In a case of something like "Where in the world in Carmen San Diego" I find myself back in NYC. While my family and yacht club, not to mention America's Cup activities begin, I watch from afar in a city that has challenged me but always been good to me. When I first left San Francisco for the Big Apple back in 2011 I left almost abruptly. Okay, entirely abruptly. I left a fully furnished apartment, a half dissolved personal relationship and garaged car to chase Esther Dyson and try to get legs to my idea of what ConsumerBell would be. I likely skipped too quickly on the relationship I was in (he is now married) and definitely left things hanging with my family. When I eventually flew back to SF I simply packed my apartment and flew back to NYC within 48hrs. WORK TO DO.
Flashforward to last fall, I was coming to SF often; mostly to be around the smartest founders I know (Isaac Hall, James Tamplin, James Smith, Kathryn Minshew, my CTO Wing Lian and VC Gus Tai) and maybe to help lick some wounds too and find another co-founder per the urging of Mitch and Freada Kapor who only invest in local companies.
I found myself getting locked into a lease for an awesome SOMA apartment which wasn't all that bad, and by locked I mean my apartment in Gramercy had no power and I was under the siege of Hurricane Sandy with no cell or power but I knew my landlords in SF were forcing me into a lease. Okay, time to move.
1) It gave me a place / home to be in SF and
2) I lucked out with an awesome NYC ex-pat female founder roomie Cheryl Yeoh. The stars seemed to align to my ignorance and I was so quickly "back" in SF that it was all of a sudden it was a permanent move. After announcing I was back in SF, I spent tons of time with family and catching up with the yacht club, and in hindsight closing some personal chapters that were needed. I gave myself a couple years on the west coast before heading off to grad school abroad or some totally drastic life change.
But life changed.
I still spent a good amount of time flying back to NYC often sometimes even every few weeks and for weeks at a time. Some of our biggest leads and potential acquirers on the East Coast and then I wanted to be with my "friends" kept me coming back. All my friends in SF were either having babies or running startups. All my friends in NYC were exactly were I was: still hustling. So after all the drama of being locked into a lease I was quickly released and my solid SOMA lease became un-renewed in a month that was packed with traveling plans and all of a sudden my "couple year plan" turned into a brief stint without time to find the next place. I had dreams that I would meet "Mr. Right" out in San Francisco but it turned out that I knew everyone in SF and any awesome exs were already hooked up. Add my traveling and time spent back east and its true: you cannot build a life where you are not at.
My "soulmate" was not presenting himself in my hometown as I had expected. Instead there were flakey, peter-pan offers of happy hours and tech meet ups but nothing substantial that involved a sleepover or meeting my family. Granted me flying away every other week didn't help either, but I also didn't want to stay for superficial SF-style plans which like the rain forecast generally fell around 9% of occurrence. NYC was guaranteed to be there. I once even flew back from LA in time for a concert (date with someone) only to have him show up 2 hours late complaining about his own job. Another time I flew back from NYC for someone bugging me about when I would be "in town next" only to have him schedule something a week and a half after I got back in SF.
Why couldn't we have calendared that from NYC? Why did I have to be "back" for a date 9 days away? I wasn't getting it and that's okay.
Kathryn after finishing Y-Combinator moved back to NYC and just as I saw my routine in SF it wasn't exactly something worth living or expanding my reach: Monday thru Thursday I woke up at 5am PST to answer emails and requests from back east including our investors, and worked out close to 3 hours a day, which meant by night I didn't want to "party" nor could I anyways as I was exhausted from getting up early. Then there were the weekends: If I wasn't on a boat for Race Committee for St. Francis Yacht Club, I was with my family out in Discovery Bay usually thursday or friday night. My "life" was something like a healing mode of normal, to remind me of what I have but it started to inspire me once again of what I needed: more professional traction and while Silicon Valley is the mecca of fundraising it is not the mecca of hustling, NYC is.
So while "living in SF" I spent most of my time in NYC.
May rolls around (count the months: "technically" I was back in SF Nov '12 til May '13) and I'm losing my SOMA apartment right before America's Cup with zero time to find a new one and my first true vacation ever lined up (St. Maarten) and my NYC apartment is gone. Okay universe. I get it, I will stop planning. But is NYC where I need to be? Maybe I just need a road trip. And similar to a road trip I took with Leslie Bradshaw a year earlier I decided to pack up my things, put them in a guest bedroom in a family members house and hit the road. Why not? I'm single, un-attached and as long as I am available during EST hours my startup should be fine.
I was only suppose to be in NYC for a week.
Then my cousin in Orlando broke up with her boyfriend. Then our sales team in Orlando started to fall apart, then my flights to other cities were worthless and the idea of going to Miami to visit Leslie seemed less appealing when I had shit to figure out. I did have an AMAZING offer to participate as a Fellows for Cisco Live in Orlando which I kept on the calendar but as the dates got closer one of my investors ushered me to an annual Product Liability conference in Chicago I attend every year. By this time I had a sublet in Midtown West and was working on opening our Park Ave office as well as some other not so fun business items for ConsumerBell and after I got back from Chicago I realized I needed to focus: all traveling cancelled. Even Cisco Live which I sorta regret.
Since then its been one miracle after another. Another opportunistic door opening and I find myself signing more and more important things on behalf of ConsumerBell. One particular founder has been blogging that his startup is dying in 30 days, yet I feel like I'm the startup that won't die. No matter how many hours I spend in yoga or how many breaks I need- I still work more than the average bear and our mission still very compelling.
I've had bouts of suicidal thoughts. I have a couple physical health issues too from working too much going on. But guess what, all my doctors and therapists are here in NYC.
Yet, its different this time back in New York. I'm not afraid to call it home. I'm not on an airplane every other week and I'm not pretending to have two lives. I have one, it is here. I have family, it is there. They are not in the same location but I am not trying to be in two places anymore or two people.
I have spent so much of life planning, planning for all the right steps and even though I seem to always make my goals they never happen in the order that I predict. So I stop being a project manager and start being a person.
Big step. A year ago I would have told you I was miserable in two cities.