About Jennifer Bailey

The short and sweet version:  I am… a strategist, change agent, What Matters Most 365® coach, entrepreneur with a penchant for brainstorming, inspired speaker, lifelong learner, Life Design Expert®, collector of reinvention stories, catalyst for change, thinking partner, blogger, CEO of my own happiness, and dark chocolate enthusiast.

The expanded version: I’m the architect behind What Matters Most 365: Life By Design®, a create-what-you-crave program for making the next 365 days your best yet.  I have facilitated change for hundreds of individuals using this profound and practical approach to life planning.

I’m passionate about challenging people to think bigger, live with authenticity, and pursue the goals that inspire them—both personally and professionally. My sole mission is to help you dramatically improve your Say/Do ratio and take action on what matters most to you.

As a champion for intentional living, I believe in things like:

  • Reinvention is your right.
  • Waiting to be happy is the worst kind of wasted time.
  • Your worth and productivity do not equate.
  • The journey is at least as important as the destination.

Read my Manifesto and then tell me what you believe.


On a personal note: Years ago a friend gave me a poster she thought had been written just for me.  It read: “I laughed when I realized how many years it took to discover who I am…by first zealously exploring who I am not.

When I think about that poster, it takes me back to how many years I spent trying on careers, trying on geographic locations, trying on attitudes and outlooks, trying on different ways of showing up in the world…of zealously exploring who I am not.

At the very least, the poster takes me back to the technology consulting firm I co-founded in 2000 and sold in 2007, joining the acquiring company to manage the integration of services and grow the startup business unit.

There I was—in a secure corporate job making a very comfortable six‐figure salary.  I was respected in my profession, an expert in my field, and no longer at the mercy of the inevitable ups and downs of running my own business—and I was miserable.

I was competent, but not engaged. I was well‐compensated, but not inspired.  Once again, I found myself zealously exploring who I was not.

Suddenly, I had one of those catalytic, wake‐up moments where I knew I was not living my best life. The launch of my coaching practice—and the development of What Matters Most 365: Life By Design®—was my response to that moment.

Because What Matters Most 365® is all about identifying and living what matters most, I’m often asked what matters most to me.  In my case, what matters most is two‐fold: an authentic life where I can be myself 24/7 and a life centered on my passion, which is to help others find the path to their best life.

To what matters most,


Ways to stay in touch & up to date.

Sign up to receive a weekly dose of insight and inspiration.  For joining my community, you’ll receive my ebook, Power2: Improving Your Say/Do Ratio and Achieving Your Big Goal.

Sign up to receive a weekly dose of insight and inspiration. For joining my community, you’ll immediately receive a free copy of my ebook, Power2: Improving Your Say/Do Ratio and Achieving Your Big Goal.

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