The best thing I did this year

Two years ago my life was falling apart.

Bankruptcy, divorce, losing my mom to a 4 ½ year battle with ovarian cancer.

I was, almost literally, unmoored. I remember thinking, this is what it feels like to be a ship lost at sea without a way back.

“I want to go home” constantly looped in my head, but I didn’t know what it meant or how to get there. I drank too much, worked too many hours, and tried to stay afloat. My heart was broken. Some days it still is.

This is often what I think about when I see people doing destructive things to themselves or others. Sometimes it’s a small heartbreak and sometimes it’s big.

We don’t do ourselves any favors when we try to deny that heartbreak. I resist the idea that we can gloss over our problems or concerns, or that anyone is doing life better than anyone else. There isn’t a formula, algorithm or app in the world that can tell you how to be human.

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Men, Women, Tech: Building structure that acknowledges how things are + how they could be

I have a hard time watching women cut other women down to size.

For me it’s painful because I recognize that the hardest thing to overcome in any group of humans is when an insider or influencer calls out someone else as “not a real [line in the sand of your choosing].”

I wrote a more personal piece about this back in April when I addressed my discomfort with Dove’s “Real Beauty” campaign.

In that model the very thing that’s supposed to ensure legitimacy — hey, this is someone who’s been there and done that, truly one of us — is used as a weapon against or seperator of other people in the group.

For women in American culture this is a constant problem and it’s embedded in a variety of forums, including the workplace.

As a member of the startup / tech ecosystem, I think about these things a lot. Even in a very far forward part of the economy the concepts of access + “how it’s done / what’s normal” are still strong currents, and instutionalized “isms” are at play. I won’t get into a huge discussion of how that works here, since there are other people doing it better (for a thought provoking, but NSFW [language + trigger warning] run down, check out @Shanley’s piece on how women in tech end up reinforcing patriarchy. I don’t agree with everything she has to say, but there are some indictments there that are hard to refute.

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“I want every version of a woman and a man to be possible. I want women and men to be able to be full-time parents or full-time working people or any combination of the two. I want both to be able to do whatever they want sexually without being called names. I want them to be allowed to be weak and strong and happy and sad — human, basically.”

Awesome quote from Natalie Portman via Feministing

Where does “Outsider, 2009-2013” go on a resume?

Living on the margins is not something you put on a resume.

Most of the time it’s not considered an asset in any area of life. The only upside (“s/he knows a lot about life”) often ends up being a backhanded compliment, or an expression of pity.

The truth is that being an outsider is terribly lonely, even if you are good at switching between people and environments.

For example, one thing that gives me credibility in a workplace (a fascination with quick translation, and assessing complex ideas/tasks) makes for a difficult experience socially. I can talk all day about work and be fine, but I’m way too intense and think-y to feel comfortable in most social situations. Of course I’m fairly good at blending in, but that’s different from actually feeling like you belong somewhere.

Over time I’ve learned to embrace being strange, but there’s still plenty of friction. I went on a date a couple of months ago and the woman I had a beer with labeled me a “formal hippie” (whatever that is), and said I was too serious and a snob because I’d mentioned that I wanted to spend my time with people who were passionate about something in their lives.

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The only piece of advice I’ll ever give recent grads

Since I work in the startup capital of the world, I’m constantly hearing elevator pitches.

If you’re not familiar, the idea is to explain what your business idea is in the time it takes to complete an elevator ride (typically 60 seconds).

After four months I’ve heard somewhere in the neighborhood of 50 of them (I go to a lot of events), so you can imagine that someone who’s lived and breathed startups for several years has probably heard thousands, if not tens of thousands.

It got me thinking about what makes an elevator pitch stand out and how I  synthesize not just my professional aspirations, but larger life goals too.

While I don’t personally subscribe to the idea that we’re selling ourselves constantly I do think we are explaining, or not explaining, our value more often than we acknowledge.

One of the best articulations I’ve seen of this comes from a brilliant dude named Bill Conover, who is Director of Spiritual Life at my undergrad, Beloit College.

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An open letter from a white man to a black man in the year 2013

*This is my response to an editorial piece by Questlove, which you can click here to read


If you put the two of us in a room together, we’d make an odd pair.

You, a black man with access to wealth, influence, and places I’ll never go.

I,  a white man with access to goodwill and social capital that no one will ever accord you, regardless of how hard you try.

On the train home from work today, I looked a young black man in the face and we both nodded our heads ever so slightly in the standard greeting of city dwellers. Then I wondered what it would be like to live in his skin, to walk in his shoes.

He was an ordinary looking man, perhaps 25-35 years old, wearing jeans, a shirt, and a sweater. I know nothing about his life, other than that there is a singular characteristic about him that at its core is neither negative nor positive.

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There Are No “Real Men” – The search for a role model, and how I learned to live without one

Pride Weekend

I’m going to tell you a secret.

Since I was young, maybe 8 or 10 years old, I’ve never had a male role model.

To be clear, I did grow up with a father. My parents never split, and while they had their issues – I wondered at times if they should have divorced – for the most part I grew up in a stable environment. I disagreed with my dad (and still do) on plenty of things, but generally we get along and have made our peace on most of the details. Of course, I would do it differently if I had children…perhaps that’s a fairly standard response considering the generational gap (I’m 29, my dad is 72).

But, when I think about men I admired growing up there is an empty space.

Searching for role models

My dad taught me some important things, like the value of hard work & attention to detail, and honesty to a fault. I use those every day, and am grateful. In fact, I wrote an essay in high school about my dad’s blue collar ethic and what I considered to be his everyday heroism, but even then I recognized it was an abstract admiration. I certainly respected and loved my dad but I didn’t want to be anything like him.

So from a young age I went looking for other role models.

At 9 years old I dreamed of being like Michael Jordan and loved watching him compete, but it was hard to escape the fact that he was often arrogant, and at times unkind to others, in pursuit of excellence.

Continue reading There Are No “Real Men” – The search for a role model, and how I learned to live without one

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