My search for the truth of philanthropy is a never ending journey that continues to open, unfold, and inform.

Sense of Belonging

My sister returned from her sailing travels around French Polynesia with wonderful tales and a basket full of fascinating items. She pulled out a hand woven, grass bra with a huge, pink, plastic flower resembling a marigold right in its center. She asked, “Do you know what the word for ‘bra’ is in Vanuatu? It’s ‘Basket Belong Titties’!  Belong means ‘with’ in their culture’s creole.” I looked at the handmade bra and saw that without the pink marigold the bra would not function. The pink marigold, the ‘belonging’, conveyed with, connection, and support.

Belonging is at the center of my personal wound and the center of what it means to be human. We are social creatures and being connected and supported is central to our identity and how we function individually and as a community.

Illustration of tribal family, with the connectedness of community

Being connected and supported—is at the center of our sense of identity and how we function both individually and as a community.

Family Roots

My family’s story as immigrant, Canadian-Scots sheepherders was tightly woven into the community where my grandfather, my father, and I grew up. My father ran the family ranch and derived his sense of belonging from the land. He was a community member on several levels, but his sense of identity and place always came from the land.

My mother was the opposite. She derived her sense of belonging from our family name, and supporting larger community causes. Mom often told me that for people in our position it was extremely important to give back. I admired her sense of duty to others. Yet, from my point of view, the main reason she volunteered was because the experience connected her to her voice, her power, herself.

My belonging in the family was in question from the start. Mom frequently let me know that I was ‘different’…too sensitive. I was different, but I didn’t have a name for it until much later in life: right brained. Logical thinking did not come naturally, nor did reading and writing. A family standard was set and I had no idea if or how I would ever reach it. Given my family, I was supposed to be on the inside. Given my nature, I was on the outside.

My farm community did give me a special sense of place until the age of 10 when my mother and father decided to move my sister and me to the city. It was a difficult move, and I felt my pink marigold shrinking.

Illustration of the Aly McGregor as a kid feeling disconnected from family

Given my family, I was supposed to be on the inside. Given my nature, I was on the outside.

In Search of Belonging

My inability to connect to what was close to me fueled an interest in belonging to that which was far away. Instead of belonging in one place, could I belong in many? So, I traveled. I found beautiful experiences of belonging and connection in far away places. I found an equal number of frustrating experiences of non-belonging in those same countries. The tension between the two poles drove me into a deeper, richer conversation concerning my place in the world.

When I was 25, I came home from living and working in Asia. Again, I was trying to figure out how I belonged—this time, in terms of employment. While talking to Mom about my inability to find a career, she suggested I become a philanthropist. I loved the thought of “getting out into the community,” because it reminded me of my rich experiences with people, but I hesitated to join an established group that did charitable work. The work was “good” but there was a sense of “us vs. them” in the action. “We belong and are going to give you a helping hand so you can feel like you belong too.” It seemed artificial. I often felt I had more in common with the people being helped than with the community giving the help. Yet, there was something about Mom’s advice that spoke to me. I held on to the moment, allowing it to inform my actions down the road.

Illustration of Aly McGregor spinning a globe, in search of belonging

I often felt I had more in common with the people being helped than with the community giving the help.

Educating Others and Myself

In 1990 I lived in an artist colony in central Mexico. In this special town, I felt a great sense of belonging and realized that my learning problems came from my artistic, right brain. I landed in a place where the rhythm and internal swing matched my own. The support of my teachers, friends, and community lead me to a place where I felt my internal, creative potential. I wanted to teach others how to reach in, grab, and pull out from their own creative space. I ended up teaching creativity in a school for the deaf and learning disabled. The school was IREE and the director, Ceci Escobar, gave me a place to test my ideas and grow as a teacher and as a person.

My time with IREE was fun, creative, and full of vision; exploring ideas that seemed impossible. One of these ideas came when Ceci handed me a pamphlet for a symposium on deafness held in Austria.  I had a flash of insight and said that I would send her to the symposium. Ceci asked why she would use the money on travel and not on the school?” “Ceci,” I said,  “I know you will meet someone who will be so impressed with you and the story of IREE that they will come to the school and help.” I punctuated my certainty with, “If you want your school to grow, you have to have vision.” Ah Ha!

Ceci went to Austria and met a Danish hearing specialist who was so fascinated by Ceci and the story of IREE that she visited the school and brought two audiometers with her. The school, for the first time, was able to measure the students hearing and offer their testing services to the greater community, allowing them to make a little extra money on the side. Wow—the power of vision manifested!

Illustration of Aly McGregor teaching creativity to deaf kids in Mexico

I ended up teaching creativity in a school for the deaf and learning disabled.

Finding Philanthropy

From my stroke of insight, to Ceci’s trust and travel, to the Danish women’s visit the whole experience was exhilarating, transforming, and magical. My reason for teaching was to help people find their creative voice and potential. This experience taught me how philanthropy-partnership fulfilled my desire on an even greater scale. Supporting vision, potential, creativity, and partnership was a life affirming action and oh, so powerful. It bolstered IREE and gave me an overwhelming sense of belonging to a community where my voice mattered. I wanted to do it again!

As I was finding my philanthropic feet under me, I went through another shift in connection with the passing of both my parents. I was left with two very big questions, “Who am I now?” and “Where from here?”  I remembered the moment of Mom’s declaration of what my work in the world could be as a philanthropist. I decided the most generative use of my inheritance was to create a foundation giving to causes close to me: children, education, and international issues. Above all, the heart of my philanthropic mission was to support projects with vision.

My foundation is 17 years old, and I have learned so much! In creating this web site and reflecting on my experiences as a donor, I re-witness the powerful, complex acts of giving and receiving. I am more in awe of the change to my internal world than in my ability to change the external world. I learned the first experience ignites me and gets me into the game. The second and third experiences present obstacles that challenge me to go deeper, to ask better and more authentic questions of myself and of others.

Illustration of Aly McGregor in conversation about creativity and giving

The heart of my philanthropic mission was to support projects with vision.

Exploring with Vision

The greatest revelation, however, is how my very basic human wound of belonging is at the core of my impulse to give and grow. Creativity and vision ask me to go to the outer edges of what is known to bring in what is new. If I belong to just one community all my life, I limit my capacity to grow. As Joseph Campbell wrote in expressing the archetype of The Hero’s Journey, it is the person who leaves the village and sails into the open waters of the unknown who finds a new treasure/power within him/herself that becomes a gift of vitality for the community. “There is what I could call the hero journey. The night sea journey, the hero quest, where the individual is going to bring forth in his life something that was never beheld before.”  ‑Joseph Campbell

I believe the decision to become a donor is the single greatest, growth-producing idea I’ve ever had. As I continue my journey, I find that sometimes the pink, plastic marigold is easily touched and held. Other times it is elusive. It is, however, the idea that the marigold exists and informs that perpetuates my curiosity and drives me to look for deeper connections within myself and within my partnerships.

Illustration of Aly McGregor on a journey

There is what I could call the hero journey. The night sea journey, the hero quest, where the individual is going to bring forth in his life something that was never beheld before.”


— Joseph Campbell

Infographic showing balance of self and community
Infographic showing balance of self and community

Take a look in the resources section to find books that are my touchstones filled with ideas, philosophies, and practices that spark my spirit and show me how to do a deeper dive.