Moving… Again

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Almost 5 years ago, I packed up my life in New Zealand, said goodbye to friends and family, and jumped on a plane to a place I’d never been to before; my new home, Seattle. What followed has been the most exciting and rewarding period of my life, both personally and professionally. I’ve made this place my home. Made a lot of new friends, grown enormously, and immersed myself headlong into everything Seattle has to offer. It’s therefore bittersweet to say that this chapter of my life is soon coming to an end.

Today, I handed in my resignation at Microsoft. In a couple of months, I’ll be moving to New York City.

What’s happening?

I’ve accepted an offer for an opportunity with Oscar. They’re a young company in the healthcare and health insurance space. This is truly a broken industry in the US, and something I feel passionately about — so I’m excited to be part of a team that’s legitimately trying to make things better for the end consumer. They’re using technology and data to make insurance more user-friendly, more transparent, and to bring down costs for everyone. I’ll be working in a developer role on the product’s back end.

My first day will be November 2nd, which means I have a couple of months off to wrap up my time in Seattle and do a little traveling. I’ve got a solid three weeks with my siblings in town, then a trip to California, and finally I’ll ride my motorcycle across the country to my new abode, wherever that ends up being.

Why are you doing this?

First and foremost, I’ve been at Microsoft for 5 years on roughly the same team — I’m definitely ready for a change. Microsoft has been a great place to work and I’m really appreciative of the opportunities I’ve had, but I’m yearning to be back at a smaller company. This comes with several benefits:

  • A younger, more fast-paced and energized workplace
  • Opportunity for greater impact and influence over a product (Oscar only has ~50 engineers currently)
  • Fewer structures in place — i.e. more flexibility in role and less politics

There is some risk associated with a smaller company, but I feel this is the stage in life when I should be taking those risks.

And the reason I’m most conflicted about… I really, really love Seattle. It really clicks with the person that I am, and I could see myself living here indefinitely. But I’ve really only lived in two cities in my adult life (Seattle and Auckland). I want to give myself the opportunity to try somewhere completely different for a while. NYC fits the bill (certainly more than SF, which I also considered). Again, this is something I feel I should be doing now — while I have few commitments in terms of family, property, etc. I’m planning to give NYC everything I’ve got for a couple of years, and reassess how I feel at the end of that time. There’s a decent chance I’ll be back in Seattle — and I’ll certainly be visiting a bunch.

Moving on

Finally, I know I’ll be catching up with most people before I leave, but I want to make a heartfelt thanks to everyone I’ve met in Seattle who has helped make my time here so awesome! You are all truly the reason Seattle has been so good to me. I’ll miss everyone a lot, and hope to see a few of you out in NYC! Although I’ll probably be living in a shoebox (immersing myself in Manhattan life), I’ll endeavor to always have some couch space or floor space for anyone that wants to visit. Seriously, you guys are all incredible. Drinks are on me.