Cover of the book Start With What If

I'm Doug Fleener—author, speaker, and creator of The What If Rule.

Most change fails in real time—pressure rises, old habits take over. I teach a simpler path.

The What If Rule Pause. Question. Go.

You can always intentionally create better perspectives and options.

Used by individuals and leaders to create clarity, take action, and grow faster—at home, at work, and under pressure.

Get the book or join The What If Weekly to start today.

Get the book now or sign up for weekly What If questions to start putting this to work immediately.

Immediate, practical change and growth for everyday life.

Start With What If

Doug Fleener and his wife Joanna

Hello. I’m Doug Fleener

I didn’t arrive at this work through theory.

My path has included success, failure, rebuilding, and starting over.

In my early years, addiction nearly took everything from me. Recovery reshaped how I think about responsibility, leadership, and relationships. It taught me that real change happens one decision at a time — often in the smallest moments.

Professionally, I went on to lead teams across the country, serving as Director of Retail for Bose Corporation and later running a national company as CEO. I have worked with executives, entrepreneurs, and frontline managers who want leadership that works in the real world — not just on paper.

Real life has been my greatest classroom. The most important lessons rarely come from a boardroom. They come from how you show up at home, at work, and in the moments no one else sees.

Joanna, my wife and partner in this chapter of life, reminds me that growth is not about perfection. It is about awareness, ownership, and doing the next right thing.

Doug’s Insights Have Been Featured In

Logos of The Boston Globe, Business Insider, The New York Times, WSJ, and Fast Company.

And hundreds of newspapers, magazines, and podcasts.

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    WHAT READERS AND AUDIENCES SAY

    What If You Connected with The What If Rule Today?

    SPEAKING

    Turn your event into a catalyst for real growth and transformation. Learn more about booking Doug Fleener.

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    THE DAILY WHAT IF

    The Daily What If is a quick daily prompt that helps you pause, think differently, and move forward with intention.

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    COACHING

    What if one question sparked your next big change and growth moment? And what if we can do it in a single session?

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