Three Lessons from Three Years of Bicoastal Living

It was June 2023, and I was about to drive across the country, two dogs in tow, leaving the Oakland apartment I'd lived in for 10 years and heading to New York City — without an apartment and knowing only a handful of people. I'd always loved New York and traveled there roughly twice a year for fashion tradeshows back when I was running my boutique. After surviving the Covid lockdown (and, unlike a lot of my friends, staying put), I felt like I was emerging a different person than I'd been in 2020 — and that deserved a life change. Realizing just how short life can be gave me the kick in the butt I needed to finally try living bicoastally. My people, my business, my network are all in Oakland — the Bay has been my home for all of my adult life — so I didn't want to leave it all behind. But I was ready for the next adventure.

Like most things, once I decided I was going for it, it became a series of figure-it-out challenges. Hmm, I can't afford to pay two rents — what if I sublet my place? My big dogs can't fly — what if I drove? All of this required a lot of flexible thinking and questioning assumptions I didn't even know I had. Of course, in retrospect it's easy for me to say, "Look, it all worked out!" But I can guarantee you I wasn't feeling that way at the time. There were the expected challenges, like being the weird adult trying to make friends in a new city, and the unexpected ones, like the Airbnb I booked for my arrival IMMEDIATELY having bedbugs. Looking back, though, I can't say I'd trade any of it, because it brought me to a place where I can genuinely say I'm living my dream life.

About a year ago, I was featured in a piece by the San Francisco Chronicle (and video) about creatives living bicoastally between California and New York. I stand by everything I said in that article, but a few more lessons have crystallized for me since then. So if you're considering living bicoastally — or just making a big life shift — here are three things I learned that might help you, so you don't have to learn them the hard way like I did.

Lesson #1: Wherever you go, there you are

There's this romantic idea that moving to a new city means becoming a new you. And to some extent, it's true. We're ultimately the accumulation of our habits, and a new environment forces you to adapt and create new ones. But we're also creatures of habit. If you didn't go out and socialize in your old city, you're not likely to do it in your new city without a concerted effort. You don't suddenly morph into a new person with all your problems left behind, because wherever you go, there you are. The change won't make you a new you automatically, but it does give you a chance to rethink your choices and experiment with new identities.

After years of living between Oakland and New York, I've actually found that place has become slightly less important to me. Every place is just a series of trade-offs. Sure, New York has amazing transit, but it's also crowded and hard to get to nature from. California's transit is awful by comparison, but you can take a 30-minute bus ride and be among the redwoods. It's about figuring out which trade-offs are worth it for you. And when things around you are constantly changing, and you're regularly adapting, developing self-trust matters more than ever. Learning to be at home in yourself becomes essential when you don't always quite remember which city you're waking up in.

Lesson #2: Trust in the universe

For as much as I'd like to think I can control things (yes, I'm a Capricorn), I can't. Living bicoastally has been an incredibly humbling reminder of this. For example, I love going to concerts and hearing live music, but it seems like I'm perpetually on the wrong coast. A couple of months ago, I was bummed to miss a show with Shabaka (a really amazing jazz musician) in Brooklyn while I was in California, at a venue I love, with an opening act I also love, Kamaal Williams. Oh well, chalk it up to the game. But lo and behold, three days before I left New York for Oakland, he was performing in Central Park (for free!)alongside Kokoroko.

I know a concert is a minor thing, but things work out with the big things, too. Finding my New York apartment was a fluke of the universe. I needed a new place and was absolutely dreading the horror that is a New York City apartment search. The good ones are mobbed with people, and the bad ones are still overpriced. In passing, I mentioned to my friend Arikka how much I was dreading the process, and as it turned out, her best friend from Stockton was moving from New York to LA for work. The timing worked out perfectly, and I got his very well-priced (not to mention furnished!) apartment. You never know what will happen. Just trust that things will work out the way they should, when you put in the effort.

Lesson #3: Time is short. Did you have fun yet, today?

I split my time between the coasts by season: Spring and Fall in New York, Summer and Winter in Oakland. It's mostly weather-driven, but it also happens to line up with my workload, galas, conferences, and the rest. Three months in a place is just long enough that you don't feel like a tourist, but short enough that you really don't want to waste any of your precious 12 weekends. With that constant reminder that time is short, I've learned that fun can't be postponed.

When we're on vacation, part of why we feel so free is that we prioritize fun! Living bicoastally makes me feel like I'm on a sort of eternal vacation, always chasing ways to live a lot of life. Sure, I actually live in both places, so I still fall into the same bleh feeling we all do (do I really want to order delivery from the same place yet again?). But I'm constantly reminded that I'm living in someone's dream vacation destination. Lots of New Yorkers dream of running away to California, where we have nature's air conditioning and wide-open spaces. And lots of Californians wish for the excitement and opportunity of New York City. Even if you don't live in a big city, your current life is someone else's dream existence. You have to choose to fully experience where you are.

Go for it!

There will never be a day when someone says, "Okay, NOW you have permission to have fun." As Covid made so evident to me before I embarked on this journey, life is incredibly fragile and incredibly short. We deserve to actually enjoy our lives, not treat enjoyment as a reward we get for finishing our work. So if you have a big dream — whether it's moving to a new place, going for that promotion, or starting that business — maybe this is just the sign you need to go for it.