When You Find Your Unicorn Job but Can’t Get Past the Gatekeepers

It was time to panic.

After nearly a year of effort, I had nothing to show for it. My dream job—the unicorn I was chasing—had slipped out of my grasp once more.

Exhausted, I persevered, hoping that somewhere there was one more unicorn to be found. Surely if I kept going I’d impress the right gatekeeper eventually…

What follows is a tale of my job-hunting woes and how I got around the gatekeepers that kept refusing to hire me. Multipotentialites often end up creating our own custom careers, but what happens when you get too attached to one particular iteration of the dream? And what’s possible when we think outside the box and open ourselves up to different paths?

Discovering the mythical perfect job

A couple of months earlier, I had returned from retreat with an idea: I should get a job. With hindsight, this was the obvious solution to “not having enough money.” But at the time the idea was revelatory.

It had been a few years since I’d begun building a portfolio career. I’d published a book, given a TED talk, and started delivering comedy presentations about my experiences with anxiety.

But I’d become frustrated with the freelancing I still needed to pay the bills. I enjoyed the actual work… but I struggled with the constant search for good clients with achievable projects.

My first epiphany was that I didn’t have to give up the portfolio career. I’d unconsciously been viewing “get a job” in black-and-white terms, as if it meant admitting failure and giving up on all my dreams.

Somehow I’d forgotten that a job could be part of a portfolio career, rather than replacing it. Suddenly, I could visualize the perfect outcome, the unicorn I sought. A single flexible job, which could provide:

• A steady stream of income
• Fun coding projects to balance my non-coding creative work
• Actual colleagues, which might save my solo-working sanity
• Freedom from constantly seeking new freelance projects
• Time to continue giving talks about mental health & writing books & whatever else…

Now I knew what my unicorn looked like, I simply had to convince whomever was guarding it to let me ride it.

Ghosts & gatekeepers

Unfortunately, the perfect job doesn’t appear if you simply google for it.

For months, no opportunity had everything. Sometimes I didn’t have the right skills. Other times, the job was in the wrong place. Sometimes, the employer even seemed actively hostile.

As I was about to give up, I came across an interesting, innovative company who seemed keen. We threw around exciting ideas for projects I would work on.

But the start date kept getting pushed back, and—slowly—the conversation just… died.

I’d found my unicorn, and it had ghosted me. I’d expected to have to impress some metaphorical gatekeeper to the unicorn zoo, but they hadn’t even turned me down… they’d just looked the other way and whistled until I left.

Still, the brief flirtation with the security of a part-time job had got me hooked. Before too long, I stumbled across another job posting which seemed almost too good to be true.

They wanted a software developer with my approximate skillset to work remotely from any part of the planet. The pay was good. Best of all, they treated their employees with extreme respect—trusting them to take as much vacation as they liked, and even to work whenever was convenient, provided they got the job done.

I could continue speaking about mental health, write more books, pursue other passions, all while enjoying the security of a fascinating, enjoyable, permanent job. I liked the sound of that.

Unfortunately, so did six hundred and fifty others. This particular gatekeeper might never even notice me.

I spent the entire summer determinedly preparing the perfect application letter, before leaping through a series of video interviews and coding challenges. Every day, I dreamed of placing this final piece of the puzzle into the life I wanted to have. The unicorn was in sight.

They liked my letter. 300 people left. Another interview with another gatekeeper.

100 people left. A coding challenge. I passed this gate comfortably.

Down to the final 20. The last coding challenge.

And then, finally, after a summer of effort… I didn’t get the job.

Reaching the last handful from six hundred and fifty applicants was objectively an amazing achievement, but I felt worse than if I’d been rejected right away. An entire summer had been spent, and >still the final gatekeeper had turned me away.

If at first you don’t succeed… insanity is trying the same thing again…

It was time to panic.

After nearly a year of effort, I had nothing to show for it. Less than nothing, really. I could have spent all this energy on literally anything else.

Even the thought of continuing to search was dispiriting. Did I want to put more time and energy into a seemingly-fruitless search?

Until, one day, the idea evolved. I wondered… what if my problems could solve each other?

My humorous-helpful talks about mental health were going extremely well, but this had led to a new difficulty. I kept being invited by schools and charities who couldn’t afford to pay.

These talks were hard to turn down. I wanted to help, but each talk was a huge time commitment. I could afford to do them cheaply, but I would struggle to do it for free.

Somehow, these two separate problems crashed together in my mind. Need a job. Can’t do free gigs.

I wondered: what if my job WAS doing these gigs? Could I somehow get paid to offer mental health support to places which can’t afford it?

My soul felt soothed at the mere thought, which is often a sign of a good idea. This felt right in precisely the way all those non-unicorn jobs felt wrong.

Then I asked the obvious question: how could I achieve this? The idea grew an additional tiny shoot. Over the years, people had often suggested I crowdfund, but I’d always waved the idea away. I had no clue what could justify strangers giving me money. But if those people were willing to spare a dollar or two a month to support my mental health work, this could actually work.

Best of all, no gatekeeper could stop me trying… except myself.

Afraid of success

It turns out I’m a pretty good gatekeeper, as it took a month or two to convince myself to actually do it. But the day finally came when I launched my crowdfunder on Patreon.

I’ve pushed a lot of scary buttons in the past: submitting manuscripts, suggesting dates, opening up a new tab on TV Tropes. But pushing the button to explicitly ask people for support felt like a new level of vulnerability.

All that worrying was for nothing. A couple of dozen people leapt in to support me.

On some level, I recognize that’s a relatively small success. But on a much more important level, it’s HUGE. Earning $140ish/month wasn’t going to change my life, but it would enable me to offer occasional free talks to schools without working for nothing.

A previously unsustainable part of my life was now sustainable, and there was now the possibility of growth—more people could always support me in future.

The project’s mere existence also led to new opportunities. A local charity heard about it, and we began offering mental health outreach to schools together. As a result, in 2019 I spoke to FIVE THOUSAND students about anxiety across the region.

Choosing the right gate

I don’t want to give the wrong impression. The point of this story isn’t “quit your job and crowdfund”. After all, it’s easy to imagine this tale in reverse: a Parallel Universe Me who tried and failed at crowdfunding for a whole year, trying to convince the many gatekeepers of the internet to support him, before growing despondent and giving up… and then discovering that the perfect job was there all along.

My first idea wasn’t bad. Even with hindsight, it wasn’t “the wrong gate.” And it wasn’t about passion. Either of those two jobs—or a third that, y’know, actually employed me—could have provided the fulfillment and the stability I craved.

The point is that fixation on a particular gatekeeper can be stifling.

The persistent failure was a signal to change direction. Instead of searching for the one company or person who I imagined held the solution to my struggles, I needed a fresh perspective: I could just go through a different gate.

Everything isn’t perfect now. Different circumstances always lead to different problems. But they also bring new possibilities. Perhaps I could aim to grow the crowdfunder and expand the mental-health-in-schools project. Or I could reverse direction and seek a full-time job. I could even resume the search for that perfect job which eluded me in 2018.

What to do when you’re coming up against gatekeepers

If you find yourself repeatedly being denied by the same gatekeepers, ask yourself:

• What haven’t I tried to get in? Is there a new approach that may work?
• Or is there another way to reach the same place?
• Do I really need what they’re guarding, or can I achieve my goals elsewhere?
• Or is there another gate that takes me somewhere equally good?

Whether you end up entering your particular gate or finding a different one, I hope that this year holds all the unicorns you desire.

Your Turn

Which gatekeepers have you tried to impress, and which have you gone around? Have you ever changed direction completely after exhausting all the apparent options? Share your stories with the community in the comments.