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Like most of us, I sometimes question what I am doing. Depending upon the day, my question may be: “Am I reaching all the people I could and, if not, what do I need to do differently?” or on a larger scale: “Should I simply do everything differently to be more “successful?” When your desire is to help make the world a better place, the desire to reach millions can creep in there before you take a deep breath, exhale, and then smile at how blessed you are.

Those thankfully rare moments cause me to look at some of the folks I am working with, what we are achieving, and how many lives are being changed over time. One woman in my 10-Month Program for Woman in Transition, quickly came to mind.

Patti had been a project manager for decades within the insurance world. Her success was in forming large, high-functioning teams. She was a natural. On the side, she had bought several homes as investments and rented them out. Her creativity loved the variety of apartments and individual homes, as well as the ability to work with numerous renters while providing beautiful homes to each.

When she took early retirement, she joined my new group that was starting, and said that she now had this great idea to open an Airbnb over her large garage and overlooking a large, gorgeous garden and needed help transitioning into “retirement” and a new possibility for income. She had long-term rental properties, but this new venture was a step out of the comfort zone. When I congratulated her expanding entrepreneurship, she laughed and said she was not a businesswoman just a woman with a hobby.

In my experience, changing our self-image can be the hardest part of growth, professionally or personally. Getting her to see that she most definitely was a Small Business Owner, took time and her willingness to risk seeing herself in a new way. It implied risk, commitment, investment, and a need to grow professionally and personally. By joining the group, not only did she get support for this transition on a personal level but being surrounded by other professional women in their own transitions, she witnessed others risking and expanding as well.

Because she no longer needed to do it alone, I could help her create a marketing plan. In contacting local colleges for parent weekends etc., local Chambers of Commerce, and more, she quickly got her Air B&B booked solid for 4 months out and spreading. She is now transforming some of the apartments, as they are empty, into larger Air B&B’s since she has so much demand.

In owning her “new” designation as a Small Businesswoman, after extensive research, pointed conversations with business and restaurant owners, accountants, and others, she is now also closing on a new breakfast/lunch restaurant in her town. Her love of teams has supported her in creating a powerful team of investors, workers, and support staff. It is a transformational experience, and one she is luxuriating in, even when exhausted or in fear. A former restaurant owner in our group has offered referrals for vendors, solid advice, warnings, and unlimited support.  Her choice to grow within small-group coaching meant she could minimize fear, wasted time, and confusion, plus get immediate feedback as she discovered her dreams expanding along with her skills and her team.

We can each clearly see that one gift of a small group is the shared wisdom and experience of the members. Initially, we may believe the formation is random yet there is always a reason they come together as they do. That for me is part of the joy and discovery. Why these folks? What are they going to learn? Share? Need?  As we all show up for her grand opening, the group’s connections deepen and the shared experiences remind each member, we are not alone and as a member said, “Life is so much bigger, the sun is so much brighter, and the days are so much richer.” That is success for every one of us.

Patti’s Airbnb is called The Garden Loft and her restaurant opening in Wallingford, CT in the fall is called The Bee’s Knees Bistro.


Dr. Dorothy’s life story of coming from an orphanage, being raised in the housing projects of South Boston, becoming a Catholic nun, an international airline stewardess, a wife, mother, graduate faculty member, Clinical Instructor at a Medical School, and so much more provides the perfect backdrop for her message of joy, humor, passion and faith as the necessary tools for life.