S1E6 | Create Life-Changing Possibilities Without Piling On Debt, Even If Exploration Feels Daunting

From his start as a newspaper artist to founding XPLANE, a company that collaborated with 40% of the Fortune 500,

Dave Gray

’s journey is proof that you don’t need massive leaps to create a life of freedom — just intentional steps powered by curiosity and courage.

Here’s what you’ll learn in this inspiring interview:

• Embrace Uncertainty: See how Dave turned questions like “What if?” into actionable experiments, reframing risk as opportunity.

• Balance Creativity and Stability: Discover how he created financial cushions and prioritized his passions while transitioning into self-employment.

• Live a Life of Possibilities: Learn how Dave cultivated a mindset of experimentation that led to a fulfilling and values-driven career.

Today, as the founder of The School of the Possible, Dave inspires countless others to adopt a Possibilitarian mindset—one rooted in curiosity, courage, and conviction.

Ready to Explore Your Own Possibilities?
Listen now to uncover how to:

• Reframe risk and find freedom beyond the corporate grind.

• Build stability while pursuing your passions.

• Ask the life-changing “What if?” questions that open new doors.

Then, join your fellow Corporate-Dropouts LIVE every Wednesday at 11am ET | 4pm GMT to get support for your next steps.

Find Support at the WaterCoolerCall

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Be sure to reach out to Dave

Visit his website, SchoolOfThePossible.com, to

• Subscribe to his newsletter on community experimental learning.

• Attend free weekly 90-minute experimental learning sessions.

• Learn how Dave acts as a “Johnny Appleseed” dropping seeds of possibility everywhere he goes to develop a discovery mindset in others.

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Corporate Dropouts, Start Here!

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Timestamps

00:00 Introduction to the Corporate-Dropouts Stories Podcast

02:11 Dave Gray's Early Career and Inspirations

05:55 Transition from Corporate to Academic Life

10:18 Starting a Business and Taking Risks

16:22 The Importance of 'What If' Thinking

21:43 Managing Risk and Financial Independence

26:34 The Power of 'What If' Thinking

27:34 Reversibility of Decisions

28:39 Experimentation and Rejection

30:01 The Corporate World and Fear

32:28 Living a Thrifty and Creative Life

37:31 Finding Stability for Creativity

38:14 Taking Risks and Making Decisions

41:03 Daily Habits and Small Experiments

43:54 The Possibilitarian Philosophy

47:00 Conclusion and Final Thoughts