Learning the Hard Way the Easy Way

Alex Culley
  • 5.0 (6)
  • SELF-IMPROVEMENT
  • UPDATED BIWEEKLY

From subtle misfires to colossal screw-ups, guests recount major mistakes and share something they “learned the hard way”. Hear from successful leaders, experienced executives, entrepreneurs, and other interesting figures as they share their mistakes and what you can learn from them.

  1. OCT 7

    27. Chuck Johnson on Confronting Your Limitations

    When was the last time you confronted what you don’t know? For Chuck Johnson, serial entrepreneur, technologist, and leadership coach, this question has shaped his journey through multiple successful startups. From software engineer to founder, Chuck learned that understanding your limitations is just as important as knowing your strengths. "I needed to learn what other skills are crucial for a successful software company; vision, connections, and sales," he shares. This self-awareness became his superpower, helping him build complementary partnerships. Chuck’s leadership is grounded in empathy, a value learned from his father, who ran a hospital. "My dad always made sure his office was the last to get the window unit," Chuck recalls, showing how actions speak louder than words. He applies this philosophy to his teams, emphasizing a balance between friendship and professionalism. At LifeCloud, Chuck expanded his role into sales, demonstrating the value of stepping outside your comfort zone. "Expanding is uncomfortable but rewarding," he says, modeling a growth mindset. As AI changes the tech landscape, Chuck embraces the same approach: "Don’t fear what’s smarter than you." Success, he believes, comes from building relationships with people, and now, technologies, that complement your abilities. Want to learn how self-awareness and collaboration drive success? Listen now to hear more from leaders redefining the future.

    56 min

  2. SEP 23

    26. Caitlin Shea on the Gift of Getting Fired

    What happens when your career trajectory gets derailed by an unexpected firing? For Caitlin Shea, Vice President of Development for Discovery Children's Museum, that moment of professional crisis became the foundation for authentic leadership and personal transformation.   This candid conversation goes beyond typical career advice to explore the rarely discussed aftermath of professional failure. Caitlyn reveals how being fired forced her to recognize that she was "so much more than her job" and ultimately shaped her into a more authentic and compassionate leader. The discussion takes a powerful turn as Caitlyn draws parallels between professional loss and personal grief, sharing how losing her mother during the pandemic further transformed her approach to authenticity in the workplace.     For listeners grappling with setbacks or questioning their professional identity, this episode offers a refreshing perspective: failure isn't the end but often the beginning of something transformative. As Caitlyn eloquently puts it, "When we invite others into these darkest moments, those moments that feel like they're never going to go away, what happens is the brightest, most vibrant light shines through."   Ready to transform how you view professional setbacks? Listen now to discover why sometimes the hardest lessons become our greatest gifts. Caitlin Shea LinkedIn DISCOVERY LINKEDIN

    1h 1m

  3. 09/30/2024

    25. Carlos Marin on Turning Setbacks into Stepping Stones for Success

    What if every failure you encountered was actually a stepping stone towards success? In this episode of "Learning the Hard Way, the Easy Way," Carlos Marin, international leadership consultant and executive coach, joins Alex to share his philosophy on the relationship between failure and success. Carlos talks about learning from his own failures and how he translates them to his work mentoring executives worldwide. Carlos and Alex unpack how resilience and the ability to manage fears can redefine your self-perception and catalyze personal growth. Discover the fine line between learning from your mistakes and being overly critical of them. Carlos and Alex explore the intricate balance of thoughts, feelings, and behaviors, and how cultural nuances play a role in handling failure and willingness to ask for help. They dive into the common fears executives face and how these anxieties can stifle personal growth. Through relatable anecdotes and practical advice, Carlos and Alex also consider the profound impact of these lessons on parenting, particularly in fostering resilience and a growth mindset in children. Throughout the conversation, Carlos and Alex underscore the importance of mentorship and self-reflection in achieving tangible results. Carlos shares how reframing your perspective can influence your actions and feelings, leading to more positive outcomes. They discuss the necessity of clear objectives and feedback loops in effective mentorship and coaching. By the end of this enriching conversation, you'll have a toolkit of strategies to embrace failure as an opportunity for growth, both in your professional and personal life. Don't miss this chance to learn how failure and success harmoniously contribute to a fulfilling journey. Carlos on LinkedIn

    52 min

  4. 09/11/2024

    24. CB Bowman-Ottomanelli on Confronting Corporate Racism with Courage

    Ever encountered a situation where you felt out of place because of systemic biases? Join Alex for a profound conversation with CB Bowman-Ottomanelli, a master executive coach, who shares her eye-opening experiences with corporate racism. Raised in a diverse and inclusive environment, CB was blindsided by the harsh reality of racial discrimination when she stepped into the corporate world. Through powerful narratives and personal stories, she shares how she navigated these challenges with courage, resilience, and grace. Discover how effective communication and the wisdom to choose battles can transform experiences of confrontation into opportunities for growth. By reflecting on her journey of opening a company and seeking advice from trusted voices, CB illustrates the importance of empathy in addressing discrimination. CB and Alex unravel the complexities of corporate diversity, examining real-world examples like the varied reactions to George Floyd's death and the significance of racially charged symbols. These stories reveal the courage required for constructive conversations about race and inclusion. As the duo explores the nuanced evolution of corporate racism, CB's insights highlight the critical difference between genuine courage and performative diversity efforts. From navigating workplace promotions to fostering true allyship, CB and Alex emphasize the need for continuous learning and empathy. Dive into the intricacies of systemic biases, the manipulation of numbers, and the importance of having a diverse personal board of directors. Gain actionable strategies from CB's experiences and her book, "Courage to Leap and Lead," to build a more inclusive and understanding workplace environment. CB on LinkedIn Courage Consulting Courage to Leap and Lead Podcast Courage to Leap and Lead on Amazon

    1h 4m

  5. 08/12/2024

    23. Ernesto Mandowsky on Finding your Passion

    Is there a secret to discovering our passion? Listen to Alex's conversation with Ernesto Mandowsky, the brain behind the Million Dollar Machine, who shares his incredible journey from the world of hospitality technology to entrepreneurship. Discover how Ernesto’s book, “NewBee,” helped him discover his true passion and better appreciate the experiences along the way. His unique perspective focusing on genuine aspirations over job titles is a must-hear for anyone seeking clarity in their professional life. Ernesto opens up about the significant role of mentorship and reflection in achieving success. Through a heartfelt story about a mentor he met in college, Ernesto explains how dedication and commitment can attract the right kind of support. During the conversation, Ernesto and Alex discuss the importance of having a clear vision for your life and how to balance leadership with being a supportive team player. Ernesto offers advice on balancing work and personal fulfillment with practical, actionable steps for anyone feeling overwhelmed by life’s challenges. Learn from Ernesto’s experiences writing a book and the pivotal moment when he chose between a stable career and an entrepreneurial path. His insights on financial discipline, goal-setting, and an enterprising mindset provide invaluable tips for both aspiring entrepreneurs and seasoned business owners. Ernesto on LinkedIn Million Dollar Machine NewBee on Amazon

    1 hr

  6. 06/09/2024

    22. Rick Torrison on Overcoming Limiting Beliefs

    Join us on this episode of Learning the Hard Way the Easy Way, for a conversation with leadership coach and best-selling author, Rick Torrison. Rick's journey to break free from his limiting beliefs and embrace his authentic self will inspire you to question the "normal" in your own life. Rick and Alex dig into the cultural and generational influences that shape mental health and perceptions of our own behaviors. From the "stiff upper lip" mentality to the more open conversations sparked by the pandemic, they discuss how these factors can create workplace conflict and hinder personal growth. This episode encourages you to reflect on whether the norms in your life truly benefit you, or if you're accepting beliefs about yourself that actually hold you back. Is it easier to act yourself into a new way of thinking? Or think yourself into a new way of acting? During the conversation, Rick and Alex explore the relationship between belief structures and behavior change. They discuss the importance of aligning beliefs with actions while sharing practical insights and anecdotes to recognize self-destructive patterns and achieving lasting change. Rick reinforces the importance of redefining past experiences and having a clear vision to bridge the gap between your current reality and your desired destination. This episode is packed with actionable tips for overcoming limiting beliefs, fostering a culture of authenticity, and achieving both personal and organizational growth. Don't miss this impactful discussion on ways to reshape your views of yourself and the world around you. Rick on LinkedIn Rick on Instagram Buy Rick's Book: Born Limitless

    1h 10m

  7. 05/20/2024

    21. Markus Kaulius on the Myth of Solo Success

    Do you ever feel like you have to do it all on your own? Entrepreneur, author, and philanthropist Markus Kaulius joins Alex in an inspiring discussion to shatter the myth of solo success and share how he learned to lean on others in this episode of Learning the Hard Way the Easy Way. Even if we know the 'lone wolf' mentality doesn't work, we don't always know where to turn to for guidance. Markus and Alex explore the cultural, generational, and personal influences that shape the relationship between confidence, ego, and willingness to ask for help. Markus recounts his own struggles early in life trying to find the voices that spoke to him. Do mentors have to be in your field or industry? Can you only learn from those who are less successful than you? Do you even have to know someone to consider them a mentor? Markus answers a resounding no to all of the above. He and Alex talk about the importance of staying teachable and being open to new insights while also having the strength to tune out a message, or a messenger, that isn't right for you. But listening and learning isn't enough. Success comes from taking action. Markus and Alex discuss strategies to build sustainable habits, focusing on the importance of starting small — with our health, career, or personal relationships. Tune in to hear a thoughtful examination of the habits that shape our lives, and how nourishing your curiosity can make all the difference on the path to success. Markus on LinkedIn Markus on Instagram Playabiggergame.com Pre-order Play a Bigger Game: Seven Universal Principles to Experience True Fulfillment and Win at Life

    1h 1m

  8. 05/05/2024

    20. James Kaikis on Letting Go of Control

    When the reins of control slip from our grasp, it's a startling revelation that can make or break a leader. James Kaikis, a tech entrepreneur, founder, and Chief Solutions Officer sits down with Alex to share his personal evolution from a micromanager to an empowering leader in the latest episode of Learning the Hard Way the Easy Way. James opens up about critical moments that reshaped his management philosophy, like a frank critique from a company executive and a family vacation that turned into a lesson on trust.  Throughout their conversation, James and Alex shed light on the art of hiring capable individuals and the benefits of leaders stepping back to let their teams shine. Ever found yourself wondering how to elevate a struggling team member without micromanaging? James and Alex's back and forth reveal an approach that favors empathy and structured support over "old school" supervision. James's experiences are a playbook for those dealing with underperformers as he offers his tried-and-true strategies to transform potential into excellence. His perspective is a testament to the power of a transparent, supportive workplace where every individual feels valued and driven to succeed. Tune in for a conversation that balances the emotional weight of leadership with the tactical finesse of managing a team. From the nuances of feedback culture to the parallels between business and sports, James's insights span the full spectrum of guidance and mentorship in a fast-paced professional environment. His reflections on entrepreneurship, risk-taking, and the trials of forging one's path are filled with wisdom and heart. It's a conversation that will inspire you to embrace your vulnerabilities as strengths and lead with purpose. Join Alex for an honest exploration into the transformative power of letting go. James on LinkedIn GTMshift Website TestBox Website

    58 min
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Ratings & Reviews

5
out of 5
6 Ratings

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From subtle misfires to colossal screw-ups, guests recount major mistakes and share something they “learned the hard way”. Hear from successful leaders, experienced executives, entrepreneurs, and other interesting figures as they share their mistakes and what you can learn from them.

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