Author, CEO & Founder

Learn More >>

If You Feel Like a Big, Fat Imposter Who Doesn’t Deserve Anything and Worries About EVERYTHING, Read This. It’s a GOOD Thing.

In: Feeling Dead and Uninspired, Feeling Disillusioned With Life

I'm writing this from a place that could almost be mistaken for the Italian countryside, were I not surrounded by lizards and toucans and bullfrogs the size of a fucking dinosaur.

Rather, I am high up in the hills of Central America overlooking the Costa Rican valley from my squishy, pancake lounger—it sort of reminds me of a bloated fat cat—while four other guests—two delightful gay couples—breast stroke around in the swimming pool below me and ponder how much it would cost to hire a private driver for the year. $20,000? $30,000? I wonder what they have done with their lives that has put them in such a privileged position to even ask a question like that.

Of course, self-important beast that I am, my thoughts quickly turn to my own life. Because aren't we always trying to triangulate who we are based on who everybody else is? I think about whether or not I could hire a private driver; whether I would even want one. It immediately strikes me as undesirable, and then straight-up scary to realize that something so pompous might fall squarely within my means. Who am I? Who is this middle-aged woman I'm becoming? (Note to self: never refer to self as “middle-aged” again.) Every day I am drifting farther and farther away from my original identity; every day I'm less and less the girl I grew up knowing. The narrative keeps changing. I keep evolving. And I am always someone I hardly recognize.

This is both reassuring and terrifying.

Reassuring, because I'll never have to experience the shame of need again, like I did when I was young. Terrifying, because metamorphosis, by definition, requires that you constantly become someone you weren't before.

I am never the same person, anymore, as I was five minutes ago. In that respect, I am always a stranger to myself—which can be a little disconcerting, but also the adventure of a lifetime. Having the opportunity to get to know yourself over and over again through a new lens gives you many chances to make things right with yourself. Growth feels like your mind is constantly a visitor in a foreign country—and maybe that's what I like about it. It can be a lonely place where you won't always speak the language, but that's part of the thrill: it is better to feel like an imposter in China, than a native in your living room. Home may be comforting, but comfort will always keep you small.

I suppose this is why I have come to love imposter syndrome—the nauseating feeling that we all get when we're exploring new lands. Unlike physical lands, however, these lands are mental. Starting the business. Stopping the business. Charging more money. Charging less. Taking the leap. Saying fuck yes—or no. Doing the thing. And being okay with not knowing what's going to happen afterward, or who it'll make you in the process.

I have come to think of every new experience as a new country to explore, and of course it's not going to feel natural. Of course you're going to feel like an imposter. It'd be bat shit crazy if you rolled up in Egypt all, “Yup, feel right at home!” Difference is going to make you feel different—and that applies to anything you try in your life and your work and your business and your everything. And what a wonderful opportunity, we all have, to feel that divergence. It is the opposite of stagnation. This is how, and when, we feel alive.

Imposter syndrome, then, is a sign of life. It's like the heart monitor you hear in the ER. It's a signal that you're not just rotting away in your living room along with the rest. You are a living, breathing, moving, learning, exploring, growing, wild, free-range human being—and yeah, that sound in your head is annoying, but it's also really important. Without it, you've flatlined.

As I sit here in Central America today, I feel whole, I feel challenged, and I also feel triumphant. I have just come from a month-long solo trip to South America; to Chile, where I learned how to harvest grapes on a vineyard outside of Patagonia, took drawing lessons from a Chilean artist in Valparaiso, did a photoshoot in the city with two renowned photographers, consulted on a famous soccer player's new business venture, worked with the U.S. Embassy to help nominate leaders for a new exchange program, helped a friend solidify her business plan as a freelance consultant, visited local businesses and craftsmen and artisans to see what kinds of interesting things they're creating, went to the ballet (and snuck in a Negroni in a mason jar), hiked through a new forest, had coffee in a stranger's home outside of aforementioned forest, did a private wine tasting in the offices of Calyptra vineyards (highly recommended if you've never had), explored all-new neighborhoods on foot, and celebrated THE BOOK DEAL around a bonfire with old and new friends alike—a Peruvian chef, a photographer from France, a student from Germany, a brilliant plastic surgeon, a diplomat, a robotics engineer, and several other entrepreneurs and politicians and creatives. And guess what? ALL of it made me feel, even if only momentarily, like an imposter. Who am I to harvest these grapes I know nothing about? (And what if I fuck it up?) Who am I to pick up a piece of charcoal and attempt to draw this teapot? (And what if I fuck it up?) Who am I to say what a world-famous soccer player should or should not do with his new digital business model? (And what if I fuck it up?) (Okay, fine, THAT I won't fuck up, because #EXPERIENCE.)

But could you imagine if I didn't do any of it because I was worried I'd look like a giant, ignorant douche rod?

Could you imagine if all I did was stay in my Airbnb and walk to get a coffee and keep my head down and try not to get robbed?

By doing the hard, we do our best.

There is so much richness in this life that we're all missing out on, every single day, because we're afraid we're going to fuck it up and look stupid and make giant a-holes out of ourselves. But the most embarrassing thing of all would be in letting your life pass you by without having any good stories to remind you who you are. It's not about the money or the recognition or the list of accomplishments you can put on your belt: it's about how your life has made you feel.

How do you want your life to feel?

My advice: chase imposter syndrome like the sun. Do everything that makes you second-guess yourself twice. Find the strange and the unusual and the uncomfortable and the new, and let her show you your own potential. Be brave enough to walk blind. Don't ask too many questions. Don't ask any, in fact. Stop censoring your own experience on this earth. Your safe harbor is only an illusion, anyway: at some point, we will all have our lives turned violently upside down, and your only defense is diversity. Diversity of experience, of relationships, of passions, of knowledge. When your soul knows many things, it is no longer afraid of loss. You can become a new person in the next five minutes. You can be someone you hardly recognize, anymore, and you can be okay with all of it.

Imposter syndrome isn't what we should be scared of: it's not feeling any at all.

The worst thing we can do is be afraid of looking silly, for it comes at the cost of our life.

Jan 15


Your Life in 6 Words.

Jan 15, 2013

Remember that one time I got loose, drank too much eggnog* and packaged everything together in the TMF store for a wild, wild west of a discount–and then told all continental U.S. buyers that I’d even take it a step further and send a surprise to their doorstep? Right. That time. Just last month for […]

In: Feeling Dead and Uninspired


Jun 9


The World Isn’t Your Mommy

Jun 9, 2017

You know what’s crazy? There’s not actually a team of people assigned to your life, sitting around monitoring your blood work, and your bank accounts, and the health of your relationships, jotting down notes, circling areas of concern. There’s no supervisor. No one checking your progress. No one setting quarterly reviews. As a result, we […]

In: Feeling Dead and Uninspired, Feeling Disillusioned With Life


May 18


When You Feel Like a Hot Mess Full of Walking Contradictions and WHO ARE YOU AND WHAT IS YOUR LIFE?

May 18, 2017

You don’t have to choose, you know. You can be intelligent…and sensual. Extroverted…and introverted. Complex…and simple. You…and someone who’s evolving into someone else. Sometimes, in an effort to finally define who the fuck we are, we start putting ourselves into the little boxes voluntarily—the same ones that we spent our earlier years trying to escape. […]

In: Feeling Dead and Uninspired, Feeling Disillusioned With Life


Nov 5


Where’s Your God Damn Pineapple?

Nov 5, 2012

There’s always a reason why you shouldn’t. Shouldn’t spend the money. Shouldn’t be so frivolous. Shouldn’t miss work. Shouldn’t be irresponsible. Shouldn’t act so hastily. And a million other reasons why you shouldn’t do what you’ve been wanting to do. The real question, of course, isn’t whether you should or you shouldn’t. Because when it […]

In: Feeling Dead and Uninspired


Jan 30


The Numbers Don’t Mean Jack.

Jan 30, 2013

Hi.  It’s me, Ash. Was that obvious? I’m sorry to pardon your regular programming, but today we’re going to talk numbers. I hate numbers–you can go square root your mom. But sometimes, you’ve got to look at ’em. You know…like when it’s tax season. As you may remember, in 2011 I publicly showed the world how to make […]

In: Feeling Dead and Uninspired


I'm a Bad Influence on Women

Hey, I’m Ash! Twenty years ago I was a small town girl growing up in a trailer park in rural Pennsylvania. Fifteen years ago, I lost my family and everything I knew right as I became the first to graduate college. Fourteen years ago, I found myself leaving everything behind for a new life in the city where I could be “normal.” Ten years ago I realized normal was the most disappointing thing that ever happened to me. Nine years ago I quit my job in advertising and pursued my dreams as a creative writer. Eight years ago, I built a 6-figure business doing what I love using nothing more than the Internet and my voice. And now, today, I’m the founder of The Middle Finger Project, an irreverent media co. that helps other women find their voice and teaches them to use it to build whatever the f*ck they want to. With a book coming out with Penguin Random House in February 2020 (YASSS, WE’RE A PRODUCT IN TARGET!) I’m proud to be a bad influence on women and guide them into doing something disobediently brave with their life and their career.

Enter your email address and I’ll send you my advice column every week sharing everything I’ve learned—and so much more.

But no serial killers. I promise I won’t send those.

Privacy Policy Info Here