10 reflections from a first-year CEO
By: Josh Feldman, R&R Founder & CEO
This week we mark the first birthday of R&R: The Rest of our Lives. So I am taking the opportunity to look back and share some reflections on starting and running a social enterprise. Here’s what worked:
Step up: The world needs leaders to act - to innovate by applying good ideas. Sometimes those ideas already exist, but need leaders to focus on them. R&R was inspired by 20 years of research demonstrating that sabbaticals strengthen organizations and refuel leaders and boards.
Listen: Listening is a leader’s greatest strength. Cultivating a practice of deep and active listening and learning is the foundation on which everything else rests. R&R’s rest-focused work grew out of a need expressed during 100+ initial conversations where I listened to the pain, struggle and burnout that nonprofit workers are experiencing.
Generosity and abundance: Helping resources flow. Offering what I know freely and transparently. All boats can rise together. When Radical Reset launched its fundraising campaign, I was honored to encourage R&R’s base to donate to their campaign resulting in a large gift for Radical Reset and deepening our organizational partnership.
Reflection turns experience to education: Taking the time to look back is valuable, and I do better work when I release myself from false urgency. This iterative process helped R&R design and manufacture a deck of rest-based cards, now in a 2.0 version, which has added significant value to its recipients.
Internal and external consistency: Ensuring values and mission align with the organization’s leadership practices and internal culture is essential. After completing our first grant cycle, I closed our organization for three weeks in September to rest and refuel our minds and spirits.
Take a break, even in start-up mode: Breaks between meetings, days off, and vacations all make our work more effective and sustainable. I look to organize many of my meetings as 25 minutes long, leaving breaks before the next meeting. Even a couple of minutes is game-changing to the flow and effectiveness of the day.
Owning privilege: I am seeking to create a more equitable, fair and diverse leadership pipeline by using my privilege. Examples include representation in public speaking opportunities and our advisory body, and making equity a driver of our granting work. Often, this manifests as intentionally stepping back and supporting others’ leadership.
Learning to live with the unknown: A weekly and sometimes daily practice for me is acknowledging how precarious it feels to run a startup. Like a tiny boat in the ocean, we are at the whims of the weather. I’ve learned to be nimble and let the current inform our actions. I return over and over to emergent strategy for wisdom. On the more challenging days, I walk around the block to reset and ground myself in the possibility of great multiple futures.
Regeneration: R&R is focused on creating a relationship to work that refuels and honors each worker. My life being more than my job is an important part of this work. I play and let go. I seek out nature to reground me. I plant things and hope they grow.
Gratitude: This has been a year of thanks. To the universe for providing the opportunity. For my co-worker for building this with me (thanks, Rachel!). To our donors for providing the financial resource. To our advisors for sharing their wisdom. To all the other leaders working towards a better relationship with work and rest. When I don’t know what to do next, I can always return to who I should be thanking. Gratitude is an infinite resource.
These reflections are not ideas about being in a particular position, but rather the honor of reflecting on building things. A great leader, Ruth Messinger, once told me that it matters less the issue I work on but more if I can overcome the paralysis of choice and commit to repairing a broken world. And today, I asked myself, would I do it again if I knew the mountains that would need to be climbed? The humbling stumbling along the way? Yes, in a heartbeat.
I’d love your reflections - what are the drivers for your leadership as you look to build things and make the world a better place? What did I miss that works for you, week after week?