Let’s take a little journey back in time to the year 2000. George W. Bush was elected President of the United States, the world’s population reached six billion, and the internet was quickly becoming a huge part of our everyday lives. Activists, organizers, and nonprofits seemed more important than ever.

But when Rockwood’s co-founders Andre Carothers and Robert Gass looked around, they saw movements that were struggling with their sustainability. There was a lot of passion and dedication, but there was also infighting, overwork, competition, and burnout.

So they sat down at a kitchen table and began creating what would eventually become the first Art of Leadership.

Fast forward to today: that curriculum has evolved and expanded, and our network has grown to over 5,000 alums and counting. We’re helping to sustain leaders over a lifetime of work in a wide variety of sectors, including racial equity, . We have partnered with dozens of organizations to increase their effectiveness and power, and we have trained leaders in the Middle East, Asia, and Oceania.

We’ve learned a tremendous amount these past 15 years, from our own struggles and triumphs as a nonprofit, and from all of you – our alums, partners, and friends. In honor of Rockwood’s 15th birthday, we’ve put together a list of some of those lessons, in hopes that we can share a bit of that wisdom & know-how.

15 Things We Learned in 15 Years

1. Making time outside of work is not only possible, it’s essential. One of the main causes of burnout is working endless hours – staying late, skipping weekends, trying to squeeze email time into vacations. At Rockwood, we encourage our staff to get plenty of rest, relaxation, and time with family and friends, which helps alleviate stress and has actually made us more efficient.
2. Meaningful relationships are more powerful than transactional ones. We’ve learned that partnerships built around connection and community have more potential for longer-lasting change because they are often about people, as opposed to specific projects or tasks. This means they don’t just end when a policy is changed or a case is won, instead continuing to generate actions and activities for many years.
3. Healthy, sustainable organizations are inclusive. At Rockwood, we are thoughtful and intentional about who is on our staff, board, and trainer team – in terms of race, gender, and movement (to name a few). This approach has made us more welcoming to participants, which in turn has expanded our network and helped us create stronger programs for current and future leaders.
4. Embrace adaptive capacity. We’re creative and flexible when it comes to decision-making and problem-solving, making us a resilient organization and staff. This has helped us weather tough financial moments, and get better at what we do by learning from failures.
5. Authenticity makes leadership universal. Sharing ourselves – putting our personal stories into our leadership, and being open and honest with our colleagues – helps us, as leaders, to connect with more people, no matter what “leadership style” they may work with best. This strengthens our external partnerships and our internal relationships, and helps us get more done.
6. Working harder is not better – less is more. Social change movements seem to prop up busy, overworked leaders as a good thing, but we’ve learned that being “busy” without a vision to guide you can create a lot unnecessary work, while also increasing stress. Rockwood’s staff uses tools to stay aligned with our vision and make sure that our work is advancing that vision.
7. There’s value in courageous conversations. Difficult conversations are just that: difficult. They make us want to avoid them, but at Rockwood, we’ve learned that they make us better partners and collaborators, and more productive in our work.
8. Feedback is crucial. Not only do we learn from feedback (even when it’s positive!), but giving clear, direct, and regular feedback across teams reinforces our culture of commitment to each other. Knowing that Rockwood welcomes honest and kind feedback means that there is always space to ask questions, offer suggestions, and grow closer as colleagues.
9. Connect the personal to the work. Leadership starts at the core of who we are, with the unique gifts we each bring to the table. When we know what that is, we can make clearer, stronger choices about our life and work so that we stay challenged, fulfilled, and motivated.
10. Intentional partnering across sectors increases impact. It’s so easy to get stuck in our silos and find value only in our own sectors or issues, but we’ve seen amazing things happen when people partner across sectors. Our alums who created unlikely partnerships have done incredible things and created long-lasting change.
11. No one leads alone, and no one ever has. There are many people who influence, shape, and support each of us as leaders. The people we surround ourselves with – co-workers, mentors, friends, and family – form an important, nourishing network that we rely on to create powerful change.
12. Sharing power is more satisfying for the whole. “Teamwork makes the dream work” counts for Executive Directors and Presidents, too, even though those positions often feel like they can’t (or shouldn’t) need help. The entire staff of Rockwood is called upon at various times to share their expertise and experience, and that trust keeps us all motivated. It also frees up our CEO to focus on the tasks only she can do as head of this organization.
13. It’s important to take risks and leaps of faith. We’ve never been in this time before, and what got us here may not work in the future. We stay ready and willing to try new things to create change, no matter how scary that may be.
14. Leadership is a skill that can be learned and developed. Many people think of “leadership” as something that comes after years of experience in a management or supervisory role, overseeing a staff and a budget, something tied to positional power. Our view of leadership at Rockwood is more open; we believe it’s a skill – like painting, running a marathon, typing – and can be practiced and exercised by anyone, in any role, at any moment it’s being called for.
15. Leadership can be joyous and satisfying. Getting something done well, with those you care about, and with clarity and meaning – that’s the essence of leadership.

Like this list? Download the free ebook version for motivation & inspiration!

What are some important lessons you’ve learned through your work? Share them with us!