Doug Fleener

Doug Fleener is the creator of The What If Rule™ and author of Start With What If: Weekly Questions to Spark Immediate Change and Growth and The Day Makes the Year (Makes a Life).

His work centers on a simple, powerful idea: you can always create better perspectives and options—starting today.

A former executive and speaker, Doug’s real story isn’t about titles—it’s about transformation. Once a drug addict who was broke and out of work, he rebuilt his life through small, intentional actions that reshaped how he thought, worked, and lived.

That journey began deep in addiction and failure, evolved into executive leadership, including a senior role at the Bose Corporation, and ultimately led to a deeply fulfilling life that now anchors everything he teaches.

Doug helps people see differently, act intentionally, and create meaningful change in real time—at work, at home, and within themselves.

His insights have been featured in The Wall Street Journal, The New York Times, Fast Company, and Inc., but what drives him most is seeing people change their days, one What If question at a time.

He lives outside Boston with his wife, Joanna, and proudly holds the title of “Greatest Dad” (three-time winner).