Zoe was always proud of the fact that she didn't own a car. It reflected her environmentalist values and helped her stay more deeply in community. But after a recent move to Colorado, it's clear that a car would make her life a lot better. So she's wondering: when is it important to stick to your values even when it's hard? And when it is okay to revise your values to make your life easier? This week on Should I Quit? Vanessa and Zoe explore how keep yourself from complacency. -- This show is co...
Nov 25, 2024•26 min•Season 3Ep. 77
Shannon recently withdrew from her PhD program – with two young kids and a full time job, it wasn't the right time. Now, a few weeks out from the decision, she's asking herself: what's the plan? Does she set aside her dream of getting a PhD? Or should she plan on going back? If so, when? This week on Should I Quit? Vanessa and Shannon explore how to make slow decisions. -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, p...
Nov 11, 2024•28 min•Season 3Ep. 76
Megan believes in doing the ‘right thing’ even when it’s a little inconvenient, so she bought herself an ethical phone. This phone is supposed to be 'forever' – the answer to our cultural habit of constantly buying new technology every few years. This phone is also really annoying. But is it annoying enough to give up on her ideals and switch to a ‘normal’ phone? This week on Should I Quit? Vanessa and Megan discuss which small actions matter and how to stick with them. If you’re...
Oct 28, 2024•25 min•Season 3Ep. 75
After two years of Should I Quit?, Vanessa is moving on to other projects. The Real Question is sticking around though, with a brand new host and a new question! If you'd like to submit a final question for Should I Quit? or be one of the first voices in our next season, you can submit here . Hosted on Acast. See acast.com/privacy for more information....
Oct 21, 2024•8 min•Season 3Ep. 74
Stephanie used to call her dad every day. Then she realized: she was the only one putting work into their relationship. If she stopped calling, they stopped talking. So now, they don't really talk. But their relationship (or lack thereof) has been hanging over her head. Should she put the work in to try to fix it? Or is it time to just let go of the hope of a close and reciprocal relationship with her dad? This week on Should I Quit? Vanessa and Stephanie discuss how to have honest, loving and r...
Oct 14, 2024•26 min•Season 3Ep. 73
Andrea keeps having this problem: as soon as her single guy friends get a serious partner, it feels like she can't be close friends with them anymore. This doesn't happen with her female friends. It feels gendered, and it hurts. Is this going to keep happening? Should she stop investing in relationships with single, straight men? This week on Should I Quit? Vanessa and Andrea explore the unspoken rules and fears among single friends. -- This show is completely funded by Patreon, and we are so gr...
Sep 30, 2024•25 min•Season 3Ep. 72
We're thrilled today to be joined by story-telling coach Micaela Blei – the co-teacher of our upcoming memoir writing class . Micaela enjoys making her home beautiful. She's good at scouring thrift stores and finding just the right touch to bring everything together. She's also a little bit ashamed of how much time and attention she puts into buying home goods. Is she making her days at home easier and better through small improvements? Or is she frivolously spending on un-important things? This...
Sep 16, 2024•25 min•Season 3Ep. 71
Megan has always hated the dating apps. She's tried them – they're awful! Recently, however, she's been wondering if she should suck it up and give them another try. Is online dating truly the best way to find a romantic partner? Or should she continue waiting and hoping to meet someone 'organically' in the world? This week on Should I Quit? Vanessa and Megan discuss how to be clear-sighted and intentional while dating. Hosted on Acast. See acast.com/privacy for more information....
Sep 02, 2024•24 min•Season 3Ep. 70
Hope Rehak has been trying to treat her acne for the last 20 years. She's bought all kinds of things to 'help' – pills, shots, serums, and creams – but nothing has really worked long term. Is it finally time to just accept her skin for what it is? This week on Should I Quit? Vanessa and Hope discuss the struggles and limits of body positivity. If you enjoyed listening to Hope today be sure to check out her Substack, Obsessions this Week , and her upcoming screenwriting class ! -- This...
Aug 19, 2024•24 min•Season 3Ep. 69
For most of their life, Kat had a plan: move in with someone, get married, have kids. But recently they’ve been re-evaluating. They live with a long-term partner and are very happy. Would being ‘married’ change anything? Or do they just want marriage because that's what society has guided them towards? This week in Should I Quit? Vanessa and Kat explore why we want the things we want and how to ask for them. -- This show is completely funded by Patreon, and we are so grateful to our support...
Aug 05, 2024•26 min•Season 3Ep. 68
Elizabeth Oldfield wants to live radically in her faith. She wants to transcend traditional ideas of financial stability and community responsibility. However she can’t quite quiet the pragmatic voice in her head that’s tethering her to more conventional values. Is that voice helping protect her? Or is it holding her back? This week on Should I Quit? Liz and Vanessa dig into the question of security and how much we can protect our future selves. Be sure to check out Liz’s podcast The Sacred &nbs...
Jul 22, 2024•26 min•Season 3Ep. 67
Charlie James can't stop buying books. Every time they’re in a bookstore, there seems to be a new book calling them, a new trove of knowledge ready for them to explore. But Charlie's not reading books as fast as they’re buying them. Should they quit buying books and focus on their ‘To Be Read’ pile? Should they get rid of the books they already own? This week on Should I Quit? Vanessa and Charlie discuss what it means to be a ‘reader’ and its relationship to consumerism. if you want to che...
Jul 08, 2024•23 min•Season 3Ep. 66
It’s our last episode with Mauricio Bruce filling in as a guest host! This week on the show, our anonymous guest shares about the difficult relationship she has with her mom. Things have been painful for a long time and she feels like now is the time to ask: at what point should she put up some stricter boundaries? This week on Should I Quit? Mauricio and our guest discuss what to do when people want different things from the relationship and how to protect your happiness.&n...
Jun 24, 2024•28 min•Season 3Ep. 65
Vanessa is joined for a small bonus conversation by Margaret H. Willison, faculty on our upcoming Taylor Swift Pilgrimage on Cape Cod . They explore why Taylor's music is such a rich text for sacred reflection and share the things they're most looking forward to on this trip! If you're interested in joining us in November, you can sign up on our website ! Hosted on Acast. See acast.com/privacy for more information....
Jun 14, 2024•14 min
We’re continuing our short series with Mauricio Bruce filling in as a guest host. Mauricio is a transpersonal therapist, chaplain, and the co-leader of our What Matters program . This week on the show, our guest Katie shares with Mauricio about her desire to be a mom. She’s nearly 34 years old and she feels like the clock is ticking. The problem is she hasn’t found a life partner yet. She’s wondering: is it time to think about becoming a single parent? This week on Should I Quit? Maur...
Jun 10, 2024•27 min•Season 3Ep. 64
For the next few weeks on the podcast, while Vanessa is traveling, we have the wonderful Mauricio Bruce filling in as a guest host. Mauricio is a transpersonal therapist, chaplain, and the co-leader of our What Matters program . On our first episode with Mauricio, our anonymous guest is struggling with a tough decision about moving. On the one hand: She loves the currently city she is in. She feels the most herself, the most comfortable, the most at home, that she has felt in a long time. On the...
May 27, 2024•26 min•Season 3Ep. 63
Instead of a regular episode this week, we're sharing an episode of one of our favorite podcasts, The Best Advice Show . Last week, Vanessa had the pleasure of guesting on the show. You can listen to Vanessa's episode here , but today we're dropping a different episode from their archives – Deciding with Nell Wulfhart . Here's how the wonderful host, Zak, describes the podcast: The Best Advice Show is your reminder that there are weird, delightful and effective ways to make life slightly and som...
May 13, 2024•7 min•Season 3Ep. 62
Kelsie doesn’t always feel good about the work they're doing at their non-profit therapy job – and what’s more, they’re burning themselves out at it. Is there a better version of this work? Or do they just need to accept that in a broken world, we’re mostly going to have broken solutions? This week on Should I Quit? Kelsie and Vanessa discuss when it’s productive to compromise on your ideals. -- This show is completely funded by Patreon, and we are so grateful to our supporters who ma...
Apr 29, 2024•20 min•Season 3Ep. 61
Mauricio Bruce is a transpersonal therapist, chaplain, and the co-leader of our What Matters program . This week he joins Vanessa to talk about visualization as a decision-making tool and how to tap into your feelings. -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information....
Apr 15, 2024•23 min•Season 3Ep. 60
Sophie decided to take some time off work when she had her second child, but she always thought she would go back to her career in law. Since then however, one of her kids has become disabled and it has felt less and less possible to go back. Should she just give up on having a career? This week on Should I Quit? Sophie and Vanessa discuss how to be a caretaker and also take care of yourself. -- This show is completely funded by Patreon, and we are so grateful to our supporters who m...
Apr 01, 2024•23 min•Season 3Ep. 59
A few weeks ago we had on Sarah Stewart Holland of Pantsuit Politics and today we're joined by her brilliant co-host, Beth Silvers. Beth makes small donations to political campaigns because she feels like it's 'the right thing to do.' Lately, however, she has realized that her heart isn't really in it. Can she just stop making them? Or does that betray her platform, which is based on the idea of folks being politically engaged? This week on Should I Quit? Beth and Vanessa discuss what to do when...
Mar 18, 2024•27 min•Season 3Ep. 58
For our annual fundraiser at Not Sorry, we are again supporting the wonderful organization On The Rise. On The Rise’s work begins with individuals experiencing homelessness in Cambridge, Massachusetts and continues if and when they secure housing. From their origin as a women’s organization, their programs have evolved toward inclusion of those historically and structurally oppressed on the basis of gender. In today's episode, Vanessa sits down with On The Rise’s Director of Clinical Services, C...
Mar 14, 2024•27 min
Kaitlyn and her partner moved from Winnipeg to Halifax three years, excited to start a new life in a beautiful city. But three years later, they're still craving the sense of home they had in Winnipeg. Is it time to go back? This week on Should I Quit? Kaitlyn and Vanessa discuss how to know when you've given something new a 'fair' shot. -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted...
Mar 04, 2024•25 min•Season 3Ep. 57
When Anisa and her husband got married, they mostly merged their finances – all except one little bank account that Anisa keeps on the side. Seven years into their marriage, Anisa is wondering: why am I keeping this account? Should I just shut it down? This week on Should I Quit? Anisa and Vanessa discuss the historical relationship between women and money and how to keep a sense of privacy in a long term relationship. -- This show is completely funded by Patreon, and we are so grateful to our s...
Feb 19, 2024•21 min•Season 3Ep. 56
Mackenzi Lee is a New York Times bestselling author and the teacher of our upcoming Publishing Crash Course . This week she joins Vanessa to talk about how we measure success in the world of art and publishing. -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information....
Feb 05, 2024•27 min•Season 3Ep. 55
We're thrilled today to be joined by Sarah Stewart Holland, co-host of Pantsuit Politics . Sarah was raised in a no-cussing household. When she got older, she embraced cussing and started using swear words all the time. But now, raising three boys of her own, she's realizing she doesn't find the words fun anymore. This week on Should I Quit? Sarah and Vanessa discuss how be a good role model for your kids. -- This show is completely funded by Patreon, and we are so grateful to our supporter...
Jan 22, 2024•24 min•Season 3Ep. 54
When Lizzy was younger she always wanted kids. Over time, however, as the realities of life have crept in, she has started to feel more conflicted. Now she’s 35 and she feels like it’s time for a decision! Does she really want them? Or is time to quit the idea of kids for her future? This week on Should I Quit? Lizzy and Vanessa discuss how to tell the difference between what you really want and what you feel like you should want. -- This show is completely funded by Patreon, and we are so grate...
Jan 08, 2024•22 min•Season 3Ep. 53
Vanessa is joined by our Should I Quit? producer, Ariana, in our final episode of 2023. Together they look back at the past year of the show and share their take-aways and hopes for the future. We're also joined this week by Chaplain Rebecca Ledley, who works with Not Sorry through our Literary Chaplaincy program . Rebecca is running a group chaplaincy circle around Motherhood which starts on January 22nd. You can find out more at: https://notsorryworks.com/journeying-through-motherhood -- We ar...
Dec 29, 2023•31 min•Season 3Ep. 52
In our final guest conversation of the season, we check back in with Emily from Should I Quit: My Relationship? We hear from Emily about the status of her love-life and her hopes for the future. -- We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information....
Dec 28, 2023•8 min•Season 3Ep. 51
We're back with another Should I Quit follow-up! Today we're chatting with Fran, who was the guest on one of our first episodes this year. We hear from Fran about her continued journey with chronic fatigue syndrome. -- We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information....
Dec 27, 2023•8 min•Season 3Ep. 50
