Mourning missing milestones
Today would have been my 10 year anniversary at Fastly. Instead it’s my 2 month anniversary at Fleet.
I’m happy where I am. Really happy. But I’m also mourning a milestone I’ll never get to celebrate.
Ten years at a company means something. It’s not just time. It’s relationships built, systems created, problems solved, late nights spent making things work. It’s the kind of investment that makes a place feel deeply personal. You don’t just work somewhere for almost a decade. You become part of its story, and it a part of your’s.
I helped build IT at Fastly from almost nothing. It was real work, the kind that leaves fingerprints all over infrastructure and processes that still run today. Watching that grow should have felt like watching something I helped raise.
Instead, I mourn.
The shift
The company changed around me. Not all at once, but slowly enough that I didn’t notice until I looked up one day and realized I didn’t recognize it anymore.
Leadership who deliberately misgendered me and other members of my team. Who didn’t see us as people but as interchangeable parts in a machine. Who saw my empathy as weakness. Who bragged to me about using ChatGPT in real time during interviews in order to get hired. Who gaslit me so thoroughly that I had to take a leave of absence for my mental health.
I raised these concerns with senior managemet. I was ignored.
I woke up one day and realized I’d been so deep in the weeds trying to survive inside a dysfunctional system that I’d missed the transformation happening around me. The culture I’d joined, the one that made me excited to show up to work every day, had evaporated.
What mourning looks like
I’m not mourning the company Fastly became. I’m mourning the company it used to be, and the company it should have become. The one I joined. The one where I built a team that I cared about.
That loss is real, even though I’m somewhere better now. Even though I made the right choice leaving. Even though Fleet is everything I hoped it would be when I joined.
You can be excited about the future and still grieve what you lost. Those feelings don’t cancel each other out.
There’s something particularly painful about institutional betrayal. Not just that the company changed, but that the investment you made, the years you gave, the belief you had, the relationships you built, all of it got dismissed, devalued, and dismantled by the very people who benefited from it.
Ten years is a long time to pour yourself into something. Long enough that it becomes part of your identity. When that relationship ends badly, you don’t just lose a job. You lose a version of yourself.
The milestone that isn’t
I won’t hit ten years at Fastly. There won’t be a congratulatory Slack message or a commemorative gift or a moment to reflect on a decade of growth.
Instead, I’m two months into something new. I’m still learning people’s names, still figuring out systems, still building the foundation for what my role could become. But here’s what I’ve learned in those two months: alignment matters more than tenure.
I’d rather have two months at a place where the values are real than ten years at a place where they became hollow. I’d rather build something from the beginning with people who care than maintain something broken with people who don’t.
Fleet’s empathy isn’t performative. It’s real. It’s lived every day. It’s what happens when I have to work from bed because my back is wrecked and nobody questions it. It’s what happens when I come up with ideas or raise concerns and people actually listen. It’s what happens when the handbook describes how things work and that’s actually how things work.
That alignment is worth more than any amount of time fighting to preserve something that’s already gone.
Moving forward
I’m not going to pretend the loss doesn’t sting. It does. I invested a lot of myself in Fastly, and I’ll never get that investment back in the form I expected.
But I’m also not going to pretend I made the wrong choice. I didn’t. I proud of the work I did at Fastly, especially early on. I got to work with some of the best people I’ve ever known. I’m grateful for the skills I built and the relationships I developed. I learned so many things in my time there.
But it was time to go. The water was boiling, and I was the frog. I got out.
Now I’m somewhere the temperature is actually comfortable. Somewhere I can grow without constantly defending my right to exist. Somewhere the culture I was promised in the interview is the culture I experience every day.
Two months isn’t ten years. But two months here feels better than the last two years there did.
That’s not nothing. That’s everything.
What I’m learning
Mourning isn’t linear. You can be thriving in a new place and still feel the weight of what you lost somewhere else. You can be excited about the future and sad about the past at the same time.
You can also recognize that some milestones aren’t worth celebrating. Ten years at a company that pushed you out, ignored your concerns, and made you fight just to be seen as human isn’t actually an achievement. It’s survival.
What matters now is that I’m not just surviving anymore. I’m building something again. With people who see me. At a company where the values are real.
That’s the milestone worth celebrating. Not the one that could have been, but the one I’m actually working toward.