The Real Question

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...

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...

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 l...

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/priv...

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...

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 w...

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 Janu...

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.

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...

The next person we're checking in with this week is Ely Kreimendahl – host of one of our favorite podcasts, Shame Spiral . How did things turn out for Ely? Was she able to quit nicotine? -- 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...

Across this holiday week, 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 Lacy from Should I Quit: Being a Teacher? -- 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...

Jacki has had a grudge against her cousin for the past three years. Jacki turned to her cousin during a tough time and left the situation feeling really abandoned and betrayed. But now, years later, still hurt, she’s wondering – is this grudge really serving her?  This week on Should I Quit? Jacki and Vanessa discuss how we process hurt and move forward.  -- This show is completely...

Five years ago, Penni Jo made a late-in-life decision to pursue a career as a songwriter. Now, with a few years of rejection under her belt, she’s wondering if it’s time to give up on that dream. Should she just get a ‘real job’ with better benefits? This week on Should I Quit? Miranda and Vanessa discuss financial security and what success feels like when you're pursuing your art. If you want to...

Anne Helen Petersen is the voice behind the popular newsletter, Culture Study , and the podcast, Work Appropriate . This week she joins Vanessa to talk about our relationship to work, social media, and aging. -- 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/privac...