The short and sweet version:
Jennifer Bailey is… a strategist, change agent, What Matters Most 365™ coach, life design expert, entrepreneur with a penchant for brainstorming, inspired speaker, lifelong learner, collector of reinvention stories, catalyst for change, thinking partner, blogger, CEO of her own happiness, founder of Grace Street Group, and dark chocolate enthusiast.
The expanded version:
A passionate advocate for intentional life design, Jennifer is the architect behind What Matters Most 365™. She has facilitated change—both personal and professional—for hundreds of individuals using this profound and practical approach to life planning.
Jennifer believes there’s greater meaning, real purpose, and lasting happiness to be found in intentional living. In other words, actively and intentionally designing the next year of your life rather than letting it simply unfold by default.
Through What Matters Most 365™, Jennifer works with individuals to focus their attention, intentions, and actions on what matters most. Jennifer’s highly doable, yearlong approach avoids pie-in-the-sky promises and brings these lofty goals down to earth with an unparalleled combination of structure, support, encouragement, momentum, and accountability.
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 usability 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 founding of Grace Street Group—and the development of What Matters Most 365™—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: a life of authenticity 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…
All the best,
I consider myself a grateful person. I made a decision years ago to actively choose my mindset when I wake up in the morning, and an attitude of gratitude is one I like to keep front and center. I’m also very much a goal-oriented person. I make plans. I want more. I have ambitions, dreams… [...]
