A project that means a lot to me, some things I’ve written, and some books I loved

Every now and then, I take some time to reflect on what I’ve learned lately, in letter form. This was a special edition, sent June 6, 2016. If you’d like, you can read the first eleven on Medium and subcribe at expertnovice.com.

To all new readers: welcome! My name is Diana Kimball, and at the start of the year, I moved back to San Francisco to join a startup called Quip after two and a half years at SoundCloud in Berlin.

Trying

Last week, I launched a project that means a lot to me: Should We Actually Try, a Kickstarter campaign to fund the second season of Should We, a conversation between friends in podcast form. In every episode of Should We, Lisa and I ask and answer questions that work to turn expectations inside out. For example, should we subscribe to things? Should we move to the Nordic region? And how old should we be? It’s playful and real and deep, and the first twelve episodes were a joy to make.

For season 2, we decided to go big. Lisa and I are raising $10,000 to fund professional production and a visual identity, with producers and designers whose work we adore.

Three things you could do to make my day:

1. Back Should We Actually Try on Kickstarter. The friendship bracelets sold out, but there are lots of other rewards left, including two new reading-themed rewards we introduced today: “Should We Be Book Doctors” (we’ll write you a set of personalized book recommendations) and “Should We Read All Day” (you pick the book, we’ll both spend the day reading and responding to it). And everyone who backs gets access to our secret playlist of podcast extras, starting with some breathless reflections I recorded recently after a modern dance class. (Dance is something new for me.)
2. Share “Should We Spill the Beans,” an in-depth look at how we produced season 1. Lots of iPhone apps were involved.
3. Subscribe to Should We on iTunes, on Overcast, or sample it on SoundCloud.

Despite my long history with Kickstarter — including an early blog post about the platform, a summer spent writing case studies there, and a small project to publish a personal archive in zine form — this is the first time I’m experiencing the suspense and slow-burn hope of a project this big. It means a lot to me because developing a creative process with someone I trust to the end of the world, and then asking for help to make that creative process even more spacious, is challenging a lot of my unspoken beliefs about creativity — namely, that it has to be hard and lonely. Making Should We is the opposite of hard and lonely, and I’d love nothing more than to take it to the next level. Thank you for considering being a part of it.

Writing

Here are some of my favorite things I’ve published since sending my last newsletter:

• “Save for Later” — a longread on bookmarking apps (like Pinterest) and what I call “the wish economy.”
• “Close at Hand” — another longread, this one a whirlwind tour through the history of pocket-sized technology.
• “My Berlin” — a list of my favorites, sorted into Shops, Apps, Smoothies, Cafés, Restaurants, Movement, Experiences, and Resources. For those who know me, smoothies getting their own category will not be a surprise.
• “Go on a Readtreat” — a guide to planning your own reading retreat, one of the simplest good things I’ve ever done.
• “Write About What You’ve Learned Lately,” a piece about a practice I adopted at my new job that I can recommend to anyone.

Since Medium launched their next generation of publishing tools earlier this year, and recently went even further, I’ve found myself publishing more and more of my writing there. You can set your own domain; define your own URLs; even choose a publication color that becomes the color people see when they highlight your writing! It’s spectacular. If you haven’t yet taken Medium for a spin, I highly recommend it. I’d love to read what you write, once you do.

Reading

No newsletter would be complete without some book recommendations — even a newsletter where I’m mainly asking for your support. :) At the end of last year, I wrote up the books I read in 2015. Out of all of them, my favorites were The Power of Glamour, by Virginia Postrel, The Folded Clock, by Heidi Julavits, and H is for Hawk, by Helen Macdonald. So far this year, the front-runners are Truth & Beauty, by Ann Patchett, The Beautiful Bureaucrat, by Helen Phillips, and Magic and Loss: The Internet as Art, by Virginia Heffernan — out Tuesday, June 7! I’m also always looking for new book recommendations, so if you’ve got any in mind, please do reply.

Thank you for reading, and for all the ways you’ve supported me over the years. This is the big one. I hope we make it!

fingers crossed, imagination on overdrive —
Diana