What I’ve Learned Lately #12

On lasting, working, writing, and hustling

Every now and then, I write a letter about what I’ve learned lately. This was the twelfth one, sent on June 27, 2016.

When Erik and I moved into our apartment in February, we noticed something odd: the blue plastic fobs we raised to unlock our unit’s door never worked on the first try. Hold, thunk, a flash of red; wait a few beats; hold, thunk, a flash of green. In our early days, this seemed problematic. I’d occasionally forget about waiting, and give the handle a few futile twists in-between, feeling brief fury at being barred from my own home. Soon enough, though, we got used to it. Our door had a mind of its own; that was that.

Months later, one of us, distracted, skipped a step and forgot to raise a fob at all. To our joint surprise and, shortly, concern, the door opened smoothly. We stepped back out; performed some tests. We couldn’t believe our eyes. Worried, one of us sent a note to the building manager, trying to be firm but understanding. We just discovered that our door doesn’t lock on its own, was the gist. As you can imagine, this is a major security concern. We hope to find a solution soon.

Later that day, I saw the building manager in the lobby. Kindly, he asked: does it ever turn red when you raise the fob? Yes, I replied — right before we go in! And then it hit me:

The door had never been locked.

For a good four months, our door had been perpetually open. Perpetually, that is, except for the few beats between red and green each time we entered. We were locking ourselves out, then letting ourselves in. And the whole time, we felt safe. We were safe. We were fine.

We lock the door now, but I haven’t let go of the story. What could it mean?


Gravity seeps into the things that stick around. I wrote that once and think of it often. It’s a powerful sentence because it helps me see through to the other side of novelty. I love newness, but I’m also attracted to durability. As someone who wakes up most mornings with a warm inkling that everything might be different and better from then on, I’m especially interested in transformations that pull their weight. Things that last.

In that spirit, here are some habits and preferences I’ve kept around for a year or more:

I still read and write every day before checking the internet. Every morning, I read for at least five minutes (I set a timer) and journal (at least 750 words) before glancing at notifications or digging into email. I originally intended the five minutes of reading to be a daily gateway drug, but alas, boxing it in seems to have had the opposite effect; I’m thinking now about how to correct for that. The journaling, though, has been huge for me.

I still feel best when I wake up early. But I definitely don’t do it every day. (For a while last year, I was on the 5am train.)

I still rely on OmniFocus for managing my personal to-dos. Reading Creating Flow with OmniFocus helped me understand the application inside and out, which made it possible for me to commit to it for the long haul. I now see it as a set of knobs and levers arranged in support of my own goals and self-knowledge, rather than a mysterious, monolithic system. I’m particularly enamored with OmniFocus’s strong support for universal capture of stray intentions — through a firm press of the iOS app icon, through a keyboard shortcut on my laptop, through photographs of Post-It notes captured in meetings, and through a dedicated email address I can forward things into. If your stomach for elaborate systems is strong, I recommend checking it out.

I still pay for, and treasure, SaneBox. SaneBox uses machine learning to figure out the emails I would have archived anyway, then preemptively archives them for me. It’s aggressive and impressively right. Having SaneBox in my life reduces microscopic decision fatigue by a lot.

I still swear by Paige jeans and Ten Points shoes. I love well-designed basics, and these fit the bill.

I still wear my Apple Watch regularly. Not every day, but nine days out of ten. I use it mainly as a notifications channel and to check the time and set timers, but I appreciate its fitness features on the occasions when I do break a sweat, and I remain pleased with theOmniFocus complication. I’m curious to see whether watchOS 3 brings me back into the watch apps fold.

For every habit that lasts, one bites the dust. In the past year, I stopped reading Twitter cover to cover every day; I stopped using Evernote; I stopped visiting Tumblr, ever; Istopped avoiding caffeine; I stopped using Headspace, a meditation app — I liked it, but Ifound that I like free-form writing more. I miss the intense hope I felt at the start of bringing each of those tools into my life, but it’s more important to me to question everything.


I’ve held jobs at companies large and small, but being a product manager at a 40-person startup is something else. At Quip, I work with one designer, many engineers, a marketing team, and a stellar sales and operations crew. Anything not firmly situated in one of those domains is entirely likely to get done by me or Nate, Quip’s other full-time PM. Over the course of any given week, I end up doing some combination of wireframing, producing quantitative analyses, conducting customer interviews, copywriting, getting out of the office to work with partners, facilitating meetings, and drafting product plans. To wrap my arms around this variety pack of tasks, I applied the “what I’ve learned lately” lens to a workplace context and started keeping a running Quip doc called “This Week I Learned(TWIL)…” In “Write About What You’ve Learned Lately,” a piece I published during my first month on the job, I reflected on the practice and shared some bullet points I’d captured along the way. Five months further along, here are some more souvenirs from my variety pack of experiences:

  • There exists a list of hex values for every Crayola crayon every made.
  • For more minimal browser screenshots, it’s possible to streamline Safari’s toolbar by removing everything inessential. Go to View > Customize Toolbar and drag off elements from there.
  • To get an interpunct (“·”), type Opt-Shift-9 on a Mac. Or, just visithttp://middot.net/ and copy-paste.
  • For quantitative analyses, Wagon is hard to beat.
  • Apple runs an “engineering capture” program to turn broken devices into hardware cadavers. Then, they send you a brand-new one. This was the fate of my first golden MacBook.
  • Slack’s standard typeface is Lato, which happens to be in Google’s font set. Because of this, it’s possible to make surprisingly-realistic wireframes of Slack’s interface in Google Slides. (Learned while wireframing Quip’s Slack integration, which launched in May.)


The other day, a friend sent me a note on Instagram. “How are you?” “I’m good,” I replied — “working on becoming prolific.” “Prolific sounds hard,” she shot back. And you know, she’s not wrong!

Like many writers, I maintain a large and ever-growing set of conditions I see as absolute prerequisites to doing anything that resembles putting words to a page. I need to be well-slept, well-hydrated, well-fed; I need to have caught up on the entire internet, ideally within the last 45 minutes; I need to be wearing my softest clothes; the windows need to be open if they’re closed, and closed if they’re open. Becoming prolific is about casting prerequisites aside and recognizing that serendipity is the part of writing in public that means the most to me, and serendipity increases with surface area. So, surface area is what I’m aiming for. Here are three pieces I’ve come up with as a result:

  • The Felt Internet,” my review of Virginia Heffernan’s brand-new book, Magic and Loss: The Internet as Art. “Heffernan’s accounts of picking up a Kindle, slipping into a fugue state induced by following endless links, or thumbing an iPod wheel didn’t just resonate with my experiences; they were my experiences. Reading Magic and Loss made my memories of the internet new again.”
  • Pragmatic Shopping,” a detailed account of how I learned to love (or, at least, not hate) figuring out what to buy. “My objective function for shopping looks something like this: Time + Money + Conflict − Anticipation ≤ Solution + Feeling − Problem. If shopping’s inputs are time, money, conflict, and anticipation, and its outputs are solutions, feelings, and more problems, my goal is to get more out of the experience than I put in.”
  • Should We Spill the Beans,” a playful piece Lisa and I wrote about how we made the first season of our podcast, Should We, on a budget of zero.


My first thought was to title this section “Hoping” — as in, “I’m really hoping our Kickstarter project for the second season of Should We makes it!” But the truth is, I’m not hoping — I’m hustling. When Lisa and I decided to set our sights on $10k instead of $1k, the stakes got a lot higher, and the outcome a lot less certain. Inching toward that goal has demanded daily effort. But because Should We itself is structured as an ode to everything I care about most — reading, writing, inquiry, self-awareness, storytelling, laughter, and friendship — working hard on it turns out not to be hard at all. This is the beauty of a project that fits. I see it, now.

Still. With 35 hours and $1,855 (now, 22 hours and $1,249!) to go, we can’t do it alone. Even if you’re not a podcast listener — even if you never listen to podcasts at all, and figure you never will — I hope you’ll consider pledging toward one of the many rewards related to adjacent domains. $1 will get you access to a list of our all-time favorite books; $75 will get you actual advice; $200 will get you a productivity makeover. Lisa and I designed the rewards around everything we love doing, so truly: I can’t wait to get started. Not to mention, season 2 is going to be our best work yet.

Help us get down to work on season 2 by backing Should We Actually Try on Kickstarter. The campaign ends tomorrow — Tuesday, June 28, at 8pm PDT — so time is short and our hopes are running high. Thank you, again, from the depths of my sunburnt heart.

Until soon, and always —

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