03/16 – Oakland
As a reminder, I’ve been spending each month in a new city. Month 1 was Seattle.
I spent month two in Oakland. It was a mess, rich in lessons and stress. The intention of spending time in Oakland was to see if I could handle living there and working in SF. tl;dr — Wonderful, but not for me.
… on living in Oakland
I abandoned Airbnb for this month and instead relied on the generosity of some of my friends that live in the East Bay (a HUGE thanks to Kevin & Christina, Kevin, & Roche, and Kevin & Chris for putting me up/up with me). It allowed me to see corner of Oakland I’d never visited before.
I spent a lot of time living with families. Dogs and toddlers were the topic of conversation across the board. This might be the most appropriate follow up to the single life of Seattle. Families have it tough, and the next few years will see most of my close friends move to this stage in their life.
… on Oakland itself
I was blown away with Oakland. I’d spent time in the East Bay before over the years, but only for a few hours here or there. I was able to hang out in neighborhoods completely off my radar. I found beautiful communities, good restaurants, tree lined streets stretching up into the hills with warm views back on to the foggy west side. Even the people were friendlier, without the same intensity of SF (a trend I’m seeing continue in New York, more to come on that).
All in all, I’m not sure why SF or the peninsula won. Oakland is lovely.
… on commuting to SF
Oh right.
The commute to SF is horrible. I tried all methods: BART, bus, ferry, Casual Carpool (amazed that this exists). All in all, you need to budget 1.5hrs to commute to SOMA. It can be 30 minutes but between transit breakdowns and traffic snarls, you can’t count on it.
- BART stations are nearly universally in crappy neighborhoods. Rockridge is the notable exception and Lake Merritt seems to be up and coming. This means you need to commute or uber TO the BART.
- But the reality is that BART doesn’t run with the frequency you need to rely on it, nor does it run at night. Most times, it’s crowded and delayed.
- Busses across the bridge are cheap and comfortable (some even have free wifi), and Casual carpool is a brilliant system that works surprisingly well. Both suffer from horrible traffic coming into SF.
There’s a lot of talk of the Brooklyn-ization of Oakland. I don’t think it’ll happen any time soon. I can tell you first hand that Brooklyn has far better transit.
Ultimately, this is what killed Oakland for me. I ended up moving back to SF for the last week and a half to avoid the commute. After being able to walk nearly everywhere in Seattle (and again now in New York), signing up for a commute is a hard no.
Work life
Last month, I was worried about not being productive enough. This month was much better. I spent most of my time working in SF, both doing customer development and, for lack of a less cheesy sounding phrase, “founderdating”.
It was illuminating to spend more time working on who to work with. I have a few lessons to apply to the old Marrying Your Friends presentation I gave a few years back.
So yes, Oakland won’t be for me, but it was comfortable to be back in SF and grinding again. Excited to see what NYC will hold. Then we can talk about how long this city-month experiment is going to stretch out.
