The Real Question

Before we end 'Should I Quit', we're checking back in with some past guests. How did things turn out for them? Did they quit what they wanted to? Today, we're talking to Kaitlyn from Should I Quit: Halifax? -- 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...

Not Sorry has launched its first new podcast since 2020! Let's Ask Taylor Swift  is co-hosted by Vanessa and podcaster, writer and cultural critic: Daniel Schroeder.  In each episode Daniel and Vanessa will focus on one song from Taylor's discography, asking themselves, each other, and you— the audience— what it is about Taylor's music that resonates so...

Julia has three toddlers at home. Her first child stop breastfeeding recently and it was a gradual process of feeling out when he was ready. But with her younger twins, breastfeeding has been harder – it's been making her sick. Should she stop breastfeeding them now to save herself from future illness? Or is it important to extend the same opportunity to her younger kids that her first child...

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 w...

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 comple...

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 Shoul...

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.

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...

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...

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 easie...

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 a...

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 s...

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...

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 securi...

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...

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 wha...

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...

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 wonder...

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 feel...

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 Sho...

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....

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....

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...

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 f...

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...