Stefan Jackson of Bridgton, Maine, was born in the North Beach neighborhood of San Francisco in 1959. He went to Amherst College, graduating in 1981. He later attended the University of Pennsylvania Law School, earning a degree in 1995. He became a Wilderness First Responder and earned a wilderness instructor certification from NOLS (National Outdoor Leadership School). Jackson is a longtime member of the advisory committee for MaineCF’s People of Color Fund. Photo by Thalassa Raasch/MaineCF

How did you come to live in a cabin in Bridgton, Maine?

In July of 1995, in Lander, Wyoming, day two of my job as public policy manager for NOLS, I met Laura Ordway, third-generation Mainer and a veteran NOLS Wilderness Mountaineering and wilderness medicine instructor for Wilderness Medicine Associates (WMI). In 1998, Laura moved back to Maine, continuing to instruct courses for NOLS, guiding for the International Mountain Climbing School at IME (International Mountain Equipment) in North Conway, New Hampshire, and leading wilderness medicine courses for WMI out of Bryant Pond, Maine.

Laura and I wed in September of 1999. Since the 1960s Laura’s family have been owners and directors of Winona Camps, a summer camp for boys in Bridgton. After winterizing one of Winona’s cabins, we moved in at the end of 1999 and have lived there ever since. Laura and I raised our two daughters, Stefanie, 16, and Jacqueline, 12, there on the shores of Moose Pond, amidst 550 acres of mixed pine and hardwood forest.

Laura and her brother Spencer are now the owners and directors of Winona Camps. Their family were the second owners and directors of Winona Camps. Laura and Spencer are the second generation of Ordways to run Winona, as the camp heads into its 111th season.

You have been involved with helping to encourage diversity in environmental organizations, including The Nature Conservancy and Trout Unlimited. What does this entail?

I bring diversity, equity, and inclusion work to nonprofits focused on nature-based conservation, stewardship, and education. This entails coaxing, guiding, coaching individuals and staff to live and operate by and up to their values. And sometimes it’s getting them to live and operate by and up to their aspirations.

Most nonprofits in the nature conservation and stewardship sector, particularly the widely venerated organizations founded in the 1950s-1980s, are driven by mission and pursuing their vision. Unfortunately, they often develop an organizational culture wildly untuned to patterns of dominant power and privilege and their fundamental role in systemic oppression. What training entails is finding individuals and organizations that are willing and able to do “forever work,” those who can take satisfaction in putting in a lot of effort to make tiny, fundamental changes that can lead to gargantuan effects.

So diversity training entails learning to enjoy pushing rope uphill: painstaking, high failure-rate work on a molecular, atomic level – and being happy with long-term success of altering strands in organizational DNA.

What is Natural Difference, LLC, and what inspired you to found it?

Natural Difference, LLC is my omnivorous consultancy. My services? Diversity, equity, and inclusion (DEI); mediation; nonprofit management; handyman. DEI (also called EDI) work is both soul-expanding and soul-crushing. My variety of services is my salvation, my means of preventing burnout from DEI work.

I was inspired to found Natural Difference, LLC, because I have a set of skills, experience, education, and training, that allows me to guide and coach individuals and organizations that have the values, intention, and resources to do their own DEI work, yet are unsure of where or how to commence action. I realized that when I ran DEI programs and projects myself, I invested too deeply in the outcomes of those programs and projects, and my singular efforts propagated one set of ripples. By coaching others (I have a bunch of experience as teacher and coach) who lead and do the program and project work, I can increase my impact and the effectiveness of my contribution to neighborhood.

You have been a longtime advisor to MaineCF’s People of Color Fund (POCF). What impact has this fund had?

The fund’s impact has been twofold. First there is the seed money for the most vital and impactful projects and programs. Second, there are the POCF criteria, which include our assurance that our support not only goes to fund programs that benefit people of color, but that the organizations receiving funding have POC leadership, staff and board, and that projects funded arise from stated needs of POC. Receiving a grant from this fund informs other funders and the community served that to the best of the fund’s advisors’ ability to assess, these projects and the organizations carrying out the work are of, by, and for people of color.

Is there a specific grant that strikes you as emblematic of what the fund can achieve?

Tree Street Youth grew from an after-school program founder Julia Sleeper was running at the Trinity Jubilee Center, a People of Color Fund grant recipient that provides a broad array of family support services for new Mainers in Lewiston. POCF funding and organizational outreach and guidance to Tree Street Youth are emblematic of what the fund can achieve. Funding helped catalyze the creation of additional and focused services to underserved youth, which in turn helped Tree Street develop youth Street Leaders who inspire and lead peers to follow in those leaders’ footsteps. The People of Color Fund leverages every dollar and opportunity to benefit people of color in Maine.

What instrument do you play and what’s a favorite tune?

Voice and guitar. Singer/songwriter. Sam Cooke’s “A Change Is Gonna Come.”