Report date
May 2020
Learning Log

When I started my Fellowship journey, I was seeking a playbook with all the answers — answers to how to scale a social enterprise, how to be a confident and vulnerable leader, and how specifically to grow our organization to the level of impact our community needs. I looked to the East and West coasts for examples of large social enterprises and dug deep into their legal structures, earned and contributed funding approaches, leadership team structures and experience, and more with the belief that surely I could find the exact formula to repeat here. During that work, in a week-long social enterprise course at Stanford I realized that no one has all the answers. This realization around scaling social enterprise also translated to leadership lessons as well.

There is something both terrifying and freeing in realizing that we as leaders must write our own playbooks. What will be our guiding principles? How will we make decisions? How will we communicate? How will we show up during difficult times? Who will we surround ourselves with? I collected a stack of books during my Fellowship, based on recommendations of people I admire and respect, and even this wisdom could not tell me exactly how to navigate some of the hardest moments of my life, which have occurred in these past two years of my Fellowship. Only my inner wisdom, built from life experience and the amazing coaches willing to share their lessons learned, could truly be my guide.

Part of my Fellowship scope was intensive coaching with an executive coach, a mentor who accomplished the type of social enterprise scale I hope for, and a CEO roundtable. One of the most surprising moments was receiving advice and knowing in my core that it was not the right answer for me, my leadership style, or our organization. As a life-long people-pleaser who loves harmony that experience was new for me. I did not do what was recommended. At almost every turn, I have been faced with the realization that everyone “CEOs” (yes, let’s make that a verb) differently. With my goal of being a vulnerably confident leader, my approach sometimes looks very different than what “the experts” might say, but I know that on most nights, when I go to sleep as night, I acted in line with my ethics, values, and love for our community.

And on the topic of how everyone CEOs differently, I frequently had questioned if I was the right leader for our organization as we grew. In fact, I made a list when I became CEO of how I would know it was time to leave my position and bring in the next CEO. I knew I had skills to bring to the position, but I believed they were few and very specific, and that very quickly the organization would no longer need me in that seat. I failed to realize that just as the organization would grow and change, so would I. With the intensive coaching focus, at the start of my Fellowship, I underestimated how much I would grow and change. When I look at how I lead 3-4 years ago compared to today, I feel like our organization did bring in a new leader for how much I have developed. I always say we are all in on-the-job training at our work readiness training organization, and I am living proof of that, even in my position.

As I reflect on the last two years, I knew I was preparing and building my toolbox to scale and grow our organization, but I had no idea that I would also be navigating how to lead during a pandemic as I closed out my final months of my Fellowship. As feelings of unpreparedness crept into my brain, I realized that in reality I had spent the last two years in leadership bootcamp for these trying times. I had not anticipated that finding my preferred communication method that balances transparency, vulnerability, and directness would be applied while sharing thoughts during such uncertain times. It has felt as though this pandemic is a test of all of the lessons learned to this point. And while I won’t know my grade on the test for a while, I know for certain that I have done the best I could do, and I am reminded again that no one has the answer key. All I can do is ground myself in love, empathy, compassion, vulnerability, and humility as I seek to serve our organization and community to the best of my ability.