It's 10:52pm and I'm sitting on a red-eye from SFO back to Newark, waiting for takeoff. I'd been sobbing for most of the past few hours, because I knew I was about to make what felt like the hardest decision of my life. It’s March 2019.
Earlier that day I'd had my final round at Square, interviewing for the Investor Relations team. Square was scrappy then — about 3,000 people who all seemed to genuinely believe in the thing they were building. I was enamored. The office, the people, the bar the team held itself to. The whole idea of working at a tech company.
I knew I'd interviewed well and I knew the offer was coming. What I wasn't prepared for was what saying yes would mean: leaving New York, and leaving my boyfriend of three years.
Three weeks later I was on a one-way flight to San Francisco, after a farewell tour of late nights and as much Milk Bar as one body can handle.
That first year was rejuvenating. Demanding, all-consuming, and incredibly fun. The people made it and everyone knew that about Square.
Then one day in March 2020, I left the office carrying my computer monitor and never went back. COVID in San Francisco was its own specific kind of extreme, and the months that followed were uneasy. They were also the start of the most formative years of my life.
We had more than 25 earnings cycles, a company name change, a short seller report, multiple investor days, and marketing trips around the world. I built a strategy & ops function out of nothing, focused on reputation and defining an entirely new role at our company.
And also, I moved in with my boyfriend, got engaged, moved to Austin, got married, got a dog, bought a house, and had our first baby. And along the way there became a group of people became very best friends.
The work I loved most was ambiguous and cross-functional. Problems that don't have a clear home and moving them forward across various teams. That only works because of the people and Block is full of the best.
You hear about the 100x engineers. The ones whose output multiples everything around them. I’ve always strived to be that person. The one who gets the thing done. Who says they’re going to execute and does. Who manages upward and cross-functionally with complete ease. That reads the room and fully gets it.
I leave today knowing I gave it everything. And when people tell me I've made my mark, that I have a skillset they've never seen before, that I show up in a way they can't quite name, I smile. Because I know exactly where it started: with a girl crying on a red-eye, sure she was making the hardest decision of her life.
She was. It also turned out to be the best one.
This is such a beautiful reflection, Tori. What really stayed with me was the red-eye story and how different that moment looks in hindsight. Sometimes the hardest decisions are the ones that end up changing the course of your life in ways you couldn’t possibly see at the time.
Seven years later, it’s pretty amazing to look back at everything that came from that decision. The people, the experiences, the growth, and all the memories along the way. Sounds like you really made the most of the chapter.
Excited to see what’s next for you. 🚀