Episode #96: Michael Youngblood on the Value of Beautiful Questions

The Discomfort Practice

In this episode of the Discomfort Practice, I talk with Michael Youngblood, co-founder and CEO of Unsettled, an award-winning travel community for those who embrace the unknown and value meaningful human connection. He has worked in more than 60 countries, collaborated with the White House on entrepreneurship and global development, advised Fortune 100 companies on remote work, and has taught courses on entrepreneurship and globalisation on behalf of the U.S. State Department. Previously, he was the Managing Editor of Innovations journal, a publication about entrepreneurial solutions to global challenges that is jointly hosted by MIT, Harvard, and George Mason University. Michael is a member of the inaugural TED Residency, a member of Sandbox, and an avid sailor, mountain biker, and global explorer.

Michael and I discuss Unsettled’s manifesto as a process and a guiding philosophy for how to live, through embracing the uncomfortable and the unknown. MIchael shares his own thoughts on navigating anxiety and depression in work and life, and the importance of taking time for self-reflection. We explore some ‘beautiful questions,’ and hopefully help those listening to discover something themselves with those questions (or discover their own questions to help them explore and find their way of being, living and doing in this rapidly changing world). Many of us know that we can’t do things the way they’ve always been done, so this is a timely conversation. Just know that you’re not alone. Enjoy!

Key Points Discussed:

• The uncomfortable childhood experience of holding hands with his adoptive black sister and being the target of hate speech, showed Michael early on the levels of prejudice and inequalities existing in the world. And how that led to him studying social sciences, as the pathway he saw to change social structures. (5:40)

• Michael views all questions as beautiful, as they open you up to possibilities, whilst seeking new answers. (13:00)

• What is your dream underachiever job? (17:20)

• Getting clear on what is important to Michael, with time and space for self-reflection. Opening yourself up to new opportunities, that reflect your desired lifestyle and pace of work/life balance. (27:20)

• Unsettled manifesto: being more than a travel company. It’s a process and philosophy for living: embracing the unknown and the uncomfortable. (32:30)

• How Michael has dealt with and found tools to overcome anxiety. (42:40)

• 70% of people quit a job within 18 months of an Unsettled travel experience. (47:40)

• How to create your own reality. (57:30)

• Michael’s affirmation that he comes back to at the end of every day: “Despite everything, today was a great day.” He has choice and agency to see today as a great day, despite what might have happened in it. (1:00:00)

Connect with Michael:

• Unsettled Manifesto

• Michael’s TED Talk “Discovering Your True North”

• Michael’s Blog on “Becoming CEO Of Unsettled”

• Michael on Linkedin

Connect with Betsy:

• Betsy on Instagram

• Betsy on Twitter

• Betsy on Linkedin

• What is a Beautiful Question?

Rate, Review, Learn and Share

Thanks for tuning into The Discomfort Practice. If you enjoyed this episode, please subscribe, follow, like, and/or drop us a five star and written review. Share this episode with others and help spread the word and grow our audience. Don’t forget to tune into our other episodes and share your favourite ones on social media!