Back to school looks nothing like it did when we were kids. Jessica and Kelly compare the back-to-school shopping of their childhoods (the planned outfits, the double socks, the once-a-year wardrobe refresh) with what it looks like now: uniforms, reused backpacks, digital textbooks, and teenagers who carry their entire lives around because nobody uses lockers. Then the conversation gets real. They talk about the mental load of the school year, why middle school is such a big transition, how much of it is really the "noise" around the coursework, and what it means to let your kids figure things out without tying their achievements to your worthiness. If you're a parent trying to be more chill than your instincts allow, this one's for you. In This Episode Back-to-school shopping memories from the '90s, and how different it feels today Why kids' wardrobes, and parents' spending, have changed Reusing supplies instead of replacing everything: Kelly shares reporting that 28% of parents plan to reuse last year's items The financial strain of back-to-school season Why backpacks are the size of a body when lockers go unused The textbook maze: ebooks, physical books, and being "analog learners" Supply lists that never get used (and the supplies kids won't let you remove) Raising kids who follow the rules when you're the "efficiency over rules" type Trying to be "chill" about grades, and where that gets hard Why middle school is a lot: new teachers, hormones, and executive function expectations Planners, calendars, and communication: what helps kids stay on top of assignments Transparency vs. "tricking" students: why knowing what's coming isn't cheating Seeing the teacher's side while still advocating from the parent side Letting go of micromanaging school and keeping the relationship at the center Timestamps (approximate) 00:05 – Welcome and why back to school feels so different now 00:24 – Back-to-school shopping memories: the outfits, the socks, the stirrup pants 02:30 – Today's version: uniforms, one pair of shoes, and teens with opinions on fashion 05:00 – Why is it different? Cost, quality, and where clothes come from 05:39 – Reusing supplies and the financial strain of the season 06:40 – Backpacks, binders, and the no-lockers reality 07:57 – Textbooks, ebooks, and analog learners 10:26 – The supply inventory: "Are you using this?" 12:03 – Rule followers, blending in, and efficiency over rules 13:00 – The grind of the school year and trying to be chill about grades 15:20 – Letting kids navigate it themselves: achievement isn't worthiness 17:40 – The middle school transition and the "noise" around coursework 19:04 – Planners, teacher communication, and executive function 20:23 – Syllabi, transparency, and the "real world" 22:36 – The teacher's perspective and staying curious 23:40 – Letting go of micromanaging, plus what's next Reflection Questions What did back to school mean to you as a kid, and how does that shape the way you approach it as an adult? Where are you doing something out of habit that isn't actually serving you or your family? What would it look like to give the people you love space to figure something out, even when you can see the bumps coming? How do you separate someone else's achievements from your own sense of worth? Freebie of the Month Grab this month's The One Thing worksheet by signing up for the newsletter at chasingbrighter.com. Join the Conversation How are you doing with back to school? Send us a DM on Instagram at @chasingbrighter and tell us what's working, what isn't, and where you're trying to let go. Keywords & Search Terms back to school, back to school stress, back to school shopping, back to school then vs now, parenting middle schoolers, sixth grade transition, middle school parenting, executive function in kids, letting go as a parent, micromanaging school, parenting teens, parenting tweens, mom life, mental load, working moms, sisters podcast, women's podcast, lockers, backpacks, school supplies, reusing school supplies, back to school budget, ebooks vs textbooks, teacher communication, planners and organization, grades and worthiness, achievement and worthiness, raising independent kids, intrinsic motivation, rule followers, 90s nostalgia, Superwoman Diaries, Chasing Brighter, Becoming Not Arriving, personal development for women, self-care, lively living, connection Connect With Us Website: chasingbrighter.com Instagram: @chasingbrighter TikTok: @chasingbrighter Facebook: @chasingbrighter YouTube: @chasingbrighter Newsletter signup: chasingbrighter.com/newsletter