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The Myth of “Having It All Figured Out”


Society often portrays midlife as a time when you finally “have it all figured out.” But just because you may have reached the pinnacle of your profession and achieved a certain level of financial security, that doesn’t mean it’s time to settle into complacency.

I sold my company Joie de Vivre in 2010 after two-dozen years of painstakingly growing it into one of the largest boutique hotel companies in the world. On the outside, it looked like I knew it all. I was writing best selling leadership books, giving speeches on the TED stage, ringing the bell at the New York Stock Exchange, and smiling through it all while my bank account got smaller and smaller in the Great Recession. The success gap between how it looks and how you feel can be the widest gulf in the world, a perilous suspension bridge over a rocky canyon.

Ultimately, I sold the company after not taking a salary my last 3+ years and getting seriously in debt. I looked like I had it all figured out, but my bankers knew better. Upon the sale, at 50, I had the freedom to be curious after years on the treadmill. I spent two years in my “midlife atrium” studying festivals, hot springs, and the nature of emotions and, then, being asked to join a small tech start-up as the “modern elder” of Airbnb, a place where I often felt like the dumbest person in the room given I had no experience in the tech industry. I could have said no to the Airbnb founders, but instead I knew there was something to learn. 

True wisdom comes not from knowing everything, but from recognizing there is always more to discover. In fact, social science proves that continuous learning is one of the critical components to living a long, happy, and fulfilling life.

When you’re in midlife, staying curious matters more than ever. Adopting a beginner’s mindset and embracing constant learning helps improve your cognitive health. Learning new skills, whether professional, creative, or personal, fosters confidence and adaptability.

The world is changing rapidly—staying engaged through learning helps you remain relevant, connected, and inspired. By embracing learning, you set an example for younger generations and peers, showing that growth never stops. Your willingness to evolve and explore new ideas makes you a more effective mentor, leader, and role model.

If you’re looking for an opportunity to learn new ideas and practices that can make your life better, join us online for our Midlife Mastery Summit starting a week from today March 14-16.

You’ll get the chance to hear from Arthur Brooks, author of From Strength to Strength, Martha Beck, author of The Way of Integrity and Beyond Anxiety, Krista Tippett, host of the popular podcast, On Being, award-winning musician Michael Franti, and others who are among the world’s most renowned thinkers (and feelers) in the fields of healthy aging, finding purpose, cultivating resilience, deepening your relationships, and so much more. 

For less than $100, it could change your life. Curious to learn more? You can check out the details here. 

-Chip

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