Live Better
A Year In Jail
A year of applications, silence and rejection can feel like confinement, especially when forward motion has always been part of your identity. This essay reflects on a difficult season of career uncertainty, where effort did not guarantee outcome and experience did not automatically open doors. Yet beneath the stillness, something was changing. Rejection became information, silence became less personal, and the work of rebuilding continued quietly.
So it was not a holding cell or even a stretch, but it was a year that felt just as confined, just as isolating, and just as hard to explain to anyone who hadn't been there. Eight hundred applications, three interviews and three rejections.
I am no graduate finding their feet, but someone with two and a half decades of experience, qualifications earned, certifications held, and the scars to prove it. Still hearing nothing back.
At first, every 'unfortunately' I heard or read hit hard. Then they stopped hitting at all, and the silence became normal. Recruiters who were warm one week disappeared the next. Applications vanished into hidden algorithms.
A friend told me it probably hit harder for me than most, he explained, it was because I've been so driven, focused, goal oriented. Hmmm, yeah, maybe he was right in lots of ways. Forward motion was my default setting for years, abd being forced to stop felt painful and confusing. It felt like I had failed and did something distractly wrong.
What I didn't understand at the time was that I was inside a chrysalis.
A caterpillar doesn't just rest in there. It dissolves before it transforms.
That year, parts of me dissolved. The assumption that effort guarantees outcome. The belief that experience opens doors. The identity of being the one who always lands on his feet.
And yet, I kept building. I wrote. I coached. I made some pretty cool music (let me know if you want to hear some). I built productivity tools nobody asked for. None of it felt significant. Looking back, it was doing something quiet and important — rebuilding patience, adaptability, and the ability to keep working without immediate validation.
Eventually, rejection stopped feeling like a verdict and started feeling like information. Silence stopped feeling personal. I started adjusting, experimenting, refining.
I was quieter and stiller but not stagnant. There's a difference.
My advice to you is to keep building, even if no one is watching, and especially then.
But, if you'd like help working out what your next move looks like, reply to this email or reach out directly. That's what I'm here for.
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