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999: The Most Underrated Leadership Skill: Why Having FUN Drives Results | Leadership Strategies episode artwork

EPISODE · Jul 7, 2026 · 30 MIN

999: The Most Underrated Leadership Skill: Why Having FUN Drives Results | Leadership Strategies

from Shameless Leadership · host Sara Dean

I’ve worked with high-achieving women for over two decades. I think I attract high-achieving women because this is an attribute I deeply relate to - sometimes to my own detriment. One of the things I’ve noticed my clients and I can struggle with is FUN. High achievers tend to take things seriously. Like, very seriously. We are intense and motivated to make everything great, if not perfect. This drive can suck the life right out of what otherwise might have been a footloose and fancy-free experience. Rather than embracing fun as a birthright, high-achieving women in leadership have a tendency to treat fun only as a reward - which must be earned after a remarkable and noteworthy win. It’s as if somewhere along the way, we convinced ourselves that fun belongs to others but not to us. But here's what I've learned: when you connect fun only to rewards and achievement, you aren't just flirting with leadership burnout; you're leaving one of the most underrated leadership skills on the table. Fun isn't a reward or a distraction from the work of female leadership — it's an essential emotional intelligence practice that sharpens decision-making, deepens connection, and builds sustainable leadership. In this episode, I break down the essential elements that make something truly fun (hint: it's not just scheduling a happy hour), why high-achieving women are particularly prone to forgetting how to access it, and why reframing fun as a leadership strategy — not self-care, not a luxury, not an afterthought — changes everything. We will also walk through a simple 5-step process for reconnecting to your version of fun — not the Instagram version, not what your team thinks sounds good, but the kind of fun and joy that actually replenishes you. Because the most powerful leadership development tool often isn't another productivity system or another personal development book - it's remembering how to be fully alive and in your joy while you lead. Links Mentioned: Early Bird Enrollment is open for my Aligned Leadership Incubator! Save $500 if you apply by June 30th: saradean.com/aligned Hire Sara to speak: saradean.com/speaking Coach with Sara: https://saradean.com/executive-coaching-services Connect with Sara on LinkedIn: https://www.linkedin.com/in/saradeanspeaks Watch Shameless Leadership episodes on YouTube: https://www.youtube.com/@saradeanspeaks Learn more about your ad choices. Visit podcastchoices.com/adchoices

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999: The Most Underrated Leadership Skill: Why Having FUN Drives Results | Leadership Strategies

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