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Through All the Fuck-Ups, I Was Right About One Thing: My Someday Would Be Different

In: Finding Your Voice

I have no business being rich. I grew up curling my bangs in a trailer park, using food stamps to buy popsicles, dating boys who milked cows, bringing boom boxes to stone quarries, and thinking tinted car windows were the ultimate sign of prestige.

If you made a sitcom hybrid of My Name is Earl, Roseanne and The Office, you’d find my 15 year old self waving awkwardly from the back of somebody’s blue pickup truck—except probably literally, since The Office takes place in Scranton, Pennsylvania, and I’m actually from nearby.

My relationship to work, and my ideas about what adults did for work, was distorted at best⎯royally catastrophic at worst. My mom had me when she was forty years old, on the heels of her own mother’s death, when my Philadelphia Police SWAT team father left a note that said, “I’m sorry, I can’t do this.” It spun her into a downward spiral of anxiety, depression and more anxiety, ultimately ending in nervous breakdown and, several years later, a statement from a judge saying she was legally unable to work. She was disabled by crippling anxiety.

We lived on a combined monthly income of $567 from Social Security Disability, $200 from Sergeant Brian F. Morris in child support, and a couple hundred bucks she got for holding the mortgage on the sale of her mother’s home⎯the one that she sold when things got really tough. When we were living on less than $9,000 a year. When we moved into our first trailer. And years later when we moved into our second trailer, too.

She’d spend her days holed up reading John Grisham, sampling cocktails of prozac and the lorazepam, tenderly caring for her tomato garden and spending her afternoons napping.

I loved her, but that didn’t stop my fourteen year old self from seeing her as a coward. Her anxiety seemed like a bunch of smoke and mirrors⎯an excuse to be lazy, weak, incompetent, and embarrass me in front of my friends.

Why can’t you just get a job? I’d yell, annoyed when I’d see her struggle to pay the heating bill one day, and the next stroll in the door with a forty dollar carton of Marlboros. We had Marlboro sleeping bags, Marlboro thermoses, Marlboro coolers. Apparently when you buy enough forty dollar cartons of cigarettes, you end up with an unnatural supply of red and yellow camping gear, courtesy of rewards points. Points my mother would try to get me excited to “cash in” as she flipped through the official Marlboro magazine, hoping to ease my disapproval. But my disapproval only grew. It was bad enough she was killing us both with those things. Did she have to get a fucking prize for it?

I hated living in a trailer. I hated sneaking out the back door and walking around the block to show up at the bus stop from a different street, hoping no one would guess where I really lived. I hated feeling like it was a prison sentence, that my place was in the world had been decided by something entirely outside of my control, and, most importantly, that I’d never have a staircase. I desperately wanted a staircase.

In the 6th grade, a boy named Craig got up on a chair and announced to our classmates in a singsongey voice: “Ashley lives in a trailer! Ashley lives in a trailer!” He sang it like a song, every word carving a bitter promise into my heart that this place in the world wouldn’t be my place. I would be better than the two-story, two car garaged Craig’s of the world. And I’d prove it. Someday.

It was six years later, when I first heard about the interview, that my someday began.

We were instructed to arrive at Penn State’s Main Campus and bring a tangible object⎯nothing more, nothing less. No resumes. No frills. No kissy ass moves. Just the object. He sat in the far corner of the room⎯no clip board, no notepad, no smile. I was seated near the door, at a table, with a woman named Carol opposite me. I was told to address Carol, not the man in the corner. I trembled as I pulled the box out of the garbage bag. It was a brown cardboard hexagon-shaped box. One I had bought at a craft store two weeks prior. One I had labored over. Sweat over. And one that I hoped would serve as a form of life insurance. Life insurance for my future.

“This,” I started, pointing at a scanned, shrunken newspaper article that I had pasted to one side, “was the stone wall I built for my friend Jill.”

Carol’s face remained indifferent.

“She died in a car accident when we were in middle school.”

I slowly rotated the box. “And this, over here, is when I led our volleyball team to a district championship as Captain.”

“I bet your mother was very proud,” Carol interjected.

“My mother never saw me play volleyball.”

I quickly glanced away and continued on with my carefully planned monologue, pulling a second box from inside the bigger one. Another hexagon.

With each turn of the box, I listed yet another arbitrary achievement⎯Honor Society President, Student Council Secretary, Yearbook Staff⎯before pulling out an even smaller hexagon box and rattling off more of the same. I had spent hours scanning, shrinking, and painstakingly pasting evidence to hexagon boxes.

“And this,” I said, “is a copy of the eulogy I gave, when I led my stepfather’s memorial service,” before rotating the box to show another side. “And the estate sale I held thereafter, where I sold around $5,000 worth of things.”

“How old were you?”


“Where was your mother?”

“She has an anxiety disorder,” I said, blankly.

She made a note. The man in the corner did not make any notes. It was then, however, that I pulled the remaining box from the stack⎯the smallest, and seemingly least important. I paused, placing the tiny box on the table, and mustered the courage to look her in the eye to say the one thing I had really come to say. I took a deep breath.

“But none of that is the reason I’m a future entrepreneur,” I began. “Not the awards. Not the recognition. Not the hardship. And nothing I’ve just gotten done telling you about.”

I slid the box toward her. She lifted the lid. Inside was a plush red something, tucked neatly inside.

“What makes me a future entrepreneur,” I said, “is that, right there.”

She pulled it out of the box.


It was then that Andy McKelvey, billionaire business mogul and founder of the empire, stood up, walked over to me and shook my hand. A week later, I accepted a $120,000 scholarship to Wilkes University, a private liberal arts university, a brand new Dell laptop, and my first chance at someday. It wasn’t until many years later that I discovered what I had said in that interview room at Penn State University wasn’t just a well-executed line to win a scholarship; it was the truth. Except if I could go back in time, there’s one thing I would change: I wouldn’t put a heart in the box. I’d put a handful of guts. (But maybe not actual guts.)

Because while your heart may kickstart an idea, it’s your guts that see it through. That see you through.

It was guts that got me through the four years that followed, and the phone call that said, “Come quick.” It was guts that got me through the note on the door that simply read, “Call me. Signed, The Coroner.” It was guts that got me through the aftermath of grief and feelings and fits of anger when I’d throw her favorite pair of hot pink reading glasses against the wall, pissed I never got a break from taking care of her, even after she died. I juggled writing a senior thesis project with sending death certificates to credit card companies; using fake IDs to get into bars while leaving messages for lawyers. She told me she wanted to die; she told me the pain was too much. She wished for a gun. As it seemed to my then 20 year old self, my mother was even lazy about dying.

Afterward, it was guts that propelled me through all of the big firsts on my own: First apartment in the city of brotherly love (couldn’t afford it), first car loan (definitely couldn’t afford it), first Grey Goose martini (pretended I could afford it), first bank account (proved I couldn't afford it), first “real” job ($32,000 seemed like a bazillion), and first resignation from my first “real” job. (When you catch your married boss making out ferociously with your co-worker, you freak out and call your other co-worker to pick you up, only to start the beginnings of World War III when you find out the other co-worker was also his mistress.)

Later, guts propelled me through another, unique set of firsts: My first business, first time I tanked a business, first job I took in advertising sales to compensate, first house I decided to build with an Asian man (bad idea⎯not the Asian part, the house part), first time I actually left a man (good idea), first time I let financial irresponsibility get the best of me, first time I found myself on the street with no where to go, first time I actually felt like trailer trash, first time alone in a parking lot with $26 dollars to my name, first time I sold my car & fled to the country of Chile with the hopes of leveraging a lower cost of living while getting a new business afloat, first year in Chile rebuilding my business from my laptop, first employee hired, first employee fired, first business partnership made, first article in Entrepreneur magazine, first time someone recognized me on the street, and, ultimately, first million dollars.


Through all the firsts, and all the fuck-ups, I was right about one thing: My someday would be different.

I’m humbled to say that after a bleak beginning, I've done alright. Looking back at my mother's tax returns, I went from $5,618 annual income in 1995, to making my first million in business before I turned 30. I went from growing up, living in a trailer using hair dryers to heat the pipes in the winter time, to running a business on my Macbook, traveling the world, drinking expensive wine, often earning $5,618 a day.

The success I’ve had to date was not groomed. It certainly wasn’t because I came from money, or because I had good fortune backing me. It wasn’t because I had a loving home with loving parents, nor because I was smarter than the average girl, or prettier, or more anything (though I am pretty clumsy in the kitchen so maybe that counts). Nothing I have is because of luck, or because someone gave me an opportunity. I made someday myself.

Have I screwed up? Been scared delirious? Been wrong? Been worried? Been uncertain? Every single day. But it doesn’t matter, because those feelings are still easier than the feeling of knowing you aren’t doing the best that you could. It’s still easier than living with a cheap, knock off version of yourself.

Because that gap between what you’re doing and what you could be doing will eat even the most ironclad heart…alive.

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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.

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