Before we get into this week, I wanted to share an interview I did with one of my favorite lifestyle newsletters, Brent and Michael Are Going Places. If you’ve ever fantasized about leaving everything behind and living on the road, these two do an incredible job of sharing the realities of doing so. Plus, they’re a hoot.
I was in the hallway between classes, lockers lining either side when he said it. It was the movie moment when everyone else disappears, when it’s just the two of you in a blurry world, the audience leaning in with anticipation, hoping for the kiss. Except I didn’t want to kiss him. I wanted to drive my biology book straight into his larynx. I wanted to transform into a gargoyle and crush him between my stone paws. I wanted him to see the future, to see that he was wrong.
He had just beaten me for our high school’s Valedictorian on a technicality, and this man had the audacity to say, “you know, if you focused on your social life less, you could really be something.”
Be something?
Only a few years prior he’d beaten me at Power of the Pen, a writing tournament for nerds in Ohio. We were both voted Most Likely to Succeed our senior year. (I was also voted Most Likely to Have an Unconventional Night Job but that’s neither here nor there.) We’d been in competition, at least in my head, for years. Teachers loved him. Parents loved him. And I wanted to lacerate his vocal cords. One hallway confrontation, and what I believe he thought was sincere advice, has tickled at my heels for two decades.
You could really be something.
I bring it up because I’ve been thinking about success lately, about satiation, about what I want my future to look like. In the reader survey I sent out, a number of you asked me to share how I became a writer. All my life I’ve wanted to know everyone else’s play-by-play so I could see where I went wrong, to figure out where I could go right, to see which parts were hard work and which were just luck. Of course the irony is that there isn’t a playbook, and things change. I mean when I was in high school the worst thing you could be called was a sell-out, and we all know how that turned out. (Looking at you, every celebrity in a crypto commercial.)
Below is a break down of my more professional past, a play-by-play of how I ended up here — as a writer, as a professional, as a person working remotely in the mountains — and what stands out to me as meaningful and what doesn’t. I breeze by the familial, emotional, and intimate for the sake of brevity here, but you can assume they’re percolating in the background.
You’re all so gracious to let me share my stories, so here’s the origin of this storyteller. Let’s begin.
Student, UNC Chapel Hill
In college, a professor who I adored had a head-to-heart with me after my visible disappointment at getting a B- on an assignment. He asked what I wanted to be and I’m pretty sure I said rich. All I dreamt about was financial security. It was a trickledown dream from my parents, and it drove me toward the career I thought would make me the most money: an investment banker. In the 7th grade I’d made an entire presentation about becoming one. And that was the plan — until I met people who were actually going to become investment bankers.
In one of my marketing classes in the Business School, we’d been broken into small groups to present case studies, and then were asked to grade each other. I gave the first two groups As. They did fine. But the girl next to me saw my scores and said, “don’t give them As. They’re not going to give you an A.” She was right. Everyone was giving each other Cs out of sheer competition. That afternoon I changed my business major to a minor, and I switched to the advertising tract in the journalism school. I was competitive, but I wasn’t cutthroat.
But looking at the B- on my copywriting homework, I felt the shame swirl of that old high school hallway, like I’d somehow fallen behind without even knowing where I was going. My professor shook his head at me. The assignment was to come up with a new tagline for Angie's List.
“Do you care about Angie’s List?” he asked me.
“No.”
“Then why do you care that you wrote a shitty tagline for them?”
“I wanted to get an A.”
“Why?”
“Because if I get good grades then I’ll get a good job?”
“Get good friends. That’s how you get a good job.”
That professor would later tell us:
we were all failing at advertising if the only classes we took were about advertising,
that no one cool would ever give a shit about our grades,
and a delightful story about how his wife had bought their daughter a polar bear costume for Halloween, while he had bought a small stuffed animal seal, cut it open so the stuffing was coming out, and then, drove their daughter to school and put fake blood all over the seal and his daughter’s mouth without telling her mother only for the daughter to come home having been a runaway hit with the class but in trouble with the teacher.
He changed my attitude about life and thus changed the course of it.
I went to undergrad in North Carolina with 14,000 other students on a half-ride scholarship. I didn’t know anyone, so in my first month on campus, I tried out for an a cappella group. I got in, and many of those women remain in my life. In my senior year of college, our a cappella group went “on tour” in the British Virgin Islands. One girl knew some guys who owned a charter sailboat company down there, and another had a godfather who owned a strange little resort on one of the smaller islands. The serendipity turned to travel plans, and I had a phone call to make. Working at the Visitor’s Center (and for Fox Atomic, and for the Alumni magazine) paid for food. It did not pay for a ticket to the BVI.
“So, all the girls are going to the Caribbean for spring break, and I was hoping I could too? It’s um.. It’s a thousand dollars.”
My dad offered me a choice: he’d been saving a piece of gold for me. I could trade it in now and use it for the trip, or I could wait. Let it hold its investment.
I was 22, so what do we all think I did?
At dinner in the unrivaled salty breezes of the Caribbean, I sat next to my friend’s godfather, the owner of the strange little resort, and asked him about his life, how he’d built the resort, what he found the challenges to be, and who he might be looking to hire. Back at school, I sent him a thank you letter and several of our CDs. I was about to graduate with a BA in Journalism, a minor in business, and absolutely no idea what to do with either. Two months later, he hired me and I was off to the British Virgin Islands as an unbearably smug and wildly unprepared 22-year-old.
Special Projects Coordinator, British Virgin Islands
I was making $22,000, and I had a free room at the hotel. In terms of actual tasks, I did everything under the sun. I designed magazine ads for the hotel, I ordered new signage for the resort, and I panic-coordinated an 8-night gastronomic event with a bunch of Michelin-star and James Beard award-winning chefs, along with some incredibly wealthy vineyard owners from Germany. (Again with the Germans.) But my boss was not the boisterous and laughing man he had been at dinner. He was a man trying to build his own success, and he did not know how to be a boss. He was casually cruel in ways I needn’t write about, but instead I’ll tell you how I handled the cruelty. I ran to the top of the mountain every day and cried. I tried to quit, telling him that I was giving him 100%, and if my performance wasn’t sufficient, he needed to hire someone else. I wasn’t qualified. He asked me to stay, telling me he would be better, that it was hard to remember how young I was because of how mature I seemed. I was pale and narrow in the heat of the equator and the friends I’d made on the island were worried. I sent another resignation letter a couple months later — this time while he was in London. I was afraid of him. And the response validated my fear. He told me to leave the island immediately, or he would have me deported.
I didn’t leave. Instead, I called friends that I’d made who worked on Richard Branson’s island, Necker, and told them I was in trouble. That night, I left the resort. The Necker team had a staff house on Virgin Gorda in Leverick Bay, and there was a spare unfinished room in the lower level where I could hide until I figured out my next steps. The boys in the house were tennis instructors and windsurfing guides and that night they were my saviors. We drank beer and sang songs and I slept on a mattress with no sheets, happy as I’d ever been, branches rubbing against the sliding glass door that wouldn’t close.
First Mate, British Virgin Islands
With no job, no cellphone, no laptop, but no desire to leave, I started making bargains. The best was with the guys from the charter company. It was this: I’d join their ship as a stewardess and tour guide, making all the meals for the guests and showing them around the islands, and at the end of each trip, I’d give the guys all my tips in exchange for them teaching me how to sail. We agreed, and so we did. During the day, I played guide, and at night I sang at bars, returning to the sail bag to tuck myself in. At the end of a few weeks, I took a job on a 50-foot catamaran as the first mate. (I may or may not have been dating the captain, but again, neither here nor there.) I made a living tacking, jibing, and cleaning — until customs came calling.
It was (and probably still is) illegal in the BVI to violate your work visa, which is exactly what I was doing, and my former boss was serious about driving me out of the country. It did not help that the captain I was working for was also violating visa laws. We were, well… on the run. A pirate’s life, etc. But I had friends on the island, and when my name came up next, I had fair warning. We sailed to the USVI, I kissed that sailor goodbye, and I got a one-way ticket to Washington, D.C.
Program Coordinator, National Institute of Allergy and Infectious Disease
I bought that ticket to DC in the spring of 2009. It was not the best time to be looking for a job. I was crashing on my friends’ couch, one of whom was the same goddaughter of the troubled boss in the BVI. This time, it wasn’t her godfather who helped me, but her parents. After a month of unanswered applications, they put me in touch with a woman at the National Institutes of Health about a position recruiting postdocs and postdocs from underrepresented communities. I got the job and was the youngest person in the office by 20 years. They needed someone who knew how to use Facebook.
I worked at NIAID, and every day I would take the Red Line to the NIH campus with about 18,000 other people. The campus is surrounded by a massive fence, known to staffers not as a means of keeping people out, but keeping us in if something broke out. The NIH, and the government in general, is a place of rules. I am not great with rules, and so a job where you could not even check your email on the premises struck me as a little restrictive. So did the 30 minute lunch breaks where it took 20 minutes just to walk from my office to the cafeteria and back. I was applying for other jobs — jobs in the sparkly world of advertising.
During this time, I was also going to doctors for the lump in my neck. It had been a year of visits with various demeaning diagnoses: it’s part of your bone, you’re imagining it, it’s just an ear infection, maybe you need Zoloft? I finally asked those same helpful parents if they could refer me to a doctor, a good one, and the doctor they sent me to immediately diagnosed my lump as a tumor. Four months later, the surgery was finally scheduled. My boss got mad at me when I struggled to make it to work after having my neck cut open and my ear peeled back like a candy wrapper. The bill for that surgery, after insurance, was over $20,000.
When I did make it back to the office with my blood-drip bag attached to my shirt, I started writing. A very real benefit to having a mind-numbingly boring job and also only having access to the Microsoft Suite is that you can do a lot of writing. In 2010, I started an anonymous Tumblr blog called Date By Numbers. I was complaining to my mom that no one ever hit on me, and she laughed at me saying, “plenty of people hit on you. You just don’t like any of them.” So I started numbering the guys that hit on me to prove her wrong. (I was only sort of wrong. Lots of guys hit on me. Most of them just stopped hitting on me as soon as they got to know me. Which, fair. I was moving through what can only be described as a real assload of trauma.)
I always had blogs. Xanga, LiveJournal, Blogspot, etc., and I had started and stopped many a Tumblr before finally finding a thread that resonated. Date By Numbers was featured on Tumblr’s Top Ten, and it took off. And then,
Project Manager, BBDO New York
I got a bite on an application I’d submitted cold to an ad agency in New York, an application on which I had put my best friend’s address — in New York. I called in sick to work and took the Bolt Bus to New York City, baby. I interviewed with the Executive Creative Director of GE, a sound and thoughtful man, and I also interviewed with the ECD of Gillette, an absolute lunatic. Guess which one hired me. I was one of two Americans on his team. He was always speaking German to his favorite art director and copywriter, the three of them screaming at each other day in and day out. It is incredibly difficult to manage a project when you cannot tell what anyone is saying, so amidst one of their screaming matches, I stood up, brow furrowed and high heels growing by the minute, to yell the German I’d been rehearsing, “Es tut mir leid, ich verstehe nicht. Ich kann helfen, wenn Sie Englisch sprechen.”
They stopped and stared at me, and then they applauded. I was coming into my power, at least at work. Outside of work I had some $40,000 in student loans, $20,000 in medical debt, $1250 per month for rent, complex PTSD, panic disorder, and a secret identity.
And that secret identity was starting to grow. I was writing anonymously for multiple places about dating, even appearing a couple times as a shadowy figure on shows doling out dating advice. My writing was doing well, but my mental health was not. I tried to get a prescription to Xanax to manage my panic attacks, but the doctor I went to told me to “pull up my big girl pants and grow up.” I tried to date people, but I wouldn’t let anyone get close. I tried to take care of myself, but found the city made it almost impossible. I needed to get out.
Senior Project Manager, CP+B Boulder
I was a very good project manager. I still am. Not because I’m good with software, but because I’m good with workplace dynamics and people. I wasn’t relying on Asana or Gantt Charts, but on my ability to know that Arielle is always lying about when she’ll be done with something and that Jim always stays out too late on Thursdays. But however good I was at people, I was very, very bad at being a New Yorker. I could see that my mental state was collapsing, and I knew I needed a bigger sky. I saw a role posted online at a reputable agency in Boulder, Colorado, and I applied. And guess who was a creative director there? My ole copywriting professor, Mr. Get Good Friends. After a somewhat intense interview process, he put in a good word for me, and I put in my resignation in New York. At my going away party in the city, I asked that wild, German-yelling ECD who I’d come to love why he’d hired me. “I don’t know, you had chutzpah.”
The job in Boulder paid $55,000 and was about 8 miles outside the downtown. Because I’d spent the years prior trying to live in Big Cities and pay off debts, I was (naturally) broke. I bought a bike to commute with and started riding to work. And riding to the store. And riding to bars. And riding to the park. And riding and riding and riding until I somehow became a cyclist.
Cycling was my first true reprieve from anxiety. Once I was out there, heart pounding from effort rather than fear, something started to shift. I was still anonymous on my blog, but now I was writing about empowerment, mental health, prioritizing yourself. I was excelling at work, making friends, and learning to listen to my body. I was also dating, and this time, more successfully.
One night, I found myself on a date with a man who specialized in the repair of fine, classical instruments. He told me he made very little money, but it was his calling. He told me he thought it was important to be upfront about his salary, because “some girls aren’t looking for that.” He was handsome, pleasant, and by his own description, poor. I excused myself to the restroom. Looking myself in the mirror I said, “maybe you’ll just make all the money. Maybe you just do it yourself.”
Maybe you’ll just make all the money. Maybe you just do it yourself.
I put my head down with the blog. I knew that project management wasn’t going to be my golden ticket, and I couldn’t let a pseudonym keep taking all the credit. I came clean, I kept writing, and one morning I opened my laptop to over 4000 notifications on Tumblr. My favorite author, Neil Gaiman, had reblogged something I’d written and called me a brilliant aspiring novelist.
Up until that point, many people made fun of the blog, mocked it, questioned my judgment, I even received hate mail and death threats for … being a woman with an opinion? For writing about dating? It’s unclear to me still what people thought I should have been doing or who I should have been. That morning I knew who I was: an aspiring novelist. I had been writing the blog for three years, but it was that morning I let myself become a writer.
Maybe two months later, Gaiman was on a book tour coming through Denver. He reserved me a VIP seat, and I got to meet him beforehand. I needed to know:
“How did you come across my blog?” I asked him.
“I don’t know. And isn’t that one of the great things in life? Sometimes things happen, and we just never know why.” (Paraphrased, but you get the idea.)
Boulder was a good time in my life. It was my introduction to Colorado, to cycling, and to self-advocacy at work. Many people liken working at ad agencies like Crispin to summer camp, but many more liken it to having Stockholm Syndrome. You never leave the office. You work all hours of the night. You huddle in corners and cry together about the stress. And you all end up dating each other because anyone normal would be like, “it sounds horrible to work there.” And it was. The opportunities to stand up for yourself were endless, lest you get walked all over by men who introduced themselves by the nicknames they came up with and ranked which women they’d sleep with. But like many of my peers, I still ended up dating a coworker. I was riding my bike every day. I was living in my own apartment with my cat Alistaire. Things were stable.
My boss offered me a transfer to the LA office, and I couldn’t have said no faster.
A month or so later, the fantasy fractured. In one week, the boy I was in love with left me for an ex-girlfriend in New York, my grandmother died, and my cat was eaten by a mountain lion. While in Idaho for the memorial, I got an email from my boss.
“Wanna move to LA now?”
I flew back to Denver and packed my bags. I was a 28-year-old, single, cat-less cat lady who hated her job. But Neil Gaiman knew who I was, and that was a start. It was time to start living for me.
To be continued next week…
This was already some 3,300 words. Go enjoy your Sunday, and we’ll get to my 30s next week. And if you’re inclined to share, I’d love to hear what the pivotal “fuck it” moment in your life was.
At 59 years and 4 months I am one month older than my mother got to be, and I am churning around in my fuck it moment. I retired four years ago from an incredible job as an air traffic controller in the D.C. area and have been “living the life” in a beautiful Active Adult communities in the Shenandoah Valley. No doubt I am fortunate to be able to retire young and have a good pension. I have good friends, as well as plenty of free time to read and write and cook - the things I wanted to do more of.
And yet.
I feel like I have been following a predetermined path. Marriage, kids, job, retirement, grandchildren (soon!) and then, what? Death? Even with my great job, which I loved, I was following in my father’s footsteps. Come to think of it, retiring young is also following in his footsteps. His world, after my mother died so young, just got smaller and smaller as he waited to join her. It took twenty-two years and at the end he never left his recliner.
Fuck it. I am not doing that. Despite the fact that many people would love my life I am breaking free and going back to work. Next week I have an interview to be a 911 operator. I need to keep expanding my world, and while I have tried new things these past four years, none of those things matter to me. Being the voice that brings calm to someone in distress - that has always mattered to me. My children, my students, and my friends will attest to my ability in that.
So fuck the good life. I am heading back into the trenches.
I confess when I saw the length of this and that it included a rundown of your career, I thought, "Hmm, I might not be so keen on this.
But I was wrong. Neil Gaiman nailed it when he mentioned you.