It Was Never Mine
On recovering from disappointment
I pinned all my hopes on April 6.
In a perfect world, Don would receive an offer on my mother’s house and I’d receive an offer for a job on the same day. The two puzzle pieces I need to move forward independently with my life—a significant amount of cash and my own steady income/health insurance—were both set to fall into place.
It was a lot to ask of the universe, but how poetic would that be?
Only one of those dreams came true. Don accepted a fantastic offer on the house just four days after it hit the market. The buyers are a young couple who just got married last year; this will be their first home. I couldn’t dream of better people to bring fresh energy and love into a place that means so much to my family.
If all goes according to plan, Don may be signing the final documents on April 30—my mother’s birthday. Talk about poetic.
The other puzzle piece disintegrated before it could hit the table. For the past few weeks, I’ve been interviewing for a job at a household-name software company. I made it all the way to the final round and presented a slide deck to a panel of three people. I received only positive feedback and felt more confident about this opportunity than any of the others I’ve interviewed for.
Alas, the role went to someone else.
I’m disappointed. But I know I gave it my best shot and couldn’t have done anything better. This would have been a career pivot for me, and I’ve confirmed the winning candidate simply has more experience doing this type of work than I do. I can’t beat myself up when the most qualified person got the job.
For a few glorious days, it felt like mine to lose. But, to borrow a concept from Taylor Swift’s song “august,” I remind myself: It was never mine.
I believe what’s meant for me won’t miss me. The right opportunity is still out there; I just haven’t found it or created it yet. I’m one “no” closer to my “yes.”
At times, it’s frustrating to not know exactly what that is yet. Is it a corporate 9-to-5 job? Is it continuing to grow this newsletter and pitch publications and write a book someday? Is it some secret third option I haven’t considered yet?
As with all things in life, the magic is in the mystery. I can spend my days desperately scrambling for all the answers, or I can send my best efforts out into the world and feel confident the right things will hit on some cosmically predetermined schedule.
It’s a strange time to be looking for work as a writer. Creative jobs continue to evaporate amid the nuclear blast of AI and automation, and untold numbers of us are scrabbling for the few that remain.
Nearly the entire writing team at my previous company just got laid off, including both of my former bosses. These are people who dedicated 20, 30, 40 years of their careers to this company—axed in a day. I’m certain it would have been me, too, if I hadn’t chosen to leave 17 months ago. I saw the LLM-generated writing on the wall.
Human creativity is endangered, not because it lacks abundance, but because it’s increasingly undervalued. Why would anyone pay a human to do something a robot can do better, faster, cheaper?
That’s part of what makes me so proud to earn money from this newsletter. Maybe AI can write a more compelling, emotional story that I can, but it can’t have the lived experience behind it that people really connect with. It will never have a soul.
I do my best writing when I pry open an emotional wound and spill my guts onto the page. As painful as it can be, this has always been vital to my healing process: inviting others to bear witness to my human experience. Now it feels like an act of resistance, too.
I can’t compete with a robot. I choose to stay flawed and fallible and a little fucked up instead. My hope is consumers will continue to value these attributes in all forms of art.
There have been a few instances when I’ve heard a song I liked on Spotify, only to look into the “artist” and discover the music was generated by AI. I felt violated. How disgusting to steal streams from human artists who’ve been grinding for years to spill their guts to the world. How sterile to use an algorithm to calculate the beat and melody and instrumentation and lyrics that would inspire authentic emotions in unsuspecting listeners.
Maybe some people don’t care. Maybe they think good music is good music, no matter how it was created.
I care. And I don’t know what to do about it, other than to make sure my consumer dollars are going to real people rather than robots, to support companies who prioritize human creativity over soulless profits, and to encourage others to do the same.
I accept AI is here to stay. It is expanding—largely unchecked!—by the minute. (If you’re craving a complete panic spiral, I recommend this episode of The Oprah Podcast on Apple Podcasts or YouTube.) Creatives of all stripes must adapt or die.
My best bet is to apply my writing and editing skills to a different type of job that still requires plenty of human ingenuity and can’t be so easily replaced by a robot. Or to keep grinding with relentless authenticity and trust that the pendulum of what we collectively value will swing back in the direction of unadulterated humanity.
Either way, to my fellow creatives, from one of the best:
Do not go gentle into that good night.
Rage, rage against the dying of the light.
—Dylan Thomas
If you enjoy reading Rollercoaster Road, please help it grow by liking, sharing, or leaving a comment. Thanks for joining me on the ride.


