The Real Question (Not Sorry)

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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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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Vanessa's step-daughter is *very* cool. But...is that a good thing? And what is coolness really?

With help from West Side Story and Gone Girl, Vanessa and Casper explore the social capital and social manipulation of coolness.

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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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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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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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Casper's life is on a path and generally he's pretty happy with how it's going. But every so often, he likes to fantasize about what it would look like to step off that path. What if, instead of living his normal life, he went on an adventure? What if he spent months traveling the world? Is that just a fantasy or is it something he can really do?

With help from Under the Tuscan Sun and Mary Oliver, Casper and Vanessa explore the fear and excitement tied up with choosing something new.

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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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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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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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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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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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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.

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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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Happy holidays! We're dropping in your feeds to share some news about the future of the show.

If you’re interested in being on the show, please fill out this form and we’ll start contacting people in the new year. 

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Dana Schwartz is a #1 New York Times Best Selling author (go read her new book!), top charting podcaster, and Twitter super-star. But still, she sometimes finds herself looking at other writers with feelings of professional jealousy. She doesn’t like that feeling when it comes up, but she doesn’t know what to do about it. 

With help from Nick Jonas and the movie Amadeus, Dana, Vanessa and Casper explore how feelings of inadequacy often lead to jealousy. 

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If you’re interested in joining Dana and Vanessa on our upcoming Frankenstein pilgrimage, there are still spots available! 

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Last fall, Sophie Clark broke up with her long-term partner and it was one of the hardest things she’s ever done. Trying to organize her grief, she began a weekly ritual - lighting candles and journaling about the break-up. But now, several months later, the ritual is feeling a little flat. What can she do to reimagine her practice to better fit where she is now in the grief process? 

With help from Jane Eyre and a William Prince song, Sophie, Vanessa and Casper explore what kind of thoughts and feelings surround a big break-up and what it means to heal. 

At the end of today’s episode, you’ll hear an original song by Sophie! You can hear more of her music here.

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Maya Gosh has been in pain for years. She’s been going to doctors, trying to figure out what's going on with her body, but nobody seems to think anything is wrong with her. And lately she’s started to feel like the whole process of trying to get good healthcare is more painful emotionally and psychologically than the physical pain she’s in. Should she stop trying and protect her mental health? Or is that giving up?

With help from Mythbusters and the Liverpool Football Club, Maya, Vanessa and Casper discuss everything that's at stake in trying to get a diagnosis.

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Ruth has been a woman their whole life, but that label has never quite felt right. Recently they had an experience where a stranger gendered them “wrongly” and it felt amazing. Since then they’ve been wondering, should they identify as non-binary? 

With help from Shakespeare’s Twelfth Night and an article by Tre’vell Anderson, Ruth, Vanessa, and Casper explore the confines of gendered language and the possibilities we have to expand it. 

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A few years ago, Lindsay left an abusive relationship. Since then she has almost completely cut her abuser out of her life. But there’s one friend they still share - and that friend is getting married. Lindsay has never talked to her friend about the abuse. But now, with her ex likely invited to the wedding, questions are coming up: Should she tell her friend about the abuse? What if he doesn’t believe her? Or still wants her abuser at his wedding? 

With help from In the Dream House by Carmen Maria Machado and Hunger by Roxane Gay, Lindsay, Vanessa and Casper discuss strategies for how to be vulnerable when you don’t know how a hard conversation will go. 

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If you or someone you know is experiencing intimate partner violence, The National Domestic Violence Hotline has great resources and are available 24/7 help.

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Dani has always wanted to live alone. Now, at 28, she’s living the dream. She owns her condo and doesn’t foresee needing a roommate. But looking ahead at the rest of her life, she’s a little worried about what she sees. If she lives alone forever, is she closing the door on an important kind of intimacy and support? 

With help from a song from Crazy Ex-Girlfriend and a scene from Friends, Dani, Vanessa, and Casper explore society’s expectations around partnership, family and long-term relationships.

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Marie-Hélène is the kind of person who changed her major a million times during college. But after a while, this habit started to feel embarrassing. So she made a promise to herself: “I am going to become the kind of person who commits to things and sees them through.” Now she’s been at the same job for seven years and is starting to feel antsy. But she can’t tell - is it because her old habit is rearing its head? Or is it because it’s really time to move on? 

With help from Independent People by Halldór Laxness and The Life of Pi by Yann Martel, Marie-Hélène, Vanessa, and Casper explore what it means to trust yourself when you feel like sometimes your instincts come from the wrong place.

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Sarah Steinberg is passionate about making stop motion animation. It’s so satisfying, she could easily spend hours at a time working a single project. But Sarah also lives with rheumatoid arthritis, which makes her art practice difficult and often quite painful. This worries a lot of her friends, they don’t understand why she insists on having a hobby that’s so hard on her body. How does Sarah explain to them why it feels worth it?

With help from the Lin-Manuel Miranda episode of Song Explorer and an episode of Sherlock, Sarah and Casper explore the balance between passion and pain, and what it means to to love someone with a disability.

Check out Sarah’s amazing work here. 

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Anna had her first child during the pandemic and she found her maternity leave to be really isolating and depressing. It was only once she was able to go back to school and work that she felt like herself again. But now she’s pregnant again and starting to get worried about her next maternity leave. What if she feels the same way? 

With help from the The Bright Field  by R.S. Thomas and A Line Above the Sky by Helen Mort, Anna, Casper and Vanessa explore the sacrifices and guilt associated with motherhood.

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We're cross-posting this special episode of Harry Potter and the Sacred Text, which we've released today. This year in commemoration of Juneteenth, Not Sorry is spotlighting The Final 5 Campaign, a coalition working to close the final five youth prisons in Illinois. Vanessa is joined in conversation by one of their leaders, Alicia Brown, who tells us about what it means to be a prison abolitionist and her work with the campaign. 

Please join us by making a donation, learning more about the failures of youth prisons, contacting your legislators about prisons in your state, and listening to their new podcast, Free The Youth.

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Mariah has filled her life with meaningful friendships. In fact, she bought a house with her best friend and is helping to raise her friend’s kid. Now she’s starting to think about what role a romantic relationship might have in her life, and she’s getting nervous. She knows a romantic partner would take up space in her life, space she doesn’t really have right now. If she wants a romantic partner, what would she have to give up? And would it be worth it? 

With help from the songs Into the Unknown from Frozen 2 and You are My Favorite by Heather Mae, Mariah and Vanessa explore the risks of seeking something new. 

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When Rachel was working on her PhD, she always thought she would graduate and work at a science museum. But the pandemic changed her plans, no museums were hiring. But now she’s wondering, was that change forever? Or should she try to work her way back to her passion? 

With help from the show All Creatures Great and Small and the book Ammonite by Nicola Griffith, Rachel, Casper and Vanessa explore the relationship between passion and work. 

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Hima’s parents moved to the United States when she was two years old. Her first language was Telugu, but her early teachers encouraged her parents to speak English at home. Now, she’s not entirely fluent. Hima knows that learning the language would probably make her feel closer to her family and her cultural identity – but it feels embarrassing to try, and trying comes with a lot of family baggage. Should she do it? 

With help from Braiding Sweetgrass by Robin Wall Kimmerer and Jane the Virgin, Hima, Casper, and Vanessa explore what meaning language can hold. 

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Lily has a boyfriend who she loves. But you know who she doesn’t love? Her boyfriend’s brother. He makes Lily feel small and hurt and honestly angry every time they see each other. But Lily wants to have a good relationship with her boyfriend’s family. So how does she deal with him? 

With help from Sara Bareilles and a scene from Fleabag, Lily, Vanessa, and Casper explore our relationships with in-laws and how to best deal with a bully. 

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Vanessa has always had very good instincts about people. But recently she's started to wonder: where does that gut instinct come from inside of her? And how can she make sure her 'gut' is reflecting her wisdom, instead of her prejudices?

With help from Into the Woods and Gilmore Girls, Vanessa and Casper explore how to give people the benefit of the doubt while still being able to trust your instincts.

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Funding for this episode was provided by UC Berkeley's Greater Good Science Center, as part of its "Expanding Awareness of the Science of Intellectual Humility" initiative, supported by the John Templeton Foundation. 

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Casper grew up with a lot of confidence. And as he’s gotten older, that confidence has only been encouraged and solidified by the various privileged identities that he inhabits. Knowing that, he wants to intentionally cultivate a practice of humility. But how do you temper confidence, without crumbing into self doubt? 

With help from the TV show Julia and The Methodist Quadrilateral, Casper and Vanessa explore how to tell the truth in every situation.

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Funding for this episode was provided by UC Berkeley's Greater Good Science Center, as part of its "Expanding Awareness of the Science of Intellectual Humility" initiative, supported by the John Templeton Foundation. 

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Casper recently joined The Happiness Lab with Dr. Laurie Santos for a special episode on overcoming loneliness–a feeling many of us are all too familiar with.

On The Happiness Lab, Laurie shares the latest scientific research and inspiring stories that will change the way you think about happiness. In this episode, Casper speaks to the benefits of belonging to like-minded communities and how they help our social lives thrive.

Hear more from The Happiness Lab at https://podcasts.pushkin.fm/thls5?sid=real.

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With help from Gilmore Girls and the song Closing Time from Semisonic, Vanessa and Casper explore the grief of endings and share about their upcoming projects. 

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You can find out more about The Nearness at https://www.thenearness.coop/. 

Should I Quit will premiere in late October. If you’d like to be on the show, you can submit here. 

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Is there something in your life that's making you miserable, but you feel like you need to just put your head down and get through it? Have you considered... just not doing it instead?

This week, Vanessa starts our new season of The Real Question with a thesis on why we should all be quitting more.

Next week, you'll hear from our first guest who is considering quitting. And if you'd like to be on the show, you can submit a question here.

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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When Eleanor got married, she took her husband’s last name. Now, nineteen years and three kids later, she’s working on a PhD. The PhD feels separate from her family life, something she’s doing just for herself. And so she’s started to wonder: Do I want to get this PhD under my married name? Or would it feel more ‘me’ to get it under my maiden name? 

This week on Should I Quit? Vanessa and Eleanor explore the power of names and what it means to feel like ‘you’ and be a mother at the same time. 

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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Mae lives in Texas. She grew up there, her whole family is there, there are a lot of things she loves about her life there. But now that she's raising two small kids, she's beginning to think: Is this really the environment I want my kids to grow up in? 

This week on Should I Quit? Vanessa and Mae explore the questions: What does it means to make a home in a hostile place? And at what point do you leave? 

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Our guest this week has a hard relationship with her dad. After years of hoping it would get better, she’s starting to feel like it might be time to quit. 

This week on Should I Quit? Vanessa and our guest explore the question: How do you love someone when they continue to hurt you? 

CW: This episode addresses addiction and includes reference to abuse. 

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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Casper spends a lot of time scrolling through YouTube videos. He feels like he should have a better evening routine, but the algorithm always pulls him in! Is it time to just go cold turkey? 

This week on Should I Quit? Vanessa and Casper ter Kuile explore what rest and self care look like in our day to day lives. 

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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Since the start of the pandemic, Shannon’s confectionary business has really been struggling. Now she’s getting kicked out of her shop space and she's wondering: is it worth it to move somewhere more expensive? Or should she just cut her loses and end the business? 

This Week on Should I Quit? Vanessa and Shannon explore when to accept failure and when to go all in.

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Please help us support Sweet Lydia’s by contributing to our fundraising campaign! You can send us money through our Venmo, and we’ll get all money to Shannon and keep you updated on the total. We’re hoping to reach $5400 by Christmas! 

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Hannah calls her parents…a lot. Like four times a day. She loves talking to them, but all her friends think it’s weird. So she’s started to wonder: am I being too clingy? 

This week on Should I Quit? Vanessa and Hannah discuss what makes for a healthy parent/child relationship and how to adapt to aging parents.

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Emily has always been passionate about decorating her home. It’s a big creative outlet for her! But the online culture around interior design has started to bother her – it's all focused around buying more stuff in order to feel good. And that actually doesn't feel good at all.

This week on Should I Quit? Vanessa and Emily discuss how social media and the forces of capitalism intersect in the world of home improvement.

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Vanessa and Ariana reflect on how the show's going and whether Vanessa's thoughts about quitting have changed since starting the season.

We're taking a short break for the holidays but we'll be back January 9th with our next episode!

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Beloved co-host of Harry Potter and the Sacred Text, Matt Potts, released his book Forgiveness: An Alternative Account a few weeks ago and it is so! good!! We're very excited to bring you an exclusive excerpt from the book - read by Matt himself.

You can find the book wherever books are sold, or snag a signed copy from our website!

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Cari has been dreading going to church. In theory, she likes so much about the community. But lately, she’s been resenting her obligations there. Is this just a rut? Or is it time to move on?

This week on Should I Quit? Vanessa and Cari discuss the challenges associated with being in community. 

If you’re interested in signing up for the Nearness, the next online six-week journey starts on January 23rd. Learn more on their website.

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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Jaime loves birds. Since they were eight years old they’ve wanted a career in bird science, and so far they’ve been living that dream! But a recently discovered chronic illness has been making the work more difficult. Is it time to move on from their life’s big passion? 

This week on Should I Quit? Vanessa and Jaime discuss how our dumb bodies get in the way of what we love.

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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When Cheyanne was twenty-three years old she made a rule: no long distance relationships. They just set you up for heartbreak! Every time she fell for someone far away, she stuck by her trusty rule. But now, nearly six years later and single, she finds herself questioning it. Is the rule keeping her from finding the right person? 

This week on Should I Quit? Vanessa and Cheyanne explore what we need out of partnerships. 

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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About a year and a half ago, Fran got sick. Since then, she’s been focused on getting a diagnosis and then trying to get better. But the kind of chronic illness she has – sometimes you don’t get better. Should she keep trying to get ‘back to normal’? Or it is time to come to terms with her life as it is? 

This week on Should I Quit? Vanessa and Fran discuss how to integrate a new version of yourself into your existing life. 

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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Lacy has been a teacher for fifteen year, and like many teacher’s right now, she’s feeling overwhelmed. School doesn’t feel the same as it did pre-pandemic. She feels pulled in a million directions, and out of hope. Is it time to quit teaching?

This week on Should I Quit? Vanessa and Lacy discuss how much to sacrifice for a job you care about. 

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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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Rin wants a life partner, but they’ve never felt romantically attracted to someone before. Should they keep dating, hoping that they’ll find the right person? Or is it time to give up on conventional love tropes and pursue another path?

This week on Should I Quit? Vanessa and Rin discuss how to build partnership outside of society’s norms. 

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Sami has been practicing the same style of Karate for 20 years; it’s a huge part of her identity. But a recent conflict with her Sensei has thrown her relationship with the sport up in the air. Can she go back to her dojo, knowing that things with her Sensei will never feel the same?

This week of Should I Quit? Vanessa and Sami discuss how one person can turn a good situation into a bad one.

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When Cameron joined the disability advocacy club during his first year of college, it became a huge part of his life. Now a junior, he's the club president, and being president opens a lot of doors campus-wide. The only the problem is – no one is really coming to the club meetings. Should he singlehandedly try to keep it running? Or is time to let it die?

This week of Should I Quit? Vanessa and Cameron discuss how to let go of things that aren't working anymore.

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Emily loves her boyfriend. There’s not enough good things to say about him: He’s kind and attentive and easy to be around. But she’s always wanted to be a mom, and he’s not so sure about kids. Can she stay with him, even if they don’t have kids? Or is that a dealbreaker? 

This week of Should I Quit? Vanessa and Emily discuss how to get what you want from a relationship without giving an ultimatum.

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Lisa has been a choir nerd for basically her whole life. But recently, with two young kids, she can barely stay awake for the rehearsals. Should she give it up to get more sleep? Or is this just a rough patch, and she’ll be glad she made it through the other side?

This week on Should I Quit? Vanessa and Lisa discuss how to keep a sense of self while being a mom. 

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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!

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Katie has written a novel. She worked hard on it and she thinks it's good, but the process of trying to get it published has been grueling. Should she just keep going? Or is it time to set the book aside?

This week on Should I Quit? Vanessa and Katie explore what it means to feel rejected and how much of that we each can tolerate.

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Hannah has lived in Chicago for the past seven years. She never really wanted to live there long-term, but now she's having trouble leaving. Her family and all her friends are in Chicago! She has a really good life there. Would it be a mistake to start over somewhere else?

This week on Should I Quit? Vanessa and Hannah discuss when to leave behind good things.

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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!

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During the pandemic, Brooke signed up for an online yoga subscription. Does she ever use it? No. Can she get herself to cancel it? Also no. 

This week on Should I Quit? Vanessa and Brooke discuss the psychological burden of our digital lives. 

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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!

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Brigid has gotten into the habit of telling white lies. It's a defense mechanism to feel in control of what people know and think about her. But is being so in control actually bad for her sense of self?

This week on Should I Quit? Vanessa and Brigid explore how to stop caring what other people think about you.

Did Brigid's question resonate with you? Submit something you respect about yourself and see what others have to say.

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Julia Argy, our incredible pilgrimage director has her first book out today! It's called The One, and it's about a woman who joins a reality television show to find love.

Publishers Weekly says it best: “[A] smart debut…Argy takes on voyeurism, feminism, and gender norms, as Emily wonders if she really ought to put all her energy into finding love, which is what she was conditioned to do all her life…. [A] winning portrait of a young woman trying to come into her own.”

In this bonus episode, Vanessa and Julia discuss what reality dating shows reflect about our own culture of love and surveillance. Julia's book is out today, be sure to check it out!

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Taylor gets sucked into looking at houses on Zillow. It's addictive! Comparing prices, imagining her life in different places... But is that imagining good for her? Or is it keeping her from appreciating the life she has?

This week on Should I Quit? Vanessa and Taylor explore when it's okay to plan for the future at the expense of living in the present.

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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!

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Chris Stedman gets stuck scrolling Twitter at night. He knows why he does it – it makes him feel in control, it soothes his anxiety. But should he be sitting in that anxiety instead of soothing it?

This week on Should I Quit? Vanessa and Chris explore our relationship to social media and how to counter perfectionism.

Be sure to check out Chris's latest book, IRL: Finding Our Real Selves in a Digital World, and his podcast Unread. (You can also find him on Twitter, of course, @ChrisDStedman.)

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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!

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Courtney loves posting photos of her kids on instagram – she loves scrolling back and seeing all the small moments captured, she loves being able to share those moments with family and friends. But her kids are young enough that they can't truly consent to the photos, and she worries that when they grow up, they won't approve of what has been shared.

This week on Should I Quit? Vanessa and Courtney explore how to evaluate risk as a parent.

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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!

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Heather Havrilesky is the voice behind the popular existential advice column, Ask Polly. This week she joins Vanessa to talk about giving advice, when to quit, and how to better be "your ragged-ass bullshit self."

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Margaret is a very sociable person – everywhere she goes, she finds new people to be friends with. But with that list ever-expanding, she feels like she's not serving her existing friendships as well as she'd like. Should she stop making new friends?

This week on Should I Quit? Vanessa and Margaret explore when it's okay to disappoint the people you love.

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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!

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Ely knows that vaping is bad for her, but she can't seem to find the motivation to stop. Is it okay to indulge certain vices? Or is that logic just the way that addiction works?

This week on Should I Quit? Vanessa and Ely explore our own self-destructive instincts.

In this episode, Ely mentions her experience with AA. If you or someone you love is struggling with addiction, there are AA meetings hosted around the world. You can find one near you on their website. And if you enjoyed hearing Ely, be sure to should check out her podcast Shame Spiral.

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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!

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As we prepare for our Not Sorry C.A.M.P. this week, we're taking a break from the show. We'll be back in two weeks, on June 19th.

In the meantime, please enjoy this un-locked Patreon perk, our Pop Culture Prescriptions with Vanessa and Margaret H. Willison. Our Patreon supporters make this show possible and we're so grateful. If you're a regular listener of the show, we'd love to have your support.

Also, please submit your quitting questions! We're always looking for new guests.

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We're taking one more week off of regular programming, but we'll be back next week on June 19th.

In the meantime, please enjoy this un-locked Patreon perk, our Should Vanessa Quit? segment with Vanessa and Ariana. Our Patreon supporters make this show possible and we're so grateful. If you're a regular listener of the show, we'd love to have your support.

Also, please submit your quitting questions! We're always looking for new guests.

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Every time Mars has a period they think about getting their uterus taken out. They hate having this dumb organ in their body! But doesn't everyone hate their period? And what if they want to have kids in the future?

This week on Should I Quit? Vanessa and Mars explore how we relate to our own bodies.

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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!

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Allie started running casually in college and has gotten more and more into it over the years. She joined a running club, she ran her first marathon, and she bought herself a fitness watch. But recently her fitness watch has been stressing her out. Is it the fitness watch that’s the problem? Or is it her relationship to running more broadly? 

This week on Should I Quit? Vanessa and Allie explore the difference between setting goals and gamifying your life.

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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!

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For the past fifteen years, Rob has been concerned about his relationship to opiates. One of the ways he has managed that relationship has been listening to podcasts about addiction. But recently he has been feeling like he doesn't like or need these podcasts anymore. Is it okay to stop listening?

This week on Should I Quit? Vanessa and Rob explore the guard rails we put up in our lives to protect us, and how to know when those guard rails aren't serving us anymore.

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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!

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Prerna has lived in The United States for over ten years but it will probably take her another thirty years to get a green card. She loves living in the US, but the bureaucracy, uncertainty, and limitations are big source of stress in her life. Is it all worth it? Or is time to try another country?

This week on Should I Quit? Vanessa and Prerna explore how much insecurity we each can tolerate.

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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!

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Jocelin has a crush on their friend Paul. Ever since they met, there's been an intense instant connection – they like all the same things, they text all day, they hang out constantly. But Paul doesn't have feelings for Jocelin. Can there still be a friendship? Or is it time to end it?

This week on Should I Quit? Vanessa and Jocelin explore what to do when a relationship becomes painful.

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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!

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Sarah owns a ballet studio in a small town. She loves dance and she loves teaching, but running her own business is really stressful! If she changes career path, will that give her the opportunity for a better life?

This week on Should I Quit? Vanessa and Sarah explore how to un-couple your identity from your job.

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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!

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Paige has had the same best friends for twenty years but lately they've been really letting her down. She doesn't feel seen or loved by them, and they don't seem to understand her perspective. Is it time to just end it?

This week on Should I Quit? Vanessa and Paige explore when it's okay to walk away from people you love.

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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!

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Shira has been trying to learn how to drive for the past two years. She failed her first driving test and recently, when trying to renew her learner's permit, she failed that too. Feeling extremely discouraged about the whole thing, she's now wondering: is it even worth it?

This week on Should I Quit? Vanessa and Shira explore how to accomplish something when you have no motivation left.

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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!

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G has always loved Harry Potter – so much so that in 2019 they joined their local Harry Potter and the Sacred Text group to meet monthly and make meaning from the books. When J.K. Rowling outed herself as transphobic a few years ago, G stuck with the group and their fandom. But lately, their experience as a trans person and a Harry Potter fan feel more and more at odds. Is it time to let go of the books they once loved?

This week on Should I Quit? Vanessa and G discuss how personal relationships with art and fandom can change over time.

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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!

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Kathy is turning 49 this year and she wants to be planning for the decade ahead! Should she continue on the career path she's on? Or it time to step off the path to try something new?

With help from Fredrick Beuchner and Lord of the Rings, Kathy and Vanessa discuss how to live a joyful life.

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Rebecca just had her second child and is spending a lot of time, focus, and energy on being a mom. But sometimes it feels like her whole life is consumed by that category! Even her instagram is filled with mom-related accounts and ads. Is that what she wants? Or should she unsubscribe and carve out one space where ‘mom’ isn’t the most important thing?

This week on Should I Quit? Rebecca and Vanessa explore shifting priorities and motherhood.

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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!

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We're thrilled today to be joined by Marcelle Kosman, co-host of one of our favorite podcasts – Material Girls. Marcelle likes to have a couple glasses of wine at the end of the day to unwind, but she finds it hard to talk about. Is it really okay that she drinks this much? Or is she fooling herself? And does just asking the question mean that she has a problem?

This week on Should I Quit? Marcelle and Vanessa discuss how to know when you're in denial.

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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!

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Over the last year, Miranda has taken some steps back from her relationship. They used to live together and now they live separately. She used to imagine marrying him, now it doesn’t seem in the cards. Is it time to just give up this man entirely? Or can she be happy with the comfort and pleasure of what she has in front of her? 

This week on Should I Quit? Miranda and Vanessa explore how to know when unhappiness in a relationship is normal and when it means you need to break up. 

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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!

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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.

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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!

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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 check out Penni Jo's music, you can find her on Spotify and Apple Music.

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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!

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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. 

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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!

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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?

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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?

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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.

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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.

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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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We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in!

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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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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!

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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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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!

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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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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!

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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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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!

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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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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!

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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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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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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!

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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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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!

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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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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!

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