Should We

In perhaps our most definitive episode yet, we consider the boy brow trend and traverse the personal histories of our respective eyebrows. Should we do trends? Should we experiment? Should we even bother?

Should Lisa go independent? She should. She did! In this episode, she shares how she knew it was time and what it took to take the leap from day job to free range.

This episode flashes back to just before Lisa became a coach. She looks ahead to her first training and reflects on what brought her around to coaching. From where she stands on her own coaching path, Diana asks, what changed? Find out how our live show, divinity school, and The Voice fit in. You can also flash forward and sign up for coaching right here: shouldwe.co

This episode gets extra real as we reflect on the intermission we took recently. On the other side of a shift, some things just look and feel different. So we pause and ask, should we even take breaks? Do we have to enjoy them? And should we pick everything back up where we left off?

This episode was recorded just before Diana's wedding in June. It captures the whirlwind and the intentions behind an impending change of name and identity. This time we ask, should we change our names? Should we have websites? Should we archive everything? Spoiler alert: Diana got hitched, and you can read about her name change right here if you'd like. https://dianaberlin.com/posts/becoming-berlins

This time we finally go there: to the differences between us (the two of us). We've just discovered them, and we're facing them head-on. That's why this episode is bonus-length. As if that weren't enough, we also define yoga pants vs. leggings (spoiler alert: it's all about context), and discuss the differences between athleisure, dress sweats, and the new *at*-leisure. Welcome to part 2 of season 3. Intermission is over, and it feels good to be back.

Should we record a live show, with a real live audience? We should. We did! We talked about whether we should help ourselves, and what we like to read when we do. In case you missed it—or if being there wasn't enough—now you can listen from wherever you are. You'll also get to meet our emcee, Duretti Hirpa, as well as Katie and Nicole Zhu, the fabulous duo behind Sweet & Sour. Many thanks to Slack for providing the beautiful venue and delicious snacks for this event.

Should we give away other people's money? It's complicated. In this episode, we talk with Kendra Albert about overturning expectations, becoming an activist, and running the Trans Documentation Funding Project. Updates: - We're hiring an editorial assistant. Should it be you? shouldwe.co/news/editorial-assistant - You can become a "true fran" by joining the Love/Hate Club here: patreon.com/shouldwe

Should we be powerful? We already are. This episode unpacks power dynamics underlying everyday actions like taking notes, writing on whiteboards, and practicing empathy. We share our secrets and stories of finding our power and using it. News: - Our first live show is happening this Thursday, May 4th, in San Francisco. Get tickets here: shouldwe.co/live - We're hiring an editorial assistant. Should it be you? shouldwe.co/news/editorial-assistant

Should we write our own job descriptions? This time we swap stories with design manager Heather Phillips about doing just that. We also dig into the intersection of design and venture capital, and weigh the prospect of changing our names.

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?