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8 Women, 8 Careers - Leadership Lessons for Midlife

Writer: Kay Henderson
Kay Henderson
Sep 29, 2025
1 min read

What decades of experience can teach about leadership, resilience, and unapologetic confidence.


Over the weekend, I reconnected with 7 women I first met in my 20s. Across three decades, we’ve shared marriages, divorces, births, deaths, promotions, and reinventions.


Now in our 50s, the constant is clear: connection, support, and growth.


If we could speak to our younger selves, here’s what we’d say:

✅ Trust your instincts

✅ Boundaries matter

✅ Success is rarely linear

✅ Don’t apologise for taking up space

✅ Relationships are everything


These lessons mirror patterns I see in my coaching clients: leaders navigating change, growth, and new chapters.


Reflection

Which of these lessons resonates most with your current leadership journey, and where could you lean into it this week?



How might applying these insights change the way you lead, connect, or grow in your career today?

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