Closed Chapters and New Seasons

Lessons to Rewild Life and Leadership

Hello Wild One,

Spring has arrived and it finally feels appropriate to exchange joyful ‘Happy New Year’ salutations. In the depths of winter, the year felt incomplete and unresolved with so much still to process, grieve, and let go both personally and collectively. The landscape of the past twelve months was scattered with metaphorical mountains, emotional wind storms, vistas of possibility, and an abundance of joyful sunshine. It was a year of finding new edges and challenging whether I could really walk the talk of new ways of being.

In the years before my unlearning and rewilding, I was content to begin the year on January 1st and allow the highs and lows of the past year to be washed away with a fresh planner. The realignment with cycles of nature has allowed me to extend my processing into the winter months to more fully unpack the wave of energy that consumed me and reorient before the next one hits. This past year in particular was a series adventures and misadventures in motherhood, work, family, home education, friendship, and community that demanded my full attention and review over the slow, barren winter months.

As I made sense of the year across several journals and notebooks, a few themes bubbled to the top: conflict resilience (I need to stop avoiding it), releasing perfectionism (does it end?), iterative growth (nothing is exponential), and trusting myself (stop seeking validation). There was one area of my life where the lessons were most present: my work life. I made some big decisions that weighed heavily on me the past year: moving out of entrepreneurship, into a non-profit executive leadership role, and ultimately leaving to return to my own lane. The journey was humbling, expansive, and left me with a series of hard won lessons and powerful truths. Wisdom to carry me into a new season and a lifetime.

Evolving Relationship to Ways of Working

Before I began rewilding and unlearning, I approached my career in a very traditional and linear way: my goal was to advance quickly down a path and up a ladder that could be easy articulated and understood on a resume. I nailed my performance reviews, made very few waves, and aimed to be as self-sufficient as possible. It all felt tidy and controlled. That narrative began to unravel when I left corporate for the road less traveled; I began to see potholes as learning opportunities and overgrown shrubbery as generative chaos. I was sense-making for myself, knowing it made no sense to other people. The career choices I made this year forced me, yet again, to grapple with whether the perception of me was more important than the experience of living my one wild life.

Last spring, I began an executive leadership position at a storied 50 year-old retreat and community center here on the Whidbey Island. After years working in adult learning and nature-based programming, it felt divine to be part of an organization that began as an educational community and evolved into a 106 acre sanctuary in the woods. The team operated with a unique shared leadership structure, which I saw as an important pathway to collective liberation within institutions. The org development nerd in me needed to know what it was like to work in an alternative structure. It seemed as though my worlds had collided and I could engage in work of unlearning, reimagining, and rewilding in ways that could impact many more people.

The nourishing forest, mysterious gardens, and vibrant bird song spoke to me. My co-leader and team dreamed of beautiful ways this place could hold our visions of community. What I did not expect was to have old ways of being at work awaken from their deep slumber in attempt to help me. The abundant futures were met with the drive to do and prove that places like Amazon seeded deep in my belly. All the healing work I had done to tame my ego, hold complexity and paradox, and find peace in my body seemed to evaporate. I knew that growth was uncomfortable, but learning in such a visible way stretched me beyond what I had imagined. Needless to say, class was in session.

Discomfort is an Opening for Meaningful Learning

In the midst of a big life lesson, it is hard to appreciate the wisdom and learning that is being woven into our being. The stretching creates new openings that rewrite our understanding of ourselves and the world, allowing for new connections and emergent possibilities. This years lessons were served up by a host of teachers: team members, land stewards, world-renowned liberation practitioners, edge walkers, community weavers, and more. Each of them reminded me that the work of liberation is a practice that requires attention and commitment—every single day.

As I continue to deepen my own practice, I share lessons as a way of learning out loud, to honor my own humanity, and inspire our collective growth. It is an act of resistance in a world that demands we have all the answers, achieve success alone, get it done yesterday, and do it without breaking a sweat. May we all find the courage to overcome divisive and oppressive ideals in our professional constructs as we seek to build new worlds, remember our connection to all that is, and ultimately set ourselves free. Here are some of the lessons that I am reflecting on from this last chapter:

Perfection thwarts progress: I can’t tell you how many times I thought I pulled out the root of perfectionism, only to have this stubborn weed return again, disguised as something helpful like safety, discipline, or responsibility. At this point, it seems this pattern is so deeply embedded in me that I will be deprogramming it for the rest of my life. When it comes to my work life, I watched myself set unnecessarily high standards for myself, be the first to criticize myself when I missed mark, and descend into inner turmoil when I made a mistake. This year has highlighted just how exhausting and absurd it is to believe I can and should stick the landing on the first attempt. In the year ahead, I commit to being a little more human by embracing mistakes as a necessary part to learning and trusting the world has space for grace.

Healthy conflict amplifies connection: Bless the people in this world who have a healthy relationship with conflict and regulated nervous systems that allow them to sit in the tension. In my lineage, tension was something that was avoided, ignored, or met with placation. However, this year was a poignant reminder that learning to face interpersonal struggle in healthy and generative ways is an essential practice. I have developed a deeper appreciation of conflict as a passageway to deeper understanding and connection. Each point of conflict created an opportunity to reflect on parts of myself that were hurt or broken. As I learned to be curious about the pain and the instinct to resist, I softened just a bit more. I saw something different in myself and the stories I told myself about this pain. As I move ahead, I hope to meet tension with the curiosity, creativity, and tenderness that it deserves.

Collaboration heals the collective: There is an interesting dichotomy in the corporate world around encouraging teamwork but rewarding individualism.  In my soul, I have always wanted the team to be the center of work, and there is nothing like a shift into an alternative shared leadership structure to highlight just how much we defer to individual and hierarchical power arrangements. Diffusion of power and decision-making across many people is incredibly challenging to say the least, but there is also something beautiful about it. I got to witness a team of people redefine how to work together and saw some deep healing in the process. People communicated better, learned to people-please less, gave and received feedback, problem-solved more effectively, coached each other towards solutions, and made more space for self reflection. It is painful and frustrating—but nobody said that healing was easy.

Rewilding is a Lifelong Practice

There was a season of my professional life where I would look back at an experience like this and only see the things I did wrong, the ways I let people down, or things I could have done better. The coulda, woulda, shouldas. I would have felt guilt—even shame—for the missed expectations and failing to meet my own impossibly high measures of enoughness.

I know rewilding has shifted me in some foundational ways because I can honestly say that I am grateful for each of these lessons, as painful or difficult as they were at the time. Each one represented a pattern that needed to be unlocked and this season presented me with the exact people who carried the keys. They allowed me access to deeper understanding of myself and how I relate to the world. I am also proud of myself for taking on a challenge and doing it with as much grace and skill as I could at this season of my life.

As I look ahead, there is one throughline that I am eager to follow into this next season: building resilient learning communities. If we are to embrace hope and possibility in troubled times, it is essential that we learn to be adaptive, learn how to care for one another, learn how to share our resources, and learn how to fight with love and integrity. I have much to say on this and am eager to unpack it with you all in due time.

Until then, drop a comment or send me a message with your greatest lessons from this past season. What are you taking with you and what are you leaving behind? What have you outgrown and what are you stepping into? What is the vision you hold for this next season of rewilding?

I appreciate your reflections and look forward to hearing from you. Until next time, take care, be kind, and talk soon,

Hillarie