Cruel Summer Book Club

After a health scare at 24, writer, photographer, and artist Tatiana Gallardo decided to spend a year facing all of her fears. So she left the country, quit her job to go freelance, and decided to chronicle all her courageous endeavors in a newsletter called BrazenFace. Host Jillian Anthony (freelancer writer and author of the Cruel Summer Book Club newsletter) asks Tatiana about her experience being a “coward in recovery,” and the two discuss digital nomad life, going alcohol-free, and what it means to live a fearless life. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Tatiana Gallardo: Newsletter: brazenface.substack.com Portfolio: vividtatiana.com Instagram: @vividtatiana Follow host Jillian Anthony: Subscribe to the Cruel Summer Book Club newsletter Website: jilliananthony.com Instagram: @jillathrilla Threads: @jillathrilla Resources mentioned: The War of Art by Steven Pressfield Big Magic by Elizabeth Gilbert The Artist's Way by Julia Cameron Tombow markers Muji fine-tip pens Figma

Can you hear that? It’s your creative routine calling. In this episode, host Jillian Anthony (writer and author of the Cruel Summer Book Club newsletter) talks about swapping the hectic mornings of her former corporate life for a grounding routine that kickstarts her day with creativity. Jillian shares her sacred creative morning routine and how much it’s improved her daily workflow and state of mind. Plus, she teaches you how to find your own ideal creative routine, no matter how busy you are. (And, good news, it doesn’t have to be in the morning.) Learn about keeping a standing meeting with your art, showing up for yourself, and making sustainable commitments to our dreams. Follow Cruel Summer Book Club on https://open.spotify.com/episode/7Mdl0EdgWOAa0ipJwlZz5m?si=TxgLLnXERvu2P7NbdPnvhw&dl_branch=1 and https://podcasts.apple.com/us/podcast/cruel-summer-book-club/id1579533957 now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on https://podcasts.apple.com/us/podcast/cruel-summer-book-club/id1579533957 so we feel the love. Follow host https://www.jilliananthony.com/: Subscribe to the https://cruelsummerbookclub.substack.com/subscribe Website: https://www.jilliananthony.com/Instagram: https://www.instagram.com/jillathrilla/ Threads: https://www.threads.net/@jillathrilla Resources mentioned: https://bookshop.org/a/54715/9780143129257 by Julia Cameron https://1000wordsofsummer.substack.com/ by Jami Attenberg

It's Get Sh*t Done September! Host Jillian Anthony has been a writer for 13 years, and she's gathered a lot of tools and resources along the way. In this episode, she shares her ultimate tech stack, aka all the apps, programs, online communities, financial tools, and more that she uses to stay productive, get her work done, and create her art. Plus, she shares her Sunday routine that helps her organize her weekly tasks, fight off the Sunday Scaries, and get eyes on just how much she accomplishes every week. Resources mentioned: 101 Tools and Resources for FreelancersGet Sh*t Done SeptemberMy writer's tech stack and how I actually get sh*t done Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow host Jillian Anthony: Cruel Summer Book Club newsletterjilliananthony.com@jillathrilla@jillathrilla

It's August, our annual reminder to stop and smell the wildflowers. Host Jillian Anthony (freelance writer and author of the Cruel Summer Book Club newsletter) takes that literally. This is her third summer taking a monthlong sojourn away from her home base of Austin and spending August with friends, family, and nature. Jillian discusses how she has intentionally made August a month to say no to work and yes to travel, beauty, and connection — and how her life as a freelancer made that possible, year after year. This month, her only goal is to exist within the essence of August, the most fleeting month. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love Follow host Jillian Anthony: Subscribe to the Cruel Summer Book Club newsletter Website: jilliananthony.com Instagram: @jillathrilla Threads: @jillathrilla

Comedian Zach Zimmerman knows a lot about success, and even more about rejection. The author of the essay collection Is It Hot in Here (or Am I Suffering for All Eternity for the Sins I Committed on Earth)? shares how he cold-pitched his way into the New Yorker and how he handles unruly audience members as a standup comedian. He and host Jillian Anthony (freelancer writer and author of the Cruel Summer Book Club newsletter) talk about accepting rejection as part of making your art, dealing with difficulty family members, and how they both got broken up with on flights back from Europe. Plus, Zach shares a simple pep talk for pursuing your creative dreams: Nowhere is it written that you can't do it. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Zach Zimmerman: Is It Hot in Here (or Am I Suffering for All Eternity for the Sins I Committed on Earth)?@zzdoublezz@zzdoublezzzach-zimmerman.comzach-zimmerman.com/tour Follow host Jillian Anthony: Cruel Summer Book Club newsletterjilliananthony.com@jillathrilla@jillathrilla Resources mentioned: After MidnightNew Yorker articles Derry GirlsMy Brilliant Friend On WritingBird by BirdThe Bee Sting"Dead Eyes" podcastFocusmate.comSpeechify

A friend gifted host Jillian Anthony (freelance writer and author of the Cruel Summer Book Club newsletter) her first Tarot deck when she was 31 — and it changed her life. Today, it’s her most nourishing personal and creative habit. She shares how Tarot helped her move through heartbreak, get to know her highest self, and tap into her intuition. She explains the basics of Tarot, shares some beginner spreads, and discusses how to start exploring Tarot as a way to connect with yourself and your creativity. Jillian’s favorite part of Tarot is that there is no magic in the deck — the magic is in you. Are you ready to embrace it? Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review — this really helps me reach more listeners! Submit your question on art, life, and love to the Dear Jilla advice column. Follow host Jillian Anthony: Subscribe to the Cruel Summer Book Club newsletter Website: jilliananthony.com Instagram: @jillathrilla Threads: @jillathrilla Resources mentioned: Rider-Waite Tarot deck Mystic Mondays Tarot deck BiddyTarot.com Modern Witch Tarot deck Cat Tarot deck OK Tarot: The Simple Deck for Everyone by Adam J.K. Chani Nicholas astrology app

On the first edition of Dear Jilla, an advice column about art, life, and love, host Jillian Anthony (freelance writer and author of the Cruel Summer Book Club newsletter) answers a reader’s question about overcoming her fear of Cringe. Jillian talks through her own experiences with pushing past Cringe and offers concrete ways to get to know your deepest fears, befriend them, and eventually use them as powerful tools in your creative process. Cringe is about taking risks, embracing who you really are, and reaching your full potential. The Cringe in me sees the Cringe in you. Follow/subscribe to Cruel Summer Book Club now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review — this really helps me reach more listeners! Submit your questions on art, life, and love to the Dear Jilla advice column. Follow host Jillian Anthony: Subscribe to the Cruel Summer Book Club newsletter Website: jilliananthony.com Instagram: @jillathrilla Threads: @jillathrilla Resources mentioned: Kyle Prue’s self-tape The annoying act of telling people what you do by Cody Cook-Parrot A Thing or Two: Cringe Submit your question to Dear Jilla

Host Jillian Anthony (author of the Cruel Summer Book Club newsletter) interviews author and podcast host Madeleine Dore about her many creative pursuits over the past decade. Dore takes us through the winding path of pursuing journalism, interviewing creatives for her newsletter, Extraordinary Routines, then writing her own book, I Didn’t Do the Thing Today. They discuss the tensions between productivity and creativity; the 10-year path to Dore’s first book (and her writing habits); and the importance of accepting your own creative process (and yourself). Plus, they talk about how personal projects can open important doors — even though they sometimes feel like a slog. Dore’s best advice? “Just take the next step, and make it a very small step.” Follow/subscribe to Cruel Summer Book Club now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review — this really helps reach more listeners! Submit your questions on art, life, and love to the Dear Jilla advice column. Follow guest Madeleine Dore: Newsletter: On Things Book: I Didn’t Do the Thing Today Podcast: A Social Life with Friends Follow host Jillian Anthony: Subscribe to the Cruel Summer Book Club newsletter Website: jilliananthony.com Instagram: @jillathrilla Threads: @jillathrilla Resources mentioned: Four Thousand Weeks by Oliver Burkeman Milanote The Artist’s Way by Julia Cameron Women Who Run with the Wolves by Clarissa Pinkola Estés Written Into Being workshop with Giselle Buchanan

The Cruel Summer Book Club podcast is BACK, baby! Host Jillian Anthony talks about the evolution of her thinking around work, money, and success as she’s built a career as a freelance writer and editor since 2020. After reclaiming her creativity for four years, she’s ready to share what she’s learned so far. She discusses the new focus of CSBC — making space for your art and yourself — and what this podcast and the CSBC newsletter will look like moving forward. Plus, she talks about learning to decouple her self-worth from work, cultivating a sense of “enoughness,” and how she’s building her freelance business brick by brick — and reaching for some big artistic dreams. She’s figuring it out and invites you to join her. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review — this really helps me reach more listeners! Submit your question on art, life, and love to the Dear Jilla advice column. Follow host Jillian Anthony: Cruel Summer Book Club newsletterjilliananthony.com@jillathrilla@jillathrilla Resources: Ashleigh Keith Monday Monday newsletter The annoying act of telling people what you do Standing in our values Success on Substack course On asking yourself what kind of artist you want to be Catherine LaSota

On this solo episode, host Jillian Anthony (writer, editor, and author of the Cruel Summer Book Club newsletter) shares her favorite ways to intentionally usher in the new year. She shares her experience with Year Compass, the free workbook she fills out every January, and how it’s helped her make real change — and identify which things she fails to change year after year. She also shares some other New Year resources and talks about her favorite books of 2022. Happy new year! Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Time stamps 1:52 – Jillian’s favorite books of 2022 2:02 – A Heart That Works by Rob Delaney 2:49 – 4000 Weeks by Oliver Burkeman 4:48 – Sober Curious by Ruby Warrington 5:30 – Hear more of Jillian’s sobriety journey on Catherine Andrew’s podcast The Sunday Soother 5:47 – How to use Year Compass to welcome a new year 7:58 – Jillian’s big dreams for the year ahead at the start of 2021 10:32 – How many of those dreams came true 11:02 – Things Jillian hasn’t changed year after year 11:25 – And the things Jillian has changed 13:14 – Picking your word of the year (susannahconway.com) 14:00 – Align your priorities with the Four-Square Model (franhauser.com) 15:28 – Keep track of the best thing that happened during your week for a year 16:09 – Jillian’s bucket list dreams 16:42 – A special New Year’s message for you 17:35 – Where you can find Jillian

Casey Johnston is the author of the long-running column Ask a Swole Woman, which now lives on her newsletter, She’s a Beast. She also wrote a book for beginner strength trainers called Liftoff: Couch to Barbell, which outlines a 12-week program on the basics of lifting, and fosters an online community for women strength trainers (and everyone else who might not fit into the gym bro stereotype). Host Jillian Anthony (writer, editor, and author of the Cruel Summer Book Club newsletter) used Casey’s book as a guide to ease back into lifting after a long break. Casey talks about how strength training changed her relationship to food, exercise, and her own body; why “losing weight” isn’t a great motivator; and how it’s an important life skill to get comfortable with being uncomfortable. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Casey Johnston: Newsletter: shesabeast.co Book: Liftoff: Couch to Barbell Twitter: @caseyjohnston Instagram: @swolewoman Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter

Author Jessica Dore combines the wisdom of ancient storytelling, the mysticism of Tarot, and the teachings of psychology in her book, Tarot for Change: Using the Cards for Self-care, Acceptance, and Growth. A licensed social worker, she writes regular offerings to readers online, using the images of the 78 cards of the Tarot deck and the characters she studies in folklore to weave affecting stories of how we can embrace the archetypes that are ever-present in our own lives — and use Tarot as a tool for change. Host Jillian Anthony (writer, editor, and author of the Cruel Summer Book Club newsletter) talks with Jessica about how she practices Tarot in her own life, how you can start building a relationship with the Tarot cards, and Jillian’s tarot pull about 2022 — a year of big changes. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Jessica Dore: Book: Tarot for Change Offerings newsletter: jessicadore.substack.com Twitter and Instagram: @thejessicadore Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Time stamps 1:14 – Jillian is reading: Desert Oracle by Ken Layne 2:51 – Jillian’s obsession: her new cat Dusty! 4:02 – Introducing guest Jessica Dore 5:00 – Jessica’s obsession: her garden 7:27 – The basics of Tarot 10:04 – How and why Jessica wrote Tarot for Change 12:46 – Jessica’s approach to Tarot as a social worker 21:46 – How Jessica uses Tarot in her own life 28:36 – How to start building a relationship with Tarot cards 30:49 – Jillian’s Tarot practice 33:00 – Jillian discusses her Tarot pull about her year with Jessica 49:35 – Art that helped Jessica through a difficult time: the Visconti Sforza Tarot deck 53:02 – Jessica’s joy bomb: her puppy, and their routine 56:08 – Where you can follow Jessica

What if you approached money from a place of abundance, rather than restriction? Stella Gold will show you the way. Stella is a certified, trauma-informed financial wellness educator — and host Jillian Anthony’s former financial advisor. Their business, My Gold Standard, helps people understand the emotions, experiences, and desires behind how they spend money, and build wealth along the way. Stella’s entire life changed when their father died suddenly, leaving Stella and their mother to sort through the impenetrable financial processes of the government. In this episode, Stella tells Jillian about their own financial education and wealth journey; how grief shaped their future; and what it was like to fully step into their nonbinary identity. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Stella Gold: Instagram: @mygoldstandard Website: mygoldstandard.co Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Time stamps 1:11 – Jillian is reading 4000 Weeks by Oliver Burkeman 3:09 – Jillian’s obsession: Taylor Swift’s “Midnights” 4:52 – Introducing guest Stella Gold 5:54 – Stella’s obsession: eels 8:00 – Stella explains their work as a certified trauma-informed financial wellness educator 11:16 – Financial literacy, and focusing on abundance instead of restriction 15:02 – The impact the sudden death of Stella’s father had on their life 22:22 – Stella’s travel and finances in the midst of grief 28:57 – Stella’s journey to starting their own company 34:34 – What My Gold Standard is all about and Stella’s love for entrepreneurship 37:18 – What it’s like to work with Stella 39:42 – How Stella embraced their nonbinary identity 47:04 – Discovering nonbinary people in Stella’s Filipino ancestry 48:30 – Stella’s they/them pronouns 50:08 – Stella’s finance book recommendations: The Law of Divine Compensation by Marianne Williamson 51:26 – The Sum of Us by Heather McGhee 52:31 – My Grandmother’s Hands by Resmaa Menakem 53:13 – Decolonize Wealth by Edgar Villanueva: “Money is medicine” 53:43 – A piece of art that helped Stella through a hard time: The On Being podcast 56:36 – Stella’s joy bomb: Body movement 59:24 – Where to follow Stella

Nicole Cardoza practices radical imagination, and wants you to as well. She may be best known as the creator of the Anti-Racism Daily newsletter, which began shortly after the murder of George Floyd and now reaches hundreds of thousands of subscribers. But Nicole also manages Reclamation Ventures, which invests in projects committed to health and racial equity; runs the Banned Books Book Club; and is currently on tour as a magician. Host Jillian Anthony (writer, editor, and author of the Cruel Summer Book Club newsletter) asks Nicole what it was like to watch Anti-Racism Daily gain such sudden popularity, and the self-care practices she adopted to see her through an intense professional learning curve. Plus, they discuss closing the “wellness gap;” what it’s like to be a Black, queer, female magician; and Nicole’s pandemic months spent in the wilds of Alaska. Follow Cruel Summer Book Club on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Nicole Cardoza: Website and newsletter: nicoleacordoza.com Instagram and Twitter: @nicoleacardoza Anti-Racism Daily newsletter: antiracismdaily.com Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Time stamps 2:33 – Jillian is reading A Brief History of Time by Stephen Hawking 4:41 – Jillian’s obsession: The Real Housewives of Potomac 6:34 – Introducing guest Nicole Cardoza 7:11 – Nicole’s obsession with radical imagination 9:45 – Nicole’s fall tour as a magician 11:13 – Being a good community member in Austin, a blue dot in a red state 13:30 – Nicole’s upbringing and early interest in magic 15:53 – Nicole’s growth in yoga and the wellness space 17:45 – What is the “wellness gap?” 20:44 – The beginning of Anti-Racism Daily and its growth 26:52 – How Nicole leveled up professionally 32:10 – How Nicole continually educates herself about social issues 35:18 – Nicole’s mental and physical wellness practices 37:28 – Nicole spent months in Alaska during the pandemic 41:01 – Breaking down Nicole’s other businesses 42:10 – Nicole’s goals for Reclamation Ventures and as a performer 44:14 – Nicole’s experience as a Black, queer, female magician 46:46 – Banned Books Book Club, and the rise of book banning in the USA 52:22 – Nicole’s art: “I Found My Smile Again” by Jaylen Pigford 53:48 – Nicole’s joy bomb: Morning walks with her dog to get coffee 55:42 – Where to follow Nicole’s work

Writer, actor, and podcast host Dylan Marron has made a career out of doing something few of us will ever do: talking to internet strangers who said unkind things to him online. When Dylan began publishing video series to a large online audience, he started taking screenshots of the hateful comments people left and saved them in a “hate folder” on his computer. One Facebook chat with an 18-year-old commenter led to the remarkable first episode of his podcast, Conversations with People Who Hate Me, and his first book of the same name. Host Jillian Anthony (author of the Cruel Summer Book Club newsletter and former Editor of Time Out New York) talks with Dylan about how these difficult conversations changed how he exists online and in real life, and how kindness and empathy can radically change how we interact with those who disagree with us. Plus they discuss what it was like for Dylan to take 13 months off social media, how he finally got his book over the finish line after a two-year delay, and how author Anne Lamott’s advice to write a “sh*tty first draft” makes him a better writer. Follow guest Dylan Marron: Website: dylanmarron.com Instagram: @dylanmarron Twitter: @dylanmarron Book: Conversations with People Who Hate Me Podcast: Conversations with People Who Hate Me Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Time stamps 1:08 – Reading Into Thin Air by Jon Krakaeur 5:23 – Jillian’s obsession with Nimsdai 7:41 – Introducing guest Dylan Marron 8:27 – Dylan’s obsession with car detailing videos from @thedetailgeek 10:47 – How Jillian knows Dylan and his husband Todd 16:20 – Dylan’s early theater experience with the New York Neo Futurists 19:02 – More on Dylan’s work and video series at Seriously.tv 22:42 – When Dylan began collecting hateful comments from online strangers 25:31 – What it was like to talk to Dylan’s first guest for Conversations with People Who Hate Me 31:15 – Why Dylan doesn’t describe internet detractors as trolls 36:42 – What “empathy is not endorsement” means 40:34 – How Dylan has reshaped how he exists online 44:04 – Kindness and empathy won’t heal what ails us, but they will help 46:55 – Dylan took 13 months off social media to write his book 49:31 – How being offline for over a year reshaped Dylan’s relationship to social media 53:48 – Dylan talks about missing his book deadline by two years, and the writing process 55:33 – Bird by Bird by Anne Lamott and the freedom of the “sh*tty first draft” 1:03:46 – Two books that helped Dylan write: Bird by Bird by Anne Lamott and Writing Down the Bones by Natalie Goldberg 1:05:35 – Dylan’s joy bomb: taking a nap 1:07:07 – Where you can follow Dylan

Figuring out who to vote for, where and when to donate, and why it all matters can be so confusing. Democratic political strategist Brian Derrick wants to help change that. You may know him from Instagram, where he demystifies upcoming political races and shares how you can actually make a difference, either with donations or through actions. Last year he founded Oath, a site that helps Democrats know which candidate to donate to, and when, so that their dollars will make the most impact. Host Jillian Anthony (freelance writer and editor, and the former Editor of Time Out New York) asks Brian all of her burning political questions, including: When is the best time to make a political donation? What is rage-donating? Why is it important to call members of Congress? What do Democrats need to know and do to influence real change in our nation? And does my vote actually matter? Listen and learn! Follow and subscribe on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Brian Derrick: Instagram: @brianderrick_ Oath Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Time stamps: 1:12 – Reading Fun Home by Alison Bechdel 3:05 – Obsessed with cool fall morning air 5:01 – Introducing guest Brian Derrick 5:51 – Brian’s obsessed with Survivor 10:22 – How Brian got into politics on social media 13:39 – Brian’s goal to help people effectively donate to causes and politicians 14:20 – Brian’s career development 19:37 – Founding Oath to help people make greater impacts 22:40 – Rage funding, and why it often doesn’t make sense 28:12 – Why do donations matter? 28:33 – Why you should invest early in the cycle 34:08 – Why is voter turnout so low for local elections? And why are they important? 38:58 – Can you name your local politicians? 41:17 – Why is it important to call members of Congress? Does it actually make a difference? 47:18 – What Brian has to say to people who don’t think their votes matter 50:32 – Why Republicans are winning the long game, and why Democrats need to play the same game 52:14 – Brian’s love of Broadway and Falsettos 55:08 – Brian’s joy bomb of getting out of the city, and watching bloopers from Veep and Parks and Recreation 57:23– Where to follow Brian

Tiffany Philippou (author of the newsletter The Tiff Weekly) joins the podcast all the way from the United Kingdom. Tiffany’s first book, the memoir Totally Fine (and Other Lies I’ve Told Myself), chronicles the tumultuous decade she experienced after her university boyfriend died by suicide when Tiffany was 20 years old. She and host Jillian Anthony (author of the Cruel Summer Book Club newsletter and former Editor of Time Out New York) discuss stuffing grief down, the long process of healing through writing (and therapy), and how much cultural discussions around mental health care have changed since we were in school. Tiffany also shares how she didn’t start writing for work or pleasure until she was almost 30—one writing class gave her the idea for her book, and she was a published author just a few years later. Subscribe and follow the CSBC podcast so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Tiffany Philippou: Instagram: @tiffphilippou Twitter: @tiffphilippou Buy Totally Fine (and Other Lies I’ve Told myself) Subscribe to The Tiff Weekly Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Time stamps :37 – Reading The Lost Daughter by Elena Ferrante 3:17 – Obsessing over my local Buy Nothing group 5:24 – Introducing guest Tiffany Philippou 8:02 – Tiffany’s obsession: reading books on writing by writers 12:04 – How Tiffany became a writer at 30 18:18 – How a writing workshop sparked her first book 21:11 – Tiffany’s boyfriend’s death by suicide, and coping with grief 25:09 – How trauma affected Tiffany’s memories 27:53 – Writing through shame and forgiving her younger self 31:35 – How cultural attitudes about mental health have changed in the past 10+ years 35:00 – Tiffany’s shifting relationship with alcohol, and the cultural place of booze in the UK 39:13 – Jillian’s shifting relationship to alcohol and being sober curious 40:47 – Tiffany’s romantic relationships 43:36 – Loving people through fear 48:40 – Tiffany’s love of the TV show Friends 50:44 – Tiffany’s joy bomb of hot yoga 54:06 – Where to follow Tiffany

Writer Samantha Stallard (and Jillian’s bestie) returns to the pod! She and host Jillian Anthony (author of the Cruel Summer Book Club newsletter and the former Editor of Time Out New York) discuss the complications of friendships between heterosexual men and women, and what it’s like to date as a woman in your 30s who doesn’t want to get married or have kids. Plus, Samantha talks about the power of self-parenting, the joy of moving back to New York City after two difficult years away, and the comfort of the rare friendships that feel like family. (And don’t forget to check out Samantha’s episode from season one, where she discusses when she broke off an engagement and left New York, and the healing process that followed.) Subscribe and follow the CSBC podcast so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow guest Samantha Stallard: Twitter: @SJStallard Website: https://www.samanthajstallard.com Follow host Jillian Anthony: Twitter: @jillathrilla Instagram: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter: https://cruelsummerbookclub.substack.com/subscribe Time stamps: 2:00 – Discussing Emily Ratajkowski's My Body 7:10 – Discussing The People We Meet on Vacation by Emily Henry 9:43 – Can men and women be friends? 12:45 – Dating with friendship in mind 17:00 – Friendship breakup with a male friend 20:48 – Sam’s big breakup, and returning to New York City 25:37 – Traveling to Italy together and taking five weeks off work 29:05 – Looking out for your future self and self-parenting 29:57 – Practicing thought control and living in the present 36:26 – Samantha meets her future self 39:32 – Dating as a women in her 30s who doesn’t want marriage or kids 46:11 – Dating when you don’t want to be in a relationship 49:06 – Why we need to give women more space to have choices in their lives 53:00 – The challenges of making friends as an adult 57:12 – The Artist’s Way by Julia Cameron 1:02:30 – Where to follow Samantha Transcript link: https://cruelsummerbookclub.substack.com/p/transcript-samantha-stallard-asks

Host Jillian Anthony (author of the Cruel Summer Book Club newsletter and former Editor of Time Out New York) ushers in the second season of the podcast with a solo episode. She discusses the three biggest changes in her life over the past year: 1. She deprioritized work, while building a freelance writing and editing career. 2. She spent the first 167 days of the year sober. 3. She felt the heavy impact of changes in her friendships and social circles. Follow host Jillian Anthony: Twitter: @jillathrilla Instagram: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter: https://cruelsummerbookclub.substack.com/subscribe Time stamps 1:10 – Guest lineup and what you can expect this season 3:32 – Three big changes for Jillian this year 4:01 – Deprioritizing work 5:38 – Imagining what a new work life could look like 6:17 – Resources that helped Jillian reprioritize 8:16 – Forming a freelance life 11:21 – Planning a month off in Europe 13:57 – Gifts of freelance life 16:10 – Exploring long term sobriety 16:53 – Jillian’s discomfort with her relationship to alcohol 20:00 – Choosing 100 days of sobriety 20:29 – What is sober curious? 21:50 – What Jillian learned through sobriety 25:27 – Changing friendships 25:49 – How many friends can you have? 29:20 – Write a Friendship Circle 31:15 – Intentional plans for fall 32:53 – Outro Subscribe and follow the CSBC podcast so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Resources: Life coach Catherine Andrews: https://www.catherinedandrews.com The Artist’s Way by Julia Cameron: https://juliacameronlive.com Fran Hauser’s Four-Square Model: https://www.franhauser.com/blog/my-secret-tool-to-setting-boundaries YearCompass: https://yearcompass.com Sober Curious by Ruby Warrington: http://www.rubywarrington.com/books/sober-curious The Sober Curious Reset by Ruby Warrington: http://www.rubywarrington.com/books/sober-curious-reset Friends: Understanding the Power of Our Most Important Relationships by Robin Dunbar: https://bookshop.org/books/friends-understanding-the-power-of-our-most-important-relationships-9780349143576/9781408711736 Robin Dunbar’s Friendship Circle Transcript link: https://cruelsummerbookclub.substack.com/p/transcript-a-year-of-big-changes

Artist and author Adam J. Kurtz was supposed to turn in the manuscript for his fourth book in April 2020. Instead, he and his husband weathered the worst of the pandemic in Brooklyn, and as most of Adam’s creative work disappeared, he was forced to transform. Host Jillian Anthony (author of the Cruel Summer Book Club newsletter and former Editor of Time Out New York) talks with Adam about his upcoming book of essays and art, You Are Here (For Now), about facing mortality with as much joy and creativity as you can. And Adam discusses leaving New York behind to move in with his in-laws in Honolulu; the importance of having a “F*ck Off Fund”; and the simple fact that we are all artists. Subscribe on Spotify and Apple Podcasts now so you never miss an episode. And don’t forget to give Cruel Summer Book Club a five-star review on Apple Podcasts so we feel the love. Follow host Jillian Anthony: Instagram: @jillathrilla Twitter: @jillathrilla Subscribe to the Cruel Summer Book Club newsletter Follow guest Adam J. Kurtz: Order You Are Here (For Now) Shop all his products at adamjk.com Instagram, Twitter, Tik Tok: @adamjk