What I’m learning about public speaking

A letter sent to all newsletter subscribers the morning of November 8, 2017.

I should be asleep. Instead, I faded awake at 3:45am, mind already lurching toward the day ahead. This afternoon, I’m speaking to a room that seats 5,000, as part of Quip’s keynote at Dreamforce.

The fantasy of a big break, combined with my fierce care for everything we built and everyone who built it, has made this keynote feel nearly as tender as my wedding. I’ve felt every way about it: the vise grip of internal pressure, the swirling winds of external expectations, the steady support and deep belief of my teammates, so sure that I can do this; here, I’m starting to cry. The soaring hope of wondering if this could be my big break, the self-judgment of “what even is a big break, and why do you think you’re so special,” the dismay of seeing bags under my eyes this morning. The relief that I planned hair and makeup at places I trust. The dread that my burgundy dress will be wrinkled. The visualization, on loop, of walking up the steps to the cloud-shaped stage in high heels, which I hardly ever wear—will I make it? The nagging worry that I’m jinxing this by telling you it matters to me before it’s over.

Yesterday, I told a lot of people that this mattered to me, and more or less told them I was nervous. I didn’t say I was nervous, because I didn’t want anyone to worry about me. (“You can’t control what other people think” echoes through my brain—I know, I know.) I tweeted: “I’m speaking on the biggest stage of my life tomorrow, and I could use some good vibes! Got any stories of small ways I’ve changed your [world emoji]?” I sent the tweet on a desperate whim right before I’d planned to drift off to sleep, imagining that warm stories would flood in as I power-napped, and that there would be an avalanche once I gently woke. Not so! Instead: what felt like crickets on Twitter, and an inconveniently pounding heart.

Realizing that a nap was off the table, I messaged my friend Edmond. (He and Lisa are two of my sturdiest shame-busters, but it only works if I tell them everything.) “So I had the idea to seek support publicly, and it’s been interesting so far. Observations: 1) I may not have asked for help directly enough 2) My fears of being pitied, ignored, or delusional are all being activated… 3) I wanted to do this to psych myself up, but now my heart is pounding in a not-so-good-feeling way.” And a few minutes later: “I think Ignored, Pitied, and Delusional are for sure saboteurs. They come up when I make each moment / every day a crucible where I need to prove myself anew. Like ‘Now is when I’ll find out what they really think.’ And whatever they think now, is the last thing they’ll think, and fully true. Ido know I’ve changed people’s lives. And yet the only thing I make matter is whether I hear about it TODAY.”

Crickets, then dribs and drabs; a slow build; and by the end of the day, over twenty responses. People I’ve known for years, people I’ve never spoken to except through this newsletter and the podcast I make with Lisa. People reflecting back to me everything I strive for in words I’ve never used—words better than any I would have claimed. Carrie saying “your letters + @shouldwepodcast have taught me to approach all of my projects with a lethal combo of rigor and lightness!” Jon saying “I think you're the reason I became a PM!” Beth saying “Your podcast helped me think about how to improve myself and my life, and it got me started on cleaning out and curating my clothes! It also gave me a lot of laughs on my hour long commute :)” Michele saying “the first time i saw you speak at a tiny little event in berlin i felt inspired and invigorated that i was making the right life choices!”

I got exactly what I needed, exactly what I’d asked for—exactly what I’d instantly regretted wanting. And I wanted to share that with you from here. On the other side, this could all seem obvious, or worse. But right now, I’m wide awake.

Diana Berlin