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

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 cover * How Hillary came to the BEST LIFE Retreat for work -- not because anything was wrong in her life -- and what happened after she left * The 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 herself * Why being in a room of women you barely know can be more liberating than being with your closest friends * The "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 ones * How 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 decades * Moving 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 how * The 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 is * Asking 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 up * The belief she'd been carrying that she was difficult and unpleasant to be around — and what the retreat helped her see instead * What 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 children * The long arm quilting machine, the 55th birthday sand dunes, the riding lawnmower coveralls...and what it means to finally say yes to yourself Quotable 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 mentioned * Die With Zero by Bill Perkins [https://www.amazon.com/Die-Zero-Getting-Your-Money/dp/0358567092/ref=sr_1_1?crid=28S530O5B5X97&dib=eyJ2IjoiMSJ9.HUNGjW6LkGMLKjGS3Fgr56jHfzJDnJRiZFWSXcidqYBjnmjPJI4SqCZFch722X-Xe5ZrvoszTy40KZmCbV50w6uM_JvCODuizpoEfoZaZwqu5bqaJS1fHRmPVBpWr86Tr7EpTSGYyp8YAhQMgqPTKEIgIaZ1TDgLHqLSPy66mxKzx4wlVuCr_wEvjTYK4vupJmkZMUk2jgiFien_xvJ82Vg9FtpmFBa4lupkZOOypkI.ER9j4EXPFSwrMfpPnNqHhkN5JcMKMw_kEd_Jm_vGSEI&dib_tag=se&keywords=Die+with+zero&qid=1782494328&sprefix=die+with+zero%2Caps%2C204&sr=8-1] — referenced in conversation * The BEST LIFE Retreat [https://www.schoolofmidlife.com]  * Book a 15-minute call with Laurie [https://calendly.com/laurie-reynoldson/best-life-mastermind-inquiry] If 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 LIST [https://www.schoolofmidlife.com/the-weekly-best-life-list-sign-u] https://www.schoolofmidlife.com/newsletter [https://www.schoolofmidlife.com/newsletter] 👉 CONNECT WITH LAURIE: 📩  Email Laurie [ laurie@schoolofmidlife.com] 💻 Website [https://www.schoolofmidlife.com] On Instagram [https://www.instagram.com/schoolofmidlife/] On LinkedIn [https://www.linkedin.com/in/laurie-reynoldson-b28b921a/] Work with Laurie [https://www.schoolofmidlife.com/enroll]

179. There Are Only 15 Summer Weekends. Are You Wasting Them...or Ruining Them Trying Not To?

15 weekends of summer. How are you spending them? Laurie counted them. There are 15 summer weekends this year — and the moment she did that, something shifted. Not because it changed anything. Because finite time does something very particular to high-achieving women: it turns enjoyment into management. This episode started as a thought on a walk and became something much bigger: an honest look at busyness as a drug, the habit of earning rest before allowing it, and why the discomfort of doing nothing might be the most useful information you get all summer. Laurie shares what she's been working through in real time: the Sunday she spent doing absolutely nothing while Mike was out of town, the guilt that followed, and the moment a quote from a keynote at Craft + Commerce hit her in the chest and put language to something she'd been feeling her whole life. Practical, honest, and a little uncomfortable in the best way. This one is for any woman who has ever felt like she needed to earn the weekend before she was allowed to enjoy it. What we cover * Why counting the summer weekends changes the way you experience them...and not always for the better * Parkinson's Law: why finite time makes us cram instead of savor, and what that costs us * The two problems with finite time: cramming it full, or feeling guilty for not cramming it full * The pattern Laurie has been running her whole life — Saturdays off, Sundays working — and why she never questioned it until now * The Sunday she did absolutely nothing, felt guilty about it, and what that revealed * Jay Papasan's keynote at Craft + Commerce and the quote that stopped her cold: "If busyness is your drug, rest will feel like stress." — Ian Simpkins * Why busyness works like a drug, and what the cost of that addiction actually is * Busyness as a hiding place: why staying in motion postpones the questions, the decisions, and the version of yourself that has things to deal with * The empty calendar question: if every obligation disappeared tomorrow, what would bubble up for you in the quiet? * Three things Laurie has been doing this summer — imperfectly — to practice actual rest * Why rest is a skill, not a reward * The question underneath all of it: who am I when I'm not busy? The three practices 1. Name it when the pattern shows up. Not out loud, not dramatically. Just notice: I'm reaching for my laptop because I feel like I should have something to show for this afternoon. That's it. See it. 2. Give the guilt somewhere to land. The guilt isn't about the rest. It's about the belief underneath: I'm only as valuable as what I produce. When the guilt arrives, get curious. Ask it: what are you trying to protect me from? What do you think will happen if I just sit here? 3. Start smaller than you think you need to. Not the whole weekend. Twenty minutes. No phone, no task, no optimization. Just twenty minutes with no agenda. Then notice: how long after those twenty minutes does it take before you reach for something to do? Quotable moments "The moment something becomes finite, you stop enjoying it and start managing it." "At some point the weekend becomes a production — and the question becomes, is this still a weekend, or is it just a different kind of work?" "If busyness is your drug, rest will feel like stress." — Ian Simpkins, shared by Jay Papasan at Craft + Commerce "The rest was always conditional. The play was always something I had to earn first." "The discomfort of being unproductive feels worse to me than the exhaustion of being overworked." "Busyness isn't just a habit. It can be a hiding place." "The busyness feels productive. But what it's actually producing is distance...from the questions, from the stillness, from the version of yourself that knows things you're not ready to deal with." "The rest isn't indulgent. It's information." "Rest is a skill. The first few times you try it, it's probably going to feel awful." "Who am I when I'm not busy? That's one of the most important questions a woman in midlife can ask herself." Resources + links mentioned * Last week's episode: Shoot Your Shot — Even When You'd Rather Look Away [https://www.buzzsprout.com/2147326/episodes/19352471] * Apply for the BEST LIFE Mastermind [https://www.schoolofmidlife.com] * Book a 15-minute call [https://calendly.com/laurie-reynoldson/best-life-mastermind-inquiry] with Laurie If this episode resonated, share it with the woman in your life who needs to hear it. And if you haven't already — subscribe, leave a five-star review, and know that Laurie reads every single one. 📩 JOIN MY MAILING LIST [https://www.schoolofmidlife.com/the-weekly-best-life-list-sign-u] https://www.schoolofmidlife.com/newsletter [https://www.schoolofmidlife.com/newsletter] 👉 CONNECT WITH LAURIE: 📩  Email Laurie [ laurie@schoolofmidlife.com] 💻 Website [https://www.schoolofmidlife.com] On Instagram [https://www.instagram.com/schoolofmidlife/] On LinkedIn [https://www.linkedin.com/in/laurie-reynoldson-b28b921a/] Work with Laurie [https://www.schoolofmidlife.com/enroll]

178. The Worst Thing a Leader Can Do, According to a Coach Who's Worked With 1,000 of Them | Conversation with Allison Dunn

Guest: Allison Dunn, Executive Business Coach, Founder of Deliberate Directions, Host of the Deliberate Leaders Podcast, Author of Think First: Stop Being the Bottleneck. Start Building Thinkers. Episode summary Allison Dunn has spent thirty years coaching entrepreneurs and executives — over a thousand of them — and has just written her first book. But this conversation is about so much more than a business framework. Allison's premise: the most capable, most driven leaders eventually become the very bottleneck holding their organizations back. Not because they're failing — because they're succeeding in exactly the way that made them successful in the first place. They keep having the answers. And in doing so, they unintentionally teach everyone around them to stop thinking. Laurie and Allison dig into the five strategic thinking methods in Think First — and why the book reads less like a typical business book and more like a practical manual you'll actually use. But the conversation goes much deeper than the framework. Allison opens up about writing the book in the wake of losing her husband Mark and, shortly after, her mother — and what that loss taught her about legacy, about outgrowing an old version of herself, and about finally clarifying what actually matters now. This one is for anyone leading a team, a family, a household, or just their own life — and tired of being the only one solving every problem. What we cover in this episode * Allison's origin story: getting into a New England prep school at 16, being told no by her parents, and the single question her future father-in-law asked that changed the trajectory of her life * The unlikely, full-circle story of how Allison ended up relaunching Deliberate Directions, the same company originally founded by her late husband's father * Why Allison wrote Think First now, and the personal loss that made the timing undeniable * The core premise: why becoming "the answer person" is the most common — and most dangerous — habit of successful leaders * Method One: Clarify What Matters — why most of us are achieving goals without ever stepping back to ask if they're still the right goals * The difference between addition and multiplication, and why most leaders (and most of us, in life) keep adding instead of finding leverage * The Post-it note on Allison's computer: "Is this urgent or is this important?"  and how that single question changes daily decision-making * Why having all the answers is, in Allison's words, "the worst thing you could possibly have" as a leader * A generational shift in how leaders approach balance, autonomy, and contribution ...and what Gen X is learning from the generation coming up behind them * The identity piece: why letting go of "I have to have all the answers" is so difficult, and what it actually requires * Allison's reflection on outgrowing the version of herself who had a five-year plan with Mark, and what it looks like to rebuild clarity after profound loss * What Mark would say about Think First being out in the world Quotable moments "Could you give it the possibility that you could earn the tuition without your parents?" — the question that changed Allison's life at 16 "Having all the answers is the worst thing you could possibly have" as a leader. "Is this adding or is this multiplying?" "I've outgrown the old version of myself." "Too many people hold onto the version of themselves that someone else expected them to be... as things change, letting those old versions go and getting back on track to clarify what matters." "It's not my job" — on no longer carrying the weight of what other people think. "It's about the journey. And when you have the time, take it." Resources + links mentioned → Think First: Stop Being the Bottleneck. Start Building Thinkers [https://deliberatedirections.com/think-first-allison-dunn/] by Allison Dunn → Deliberate Directions [https://deliberatedirections.com/] → The Deliberate Leaders Podcast — hosted by Allison Dunn, listen on Apple Podcasts [https://podcasts.apple.com/us/podcast/deliberate-leaders-podcast-with-allison-dunn/id1500464675] or Spotify [https://open.spotify.com/show/1fm58tUgAVtryPLoUPNeLC] → Connect with Allison on LinkedIn [https://www.linkedin.com/in/allisondunn/] and on Instagram [https://www.instagram.com/deliberatedirections/] Connect with the School of Midlife → Apply for the BEST LIFE Mastermind [https://www.schooliofmidlife.com/] → Book a 15-minute call with Laurie [https://calendly.com/laurie-reynoldson/best-life-mastermind-inquiry] If this episode resonated, the most meaningful thing you can do is share it with someone who needs to hear it. And if you haven't already, please subscribe, leave a five-star review, and know that Laurie reads every single one. 📩 JOIN MY MAILING LIST [https://www.schoolofmidlife.com/the-weekly-best-life-list-sign-u] https://www.schoolofmidlife.com/newsletter [https://www.schoolofmidlife.com/newsletter] 👉 CONNECT WITH LAURIE: 📩  Email Laurie [ laurie@schoolofmidlife.com] 💻 Website [https://www.schoolofmidlife.com] On Instagram [https://www.instagram.com/schoolofmidlife/] On LinkedIn [https://www.linkedin.com/in/laurie-reynoldson-b28b921a/] Work with Laurie [https://www.schoolofmidlife.com/enroll]

177. It's Time to Shoot Your Shot -- Even When You'd Rather Look Away

Laurie opens this episode mid-story -- crossing a street, spotting someone she admires, and doing what she's done her whole life: looking away. What follows is one of the most personal episodes she's recorded. It's the story of her relationship with Ellen Yin — media company founder, host of the Cubicle to CEO podcast, keynote speaker, and one of the most gracious humans Laurie has encountered in six years of building this business. Across four years and four distinct moments, Laurie traces the evolution from moving chicken around a plate at a lunch table to waking up to a DM that said: Laurie, I adore you. But this episode isn't really about Ellen. It's about the conditioning that makes high-achieving women invisible to themselves -- and what it actually looks like to start unlearning it. At 54. After years of doing this work. Still. The theme woven through this year's Craft + Commerce conference: shoot your shot. Be delusionally confident. Stop being the first person to tell yourself no. This episode is Laurie's honest reckoning with all of it. What we cover * The cold open: crossing the street, recognizing Ellen Yin, and the instinct to look away — and what that one moment reveals about a lifetime of habits * What happened at the lunch table four years ago — the salad, the chicken, the over-explaining, and the classic nervous deflection of proving how much you know when what you're actually feeling is: do I even deserve to be here? * The DM that changed everything: how Laurie shot her shot, flew to Oregon, drove 90 minutes in commuter traffic, and spent an extraordinary day learning from someone she admired * The crosswalk moment — last year's Craft + Commerce — and why she looked away when she could have made the connection herself * This year's conference: walking into the breakout room, the hug, the lit-up face, and what it felt like to be seen by someone she'd assumed was too important, too busy, too far above her to see her * Why the tech not working in the room didn't matter — and the Maya Angelou quote that's been living in Laurie's head ever since * Getting in the photo line — the internal negotiation of "why not me?" — and waking up to Laurie, I adore you * Little Laurie: the conditioning, the beliefs, the habits that were formed so long ago she didn't know she was still running them * "I just stopped being the first person to tell myself no" — the keynote line that reframes everything * The three micro-shots from this year's conference: asking for the free signed book, getting the photo with Ellen, joining a lunch group that felt out of her league * Why it's not the ask that's the problem — it's the belief we've attached to the ask * Four takeaways for shooting your shot, being seen, and doing this work for as long as it takes The four takeaways 1. The look-away is a habit, not a truth. When you feel the impulse to make yourself smaller, to assume someone is too important to see you, to talk yourself out of making the ask — that is old conditioning running a very old program. You can notice it. You don't have to keep obeying it. 2. Shooting your shot is a skill — and it gets easier. Not because the fear goes away, but because you build evidence. The ask doesn't kill you. The worst thing people can say is no — and no is not a rejection of you. It means not right now. You keep asking. At some point, they say yes. 3. The gift of being seen starts with letting yourself be visible. Ellen couldn't have touched Laurie's arm at the crosswalk if Laurie had walked the other way. Every time we make ourselves invisible, we rob someone else of the chance to surprise us. 4. We are never done with this work. At 54. After years of coaching herself and others. Laurie still looked away at the crosswalk last year. Still moved the chicken around the plate four years ago. The difference isn't that the impulse is gone. It's that she notices it faster — and sometimes, not always but more often, does the thing anyway. That's the work. That's all this is. Quotable moments "She made the connection when I wasn't going to do it myself." "I just stopped being the first person to tell myself no." "Being delusionally confident doesn't mean you don't feel the fear. It means you make the ask anyway -- and you let other people decide whether to say yes." "It's not the ask that's the problem. It's the belief we attach to the ask." "Every time we make ourselves invisible, we rob someone else of the chance to surprise us." "The difference between now and four years ago isn't that I've eliminated the impulse. It's that I notice it faster. And sometimes I do the thing anyway." "You shouldn't have to shoot your shot alone." "People will forget what you said. They will forget what you did. But they will never forget how you made them feel." — Maya Angelou "Go make someone feel something this week. Might as well start with yourself." People + resources mentioned * Ellen Yin [https://www.instagram.com/missellenyin/] — founder of Ellen Yin Media, host of the Cubicle to CEO podcast [https://www.instagram.com/cubicletoceo/]  * Craft + Commerce Conference [https://kit.com/conference?campaignid=23939176477&adgroupid=&device=c&placement=&network=x&utm_source=google&utm_medium=ad&utm_content=&utm_term=&utm_campaign=NAM-PMax-Automation&hsa_acc=4935923627&hsa_cam=23939176477&hsa_grp=&hsa_ad=&hsa_src=x&hsa_tgt=&hsa_kw=&hsa_mt=&hsa_net=adwords&hsa_ver=3&gad_source=1&gad_campaignid=23934706481&gbraid=0AAAAADKhItyYqJSnZ9V4gOoc_UGkSpjjB&gclid=CjwKCAjwxb7RBhA5EiwAQ-AAdEelPs4adxF5vKZfqklCVpMNJJmczA1D-44MDRs9GfStej21ybnM-BoCBncQAvD_BwE] — annual creator conference hosted by Kit in Boise, Idaho * Kit [https://kit.com/] — Laurie's new email service provider (formerly ConvertKit)  * James Clear [https://jamesclear.com/] — author of Atomic Habits (30 million copies sold) * Maya Angelou — "People will forget what you said. They will forget what you did. But they will never forget how you made them feel." BEST LIFE Mastermind [https://www.schoolofmidlife.com/] Everything in this episode -- the looking away, the over-explaining, the belief that someone else's question matters more than yours, the feeling that you're not worth remembering -- is exactly the work we do inside the BEST LIFE Mastermind. Not in theory. In practice. With ten women who will see you when you want to make yourself invisible. Who will nudge your arm at the crosswalk when you're about to look away. → Apply now [https://www.schoolofmidlife.com] → Book a 15-minute call with Laurie [https://calendly.com/laurie-reynoldson/best-life-mastermind-inquiry]    Retreat 1 — Sun Valley, Idaho · September 1–4, 2026  Retreat 2 — Civana Wellness Resort + Spa · Carefree, Arizona · February 23–26, 2027 If this episode made you think of someone who needs to hear it , please send it to them. That's your shot to take this week. 🙏 Subscribe, leave a five-star review, and know that Laurie reads every single one 📩 JOIN MY MAILING LIST [https://www.schoolofmidlife.com/the-weekly-best-life-list-sign-u] https://www.schoolofmidlife.com/newsletter [https://www.schoolofmidlife.com/newsletter] 👉 CONNECT WITH LAURIE: 📩  Email Laurie [ laurie@schoolofmidlife.com] 💻 Website [https://www.schoolofmidlife.com] On Instagram [https://www.instagram.com/schoolofmidlife/] On LinkedIn [https://www.linkedin.com/in/laurie-reynoldson-b28b921a/] Work with Laurie [https://www.schoolofmidlife.com/enroll]

176. You Already Know the Answer. So Why Haven't You Made the Decision?

What would you do differently if you actually trusted yourself? Laurie is recording from the mountains this week, which means no studio microphone, slightly different audio, and zero apology about it. Some things you just roll with. What she did bring: a piece of paper with four transformations that become possible when a woman finally stops deferring to everyone else and starts trusting herself. Not the problem; we talk about the problem plenty. Today's episode is about the other side. What actually changes when you do this work. How it feels. What it looks like in your real life and your professional life simultaneously. This one will make you nod. Pay attention to which transformation makes you nod the hardest. Laurie wants to know...and there's an ask at the end about exactly that. What we cover in this episode * The question most midlife women have never been asked -- and why the pause when someone finally asks it tells you everything * Why you're not avoiding decisions because you don't know the answer -- and what you're actually waiting for * The gap between how you make decisions professionally versus personally -- and how personal leadership development closes it * Why the BEST LIFE Mastermind is where this work happens in practice — not in theory * An engagement ask: which of the four transformations resonated most with you? Quotable moments from this episode "The reason you haven't made the decision isn't that you don't know the answer. It's that you don't trust yourself fully to act on it. There's a difference." "You've been trained to trust yourself professionally — and trained to defer personally. Personal leadership development closes that gap." "The guilt often arrives before the desire to do the thing is even fully formed. We shut it down before we can fully feel it." "What you want for your life is not less valid than what you want for your career." "This work gets to the reason why you've been waiting — which is almost never about timing and almost always about fear." "There's a difference between knowing something intellectually and integrating it at a level where it changes your behavior." Resources + links mentioned → Apply for the BEST LIFE Mastermind [https://www.schoolofmidlife.com] → Book a 15-minute call with Laurie  [https://calendly.com/laurie-reynoldson/best-life-mastermind-inquiry] Connect + engage Laurie asks directly: Which of the four transformations resonated most with you? Tag her on social or drop her an email — she's using your answers to shape future episodes. Instagram: @laurie.reynoldson Website: schoolofmidlife.com If this episode landed for you, please subscribe, leave a five-star review, and share it with a woman who needs to hear it. Laurie reads every review personally. 📩 JOIN MY MAILING LIST [https://www.schoolofmidlife.com/the-weekly-best-life-list-sign-u] https://www.schoolofmidlife.com/newsletter [https://www.schoolofmidlife.com/newsletter] 👉 CONNECT WITH LAURIE: 📩  Email Laurie [ laurie@schoolofmidlife.com] 💻 Website [https://www.schoolofmidlife.com] On Instagram [https://www.instagram.com/schoolofmidlife/] On LinkedIn [https://www.linkedin.com/in/laurie-reynoldson-b28b921a/] Work with Laurie [https://www.schoolofmidlife.com/enroll]