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Leaving Your Social Startup

For more than 30 years, Echoing Green has identified, invested in, and catalyzed nearly 1,000 leaders dedicated to social and environmental progress all over the world. They come to this work as organizers, activists, educators, scientists, farmers, lawyers—each who were compelled to act to create transformational change in their communities. As founders, their solutions pinpointed root causes of systemic injustices, and these founders put their passion, skills, resources, and networks into getting those solutions off the ground. Being a founder of a social enterprise requires purpose, sacrifice, and whole-hearted commitment. But what happens when it’s time to leave the organization you founded?

Assess Your Own Leadership Journey

Like evaluating a role at any organization, founders must continuously analyze their fit at their company. Are they equipped to grow the company as the leader their organization needs? Do they still enjoy being the head of the organization? Reflections like this often happen organically as a founder faces changes personally or professionally. For a lot of entrepreneurs, strategic planning processes can lead to this examination.

Laura Weidman Powers, founder of Code2040 and Echoing Green’s head of impact, was undergoing strategy planning at Code2040, which led to reflections about committing to stay with the organization through their next strategic plan. She wrote about her thought process:

“If I was going to design Code2040’s new strategy, I was going to stick around to execute on it—a three- to five-year commitment. So I started to ask myself: Was I the right leader for Code2040 for the next five years? Was Code2040 the right place for me for the next five years?”

Those questions, coupled with other personal and professional factors, led to Laura planning for her succession before this new strategic plan took off.


More about Laura’s Transition from Code2040 on Stanford Social Innovation Review

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Similarly, as Sam Pressler’s organization, Armed Services Arts Partnerships (ASAP), was preparing for growth, he realized that he may not be the right person to lead ASAP through its next phase. Sam shared his thoughts in his announcement to step down as executive director:

“The ASAP community deserves an Executive Director who can lead the organization’s next chapter and build upon our early-stage success with vigor and enthusiasm. And, I am ready to catch my breath, process the last four years, and assess what’s next for me.”

Consider How You Fit into Scaling

Plenty of founders remain with the organizations they founded for decades—and many are perfectly suited for long-term leadership with their startups. But some are serial entrepreneurs with a need to launch their ideas one after another, and some face burnout from being the sole CEO and need to step back for a change in day-to-day responsibilities. Some are inclined to learn how to grow and sustain programs while supporting leaders at other organizations. Others may simply be in a different place than where they were when they started their organizations.

After launching ASAP as an undergrad and getting an Echoing Green Fellowship straight out of college, Sam realized that, while he had great success getting ASAP off the ground, he wasn’t necessarily the best person to continue leading the organization.

“I’ve come to realize that effective nonprofit management is neither a marathon nor a sprint—it’s a relay.”

“I’ve come to realize that effective nonprofit management is neither a marathon nor a sprint—it’s a relay,” he wrote. Sam also questioned his own identity while leading ASAP.

“My identity became very much tied to a population I was not necessarily a part of. I was this civilian non-veteran running the largest veteran arts organization in the country. There was a benefit to that because it gave me emotional distance when necessary, but there was a downside because I felt I was always being asked to justify why I was doing it,” he said.

Rose Wang, co-founder of Chirps, struggled with uncertainty as CEO all the time. Similarly to Sam, she started Chirps right out of college, and with very little work experience and a lack of expertise about the food industry, she continually faced self-doubt.

“I’ve only ever been a CEO, and I want to start at the bottom somewhere else, so I can learn and grow and eventually be the best CEO I can be,” Rose shared when she parted ways with her startup.

Rose knew it was time to depart Chirps five years in, as the organization headed into its next chapter, and she was ready to take on new challenges. Viewing management in a way that ensures the right leader at the right time can be helpful in long-term planning. That kind of foresight is essential for both the organization’s and the founder’s growth.

Examine the CEO Role

Taking on a CEO role at a social startup is a major learning opportunity when it comes to overseeing management, fundraising, operations, marketing, and so much more. However, most don’t realize that the role can also stunt a leader’s growth in other ways.

After Rose launched Chirps, she found that having no real structure or authority figure to check her decisions was exhausting.

“I constantly questioned whether or not our mission to change the food system could have been done bigger and faster with someone more experienced at the helm,” Rose shared. “Yes, there were accelerators and generous advisors and mentors–but it’s not the same as having many experienced people around from which to learn. Usually, doubt was overpowered by momentum–a new partnership, progress on the product development, etc. But about five years in, that feeling of doubt didn’t go away.”

Founders start their organizations from a place of passion. But sometimes that passion isn’t enough to fuel the CEO in their role. A major part of the job is to be fully immersed in bettering the organization all the time, which has its pros and cons. Laura considered this when weighing whether to continue as Code2040’s CEO or step down.

“There is a (well-justified) feeling amongst founder/CEOs that you have to be committed to the point of evangelical about the organization in order to successfully lead it, particularly to attract the resources needed for it to thrive,” Laura wrote.

This “all in” attitude is what drives social enterprises forward, raises money, and gets CEOs and founders on stages—but that kind of pressure can lead to burnout. Additionally, while serving as a CEO can be invigorating and rewarding in some ways, it can also be tiresome, lonely, and sometimes even ungratifying in other ways.

“When you’re everyone’s boss, you have no peers at work, no one with whom you can let your guard down, no one to vent to,” Laura wrote. “And, as the ultimate people manager, the overwhelming focus on guiding others rather than on creating work product myself meant that I never felt I could truly take pride in the organization’s accomplishments as my own, even as I took responsibility for every misstep.”

Prepare for Succession Even Early On

“Our goal for ASAP has always been to build a sustainable, robust organization that is bigger than any one person or one program,” Sam wrote.

Founders should always be thinking long term. But when you’re getting an organization started, the least obvious task is to think about your succession plan. However, as you are building out your programs, teams, board, and clientele, it’s never too early to begin thinking about what comes next and how you as a person and a leader will factor in. It also means sharing the load of work that is constantly on the CEO’s plate.

“When you’re spending so much time trying to keep things going and ensuring that, no matter what happens to you, this organization needs to last because of the positive impact it has in people’s lives—that leads to burnout because there’s always more work to do.”

“When you’re spending so much time trying to keep things going and ensuring that, no matter what happens to you, this organization needs to last because of the positive impact it has in people’s lives—that leads to burnout because there’s always more work to do,” Sam said.

It took organizational challenges for Laura to realize that leading from behind and encouraging her team to step up was a tactic that would serve Code2040 in the present and future.

“I realized that I did not know how to lead from out front to get us through the challenges we were facing, and so I made the choice to try to lead from behind,” Laura wrote. “I sought out several people across the team and asked them to step up to lead us at that moment, with my support—not because of any authority outlined in their job descriptions, but as teammates committed to the future of the organization.”

During this time, it became clear to Laura that the future of Code2040 was no longer tied directly to her leadership. She had built and equipped a talented team prepared and empowered to take the organization to new levels.

Take Comfort in the Discomfort of Leaving

Parting ways with any job is life-altering—and it’s important to acknowledge that loss. Launching an organization is a massive undertaking into which founders essentially pour their whole lives. Coming to terms with saying goodbye to what you built from the ground up, the teams you created, and the constituents you are serving is a significant milestone. Mentally preparing for and appreciating this step is helpful in easing the transition.

“Even though I knew that my stepping down was the right thing for the organization and for me, even though I could taste the freedom that awaited me, even though I was filled with joy at the prospect of someone I respected and admired so much taking over the role, I was still sad to leave,” Laura wrote.

For Rose, coming to terms with leaving her startup is an ongoing process.

“When you’re running your startup, you dream of someone else having all the responsibility. When you’re working for someone else, you wish you had the power to make the calls.”

“To be honest, I have not completely processed my departure from Chirps,” Rose shared. I don’t think it’s supposed to be a clean process—it’s emotional, and emotions are messy. I do know that the grass may always seem greener. When you’re running your startup, you dream of someone else having all the responsibility. When you’re working for someone else, you wish you had the power to make the calls. Ultimately, I think you just have to know your ‘why’ and ‘how,’ and just stick by that, even when it hurts. I can deal with pain. I have less tolerance for regret.”

Sam was grateful for the support he had in his board, staff, and the Echoing Green community.

“One of the things we do poorly in this space is the notion that we do this work alone. You’re not alone. I had a supportive board, which was a blessing and privilege, and I had access to therapy, an Echoing Green chaplain, and an array of people that allowed me to process and work through my departure.”

Although leaving your startup is difficult, it’s important to step back to reflect on all you have built and the impact you made. Leaning into what you will miss will help inform your interests for your next phase. At the same time, looking forward to new roles that may fulfill needs you weren’t previously getting is important for personal and professional growth. Whether you are questioning whether to leave your startup, ready for your next career step, or just really proactive at forecasting, it’s never too early to consider your departure. In the same spirit that you mapped out a plan for launching your startup, it’s just as critical to map out a plan for leaving—all while taking pride in what you built and comfort in the journey that awaits.

More on the founder succession process from Stanford Social Innovation Review

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