The Real Question

Kaitlyn and her partner moved from Winnipeg to Halifax three years, excited to start a new life in a beautiful city. But three years later, they're still craving the sense of home they had in Winnipeg. Is it time to go back? This week on Should I Quit? Kaitlyn and Vanessa discuss how to know when you've given something new a 'fair' shot. -- This show is completely funded by Patreon, and we are so...

When Anisa and her husband got married, they mostly merged their finances – all except one little bank account that Anisa keeps on the side. Seven years into their marriage, Anisa is wondering: why am I keeping this account? Should I just shut it down? This week on Should I Quit? Anisa and Vanessa discuss the historical relationship between women and money and how to keep a sense of privacy in a l...

Mackenzi Lee is a New York Times bestselling author and the teacher of our upcoming Publishing Crash Course . This week she joins Vanessa to talk about how we measure success in the world of art and publishing. -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/priv...

We're thrilled today to be joined by Sarah Stewart Holland, co-host of Pantsuit Politics . Sarah was raised in a no-cussing household. When she got older, she embraced cussing and started using swear words all the time. But now, raising three boys of her own, she's realizing she doesn't find the words fun anymore. This week on Should I Quit? Sarah and Vanessa discuss how be a good role model...

When Lizzy was younger she always wanted kids. Over time, however, as the realities of life have crept in, she has started to feel more conflicted. Now she’s 35 and she feels like it’s time for a decision! Does she really want them? Or is time to quit the idea of kids for her future? This week on Should I Quit? Lizzy and Vanessa discuss how to tell the difference between what you really want and w...

Vanessa is joined by our Should I Quit? producer, Ariana, in our final episode of 2023. Together they look back at the past year of the show and share their take-aways and hopes for the future. We're also joined this week by Chaplain Rebecca Ledley, who works with Not Sorry through our Literary Chaplaincy program . Rebecca is running a group chaplaincy circle around Motherhood which starts on Janu...

In our final guest conversation of the season, we check back in with Emily from Should I Quit: My Relationship? We hear from Emily about the status of her love-life and her hopes for the future. -- We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information.

We're back with another Should I Quit follow-up! Today we're chatting with Fran, who was the guest on one of our first episodes this year. We hear from Fran about her continued journey with chronic fatigue syndrome. -- We are so grateful to our supporters on Patreon who make this show possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information...

The next person we're checking in with this week is Ely Kreimendahl – host of one of our favorite podcasts, Shame Spiral . How did things turn out for Ely? Was she able to quit nicotine? -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy for more information...

Across this holiday week, we're checking back in with some past guests. How did things turn out for them? Did they quit what they wanted to? Today, we're talking to Lacy from Should I Quit: Being a Teacher? -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privacy...

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

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

Anne Helen Petersen is the voice behind the popular newsletter, Culture Study , and the podcast, Work Appropriate . This week she joins Vanessa to talk about our relationship to work, social media, and aging. -- This show is completely funded by Patreon, and we are so grateful to our supporters who make it possible. If you can, please considering chipping in ! Hosted on Acast. See acast.com/privac...

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...

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? Marcel...

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 Vaness...

Producer Ariana drops into the podcast to discuss an upcoming change with Should I Quit? Hosted on Acast. See acast.com/privacy for more information.

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. Hosted on Acast. See acast.com/privacy for more information.

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 o...

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. -- This s...

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. -- This show is completely funded by Patreon, and we are so grateful to our...

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. -- This show is completely funded by Patreon, and we are so grateful to our supporte...

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. -- This sh...

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. --...

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...