Sunday Questions the Podcast

In today's episode, Cailin offers listeners her recipe for changing their life. From podcasts to listen to, books to read, foods to eat, habits to implement, and things to avoid, this episode gives listeners looking to change their life a prescription for exactly how to do it. Other tangents include: Cailin's weekly REPORT, chatting about personal evolution & and an impassioned tribute to family.

In today's episode, Cailin responds to listener write-ins for another Sunday advice session. Complete with an unnecessarily long life update to kick off the episode, this conversation covers all things ranging from long distance relationship tips to dealing with imposter syndrome, work life balance, dating, small talk, and finding your authentic self in college.

In today's special episode, Cailin is sharing the most raw account of her mental health journey to date in an interview with filmmaker Jay Devore at the Release Recovery office in New York City, filmed this past spring. Unedited and with video footage, this episode covers Cailin's story of mental health from being a young athlete, to depression, all the way to the unheard aspects of her so...

In today's episode, Cailin's back with a solo episode filled with life updates from her summer, feelings about being back at school for her senior year of college, and some exciting career news. Topics include: processing overwhelm and communicating through change, being selective with the "yes's" you give out when you're in a transitory period, understanding how full you...

In today's episode, Cailin interviews a dream guest of her's: Sarah Levy, author of Drinking Games. Part memoir and part social critique, Drinking Games is about how one woman drank and lived— and how, for her, the last drink was just the beginning. On paper, Sarah Levy’s life was on track. She was 28, living in New York City, working a great job, and socializing every weekend. But Sarah h...

In today's episode, Cailin interviews Lily Nikias (@seeing_lily) about moving to Australia at 22. This conversation covers a number of topics ranging from Lily's decision to follow a gut feeling, initiating friendships, intentionally using social media, and just being a generally self aware person. Lily is brilliant, lovely, and the easiest person to talk to -- we're so excited to brin...

With an impending 21st birthday later this month, Cailin recounts the twenty lessons she learned during her twentieth year of life. Topics of discussion range from the thing she struggled with the most this year, to the time she ghosted her boss, all the way to overcoming anxiety around meeting new people and accepting the ever-flowing tides of friendship.

In today's episode, which listens not unlike a therapy session without a qualified therapist, Cailin breaks down her own fears and limiting beliefs. Topics range from being vulnerable to uncertainty and volunteering ourselves to uncomfortable emotions, to Cailin having revelations about her confusing relationship with hard work. Complete with submissions of listener fears and limiting beliefs,...

In Cailin's favorite episode yet, per many requests of the podcast listeners, we have flower boy (formally known as Cailin's boyfriend, Sam) on the podcast. In this episode, Cailin and Sam chat about all things relationships, ranging from the unique story of how they met, to how they intentionally create intimacy in their relationship, to setting precedents in the early stages of a relatio...

Straight from the notes app, today Cailin is sharing a list of bullet points describing aspects of her personality that you probably wouldn't get from her social media. Highlights include: a dramatic reading of letters Cailin wrote to her parents as a child, high praise for tortilla chips, and Cailin's inability to dress appropriately for the weather.

To kick off the summer, Cailin had a month long crisis about her appearance. Here's her actionable steps to get out of a confidence funk.

After wrapping up her third year in college, host Cailin Bracken shares her insights on ten lessons she learned throughout the year. Topics include: moments of growth and healing, embracing the idea that life doesn't owe us anything, approaching conflict productively, and knowing when to let go. Especially fun podcast highlights include but are not limited to Cailin discovering that she's...

In today's advice session, Cailin responds to your write-ins. Topics include heartbreak, body image, establishing good habits, navigating your 20s, finding your routine in college, among other things. Enjoy!

On this week's episode, Cailin is joined by two dear friends who happen to be sisters: Blakely and Savannah Spoor. The creative minds and eyes behind @madison.spain on Instagram and writers of Cailin's favorite newsletter, Blakely and Savannah Spoor are some of the most interesting, dynamic, and grounded people you could possibly spend an hour listening to. Today they're on the podcast talking abo...

In today's episode, Cailin talks about all things timelines, and more specifically her qualms with them. This episode examines how we understand the future, why we're constantly rushing towards a perceived finish line, and how we can re-center ourselves in moments of indecision by asking one simple question. Casually compelling conversations in today's episode include: dealing with post-grad caree...

In today's episode, Cailin breaks down her experience with anxiety and shares the tools she's learned to cope with moments of anxiety, panic, and uncertainty ranging from mindset reframes to taking medication. Cailin discusses the valuable lessons we can learn from the things we have anxiety about, how OCD taught her to be comfortable living alongside life's uncertainties, anxiety and anxious atta...

In today's episode, Cailin is joined by her mom, Meghan Bracken, as they discuss a variety of topics centering on healing parent-child relationships and how we can better understand and communicate our needs with our caretakers. Cailin and Meghan discuss the evolution of their own relationship as mother and daughter, and how they navigated their way out of constant contention and into meaningful f...

In today's solo episode, Cailin comes back from her week and a half long hiatus (unthinkable) to provide a twenty minute life update that absolutely nobody asked for.  Though it sounds more like a voice memo to a friend than a podcast episode distributed on globally accessed streaming platforms, this episode is a special one. Topics range from: Cailin's recent trip to Washington D.C. to meet with...

On today's episode, Cailin is joined by guest and dear friend, Fiona Neville. A writer, blogger, and self-development extraordinaire, it was only matter of time until Fiona made her appearance on Sunday Questions. In this episode, expect detailed discussions on how to live a sexy life (a favorite word of both Cailin and Fi's), Fiona's decision to give up social media for forty days, and why we can...

In today's belated-valentine's day special, Cailin talks about all things romantic relationships. Topics range from things Cailin has learned via flopping in her own relationships, things that keep us from finding an authentic partnership, things that Cailin believes are critical for achieving longevity in relationships, and why comparison kills relationships. Highlights include: an advice session...

In today's episode, Cailin finally shares the '23 Habits in 2023' list that she's been alluding to in the past three episodes. Complete with habits ranging from "I will not say goodnight to a man who is not my blood relative unless he is my boyfriend" all the way to starting a high yield savings account and automating your savings. Notable topics include: Cailin airing grievances about people who...

In part one of today's episode, Body Image, Eating Disorder Recovery & Eating for Your Gut, Skin and Brain, Cailin discusses her own (rich) history with disordered eating and poor body image, among other things. This episode follows Cailin's experience with an eating disorder beginning at age 10 and transitioning into her later teenage years, throughout which she confronted her relationship wi...

In this episode, Jumpstarting Your Personal Evolution: Lessons That Took Me 20 Years to Learn & Perspectives That Changed My Life, Cailin sits down and shares lessons she's learned, pieces of advice she's acquired, and perspectives on the human experience that have changed her life forever and have been living in her notes app ever since. There's no gatekeeping on Sunday Questions, so this advice...

In today's episode, Cailin talks through the evolution of her relationship with alcohol and invites the audience into the conversation by way of a Q&A in which Cailin speaks to aspects of being sober as a young adult, offers advice, and shares what she has learned over the past year and a half+ of sobriety. In this longer form episode, topics range from navigating dating and romance in sobriety to...

In today's episode, Cailin brings on guest and dear friend Miranda McKeon to discuss social dynamics regarding the life of an influencer. Cailin and Miranda discuss why so many people are afraid to start being vulnerable on their primary social media accounts, how to start showing up authentically online, why nobody is actually looking at you like you probably think they are, and the fact that you...