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

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]

175. Fewer Years Ahead Than Behind: A Radical Wake-Up Call for High-Achieving Women

Time to do something just for you. When is the last time you made a decision, chose a direction, or said "yes" to something that was entirely, completely just for you? Not for your family, not for your career advancement, and not because it fulfilled a decades-old obligation—but purely for yourself?  In this powerful episode, host Laurie Reynoldson challenges high-achieving women to step off the hamster wheel of external validation and confront a heavy midlife reality. If your life looks completely perfect on paper, yet you are still quietly asking, "Is this it?", Laurie reframes this unsettling question not as a crisis, but as a sign that you are finally paying attention.  This episode marks the official opening of applications for the Best Life Mastermind, a carefully crafted nine-month experience designed to help you stop performing, start living as one unified woman, and figure out what's next for you. In this episode, you’ll learn: * The High-Achiever’s Blindspot: How we unconsciously tie our self-worth to childhood patterns of performance and external approval.  * The "One Identity" Philosophy: Why trying to shape-shift into different people for your career, family, and community leads to bone-deep burnout.  * The Nine-Month Metaphor: Why real personal transformation cannot happen in a 30-day sprint or a 90-day quarter, and why it takes nine months to "birth" a completely new version of yourself.  * The Power of Group Hot Seats: Why listening to other accomplished women untangle their roadblocks serves as your ultimate personal board of directors.  * Bypassing the No. 1 Deathbed Regret: Confronting the reality that there are fewer years ahead than behind, and how to find the courage to live a life true to yourself right now.  The Big Takeaway: Stop waiting for a "perfect time" or postponing your life until retirement or an empty nest. We are no longer relegating the most important work of our lives to left-over weekend hours or late nights after everyone else is asleep.  Inside the Best Life Mastermind Container Applications are officially open for the founding cohort launching this September. This premium, intimate nine-month personal leadership experience is capped at just 10 women.  * Two Mid-Week Luxury Retreats: Immersive, all-inclusive, high-end intensives running Tuesday through Friday so you don't sacrifice your weekends.  * Sun Valley, Idaho (September): Focused on identity and core vision casting.  * Civana Wellness Resort & Spa, Arizona (February): Diving into boundaries, limiting beliefs, and roadblocks.  * Monthly Personal Leadership Calls: Two hours of real-time Q&A, group alignment, and dedicated deep-dive hot-seat coaching.  * A Private, Off-Social-Media Hub: A distraction-free, algorithm-free community platform built for genuine support and connection away from the digital noise.  Ready to claim your spot? Founding cohort members receive the highest level of direct access to Laurie at the lowest investment level the program will ever offer.  * Apply Now [https://www.schoolofmidlife.com] * Book a Call [https://calendly.com/laurie-reynoldson/best-life-mastermind-inquiry] Got questions? Secure a direct 15-minute alignment call with Laurie via the link in the show notes.  * Learn More [https://www.schoolofmidlife.com/] 📩 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]

174. Who Am I Now? The Silent Identity Crisis of Midlife Women During Graduation Season

The guilt that so many midlife women feel during graduation season It is officially graduation season! Across the country, high-achieving women are hosting big open houses, packing up dorm rooms, and celebrating incredible milestones. But beneath the festive surface and the proud smiles, many mothers are quietly navigating a profound, silent struggle: the bittersweet realization that their kids are moving on, and they are being left behind. In this deeply empathetic episode, Laurie Reynoldson shines a light on the hidden identity shift that graduation season triggers. When your primary job for the last 18 to 25 years has been mothering on a 24/7 basis, what happens to your sense of self-worth when those small humans no longer depend on you for their daily survival? This episode is a gentle permission slip to stop suffering in silence, acknowledge the grief of an ending chapter, and start looking at midlife not as a crisis, but as a beautiful, much-needed reset. In this episode, you’ll learn: * The Motherhood Paradox: The ultimate goal of parenting is to raise a human who doesn’t need you anymore—but actually reaching that milestone can leave you feeling completely untethered. * The "Grown and Flown" Reality Check: Why it’s normal to feel an overwhelming mix of intense excitement for your child and deep anxiety about the blank canvas of your own future. * The Pancake Marriage Concept: A candid look at the transitions of midlife relationships, why we settle, and why your tastes in partnerships change as you mature. * Redefining Midlife as a Season: Why midlife isn't a chronological number; it is a psychological phase that can trigger in your 30s when the choices of your 18-year-old self no longer fit the woman you are today. * Stepping Into Phase Two: How to transition into the next phase of motherhood without guilt, putting your own wild and precious dreams front and center. The Big Takeaway: You’ve spent decades doing the heavy lifting of keeping small humans alive. They are successfully launched. Now, it’s your turn to figure out who you are when you aren't first and foremost someone's mother. This second half of your life matters just as much. Special Announcement: The BEST LIFE™ Mastermind If you are standing on the precipice of this massive identity shift and wondering "What's next for me?", you do not have to figure it out alone. This September, Laurie is launching the BEST LIFE Mastermind, a nine-month personal leadership experience for high-achieving women ready to launch their own next chapter. * Intimate Community: Capped at just 10 women to serve as your personal board of directors. * Two In-Person Luxury Retreats: Immersive, soul-searching getaways in Sun Valley (September) and Arizona (February) to cast your vision and anchor your goals. * Continuous Structural Support: Monthly group hot-seat coaching sessions to keep you on the course you set for yourself when daily life tries to pull you back into old routines. * Applications Open June 1st: The waitlist is active now and waitlist members receive first-priority access. Get on the waitlist! [https://www.schoolofmidlife.com/mastermind-list] 📩 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]