Kaitlin Lost Her Ambition (The Heart)

Summary

Proxy with Yowei Shaw

Episode: Kaitlin Lost Her Ambition (The Heart)

Release Date: July 8, 2026

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Overview

This episode of Proxy is an audio "proxy" featuring acclaimed audio producer Caitlin Prest (of The Heart), examining her recent loss of ambition, transition away from traditional measures of career success, and discovery of new meaning in quieter forms of creativity. Through diary entries, reflection, and intimate moments with her father, Caitlin explores ideas of adulthood, productivity, familial support, and the redefinition of artistic value. The episode serves as a meditative look at what happens when ambition fades, and how connection and small acts of beauty can create new purpose.

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Key Discussion Points & Insights

1. Caitlin Prest’s Career Reassessment

• Background: Caitlin is renowned for her bold, intimate, and award-winning audio documentaries (The Heart), often delving into bodies, gender, power, and relationships.
• Current Situation: Instead of pitching big-budget stories or holding a conventional job, Caitlin now lives with her parents in Ontario, making "quieter" radio in a much different context than the high-achieving world she came from.
• Crisis of Ambition:
  • Caitlin: “I've been joking that I'm having an existential crisis, but it's not really a joke. I don't believe in the structures of our society anymore. I've lost my ambition. I've lost the desire to excel by the standards of the American entertainment industry.” (02:59)
  • She frames her latest project, Suburban Paradise, as a “simple, playful, humble offering”—reflecting a major shift in her own value system.

2. The Search for Meaning Beyond Traditional Success

• Connection and Beauty:
  • Caitlin recounts a Sufi preacher’s story:
    “What about beauty?... creating things of beauty as an artist is a way of connecting with the divine... and so to create beautiful things matters, I believe. I mean, not to say that what I'm making is beautiful, but I guess I’m… striving for that.” (03:50)
• Letting Go of Old Ambitions:
  • No longer invested in external achievement, Caitlin searches for self-worth through small, personal acts of creation and presence.

3. Sound, Listening, and Healing

• Soundscape as Connection:
  • Caitlin guides listeners through her auditory world, inviting attention to subtle details:
    “Observing the sounds around us is a way of tuning in. Julia Cameron says that giving attention is an act of connection. And the reward that we get for that attention for that connection is healing.” (06:45)

4. Reflective “Dear Diary” Segments: Family, Adulthood, and Failure

• Parent-Child Dynamics:
  • Through a diary entry, Caitlin describes a role-reversed day “working” with her father, celebrating small tasks with a “Ta Da List” instead of a “To Do List”:

    “I offer lateness a sliding scale start time... And 40 minutes later we start the day. I start to write a to do list. I tell my dad about the philosophy of the TADA list... He took to the concept... it was a gift that kept on giving throughout the day.” (09:51)

• Questioning Adult Status:
  • She reflects on societal expectations tied to adulthood and productivity:

    “It's strange how adulthood can kick you out of itself. It's a status we're always being threatened we'll lose if we aren't perfect parents, we lose our status as an adult. If we can't pay our bills, we lose our status as an adult. If we move in with our parents... we most definitely lose our status as adults.” (12:10)

  • The diary shares both vulnerability and humor at the intersection of parental support, failure, and personal growth.

5. Celebration of Small Wins

• The “Ta Da List” Ritual:
  • In a candid audio segment, Caitlin and her dad literally high-five over each completed small task:
    • Dad: "Ta da. Another one off the list. Let's do it... These are pretty tough ones, you know. So very, very good." (16:14)
    • They make exaggerated “checkmarks” and “stars” for each accomplishment, re-framing productivity as a joyful, communal act.

6. Art, Identity, and Economic Realities

• Unemployed (or Funemployed?):
  • Caitlin jokes and muses on her chosen state:

    “Technically, I wouldn't call what I am unemployed. I wouldn't call it fun. Employed. I hate. I really do hate puns. Even though I did a lot of them. I did those for Natalie. Natalie, look what you've done to me...” (16:58)

  • She describes a deliberate choice not to monetize her latest art, inviting listeners to donate to the “Unemployed Philosophers Guild” as a tongue-in-cheek gesture towards the financial precarity of artists outside the mainstream.

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Notable Quotes & Memorable Moments

• Caitlin Prest on existential crisis:

  “I've been joking that I'm having an existential crisis, but it's not really a joke. I don't believe in the structures of our society anymore. I've lost my ambition.” (02:59)

• On beauty and creation:

  “I believe that creating things of beauty as an artist is a way of connecting with the divine... to create beautiful things matters, I believe. I mean, not to say that what I'm making is beautiful, but... I'm striving for that.” (03:50)

• Redefining adulthood:

  “It's strange how adulthood can kick you out of itself... we lose status for being frivolous, unreliable... But for some reason we don't lose status for being cruel. We don't lose status for being selfish. We still get to be an adult even if we're boring.” (12:10)

• On teamwork with her dad:

  “He was the username, I was the password, he was the email address and I was the backup mobile phone number. I was the to do list, long and overwhelming and he was the Ta DA list...” (12:10)

• Cheerful affirmation from her dad:

  “Ta da. Another one off the list. Let's do it... Big fantastic. These are pretty tough ones, you know. So very, very good.” (16:14)

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Timestamps for Key Segments

• 00:57 — Podcast recollections: Caitlin as a disruptive, boundary-pushing presence.
• 02:59 — Caitlin’s existential crisis and loss of ambition.
• 03:50 — The Sufi sermon, beauty as a spiritual calling, and artistic value.
• 05:20 — Introduction to Suburban Paradise and invitation to an aural experiment.
• 06:45 — Soundscapes, observation, and the act of listening as healing.
• 09:15 – 12:10 — Dear Diary: Parental relationships, the “Ta Da List,” and adult status anxiety.
• 16:14 — Audio vignette: Caitlin and her dad celebrate completed tasks.
• 16:58 — Caitlin’s closing monologue: art vs. employment, gratitude, wry self-reflection.

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Tone and Style

The episode is intimate, playful, and deeply self-reflective—filled with wit, vulnerability, and philosophical tangents. Caitlin’s signature narrative voice balances existential weight with levity, especially through moments with her father and the subversive “Ta Da List.”

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Summary

In "Kaitlin Lost Her Ambition," Caitlin Prest offers a raw exploration of losing one’s professional drive and finding solace—and perhaps a more authentic form of meaning—in mundane triumphs, close relationships, and small acts of artistry. Through diary entries, soundscapes, and gentle ribbing with her father, she eloquently questions our obsession with achievement and productivity, instead proposing beauty, attention, and connection as their own quiet forms of fulfillment.

This episode is essential listening for anyone who has ever felt untethered by ambition’s absence or wondered how to navigate a season of inwardness and uncertainty with grace, humor, and heart.

Transcript

[Elizabeth Day]

I'm Elizabeth Day, creator and host of

[Caitlin Prest]

how to Fail, where we hear from

[Elizabeth Day]

people like this for Schitt's Creek, for example. If I had a partner going into that experience, I certainly would not have had that partner coming out of that experience.

[Caitlin Prest]

It's a talent to be a mom,

[Caitlin Prest (Diary Voice)]

you know, it's a skill.

[Elizabeth Day]

And even we actually seen Miranda fail at a lot of things. That was the best thing that could have happened to her.

[Caitlin Prest]

That's how to fail.

[Elizabeth Day]

Find it. Wherever you're listening to this, I'm pretty

[Thumbtack Advertiser]

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[Elizabeth Day]

The last time I saw her, she was late. The Zoom event was well underway. And then there she was, one of the many squares on screen, feet up on desk, lighting a cigarette, blowing O's at this very professional meeting that I'd slipped on my nice sweater for. But she didn't care. There she was, blowing smoke rings and making me giggle so hard a colleague dmed to ask what I was laughing about.

[Caitlin Prest (Diary Voice)]

All right, Yahweh,

[Caitlin Prest (Narration/Reflection)]

There's a crazy rainstorm right now.

[Elizabeth Day]

This is her, the podcast producer who gives zero fucks. Caitlin pressed.

[Caitlin Prest (Narration/Reflection)]

There's another one coming.

[Dad]

Oh,

[Caitlin Prest (Narration/Reflection)]

the lightning is close.

[Caitlin Prest (Diary Voice)]

Oh, what a way to go. That would be.

[Elizabeth Day]

Caitlin Prest is one of the OG art weirdos. In podcasting, she makes the Heart, the critically acclaimed queer feminist show about bodies, gender, power, and the mysterious emotional terrain between people. The Heart is responsible for some of the most intimate, daring audio docs out there. For example, Caitlin's deeply personal series called no. About the complexities of navigating sexual intimacy and desire and communicating boundaries and consent. To state the obvious, the hart has always been ambitious. They win awards, they've been a Peabody finalist. But these days, Caitlin is not pitching large budgets to production companies. She's not holding down a job. She's living with her parents in the suburbs of Ontario, making a quieter kind of radio.

[Caitlin Prest (Narration/Reflection)]

I've been joking that I'm having an existential crisis, but it's not really a joke. I don't believe in the structures of our society anymore. I've lost my ambition. I've lost the desire to excel by the standards of the American entertainment industry. I mean, I'm kind of returning to a very simple, playful, humble offering of what I have right now to offer.

[Elizabeth Day]

Caitlin calls her latest series Suburban Paradise a humble offering, but I gotta say, it's radio that makes me lean in and listen in a way I haven't ever since I sadly got hooked on chatcasts.

[Caitlin Prest (Narration/Reflection)]

There's a Sufi sheikh in Toronto who once did a sermon where he said, how do we call God? You know, we call God God. We call God Allah, we call God Hashem, we call God. What else could we call God? What's a word we could use to call God? What about beauty? He said. And then for the rest of the sermon, instead of saying God, he said beauty. And so I believe that creating things of beauty as an artist is a way of connecting with the divine. And by connecting with the divine and being a channel for the divine, you allow other people to connect with the divine, you know, and so to create beautiful things matters, I believe. I mean, not to say that what I'm making is beautiful, but the. But I guess I'm, you know, I'm trying, I'm striving for that.

[Elizabeth Day]

Dear proxy listeners, today you're in for a treat as the team works on new cases for the fall and tries to get out into the water a bit. Please enjoy this humble playful offering from Caitlin Press to the heart called Suburban Wear, a dice

[Caitlin Prest]

from Mermaid palace and Radiotopia. Welcome to the Heart. I'm Caitlin Prest and this is Suburban Paradise, a somewhat non sequiturly named oxymoronic title for this all new season of the heart. A radio inspired short form segment oriented experimental window into the places that I go, the thoughts that I think and some sound playtime. We begin with sound with listening to the world around me that is now going to be around you. Can you guess where I am?

[Caitlin Prest (Diary Voice)]

Extra pages.

[Caitlin Prest]

Do you know what time of year it is? What time of day? What the weather's like? Observing the sounds around us is a way of tuning in. Julia Cameron says that giving attention is an act of connection. And the reward that we get for that attention for that connection is healing.

[Caitlin Prest (Diary Voice)]

It.

[Caitlin Prest]

Segment 2 Dear Diary, raw writing shared in its most earnest, honest and naked form. This is written on a piece of 8x11 white printer paper typed on a typewriter lent to me by Becky o', Neill, my bestie, who you'll probably hear. Truth be told, even though technically I live in suburban paradise at my parents house in the suburbs of Ottawa From a certain point of view, I kind of also live at Becky Oneills flower farm and studio. You'll be hearing more than one episode recorded in the beautiful stone farmhouse in Roseneath, Ontario, where she and her dog and her ducks and her cats and sometimes me live. The typewriter is a blue royal and the ribbon was very old at the time that I typed this.

[Caitlin Prest (Diary Voice)]

June 10, 2025. Money, money, money money money money, money, money, money, money, money, money. Today dad was a champion of the tada. The day began with a twist on one of his most famous sayings. And when I say one of his most famous sayings, I mean that I grew up hearing this saying basically every day of my childhood to the extent that I measured myself against it.

[Caitlin Prest]

And when I finally gave myself permission

[Caitlin Prest (Diary Voice)]

to do the opposite of it, it was a great step forward in my life. And I believe that maybe there has been some part of me that has waited ever since I was born for the moment that came this morning when I could say to him, now that you work for me, Daddy. We play first and work later. He grumbles a bit after I deliver my twist on his favorite saying, but I know that he's pleased as he goes up the stairs to enjoy our very first break, the one that we start the day with. He was four minutes early for his quote unquote shift. But when we checked in, I did what I always do with everybody who's ever worked with me or for me. I offer lateness a sliding scale start time. I don't say that I need 30 more minutes. I check to see if 30 more minutes is needed in any way by anyone present. And when the other party says that they could really use 30 minutes, I say I could also use 30 minutes. And we agree that we'll meet in 30 minutes. And 40 minutes later we start the day. I start to write a to do list. I tell my dad about the philosophy of the TADA list. And when we get one tiny thing done, I write it down under a heading that says tada. I couldn't have expected or hoped even for how much he took to the concept of the Ta Da list. It was a gift that kept on giving throughout the day. We worked for four hours and now I'm sitting in the backyard writing on Becky's typewriter at a table that I love but I can never find a good reason to sit at. I'm typing these words, Dear God, help me finish my art. Dear God, thank you for my daddy. Excuse me, my ta da di tada.

[Caitlin Prest]

Di,

[Caitlin Prest (Diary Voice)]

without whom I never would have had the strength to persevere through the forgotten passwords and AI menu items, the contact support page labyrinth leading to a phone number. That doesn't work if you're in that doesn't work if you're in America. That doesn't work if you have not updated your password. That doesn't work if your subscription is lapsed, even if you're calling to pay for your lap subscription. I wouldn't have been able to persevere through the quantity of reminders that by standards I didn't think I cared about, I have failed. I have failed to become and to stay an adult. It's strange how adulthood can kick you out of itself. It's a status we're always being threatened we'll lose if we aren't perfect parents, we lose our status as an adult. If we can't pay our bills, we lose our status as an adult. If we move in with our parents who have maintained their status as adults, we most definitely lose our status as adults. I'm not sure what happens to parents of such non adults. I suppose they simultaneously gain status for being adult enough to still act as parents to their adult age children. But maybe internally they lose a little bit of status for having children who never fully made the leap, who seemed like adults for a moment and then fell apart. We lose status for being too emotional. We lose status for having tantrums or crying too much, for not being able to get out of bed. We lose status for being frivolous, unreliable, eating ice cream for dinner. But for some reason we don't lose status for being cruel. We don't lose status for being selfish. We still get to be an adult even if we're boring. I never would have made it through all of the moments that forced such thoughts into my head if it wasn't for Dad. I mean to Daddy. To Daddy and his high fives and great insistence on adding each item. We two step verification style finished together to not the to do list, but the Ta Da list. The list of things we did. He was the username, I was the password, he was the email address and I was the backup mobile phone number. I was the to do list, long and overwhelming and he was the Ta DA list. Enthusiastic stars and multiplying checkmarks, an extra check mark for each thing we did. By the end there were eight check marks beside the thing that we wrote down and the stars he insisted had to get bigger and bigger each time we finished. When the list filled the paper we were using even Though there was far more to do. Even though there was far more to do today, we dad it. P.S. i'm positive that you immediately lose your status as an adult if you as a 38 year old woman in earnest, call your actual dad daddy.

[Caitlin Prest]

Segment 3 raw sound. Not like at the beginning. This is raw sound that I dug up from the time period in which the diary entry takes place.

[Dad]

Ta da. Another one off the list. Let's do it.

[Caitlin Prest (Diary Voice)]

Transfer.

[Dad]

Big fantastic. These are pretty tough ones, you know. So very, very good.

[Caitlin Prest (Narration/Reflection)]

USD.

[Dad]

It's like climbing the mountain.

[Caitlin Prest]

Okay, okay.

[Caitlin Prest (Narration/Reflection)]

And now

[Dad]

be checking the check mark. Making the star bigger star every time. Then more check marks. There we go.

[Thumbtack Advertiser]

Yippee.

[Caitlin Prest (Narration/Reflection)]

Ta da.

[Caitlin Prest]

Please follow CaitlinPrest aitlynprest on Instagram to see pictures and videos, additional content related to the things that you heard in this episode. The Diary that the diary entry came from, a picture of the suburban paradise that I make these episodes from, and other things who knows what. Follow me on Instagram aitlynpress Donate to the Unemployed Philosophers Guild, of which I am a member. All donations to the Unemployed Philosophers Guild made through the links that you find in the show notes go towards this Unemployed philosophers attempts to finish things she started years ago that have long lost their momentum. Donate to the Unemployed Philosophers Guild. Technically, I wouldn't call what I am unemployed. I wouldn't call it fun. Employed. I hate. I really do hate puns. Even though I did a lot of them. I did those for Natalie. Natalie. Look what you've done to me. I guess there's no going back now. I. I do puns. Um, I still think of you every time I make a pun and imagine you laughing and then I cringe and feel sick to my stomach. If you have no idea who Natalie is or what I'm talking about, scroll down the feed and check out sisters. Anyways, okay, I'm gonna stop rambling in the credits now because there's no credits to say. It's just me. That's it. Oh my God, am I turning into one of those podmen? Ew. Don't let it happen. Donate to the Unemployed Philosophers Guild. Even though I don't like calling myself unemployed, this is a very firm choice not exchange my labor for financial compensation as I do commercially non viable art projects that I may never release. Okay, okay. Thanks for listening. See you next month. Radiotopia from PRX.