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Jeff Pearlman, Best Selling Author

By, Chris Dessi

In the Spring of 1990 my big brother was Mark was heading to Villanova University. Mark was in the final months of a fairly remarkable High School career. He was a member of the National Honor Society. He was a straight “A” student. He was also Captain of the Mahopac High School football team. Not an easy act to follow by any stretch of the imagination. One afternoon that Spring, Jeff Pearlman a lanky classmate of my brother’s came to the house. Jeff was Editor-in-chief of the Mahopac Chieftain – the school paper. But that day was different. Jeff was there to interview my brother for a local “real” newspaper. Mark was considering walking onto the Villanova University Division 1AA football team.  This was big news. Well, at least it was big news in our tiny town. I’ll admit – it was exciting.

Jeff sat with my brother in his room to ask him a few questions. Like a good little brother, I crouched at the doorway and eavesdropped on every word.  Jeff took some photos, and ran the story. That visit to my home was the first real interaction I had with Jeff. Before that I had seen him for sure, but at three years older, our social circles remained distant.

As years passed, I learned that Jeff was penning articles for Sports Illustrated. Mahopac watched as Jeff’s star rose. Writing New York Times best selling sports biographies. Seeing Jeff’s work in the local Barnes and Noble was a thrill.  Later on we connected via social media. When I wanted to write a book of my own, I turned to Jeff to help edit and guide me. He even gave the book it’s title. Jeff asked that I speak to his journalism class he taught at Mahattanville about social media.  A real friendship was born.

My Father’s ALS diagnosis hit my family hard. Like any other good friend Jeff would check in from time to time. I’d get a message on Facebook at midnight. Simple. To the point. “How’s Dad?” Genuine. Caring. Selfless. Inquisitive. All the characteristics that make Jeff a phenomenal journalist. Also characteristics that make him a great friend. Like the time Jeff asked for my parent’s address. I thought nothing of it. Weeks later my Dad bragged about the autographed books Jeff had sent.

Jeff has a section of his blog called the “Quaz.” He calls it the “quirkiest, funkiest, Q&A series on the web.” I’d agree. It’s an insightful and wonderful piece of the internet that I never miss. A few years into Dad’s battle with ALS, Jeff expressed an interest in featuring Dad. He agreed. The resulting interview shook my family to it’s core. Jeff captured the torture of ALS from a man living it. Dad shared things with Jeff that only his close family knew. Jeff honored my Father, and produced (what has now become) a family treasure. When I decided to run the cancelled New York City Marathon in my own backyard to honor my Father, Jeff wrote about it on Sports Illustrated. Just weeks before my Father passed away, Jeff honored me and sent me questions so he could feature me in his “Quaz.” Before I could answer the questions, Dad died. I completed my answers to Jeff’s Quaz in the days following Dad’s funeral. It was a welcomed distraction.

Jeff Pearlman has close ties to the Dessi family. We love Jeff. His Quaz inspired these “success” interviews. Jeff is a great kid from the “mean streets of Mahopac.” Jeff is also a huge success.

Let’s do this.

Chris Dessi: How do you define success?

Jeff Pearlman: It’s a funny question. Back when I was coming up, first at the University of Delaware, then at The Tennessean in Nashville, my answer would have been something like, “Making it to Sports Illustrated” or “having an SI cover story.” Because, from the time I was in junior high, that was the dream. To write for SI. So success would be accomplishing my career dream. I mean, that’s all I knew. I was a pretty shallow person who aspired—more than anything—to be a famous writer.

And, while I’ve loved my career, what passed for “success” at 23, 24, 25 doesn’t hold an ounce of weight now, at 43. I mean, it’s laughable, and I actually feel bad for people who have this measure of success, via fame or money or title. And I look back with a little bit of shame (actually, a lot of shame), because in pursuing my vision of success I was, quite often, an arrogant, dismissive, listen-to-nobody dickwad of the first degree. I was so absorbed in the pursuit of what I considered to be greatness that I failed in 800 different measures of decency. jeff-pearlman-headshot-mobile

This is a long-winded answer to a basic request. For me, at 43, success means that tomorrow I’ll drop my son off at school, then return 20 minutes later to help the class with Friday morning spelling. It means rarely (almost never) missing a Little League game, a concert, a water polo meet, a play. It means knowing all my kids’ friends, making lunches in the morning, putting them to bed at night. And it’s weird, because the dickwad me of 24 sort of made it possible at 43 to have this life of a work-from-home (or the nearest coffee shop) writer. So I have to accept that.

But success, truly, is being an involved dad.

Chris Dessi: Your books largely follow successful (albeit in some cases controversial athletes) what pieces of success were you able to pick up from them if any?

Jeff Pearlman: Well, here’s the catch: Sports success vs. life success—it’s a TOTALLY different thing. In sports, to be great, you sorta kinda kinda sorta have to be a selfish prick. It’s weird, right? But the greatest athletes I’ve covered have—almost always—been selfish when it comes to workout time, when it comes to letting others in on their success secrets (generally, they don’t share much information), when it comes to contract negotiations. I’ve had this discussion with tons of high-level jocks, and—rarely by name—they admit it’s not first and foremost about the team. It’s about the contract, the endorsements, the headlines. Because a lot of these guys either come from rural bumblefuck or the rough inner-cities, and while it’s nice to say, “I’m all about helping the Chiefs win the Super Bowl,” the first priority is making as much coin as humanly possible in the short window that is your career as an athlete. And if you win, terrific. But if you don’t, generally, it’s digestable.

One guy I really studied, in this regard, was Barry Bonds. Forget the cheating for a minute. Bonds was as hyper focused as any athlete I’ve ever seen. Everything he did in his life was about hitting baseballs over walls. It was crazy to watch. I mean, obsession times 100,000. And he wasn’t doing it so the Giants would win. He was doing it to hit 50-plus home runs, so the team would pay him and companies would pay him and his family would be set for eons.

It ain’t sexy. But it’s reality.

Chris Dessi: You’ve talked about “hurting for journalism.” What advice do you have for today’s students and young professionals who have a passion for journalism? Any tips on how they can succeed today?

Jeff Pearlman: It’s a much more confusing ballgame than when I entered the workforce in 1994. Back then, the path for folks like me, Jon Wertheim, Grant Wahl, Howard Bryant, Jonathan Eig … name young sports writers from the time period, and we all knew we had to probably start at a newspaper, then (if it’s what you wanted) get hired by a magazine. That was the path—period. No Web, no Twitter, etc. But now, I don’t think many journalism students think, “I can’t wait to write for a newspaper!” I mean, jobs are dropping every other day, and who under the age of 30 even picks up a paper? It’s sad.

That being said, there are more avenues than ever. I mean, sooooo many more. Which is exciting. So how do you wind up at a good one that pays well? As far as I can tell, you do what has always been done by top-shelf writers. You outwork and out-write the competition. You find creative angles and ideas nobody else thinks of. You pitch everywhere. I’m not saying I’m anything special—because, truly, I’m not. But back when I was coming up at SI, I was a reporter (aka fact checker). We worked four days per week, which was sweet. Well, on at least one or two off days every week, I’d go to the office, close the door and call college sports information director after college sports information director, begging for unique/cool/funky story ideas. Before long, I had dozens upon dozens of them—and it’s how I got into the magazine so often. Was I a better writer than my peers? No. Did I have a talent they lacked? No. I just r-e-a-l-l-y wanted it, as badly as I wanted anything. So I busted my ass. That’s the secret to success that’s not really a secret: Busting your ass improves your odds dramatically. Jeff Pearlman

Chris Dessi: In a lot of ways your website/blog were ahead of its time. They are gritty, raw, honest and personal. On the one hand – today success is tied with transparency. On the other hand –  we live in a hypercritical world. Talk about your mindset to use your blog as this personal forum and also a little bit about how you deal with backlash on some of the more controversial issues you cover.

Jeff Pearlman:  I started the blog in 2008, sort of as a lark. Or, really, a vent; a chance to blather on about stuff. That was really it. But slowly, over the years, I’ve gained a bit of a following. Which is weird, but not weird. Weird, because I’ve blogged about everything from blood in my poop to a wrist wart that won’t go away to my Hall and Oates and Blind Melon obsessions. There’s nothing especially news-breaking or earth-shattering. But it’s not weird, because I think people dig the honesty and the funny little stories. My wife is a fan of reality TV. Not because it’s good programing, but because it’s an escape. Sometimes it’s nice to see what other people are doing to take the mind off your own life. Maybe that’s the secret to my website’s mediocre, have-never-made-a-cent-off-of-it reception.

Actually, one more thing: Being an unaffiliated sports writer allows me to do things Jemele Hill and Tom Verducci and most others in the biz can’t: Namely, critique the media. I have no corporate ties; jeffpearlman.com isn’t also an NFL rights holder. I can slam Jason Whitlock or Mike Lupica when they’re being arrogant asswipes, and the only blowback might be an angry e-mail. It’s ridiculously liberating. And fun. I never thought I’d enjoy blogging as much as I do. And, again, it has zero to do with the money. Because the pay is entertainment, and a chance to blog about Mr. T and Emmanuel Lewis and John Oates and the Alf puppet as often as I’d like.

Chris Dessi: Can you explain the impact, that social networking/digital media has made on your business/career and/or you personally?

Jeff Pearlman:  It’s very love-hate for me. So, as a guy who makes his living writing books, I need to be pretty active on social media. I need Twitter followers, Facebook friends. Because I need to show publishing companies I have a built-in following who will, hopefully, both spread word of a new book and buy it. Really, I’ve become a complete and total social media whore—with one eye always on building up as big a following as possible.

That being said, well, I love it. I do. Writing can be terribly lonely and isolating. There’s an amazing writer named Leigh Montville, and he once said something I’ve never forgotten: “A career writing books is like living in a cave for two years, popping your head into the sun for a week or two, then returning to the cave.” It’s perfectly said, because save for the short period of post-release sunlight, you’re a hermit. Twitter and Facebook—they connect me to people. I’ll do “Ask me anything you want” sessions on Twitter, get a few hundred questions about writing, and laugh when people thank me for their time. Thank me? Hell, thank you. You’re keeping me sane.

Chris Dessi: How much of your success was due to luck? Or are you of the mindset that you create your own luck?

Jeff Pearlman: It’s funny. There’s this whole debate going on about immigration in this country, and you have these self-righteous so-called patriots all but throwing rocks at illegal immigrants trying to live here. And you know why—99.9% of the time—the self-righteous so-called patriots live here? Womb placement. Seriously. They were born here because the woman who carried them in the womb was standing on American soil. THAT’S luck.

Am I lucky? Hell, yes. I was born to two amazing, supportive parents who paid for my college education; who allowed me to take their car to Urbana, Illinois in the summer of 1992 so I could intern at a newspaper for $5 an hour; who bought me a used car so I could spend the following summer interning in Nashville; who listened (or, perhaps, pretended to listen) as I read every high school newspaper story aloud on their bed; who encouraged me to pursue my dream; who raised me to be open-minded and to seek adventure.

Yeah, you create your own luck by working hard and making contacts. But my life, truly, is a joke. So many people in this world struggle in so many different ways. And, for no good reason, I’ve lived this blessed, charmed existence. I’m no more worthy than the 43-year-old Syrian refugee. Crap, I’m 8,000 times less worthy. But I’m here, sipping a cup of coffee at my kitchen table, my kids asleep upstairs. And he’s a refugee. It makes no sense.

Chris Dessi: If you could wave a magic wand, and change one thing about journalism – what would it be?

Jeff Pearlman: Speaking primarily (but not exclusively) of sports television, I would blow up the way networks treat women reporters. It’s disgraceful. Men can look like lumpy plates of tuna casserole and last in front of the camera into their 60s, 70s. If women don’t look like Erin Andrews, their odds of getting a prime gig on a huge network are, sadly, slim. And it’s a repugnant reality.

Chris Dessi: You’re books have become legendary for their exhaustive research – what’s your process? Or do you not have one – just diving in and going for it?

Jeff Pearlman: I appreciate the kind words, but “legendary” is probably a stretch.

A long time ago, when I was coming up, I read an interview with Gary Smith, the fantastic former SI writer. And he spoke of always making the extra call. I’d never thought of it as such. Hell, at the time I was a pretty lazy reporter. But the idea stuck, and now—when I write a book—I’m all about making the extra call, and the extra call, and the extra call. Take “Sweetness,” my Walter Payton biography, for example. The first thing I did was find all the old yearbooks and media guides he appeared in. I’d go through them, page by page by page, and make a Word file for everyone. Not just the stars. E-v-e-r-y-o-n-e. Every trainer, ball boy, draft pick, rookie free agent, coach, receptionist. And then, well, I call. And call. And call. I have this guiding principle, and it’s based around an experience I had in high school with a guy named Dave Fleming, who came out of Mahopac to wind up pitching for the Seattle Mariners. Dave lived about a half mile up the street from me, but we didn’t know one another. When he was a senior I was a freshman, and one day he happened to be on the school bus (maybe his car was in the shop). I was talking to a kid named Scott, and I asked him a trivia question—“Who was the leading rusher for the Los Angeles Rams in the Super Bowl?” And Dave turned around and said, “Wendell Tyler.” OK, does Dave Fleming remember that moment? No way in hell. But I do, because he was THE Dave Fleming. That’s how I think of these books. Were he alive, Walter Payton wouldn’t remember the 1978 free agent safety from Bucknell. But the free agent safety from Bucknell will remember being in camp with Walter Payton. And he’ll likely have a story or two.

That’s why I call everyone.

Chris Dessi: How important are habits and routine to your success?  What is your Rhythm? What time do you go to bed? Do you meditate?

Jeff Pearlman: I’ve never meditated, I probably get five hours of sleep most nights, I can’t run any longer because of disc damage in my back. But what I love—like, love, love, love—is the coffee shop. The rhythms and sounds and buzz. I mean, it’s my happy place. So often, when I’m writing, that’s where you’ll find me. Corner table, earplugs in (but usually no music), a cup of some overpriced nonsense by my side. I struggle writing in quiet isolation. I need people and the illusion of social interaction.

Chris Dessi: I speak with many successful executives that question the value of college. You have a degree from the University of Delaware, and you’ve been a college professor. What do you say to those detractors of education?

Jeff Pearlman: Well, I think colleges and universities are ludicrously overpriced, and it sucks that hundreds of thousands of Americans will be buried beneath college loan debt for years to come. It’s a gross system, and for some the question truly can be asked, “Is this worth it? Is it worth attending college if I’ll be paying it off until I’m 50?”

For me, it was beyond invaluable. Some of the greatest learning experiences of my life came at The Review, Delaware’s student newspaper. I made tons of mistakes; got fired, got brought back; was threatened with a lawsuit via an angry fraternity member; became editor in chief. There’s no way I enjoy this career without having spent long hours eating greasy pizza in the Review offices. So, as far as journalism goes, it’s pretty vital.

Chris Dessi: The first time I sat up and took notice of your career was when I read the John Rocker article. When did you first think of yourself as a success?

Jeff Pearlman: I’m not trying to sound modest, but my brain doesn’t work in those terms. I’ve got a lot of my dad in me. He owned his own executive search firm for years; had a great career. But I don’t think he ever settled; I think he always worried about what was coming, and why everything was about to collapse. It’s probably not such a great thing, but I have that in me, too. I’m always thinking what’s next, how can I survive, how can I make it and continue to write. Some people seem to think of themselves as stars. I don’t. I mean, not even close. Even when I got hired at SI in 1996. It was the fruition of a dream—but I didn’t consider myself as “a success.” I thought of myself as a guy who now has to prove himself to a whole bunch of editors.

Chris Dessi: Many young executives who read this blog struggle with work life/balance. You always put your family first. Taking them to school, getting very involved in their activities and sports etc. How do you strike a balance?

Jeff Pearlman: Well, I’m married to the greatest mother in America. Not just saying that—she’s insane, and she’s taught me an infinite amount about parenting, raising kids, maintaining the balance, etc. So that’s huge.

One thing is, I’m very motivated by death. It’s nothing to brag about, but it’s true. I think about death every … single … day. How my time is tick tick ticking away. I’m very aware with it, RE: my kids, and how fast they’re growing. I’m incredibly proud, but also sad. My daughter is halfway to 24—that blows my mind. So I’m hugely motivated by time, and not missing things. I think I have this belief that, if you’re around as much as possible, the clock moves just a tiny bit slower.

Chris Dessi: Who has been the greatest positive influence on your professional life? Tell us about that person.

Jeff Pearlman: I’m a bit of a broken record on this, but my dad. Truly. So here’s an example: Back in 1986, my dad wrote and self-published a business book called “Conquering the Corporate Career.” It was terrific, and he printed up, oh, 1,000 copies. And I remember being so dazzled; so proud. One day we delivered a bunch of copies to the Waldenbooks in the Jefferson Valley Mall. I mean, MY dad had a book on the shelves in a huge store. We’d sneak in from time to time (OK, all the time) and move “Conquering the Corporate Career” from the business section to the best-seller’s section—something I still do today with my books.

I used to think of my dad as Clark Kent and Superman. At home, he was Clark Kent. Un-athletic, not a good dresser, couldn’t cook, etc. I mean, tremendous dad. But … Kent. Then, come Monday morning, I’d sit on the bed and watch him put his suit on. Then the tie. And he was fucking Superman. Sometimes my brother and I would go to his office, and he was The Man. It was his company. I can’t tell you the impact that had on me. He had a dream, pursued it, achieved it.

Chris Dessi: What do you think is the one characteristic that all the successful people you know share?

Jeff Pearlman: I don’t see it. Success is just a really varied idea. Is the sanitation worker successful if he loves his job? Yes. Is the miserable hedge fund trader successful if he comes home at 8 every night and his kids greet him with a hug? Yes. Is the baker who never wanted kids successful if he makes the best muffins in Tulsa? Yes. I think it’s too simple to have “success” as this singular ideal or concept, because we all have different definitions. Some would look at me (and you) and say “That’s a successful guy,” others would say, “total flop.”

One thing I will say is this: The image of success is, often, bullshit, and harmful. When we look at others and say, “Man, if only I had that life …” we’re fooling ourselves. I’ve known many famous, rich, family-oriented people who were miserable. And I know a whole bunch of low-paid, unrecognized working stiffs who walk with a kick in their step.

Chris Dessi: As a Jewish journalist – have you ever experienced discrimination in the work place? How has that affected your outlook, and drive to succeed?

Jeff Pearlman: Honestly, I really haven’t had any issues. There are so many of us, it’s not like anyone’s discriminating.

Chris Dessi: You recently moved to LA from NY.  How much of that decision was based on your career? Or was it more of a “hey, why not?” move?

Jeff Pearlman: It had zero to do with career, 100 percent to do with the brevity of life. I’ve never wanted to be the person who spends his time in one place, forever. We lived in New Rochelle, N.Y. for 11 terrific years. Great friends, amazing neighbors, ties that will last. I mean, it’s as good a place to live as I know. But … personally, it was starting to feel stale. Repetitive. Did we do that thing two years ago, or four? Or five? Remember the party we had in 2009? Or was it 2011? Stuff blended. Jeff Pearlman

So I’d spent much time in Southern Cal, both for my Lakers book, Showtime, and doing Jim Rome’s show. And I loved it. The beach, the atmosphere. Everything. And I kept bugging Catherine, bugging her, bugging her. We even came out, and she liked it. Well, two years ago she was away for our wedding anniversary, but she left me a gift. And it was an old-school California Angels cap, with a note saying, “I’m scared, I’m nervous—but I’m in.”

Great wife.

Chris Dessi: You seem to have perfected the art of self deprecation on your blog – but here is your chance to brag a bit – what has been your greatest career success to date?

Jeff Pearlman: Chris, I never wear shoes. Seriously, never. It’s flip-flops about 350 days a year. And shorts—basketball shorts usually. And ratty T-shirts. It’s friggin’ sweet. Awards mean nothing to me. Like, less than nothing. I don’t care about being the best writer, or the best thing. I want happiness. And, for the most part, I’ve got it. That’s my greatest career success. Truly.

Rapid Fire

Chris Dessi: My daughters know that I hate witches  – what’s one thing that scares the hell out of you?

Jeff Pearlman: Whitewater rafting. Back in 1994 I had a truly terrifying experience, and I’ve never gone back.

Chris Dessi: Best day of your life?

Jeff Pearlman: Every Halloween.

Chris Dessi: Worst day of your life?

Jeff Pearlman: 9.11.2001—no close second.

Chris Dessi: Who is your hero?

Jeff Pearlman: My parents, Stan and Joan Pearlman

Chris Dessi: Oddest place you’ve been recognized?

Jeff Pearlman: I was taking the subway in New York, and I was on an escalator going down with my son; on the other side a guy was going up and he said, “Hey, you’re Jeff Pearlman!” It was weird, because I have a contentedly anonymous life.

Chris Dessi: What motivates you to work as hard as you do?

Jeff Pearlman: The love of doing it.

Chris Dessi: Name someone who knows more about you than anyone else in the world:

Jeff Pearlman: Catherine Pearlman, my wife

Chris Dessi: Most powerful book you’ve ever read that you recommend to everyone (other than the ones you’ve written) 🙂 ?

Jeff PearlmanThe Autobiography of Malcolm X. I read it when I was 18. Sheltered kid from a small town. Then—BOOM!


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This interview is one of 24 interviews included in an ebook called Just Like You 24

Just Like You: 24 Interviews of Ordinary People Who’ve Achieved Extraordinary Success.

This book is for the most driven among us.
If you have the hunger, drive and commitment to do more and be more, then you’ll love this book. Author and personal branding expert Chris Dessi set out to find the people that most inspired and captivated him, and uncover the secret strategies that anybody could use to become remarkable.
The result is Just Like You – a collection of interviews with those inspiring and captivating individuals where they share what they learned on their climb to the top.
Packed with inspiration, ideas and actionable advice on every page, Just Like You is a peek into the inner workings of some of the most successful people you’ve never met.
One constant source of inspiration was the author’s father, Adrian Dessi, who sadly lost his battle with ALS in February 2015. In his memory, 10% of all proceeds from this book will go towards funding research on combating ALS.

Order your copy for just $2.99 today.

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