Episode 65: Debut Memoirist Lu Chekowsky and the Illusions of AdvertisingEpisode 65: Debut Memoirist Lu Chekowsky and the Illusions of Advertising
Creative Sobriety
Emmy-winning creative director and author Lu Chekowsky talks with host Kristen Bear about advertising’s illusions, grief, body image and her eight-year path to a brutally honest memoir. The conversation blends industry behind-the-scenes with a raw look at shame, healing and why life rarely fits into a neat before-and-after arc.
51:43•23 Jul 2026
Selling Illusions, Finding Self: Lu Chekowsky on Advertising, Grief and Body Image
Episode Overview
- Advertising is built on creating a problem you didn’t know you had, then offering the product as the solution.
- Chasing a perfect “after” keeps people stuck in shame and future-tripping instead of dealing with what hurts right now.
- Grief and family dynamics can shape disordered relationships with food, bodies and self-worth in ways that aren’t consciously chosen.
- Bringing shadowy, shame-filled parts of life into the open and speaking about them can reduce their power and support genuine change.
- Creative projects, including memoirs, often take years of drafts, rejections and perspective before they come together in a meaningful way.
“I was always living so far ahead in the future that I couldn't see the billion ways I was hurting myself in the present… I'd had a crappy before, and I wasn't going to be happy until I became a full-fledged after.”
Get ready to be moved by a real-life account of how advertising, grief and body image collide, told through the sharp, funny lens of debut memoirist Lu Chekowsky. This conversation centres on Lu’s memoir, *Don’t Buy What I’m Selling: On Breaking Up with Advertising and Finally Learning To Love My Whole, Fat Self*.
Kristen Bear chats with Lu about life inside top-tier agencies like Wieden+Kennedy, why ads work on us even when we know better, and how a career built on manufacturing fantasy can quietly erode a person’s sense of self.
Lu reads a powerful passage about living in an imagined future while ignoring the pain of the present: “I was always living so far ahead in the future that I couldn't see the billion ways I was hurting myself in the present… I'd had a crappy before, and I wasn't going to be happy until I became a full-fledged after.” It’s a gut punch for anyone who’s ever chased a ‘new you’ through alcohol, diets, relationships or shopping.
You’ll hear how her mother’s early death, fat activism and love of Nike’s “Just Do It” ads drew Lu into advertising, and how that same industry clashed with her body, values and mental health. She talks candidly about using food for comfort, the subconscious pull of grief, and the long, messy process of untangling shame without pretending life has a perfect “after”. For creatives and sober folks alike, the eight-year journey to finishing the book is especially reassuring.
Lu explains the false starts, re-shaped drafts and painful rejections before one editor finally said yes, proving that slowness and self-honesty can still win in a click-chasing culture. If you’re sober, sober-curious, or simply tired of being sold a better version of yourself, this conversation offers sharp humour, hard truths and a gentle reminder that you’re allowed to be a work-in-progress. Which stories about your own body, past and potential might you be ready to rewrite?
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