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Unhustle Podcast

Values Based Leadership with Chip Conley on the Unhustle Podcast

Milena Regos

In a world obsessed with busyness and chasing success at all costs, we end up burnt out, stressed out, and lonely. At Unhustle, my vision is to shift this paradigm. It’s about finding the sweet spot between doing and real living, embracing a lifestyle that balances life enjoyment with purposeful achievement. This is the future I’m creating with Unhustle—a sustainable, prosperous future for ourselves, our families, communities, teams, companies, and the planet.

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Hi! I'm Milena Regos, the Human behind Unhustle®.



Reading Time: 2 minutes

How one man realized he had lost his life values to the hustle

Chip Conley is known as being a rebel entrepreneur. I also consider him as one of the few living a values based life. As the founder of Joie de Vivre, Chip built the second largest boutique hotel brand in America. Chip is what everyone will consider a successful entrepreneur.

As a young man, Chip started his business grounded in his life values for freedom and creativity. Twenty-four years later, following an infection in his body, Chip flatlined. This near-death experience led him to rethink his life. While running his business and managing 3,500 employees, he had lost his values for freedom and creativity. He had lost his WHY for starting the company in the first place. Sound familiar?

Chip decided to make a change. Change is not easy. Change takes courage. But being grounded in his values helped Chip along the way.  In Chip’s case, as in our case, with change comes a financial challenge. But Chip was committed.

He sold the business and took the time to reconsider his life and regain his freedom and creativity. During this time he wrote his latest book Wisdom@Work: The Making of a Modern Elder. Then, one day Airbnb reached out to him to help them transform their promising start-up into the world’s leading hospitality brand. Chip was back in the corporate world. Instead of working 15 hours/week as he thought at the beginning, he went back to working 15 hours/day.

Walking away from money to do purposeful work is a theme in Chip’s life. Chip regained his freedom and creativity yet again, this time, 4 years later. Although he’s still advising AirBnB, he found balance in his life by moving to Baja California Sur. He founded the Modern Elder Academy in Mexico, and as he says in the podcast: “He Serves and He Surfs”!

Chip Conley inspires and leads people who need to hit the reset button, evaluate their midlife situation, get grounded in their life values, and welcome change.

Listen to the podcast or watch the video with Chip Conley. Sign up for the Unhustle newsletter to get more tips to live a life grounded in values, wellbeing, simplicity, joy and courage.


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