Leading Against the Odds

In my experiences over the last dozen years working to transform the abortion conflict, I’ve encountered some hard truths about why we humans have so much trouble getting ourselves out of the sticky problems we create for ourselves. My organization Exhale has sought to influence mainstream culture, unearth hidden stories, and demonstrate that it’s possible to nurture human connection and empathy despite increasing hostility and polarization—but it’s been no easy task. Like most leaders, I’ve needed to adapt so that I can face each new challenge with openness and optimism.

Early on in the job, I asked a prominent feminist leader how she kept going against so many odds, and her answer—that sacrificing for the cause was worth it—didn’t help me at all. Over the last decade, I’ve witnessed how sacrifices like hers can eventually lead to personal resentment, bitterness, and despair. Feelings of hopelessness are a real threat to our ability as leaders to imagine creative new possibilities. Many just give up.

Take Paul Kingsworth, an environmental activist, who is so disheartened by a lack of action on climate change that he’s moved his family to a rural area to begin preparing for the worst. “Whenever I hear the word ‘hope’ these days, I reach for my whiskey bottle,” he has said. “Surely we only hope when we are powerless?”

Not true, says Raven Brooks, executive director of a progressive activist network that influences politics and public policy called Netroots Nation. Brooks has seen bitterness about the state of the world manifest as cynicism and believes it’s something activists “must guard against.” “It’s one thing to be pragmatic,” he acknowledges, but it’s another to “get to the point that you are so cynical that you can’t throw a Hail Mary or think about what’s needed to change the game. You will talk yourself out of everything.”

So, how do leaders do it? How do they wake up everyday, step outside, and face a world full of injustice, hardship, and difficult decisions with no easy answers?

I recently interviewed a number of social entrepreneurs, including Brooks, to find out what it really takes—beyond time and money—to make lasting change. Their answers were inspiring but definitely not simple. People who take leadership seriously develop a host of strategies to wade through the rough waters of social change while also taking care of themselves. Their answers are about discipline and focus.

Here are some of my top takeaways from these conversations:

• Strong leaders know how to make change. Every single leader I interviewed knows how to make change happen (even one person who said she didn’t went on to describe how she does it—regularly and successfully). Change is a lived experience for them. They might not have known how at first. It took time to get there. They had to overcome obstacles, navigate failures, and make mistakes, but they persevered, adapted, and came out the other side with knowledge and insight. That means that whatever the political or social challenge of the day, leaders have confidence in their own abilities to figure it out. They are ready for more.
• They use dilemmas to innovate. Whether the cause is prison abolition, contraceptive safety, or climate change, leaders seek to avoid black-and-white thinking and use gray areas to imagine new possibilities. Over and over, the people I interviewed acknowledged the difficult social, political, and cultural terrain in which they operated, and expressed how valuable it was to communicate these challenges clearly, directly, and publicly. Highly ethical, they were most concerned with being truthful, credible, and real—not convincing, persuasive, or right.
• They don’t sacrifice themselves for the cause. As I mentioned above: Burnout, cynicism, bitterness, and despair get in the way of change, and while the leaders I interviewed said they had moments when they felt all of these things, they have developed methods to not stay stuck there. Each strongly resisted the idea that sacrifice was fundamental to leadership or social change, and noted that creative, joyful, generous people are best suited to social change work. It was also interesting to note that for some changemakers, rejecting upwardly mobile, middle-class aspirations isn’t a sacrifice (despite how others perceive their choices), but a lived reflection of deeply held ethics and values that give their life meaning.
• They know political risks have more to do with friends than enemies. Here’s the challenge with acknowledging gray areas publicly: The primary risk that leaders I interviewed faced when it came to speaking openly about challenges inherent in issues like abortion or prison abolition is that it can piss off your friends. Friends (the people and organizations that share goals, and the foundations that fund them) sometimes perceive talking about dilemmas as a sign of weakness, believing it signals a lack of conviction or provides enemies with something to exploit. Peer pressure, conflict, and the desire to hold onto relationships for future funding or coalition-building are obstacles leaders face when they use dilemmas to think creatively and spur innovation.

The message I took away was clear. Leaders make mistakes, but they don’t let that stop them. Innovative leaders regroup. They adapt. They go back at it again. They find new ways forward, and they take important risks that can jeopardize future funding or collaboration with allies if it means doing what’s best. That’s how they make change, and how they’re ready to do it time and time again.

Read more stories by Aspen Baker.