Author, CEO & Founder

Learn More >>

I Brought 20 Hookers to Central America on Business.

In: Finding Your Voice

I sloshed on yet another layer of gloss, steering frantically with one hand while trying not to rear end a truck full of cows. I mean, what would I tell the Life Hooky group?

“We didn't pick you up at the airport in San Jose because, see, there were these cowsssssss.”

Even I would think I was making it up. And the only time I make anything up is when the chicken is overcooked, because what kind of person actually calls another person out on overcooked chicken?

But that's enough about farm animals. Stop making me talk about farm animals, okay? Did Susquehanna County put you up to this? Sometimes I feel like I'm the star of Sweet Home, Alabama, except then I remember I'm not Reese Witherspoon. And then I say fuck really loud.

Anyway, so I'm barreling down a Costa Rican highway, with one of my creatives, Jess, by my side the entire twenty-three-point-wrong-turn minutes from the hotel to the airport, unsure of what to expect. At one point we actually did that thing where we looked at one another (YES, while driving) and said,

“You realize we just brought twenty strangers to Central America, right? Strangers. Who we've never met before. To Central America. And we're responsible for THEIR LIVES.”

Which is a funny thing, really, because as someone who's never had kids, the most I've ever had to worry about is dropping an Apple product in the toilet. You pretty much know what kind of day you're going to have if you punt an $800 gadget into a pool of human waste water.

So while on one level we knew exactly what we were doing—the Life Hooky event was, after all, carefully planned through every last detail—on another level, the fact that these twenty strangers had actually arrived hadn't even sunk in yet. For months we'd been so busy going through the motions, planning the perfect gift boxes, writing the world's funniest slang section to include in our welcome guide, Googling “sloth bite remedy,” and going over Operation: Participant Thrown In Jail, that when the moment came to enjoy the fruits of our labor, it felt more like we were going into labor.

I'll spare you the ubiquitous birthing metaphor (surprise! starting a new company isn't actually the same as ejecting a human out of your insides), but I will say this: For someone who's much more “creative” than “logistical” (my favorite euphemism for ‘shit planner'), going through the motions leading up to the event was the hardest part of all. I've been running my companies entirely remotely online for years—usually without routine by design—and so I hadn't gone through the motions in years. At least, not any involving clothing and sobriety.

Did we have the right ratio of beds to rooms to participants based on whether they were in a double or single and if the last letter of their first name started with A-F? What about the vegetarians? And the two brave men who surely wouldn't want a sarong in their gift box? What if it rains? What do we donate to the school? How will we get the participants and the kids to interact? How much flour should we give the Nicaraguan woman whose empanada business we were helping to start? Why not gift her AN ENTIRE DUMPTRUCK FULL  OF FLOUR? (Answer: Because you have to get to the Nicaraguan woman's house by panga boat. And we didn't have a plan for Operation: Death By Panga.) And naturally other hard questions like what if someone cuts their finger off in a high-stakes game of Pinochle? Did they sign the waiver? DID EVERYBODY SIGN THE WAIVER?

In sum, I felt like I'd have an easier time organizing the Macy's Thanksgiving Day Parade. Jess, on the other hand, who's basically the poster child for planning, would bound into the room and announce stuff like, “THE LABELS ARE READY!” which slightly made me want to punch her while kissing her while renewing her contract until the end of eternity. Is this what Facebook meant by, “It's complicated?”

So as we barreled down the Pan American, blaring Sean Paul at anti-human decibel levels, we knew everything we'd worked for over the past year would amount to this VIM. Very important moment.

The moment when we'd slap on our fake moustaches (naturally there were fake moustaches) and jump out of the car screaming like lunatics and greeting twenty real-life versions of online avatars. The moment we'd violently shove any last minute doubts into our dress pockets. The moment we'd ooze (ooze? gross) as much confidence as possible to make everyone else feel at ease.

The moment when Life Hooky became real.

And real it became. As I drop, tucked and rolled out of the car, jumped up on a nearby piece of cement, and declared, “WELLLLLLLCOMEEEEEEE LIFE HOOOOOKYYYYYY!” I was met with a resounding, “WOOOOOOOOOOO!” followed by applause. Followed by half the airport wishing they were us, and half wishing they could harpoon us. Followed by beers on a bus, jokes about hookers (get it? life hookers?), and five days of connecting, laughing, learning, listening and by golly dare I say it, living.

Naturally this is the part where you're expecting me to sum it all up with one big, happy horseshit lesson about how all the planning was worth it (you can read the blog post where I made the very first announcement about Life Hooky) and “fight for your dreams!” but even if I did say boring stuff like that, it wouldn't be the lesson I'd share. Because you already know that stuff. We all know it's going to be worth it. We all know we should be fighting for our dreams. We all know that anything is possible.

What we don't know is the hard stuff.

The human stuff. The stuff we all secretly wonder. Stuff like, “Will they like me?” or “What if it's awkward?” Stuff like, “What if something goes wrong?” and “Is my best effort good enough?”

The stuff even the most confident of people wonder when they awkwardly leap onto a cement platform to welcome a group of strangers from all over the world.

But that's the thing about stuff you don't know:  You don't know.

But there's beauty in that.

Because while not knowing is messy, nerve-wracking, uncomfortable, horrifying and fucking nauseating…

…it's also the perfect excuse to get out there and surprise yourself. 

Because there, tucked in neatly between the messy, nerve-wracking, nauseating pieces of the hard stuff, you find the easy stuff.

The stuff you were meant to be doing. The stuff that feels right. The stuff you'll be proud to say you're doing with your life.

It's called your potential.

And even the best planner can't plan for it.

Your only choice is to slap on a moustache, take a deep breath, and let not knowing be the reason you showed up at all. 

Oct 21


The Greatest Form of Suffering of All: Inaction

Oct 21, 2010

Once upon a time, I was feeling stuck. If my suspicions are correct, many of you reading this might feel the same way right now. You can’t get motivated. You aren’t excited about anything. You’re tired all of the time. Lifeless. Indifferent. Apathetic. You’ve stopped caring—about yourself, about your goals, about the things you used […]

In: Finding Your Voice


Aug 22


If You Don’t Seem Capable…You Aren’t

Aug 22, 2015

The way you hold your wine glass. How leisurely you pour your words. The conviction found in your fork, as you slowly and quite deliberately raise each bite to your mouth, as if rushes were for commoners and you hold the greatest secrets of the universe right there in between your forefinger and your thumb. […]

In: Finding Your Voice


Jun 2


When You’re Scrappy, You Don’t Give a Sh*t

Jun 2, 2015

I like the term scrappy. I’ve always pictured some femme fatale bobbing and weaving and diving and contorting herself into any number of ways to get the one and only job done that she’s there to do: Win. It reminds me of my favorite Will Smith quote (oh, you don’t have a favorite Will Smith quote?) “The […]

In: Finding Your Voice


Jun 8


A Tiger Doesn’t Ask Permission of the Gazelles to Sprint

Jun 8, 2017

Stop giving a shit about the stats. So you don’t have any subscribers? Who cares—you don’t need subscribers to put your best work out into the world. You don’t even need a website. Just start. Surprise—I’ve had a few thousand people unsubscribe since I started doing daily emails. Guess what? I’m doing it, anyway, full […]

In: Finding Your Voice


Aug 15


How to Be the Most Confident Person At The Table

Aug 15, 2014

When somebody doesn’t buy from you, which are you thinking? “Man, I’m a loser”  or “Man, they’re a loser.”  Getting cocksure is the very first order of business. And if you don’t feel sure of yourself, you know what you need? Not more clients. You need to sit your ass down, read 100 books, grovel for the […]

In: Finding Your Voice


Oct 22


Your Opinion About Yourself Doesn’t Matter

Oct 22, 2016

Real talk: I think you’re a liar. A very, very convenient liar. I can call you that because we’re all in the same club. Because the thing is, when you’re out there doing creative work, and new work, and work that has no manager, no support team, no pat on the back, there are days when […]

In: Finding Your Voice


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