Work with Me

Work with Jennifer Bailey @ Grace Street Group

Thanks for being curious about working with me.

I don’t know what your best life looks like, but you do. I’d be honored to be your thinking partner on the journey!

Right now, the best ways to work with me are:

What Matters Most 365:  Life By Design


What Matters Most 365:  Life By Design® — Here’s a simple fact:  Life is short and this—right now—is not a dress rehearsal.  If you’re not living the life of your dreams, what are you waiting for?  If you wish you had a reset button, this 4-week coaching program will help. Design your life, create what you crave and make the next 365 days your best yet.  Learn more about this life design program.


One-on-One CoachingOne-on-One Coaching — If you’re ready to get out of your own way and align your thoughts and actions with what you really want, let’s coach together!  My role as your thinking partner is to keep you forward focused and action oriented as you close the gap between where you are now and where you want to be.  Learn more about what to expect when coaching with me or find out about my coaching packages.


Jennifer Bailey is a Myers-Briggs Certified PractitionerMBTI® Personality Assessment — I’m an INFJ, and embracing that has made all the difference.  Ever wonder what would be possible if you embraced your unique personality?  You’ll be in good hands with the world’s most trusted personality assessment.  Insightful and thought provoking. Reliable and valid.  Get ready to shine a light on your strengths and pull back the curtain on your blind spots.  It’s all good as you gain insight into who you are and why you do what you do.


Espresso CoachingEspresso Coaching — You + Me.  35 minutes.  Coffee won’t provide the only jolt.  Short and sweet on your calendar.  But long on impact, deep on clarity, and fresh on perspective.  Are you grappling with a challenge, dilemma or question?  Could you use a shot of clarity, inspiration and motivation?  Do you have 35 minutes to move forward?  If you answered “Yes, Yes, Yes” then let’s meet up for an empowering coaching conversation.


Tolerations Tolerations MicrocourseMicrocourse — The average person tolerates between 500 – 1,000 things every day. Just think about that! We know for a fact tolerations take up space in your mind and drain your energy.  If you couple that with tolerating 500 things a day, is it any wonder you feel stressed out, overwhelmed, frustrated, distracted, irritable, drained—in short, that you’re not living your best life? Invest in yourself by becoming toleration free.