Becoming a writer, part II - #55

The "know your worth" era.

This is an origin story. If you missed last week’s edition, start there.

I drove from Boulder to LA with an empty cat carrier and an empty heart, sob-yelling along to every Fiona Apple and Alanis Morissette song available to me. I cried in Grand Junction when I stayed at a distant cousin’s house full of antique dolls. I cried when I paid the $35 just to walk around the Bryce Canyon parking lot. I cried when I couldn’t figure out how to turn on the U-Haul’s lights in the Zion tunnel so I just tailgated my way out. I cried when I pushed my suitcase in front of the door in the shitty motel in Vegas. And I continued to cry as I first encountered LA traffic, taking my things not to a new home, but to a storage unit. 

It was a rough three days. 

Senior Project Manager, CP+B Los Angeles 

This was not the heyday of CP+B, an agency famed for things like $100 Fridays where they just… gave everyone a hundred dollar bill. This was the tail end of their success, with more failed pitches than anyone was willing to acknowledge. And because the pitches kept failing, we had to keep pitching, and pitching at an ad agency is like unabated binge-drinking except you never get drunk, you just stay hungover. Everyone around me seemed, to some degree, miserable. Failed relationships, comparison traps, thwarted careers, tabled art projects — every day someone was crying and every day someone else was like, “maybe we should get drunk.” 

When I initially accepted the offer to move to LA, they tried to move me with the same salary. This is when I started to move into the Know Your Worth era of my career. The cost of living in LA at the time was around ~30% higher than that of Boulder. They’d already played their hand, saying they needed me in the LA office, and need comes at a cost. I said I wouldn’t go without more money, so they gave me a cost-of-living raise and I set to work. 

Meanwhile, two extraordinary things happened:

1. I got a book deal. I cannot stress enough what a silly little book deal this was. It was through Thought Catalog, LLC, and for those of you who don’t know what that is, good. But I emailed Gaiman and asked for his advice. In a nutshell, he said your first deal is almost always bad. Just take it, and claim the position of author, and move on to the next book. That book was essentially all the best essays from Date By Numbers with a few others. You can get it here. And if you have read it, and liked it, leave a review. Reviews (good ones) are one of the kindest things you can do for any writer — even if said writer is mildly embarrassed by what they wrote a decade ago.

2. I applied for and was accepted into the Rapha Women’s Ambassador Program. Rapha is a cycling apparel brand, and it was my first foray into actual community building. There were about 20 women from all over the states who were brought together to help get more women into cycling and to foster those communities locally by hosting weekly rides, skills clinics, and other events. This opportunity really gave me an identity, and it also gave me a writing niche.

Two of my great loves: Cooper and bikes.

But there was one problem: the guy I was seeing. 

I’m including him to illustrate the power of how one singular passenger on this train of life can throw such a hissy fit that it derails the entire train. My new LA boss had set me up with him. Several of my coworkers were friends with him. Everyone loved him. So fun at parties, etc. But over the course of our relationship, he called me a slut for writing the book, he said he “didn’t care” when I told him about the assault because I’d already “told the internet,” he said cycling was a dumb sport and that no, I couldn’t bring my bike inside, he routinely accused me of cheating, and then when a family member suffered a psychotic break, he said, “my ex had a psychotic break and that was worse for me than this is for you” and then left to smoke a joint  — he was a Bad Boyfriend. But again, everyone loved him, and up until that point, I hadn’t had a successful relationship, so I was having a very serious case of “it must be me” mixed with symptoms of blanket failure.

We broke up, I got Finn, we got back together, I got deeper into cycling, we broke up, I tried to transition the blog into something else, we sort of got back together, and then, I went on a writing retreat in Guatemala hosted by the inimitable Ann Friedman and the inspirational Gracy Obuchowicz. 

At this point, my life was pretty much run by panic disorder. But I was the most terrified of flying — not because I don’t understand how planes work, but because I was sure I was going to have some kind of medical emergency in the sky, no one would be able to save me, and I would die before we landed. It was all my anxieties in one: there’s no one you can rely on, you’re trapped, your health is failing. I had to take a lot of medication just to get to Guatemala, and I blacked out the entirety of the 5.5 hour flight, the 4.5 hour bus ride, and the 1 hour boat ride to the retreat. It turns out that having a high-stress, all-encompassing job where everyone drank all the time was a great way to ignore what was happening in my head. But this trip could have basically been titled, “let’s see what’s happening in your head for 12 hours a day, 5 days in a row.” Every day started with meditation and introspection, and it ended the same. This was my first experience with meditation, and I wanted more.

We all asked Gracy, “is there a meditation you recommend doing at home?”

“I use this new app called Headspace. You should try it.” 

On the 11-hour journey home, I listened to the same Headspace meditation on repeat. I didn’t take medication on the flight. I trembled and cried, but I did not boil over. When we landed, I was exhausted, but renewed. That retreat reminded me what writing felt like, and to be surrounded by those women! So many women who shared a resounding, “wow, he sounds like trash. And so does your job. But your fiction is great.” 

It was December of 2014, and I was ready to be myself again.

1. First, I dumped the boyfriend. As you can imagine, he took it poorly, emailing me a YouTube video of CeeLo Green’s “Fuck You”. 

2. Second, I asked for a raise. And got it. 

3. Third, I started dating a celebrity, lol. 

4. Fourth, I brushed up my resume. 

And then, I got headhunted. By Headspace. 

Head of Projects and Production, Headspace, Los Angeles

Some important context on getting this job: the ex actually worked for a very small recruiting company that represented Headspace at the time. And when I say small, I mean there were like five employees in one room. So when I got the headhunting email from a woman the ex had mentioned multiple times, it gave me pause. Was this a joke? Did she not know who I was? Should I tell him before I talk to her? 

I started conversations with her, unsure of what to do, when she told me Headspace had been trying to hire for this role for six months. Six months? Six months he’d known about the perfect job for me and never considered me? Six months of me trying to leave advertising, dating a recruiter, and him not once mentioning this role? Six months? AND HE’D NEVER MENTIONED HIS GIRLFRIEND OF A YEAR TO HIS FIVE COWORKERS? Hell hath no fury, etc.  

So I interviewed, I got the job, and before I could email him to tell him, he found out. I got a lot of angry emails, every one of them worth it. I was leaving advertising for a mental wellness company. 

Meanwhile, the celebrity not-all-the-way-boyfriend I’d picked up shared an interesting sentiment with me. We were talking about the concept of marriage, and he said, “the thing most people don’t understand about marriage is that only 50% of it is someone’s personality. The other 50% is what time they wake up in the morning, what they eat for breakfast, how they spend their weekends.” And I sat there looking at him, 11am, vegan smoothie, comedy clubs, looking at me, 6am, bacon and eggs, camping. What was I doing?

I took a step back — from my entire life — and reassessed. What did I want to be doing with my days? Who did I want to be spending them with? And how would I get to whatever that vision was? 

I broke up with him, I got a therapist, I put my all into the new job, and I went on a date with a bike racer who I knew for a fact liked bacon, eggs, and camping. But most important to this angle of the story, I started dedicating time each week to writing.

I wrote guidebooks for Rapha, I wrote articles for Bicycling Magazine and Runner’s World, even scoring the cover of Bicycling Magazine for their “fun” issue. I was starting to be known as an actual writer, but I was also starting to be a “career woman.” 

Shouldn’t have fixed that gap tooth.

Managing Editor, then Director of Movement and Sport, and finally Director of Core Product

A few months into my time at Headspace, they hired an Editorial Director. She hated it. And when she was leaving, she helped me craft my pitch to take her spot. Headspace was nimble then, maybe only 25 employees, and almost no one had heard of it. Most people thought I was insane for taking a job at a “meditation company” but I knew I needed to diversify my career past advertising, or I would be stuck as a project manager forever. (That it never occurred to me to just… be a writer? speaks to how much I was still craving financial stability more than anything else.) 

I pitched myself as Editorial Director, and they gave me Managing Editor. My team and I built out their blog, the Orange Dot, as well as a podcast, their newsletter, their walking series, all content for their Nike partnership, and more. I was promoted to Director of Movement and Sport, building out the new vertical, and then eventually to Director of Core Product. And the harder I worked, the more of my writing was funneled directly into work.

I got four raises while I was there and probably asked for eight. The former CEO told me it was charming how often I asked for a raise. But every time I had a review, I asked what deliverables I would need to hit to get a raise, and every time I hit them. I may have been charming, but I was also relentless. I wanted to be CMO by the time I was 35. 

Until I didn’t. In 2018, I was suffering from chronic nausea. Test after test said the same thing: nothing. Doctor after doctor said the same thing: stress. Driving myself into the ground at Headspace with constant turnover of bosses and unhappy employees left me feeling ill all the time. It wasn’t the right environment for me. It was no longer a mental health company — it was a tech company.

So in July 2019, after 4.5 years, I put in my notice with nothing lined up. Writing burned a weak wick in the background. At the tail end of 2019 and into 2020, I tried to start a newsletter that failed. Echoverse bought two of my story ideas to be turned into audio dramas and I’ve never failed at something so spectacularly in my entire life. I pitched a beloved and famous editor a story idea and the pitch was so bad she wrote back to tell me it was tone deaf. And just for good measure, the cycling ambassador program decided it was time to bring in some fresh (replacement) blood. I retreated into myself to figure out what the hell was going on, and as bad luck would have it, so did everyone else. 

VP of Content, UnitedHealth Group Ventures

It was February 2020, and a quick glance around indicated it might be a great time to get some health insurance again. I took on a role running content for a mental health app in the UHG portfolio. This was a Great Job. I loved my team and I loved the work. The app’s focus was not growth, but assessment scores — success to them was knowing the app actually made their members happier and healthier. They let me spin up projects left and right, and those projects worked. We were really helping people. But yet again, almost everything I was writing was for work. 

It is astoundingly easy to believe you’re not a real writer. I struggle to tell people I’m a writer now because they ask, “what do you write?” and I say “a newsletter” and I feel like I’m the 15-year-old protagonist in a coming-of-age story about a girl who takes her school newspaper more seriously than her friends. But what are the parameters of being a “real” writer? Getting paid for it? I was. Having people read it? They were. To see your writing make an impact? It did. Still, outside of my job, I published next to nothing during this time, and what I wrote, I hated. 

A conversation with my therapist helped change that. Every week, there were at least five minutes spent on the questions “did you write something for you” and “why not.” Five years of this conversation (and many, many others) and she finally made it plain to me: “you have a lot of darkness, and if you don’t put it on paper, it will eat you.” I went home and started writing the novel I am working on now. 

In 2021, I “graduated” therapy, we moved to Colorado, and there it was: inspiration, twiddling its thumbs just waiting for me to show up, like I’d been standing outside the restaurant in the rain while they’d been waiting inside at the table the whole time, just buttering their bread and trying different wines. I would’ve been mad if inspiration wasn’t such a flirt. I lived in this remote valley just shy of a month before launching this newsletter. And it’s the most fulfilling writing project I’ve had to date. Every week I look forward to it and want to pull my hair out — writing!

I kept working remotely and it’s likely I would have stayed at that Great Job for a while, but they were acquired by a company with a really different value system. I didn’t fit in, and at that point, I knew the cost of staying somewhere that felt off. 

Where I am now

You all know the rest. I’ve changed jobs twice since then, with Modern Fertility not working out, and now moving on to what really feels like the role of a lifetime, both in the work and the flexibility. 

Having a job is important to me. I like having health insurance. I like knowing I can pay my mortgage. I like being able to afford writing retreats. But being a CMO? I mean god, who cares. Certainly not anyone here, like somehow desk jobs get lamer and lamer the higher in altitude you get. Oh, you’re not a mountain guide? You’re not a backcountry ski instructor? You’ve never backpacked through the Yukon? Then who cares. But when you’re a writer, oh can you help me with my website? Can you help me with my social media? Could you write a story about us for the newspaper? Why yes, yes I can. 

I am a writer now, one with a lot more grace for herself. I’m a writer because I love writing. I’m a writer because I make time for it. I’m a writer because sometimes the things I write resonate with people. I’m a writer because sometimes the things I write resonate with me and only me. I’m a writer. Not a famous one, not a rich one, not even a reliably good one, but I’m still a writer. There’s just shy of 3000 of us here. My goal for the year was 5000. Unless something wild happens, I won’t hit it. But if a goal is there to provide structure for attaining something, what was I trying to attain? I suspect, with all the corn and cheese I can muster, that I already have it. 

(Though there is that novel to finish, and that show to pitch, and the space novella I keep writing dialogue for… but isn’t that the joy of it? The agony of it? Isn’t that, well, it?)

Of course, it’d be a delight to tie this story up with a bow — what a world to be like, “and that’s how I got on the New York Times best-seller list and sold a show to Netflix in the same week,” but that isn’t this story. The point of this story is to illustrate that life is long and strange and the best thing you can do for yourself is what you want to do for yourself. Not what sounds good, not what looks good, but what feels good. Even if it’s one evening a week, even if it’s just the beginning.

When I interviewed new candidates to work at Headspace, I’d always ask them one question: if this company didn’t exist, where you would you want to interview? There were two types of answers.

1. Some candidates would say something like: another mental health app, or go back to school for clinical psychology, or interview anywhere that championed the health of their members above all else.

2. But other candidates’ answers read like a Silicon Valley Yellow Pages: Airbnb, Spotify, Google, Apple.

I never hired people from the second group because they were less likely to be fulfilled by the work when it got hard, and they were significantly more likely to leave for something they considered better for their CV.

Now, I ask myself a similar question, but a little broader. If none of this (gestures broadly around) existed, and I suddenly found myself free with no obligations and no ties, what would I want to make sure was at least a part of my life?

For me, the answer is writing. That’s how I became a writer.