Should We

Should we listen, to ourselves and others? Of course we should, but how? In this episode, Diana talks with our friend Luisa about the practices that help them listen closely, see things differently, make decisions, and sometimes even make new friends.

Listen in on this conversation across continents, between friends, in San Francisco and Berlin.

Should we pay attention? Should we move away, or stay put? Should we craft the stories we tell? How should we define honest communication? And what should we do with our rage?

These are just a few of the questions we weigh in this conversation across continents with our dear friend Luisa.

Season 3 kicks off with one big question: should we change? The two of us dig deep, reflecting on how we've been changed and how we've changed ourselves on purpose.

Listen in to hear our evolving perspectives on TV, politics, tenderness, personal training, transparency, and consistency.

Well, friends: we made it. To mark the end of season 2, we question the wisdom of plans and make a few more. We'll be back in a few weeks to kick off a whole new season of conversations with friends about the everyday choices that make us.

Want to pitch in? Now that we've got Should We down to a science, we're ready to play for keeps. Join us on Patreon to support us in telling more secrets and taking more risks: https://www.patreon.com/shouldwe

We're marching, we're standing up. What's next? How about breakfast?

In this episode, you'll meet Diana's advisory board: senior engineers Duretti Hirpa and Rachel Myers. The three share their breakfast-based rituals for advice, accountability, and lifting each other up.

This unedited special episode is a recording of our pre-inauguration vigil. It begins and ends with poetry. In between, we muster our strength to say what we really mean. Should we stand up? We will.

Meet Virginia Heffernan—author, bookworm, and true-blue internet friend. Her 2016 book, Magic and Loss: The Internet as Art, captivated us; this conversation takes our favorite threads from the book and runs with them. Listen in to hear Virginia turn the tables on us and help us figure out where friends come from.

In this episode, we talk message boards, Medium, and the metric system. Press play when you’re in the mood to get to the bottom of the internet, once and for all.

Meet Jennifer Brook, lead design researcher at Dropbox. Having once sold (almost) everything and lived everywhere, she helps us answer: should we own things? Listen in to find out what the three of us have kept in the midst of international moves.

In this episode, we also talk about optimizing for a joyful commute and developing creative practices, such as sketchbook-making and silent disco.

We're kicking off the year just like old times: two friends and three questions. Should we get moving? Should we take breaks from habits? And should we buy silk outerwear?

In this episode, we weigh the pros and cons of gyms, breaks, and impractical garments. Take a listen as you finalize your resolutions.

Meet Erin McKean, founder of Wordnik, bestselling author, and former editor-in-chief of American Dictionaries for Oxford University Press. She and Lisa discussed all the questions: should we wear dresses, should we be founders, should we write books, and should we be nice?