Seasons of Leadership Mini-Series! My Seasons of Leadership Autobiography
Hi again, everyone!
It’s Tessa here, and I’m excited to offer another installment of Canopy’s Newsletter! We got such a positive response to our last newsletter about seasons of leadership and the accompanying Instagram live that I’m going to lean in and do a deeper dive on this topic. Over the next few weeks, I’m going to write a mini-series on seasons of leadership, each one partnered with an Instagram live on Wednesdays at 6pm EST. So tune in for those! If you didn’t get a chance to read the last newsletter introducing the seasons of leadership framework, I really encourage you to go back and check it out before reading this installment.
Today, I want to talk a little more about my own personal journey around this concept. I know I touched on this in the last newsletter, and my hope is that by unpacking my own experience of moving through the seasons of leadership I can provide a real life illustration and hopefully some inspiration to other leaders out there who may be experiencing similar challenges.
I also want to mention that sharing in this way feels really vulnerable! I am saying this out loud because I believe that it's important to name how uncomfortable stretching and doing something new can feel! Opening myself up in this way feels risky, and I also believe it's important to normalize the messiness of leadership, the failures, and the struggles. We all go through them, and when we keep those unpretty parts hidden, we do a disservice to future leaders. One of my main goals through all my work is to deepen connection and collective power, so I’m offering this part of my own story in service of that goal.
So with all of that pre-amble, here is my own autobiography of seasons of leadership….
I first learned about the concept of seasons of leadership from this article published in January 2022. At that time I was in a bad place. I had just run for city council in my town and had lost by a very narrow margin. The campaign was really intense and had a big personal cost for me on many levels. Canopy was also in a crisis, needing to pull in money as fast as possible, and we were at real risk of going under. I felt like I had given my all in so many areas that I cared deeply about. I had put myself in multiple front-facing vulnerable positions at once, and I could only see the ways that my efforts had failed. In the face of what felt at the time to be such intense and public defeats, I questioned all of my life choices and whether the future that I (along with many others) had been working so hard to bring about was even possible.
And then a friend sent me the article. It spoke so deeply to me on a personal level in that moment. It provided a way to understand what I was going through and to see my “failures” as part of a natural and expected cycle. It opened a way forward for me to envision possibilities beyond giving up. It allowed me to start to learn from the events of the past so I could rebuild for the next phase of the work from a wiser place.
I have come back to the article several times over the last 2 years and at different moments different parts of it have spoken more loudly to me:
The first round, I was solely focused on the individual component. What is my role in the movement for justice? What does it look like to do this in a way that doesn’t feel exploitative and like my skin is being peeled off each day? What does doing this work for life look like for me?
Later I circled back to the movement component of the framework - that our movements go through cycles as well. In the last ten years, I have lived through the ebbs and flows of several movements for justice that I have been involved in and committed to. In each of these movements I have found the swell of camaraderie, possibility, and hope that comes with an energized collective effort to be thrilling and empowering. And I have invested myself in each of these efforts and then experienced both the thrill of successes and the pain and bitterness of the missteps, failures, and internal struggle that comes as the movements try to navigate rapid growth, external push back, and divergent ideas of how to move forward from within.
And as my work at Canopy has continued, I’ve seen the cycles that organizations take. We increasingly have clients coming to us who have been investing in DEI for years and are feeling the struggle of maintaining meaningful efforts over the long term. Who are looking for ways to recommit, or deepen, or shift their approach but aren’t sure how to move forward. And this comes with a layer of personal confusion and despair from the people who have been driving the work forward. Putting us right back in the individual cycle.
Sometimes, my journey has felt like white water rafting down a raging river as I’ve navigated my passion and commitment to building a just future, my own role in the work as a person with race and class privilege, my formal and informal leadership roles, and my roles as an individual, partner, and a mother. As much as I’ve tried, I’ve never gotten it 100% right. The framework of seasonality of leadership allows me to see all of this from a 10,000-foot view. It mutes some of the sting that I have experienced on the ground. And just like it did when I was struggling in January 2022, it opens a glimmer of possibility and hope. It normalizes the experience. It allows me to say “it's not that I/we failed, I/we are just in a winter”. What a powerful reframe! It allows me to keep going.
So often with clients, I’m working to normalize the experience of how hard it is to do this work over the long term. As a coach who sees many organizations and individuals go through the cycles of leadership, I get to be the one who zooms out and says “Don’t despair! Don’t give up! This is normal! It's typical for us to see this!” And when I say those things, I see my clients' shoulders release just a little and breathe just a bit deeper. I see that glimmer of hope that there is a path forward open in them.
In a full circle moment (dare I say a cycle?!), I can now see that if I hadn’t have gone through my own winter as a leader I wouldn’t have learned this powerful lesson and then I wouldn’t be able to bring this new wisdom I’ve gained to my clients, and then I wouldn’t be able to meet this moment where so many of our leaders, organizations, and movements are in a winter - needing to heal, regroup, and learn from our past successes and failures so that we can rise again stronger and wiser and more strategic and more powerful.
I have so much gratitude to my friend (you know who you are!) who sent me the seasons of leadership article. It honestly changed my life. And as I keep doing this work and sending those ripples out in the world, I hope it gets to change many more people’s lives as well.
So that’s a part of my story. I’m curious how it lands for you.
In what ways does my story connect to your own leadership journey?
What possibilities come from normalizing the experience of “failures” and setbacks as we engage in equity and justice work over the long term?
In what ways does the seasons of leadership framework make you feel more hopeful?
I’d love to hear from you! Send a note and let us know what you’re thinking about in relation to seasons of leadership right now.
With love,
Tessa
