Matt Weiner’s Years of Pre-‘Mad Men’ Failure and Humiliation Will Inspire You to Persevere


As someone who spent a significant chunk of my 20s floundering around in different directions, attempting to figure out how to find meaning and success in adult life, nothing makes me happier than stories of artistic and cultural luminaries who struggled, sank, and despaired before finally hitting the jackpot. There’s hope for all of us, these stories of creative late bloomers prove.

Matt Weiner, who now lords his Mad Men secrets over the rabid, over-analytical press each season, is one such figure who truly started from the bottom. His account of early failure isn’t just the standard “rejected lots of times” tale. He actually endured extremely consistent naysaying along the way: turned down from undergraduate creative writing workshops, ignored and unselected by graduate film contests — even his first, self-made film was ignored by festivals and “unsold.” And it gets even more directly humiliating. His story in the book Getting There; A Book of Mentors, republished in Fast Company, includes this anecdote of having his poetry thesis read in his presence by an admired undergraduate professor:

I gave it to a humanities professor and he invited me to his house to read the work out loud. After the first poem, he told me to get out a pen and take notes. He began, “The infantile use of . . . The puerile . . . The childish use of . . . The cliché awkwardness . . . ” It was one humiliating cruelty after the next. And I had to write these insults down myself. I literally went through hours of this, poem after poem. He finally leaned over to me and said, “I think you know that you are not a poet.” I said, “I was not aware of that.”

Years later, when he finally set his sights on Hollywood, his experience reached something of a rock bottom, and he grew resentful and felt useless.

So for the next three years I stayed home and wrote spec scripts. My friends had day jobs, but I didn’t. My wife, Linda, worked hard as an architect and supported us. I attempted to shop my material around, but nothing sold. I got very bitter, seeing people I didn’t think deserved it succeed. It was a dark time. Show business looked so impenetrable that I eventually stopped writing. I began watching TV all day and lying about it. My mother would call me to drive my brother-in-law to the airport. That’s the kind of crap I was doing instead of being a writer. I felt like the most useless, worthless person in the world.

Even after things turned around and Weiner got steady work “punching up” comedy scripts, writing the Mad Men pilot in his spare time, the parade of rejections didn’t end. The rest of the story we all know already: Mad Men got him hired by The Sopranos‘ David Chase, and he carried the script with him for seven years and many rejections. At last, when he finally got picked up by AMC, everyone basically laughed in his face. “I was so excited — but at that time no one thought AMC was, in showbiz terms, a ‘somebody,'” he writes. “Everybody felt sorry for me. I can’t even tell you the pity I got. It was as if I were taking my project and screening it in someone’s basement.”

I find Weiner’s current controlling persona — demanding no spoilers from the press, refusing to cut “coming next week” ads that make sense at all — irritating and mockable at times, but when you read his story, it’s hard not to acknowledge that he’s earned some of his right to be a diva. And his story certainly adds depth to his show’s fixation on workplace humiliations, firings, creative ruts, and stunning comebacks.

I spend a lot of my time talking through rejections with my fellow creatives online, even participating in comforting pity parties on Facebook, but I have yet to come across a story as terrifying as Weiner’s in-person drubbing by his poetry professor. If he could keep going (albeit in another genre; perhaps the message about poetry was received) so can we all. As he writes, “Rejection enrages me, but that ‘I’ll show you!’ feeling is an extremely powerful motivator. I’m at a point now where I’m afraid that if I lose it I’ll stop working.”