Should We

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Creative conversations about the everyday choices that make us, hosted by Lisa Sanchez and Diana Kimball Berlin.

Diana Berlin & Lisa Sanchez


    • Sep 28, 2021 LATEST EPISODE
    • monthly NEW EPISODES
    • 37m AVG DURATION
    • 60 EPISODES


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    Latest episodes from Should We

    No. 59 — Have Hobbies?

    Play Episode Listen Later Sep 28, 2021 42:36


    In this episode, Lisa reflects on beginning crochet, and Diana shares her own journey with LEGO. We let go of self-limiting assumptions and productivity, replacing it with simple enjoyment. Lisa's crochet role model: - Instagram: https://www.instagram.com/debrosse_nyc/ - Modern Crochet book: https://debrosse.com/products/moderncrochet Lisa's course on intuition: https://www.winging-it.net/

    No. 58 — Step Out?

    Play Episode Listen Later Jul 27, 2021 50:28


    After many months of laying low, some of us are stepping out, tentatively, and finding it isn't easy. In this episode, we talk about the burnout, overwhelm, and self-consciousness many are facing. Then we dip into each of our style and wardrobe journeys as we dress our current bodies for this season of life. - Laurel Kinney, personal stylist: https://laurelkinney.com/ - Laurel's course: https://www.styleshiftworkshop.com/ - Lisa's course: https://www.winging-it.net/

    No. 57 — Be Productive?

    Play Episode Listen Later Jul 1, 2021 55:34


    Should we be productive? In this episode, we unpack "macho productivity," debunk productivity myths, and share how we actually get things done. - Lisa's audio course on intuition: www.winging-it.net/ - Email Diana: diana@matrixpartners.com

    No. 56 — Be Back?

    Play Episode Listen Later Jun 15, 2021 54:22


    Should we be back? We should! We are! Tune in for our stories of pandemic pregnancy, pandemic childbirth, and Diana's new job in venture capital. - Check out Lisa's audio course on intuition: https://www.winging-it.net/ - Read about Diana's decision to join Matrix: https://dianaberlin.com/posts/2021/1/28/whether-when-and-where - Email Diana: diana@matrixpartners.com

    No. 55 — Build Wealth?

    Play Episode Listen Later Oct 26, 2020 45:34


    A conversation with Deanna Dong, VP of Marketing at Wealthfront, on what it means to build wealth. Should we invest? Should we take time off? Should we touch every dream? We discuss the risks, benefits, and tradeoffs of big life and career decisions.

    No. 54 — Eat Our Stockpile?

    Play Episode Listen Later Mar 13, 2020 46:51


    Today we checked up on each other, traded tips for hunkering down, and tried on different perspectives. We laughed our heads off while recording this episode, and we hope you will too. - Going Through It podcast with Rebecca Traister: https://mailchimp.com/presents/podcast/going-through-it/rebecca-traister - Safe Catch: https://safecatch.com/

    No. 53 — Seek Glamour?

    Play Episode Listen Later Mar 4, 2020 44:30


    What is glamour, anyway? And why does it seduce us so? In this episode, we look behind the scenes of our most glamorous moments so far and even venture back to memories of perusing catalogues as kids. - The Power of Glamour by Virginia Postrel: https://www.amazon.com/dp/B00A25EZ72 - “Who Would Tavi Gevinson Be Without Instagram?” https://www.thecut.com/2019/09/who-would-tavi-gevinson-be-without-instagram.html - “The Grooming Gap“ https://inthesetimes.com/article/22197/grooming-gap-women-economics-wage-gender-sexism-make-up-styling-dress-code - Cocoon (Coaching with Lisa): the-cocoon.co

    No. 52 — Report Harassment?

    Play Episode Listen Later Feb 17, 2020 45:52


    This episode unpacks the nuances of a choice too many people have to make. In conversation with Jessica Collier, CEO of Spot and Cofounder of All Turtles, we share personal experience, new research, and essential recommendations for responding to and preventing workplace harassment and discrimination. - Spot: talktospot.com - All Turtles: all-turtles.com - Cocoon: the-cocoon.co

    No. 51 — Perform Self-Care?

    Play Episode Listen Later Feb 2, 2020 37:47


    When does self-care—and especially, performing it for others—become a burden? In this episode, we unpack the difference between “self-care” and actually taking care of yourself. Related Links: * Cocoon (Coaching with Lisa) https://the-cocoon.co/ * How to Do Nothing by Jenny Odell https://www.amazon.com/dp/B07FLNFRGK * Workin' Moms (Netflix) https://www.netflix.com/title/80198991?s=i&trkid=13747225 * What Everyone Can Learn From Parents of Big Families (NYT) https://parenting.nytimes.com/health/big-family? * Saying ‘No’ Is Self-Care for Parents (NYT) https://parenting.nytimes.com/health/burnout-boundaries * Natalie MacMaster, Cape Breton fiddler https://www.ted.com/talks/natalie_macmaster_fiddling_in_reel_time? * Do Less by Kate Northrup (not recommended) https://www.amazon.com/dp/B07FC5JHX1/ Further Reading: * Who Would Tavi Gevinson Be Without Instagram? (The Cut) https://www.thecut.com/2019/09/who-would-tavi-gevinson-be-without-instagram.html * The Little Book of Hygge by Meik Wiking https://www.amazon.com/dp/B01GONJFZ2

    No. 50 — Put a Pin in It?

    Play Episode Listen Later Nov 18, 2018 7:47


    This mini episode marks the close of Season 4 and the celebration of quite a milestone: 50! As we head into a purposeful, open-ended pause, we reflect on how much fun it is to make this podcast and share it with you. Plus, a life update: Since recording this episode, Diana's beautiful baby boy was born! Mama and baby are happy, healthy, and brimming with love.

    No. 49 — Shift Gears?

    Play Episode Listen Later Nov 4, 2018 37:41


    Each of us shares our reflections on the threshold of new chapters. We talk about maternity leave, negotiating offers, and Cocoon, the newest evolution of Lisa's coaching practice. Take a peek at https://the-cocoon.co Cocoon empowers underrepresented leaders to carve bold, beautiful paths toward the fuller lives, fulfilling work, and better world they imagine. And Cocoon Collective is the advisory board of your dreams. As a member of this small, inclusive group, you’ll get to draw from its collective wisdom and expertise. Related links - Sweet & Sour podcast: sweetandsour.fm - Headspace: www.headspace.com

    No. 48 — Give and Take?

    Play Episode Listen Later Oct 21, 2018 43:01


    In this episode, we talk secondhand clothing and firsthand experiences with philanthropy and empathy. What does it mean to be good at receiving, and what are the pitfalls of trying too hard to be a good person? Related Links: · Darling Magazine, Selfless Issue, “Shopless”: https://shop.darlingmagazine.org/collections/frontpage/products/issue-24-selfless?variant=8687614197856 · Thredup: http://www.thredup.com/r/TFFZO8 · Rent the Runway: https://rtr.app.link/e/AYR8Cx2r5P · Give and Take, by Adam Grant: https://amzn.to/2x50ufR · Global Fund for Women: https://www.globalfundforwomen.org/ · ScholarMatch: https://scholarmatch.org/ · 826michigan: https://www.826michigan.org/ · 826 Valencia: https://826valencia.org/ · The Particular Sadness of Lemon Cake, by Aimee Bender: https://amzn.to/2CDwoVJ · Austin Kleon: https://austinkleon.com/

    No. 47 — Be Seen?

    Play Episode Listen Later Oct 16, 2018 38:32


    This episode goes behind the scenes on what it means to see ourselves in new ways, in photographs and on stage. · Helena Price: https://www.dagmarstudios.com/ · Melanie Riccardi: http://www.melaniericcardi.com/ · Oprah dancing at a photoshoot: https://www.instagram.com/p/Bd8z4MTBnba/ · Ellen Chisa: https://www.ellenchisa.com/ · Tippi sweater at J. Crew: https://www.jcrew.com/p/womens_category/sweaters/pullover/tippi-sweater/E1277 · The confidence-competence connection: https://lauravanderkam.com/2013/05/confidence-competence/ · Diana’s 2017 newsletter about speaking in a keynote: https://dianaberlin.com/letter/public-speaking

    No. 46 — Be Friends?

    Play Episode Listen Later Sep 9, 2018 37:09


    This episode celebrates the inner workings of our friendship—the structures, previously unspoken parameters, and communication channels that keep making it work.

    No. 45 — Have Stress?

    Play Episode Listen Later Aug 26, 2018 29:03


    From the midst of some honest-to-goodness stress, we dig into nuanced perspectives on the thing itself. Should we have it? We do. Is that good or bad? It's complicated. You might be surprised by what we have to say. Find show notes and links at shouldwe.co

    No. 44 — Be Ambitious?

    Play Episode Listen Later Aug 6, 2018 52:53


    In this special edition, we answer listener questions about ambition: Should we lean in? Should we leave? Should we manage up? We share our own stories about the choices and challenges that brought us to where we are today.

    No. 43 — Invest?

    Play Episode Listen Later Jul 22, 2018 32:29


    If you can wear it, is it an investment? We unpack this and other burning questions in an episode chock full of financial resources and revelations.

    No. 42 — Have Kids?

    Play Episode Listen Later Jul 8, 2018 37:12


    We're back with a new episode, new season, and NEWS. Listen in as we unpack one of our biggest questions yet.

    No. 41 — Change Everything?

    Play Episode Listen Later Dec 11, 2017 53:15


    In the season finale, we dig into the tension between ritual and change. We share how much has changed for each of us—even since the last episode—and how our habits evolve.

    No. 40 — Budget?

    Play Episode Listen Later Nov 27, 2017 34:23


    Should we talk about money? This episode is a peek under the hood of our business. We also unpack the personal experiences that influence each of our perspectives on risk, investment, and budgeting.

    No. 39 — Do Boy Brow?

    Play Episode Listen Later Nov 13, 2017 27:49


    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?

    No. 38 - Be Independent?

    Play Episode Listen Later Oct 30, 2017 28:14


    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.

    No. 37 — Change Our Minds?

    Play Episode Listen Later Oct 18, 2017 42:27


    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

    No. 36 — Take Breaks?

    Play Episode Listen Later Oct 1, 2017 32:21


    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?

    No. 35 — Get Married?

    Play Episode Listen Later Sep 18, 2017 19:29


    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

    No. 34 — Be Different?

    Play Episode Listen Later Sep 4, 2017 43:47


    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.

    No. 33 — Help Ourselves? (Live Show)

    Play Episode Listen Later Jun 5, 2017 45:49


    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.

    No. 32 — Give Away Other People's Money?

    Play Episode Listen Later May 17, 2017 49:02


    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

    money giveaway kendra albert
    No. 31 — Be Powerful?

    Play Episode Listen Later May 1, 2017 55:22


    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

    No. 30 — Write Our Own Job Descriptions?

    Play Episode Listen Later Apr 19, 2017 35:58


    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.

    No. 29 — Listen?

    Play Episode Listen Later Apr 2, 2017 30:57


    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.

    No. 28 — Pay Attention?

    Play Episode Listen Later Mar 21, 2017 27:14


    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.

    No. 27 — Change?

    Play Episode Listen Later Mar 5, 2017 36:29


    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.

    No. 26 — Make Plans?

    Play Episode Listen Later Feb 5, 2017 32:13


    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

    No. 25 — Do Breakfast?

    Play Episode Listen Later Jan 22, 2017 33:03


    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.

    No. 24 — STAND UP (Special Edition)

    Play Episode Listen Later Jan 20, 2017 32:56


    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.

    No. 23 — Make (Internet) Friends?

    Play Episode Listen Later Jan 15, 2017 37:07


    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.

    No. 22 — Own Things?

    Play Episode Listen Later Jan 8, 2017 26:22


    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.

    No. 21 — Get Moving?

    Play Episode Listen Later Jan 1, 2017 28:04


    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.

    No. 20 — Be Nice?

    Play Episode Listen Later Dec 18, 2016 30:52


    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?

    No. 19 — Ask Questions?

    Play Episode Listen Later Dec 11, 2016 33:14


    Lisa asks Diana all about her first step in becoming a coach. We cover questions like, “should we ask questions,” and “if so, what kind?” It's a follow-up to last week's episode, in which we asked Jane Tight, “should we become coaches?”

    No. 18 — Become Coaches?

    Play Episode Listen Later Dec 4, 2016 31:57


    Meet Jane Tight, leadership coach, co-founder of SeeChange Partners, mother of four, spouse of 30 years, world traveler, and chicken owner. Jane sheds her wisdom on questions like should we become coaches, should we ask for help, should we go on silent retreats, and should we go on silent retreats with friends.

    No. 17 — Give Advice?

    Play Episode Listen Later Nov 27, 2016 30:57


    In this episode, Diana talks with Cate Huston, engineering leader, world traveler, writer, and co-creator of Technically Speaking. They cover questions like should we blog, should we send newsletters, and should we give advice.

    No. 16 — Make Food?

    Play Episode Listen Later Nov 20, 2016 36:54


    Our second first episode of season two* is a conversation with Cynthia Samanian. Cynthia is the creator of Confetti Kitchen, a cooking site for ambitious beginners. For this episode, we met her in the kitchen and the studio to suss out: should we ride Vespas? Should we start businesses? And the big one: should we make food? * We originally planned for this to be the very first episode of season two, but history intervened and we made the choice to launch last week’s episode first instead. Now you get both!

    No. 15 — Work Together?

    Play Episode Listen Later Nov 13, 2016 39:31


    Welcome (back!) to Season 2 of Should We—a conversation with friends about the everyday choices that make us. In this episode, meet Celeste Prevost and Rob Angermuller of Math Times Joy, who designed our new identity. Listen in to hear about their work together, our work together with them, and the work we have to do together as citizens. Should we work together? Definitely yes. https://shouldwe.co

    No. 14 — Finish Strong?

    Play Episode Listen Later Jun 26, 2016 23:32


    In this final coda to season 1 of Should We, we introduce our producers and talk shop about season 2. Like what you hear? We’d love your support on our Kickstarter project, which runs through June 28, 2016, at 8pm PDT: https://www.kickstarter.com/projects/dianakimball/should-we-actually-try A giant thank you to everyone who’s pitched in already. If this comes true, it will be because of you.

    No. 13 — Keep Going?

    Play Episode Listen Later Jun 19, 2016 41:00


    In this bonus episode, we discuss the progress of our Kickstarter campaign to fund season 2, the perennial dilemma of whether and when to speak up, and the major pros and minor risks of rose gold devices. Want to move us closer to making season 2 a reality? You know what to do: https://www.kickstarter.com/projects/dianakimball/should-we-actually-try

    No. 12 — Actually Try?

    Play Episode Listen Later May 31, 2016 34:58


    In our final episode of season 1, we make an enormous decision about our Kickstarter campaign, which launches today. Should you back it? We hope you do. https://www.kickstarter.com/projects/dianakimball/should-we-actually-try

    No. 11 — What Should We Buy Online?

    Play Episode Listen Later May 16, 2016 39:06


    No. 11 — What Should We Buy Online? by Diana Berlin & Lisa Sanchez

    No. 10 — Take Vacations?

    Play Episode Listen Later May 10, 2016 39:05


    No. 10 — Take Vacations? by Diana Berlin & Lisa Sanchez

    No. 09 — Do Culture?

    Play Episode Listen Later Apr 27, 2016 32:54


    No. 09 — Do Culture? by Diana Berlin & Lisa Sanchez

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