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Learning the Hard Way the Easy Way

Learning the Hard Way the Easy Way

Written by: Alex Culley
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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.© 2026 Learning the Hard Way the Easy Way Careers Economics Management Management & Leadership Personal Success Self-Help Success
Episodes
  • 32. Alex Seiler on Chasing the Right Career for the Wrong Version of Yourself
    Jan 12 2026

    This episode explores how life-altering moments can fundamentally reshape our definition of success, work, and legacy. After losing his mother, globally recognized people leader Alex Seiler confronted the illusion of unlimited time and re-evaluated goals that no longer fit who he had become. Grief became a clarifying force, prompting deeper questions about identity, purpose, and what it truly means to live, and be known for, a meaningful life, rather than chasing success for an outdated version of oneself.

    From that clarity emerged a reimagined approach to career and leadership. Alex shares why he stepped away from traditional career ladders to design a portfolio career blending executive leadership, advising, writing, speaking, and partnerships, each chosen for income, impact, learning, or legacy. The conversation challenges narrow definitions of loyalty, titles, and progression, arguing instead for values alignment, optionality, and being “brilliant at the basics.” Practical insights span early-career guidance (building transferable skills, saving for choice, finding community beyond one employer) to senior leadership lessons on pacing change, meeting organizations where they are, and leading without judgment.

    At its core, the episode is about relationships, reflection, and intentional change. Alex discusses building a personal board of advisors, creating trust through accountability, and making reflection a daily practice rather than a crisis response. The conversation ultimately returns to legacy: not “Have I been successful?” but “What do I want to be known for next?” For anyone questioning whether their career still fits the life they want, this episode offers a thoughtful, humane blueprint for choosing work that evolves with who you are becoming.

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    1 hr
  • 31. Srikar Bhagavatula on the Burden of Should
    Dec 17 2025

    Success rarely follows a straight line, and this episode leans into that truth. Srikar Bhagavatula shares how lofty goals, self-doubt, and the pressure of "should" can quietly paralyze us, especially when we compare our messy, nonlinear paths to the curated success stories of our peers. From research that refuses to give clear answers to careers that detour far from the original plan, Srikar reframes uncertainty as part of the work. The real challenge isn’t getting everything right, but staying honest to the process and resisting the false narrative that everyone else is ahead.

    At the heart of the conversation is the distinction between "good shoulds" and "bad shoulds". "Bad shoulds" are driven by external expectations, outcomes, and fear of failure; "good shoulds" are grounded in values like curiosity, integrity, and effort. Srikar reflects on how early role models, teachers who celebrated being proven wrong and parents who modeled quiet honesty, shaped his compass, while acknowledging that many people must later rewire their values through experience, therapy, and reflection. Growth, like values, is nonlinear, and learning to ask better questions often matters more than finding immediate answers.

    Unexpectedly, the dance floor becomes a metaphor for leadership and life. Through West Coast Swing, Srikar learned the value of listening, adaptability, and frequent, low-stakes failure, putting himself in situations where being uncomfortable was unavoidable. Whether in research, careers, or relationships, progress comes from choosing challenges that stretch you without breaking you. This episode is a reminder that failure is part of the path and that when you define your why clearly, timing and outcomes have a way of catching up.

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    1 hr
  • 30. The Mackins on Parenting Myths, Mistakes, and Memories
    Nov 26 2025

    Have you ever realized that parenting is the ultimate leadership training ground? In this deeply honest episode, Jon and Danielle Mackin invite listeners into a raw conversation about family, faith, and the lessons they keep learning.

    They admit that nothing exposes your blind spots faster than raising kids. As Danielle jokes, “I was the best parent until I became a parent.” The two reflect on how the journey of nurturing children has required them to reparent themselves, all while learning grace, patience, and how to surrender control in a world that constantly tests them.

    The Mackins open up about the early years, the evolution of their relationship with control, and the art of loving each child uniquely. They share how faith has become the solid rock beneath their family, and how leadership at home often mirrors leadership in life: you can’t protect those you love from every hard thing, but you can walk beside them as they learn. With vulnerability and warmth, they explore how moms and dads often see parenting differently, and how those contrasts can strengthen rather than divide.

    The episode also explores modern realities such as raising kids on “their parents’ social media” and capturing family life in real time. Jon and Danielle reflect on the lasting gift of transparency: giving their children the ability to “know them later” through stories, recordings, and the honest encyclopedia of what it took to raise them. Whether you’re a parent, leader, or both, this conversation is a reminder that leadership begins in the home, that faith steadies the chaos, and that sometimes the most profound lessons are the ones we have to learn the hard way.

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    1 hr and 1 min
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