The Actual Worst-Case Scenario

How scary is it?

We crate-trained our dog, Dilly Pickle Chip, during the height of the pandemic, at a time when no one was going anywhere and we were Zooming our neighbors to play virtual cribbage. So, when Dilly had to practice spending time in a crate, we would just pretend to leave the house and go sit outside.

Despite the fact that he thought he had no audience, he’d immediately launch into a dramatic monologue professing his ill feelings for the crate. This sounded a lot like a zoo full of very angry monkeys who just wanted someone to bring them a goddamn banana already. And it earned Crate Dilly the nickname, “Dilly Pickle Chimp.”

Whenever he had to get in his crate, we’d sit in the front yard, cringing at his tortured primate howls, hating how much he hated to be trapped inside.

Not a big fan of doors, crates, or any barrier between him and the world.

When my employer called us back to the office several months later, we had long abandoned crate training. But as I returned to a windowless cubicle, I felt Dilly Pickle Chimp come back to life inside of me.

Every weekday morning, my stomach would morph into a pit of dread. I’d commute to work like someone was escorting me to the gallows. Then I would sit in my cubicle, encaged by grey walls, beige carpet, and artificial light, feeling tortured primate howls wailing inside of me.

A cubicle is not my happy place.

I function more like a fern than a corporate girl. I need regular feedings of dirt and sunlight and nourishing Oregon rain. I prefer to be surrounded by evergreens and earth, not laminate walls and weekly check-ins. I don’t want my movements dictated by an Outlook calendar, I want to curl toward the sun and take the next bend in the trail.

I’m also susceptible to depression during the darker months. So, my mental state suffers when I’m locked away from daylight. Even through the rainiest months in the Pacific Northwest, being under a pouring grey sky is way better than seeing no sky at all.

I’d fantasized about leaving traditional work for the freelance life for years. And that dream only escalated after I got a taste of working-from-home, when I could bring my laptop outside and run to a trailhead during lunch and hang out with Dilly all day. (And sweatpants >>> business casual forever.)

But, freelance writing always felt like something that was only available to other people and not to me. It was too big and too scary of a leap.

So, I kept going back to my cubicle every day, silently screaming about how much I hated being trapped inside.

When I close my eyes and picture a happy place, this is not what I see.

I always joked that when I got into Hardrock, a notoriously challenging mountain 100-miler, I’d quit my job so I could go live and train in the San Juans for at least a month before the run.

When I finally got a spot through the lottery in December 2021, I questioned whether that was actually a joke.

I’d been trying to get into Hardrock for seven years. During that time, I’d traveled to the San Juans to check out the course and had seen just how wild (and mind-blowingly amazing) the terrain was. And I’d learned that many Hardrockers go to Colorado weeks early to revel in the mountains, acclimatize to the altitude, and connect with the incredible community around the run.

I knew I wanted to maximize my experience when I finally got in myself - and be ready to run a rugged 100-miles at an average elevation above 11,000 feet – but there was no way my current employment situation was compatible with my hopes for Hardrock.

After lockdown restrictions eased, every employer had a choice about whether to embrace some of the flexibility they’d adopted during the pandemic – or to tighten the reins. My employer swung tight. We were expected to be more tethered to our cubicles than ever before. One day, I dropped my car keys on my walk into the office and when I realized they were missing, I had to let my supervisor know that I was going to look for them. I felt like I was a child reporting to my babysitter, not a 36-year-old woman who could be trusted to work and act like an adult.

If I couldn’t even go look for a car key for 15 minutes, there was no way I was going to have the freedom to work from Colorado for a month.

I thought again about my freelance writing fantasy.

But, it still felt unattainable. A Hardrock bib didn’t make it any less big or scary to quit my job.

As I started to train, every run was spent trying to crack the riddle of “how to Hardrock right.”

After waiting seven years to get in, I didn’t want to compromise on my vision for Hardrock. I didn’t want to spend June and July looking at cubicle walls, instead of endless meadows of columbine and paintbrush. I didn’t want to fail to finish the run because I hadn’t covered enough miles on the course and couldn’t build enough red blood cells while answering emails at sea-level.

On one of my runs, my brain found its way to the question I needed:

What’s the actual worst-case scenario, Emily?

I was so scared about the idea of quitting my job for freelance writing. But that fear sat in my head as an amorphous fear-scented idea. I wasn’t scared because I was thinking, “If I quit my job, then x, y, and z bad things could happen.” I hadn’t defined any of those variables. I was just scared.

When I interrogated my fears and actually named the possible negative outcomes, I realized they weren’t nearly as terrifying as the vague horrors I’d blown up in my head.

I could fail, yes. Feel stressed, anxious, full of doubts, face rejections, struggle to make enough money, flail with the logistics of running an independent business.

But, I realized the actual worst-case scenario was that I’d have to get another cubicle job.

At that point in my career, I’d cleaned construction sites, rolled bagels, managed political campaigns, been the press secretary for a member of Congress, run social marketing for a craft brewery, and become a jill-of-all-trades in communications work. I trusted I could find another job if I needed to. Which meant that I’d be no worse off than I already was.

It was so freeing to realize the actual worst-case scenario was that things would stay the same. (I do want to recognize there was some privilege playing into this mental exercise. I knew there were people in my life who would help me before I lost housing or food security.)

I decided to give myself six months to try and make it work.

That was three years ago this week. I’m happy to report I haven’t set foot in a cubicle since I packed up my desk in April 2022. And have found the free-range freelance life to be an infinitely better and happier way for me to exist.

I don’t want to pretend that deciding to quit my job suddenly made it easy or free-of-stress. It was not a jump-and-the-net-will-catch-you kind of thing. More like a bust-your-butt-to-make-it-work-because-it’s-worth-it kind of thing.

That first summer in the San Juans included plenty of anxiety about my professional and financial future. I rationed my shower money. Accepted freelance assignments from the summit of Handies Peak. Ate *a lot* of boxed mac & cheese. Slept in a 2011 minivan for six weeks. And sent a million emails looking for work – but I was sending them from 9,318 feet with dirt caked on my ankles and legs full of alpine trails, without a cubicle wall in sight. My first Hardrock was everything I wanted and more because I gave myself a chance.

Home sweet minivan home office.

I’ve turned to the same question again and again over the last three years whenever I feel scared to do something.

What’s the actual worst-case scenario?

Maybe my fears are valid and worth listening to.

But maybe, I’ve inflated another fear-scented idea in my head. And when I recognize that it’s not actually that scary, I can bust free of the walls that are holding me back - and explore the possibility on the other side.