Screwing Up

A good man acknowledges his mistakes. An exceptional man learns from them.

We asked famous men (and average Joes) to answer the question, “From which of your mistakes did you learn the most?”

Some guys wanted no part of the question. “It hits too close to home right now,” one media mogul told us. A successful writer deemed it “way too fucking personal.” Others insisted that they weren’t nearly “introspective enough” to take it on. One man even claimed he’d never made a mistake. “I’m pretty much God-like in that way,” he quipped.

But plenty of men did answer the question, and they did so with breathtaking honesty (and, on occasion, some much-needed humor).

Behold, men admitting they screwed up…

“Drinking a third martini. Then talking.”
Randy Grim, dog rescuer

“I was born into shame. And that I perpetuated that shame was my biggest mistake.”
Duncan Roy, filmmaker

Joe Mcginniss, author

“When I was young, I was in a boys’ choir led by a serial pedophile, who was eventually arrested. After my own molestation, I stayed quiet, believing I was protecting myself. This was a terrible mistake and might have been the biggest lesson of my life, and my biggest regret. And so it was the subject of my first novel, what I learned from that mistake.”
Alexander Chee, novelist

“Assuming that when people ask me to listen, they’re wanting advice or a conversation.”
Austin Bucholtz, high-school student

“I watched my parents waste their potential in this world. They were both smart, talented, attractive, and educated. They both had demons that they could not control: drugs, alcohol, violence, anger. My mother ended up living in cheap motels and selling books door to door. My father was pressing pants in a clothing store at the age of 60. I learned from their mistakes; I swore I was not going to let my weaknesses dictate my future.”
Michael Kamber, photojournalist



“I used to approach acting with a very antagonistic attitude. I was very hard to get along with as an actor. It made working in film unpleasant, and it also hurt my performances… So, I stopped.”
James Franco, actor

“I have learned almost nothing from my many mistakes.
Jack Shafer, writer


“The absolute knowing that loss cannot be run away from, avoided, or covered up with distractions. I have learned that a man stands strong and tall in the midst of loss and allows himself to feel it completely and in the deepest parts of his soul.”
Robb Braun, motivational speaker

“A black diamond run on a ski hill is no place to show off to girls you don’t know.”
Vik Sahay, actor

“From being unfaithful to a woman I loved. It really woke me up to my confusion and my cruelties and my cowardice and how poorly I had lived up to my ideals. I really fucked up but I would not be the person I am if I hadn’t had that fuck-up to teach me. Hard fucking lesson, wish I’d been smarter but you can’t wish for a life you’ve never had.”
Junot Díaz, author

“I learned that I am NOT a mistake.
David Boyd, college student

Committing armed robbery. Going to jail. Selling drugs. Going back to jail.”


“I heeded the urging of my family and never told my grandmother I’m gay, persuading myself that a woman who had lived through the Great Inflation of the 1920’s, Hitler’s Berlin, the death of her father in a concentration camp, and separation from her firstborn son—a woman who then, having moved to a country where she spoke not a word of the language, went on to raise a thriving new family (and to speak flawless English)—would somehow not be strong or understanding enough to love her true grandson.
Michael Lowenthal, author


“Having a child before I was married or ready to have kids.”
Dave Winfield, Hall of Fame baseball player

“I learn daily from saying yes to things I can’t fulfill. I learn by cutting back and trimming and pruning, and staying closer to the vision of what really matters.”
Chris Brogan, President, New Marketing Labs and social media rockstar

“When I was really young, and we were moving into a new house, my parents asked me to bring some towels to the bathroom. I associated bathroom with toilet, so I flushed some down the toilet. I’ve learned from this experience, and have not flushed any towels since then. Also, in grade school, I saw how badly it hurt somebody that I was mean to. I never wanted to feel that again, so I try to be nice to everybody.”
Tom Riles, comedian

“I did cheat on a girlfriend once, and afterward I felt like the lowest, most mangy piece of bottom-feeding dog shit that ever lived. I told myself I’d never do that again, to anyone. And to date, I haven’t—not that I’m asking for any special commendation from N.O.W. for managing not to insert certain parts of my body into people/places where those parts shouldn’t be inserted. But still, that one indiscretion taught me that I never want to feel that low again. (My wife and I often joke that I’m far too lazy and disorganized to have an affair anywayall that call-screening, text message-hiding, and remembering what lies you told to whom about what you were doing with whom and when and at what time. Just tiresome.)”
Mark St. Amant, author

“I once thought that a junior-high bully who picked on me relentlessly could be shamed by my crying. It didn’t work.”
Will Doig, journalist

“The mistake of thinking that the pursuit of money is a loutish, foppish, and miserable existence. I discovered that, for most, it is those things, but that you can pursue financial gain in a manner that is sophisticated, caring, and with integrity.”
Kenneth Hughes, actor and producer

“From the mistake of anger.”
Brady Udall, author

The biggest mistake I made was not following my heart and losing a very good friend as a result. When getting married (for the first time), I was told to choose between inviting a female friend whom I had known for more than twelve years, or calling off the wedding. My friend had been a very important part of my life and knew things about me that no one else did. My fiance at the time believed that there was something more to our relationship. There wasn’t. I was told to make a decision between my friendship and my fiance. My heart told me to tell my fiance to kick rocks and grow up, but I didn’t listen and told my friend that she couldn’t come to the wedding. Today, I have an ex-wife and a lost friend. My heart told me to do the right thing, and I didn’t listen to it. That decision has haunted me for my entire life.”
Frank V., federal investigator

“The biggest mistakes I have made have come from not trying.”
Jamie Houghton, retired CEO

“Walking up to Boston’s Mayor, Tom Menino, and saying “Hey Barney” (as in Barney Frank). Oops.”
Dylan Leonard Brown, executive assistant

“Drinking too much and thinking that making a ton of money might make me less of an a-hole.”
Tom Matlack, co-founder of The Good Men Project

“Being mean to my friends.”
Cole Matlack, 5-year-old son of Tom Matlack

“I make the same mistake over and over again, so I’m not sure how much I learn. So I won’t recount the number of times I should have kept my mouth shut, should not have hit the button, should have made sure I wasn’t making a complete ass of myself before opening my mouth. I can still think of about a dozen examples and cringe. The lesson is easy—better to say nothing than to say the wrong thing, the stupid thing, the inappropriate thing, the thing that makes you look like an idiot. But I’m not sure I ever quite learn it.”
Peter Applebome, journalist

Expecting life to unfold in a rational way.”
Maer Roshan, magazine editor

Continued on page 2

Pages: 1 2

About Tom Matlack

Thomas Matlack is a venture capitalist.


  1. My biggest mistakes always come from misjudging myself and allowing my own respite or insecurity effect my thinking. Then feeling starved, and allowing myself to get too emotional, over that which I feel like I can’t have, and then getting angry, and saying ‘f*** it’ and being an ass because I think it doesn’t matter anyway.

    Great article. So many of the answers say it so well already.

    Oh, and giving the keys to my moving van to a drunk 21 year old blonde in the hilly streets of San Francisco last weekend, thinking she would be more entertained by driving, and not lose interest on the way back to the hotel room. Let’s just the whole evening was a big wreck.

  2. Rev. Matthew Smith says:

    Every time I’ve done something rotten; every wasted moment; every ruined relationship; every time I actively sabotaged my own dreams; all of these stemmed from believing that because I’m gay, the world’s hate meant that God hated me too, so I had better get with the program and hate myself.

    My greatest mistakes happen when I act like I still hate myself.

  3. Alternately funny, trenchant, chilling and just plain dumb. Great cross section of men and a delightful array of answers.

  4. I’m seeing so many mistakes that I’m still making. The biggest one being being less than my absolute true self. It’s an ongoing process.

    I am interested to see Alexander Chee’s response here. I just finished reading “Edinburgh” last week. It was stunning.

  5. David Josiah Harris says:

    i’m in no way strong enough or smart enough to run this life by myself. even with the wisdom of those who have come before me, making it meaningful is inconceivable. what do i know of life? all i really know is what it feels like, and i can try to avoid those feelings of disappointment, failure, guilt, self-loathing all i want, but it’s just like running from some shadow. i’d like to run toward something. something that will give my life meaning, hope, purpose and value. i guess that’s what this idea of being a good man is about; leaving a mark and being a positive influence on those i live with. but i know there must be more to live for than rowing my boat around in circles, trying to avoid crashes. i can’t really help anyone unless i have an idea of where we should be going. that’s why i put stock in this whole Jesus/God theory. it answers all the questions and then some, and when i follow it things work out. good enough for now.

  6. R L Pete Housman says:

    Anything you participate in building you can destroy. Building for all the work it takes is better- destroying is easier.

  7. Doug Williams, writer/editor says:

    The question almost assumes we learn our lessons — even if they require a giggleZillion repetitions — and I’d say no, we don’t learn from them all. Maybe we grow a bit from them and undestand ourselves more and set ourselves up better for life’s next crossroads. I’d say my toughest lessons clump into a category of failing to trust my own gut instincts and ending up reasoning my way into an unhappy or an unwise choice. Not to go all Zen about it, but the lesson I’ve taken — or struggle to take away from those times — is to heed that inner sense as best you can. And if you blow it, be sure you forgive yourself, too.

  8. Jim Parkevich says:

    Saw this one a few times..ANGER..out of control, raw, devestating my family.

  9. Arthur C says:

    Junot Diaz (see above) said it better than I ever could — spot on!


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