We were lucky to catch up with Brooke Richie-Babbage recently and have shared our conversation below.

Hi Brooke, thanks for joining us today. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

I never saw myself as being a “risk taker” per se. A friend in college described me affectionately as a “road MOST taken” kinda girl – unlike Robert Frost, who chose the road least traveled, I always saw myself as someone who wanted the road ahead to be paved, well-lit, with rest-stops and lots of fellow travelers up ahead ;)

But somehow I wound up being someone who left the comfort of my paying job as a social justice lawyer to start a nonprofit in my mid-20s, despite having a mortgage, no health insurance, and (at least in the first year) no discernible way to make money.

Taking that risk changed everything. It helped me find my life’s purpose, and it introduced me to a world of work and impact that I continue to be deeply passionate about. Most importantly, it started me down the path of entrepreneurship – and I’ve never looked back. It’s led me, most recently, to start my company, Bending Arc (which I now run).

The thing the idea of “risk taking” is that looking back, it didn’t look like how I’d always thought risk-taking looked. I didn’t see myself as a risk taker because I thought that term described people who didn’t have fears, or who runs top speed off of the proverbial cliff and trusts that they’ll land on their feet.

Perhaps that describes some people. But I’ve discovered that I’m a different kind of risk taker – I’ll eventually jump off the cliff, but I’m going to measure the distance to the ground and pack a parachute first!

When I started my organization, I didn’t decide to leave my job and dive fully into building my because I suddenly became this daring person who didn’t have fears. It’s because something happened that made me push through my fears.

And it was a really small, ordinary thing.

When I had originally gotten the idea that I wanted to do work with teenagers in the Bronx to build a youth-led legal clinic as a way of building their sense of self-efficacy and resilience, I told my boss about it and he offered to let me work part-time, keep my health benefits, and work on my project on the side.

So I rented a tiny office for $400 a month and started working on this project. I did that for months and I tried balance both parts of my life. My plan was to continue doing that — stay safe, keep my job that I loved and also do this work that I loved on the side.

Then one day I was sitting at my desk talking to a colleague on the phone, and I crossed my legs and happened to glance down, and I realized that I was wearing two completely different boots. One was brown and the other was black. One zipped up the side and the other was a pull-on. They didn’t look anything alike.

It sounds like a small thing, but it was a moment of clarity for me. I was trying to juggle my secure job as a lawyer with this growing dream of mine, and clearly, something was off. It wasn’t just about the boots, of course. They were just a funny reminder that I couldn’t keep straddling two worlds forever. I had to decide to jump off the cliff or not.

So I decided to jump. Not because the fears went away. The fear about how I was going to pay my mortgage was still there… The fear that this mission that I cared so deeply about wouldn’t resonate with anybody else was still there… The fear that I ultimately wouldn’t succeed — all of those fears were still there.

I was ultimately able to take the huge risk of leaving safety behind and starting my organization, not by ignoring these fears, but by acknowledging them and deciding that some things were just more important to me.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

*There has been a clear throughline in my work. Everything that I do is guided by a central question and core belief. The question is: What is all of millions of nonprofits in this country were all operating at full capacity and in complete flow? What if they* were not constrained by lack of funding, staffing, or strategic clarity. The belief is: If when good nonprofit organizations are strong and stable, they are able to run full-tilt at solving our deepest problems. Our society is stronger, more beautiful and more just when our nonprofits are stronger.

For the past 25 years, my work has been guided by this question and this belief. I named my company Bending Arc because my passion is helping mission-driven leaders build and sustain strong, resilient organizations so that they can do the hard work of bending the moral arc of history towards justice, as MLK Junior said.

All of this is to say: Nonprofits are in my blood – they’re my happy place.

I got bitten by the bug early — as a freshman in college! I interned at the NY office of the ACLU my freshman summer. We were stuffed into a tiny office around the corner from Bryant Park, back before it was pretty and safe. The interns worked in the conference room because there was literally no space, and that meant I got to hear everything! I followed the ED around to meetings, sat in on budget and strategy calls, picked his brain over lunch – I was hooked.

I co-founded my first organization while I was in law and graduate school at Harvard, connecting direct legal support with legislative advocacy to address system-wide injustices in the MA public school system. I learned through trial by fire – raising money, translating opaque legal justice issues into something donors could support, bringing together diverse stakeholders, building and scaling programming — I absolutely LOVED it and I knew from that experience that finding solutions to social problems – and particularly starting and working with nonprofits – was my calling.

I got a Skadden Fellowship to move to NY and work as an impact litigator and policy advocate at the National Center for Law and Economic Justice (at the time, it was called the Welfare Law Center).

By the mid 2000s I’d started working on what would become my second organization – training teens to build social impact initiatives in response to issues they experienced in their schools and communities.

I grew that organization for close to 12 years, from me and an intern in a single rental office and a handful of donations from friends, to an amazing 13-person team, an incredible and engaged board, and raising millions of dollars in revenue. Along the way, I became a graduate professor of social entrepreneurship & nonprofit leadership, and an organizational design strategist and executive coach.

In 2017 I stepped down as ED, and became a strategist and coach full time, partnering with foundations around the country to design and build social impact initiatives.

I launched my podcast, Nonprofit Mastermind Podcast, in 2020, and officially started Bending Arc in 2022. ****Bending Arc is a social impact strategy firm that helps nonprofit leaders launch and scale truly high-impact enterprises.

**Our driving purpose is to make** sure that small, mission-driven organizations are internally strong so that they can do the important work of changing our world. We offer educational content to nonprofit founders who want to launch successful organizations, hands-on coaching and wrap-around support to Executive Directors of nonprofits between $250K – $3M who want to scale their impact, and done-with-you strategic visioning and program design for Foundations that want to support organizational resilience at scale.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One particularly gnarly lesson that I’ve had to unlearn is that there is honor in the “hustle.” Put another way, my greatest pride financially should come from showing that I can “do as much as possible with whatever little I have.”

I think that that story has been both personal and professional for me. Personally, I grew up watching my parents build a life together that surpassed either of their wildest dreams, personally and professionally. Both of my parents grew up extremely poor, navigating experiences of poverty that were almost stereotypical of Black children and families in the middle part of the 20th century. Together, they built a beautiful marriage and a happy family that was unlike any model they’d seen, as well as financial success and wealth that

And what I saw in how they moved through the world, and heard in their stories, was that they were so successful because they worked their assess off every single day, prioritized effort over rest, and took pride in stretching every dollar as far as possible, even when doing so had become financially unnecessary.

I took this orientation towards hard work and financial prudence into my profession, where it was hardened and crystalized into a form of martyrdom that most of us in the nonprofit sector would recognize. Valuing hard work turned into honoring the hustle mentality – the idea that we demonstrate our worth by working 90-hour weeks and never taking vacation. Financial prudence became the justification for accepting (and paying) salaries that didn’t even equal living wage and investing in program growth rather than health insurance for staff.

I want to be clear: I deeply value hard work, and I don’t think we build anything impactful without a great deal of hard work. But hard work devoid of joy and unbalanced by rest is both unsustainable and unhealthy and shouldn’t be the goal. Similarly, I believe that financial prudence is critically important. But prudence can easily morph into playing small: Not shooting for the stars becomes somehow it’s become acceptable to limit ourselves to playing in the grass.

The new story I tell myself has an expanded definition of what success looks like for me: Instead of the hustle, my hard work goes hand in hand with spaciousness and intentional pauses; and rather than playing small, I set bold financial goals and choose to believe that I have what it takes to achieve them.

Have you ever had to pivot?

I’m what people call “multi-passionate.” I’ve always loved having multiple balls in the air at one time.

That’s one of the things that I loved about being an Executive Director – the job allowed me to explore and learn about different things, and no two days were the same!

So when I stepped down as ED of my org in 2017 I approached my new found freedom the same way. I immediately signed on to multiple projects that seemed interesting and looked forward to having more space and time to explore all of my various passions.

Yet a year later I looked up and rather than a well-balanced constellation of engagements, I found myself leading and co-leading multiple full-blown enterprises. From launching my consulting company (the predecessor to Bending Arc), to co-founding a media company to create content that makes it easier for every day people to understand the law, to directing a citywide network of sector leaders working together around economic justice — I was pulled in too many directions, frazzled, and exhausted.

And then my husband and I had our second child, and I neared my breaking point. Something had to give.

My pivot was winding down my engagement with most of the projects that I was working on and leaning into a single one. This seems like a small thing, but I really needed to shift my internal narrative so that letting go of the various projects didn’t feel like I was limiting or constraining myself.

I also realized that I needed to learn to tell the difference between signing on to something because it was a true passion that I was being called to explore versus signing on because of FOMO or out of a desire to hedge my bets in case one of my projects didn’t work out.

Ultimately, I continue to learn how to balance my multiple passions and need for variety with an equal need for focus.

Contact Info:

• Website: www.brookerichiebabbage.com
• Instagram: @bjrichiebabbage
• Linkedin: https://www.linkedin.com/in/bjrichiebabbage/