Harry Hastings didn't just leave a 33-year career in education—he built something entirely new. After decades of leading schools and mentoring educators, Harry made the bold decision to launch The Sherpa, an executive coaching practice dedicated to helping leaders navigate their most challenging transitions with clarity, confidence, and purpose.In this candid conversation, Harry shares the real story behind his first year as an entrepreneur. From landing his first paying client (a former student) to building a practice of 30+ active clients across diverse industries, Harry opens up about what actually works—and what doesn't—when building a coaching business from the ground up.We explore the philosophy behind The Sherpa name and why the metaphor of a mountain guide perfectly captures Harry's coaching approach: support, challenge, and guidance delivered with wisdom earned from decades in the trenches of leadership. Harry shares powerful stories from his work, including how he supports head teachers navigating school closures, helps young professionals discover their values and direction, and coaches executives across venture capital, real estate, and beyond.You'll hear Harry's honest take on the challenges of irregular income, the discipline required to constantly "sow while you harvest," and why LinkedIn became his most valuable client acquisition tool. He breaks down the difference between coaching and mentoring (a distinction many potential clients don't understand), explains his values-driven coaching methodology, and shares the beautiful client testimonial that coaching is like "pumping up your tires"—you can't complete your journey on flat tires.But perhaps most powerfully, Harry offers one word of advice for every coach starting out: enjoy. In a world that glorifies hustle and overwork, Harry reminds us that if you're your own boss, you need to actually be your own boss—which means protecting your well-being, setting boundaries, and remembering that "enough" is a complete sentence.Whether you're launching your coaching practice, scaling to your next level, or simply curious about what it takes to make a major career transition successful, this episode offers both tactical strategies and profound wisdom you won't want to miss.About Harry HastingsHarry Hastings is a Level 7 ILM Executive Coach and founder of The Sherpa, an executive coaching practice specializing in leadership development and transformational change. After 33 years in education—including distinguished Headteacher roles at Ardingly and Brighton College Prep Schools—Harry made the transition into full-time coaching in 2024.Since launching The Sherpa in September 2024, Harry has accumulated over 300 coaching hours and currently works with 30+ active clients spanning multiple sectors, including education, venture capital, executive search, real estate, and luxury travel. He is also pursuing his ACC (Associate Certified Coach) certification through the International Coach Federation (ICF).Harry's coaching philosophy centers on three core pillars: support, challenge, and guide. Drawing from his extensive leadership experience and his Level 7 ILM training (facilitated by Love Your Coaching), Harry helps clients clarify their values, navigate high-stakes transitions, build confidence without arrogance, and create sustainable success in both their professional and personal lives.His client roster includes senior executives, head teachers, emerging leaders, and even former students—now in their 30s and 40s—who return to work with Harry in what he calls "chapter two" of their relationship. Harry is known for his values-driven approach, his emphasis on accountability and action, and his ability to create safe spaces where leaders can be vulnerable, process difficult emotions, and discover their own solutions.When he's not coaching, Harry enjoys walking in the Sussex woods with his dog (where he first conceived The Sherpa name), playing golf (though not as often as he'd like), and continuously learning from his own network of coaches and mentors.Connect with Harry:📧 Email: [email protected] 🌐 Website: www.thesherpa.pro

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