The F-Word: What Chelsea Handler and I Have in Common

I know, I know - you’ve read a dozen “Best Advice” columns. At this point you feel like you could write one yourself. It would go something like this:

-Treat every day like it’s your first

-Hire people who are better than you

-Learn to say no

-Ask for help

-Listen to feedback from your team

-There are no shortcuts; do the work

-If you’re not hearing “no” a lot, you’re not pushing hard enough

-Keep your word…

Valuable? Yes, but more a reminder of things you already know rather than an “Aha!” moment. So I’m not going to rehash the best advice I’ve ever gotten (though, for the record, it was from former Time Warner CEO Dick Parsons: “Leave a little on the table; the business world is smaller than you think and they’ll remember the gesture the next time you meet.”) I want to share instead the best advice I wish I’d gotten.

Last week, I went to the inaugural MAKERS Conference in Southern California. MAKERS is a living library of thousands of trailblazing women’s stories (www.makers.com) -- a project launched by AOL to tell the stories of both celebrated and unsung women pioneers. Begun before I joined the company, MAKERS is a source of pride for all who work there. The conference was a logical extension because, while the movement for women’s equality has made great strides in the last half-century, there is still a long way to go.

Midway through the first day, after PBS anchor Gwen Ifill’s conversation with Sheryl Sandberg about her new Getty Image project, after talks by Latina founder Christy Haubegger and Orlando Police Chief turned politician Val Demings, Chelsea Handler brought up the f-word. Not the f-word you imagine - but an equally loaded one: fear. She talked about doing standup, acknowledging that for most people, speaking in public is right up there on the fear scale next to facing a firing squad. Obviously, Handler got over it, but she shared the fact that it comes back to bite her when she least expects it. She described recently being backstage at Radio City Music Hall for the opening night of a four-night run. It was as friendly a room as you could have, filled with people who love her show, and yet she suddenly felt weak-kneed and dizzy: "There are different phases of fear, and I've experienced so many of them. You get fearful when you least expect it."

There it is – you get fearful when you least expect it, even when you are Chelsea Handler, even when you have done this a hundred times, even when you know your material, even when the room is rooting for you.

In my twenties, when I was a young magazine editor, I would practice story pitches before editorial meetings. That was the will-they-find-out-I’m-not-as-smart-as-they-think-I-am phase of fear. Over time I gained confidence that I was actually pretty good at this business of generating story ideas, matching them with the perfect writer, and putting together the right mix of pieces so that an issue was more than the sum of its parts. I breathed a giant sigh of relief that the days of tight chests and flushed cheeks were behind me, a hazy memory of that younger, eager to please self.

Fast forward 15 years and I’m working at a television network. I’d spent four years running long-form programming, overseeing 20 or so movies and a couple of miniseries each year. I got to take some risks because, truth be told, my team’s contribution to the schedule was not going to make or break the season. But the critics liked us, we won some awards, racked up some nice ratings – and over the Christmas holiday I was offered the job of President of Entertainment, overseeing prime-time. I had always been the first person to share my opinion in pilot screenings, but owning the schedule is a whole different thing. This was the I-don’t-know-if-I’m-up-to-it phase. I spent the entire vacation in a state of semi-dread, happy to have been asked to dance but afraid I’d turn out to have two left feet.

Jump ahead another seven years, and I’ve just left a job as CEO of a media company to join an ecommerce startup. I have traded my big, beautiful office for a work-station, and I am wondering how I’ll ever make a phone call again with someone sitting directly across from me and someone else sitting six feet to my right. As a lovely young Stanford grad walks me through the product roadmap, talking about SDKs and APIs, it is dawning on me just how much I don’t know about this new world I have joined. This is the am-I-too-old-to-learn-new-tricks phase of fear.

I could list at least another dozen moments in my career when the f-word took up a very visceral residence in my body -- and here is the advice I wish I had gotten: Fear is not something you grow out of. It is an active part of everyone’s professional and personal development. It may go into hibernation for periods of time but it will reappear, often when you least expect it. You can try to hide it, to deny it, even to avoid it – but there are big tradeoffs with that choice.

So, how do you deal with fear?

1. Acknowledge and identify it. Enough said.
2. Play out the scenarios in your head. What’s the worst-case scenario? Maybe it is truly disastrous, but most of the time the worst case turns out to be more about embarrassment, self-esteem or even ego than about full-on failure.
3. Think about what you’ll lose by backing down. If you let outcomes drive your behavior, you will only ever go where you’ve been before. You can lead a nice, safe life, or you can (occasionally) step up or step out to a high-risk opportunity that offers greater rewards.
4. Embrace the entrepreneurial world’s “fail fast” model as a personal credo. Sometimes the high-risk opportunity is a bust. Your assumptions turn out to be wrong, or you’ve underestimated the difficulty of the task, or you just blow it (the performance, the presentation, the assignment). Learn from it. Build a new, better plan. Move on. Fail fast for software developers means failing quickly and visibly, exposing a problem so it can be addressed, often with a simple fix. That personal failure you think you’ll never live down will fade in importance, especially when you weigh in the learnings, the fix.

One of the definitions of fear is “awe, reverence” – a very human response to the unknown, a very professional response to a big challenge. It signals that you take this moment seriously, know the risks, and care deeply about the outcome. Chelsea Handler summed it up perfectly: "Moments that you've dreamt about your whole life ... can really scare you. Then you go out there. And you do it…and you're okay."

Fear can be your friend and your guide: know it, understand it, own it…and step through it. You’ll be okay.

Photo: Susan Lyne at Cannes