Should I Quit?

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Episodes

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.

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. 

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? 

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. 

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. 

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.

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.

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.

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

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. 

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.

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. 

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. 

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. 

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. 

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

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.

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.

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. 

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.

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.

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. 

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.

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.

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.)

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.

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."

Margaret is 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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. 

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.

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.

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. 

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.

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.

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.

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.

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.

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.

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. 

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.

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.