Jessi Hempel is many things: an award-winning journalist, podcaster, author, and senior editor-at-large at LinkedIn. But despite her myriad accomplishments, she shies away from labeling herself as ‘successful’. For Jessi, her illustrious career as a technology and business journalist was always a stepping stone on the path to her childhood dream of writing a book. However, after the publication of her memoir, "The Family Outing," Jessi found herself facing an existential quandary: what comes next after you achieve your ultimate goal?In this episode, Jessi takes the helm as we navigate through diverse topics, from the uncertainty of charting a new career trajectory post-success, to the poignant journey of motherhood and the heart-wrenching experience of loss. Together, we delve into the complexities of gender and sexuality, drawing from Jessi's personal narrative, including the remarkable tale of her transgender brother who embarked on a unique journey of pregnancy. Here's what's on the agenda:The challenges women face in defining success and navigating career milestonesWhat to do when you fall out of love with your careerUnpacking societal expectations and pressures surrounding motherhoodThe profound joys and challenges of parenting, including Jessi's unexpected journey into parenthood and coping with lossHow experiences of loss can instill a "f*ck it" attitude, reshaping perspectives on life's brevity, and pursing meaningJessi's journey to writing her memoir and the liberation found in giving yourself permission to explore personal narrativesWhy we need more nuance when it comes to speaking about and understanding gender and sexual identityThe ongoing struggle of asserting boundaries and saying no, even as you ageOUR GUEST: Jessi Hempel, a seasoned tech journalist and host of the acclaimed podcast Hello Monday, serves as senior editor-at-large at LinkedIn. With over two decades of experience, she has crafted compelling features and cover stories on prominent figures and companies in the tech sphere. Previously, Hempel held editorial leadership roles at Backchannel and Wired, and her insights have been featured on major news networks. She is also the esteemed author of The Family Outing, recognized by Time as one of the 100 Must-Read Books of 2022, now available in paperback. Hempel holds degrees from Brown University and U.C. Berkeley, residing in New York City.Want more Jessi? Find her online at https://www.jessijhempel.com/ and listen to her podcast, Hello Monday, at https://podcasts.apple.com/us/podcast/hello-monday-with-jessi-hempel/id1453893304 Follow Jessi on: LinkedIn https://www.linkedin.com/in/jessihempel/ Instagram https://www.instagram.com/jessiwrites/ Want more Hotter Than Ever? Find us and episode transcripts online at www.hotterthaneverpod.com and sign up for our mailing list! Follow us on:Instagram: @hotterthaneverpod TikTok: @hotterthaneverpod Youtube: @hotterthaneverpod Facebook: https://www.facebook.com/profile.php?id=100090728330453 Follow Hotter Than Ever wherever you listen to podcasts so you never miss an episode! We’d love to hear what you think about the show - tell us what stories are resonating with you by writing us a review on Apple Podcasts. Want advice about some aspect of your life over 40? DM us on IG @hotterthaneverpod or text/leave a voicemail on the Hotter Than Ever Hottie Hotline at (323) 844-2303!Mentioned in this episode:Broad CollectiveLearn more about Broad Collective and our membership network for midlife women entrepreneurs at broadcollective.com. Apply to join Broad Collective at https://broad-collective-co.mn.co/landing