Why So Many High-Level Leaders Struggle in Midlife (And What to Do About It)
It’s a pattern you’ve likely noticed, maybe even lived.
A high-level CEO, founder, or executive reaches the peak of their professional life… and finds themselves quietly miserable.
From the outside, they’re winning. The business is thriving. The money is flowing. But internally, something’s off. They feel restless, disconnected, even lost.
Why?
Because many leaders hit midlife with success in one hand and emptiness in the other.
Here is something for you to consider: Success Doesn’t Have to Mean Sacrifice!
Here’s why high achievers often struggle in midlife:
- They over-identified with work. Career became identity. The person behind the title got lost.
- They neglected personal growth. Leadership demanded evolution—but only in one narrow direction.
- They avoided vulnerability. In roles that required strength, asking for help or expressing uncertainty felt unsafe.
- They ran out of runway. With goals achieved, they don’t know what’s next. That “what now?” question is louder than ever.
- They ignored deeper values. Wealth and prestige were pursued over meaning and connection. And now the soul is starving.
But it doesn’t have to stay that way.
It’s up to us to design a great life. We can do it together.
Five Ways Leaders Can Design a Better Life (Outside of Money):
- Reconnect with Your Purpose (Beyond the Boardroom) What truly energizes you? Mentoring, art, impact, family, spirituality? Build your life around that, not just spreadsheets and strategies.
- Invest in Identity Work Who are you when you’re not “the boss”? Work with a coach or therapist to explore who you are without the title.
- Design Rhythms, Not Just Routines Instead of rigid schedules, create seasonal rhythms for rest, creation, connection, and learning. Live in cycles, not sprints.
- Cultivate Real Relationships Seek out friendships and communities where you don’t need to perform. Find people who see you, not just your success.
- Create for Joy, Not Just Output Paint. Write. Cook. Travel. Start a podcast no one listens to. Let yourself be bad at something and love it anyway.
Final Thought: Midlife isn’t a crisis. It’s a mirror. And if you’re willing to look closely, it can also be a portal, a doorway to a fuller, freer, more human version of leadership.
Because what you build outside your career may end up being your greatest legacy.
If you’re struggling to find the answers, there are a few ways I can help:
1. Join the Elite Leaders Network (HERE)
2. The Elite Leaders Newsletter with 125,000+ subscribers (HERE)
3. Setup a FREE 20 minute call with me directly to talk about possibilities (HERE)
