The 67 Emotions of Unconventional Success

OBLIVIOUS

When tears silently fell from her cheek upon finding the note from her lover, 3 days before their daughter was born that read: “I'm sorry. I can't do this.”

ASHAMED

When classmates asked where my daddy was. I lied & told them he was Crocodile Dundee, and had to be in Australia to tame the outback.

CONFUSED

When we used different money than everyone else to buy bread & milk.

BITTER

When I was 14 and sat in the hospital waiting room on a sunny June day. When my Uncle Jimmy finally emerged, after what seemed like hours, he handed me a pamphlet. It read, “Helping Your Family Cope with Terminal Cancer.”

NOSTALGIC

When I would hear Puff Daddy's “I'll Be Missing You” come on the radio after he died, just a few short months later, after tearfully asking me to call him “dad” instead of “Jimmy,” like I always had. I got to call him it twice.

MORTIFIED

When it was just me & my mother after that, and all of the other 15 year olds had basements underneath their houses. We had wheels.

FRUSTRATED

When my mother's debilitating anxiety & social disorder prevented her from ever coming to watch me play volleyball more than once in 4 years. We were nearly state champions.

RELIEVED

When the founder of Monster.com thought I was worthy enough to be awarded a 4-year, all-expense paid scholarship to a private, liberal arts school—room & board included. The scholarship was based on financial need & demonstrated entrepreneurial spirit. My mother cried.

GUILTY

When I took the scholarship and left her all alone.

SADDENED

When an unexpected card would arrive with $25 that she didn't have inside, telling me to go buy myself something pretty.

ANNOYED

When, a few years later, I found myself back in that same hospital waiting room. But this time, it was my mother I was waiting on to come out of the doctor's office.

SCARED

When I realized the seriousness of the matter.

PATIENT

When she taught me how to pay all of the bills, as I wrote out check after check from her hospital bedside, as nurses came in and out to take her blood.

LIVID

When the doctor's arrogant insensitivity to her pain one day made her weep.

VENGEFUL

When I let him have a piece of my 20-year-old mind.

FRUSTRATED

When college friends ragged on me for not going out that weekend to party.

RESENTFUL

When I couldn't.

SHOCKED

When I got the phone call while driving to my first day at my internship at a local TV station.

DEVASTATED

When, by the time I got to our trailer in Northeastern Pennsylvania, the coroner had taken her body.

BITTERSWEET

When, 4 months later, I walked across the graduation stage & got my college degree, not even bothering to look out into the crowd for a familiar face.

INDIFFERENT

When I hastily auctioned off all of our things.

LOST

When I sold our trailer for $13,000 at market price.

DISTRAUGHT

When I moved to Philadelphia and knew no one.

HOPEFUL

When I landed my first job in marketing.

WORRIED

When I didn't have anywhere to go that Christmas.

GRATEFUL

When I was so good at my job, I received a promotion to head up regional marketing efforts. And then another promotion. And then another.

DISHEARTENED

When I'd see planes pass by my office window, and longed to be the kind of person who didn't let life pass them by.

DISAPPOINTED

When I realized that sitting at that desk, serving to make big companies even more money, was my entire purpose in life. I didn't want to waste my life like my parents had, always waiting until tomorrow to be happy—because tomorrow, you're dead.

DISILLUSIONED

When I discovered that my dreams of becoming a corporate hot shot weren't my dreams anymore.

DESPAIRED

When friends told me to suck it up, and that work was simply that: Work. (It wasn't supposed to feel nice.)

LONELY

When I felt like no one understood me.

ARROGANT

When I quit my job & decided to start my first business, instead. I was going to do what I had been putting off for years: I was going to write.

FOOLISH

When I made some hasty financial decisions.

EXCITED

When that same year, I got a contract to write my first eBook.

SMART

When I developed my own site to sell the book there, too.

DETERMINED

When I laboriously tried to learn HTML.

ELATED

When I saw my very first sale come through.

INTRIGUED

When I discovered the world of Google Adwords.

ADDICTED

When I took my love of marketing and applied it in new ways.

CONFIDENT

When I painstakingly slaved over a book proposal to write a non-fiction narrative titled, “The Truth About Mangoes.” (Let's not talk about what a horrible title that was.)

TORN

When I repeatedly received the infamous rejection letter (after rejection letter after rejection letter after rejection letter).

DESPERATE

When the waterfall of poor and hasty financial decisions finally caught up to me.

HOPELESS

When I caved & took a job in advertising in order to pay the bills.

ENCOURAGED

When I got contract after contract signed on the spot.

UNCERTAIN

When, in my heart, I knew I needed more than signatures & commissions.

PETRIFIED

When, despite that knowledge, I was too scared to make any bold moves, knowing that I had no one in the world to back me up if I failed.

INCENSED

When I stood by and watched that fear get the best of me…for years.

OPTIMISTIC

When I enrolled in graduate school for my master's degree in Linguistics.

ANXIOUS

When I imagined that my degree would be The Answer™.

IRRITATED

When loan applications were denied without a co-signer.

STUBBORN

When I decided that I would tutor writing to make up for it.

HEARTBROKEN

When my best friend told me I needed to find a new place to live so her boyfriend could move in.

DEFEATED

When I had no choice but to go stay with a mysterious new guy I had been seeing.

DESTROYED

When, a few weeks later, was sobbing in the middle of the night in a Kmart parking lot.

HOPELESS

When I had nowhere to go.

ANGUISHED

When I looked in the mirror and saw the cranberry-colored fingerprints around my neck.

OBSTINATE

When I sat there in the middle of the night, determined not to be a victim.

DILIGENT

When I realized that I might not have had anything left, but the one thing I did have? Were my ideas.

COURAGEOUS

When I published an announcement to my baby email list to write a book I had not yet written.

VALIDATED

When I heard the first sale.

AMAZED

When reader after reader voted with their wallets.

EXHILARATED

When I realized that my writing could save my life—literally.

DEDICATED

When I continued to publish.

INSPIRED

When more and more readers came to say hello.

PEACEFUL

When my influence online grew.

INVIGORATED

When I discovered that you can make red, hot money from your art, using this thing called the Internet.

HAPPY

When, ten years later, I look around to find a whole different reality: One that I created by hand for myself. I’ve built a million dollar brand around giving the middle finger to societal expectations and finding unorthodox ways to live a happier life. I published the book, also called THE MIDDLE FINGER PROJECT, with the one-and-only Penguin Random House. (!!!) In addition to the United States, Canada, Australia and New Zealand, the book has also been published in places like Finland, Ukraine, Russia and the United Kingdom. (The Finnish cover is adorable!) The Audible version is hilarious. Seth Godin called my voice “a voice of originality in a world with too little of it,” and The Today Show was coming to my house before the 2020 pandemic upended EVERYTHING. (CBS, The BBC and Jenny McCarthy show, however, I was able to do over the phone. ?)

I've become known for my irreverent, voice-driven writing, have since ghostwritten other books with Penguin et al., and my independent publishing company, Irreverent Ambition, publishes the most fun-to-read newsletters & books in the world. I teach creative writing via my OTHER newsletter, Meat & Hair. I have a beautiful home in Costa Rica (read: fewer cockroaches than the neighbors), recently purchased a historic property in Philadelphia, and spend several months a year traveling around the world to places like Argentina and Italy; Ecuador & England—which sounds far more pretentious on the page than, perhaps, if we had this discussion while binge drinking wine. I work remotely from my Macbook, spend wide-open mornings writing words & sipping coffee, take leisurely two hour walks at sunset, and splash around in irritatingly clear turquoise water almost daily (which means I spend an inordinate amount of time sucking in my gut and trying not to look like a city slicker asshole). To add to the list of things-that-make-me-annoying, I have a wonderful partner with whom I share these travels and this incredible thing called life, we're building lots of things together, including a tourism brand called With Love From Costa Rica, as well as our own brand of coffee! I relish the finest glass of red wine I can find in the evenings with my feet dangling in a pool overlooking the Pacific Ocean (okay, fine, it’s the neighbor’s pool), and when I’m not cringing from the sun or stringing words together in meaningful ways, I’m probably on a podcast answering one question:

How did you go from sleeping in a Kmart parking lot with $26 dollars to your name, to creating a business and a life like this? (By which I’m fairly certain they mean the cockroaches.)

To which I respond:

For everyone out there thinking to yourself that it's unrealistic, YOU ARE WRONG.

For everyone out there shackled by fear, telling yourself that you could lose everything, YOU ARE RIGHT.

And for everyone out there that, despite that knowledge, is still willing to risk it by fighting for something more out of this fleeting speck of time we're granted here on earth, YOU ARE THE ONLY ONES WHO WILL TRULY SUCCEED.

Because at the very least, you know that you did everything you could.

Not everybody else can say the same.

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