stacey C. Jones, PhD, president of Tremendous Leadership

The Vagrant is a captivating and timely parable about a high-performing executive who has gotten caught up in his own success and failed to recognize those who played a part in it. Like the Ghost of Christmas Yet to Come in Dickens’s A Christmas Carol, The Vagrant reminds us how fatal it can be if we fail to honor those we lead. The Vagrantshould be required reading for any leader, at any stage.”
David Lykken, founder of Transformational Mortgage Solutions and host of the Lykken on Lending podcast

“A riveting, thought-provoking read that will stay with you, quite possibly for a lifetime. Everyone will recognize some piece of Bob in themselves, even if they don’t expect it—and I love being sideswiped by a story just when I think I knew the plot!”
Tara Rogers-Ellis, managing partner of Mojo, an award-winning PR/communications firm headquartered in Dubai

The Vagrant joins the ranks of true leadership classics—a quick, powerful read with lasting impact!”
Mike Linch, senior pastor, NorthStar church, host of the Linch with a Leader podcast

Excerpt from The Vagrant

Chapter 1.

YOU KNOW HOW THEY SAY, “I wouldn’t know that guy if I tripped over him?” Well, I actually tripped over him—walked right into his outstretched legs before I’d noticed anyone sitting there. And even then, I didn’t recognize him. I should have, but I didn’t. At least not yet.

I still wonder how things would have turned out if I had.

THE DAY STARTED OUT SO well. Everything was going my way. It was the last Thursday in April. I had been at Mercy Hospital for going on three years. Three excellent, auspicious, turbocharged years.

When I arrived the place was a mess. Riddled with inefficiencies, rife with redundancies, shackled by a dozen incompatible information systems that couldn’t talk to each other. I already had something of a reputation as a guy who could get things done, and I was determined to keep earning that reputation. “Whatever it takes!” That was my rallying cry.

It took me a full year just to chase down where all the biggest problem areas were, another to work out the solutions. Year three, which we were in the process of wrapping up, was for implementation: a hodgepodge of competing legacy systems, streamlined and compressed like layers of deli meat, integrated together and smashed inside a simple, friendly hoagie roll of a user interface. I dubbed it “the Hero Project,” both because of its structural resemblance to a sandwich and because it would allow our doctors to get their noses out of those old byzantine chart-keeping systems and focus on actually being doctors.

By this time, I was co-leading a department of forty employees, running everything from the help desk to software development and deployment in every ward and unit. Had an excellent relationship with my boss, Norman, the CIO. I was on my way to the top.

So it was no surprise, that sunny spring morning, when I was called up to the seventh floor. I’d been looking forward to the promotion for weeks. Except that what happened when I got there was very much a surprise. Biggest surprise of my life, in fact.

And thirty minutes later I was back down on the third floor, walking out of my office—no longer my office—carrying a file box with my personal effects. I hadn’t been promoted after all. That wasn’t why I’d been called up to the seventh floor. Quite the opposite.

I’d been fired.

Making that thirty-foot slog to the elevator was like drifting through a nightmare I couldn’t wake up from no matter how hard I tried. I’d never been fired from anything in my life. Something was very, very wrong with this picture.

It never occurred to me that the problem might be me.

I TOOK A SIDE DOOR out of the building to avoid being seen. Heading around a back corner toward the entrance to the underground garage, I didn’t notice the homeless guy sitting there, back to the wall, legs jutting out like sticks of driftwood.

He wore a dirty green wool hat and one of those orange Day-Glo construction vests, though most of the Glo was long gone. Gloves with the fingers cut off. How old was he? Impossible to say. Fifties, maybe? Or maybe he was only a few years older than me, just in terrible shape. In any case, these observations did not come until a few moments later, because, as I said, at first I didn’t even see him.

I tripped, took a tumble. My box went sprawling, all my possessions spilling out over the asphalt.

“Oh, for cryin’ out loud!” I yelled at him. “If you have to panhandle, go do it around the front of the building!”

Which was a ridiculous thing to say, of course. There was no panhandling allowed out in front of Mercy Hospital. It was only later that it occurred to me, he probably wasn’t even panhandling at all.

“Tripped . . . o’er yourself,” he slurred. Obviously the man was drunk, or out of his mind. Probably both.

“Actually, I tripped over you,” I muttered as I picked myself up and moved to collect my scattered things. “Which I wouldn’t have, if you weren’t sitting out here in the middle of the walkway!”

“You got . . . you got . . .” He was having a hard time getting out complete sentences. “Got in your way . . .”

“Me? I got in my way? WHAT IS WRONG WITH YOU, MAN?”

A few people stared at me as they walked by on their way to the garage. All at once, I realized how foolish I must look. There I was, my stuff scattered all over the asphalt, shouting at this poor bum. I couldn’t remember ever having felt so humiliated.

“. . . impediments . . .” he mumbled.


“Impediments . . . of the apocalypse they . . . fly on wings of . . . gold but it’s . . . an illusion—”

He broke off into a coughing spell, hacking so badly I thought he was going to heave up his lungs, but he kept on trying to talk. I barely caught the words: “volume . . . age . . .” and a third that sounded like “Sufism.”

Great, just great. A religious nut.

He held up one finger as he coughed, signaling me to hang on.

I waited. Why, I couldn’t have told you, but I stood waiting for him to finish saying whatever it was he had to say.

Finally the coughing subsided, and after a few wheezing breaths he got out one more word. “Cer’nty.” And with that, he slumped back against the building, as if fully spent from the effort.

Volume . . . age . . . Sufism . . . certainty. Impediments of the apocalypse. Uh-huh. Oh well, I told myself. At least he isn’t dangerous.

How wrong I was.

I FINISHED GATHERING UP MY THINGS, stuffed them back into the box, and headed below into the parking garage. On the way, I started feeling bad about having yelled at the man. It wasn’t his fault he was a derelict. Or you know what, maybe it was his fault, but I still felt bad for losing my cool at him.

Once I’d got my box into the car, safely stashed on the floor of the front passenger seat, I locked up again and hiked back out of the garage and around to the pavement.

He wasn’t there.

It took a few minutes, but I finally located him out behind the building, reclining in the shade of a dumpster.

“Hey, man,” I said. “Sorry I kind of . . .” Feeling suddenly awkward, I wasn’t sure how to end the sentence, so instead I reached into my pocket, pulled out my billfold, peeled off a spanking new twenty, and handed it to him.

He made no move toward the bill.

“Take it,” I insisted.

He reached out and took the bill, looking up at me as he did so—and that was when I got my first and only good look at the man’s face. There was something familiar about him, but I couldn’t quite place it. In fact, I was about to ask his name, inquire whether I knew him from somewhere, when he took me by surprise. He handed me back the twenty!

“You need this more than I do,” he croaked.

To be honest, I was speechless. “Fine, then,” I said, and I snatched back the bill. I didn’t feel great about it, but I jammed the twenty in my pocket, turned, and walked away.

In my defense, I was still reeling from the ten-ton catastrophe that had just been dropped on me, up on the seventh floor. Now that was an apocalypse, all right. Had to give the homeless guy credit, he was certainly right about that one.

I trekked back into the murk of the parking garage to climb into my car and take a moment alone to think. At my parking spot, I stopped.

The car was gone.

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