307. The Hidden Cost of Being Great at Your Job | Billy Keels

307. The Hidden Cost of Being Great at Your Job | Billy Keels

Are you getting on planes you don't actually need to be on? It is easy to confuse your corporate role with your personal identity, especially when you are a high performer consistently hitting the president's club. But what is the hidden cost of chasing that next title, bigger team, or salary increase? In this episode of The Learn-It-All™ Podcast, Damon sits down with Strategic Advisor, Author, and Top-Ranked Podcast Host Billy Keels to discuss what happens when your identity gets completely wrapped up in your corporate lifestyle. Billy shares his personal wake-up call from October 2012, when he found himself boarding a flight for an executive meeting in Germany on his son's third birthday, physically feeling sick because he was far away from the people he wanted to be with. He dives deep into the corporate "busy-ness" that keeps high achievers frantic and explains why every corporate relationship eventually ends. If you are a high-earning corporate executive trying to figure out how to stop being just a corporate number, manage the chaos of a side business, and gain control of your calendar, this conversation provides a strategic roadmap to designing a life where your job becomes completely optional. 📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5 [https://dl.bookfunnel.com/3ingcx2pp5] In this episode, you’ll learn... 1. Why Billy’s flight on his son’s third birthday exposed the hidden cost of tying your identity to your corporate role 2. How high performers can separate their title from their values before the next promotion, paycheck, or business trip starts making decisions for them 3. Why “spending time” with family is not the same as “investing time,” and how intentional presence changes the way leaders show up at home 4. How to calculate your optionality number so your job becomes a choice instead of a financial dependency 5. Why every corporate relationship eventually ends, and how to build a backstop before layoffs, leadership changes, or personal crises force your hand 6. How Billy helps executives reclaim time, structure a side business, and stay successful at work without sacrificing the life they say matters most Timestamps * 00:00 - Introduction * 00:53 - The birthday flight that changed Billy’s life * 02:27 - When the plane took off and his heart sank * 06:21 - Why high achievers keep choosing the job * 07:32 - When your title becomes who you are * 10:15 - The three-part clarity framework * 11:47 - Spending time vs. investing time * 13:28 - Finding your optionality number * 19:09 - Why high achievers struggle to ask for help * 20:41 - The scary part of finally opening up * 23:38 - Moving out of victim mentality * 26:57 - Are you just a corporate number? * 29:35 - Why companies protect themselves first * 31:57 - How to build optionality while keeping your paycheck * 34:34 - Do you really need to work those extra 15 hours? * 36:21 - The path to making your role optional * 37:26 - What money is actually for * 39:00 - What truly high performers have in common * 41:46 - Why successful executives reach out for help * 43:14 - When a high income still does not feel like freedom * 48:46 - How to define what “being present” actually means * 50:55 - When real change starts to show up * 54:34 - The two types of executives Billy helps most * 56:45 - Why podcasting can change your life and brand * 01:00:16 - How podcasting built Billy’s confidence and network * 01:04:21 - The fatherhood practice Billy is most proud of * 01:06:08 - Where to connect with Billy * 01:08:02 - Damon’s challenge: Are you getting on planes you do not need to be on? About Billy Keels Billy Keels is a national best-selling author, host of the top 1.5% globally ranked “Going Long Podcast”, and expert/go-to executive coach for enterprise-level executives around the world. Based in Barcelona, Spain, Billy is an international speaker and elite advisor to ambitious C-level leaders looking to maximize their positions and opportunities while maintaining their existing career security and stability. Billy is on a mission to help high earning executives multiply their options for the future. Resources and Mentions Billy Keels’ website: https://www.billykeels.com/ [https://www.billykeels.com/] Billy Keels’ LinkedIn: https://www.linkedin.com/in/billykeels/ [https://www.linkedin.com/in/billykeels/] The Going Long Podcast: https://www.billykeels.com/podcast [https://www.billykeels.com/podcast] The Pathway to Optionality: https://www.makeitoptional.com/ [https://www.makeitoptional.com/] Podcast Contact Information: Website: www.learnit.com [http://www.learnit.com] Email: podcast@learnit.com [podcast@learnit.com] Subscribe to the Learn-It-All Podcast: Youtube [https://www.youtube.com/@TheLearnItAllPodcast] I Apple [https://podcasts.apple.com/us/podcast/the-learn-it-all-podcast/id1714645917] I Spotify [https://open.spotify.com/show/1nEHAEkgsTdZvNOTzRk7hZ] Follow Damon Lembi: Linkedin [https://www.linkedin.com/in/damonlembi/] I Instagram [https://www.instagram.com/damonlembi/] I Facebook [https://www.facebook.com/damon.lembi] I X [https://x.com/damonlembi]

306. He Studied Baseball For 30 Years. Here's What It Taught Him About Leadership. | Ken Davidoff

Are you ready to transform your failures into your greatest competitive advantage? In the high-stakes world of Major League Baseball, even the best players fail seven out of ten times. In this episode, Damon sits down with 30-year veteran sports journalist Ken Davidoff to discuss how the resilience learned on the diamond can be the ultimate blueprint for success in the boardroom and at home. Drawing from his book, 101 Lessons from the Dugout, Ken shares powerful stories of Hall of Famers and everyday leaders who mastered the art of "tagging up", pausing to control reactions before they spiral. Whether you are a first-time manager struggling with a "rough outing" or a parent trying to help your child navigate the pressures of youth sports, this conversation offers actionable strategies on building trust through "small ball," prioritizing under pressure with "fielder’s choice" logic, and leading with the authenticity of a World Series manager. Stop playing "not to lose" and start learning how to pace yourself through the grind of any season. 📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5 [https://dl.bookfunnel.com/3ingcx2pp5] In this episode, you’ll learn... 1. Why accepting failure, digesting it, and moving on is a prerequisite for both professional growth and mental strength. 2. Why taking a literal three-second pause before reacting to a frustrating email or a spilled glass of juice can prevent "volcano" moments and preserve your relationships. 3. Why you shouldn't always "swing for the fences" early on; instead, focus on being consistent, meeting people, and building a foundation of trust that allows you to take bigger risks later. 4. A simple mental framework for deciding where to "step on the gas" when your to-do list is overflowing or your child is struggling with multiple subjects. 5. Why the most revered leaders are defined not by their "scorecard" stats, but by their authenticity, curiosity, and how they treat everyone from the janitor to the CEO. 6. Why taking pride in your space and "cleaning up your own messes", literal or metaphorical, sets a standard that transcends winning or losing. Timestamps * 0:00 - Introduction * 1:16 - Baseball’s brutal lesson about failure * 2:31 - The dropped catch nobody forgot * 4:23 - What leaders can learn from a bad outing * 5:34 - When parents make youth sports harder * 6:22 - How 101 Lessons from the Dugout began * 8:50 - The hidden power of the on-deck circle * 12:29 - What kids learn when they sit on the bench * 14:43 - The Little League catch Ken still remembers * 16:48 - The baseball rule that can stop your anger * 19:43 - Why “small ball” built Ken’s career * 21:49 - How one quiet story earned years of trust * 24:55 - How to repair a damaged relationship * 27:36 - David Wright’s lesson for struggling kids * 29:37 - The World Series moment that proved chapter 92 * 32:13 - Why Don Mattingly is remembered without a ring * 34:54 - The lesson Ken wishes made the book * 37:39 - How fielder’s choice teaches priorities * 41:00 - What great managers do differently * 43:41 - The two lessons Ken hopes families actually use * 44:15 - How parents can stop chasing wins through their kids * 46:05 - Damon’s final challenge for coaches, parents, and leaders About Ken Davidoff Ken Davidoff is a renowned sports journalist who spent 30 years covering Major League Baseball for major outlets, including the New York Post. Throughout his career, he has interviewed thousands of players, managers, and agents, covering legendary teams and historic World Series matchups. Ken is currently an adjunct professor of journalism at a college in Massachusetts. He is the co-author of 101 Lessons from the Dugout: What Baseball and Softball Can Teach Us About the Game of Life, a book that translates the timeless wisdom of baseball and softball into life lessons for parents, children, and professionals. Resources and Mentions 101 Lessons from the Dugout book: https://www.amazon.com/101-Lessons-Dugout-Baseball-Softball/dp/B0F7H3553S [https://www.amazon.com/101-Lessons-Dugout-Baseball-Softball/dp/B0F7H3553S] Ken Davidoff’s LinkedIn: https://www.linkedin.com/in/ken-davidoff-220b7a4/ [https://www.linkedin.com/in/ken-davidoff-220b7a4/] Ken Davidoff’s Instagram: https://www.instagram.com/kendavidoff/ [https://www.instagram.com/kendavidoff/] Podcast Contact Information: Website: www.learnit.com [http://www.learnit.com] Email: podcast@learnit.com [podcast@learnit.com] Subscribe to the Learn-It-All Podcast: Youtube [https://www.youtube.com/@TheLearnItAllPodcast] I Apple [https://podcasts.apple.com/us/podcast/the-learn-it-all-podcast/id1714645917] I Spotify [https://open.spotify.com/show/1nEHAEkgsTdZvNOTzRk7hZ] Follow Damon Lembi: Linkedin [https://www.linkedin.com/in/damonlembi/] I Instagram [https://www.instagram.com/damonlembi/] I Facebook [https://www.facebook.com/damon.lembi] I X [https://x.com/damonlembi]

305. "I Didn't Think I Was a Leader" — Then He Captained the All Blacks 52 Times | Kieran Read

What if the secret to elite leadership isn't a natural-born talent, but a learned skill forged through vulnerability and connection? Many emerging leaders struggle with imposter syndrome, questioning if they are "good enough" to lead more experienced peers or step into high-pressure roles. In this episode of The Learn-It-All™ Podcast, Damon sits down with Kieran Read, former captain of the legendary New Zealand All Blacks, to discuss the transition from high-performing individual contributor to world-class leader. Kieran reveals why the most impactful leaders lead through authentic action rather than "big speeches," how to build trust by initiating care and connection first, and the importance of having the courage to be "uncomfortable" to achieve true growth. Whether you are a first-time manager or a senior director, Kieran’s insights on "horizontal leadership" and empowering those around you will help you develop the confidence to lead your team toward excellence. 📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5 [https://dl.bookfunnel.com/3ingcx2pp5] In this episode, you’ll learn... 1. Why trying to emulate a "movie version" of a leader often fails, and how sticking to your personal values and personality builds more trust and connection with your team. 2. How to build a foundation of care and connection through simple daily interactions like sitting with someone new at lunch, before attempting to hold people to high levels of accountability. 3. Strategies for young leaders to gain respect from senior team members by utilizing their expertise and focusing on owning your specific role rather than trying to do everything yourself. 4. Why a leader must "flip a switch" from disappointment back to work to best prepare their team for the next challenge. 5. Why the number one job of a coach or leader is to build a team member's confidence until they are ready to believe in their own "invincibility". Timestamps * 0:00 - Introduction * 1:17 - The dream Kieran Read never thought was realistic * 2:52 - When a coach sees the leader before you do * 4:50 - The first thing new leaders should figure out * 7:33 - How to lead people older and more experienced than you * 9:11 - The leadership mistake TV teaches you to make * 10:25 - The loss that taught Kieran he was trying too hard * 11:47 - Why the best teams don’t depend on one leader * 13:28 - The phone call every New Zealand kid dreams of * 15:04 - Walking into a locker room full of legends * 20:03 - What to do when your ego gets bruised * 21:39 - What Richie McCaw quietly taught about leadership * 25:13 - Taking over after a legend without copying him * 27:38 - Why leaders need to connect before they correct * 30:26 - The hidden weight of leading under pressure * 32:12 - How trust makes hard conversations easier * 34:02 - The conversation leaders avoid until it costs them * 38:38 - The price of being someone people look up to * 40:50 - The seven-month reflection that changed his next chapter * 44:38 - Why belief has to come before confidence * 46:13 - The coach’s real job isn’t technical * 47:12 - Inside Kieran’s Human Endeavour leadership program * 49:59 - Why leadership is learned, not born * 51:26 - The snowball effect of better leaders * 52:07 - The legacy that matters more than winning About Kieran Read Kieran Read is a legendary figure in international sports, having captained the New Zealand All Blacks 52 times during a career that included two World Cup championships. Rising from a self-described "shy kid" to a global leader, Kieran transitioned into professional leadership coaching after a period of intense self-reflection and academic study of applied management. Today, he is a keynote speaker and the creator of The Human Endeavour, a program dedicated to distilling his years of high-performance experience into actionable leadership pillars for the corporate and sporting worlds. Resources and Mentions Kieran Read’s LinkedIn: https://www.linkedin.com/in/kieran-read-00821384/ [https://www.linkedin.com/in/kieran-read-00821384/] Kieran Read’s Instagram: https://www.instagram.com/kieranread08/ [https://www.instagram.com/kieranread08/] The Human Endeavour Program: https://www.redseed.com/kieranread-leadership [https://www.redseed.com/kieranread-leadership] Kieran Read’s website: https://www.kieranread.co.nz/ [https://www.kieranread.co.nz/] Podcast Contact Information: Website: www.learnit.com [http://www.learnit.com] Email: podcast@learnit.com [podcast@learnit.com] Subscribe to the Learn-It-All Podcast: Youtube [https://www.youtube.com/@TheLearnItAllPodcast] I Apple [https://podcasts.apple.com/us/podcast/the-learn-it-all-podcast/id1714645917] I Spotify [https://open.spotify.com/show/1nEHAEkgsTdZvNOTzRk7hZ] Follow Damon Lembi: Linkedin [https://www.linkedin.com/in/damonlembi/] I Instagram [https://www.instagram.com/damonlembi/] I Facebook [https://www.facebook.com/damon.lembi] I X [https://x.com/damonlembi]

304. Why Your Skills Aren't Enough to Get What You Want | Quinn Harwood

Are you settling for stagnant performance because you're wrestling with a deep-seated lack of confidence or the "imposter syndrome" mask? In this episode of The Learn-It-All™ Podcast, Damon sits down with executive coach and author Quinn Harwood to dismantle the barriers that keep high-performing emerging leaders from reaching their next level. Quinn shares his journey from professional basketball with the Los Angeles Lakers and Los Angeles Clippers, where a teenage Kobe Bryant showed him the true meaning of "next level" confidence, to coaching thousands on how to bridge the gap between performance and results. They dive into the psychology of the "hypocrite monster," the critical pivot from a victim mentality to radical ownership, and why a "gateway habit" at the end of your day is more impactful than your morning routine. If you are a millennial or Gen Z leader feeling stuck in your career growth, this conversation provides a clear roadmap to align your mission with your money and build unshakeable resilience. 📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5 [https://dl.bookfunnel.com/3ingcx2pp5] In this episode, you’ll learn... 1. How to defeat the "hypocrite monster" 2. Why moving from "the blame game" to a solutions-based mindset is the ultimate game-changer for reducing stress and achieving consistent results. 3. The "Kobe Level" of confidence: How to move past an intrinsic lack of confidence by attacking your growth gaps with a "Mamba Mentality." 4. Why developing social skills and the ability to influence emotions is the only way to bridge the connection void created by remote work and technology. 5. Why closing out your day with a "midnight mirror" reflection is more critical for your vitality than focusing solely on morning habits. Timestamps * [00:00] Introduction * [01:01] The hidden reason high performers stay stuck * [01:51] What Kobe Bryant revealed before the NBA * [03:35] Where real confidence actually comes from * [08:26] How leaders build belief without lowering standards * [10:31] The three zones of becoming strong in life * [12:11] What three injuries taught him about belief * [14:13] The hypocrite monster every leader has to face * [15:29] Why GrowthTime! had to become a fable * [18:33] The ownership lesson most young leaders miss * [21:37] When ownership gets replaced by victimhood * [24:21] The coaching question that exposed the real problem * [26:44] The village called Youville * [29:19] Why ego quietly keeps leaders stuck * [31:46] How to find purpose when everything feels fuzzy * [33:35] Why AI cannot replace emotional intelligence * [36:15] The remote work trap future leaders need to understand * [39:41] Why learning without action changes nothing * [42:26] What empowered confidence really feels like * [43:51] The adulting gift every graduate needs * [45:03] Why people hire Coach Q when they feel stuck * [48:24] The gateway habit that changes everything * [51:06] Where to connect with Coach Q * [51:53] Damon’s challenge: ownership, growth, and getting unstuck * [52:39] Damon and Madison unpack the Coach Q conversation * [53:28] Is Learnit really a confidence intervention? * [55:44] How to act before anxiety takes over * [59:25] The uncomfortable truth about psychological safety * [01:00:16] Why leaders should celebrate failure first * [01:03:00] The lesson Damon learned from his daughter’s bike race About Quinn Harwood Quinn Harwood is an executive coach, author, and former professional basketball player. After a career that included stints with the Los Angeles Lakers' summer league and the Los Angeles Clippers, Quinn transitioned into leadership, serving as a general manager for high-performance organizations before moving into full-time coaching. He is the author of GrowthTime!: The Clear Path to Unlock Your Best Life and Leadership, a coaching fable designed to help emerging leaders navigate their personal and professional growth journeys. Quinn is dedicated to helping "mission movers" align their values with their careers through his coaching and his "Monday Movers Mindset" newsletter. Resources and Mentions GrowthTime!: The Clear Path to Unlock Your Best Life and Leadership book: https://www.amazon.com/GrowthTime-Coaching-Fable-Unlock-Leadership/dp/B0F1G847H4 [https://www.amazon.com/GrowthTime-Coaching-Fable-Unlock-Leadership/dp/B0F1G847H4] Quinn Harwood’s LinkedIn: https://www.linkedin.com/in/quinn-harwood-455517108/ [https://www.linkedin.com/in/quinn-harwood-455517108/] Quinn Harwood’s website: https://coachqharwood.com/ [https://coachqharwood.com/] Podcast Contact Information: Website: www.learnit.com [http://www.learnit.com] Email: podcast@learnit.com [podcast@learnit.com] Subscribe to the Learn-It-All Podcast: Youtube [https://www.youtube.com/@TheLearnItAllPodcast] I Apple [https://podcasts.apple.com/us/podcast/the-learn-it-all-podcast/id1714645917] I Spotify [https://open.spotify.com/show/1nEHAEkgsTdZvNOTzRk7hZ] Follow Damon Lembi: Linkedin [https://www.linkedin.com/in/damonlembi/] I Instagram [https://www.instagram.com/damonlembi/] I Facebook [https://www.facebook.com/damon.lembi] I X [https://x.com/damonlembi]

303. The #1 Reason Companies Fail (& How To Fix It) | Jamie Shaver

Are you launching great ideas only to watch them fall apart at the finish line? Many organizations struggle with execution because they start with a creative idea rather than a foundational strategy. In this episode of The Learn-It-All™ Podcast, Damon sits down with Jamie Shaver, a strategic marketing leader who specializes in helping companies "get amped" and win. Jamie reveals why a "confused mind says no", whether it's a prospect on your website or an employee tasked with a new initiative. They discuss the critical internal-external alignment needed for success, why 95% of AI projects fail to get past the pilot phase, and how to stop "lollygagging" by implementing core values that actually drive accountability. If you’re tired of mediocre marketing and inconsistent leadership messaging, Jamie shares her blueprint for flipping the script: starting with strategy to give birth to messaging that sticks. 📘 Get a FREE copy of The Learn-It-All Leader Book: https://dl.bookfunnel.com/3ingcx2pp5 [https://dl.bookfunnel.com/3ingcx2pp5] In this episode, you’ll learn... 1. Why jumping straight to creative output creates execution gaps 2. How to use the same principles you use to win external clients, like identifying pain points and ideal profiles to gain internal buy-in for new initiatives. 3. How a lack of workflow integration and unaddressed employee fears about job security keep 95% of AI projects in "pilot purgatory." 4. How to move beyond generic values like "integrity" to descriptive behaviors that empower teams to tackle antiquated platforms and changing interfaces. 5. Jamie’s exact method for sussing out a victim mentality by asking candidates to finish the sentence: "I would be a better leader if..." 6. Why the best leaders learn to let the silence sit during an interview to truly understand a candidate's emotional maturity and intuition. 7. How to protect your team’s culture by exercising your option to give notice to clients who don't align with your core values. Timestamps * 00:00 — Introduction * 01:13 — Why great ideas still fall apart * 02:37 — The Slack message that creates chaos * 04:21 — Why 95% of AI projects stall * 07:24 — The questions leaders skip before launching AI * 08:46 — Why slowing down makes teams faster * 12:51 — The small things that build real trust * 15:23 — The sentence every team needs to hear * 18:22 — When flexibility starts creating confusion * 19:37 — What to do when someone “crushes it” in less time * 20:58 — The second question that reveals motivation * 22:29 — Why canceling one-on-ones sends the wrong message * 23:36 — Core values you can actually fire by * 24:28 — Why “figure it out” became a core value * 26:42 — The interview question that exposes ownership * 28:21 — How to spot a victim mindset before hiring * 29:38 — Why silence might be your best interview tool * 31:19 — The belief Jamie has about every leader * 34:44 — How AMPED keeps values off the wall * 36:18 — The rebel value every company needs * 39:16 — How leaders create safety for hard feedback * 42:11 — The scoreboard that scares the wrong people * 43:32 — When a client deserves to be cut * 45:09 — Why mediocre marketing is everywhere * 46:51 — The bicycle wheel lesson for better strategy * 53:04 — Damon’s challenge for leaders and teams About Jamie Shaver Jamie Shaver is a strategic leader at AMPED, a full-service strategic marketing agency dedicated to eradicating marketing mediocrity. She works with mid-size B2B businesses, manufacturing companies, and global brands to build comprehensive strategies that drive measurable wins. Jamie is a proponent of "truth in love" leadership and believes that small things done consistently are what build lasting trust in any organization. Resources and Mentions Jamie Shaver’s LinkedIn: https://www.linkedin.com/in/jamie-shaver-amped [https://www.linkedin.com/in/jamie-shaver-amped] AMPED’s website: https://ampedstrategy.com/ [https://ampedstrategy.com/] Podcast Contact Information: Website: www.learnit.com [http://www.learnit.com] Email: podcast@learnit.com [podcast@learnit.com] Subscribe to the Learn-It-All Podcast: Youtube [https://www.youtube.com/@TheLearnItAllPodcast] I Apple [https://podcasts.apple.com/us/podcast/the-learn-it-all-podcast/id1714645917] I Spotify [https://open.spotify.com/show/1nEHAEkgsTdZvNOTzRk7hZ] Follow Damon Lembi: Linkedin [https://www.linkedin.com/in/damonlembi/] I Instagram [https://www.instagram.com/damonlembi/] I Facebook [https://www.facebook.com/damon.lembi] I X [https://x.com/damonlembi]