A few months ago, I negotiated a contract for the kind of project that puts your heart on pause. Of course, I panicked and paced the length of my apartment. Who do I think I am? This can’t be real. I don’t deserve this. They’re going to find me out — me and my long con. I sat on signing for two days because self-doubt is a cruel specter that appears when you least want or expect it. It waits for your vulnerability, feeding on it, and lives to hurl a truck-load of salt on your open wounds.
We’ve all read about imposter syndrome, the denigrating interior monologues, the belief that we’re phonies who will be found out. We’re failures, incompetents, and blubbering fools — or so we tell ourselves. The irony that those who deal with crippling self doubt tend to be the highest achievers shouldn’t escape you. Even Einstein second-guessed his genius, purportedly confessing,
“The exaggerated esteem in which my lifework is held makes me very ill at ease. I feel compelled to think of myself as an involuntary swindler.”
Some argue that it doesn’t exist, that we’re right to experience self-doubt because we’re grappling with the reality of our limitations, that there will always exist things we know and don’t know and paralysis comes from confronting that fear.
Women experience imposter syndrome more often than men because we’re told, straight out of the womb, what we are and what we aren’t. I never conceived a woman would ever be president because we were told certain roles were solely relegated to men. This is your lane, stay in it.
We’re taught to recede, to stand behind, to support. We watch old shows and movies where women are diminutive and deprecating, where they pander to their beauty or folly. We tell our girls that they’re pretty before we praise their intellect, curiosity or artistic temperament. Even now, even after all this supposed change and time, women are still, in some respects, considered lesser than.
Years ago, I was an equity partner in a $20 million agency, and I would walk into a meeting with my team and executives would introduce themselves to the men who stood behind me because it was inconceivable a woman was running the show. I’ve seen women clearing conference room tables and taking notes. In comparison to my male peers who exhibited the exact same behavior, I was judged for being direct, aggressive when I should’ve been sweeter, a team player, accommodating. And I’m not the only one.
Perhaps I should’ve baked more muffins.
We’re told to ignore all the gender disparities if we want to be successful.
Women have to balance respectability with likability on top of all the actual work they have to do. The things we carry. The burden of assuming antiquated gender roles no doubt affects our ability to believe we could do big things, hunger for the world and everything in it.
I’ve had a successful two-decade-long career and I’ve worked hard for all of it. I’ve built companies, brands, and mentored hundreds of people. I’ve published two books and a literary magazine to acclaim and started an impact organization that aided disadvantaged women in Brooklyn.
And yet, whenever I start something new — an article, a book, or a new project — I’m in abject terror. Even though I’ve done what I’ve been asked to do hundreds of times, I still wonder: can I do this? Do I dare ask for this much?
I read somewhere that women won’t apply for a job unless they meet 90% of the criteria while men will apply if they have at least 60% of the required experience. I’ve built my career on overcoming fear. On paper, I was never 100% qualified for every single job for which I’ve applied. Instead, I was all about positioning and side hustles. I was hired for a marketing role in book publishing because I’d built and marketed a successful literary magazine online. I won a senior role at an agency because of my curious, non-linear CV.
I’ve never been complete on paper. Good luck fitting me into a box.
Feeling like a fraud doesn’t fade when you reach a certain level of success, in fact, it exacerbates it. And the people who mock it, who tell you to buck up, kiddo, should close all the doors behind them and take a stadium of seats because they are not you. Your feelings are valid even if internet fools poke fun at them at your expense.
1. I Keep a Brag Folder
I keep a brag folder on my computer. It contains a spreadsheet where I document my major accomplishments and minor victories. It’s a folder where I save emails from people that remind me my work matters. I matter. Whether it’s closing a major piece of business, helping a friend score a gig, or not backing down when a prospective client decides to play dirty during contract negotiations — I log the date, the event, and how I felt at the moment. I’ll even save related emails as proof.
A few months ago, I turned down an incredibly lucrative project because I was not comfortable with the IP language in the agreement, the fact that the wording left space for the client to reuse, republish, redistribute, or resell my materials. Even though I had a lawyer create a custom contract, I still wavered when I saw the redlines. In the end, I walked away from a potential six-figure deal because my work, what I value and believe in, is more important than a paycheck.
Last week, when I felt down and doubted my future because locked in your home 22 hours of the day will do that to you, I pulled up my brag file, re-read the emails I sent holding my ground, and I reminded myself that I’m stronger than I think.
2. I Remind Myself Of Every Time I Surpassed Expectations, Including My Own
Every time I’m faced with a new role or project where I’m not 100% in my comfort zone, I take inventory of all the times I wasn’t the perfect candidate on paper.
- What did I know about marketing business, diet books, and memoirs when I applied for an online marketing job at HarperCollins? Well, I didn’t know how to market luxury clothing and accessories when I operated a profitable online e-commerce site in 1999–2000. I didn’t know how to market literary fiction until my online magazine was featured in The New York Times and had a formidable level of traffic outside of the smart set. If I could do those things, I can market diet books online.
- Who was I — a senior manager — to approach the president of HarperCollins with content syndication deals with Disney, MySpace, BlogHer, and other online outlets? Who was I to sit at the table where only VPs and imprint publishers sat — even though the president invited me? Because I was the only person in the building who saw the future of the online space in 2006 and reached out to websites to see if they wanted content. Because what I was doing sold books.
- What did I know about taking a job at an agency when I spent twelve years on the brand side? I have many unkind words for my former boss, the CEO of the agency in which I worked, but he was brilliant at sales. Give him thirty minutes and you’d sign over the deed to your house. So, if I could sell a story about my experience, convince him that my varied experiences replicate working with a variety of clients at an agency, I should get the job. I got an offer the next day.
- What do I know about the medical field to perform a segmentation study on doctors and medical professors for the National Board of Medical Examiners? I’ve done the same kind of work for regulated industries — as long as I know how to research and read, I could do this and I did.
- How dare I roll into Columbia graduate school when I’d never taken a single writing class — I majored in finance and marketing — and aside from my cat, no one had seen my writing, much less workshopped it. I sent a stack of typo-ridden pages, stories that would ultimately find their way into my first book to the admissions committee. I got it because while I didn’t have a fancy English degree or connections, I wrote from the heart.
Using my brag file and inventory, I’d pitch myself on this new venture that made me doubt myself. I’d give Frank Lombardo-level pep talks. You can do this. You have done this. You will do this. Just do the work. Strap in for the wild ride. And if it took playing the Rocky soundtrack while signing contracts or starting a job, so be it.
3. I Focus On What I Can Control
The one true thing I know about myself, the one thing in which I have confidence, is my ability to tell stories. The mark of a confident writer is the acceptance of the unknown, of all the factors that are beyond your control once you dive in and wade your way through your fixation — the story you’re meant to tell.
For every new opportunity, I focus on what I know and play the rest as it lays. When I accepted the project with The National Board of Medical Examiners, I knew nothing about the medical profession or professors, but this is what I did know:
- How to research and where to get information on specific industries. How to vet the information.
- How to ask the right questions in the onboarding process so I can parse which studies are relevant for the work I’m doing.
- How to perform a segmentation study and interpret the results.
- How to design by-segment messaging strategies.
I was 75% there — all I needed to do was learn what I needed to know and partner with my client to fill in the gaps.
I’ll always panic right before I start something new, whether it be a new book or a consulting project. I feel overwhelmed by the largeness of things, so I immediately break down a project into digestible tasks. When I write a book, I break down the story and tackle what I can, day by day. If you only consider the whole, the possibility of you being subsumed by it is greater than you saying, ok, today I will do this one thing.
I break everything down to its component parts, and I’ll tackle each part knowing that I’m moving, albeit at a snail’s pace, toward the whole.
4. I’m Always A Curious Student
When someone says they’re an expert or a guru, I pause. Because there are experts who are open and receptive to the constant flow of information; they’re always learning and evolving while others are stagnant, defensive, indignant. The latter believe there’s nothing left to learn, that one’s role is solely that of the teacher.
I believe that everyone, regardless of age and tenure, is forever a student. There’s always more to learn. A yoga teacher once told me that the mark of an advanced practitioner is someone who returns to a basics class to re-learn the poses as if they’ve just experienced them. There’s no ego, no attachment, only humility and curiosity.
I see my life, my work, as a means of consistently returning to the basics and re-learning what I know and adding new perspectives to this knowing. The best teachers are the best students.
Here’s the thing — failure is part of the process. There will be books you will write that will end up in the bin. There are projects you’ll take that will be a disaster (I worked with a lawyer on a project and I will never take on a law firm as a client ever again), and it’s important to separate your self-worth from what you do because who you are is not what you do.
It took me forever to realize that.