Diana Kimball

Diana lives in Berlin and works at SoundCloud. Before Berlin, she lived in Boston and studied at Harvard Business School. Before Boston, she lived in San Francisco and started book clubs. Before San Francisco, she lived in Cambridge and haunted Harvard's libraries. Before Cambridge, she grew up in Ann Arbor, where she had a newspaper route for five years.

You can find Diana on Twitter, on her blog, in your inbox, or very occasionally racing to finish a book with 24-Hour Bookclub.

Published Thoughts

Recently, I read a book about tidying up. The book's author, Marie Kondo, implores readers to hold every object in their lives in their hands, one after another, and part ways with any that don't spark a "thrill of joy." Kondo acknowledges that there will be friction along the way, but insists that "when we really delve into the reasons why we can't let something go, there are only two: an attachment to the past or a fear for the future." Either resistance can be overcome:

When you come across something that you cannot part with, think carefully about its true purpose in your life. You'll be surprised at how many of the things you possess have already fulfilled their role. By acknowledging their contribution and letting them go with gratitude, you will be able to truly put the things you own, and your life, in order. In the end, all that will remain are the things that you truly treasure.

Here, at the end of a year spent trying to move past forever projects, Kondo's message hit home. This is what I need to do next: hold every project, every object, every belief in my hands—one after another—and ask, does this stand for joy, obligation, or fear? And if it's time to let go, I will.

You Are Listening To

If you tend to walk around worrying, you might find that piping stories into your ears helps you to get out of your head. I know it’s helped me. Podcasts are the perfect antidote to tired internal monologues, and this is their golden age. Here are a few of my favorites:
  • This American Life: of course. They’ve still got it.
  • Serial: better than television. From the people behind This American Life.
  • The Broad Experience: short, ingenious interviews with experts on women, success, and the workplace.
  • StartUp: “a series about what happens when someone who knows nothing about business starts one.” Shockingly, splendidly honest.
  • Pop Culture Happy Hour: Smart, lively conversations about what you should be reading, watching, and listening to. I follow up on at least one recommendation per episode.
  • 99% Invisible: jewel-like stories about design and the art of noticing. Pitch: a 99% Invisible-style podcast about sonic culture.
  • Strangers: true stories, told simply.
Stream them on SoundCloud or subscribe through Overcast. See if they change your mind.

Habits vs. Stunts

Habits are hard; stunts are fun. It’s easier to do something for 24 hours straight than it is to do that same thing for one hour every weekday for a month.

If you’re itching for a spike of novelty, commit a whole day to a new pursuit and see what happens. I learned this lesson from hackathons and put it into practice with 24-Hour Bookclub, a reading flashmob that convenes on Twitter every now and then to read a book in a day.

Committing to a new habit feels revolutionary on day one, burdensome on day two. Committing to a day-long stunt feels like mischief all the way through. If transformation is what you’re after, think first on the scale of days, not weeks. Trust yourself to start and finish tomorrow, rather than expecting yourself to be perfect from now on.

A Surefire Way to Make Someone's Day

Visit any site where people share their work—Kickstarter for creative projects of all kinds, SoundCloud for music and audio, Vimeo for video, Dribbble for design—the list goes on. Next, fall down the rabbit hole. Keep clicking until you find something that stuns you, made by someone who seems like they’re just starting out. Then, post about the project publicly, with a note about what struck you. Include the person’s handle so that they’ll see it, too.

At the very least, the person will smile. At best, you’ll give someone their big break. The approbation of strangers is holy; never underestimate how much yours could mean.

I shared the story of my own big break and what it meant to me in a talk I gave last year.

To solve for the other side of the equation—making yourself yourself findable in the first place—I recommend Austin Kleon’s new book, Show Your Work!

No More Forever Projects

It took me a long time to see past forever projects.

I told myself that making promises gave beginnings gravity. I labeled my newsletter a “lifelong project” not long after I started it. I called /mentoring a “movement” the day I announced it. Commitment marked a project as something worth talking about, I thought. This was how I would give my ideas escape velocity.

Escape velocity came, but at a cost. No amount of attention could spur perpetual motion. Once I’d set every expectation of permanence, disappointment loomed and glowered; inevitable.

Eventually, I started asking myself: why am I promising permanence? The answer crept up on me: because permanence is better than nothing. Without the momentum of obligation, I didn’t trust myself to begin anything in earnest.

The thing is, it never worked. The half-life of obligation is short; the half-life of guilt is long. Promises never saved one of my side projects, but they clogged many nights and weekends with the gunk of regret. Something had to change.

My friend Jamie Wilkinson once told me about a decision he’d made. No more forever projects, he said. From now on, every project is one-time-only. Treat beginnings like endings: celebrate them, document them, let someone else pick up where you leave off. If the project’s worth repeating, there’s nothing to say you can’t still be the standard-bearer. But at least it’s a choice. By ending well, you give yourself the freedom to begin again.

These days, all my projects start as experiments. No forceful promises, no forever projects. Gravity seeps into the things that stick around.