Embracing Serendipity

“Bending Over Backwards” mural in The Mission, San Francisco

“Believe in serendipity,” my new friend, Sarah Seegal, said, as we sat at a coffee house in San Francisco, developing a list of venture capitalists who may be interested in investing in my healthcare startup.

“Serendipity happens.”

I was attending my first conference as my own brand, having been given a free pass by my mentor, borrowed money from my parents to book the flight, and spent the week couch-surfing at a friend’s house to save the hotel expense. Every moment was worth it. At that conference, and in city wanderings with my host, I met several of my personal heroes: people I consider luminaries, rock stars.

I was broke, I was hungry, and I was thrilled.

“Embrace serendipity.” That became my motto, and embracing it has been life-changing. I remind myself of it every day, in all kinds of situations. And Sarah was right: it does, indeed, happen. Don’t believe anyone who tries to tell you differently.

Breaking out on my own, I had to overcome the scars of being the girl who never quite fit in and felt very insecure about my place in the world. I was beat up and brutally betrayed by best friends in high school. I had a few vicious boyfriends in college. My career success precipitated my divorce. My post-divorce boyfriend told me I’d make a fine trophy wife, but I should spend more time on my body and less on my career ambitions; he wanted me to be his fan club.

It took far too long to disengage from the toxic people in my life, and even longer still to evict their echoes from my mind. There are times I wish I could have every one of the moments, let alone years, back that I wasted allowing my sense of self-worth to be defined by whether I could fulfill someone else’s wish-list for a friend, a girlfriend, or a wife. And then, I think about how freeing it was to finally find myself, and remember that I wouldn’t be who I am without those experiences.

Besides, let’s get real: I may have taken the leap into entrepreneurship in part out of spite for all those naysayers and their lingering echoes. Maybe in large part. Truly, I may as well have had a house-sized “Nanny-nanny-boo-boo” neon sign ready to light up at my first major victory. I’m sure someone would say that isn’t the healthiest motivation to have, and that might be true. The point is, I made the leap, right? And with time, it became far less about “showing them” and far more about “becoming me.”

Once I decided to take the leap, I realized my local, albeit rich, network of industry connections would not be sufficient to scale the company I had in mind. So, I turned to social media. I’d owned and built a number of internet forum websites over the years, so I had a familiarity with the power of social communities and connections. I’d long leveraged LinkedIn to find and maintain professional connections, but I hadn’t used it any more broadly than as a virtual Rolodex. And I’d heard of Twitter, but hadn’t ever tweeted. I understood the concept of hashtags, but had never intentionally used one.

After creating my account and spending a few days scanning search results and reading tutorials from social media Jedis, I took to Twitter like a duck to water. I began tracking dozens of conversations on topics of interest to me: healthcare, big data, analytics, health IT, health, fitness, wellness, information management, information governance. I identified consistently strong voices in those conversations, and began following and engaging (or, at least, attempting to engage) specific individuals like John Lynn (@techguy) and Dr. Wen Dombrowski (@HealthcareWen). I participated in tweetchats that aligned to my interests, or where I saw those strong voices contributing.

Organically, my network of connections grew. One of those first strong voices that I followed, parroted, and intently provoked into response, Brian Ahier (@ahier), gave me the free pass to the StrataRx conference in San Francisco where my story began — all because we’d engaged on Twitter. To this day, I’m not sure if he gave me that pass purely for the entertainment value of watching me swoon over the speaker roster. And swoon, I did. I also crashed speaker tables at multiple sessions, and ended up sitting next to industry legends like Tim O’Reilly (@timoreilly) and Vinod Khosla (@vkhosla). I know I wanted to have meaningful conversation with them, but to this day, I can’t remember a word that was said; I was too star-struck to do much more than ask for a selfie.

Me and Tim O’Reilly, founder of O’Reilly Media and genuinely cool cat

In the years since, I’ve found myself at numerous conferences and industry events, amidst these people I admire — and as the time passes, I’m increasingly engaging with them as peers, people, friends, rather than pedestal inhabitants. Once, in a highlight of my life, let alone career, Dr. Karen DeSalvo (@KBDeSalvo) saw ME across the room at a conference, and had her assistant take a picture that SHE then tweeted. ME! She asked ME! (I won’t say it wasn’t due to my shrieking in delight at her mere proximity — she is simply an incredible woman and someone I can only aspire to emulate. Especially since she was wearing fabulous leopard-skin shoes. But the facts still stand.)

One of the highlights of my professional life: meeting Dr. Karen DeSalvo and having HER tweet about meeting ME!

Occasionally, I’ll have a shocking moment of realization when I find that I’ve become someone else’s “Brian Ahier” by virtue of a serendipitous connection that we’ve made, and that engagement sparked a change.

Fast forward to last month, when I was invited to my first “round-table” event: a kind of super-secret geek society meeting that I was always jealous of my friends for attending. I’d always imagined insane levels of brain power magically streaming through closed doors during those sessions, effecting change through the palpable passion of the participants. And somehow, serendipitously, I was invited to attend one.

Reflecting on the experience, I wasn’t too far off in my fantastical assessment. Here I am, sitting near the head of a large conference table, surrounded by the same types of heroes and luminaries I’d only ogled at my first conference — and I’m part of the group. I have a seat at the table. I was incredibly proud of myself for not fan-girling so much that I annoyed my hosts. (At least, if I did, they were graciously silent.)

I didn’t ask for an invitation; I was invited because someone at that table felt that I would add value (thank you, Fred Trotter (@fredtrotter)!). And now, I’ve been invited to another one. Years ago, I embarked on this journey seeking only knowledge and guidance; I have since found community and kindred spirits. Finally, I’m finding a community where I feel I can fit in. Like the day I discovered I’d been listed just beneath Madeline Albright on Rock Health’s list of Female Role Models and Mentors in Healthcare

And last week, I hosted a healthcare think tank event of my very own, with industry rockstars and amazing minds collaborating on healthcare transformation challenges and opportunities.

Dell #DoMoreHIT Think Tank panelists pre-show on 3/16/15

Serendipity happens. Embrace it.

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