Timing... timing... timing.

And all the other powerful things beyond our control.

When I was fourteen years old, I attended my first Youth & Government conference: a model state legislature program run by the California YMCA that changed my life.

I remember getting off the bus at Camp Roberts and walking into a massive outdoor tent (colloquially called “The Bubble”) filled with 3,000 high schoolers from around the state. I sat down in plastic folding chairs next to the students in my delegation—the funniest “older kids” I’d ever met outside of baseball. Together, we listened to speeches from about a dozen candidates for Youth Governor, each one hailing from a different part of the state, each one laying out their vision for a better California, and each one seemingly funnier, smarter, and more inspiring than the last.

Despite the fact that none of this had real-world impact, for the first time ever politics wasn’t just entertainment. It was something I felt like I could be a part of; something I already was a part of. In a near-spiritual experience, I felt the collective energy of an entire statewide gathering of passionate future leaders, all of whom cared enough about making the world a better place to spend their weekend on a military base eating Potatoes O’Brien. Every speech I heard was a moment that 3,000 of us shared. It made each of us a part of something bigger than ourselves.

I didn’t know who let these 17 and 18 year olds up on that stage, but boy did I want to be one of them. So from then on, I knew that politics, government, and public service would be my path.

More specifically, I wanted to work in Congress and eventually the White House. More specifically than that, I learned I wanted to be a speechwriter. I wanted to spend a career recreating that moment of awe and optimism I felt in The Bubble. Not to mention that speechwriting meant I could do it without ever getting on a stage myself (no thanks!) and it’s what all those dudes on West Wing did.

So, I followed a well-trodden path. I studied political science for four years at a good school on the East Coast. I did two college internships on Capitol Hill (one in the House, one in the Senate, to really cover all my bases). And when I graduated, I even delayed actually applying to Congressional jobs on the sage advice that campaign experience makes you a more competitive candidate, instead spending my first six months out of college on a campaign in New York City (an incredibly prescient instance of good timing that will make more sense later).

Then, the campaign ended. I spent another four months applying to Capitol Hill jobs, collecting unemployment while bored and atrophying in my parent’s guest room like some no-good-deadbeat-bum (thank you Mom and Dad I love you), until I got a new job. Not as a speechwriter, but as a press assistant. Which is what I needed to be a press secretary. Which is what I needed to be a speechwriter. Patience. Your time will come, they said.

I worked another two of years in a grueling (and incredibly rewarding) battleground office in the U.S. House of Representatives. During that time, I even hustled my way into a very-part-time, unpaid gig speechwriting for the Biden and Harris campaigns—and no, they didn’t let me anywhere near the Head Honchos. I wrote for low-level campaign surrogates you have never heard of (MasterChef Season 6 winner Claudia Sandoval anyone???). None of it was the dream job. But I was doing the thing, and it would be my foot in the door for a Big Boy Speechwriting Job once we finally beat Donald Trump and kept a Democrat in the White House.

Then, he won all seven battleground states.

Out went a Democratic administration and (among so many more important and globally impactful consequences) all the Democratic jobs that came with it. I went from speechwriting abundance to scarcity because, to borrow a metaphor from that asshole who won all those battleground states, that’s just how the partisan tide rises and falls in The Swamp. I had felt that tide rising—believing in the momentum of Kamala’s ascendancy and the opportunities it would bring, at a time when I was approaching the ceiling of my current job and had cultivated all the right relationships for the next one—just before it fell.

This was the power of timing. And I was powerless against it.

---

---

Timing is powerful but elusive. Like a beast lurking in the shadows, we might catch glimpses of it as we move through the forest: a foreboding trend in the markets, a curious political poll, or reading the room while telling a story. We try our best to be alert for the rustling bushes of bad timing, or follow the tracks to where good timing might await. But we can never expect to tame it because it never presents itself until we least expect it. Timing always has the upper hand.

Ultimately, we’re all just dumb little humans wandering around in a dark forest… biding our time, making the best choices we can, just hoping things work out how we want.

I’ve never been very religious, but I do believe in things beyond my control. Timing is one of them. It’s as powerful a concept as any god I know. For all of human history, we’ve prayed for the rain to finally come, for that big investment to finally pay off, or for Jon Stewart to finally come across your new Substack and be so impressed he gives you a job. When these things do happen, you can call it divine intervention, sure. The answer to your prayers. Or you can chalk it up to good timing: the thing that happened right when it needed to happen.

Or, like the god I would believe in if I did, maybe timing isn’t good or bad at all. Maybe it simply is.

For better or worse, timing demands that we relinquish our agency over all the things we can’t control: the actions of others, global events, the weather, etc. But in doing so, we discover the things we can control: our attitude, our courage, and what we do next. It’s an exhausting process of trial-and-error to find the extensive but finite boundaries of our own power. We just have to submit ourselves to the whims of the Universe from time to time, hoping it sends us a wave we can learn to ride.

In my case, it meant months of stewing in the disappointment that I will not be a Big Boy Speechwriter quite yet, and that I will certainly not be working anywhere near the White House for a while. It’s not my fault, I didn’t do anything wrong, I didn’t fail to work hard enough or make (too many) mistakes.

It was just bad timing.

But more importantly, timing is a double-edged sword (and now, you can scroll back up to the mighty double-edged Clocksword I had AI dream up to illustrate my point).

---

Good and bad timing is everywhere, all the time, whether we like it or not.

I think back to five years ago, when a global pandemic shuttered a year and a half of my college experience just before my semester abroad—but then brought me to my first love and a wonderful long-term relationship. Or, twelve years before that, when my parents finally opened their own small business (my dad’s dream!) just months before the Great Recession. Or, four decades before that, when my grandfather happened to be fighting-age for a biblically pointless draft, but survived by (among a thousand other well-timed miracles) walking a few paces behind some other poor soul who didn’t get to come home.

Good timing, bad timing; bad timing, good timing. So the pendulum indifferently swings, crushing your dreams or saving your life.

And as much as we might think we have a knack for great timing, or a curse for awful timing, or some semblance of ability to tip the scale in either direction… most often the clock strikes for reasons beyond our control. If you bought Apple stock in 1990, are you a genius or just really lucky? Conversely, if you bought Tesla stock in November, are you unlucky or just a piece of shit?

But always remember, the Clocksword cuts both ways. And in my humble, ever-so-fortunately non-life-threatening case, it can cut you a golden ticket out of the city you like and back to the city you love—right when you needed it to.

I am happy to report that, while not quite what 14-year-old me imagined or hoped for pre-November 5th, 2024, I have a wonderful opportunity to try something new. It’s not speechwriting and it’s not in our nation’s capital. But it’s a job that let’s me continue fighting for progressive causes and hone my craft, despite Donald Trump and Elon Musk’s best efforts, particularly in a city that I know and love with all my heart.

Ollie’s moving back to New York City. For now.

In the end, I am incredibly grateful for my timing. I pray to the Clocksword every night. Not only because of the second-best case scenario I find myself in, but more importantly because what else can I be if not grateful for good health and—yes—any fucking job at all! Hallelujah.

I imagine this pending transition will influence a lot of my thinking the next few months, so expect some similar themes to come as I tease out these feelings. But for now…

---

As Timothée Chalamet once said, “the times they are-a changin’.” Ain’t that the truth. As my timing is brutal in one way, it’s also pretty good in another. And I might find months or years from now that it was pretty damn good. Who knows. I’ve got plenty of years ahead of me. All I know to be true is that things change—oftentimes without our own very important input—yet time goes on.

Better yet, life goes on. Thank god we get to live it either way.

Be well,

Ollie

P.S.

I recently read another essay, much better than this one, by Jared Young. It also captures the growing pains of chasing one’s dream and the illusion of achieving it before your time. It brought me to tears, and I highly encourage you to read it if you’re interested:

YOUTH

Have any good stories of good timing or bad timing? Leave a comment, because I wanna hear about it!