My XOXO 2014 talk video and transcript

I don’t do public speaking anymore, but once in awhile I get an opportunity I can’t turn down. XOXO Festival was one of those invitations. Andy Baio, XOXO’s organizer, my former co-worker, and a person who lives so many of the values I hold about the web and making stuff, asked me to tell a personal story on stage there last month. It was one of the scariest things I’ve had to do in a long time.

Here’s the 17-minute video of my talk from XOXO, which happened on September 11-14, 2014, in Portland, OR. If you prefer to read rather than watch, the transcript follows. Do tell me what you think — tweet at me @ginatrapani.

Hi friends. Today I’m going to tell you three stories from my life. That’s it. Nothing fancy. Just three stories.

The first story is about hindsight.

In 2001 I was living in New York City and working at my first dot-com job, at an office on the lower West Side of Manhattan. It was about half a mile north of the Twin Towers, and that’s where I was the morning of September 11th. I stood on the corner of Hudson and Spring Street with my co-workers looking south, and watched the towers burn and fall. This is a photo taken not too far from where we were standing.


We were far enough away that the ash wasn’t falling directly on us but we were close enough to be standing in the path of all the people walking north from the site. All these people in their suits and ties and carrying their high heels, covered in gray ash, not speaking, just walking past us to get uptown, as far away as they could from the wreckage.

A former co-worker of mine showed up. He’d recently gotten a new job at a company whose offices were in the World Trade Center. When he arrived, his hands were shaking. His alarm clock didn’t go off, so he was running late that morning. It saved his life.

Later that day I learned my brother’s childhood best friend died in Tower 2.

As someone in my mid-twenties who’d had a very good life, I’d never experienced anything like that, watching all those people die because they went to work that morning. In the following months and years, the way that I coped with the whole thing was to become obsessed with time — how it was running out, on all of us. Not only that we will all die at some point, because of course we will, but that versions of us die every day. Transformative things happen, and you’re not the same person you were before, just like that. For a long time after 9/11 I found it so difficult to remember what it was like to feel safe — safe in the city I was born and raised in.

To deal with that loss of an earlier version of me, I started future-proofing myself, by voraciously documenting my life, writing about the most mundane things you can think of, taking photos of my garbage cans and my coffee cups, because at any point it could all go away. That’s when blogs were just starting to become a thing, so that’s how I did it — I blogged everything, no matter how inane.

This is what my blog looked like in 2002 or 2003. It’s pretty hard for me to look at it now. circa 2003

A few years in, my fixation on time, and losing it, matured into a worry about wasting time, on things that weren’t important. That I was going to die doing something stupid like upgrading an operating system, or doing dishes, or having to stop at the store to buy milk because I forgot to pick it up when I was at the store the day before.

That’s when this happened.

Original Lifehacker design

Lifehacker is a Gawker blog I started in late 2004 that was about life hacks — clever tricks to save you time and help you run your life more efficiently. It was about systematizing and shortcutting EVERYTHING — from how you spread the butter on your toast in the morning (use a cheese slicer to get the thinnest pats, they melt faster and most evenly) to what Gmail keys help you process your email the fastest (recommend the Y key to archive and the M key, to mute, M is underrated). Lifehacker was about living your most productive, efficient life — and this is the part that didn’t make it into the site’s tagline — because someday you are going to die.

Lifehacker awards and books

The site got popular beyond my wildest dreams, really fast. Million-pageview days weren’t uncommon. It spawned books, and apps, and awards. I got myself on TV, in newspapers and magazines. A family friend heard me on NPR and called my Mom, who asked incredulously “This is because of your… web site?”


Unlike our sibling sites, Lifehacker’s tone was a lot like XOXO — earnest, anti-snark, optimistic. The work my team and I did there is some of the best of my life — and looking back, it came about because I was scared out of my mind that I was running out of time.

It’s such a cliche, really. So often, we see someone’s best work emerge from their worst moments. A pop singer writes a hit song about an awful breakup. A blockbuster film about a tragedy. But a lot of times, it’s NOT that obvious. It takes a really long time to make the connection, in hindsight. It took me over 10 years.

So this is what I try to remember when I’m deep in the muck, and I hope you’ll remember it, too. Somehow, some way, your worst moments feed your best work, and it might well take a decade to see it.

My second story is about transitions.

Years ago my writer friend Michael Barrish published an essay which is no longer on his web site, but it made such an impression on me I’m going to paraphrase it here, hopefully well. In it he proposes that all relationships have a three-part cycle that loops. The three parts are:

A Good Thing, a Rut, Transition

A Good Thing is the honeymoon phase, when things are effortless and everything feels like it’s perfectly right, and this is the best thing that has ever happened. Good Things are by nature fragile, and can’t stay that way forever. Eventually, they turn into a Rut, which isn’t bad, but it is comfortable, and the patterns are well-worn, and there’s not a lot of novelty. Ruts are sticky. They want to keep you there. They’re hard to pull yourself out of. But eventually, a Rut gives way into Transition — if you’re lucky, into a Good Thing.

This cycle of relationships applies not only to friends and romances. I think it applies to work, too.

Even when you have a dream job, like I did, after awhile, you start to coast. The job becomes rote, the process systematized, the learning slows, and you find yourself wondering. For me, it was: If I was spending all my time obsessing about how to save time but had no time left over to do anything else, well, did that make any sense?

My mom always says “A lady knows when it’s time to leave the dance.” Even if you’re scared the dance is the most fun you’ll ever have.


Leaving that job meant I went from having 20 publishing deadlines a day and a traffic chart giving me by-the-minute feedback of how well I was doing, to having zero structure, no goals, and no one to answer to. Many days I sat on my couch, absolutely adrift.

Like many people, I’m most effective when I have my work cut out for me — but cutting out the work, THAT’s the hard part. That’s what’s so difficult about transitions, especially away from perfectly good projects. It’s the uncertainty. You have to drift for awhile, and maybe take some weird detours.

Wave, the book

Transitions are hard. But eventually, if you’re looking and listening, the signposts point to your next Good Thing. That’s what my last story is about.

My last story is about second acts.

I’m still obsessed with time. Not as much losing time, and not as much saving time, but making the time I do spend meaningful. Now I’m focused especially on social networks, because that’s where I spend a big chunk of my time.

ThinkUp time spent insight

It’s not just me; lots of other people have much bigger numbers, and they’re going up. But I’ll be honest: I’m conflicted about how much time we all spend on Twitter and Facebook and Instagram.

Louis CK on social media

On one hand, I think Louis CK is right. We’ve all just given ourselves data entry jobs. And for what? Boredom? Ego? Fear of missing out?

On the other hand, I know how powerful participating on the network can be. These are two of the best moments of my life that were 100 times better because I got to celebrate them on the network.

My best tweets

On social networks I’ve met friends and collaborators and heroes; I’ve had my mind changed and become a clearer thinker; I’ve been heroicized and harassed and then boosted back up again. I know you all have too. So what have been your most meaningful moments online?

Was it Election Night 2008? Was it when Steve Jobs died? Was it when your hero retweeted you? Was it Ferguson?

The time we spend on social networks can be a waste, or it can make us smarter, more connected, more empathetic, and more aware. I just want more of the latter. But how do we get there?

I think the secret is in the data. Twitter and Facebook know my social data is a treasure chest of signals and behaviors and desires and hints about my identity that sometimes I’m not even aware I’m putting out there. I SHOULD be, though, because this is MY data. And these networks have a lot of it.

That’s why I started hacking on an app that mined my Twitter data for answers — answers about how I was spending my time.

To start, I had a bunch of questions.

Who am I spending my time talking to? How often do I say kind words? When do I get sucked into mindless BS?

That weekend hacking project went through several iterations as an open source project, and now it’s available for anyone to try on the web. It’s called ThinkUp and it’s at And it tries its best to answer some of these questions. I’d like to show you some examples of how it does.

This insight tells me how often I thanked someone online in the past month, compared to the month before.

ThinkUp thanks counter insight

This insight tells me whether men or women responded to my Facebook posts the most this month.

ThinkUp gender insight

This insight lets me know when a friend has changed her bio line in her Twitter profile.

ThinkUp bio tracker insight

This insight tells me how much I’m talking about myself online.

ThinkUp first-person counter insight

This insight tells me how many times I dropped the F-bomb online. (Sorry, Mom. I’m really sorry.)

ThinkUp F-bomb counter insight

These are facts that Twitter and Facebook won’t ever reflect back to me. But this is the stuff I want to know! I hope you do too.

And not because you’re a social media douchebag, but because you’re the opposite. As makers, we each build our own platforms where we get to talk to lots of people all at once who like the stuff we make. I’d bet that collectively, in this room, we all have more Twitter followers on average than 95% of Twitter’s users.

That gives all of us outsize privilege and access and clout (with a C) that I hope to be as thoughtful about as I can be.

ThinkUp aspires to help with that. I don’t know how its story ends, but I do want to know: How do you want to spend your time online? How can we make it more meaningful? How do we all use our powers for good (and have fun doing it)?

Thank you for your time today.

If you’ve read this far, then you should sign up for ThinkUp.