113. Parenting Teenagers Without Losing the Relationship, a Conversation with the Teenage Guide, Ashley Chandler

Vicky sits down with Ashley Chandler, founder of The Teenage Guide, for a conversation about the shift every parent faces once their child hits middle school: moving from "boss" to "guide." Ashley draws on nearly two decades in education and coaching, along with her own teenage years in the 90s, to explain why the teen years don't have to be something families just survive. They talk about the real skill behind getting a teenager to listen (hint: it starts with listening to them first), why a mother's identity often goes through its own reconstruction right alongside her teenager's, and how to build a friendship-shaped relationship that lasts long after the kids move out. If you've ever wondered why your once-easy elementary schooler suddenly feels unreachable, or found yourself grieving a version of parenting you're not ready to let go of, this one is for you. What You'll Hear Ashley's path to this work (03:33) — A dual-credentialed educator with 18 years in schools and coaching, Ashley shares what led her to found The Teenage Guide, including her own experience of feeling under-guided as a teenager in the 80s and 90s. From boss to guide (08:04) — The invisible shift that happens around middle school, why parents feel like they're losing control, and what actually changes underneath that feeling. Midlife as adolescence in reverse (12:20) — Ashley's framework for understanding why so many women's mental health dips right as their kids hit adolescence, and why the loss of the "PTA mom" identity deserves more attention than it gets. Redefining self-care and permission (16:00) — Why self-care isn't about bubble baths, and the very Gen X habit of waiting for someone else's permission to rest. The one move that gets a teenager to actually listen (32:14) — Ashley's approach to validating a teen's opinion before offering your own, even when you strongly disagree, and why "you shouldn't believe that" backfires every time. What you actually control as a parent (40:00) — With friend groups and outside influences largely out of a parent's hands, Ashley walks through what's left to work with: how you show up, what you allow in your home, and the example you set. Building perspective and resilience (43:11) — Why exposure to different ways of living matters for teens' emotional intelligence, and Ashley's take on letting kids struggle enough to find out what they're made of. The sandwich generation, reconsidered (50:23) — A conversation about the parents' side of adolescence: aging parents, kids preparing to launch, and the identity work happening for women in midlife at the same time. A generational thread (54:19) — Vicky and Ashley trace the throughline from their grandmothers' limited options to their own "you can be anything" upbringing, and what they hope changes for their daughters' generation. About Ashley Chandler Ashley Chandler is the founder of The Teenage Guide, where she coaches parents to become guides rather than bosses inside their own homes. A dual-credentialed educator with 18 years of experience across public and private education and adult and teen coaching, Ashley blends neuroscience, behavior change, and communication strategy into practical tools for families navigating the middle and high school years. Connect with Ashley: Website: theteenageguide.com Resources Mentioned The Confident Connected Blueprint (Ashley's live class) Have a question about navigating the teen years, or a topic you'd like covered on the podcast? Reach out through Women Mastering Midlife. Let's Keep the Conversation Going If this episode resonated with you, please ra