180. Dream Job, Perfect Life...and Still Feeling Like Something Was Missing. Here's What She Did About It | Conversation with Hillary Dater

Hillary Dater came to a BEST LIFE Retreat a few years ago -- not because she was in crisis, but because her work brought her there. She had what looked like everything: a dream job in the nonprofit sector, family, community, a life that rang all the bells.And still, something wasn't quite right. She just hadn't stopped long enough to notice.What followed the retreat was a series of genuinely bold moves: a move to the mountains, leaving a career she'd spent decades building to pursue something that actually lit her up, a fly fishing trip to Argentina with her son -- her first international travel in thirty years -- and a year spent intentionally, deliberately, scheduling fun back into her life.In this conversation, Hillary and Laurie talk about what it actually looks like to stop living on the sidelines of your own life...even when the life you're living is already pretty good. They talk about joy as something that has to be practiced, not assumed. About asking for help as a skill. About the moment Hillary's father, in hospice, looked at her and said: "I've got all the time. I've got the money to do anything I want. And I don't have my health. Don't make that mistake."This episode is proof that you don't have to be in crisis to deserve change. You just have to decide the life on the other side of the investment is worth more than the comfort of staying put.What we coverHow Hillary came to the BEST LIFE Retreat for work -- not because anything was wrong in her life -- and what happened after she leftThe light fixture epiphany: the moment she realized she couldn't answer the question "what do you like?" and what that revealed about how far she'd drifted from herselfWhy being in a room of women you barely know can be more liberating than being with your closest friendsThe "scared-cited" feeling: what happens when you share a bold idea with the wrong people first...and what happens when you share it with the right onesHow Hillary's dad's final words from hospice changed everything: "I've got all the time and the money, and I don't have my health. Don't make that mistake."The Hardy reel, the screaming line, the fish she stopped counting, and the moment she realized she hadn't known what fun felt like in decadesMoving to the mountains: the guilt, the fear, the grief...and what she found on the other side (her daughter making her breakfast in pajamas)Argentina: fly fishing with her son, thirty years without international travel, and what happens when you know the what and trust the universe with the howThe year she color-coded her calendar to schedule fun — and how 2026 became the year fun stopped being scheduled and started being just who she isAsking for help as a skill: how fly fishing taught her to say "I don't know this, but I want to"...and trust that willing teachers would show upThe belief she'd been carrying that she was difficult and unpleasant to be around — and what the retreat helped her see insteadWhat it means to leave a legacy while you're still here — and why watching mom live her best life is one of the greatest gifts she can give her childrenThe long arm quilting machine, the 55th birthday sand dunes, the riding lawnmower coveralls...and what it means to finally say yes to yourselfQuotable moments"I'm in a great place. I was in a great place, but I'm in an even better place now — and I feel more authentically myself than I ever have in my entire life.""When you're all there for the same purpose, even if everyone's path is different — it just becomes a game changer.""When you've got a dream and you're aligned with it and you're leaning into it, the path opens up for you.""I just had to get really comfortable with being bad, asking a lot of questions, asking for help...none of those things are like me.""I've got all the time. I've got the money to do anything I want. And I don't have my health. Don't make that mistake." — Hillary's father, from hospice"This is fun. This is what fun feels like." — the moment on the river that changed everything"The idea of not taking the risk and always wondering, if I had just let my life pass me by, if I had just remained sitting on the sidelines...that was way more scary than the idea of doing it.""Don't let life put you back on your heels. Lean into it." — Hillary's grandfather"Get in the game. It's never too late to make a change. It's never too late to be your authentic self.""Every time that I've leaned into something, even if it felt a little scary or overly indulgent, the reward and the return on that investment has just paid off in spades.""Every time I see you, I'm living my best life — and I have you to thank for it."Resources + links mentionedDie With Zero by Bill Perkins — referenced in conversationThe BEST LIFE Retreat Book a 15-minute call with LaurieIf this episode moved you, share it with the woman in your life who has a pretty good life — and deserves to know it can be even better. Subscribe, leave a five-star review, and know that Laurie reads every single one.📩 JOIN MY MAILING LISThttps://www.schoolofmidlife.com/newsletter👉 CONNECT WITH LAURIE:📩  Email Laurie 💻 WebsiteOn InstagramOn LinkedInWork with Laurie