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 week on Should I Quit? Micaela and Vanessa discuss how to know if our self-soothing techniques are positive or over-indulgent.

If you enjoyed hearing Vanessa and Micaela on this episode, you can sign-up for their class: https://notsorryworks.com/writing-workshops-2024#memoir

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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.

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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 sometimes profoundly better. In every (very short) episode of the show, a different contributor offers their take on making life more joyful, healthful and livable and it's likely gonna be something you can try today, if you want. 

We'll be back in two weeks with our regular format! In the meantime, be sure to subscribe to The Best Advice Show.

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Risa has a family member who isn’t getting vaccinated and the relationship is really troubling her. She wants to respect the values of the person she loves, but is finding that hard to do when the ‘right thing’ seems to be so clear.

With help from a Brandy Carlile song and a blog post by Lilach Shafir, Risa and Casper explore how to be in relationship with someone who has values that seem diametrically opposed to your own. 

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Vanessa used to have a helpful story she told herself about her depression. She let herself stay in bed some days and understood that it was important for her health. But lately, she hasn’t been staying in bed. The story seems…broken, like it doesn’t fit the new version of her life. Is there a new story that could help her take care of herself better?

With help from Buffy the Vampire Slayer and Cheryl Strayed, Vanessa and Casper explore how to think about mental health when there’s so much pressure to be productive. 

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Casper is feeling a lot of nostalgia for his graduate school experience. There are so many times in his day to day life where he feels like he should know more and he wishes that he had a teacher to guide him. He's been trying to teach himself, but it just doesn't feel the same. Should he just go back to school?

With help from Legally Blonde and Hermes Trismegistus, Casper and Vanessa explore how learning gets institutionalized and how we can make room for it after school is over. 

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Back in May, Vanessa brought us the question 'am I a Karen?' That episode focused on gender and the way systems of power can fail and frustrate women. This week we bring you part two of that conversation, where we discuss the racial dynamic at play in the Karen meme. We were incredibly lucky to be joined by Dr. Apryl Williams for this conversation. Dr. Williams is a multidisciplinary scholar who studies the experience of race and racism in digital spaces.

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Casper has a soft spot in his heart for the monarchy. He understands all the absurdities of the institution, but he can’t get rid of that feeling that he associates with childhood and history and national identity. Is it okay to have that feeling knowing what he knows intellectually? Or should he be trying to get rid of it? 

With help from Mrs. Dalloway by Virginia Woolf and The Mirror and the Light by Hilary Mantel, Casper and Vanessa reflect on what it means to glorify national stories and how to go about dismantling them.

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Every so often Vanessa scrolls through photos on her phone and runs into some memories she’d rather forget. Should she just delete those photos? Or are those bad memories something productive? 

With help from Spotlight and Mad About You, Vanessa and Casper explore what it means to re-write our own historical record and when we should do it.

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Casper is getting older and he's been thinking about what that means. On the one hand: age is just a number! There’s no such thing as the ‘right’ thing you should be doing at any age. But on the other hand: he wants to make sure he’s stepping into the full responsibility of what it means to be an adult. Without subscribing to tradition benchmarks, how do you keep yourself on track?

With help from David Sedaris and Shakespeare, Casper and Vanessa think about the 'stage' of middle age and what Casper should be doing with it.

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Instead of a normal episode this week we're bringing you an episode of The Happiness Lab with Dr. Laurie Santos, featuring our own Casper ter Kuile.

Space crews, athletes and pop stars all indulge in strange rituals before moments of high stress. It's easy to mock these behaviours - indeed even the people who practise them often admit they're a bit weird - but they can act like performance enhancing drugs. Dr Laurie Santos looks at the research to show why creating a good luck ritual can make us perform better and feel calmer, happier and more confident when faced with life's big moments.

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Vanessa has had a lot of really positive interactions with strangers. However there are moments when strangers, for whatever reason, trigger her defense mechanisms. What should she do in those moments? She doesn't want to be naive - there are people out there who can hurt you or take advantage of you. But also, she knows it's important to be kind whenever possible.

With help from Thelma and Louise and an episode of Radiolab, Vanessa and Casper discuss whether we should assume good intentions in strangers.

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Casper is suspicious of the value he puts on beauty in his life. He knows that he doesn't want to judge human bodies by their aesthetics, that much makes sense. But is it okay to love other forms of beauty out in the world? Or is that problematic too?

With the help of a Shakespearean sonnet and 'How Fair This Spot' by Rachmaninoff, Casper and Vanessa untangle how to think about beauty as a moral category.

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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. 

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Vanessa doesn't know what to do when people ask her 'are you okay?' A lot of the time, she is not okay. She lives with a chronic illness, so unfortunately that kind of comes with the territory.

On the one hand, radical honesty and communication is good. On the other hand, other people have their own problems. And most of the time, it's not like anyone can actually help.

With help from I Am, I Am, I Am by Maggie O'Farrell and Cinderella, Vanessa and Casper explore the allure of a 'suck-it-up' mentality and how to be in relationship as someone who's hurting.

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Casper has never liked his middle name. He’s ready to change it to something more meaningful to him, but how does he go about picking the right replacement?

With help from John O’Donohue and Call Me By Your Name, Casper and Vanessa explore the connection between re-naming and a spiritual life.

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John Green has spent much of his life and career online. The community that he’s built there has been one of his greatest joys and achievements. But more and more he feels like his time on social media is poisoning his sense of well-being. Should he just give it up? Or would that be turning his back on something too valuable?

With help from an essay by Thomas Berry and an episode of the podcast Your Undivided Attention, John, Vanessa and Casper explore the addictive quality of being online and if there's anyway to escape it.

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Vanessa has some friendships that feel more like obligations than pleasures. What does she do with these friends? Does she break-up with them? Does stick it out and hope that they become fun again? Does she tell them how she feels? And how does she do any of it without hurting the people she cares about?

With help from the musical Waitress and Erich Fromm’s The Art of Loving, Vanessa and Casper weigh the value of clear communication versus the potentially healthy ebb and flow of life-long friendships.

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Recently, Casper’s been looking back on his life with regret: he should have kissed more boys when he was younger! But what is he supposed to do with that feeling now? And how can he make sure that he’s living his life in a way that he won’t regret in the future?

With help from a poem by Lucille Clifton and How Proust Can Change your Life by Alain de Baton, Casper and Vanessa try to parse what exactly the feeling of 'regret' is and what we can learn from it. 

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Vanessa sometimes tells white lies in low stakes situations. Lies like ‘yes, I love that dress!’ or ‘I really enjoyed meeting your boyfriend!’ Are these lies good for her relationships? Or do they make her untrustworthy?

With help from Trust Exercise by Susan Choi and Grey’s Anatomy, Vanessa and Casper try to untangle the relationship between truth and trust and figure out when it’s okay to lie. 

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Casper is getting to the age where he feels like he and his husband ’should’ start thinking about buying a house, but he doesn’t know if he really wants to. On the one hand, there's so much love and stability that is wrapped up in owning a house. On the other hand, he doesn't know if he ever wants to settle on one future in one place. Maybe buying a house would limit his future possibilities?

With help from a picture of his childhood home, and theologian Walter Breuggemann, Casper and Vanessa discuss how to intentionally cultivate hospitality and whether stability is a goal or an illusion in life.

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Every summer Vanessa goes to Germany with her partner, Peter. And every summer, Vanessa gets stuck around the dinner table at night surrounded by people speaking German (a language she does not speak). What she really wants to do in that situation is pull out a book… but that’s rude right?

Drawing on Romance Mr. Bridgerton by Julia Quinn and the essay ‘Reflections on the Rights Use of School Studies with a View to the Love of God’ by Simone Weil, Vanessa and Casper examine what rudeness really is and when we should be willing to step our toe over the line.

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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.

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Following the death of his grandmother, Casper has had some uncomfortable and unresolved questions about death and the afterlife. He used to feel very certain that death was the 'end' everything, but now he's not so sure. Is there such a thing as a 'soul'? And if so, does it go somewhere when the body dies?

Drawing on Leo Tolstoy’s War and Peace and a medieval illustration of death, Casper and Vanessa explore ideas about death, dying, and how we remember those who are gone.

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Vanessa has a friend she wants to break-up with. The case is very clear cut: This person did something awful, and Vanessa no longer wants this person in her life. Does Vanessa owe it to this person to tell her that the friendship is over? And how does she tell the other people who might be effected by this friend break-up?

Drawing on Jacques Derrida's theory of friendships and the U.S. version of The Office, Vanessa and Casper discern how to know when a friendship is over and what the right way convey that information is.

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Casper has lot of rituals in his life to slow down: he keeps a sabbath every week, he spends time at a monastery every few months. But still, he rarely feels truly relaxed. What's standing in his way, and what does it take to get there?

Drawing on wisdom from The West Wing and German Philosopher Josef Pieper, Vanessa and Casper unpack what our culture has come to assume about work and worthiness and examine whether there's something spiritual about leisure.

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The term 'Karen' has imbedded itself in our culture, and as a white woman, Vanessa is keenly aware of the moments she might be called a Karen. But she's not quite sure when she's actually being a Karen, and when she's advocating for herself in a sexist society.

Drawing on the movies Terms of Endearment and Mommy Dearest, Vanessa and Casper discuss women's anger and what to do with it.

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This week, we’re joined by special guest Brigid Goggin who is bringing her own question to the podcast.

Brigid loves setting boundaries and saying no. But as a person who suffers from anxiety, she worries that sometimes she is saying ‘no’ for the wrong reasons. How do you know when you should actually be saying 'yes' to something?

Drawing on the song Climb Every Mountain from The Sound of Music, and the book Fangirl by Rainbow Rowell, Brigid, Vanessa and Casper think through how community can help us make good decisions.

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Following up on last week’s conversation, Casper and Vanessa return to some questions about the nature of evil. When do people do evil things and how do we prevent that from happening in ourselves?

Drawing on the theology St. Augustine of Hippo (as shared by our friend Nick Hayes) and The Lord’s Prayer, Vanessa and Casper try and figure out how to keep ourselves oriented towards good in the world.

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Casper used to believe that there was no such thing as evil. But since the Trump presidency, he can't suppress the creeping feeling that some people genuinely don't have good intentions. Does that count as evil?

Drawing on the philosophy and letters of Hannah Arendt and the movie adaptation of Harry Potter and the Goblet of Fire, Vanessa and Casper work through what Casper truly believes about what evil is and how it operates in our world.

This episode is Part 1 of a two part series, we'll be back next week with further conversation on the topic of evil!

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CW: We discuss weight loss and size in this episode.

Vanessa owns the perfect polka dot dress. It’s sophisticated yet flirty, it makes her feel amazing every time she wears it, and it has the cutest gold button on the back. The problem is: Vanessa no longer fits in this dress. She hasn’t fit in it for a while now. Should she hold onto it just in case? Or is it time to say goodbye?

Drawing on the poem One Art by Elizabeth Bishop and the Disney movie Lilo & Stitch, Vanessa and Casper work through the questions and difficulties of body positivity.

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What do we owe our neighbors? 

When Casper first moved to New York, he put a lot of effort into getting to know the other people in his apartment building. He even threw a rooftop party so that everyone could have the chance to meet one another. Now, as he’s settling into his life in NYC, he’s asking himself how much effort he really wants to put into knowing his neighbors. Should he throw another party for the new people moving into the building? Or is okay to spend his time building community with friends and family instead?

Drawing on the book Community by Peter Block and Game of Thrones, Casper and Vanessa think through how much we should be valuing neighborliness and local community in our lives.

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Sometimes apologies that seem 'good' technically, don't actually make Vanessa feel any better.

Is there a formula for a good apology? How do you explain yourself, but still take responsibility? Drawing upon Dirty Dancing and Letter From Birmingham Jail by Martin Luther King Jr., Casper and Vanessa think through which apologies feel the most genuine and why.

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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. 

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Casper wants to feel closer to his paternal grandparents. But there’s a problem: they’ve been dead for a few years now. Is there a way, as he grows older, for him to keep his grandparents an active part of his life?

Drawing upon The Suitcase by Frances Stoner Saunders and Children and Art from the musical Sunday in the Park with George, Casper and Vanessa think through how grief changes over time.

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CW: This episode discusses multiple instances of sexual assault and violent crime.

In 2014, Vanessa was obsessed with the Woody Allen/Dylan Farrow case. Now that there’s a new documentary out on the topic, she knows she’s in danger of falling back into the ‘story’. But what’s the virtue of following a story of sexual assault so closely? Is it good to know the facts? Or is it just using the horrors of someone else’s life as our entertainment? 

Drawing upon The Art of Cruelty by Maggie Nelson and the TV show Veronica Mars, Vanessa and Casper try to define how to have a healthy relationship with news stories about sexual assault specifically, and the True Crime genre in general.

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If you don’t learn to drive, are you failing to equip yourself for adult life? 

Casper has promised himself every summer that *this* is the year he’s going to learn how to drive. And yet each year passes and Casper is no closer to having a license. Drawing upon The Sabbath by Abraham Joshua Heschel and the song Walk the Road by Kate Rusby, Casper and Vanessa try to sort out which goals it’s okay to give up on. 

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Is it weird to steal children’s body parts in the middle of the night and teach them that it’s okay?

After playing the Tooth Fairy for her two step-daughters, Vanessa is having doubts about the appropriateness of this supposedly silly childhood ritual. Drawing up a recent article about the Marquis de Sade and the song Super Trouper from Mamma Mia, Vanessa and Casper try to wade through the fears that a parent can have for their kids.

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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 you feel like a fraud.

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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, Charyti Reiter to talk about misconceptions around homeless. We hear also from one of On The Rise's participants, JS. 

You can help us reach our goal of $10k by donating here. 

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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.

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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.

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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.

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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.

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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!

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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.

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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

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