435 Days
On Unemployment, Imposter Syndrome, and Neighbors Who Cut Trees
It's been 435 days since I last had a job.
I know that because I’ve been counting. I counted at 303, once again at 356 days, and then counted some more at 422. I wasn’t sure I’d get to stop.
But today, I do.
Two days ago, I accepted an offer from an AI company in the e-commerce space—some pre-seed startup with a mission statement about “advanced attribute technology” or whatever buzzword salad they're serving these days. The irony isn't lost on me that after hundreds of applications, what finally landed me this gig wasn't even my own doing—it was Niru, my old colleague from Yahoo! circa 2005, reaching out to me out of the blue. Twenty years later, our shared trauma of surviving the early aughts tech bubble is still paying dividends.
They didn't waste any time either. The very next morning, I found myself in their sprawling house in the Fremont Hills, sweating through an intense whiteboarding session. Nothing says "welcome to startup life" quite like architecting a component hierarchy while the CEO's dog sniffs at your ankles.
“I told you, just be patient,” Mom says over the phone after I tell her the news. “My son always lands on his feet. When are you starting?”
“I started,” I tell her, raising my voice to compete with the Taiwanese news blaring in the background at volume 11—her hearing aids are apparently just decorative accessories at this point.
"What's the salary?" she shouts back as an anchorwoman dramatically details what I assume is either a political scandal or a typhoon report. It’s Taiwan, so it’s probably both, with added wacky effects via a soundboard for good measure.
I hesitate. This is where things get complicated.
“It's... pre-seed,” I explain, knowing full well she has no idea what that means. “They haven't secured venture capital funding yet.”
"So they're poor?" she asks, cutting through the Silicon Valley euphemisms with immigrant directness.
"They're not poor, they're... early stage." I can practically hear her eyebrows raising through the phone. "Yes, it's below market rate," I finally admit.
"You'll succeed if you work hard," she says with absolute certainty, her voice competing with what sounds like a breaking news update. "But you know what else would help? If you lost some weight. You're still fat. You need to exercise more."
Before I can respond to this whiplash-inducing pivot, she's already moving on. "Can you believe what the neighbor did? They cut part of my tree! MY tree! It was only a little bit over their fence, and they just... cut it! I was so angry I called the police."
And just like that, my employment status—the thing that's consumed my every waking thought for 435 days—has been reduced to a brief interlude in the ongoing saga of Mom vs. The Neighbors.
I'm almost grateful for it.
The application that landed me this job wasn't really an application at all. There was no desperate late-night text from me this time—no pleading email or carefully crafted cover letter. Instead, it was a message from Niru that appeared in my LinkedIn inbox one random Tuesday: "Hey stranger, my friend's startup needs a front-end dev. Still coding?"
After, like, 186 actual applications tracked in an unnecessarily elaborate spreadsheet—color-coded by response status, with formulas calculating my interview-to-application ratio and a line graph showing my steadily declining salary expectations—the job that finally came through wasn't even one I applied for. It found me.
The universe has a twisted sense of humor that way. All those hours perfecting my portfolio, all those tailored resumes, all those follow-up emails that never received responses—and in the end, it was a casual message from someone I worked with two decades ago that led to a Google Meet call that felt more like catching up than interviewing, and then an offer to join a company that might not exist in six months.
The most stable job opportunity I've had in 435 days came from the least stable company through the most random connection.
Sometimes, I have these conversations with the version of myself who hasn't been beaten down by 435 days of rejection—the one who still believes everything happens for a reason and setbacks are just setups for comebacks. He sounds disturbingly like my ex during our better days before toxic positivity made my eyes roll to the back of my head. That relentless optimism was one of his best traits, even when it drove me crazy.
It's actually perfect timing, Optimistic Ernie would say. The AI boom is happening right now, and you're getting in at the ground floor of a company that could ride that wave.
Yeah, or wipe out spectacularly, I counter.
Either way, you're back in the game, he'd insist. You're coding again, building your skills, and making connections. Six months from now, you'll be more employable whether this company succeeds or not.
Or I'll be explaining another short stint on my resume, I'd argue back.
A short stint at an AI startup still looks better than an increasingly large employment gap, he'd remind me. And who knows? Maybe they'll get that funding round. You'll help build something amazing. This is exactly where you're supposed to be.
I hate how reasonable Optimistic Ernie sounds. I hate how much I want to believe him. But he's not entirely wrong. This is an opportunity—maybe not the opportunity I would have chosen, definitely not the salary I would have negotiated from a position of strength—but an opportunity nonetheless. A chance to reset the counter. A chance to answer "So, what do you do?" without wincing.
The truth is, I'm terrified. Not because the company might fail, but because I might fail. Niru recommended me as "a superstar UI developer"—in 2006. She took a chance on me based on skills I had nearly two decades ago, and now I have to live up to that reputation.
What if I can't? What if my brain doesn't pick things up as quickly as it used to? What if I'm too tired to pull all-nighters learning new frameworks? What if I'm just... too old for this?
The imposter syndrome I've battled my entire career hasn't gone away—if anything, 435 days of rejection has amplified it. Every time I open my laptop now, there's this voice in the back of my head: "You got this job because of who you were, not who you are."
But I've been working on who I am. I've spent the past year upskilling—diving deep into AI, taking a ridiculously expensive "become an AI consultant" course that costs $350 a month (which I'm now debating whether to continue paying for), reading everything I can get my hands on about current front-end development practices. I've been putting myself out there with my writing, trying to build some reputation beyond "that guy who used to code."
The problem is none of that looks like "real work" on a resume. It looks like what unemployed people say they're doing when they're actually just watching Netflix in their pajamas. Even though I know better—know how many hours I've spent learning, writing, and trying—I still feel the need to apologize for this gap, explain it away, and make it seem like anything other than what it was: 435 days of trying and failing to convince someone to hire me.
My resume now has this weird gap—this 435-day hole that I'll need to explain in future interviews. I've rehearsed the sanitized version: "I was upskilling and diving deep into AI," "I was working on personal projects and exploration," and "I was taking time to find the right fit."
The real version sounds more like: "I was watching my self-worth erode one rejection at a time while coming to terms with the fact that tech values youth and recency over experience and perspective."
But today, at least, I don't have to explain the gap.
Today, I'm employed.
Today, I'm a front-end developer at an AI company in the e-commerce space.
Today, I can update my LinkedIn profile to something other than "Open to Work" with that sad green border that might as well read "Please, Someone, Anyone."
It's been 435 days since I last had a job. There are 365 days in a year.
But who's counting? Not me. At least not something happens again— until the runway at this pre-seed startup runs out or, god forbid, life throws me another surprise I didn’t ask for. Then I'll start counting again because, well, you know me at this point, right? I never really stop counting, do I?
But for now, for today, the counter resets to zero.
I needed an employment success story today. Thanks, and break a leg, Ernie!
You're no imposter.
Loved this from beginning to end. The humor, the fun, yet the unbelievably real emotions here. 🧡