Then, I realized throughout my career (and life) that people have said that to me in various ways. They expressed shock when, at 26, I bought a bankrupt, pay-by-the-hour motel in San Francisco’s Tenderloin to turn it into a rock ‘n roll hotel. They told me I was nuts to join the Millennial founders of Airbnb as their in-house mentor and “modern elder” before most people had heard of the home-sharing company. They told me there was no precedent for a “midlife wisdom school” focusing on reframing our relationship with aging when I co-founded MEA. It wasn't unusual for a more traditional observer to doubt my unconventional paths, wondering if perhaps I was off my rocker.

But now that I’m getting to the age in which I have a rocker, I hear a little voice in my head saying, “I’ve been here before.” That’s what wisdom is: the ability to call upon our metabolized experience. Our painful life lessons are the raw material for our future wisdom. I’ve now had forty years of entrepreneurial experience, so I have lots of raw material to work with. When I was 36, I’m not sure I could have said, “I’ve been here before,” but at 63, I trust that my intuition is lubricated with my past lessons. 

Getting into a state of flow requires the melting together of action and consciousness, the state of finding a balance between a skill and the challenge of that task. In order to do this, you have to be open to failing. If the task isn’t challenging, you’ll be bored, and there’ll be no flow. 

The father of flow, Mihaly Csikszentmihalyi, reminds us that wisdom flows from joy (which I particularly like since my boutique hotel company was called Joie de Vivre):

‍“It is essential to remember that the pursuit of wisdom, and its deployment, thrive on joy. The best recipe for the spread of wisdom is the encouragement of curiosity, respect for the best accomplishments of the past, coupled with a burning desire for improving on them; and all of this within a conception of self that extends to other people, the planet and beyond. When these elements are in place, a joyful immersion in the complexity of life is likely to ensue - an openness to experience, a willingness to dive deep into issues of concern to self and others. If such an attitude develops far enough, then understanding life becomes increasingly rewarding in itself. The person will be seen as wise, and his or her actions also will be considered wise.” 

So, rather than take offense to this statement from the luxury hotelier, I take it as a compliment suggesting that my risk-taking is just reacquainting me with my past experiences, which I’m just trying to improve upon. And, in so doing, I’m finding my flow…and my joy.

‍How might you consider the statement, “I’ve been here before,” when you feel a little stymied and trying to summon your wisdom and courage?

If today’s blog post intrigues you, I hope you’ll join me, Steven Kotler (the world’s leading expert on flow), and my cofounder Christine Sperber for “Finding Flow in Midlife and Beyond” June 10-15 at our Santa Fe ranch campus. 

-Chip