Pivot Like a Pro with Casey Johnson

Join hosts Erin Cox and Scott Knox in a thought-provoking conversation with Casey Johnson, a leader in the nonprofit world and current national leader at the GreenLight Fund. Casey reflects on her career journey, the personal and professional transitions she's made, and her experience building high-impact programs across multiple communities. The discussion covers the challenges of scaling nonprofit initiatives, the power of strategic investments in social ventures, and the critical role of empathy and relationship-building in leadership. Get inspired by Casey’s insights on how to manage growth, sustainability, and mission-driven impact in the ever-evolving nonprofit landscape.

Hosted by Erin Cox and M. Scott Knox
Edited and Produced by Stephanie Cohen

Transcript

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Welcome to the Lead and Live Well podcast. My name is Erin Cox, and I'm thrilled to be here with my co host Scott Knox. On the Lead and Live Well podcast. We sit down with leaders in the social impact world to learn about their leadership journeys. 

We talk about their strengths and passions, the transitions they have made in their career, And how they have crafted their own paths to leadership.

Our goal is to highlight a diverse array of leaders and journeys, so that our listeners learn from relatable and compelling examples of what it means to lead and live well. 

Erin: I know I can promise a great conversation today because we are joined by Casey Johnson . So Casey has worked in the nonprofit sector for over 20 years. In the first half of her career, she worked in direct service organizations, impacting young people and focused on literacy and family engagement both in the United States and outside of the US. 

Almost 13 years ago, Casey was invited by her longtime mentors and former funder to launch a pilot of the Green Light Fund in the San Francisco Bay area, as the venture philanthropy firm made its first jump outside of its flagship in Boston. Casey led Green Light's Bay Area work for her first six years there and oversaw its first four investments, before shifting into a national leadership role for the organization as it continued to grow its footprint and impact around the country. On a personal level, Casey is based in Omaha, Nebraska. First interview from Omaha. Very exciting. 

She's a mama of two boys. Bonus mama to her beautiful stepdaughter and a dog mama to two rescues. She currently serves as board president for Christy Yamaguchi's Always Dream nonprofit, and recently joined the U. S. Board of Language and Learning Foundation. And I'll just personally say she's one of the most intelligent, grounded, friendly, and talented people I've ever had the pleasure of knowing and working with. So you're all in for a real treat today. Welcome, Casey.

Casey: Thank you, Erin. So, so excited. I can say all of the things right back at you, my friends. Excited for today's conversation.

Erin: So we really appreciate you spending this time with us. And I think we were ready to jump right in. So Scott, kick us off.

Scott: Yeah, Casey, it's so great to have you. I'm a super fan of the Green Light Fund. And there's so much to talk about but for our listeners, can you share a little bit more about what the Green Light Fund is?

Casey: Absolutely. So the Green Light Fund, we are a nonprofit ourselves, but we are what some people call an intermediary, venture philanthropy firm import funder. We've been given different names, different labels, but we raise and then invest funds in helping organizations scale and replicate their work into our communities around the country. But only when in partnership with the local community where we operate that it matches an unmet critical need that it's going to move the needle on. We've been around for 20 years. And as Erin said, our flagship headquarters started in Boston. I have the great fortune of launching one of the first pilots outside of Boston. We're now in 13 different communities around the country and adding a new community every year to our network.

So, it's been a pretty phenomenal kind of span.. We've made investments. We say investments, it's grants, but it's our language that we use. Um, We've made grants investments into so many different organizations through the years, I think a total of 54 to date spanning across that network of communities, as well as spanning different focus areas. So we're really looking at moving the needle on economic mobility for community members, residents, families, and that has lended us to make investments in workforce development in all aspects of education. I say prenatal all the way through to post secondary and career readiness.

We've done well. We've done housing. Just a little bit of, a little bit of everything. So that's hopefully a good snapshot of Greenlight for you guys.

Scott: That was great. Thank you.

Erin: I'm speaking from personal experience because you toggle between grants and investments. I think investments is totally appropriate language to use for Green Light because you vet folks, like the vetting process itself contributes to an organization's maturity. Again, speaking from firsthand experience. The pitching process, I think, grows up organizations that are at that cusp and ready for that next level.

And when you invest you're participating on boards, you're connecting, you have an advisory board locally that is already well positioned to welcome and catapult that organization forward. That's much more than a grant. So like, I'm not even sure investments do it justice, but we'll stick with that for now.

Casey: Thank you for lifting that up, Erin. Because that's our hope and ideal that our portfolio organizations feel what we often refer to as beyond the check supports, and we've heard so much from them that they love the check. It's like, to be clear. We love the check six figures unrestricted, never a bad thing.

But it's the high value of all of beyond the check supports because for you both, I know experiences, but for probably so many of your listeners who are working in the nonprofit social sector and may have been a part of organizations that are trying to figure out scale growth replication, it's not easy.

And especially when you're trying to bring your amazing work and impact into a community where you may not have deep relationships yet. You may not know the local context and the lay of the land yet. And Greenlight tries to be that critical navigator, partner, connector advisor, cheerleader, shoulder to cry on.

I've definitely been that for many. As you're trying to bring your work to places beyond your, I say, mothership or your headquarters where you really have probably the strongest ties and deepest roots. So it's really trying to create that pulling mechanism instead of pushing mechanism and that pulling environment.

So the community feels like we need this. We want this. Let's bring this in. Let's embrace this. Instead of an organization being perceived by community that they're pushing their way. Organizations tend not to last long in those communities. And for us, we've, like I said, we've done 54 investments to date.

53 out of the 54 are still thriving and growing in the communities we brought them into. And now some of those are still very active for us, but over 30 are what we call legacy, which is our funding has ended. Its typically four to five years of funding has ended. But our hope is that we're not just bringing something in that is going to work while we fund it, and then it goes away. Because none of the problems that we are trying to move on are going to be solved in 2, 3, 4 years. These are deeply entrenched systems and systems that are set up to fail the people that we are trying to impact. So it takes much more work. It takes a much longer kind of timeline.

And our belief is if we could deeply root them. In order to have them demonstrate impact as quickly as possible with great fidelity their model, they're going to build in that buy-in and support to continue to thrive and grow over the long haul. And so far so good. That one kills me. I wish we were 54 for 54

But 53 for 54. I'll take

Erin: That's a pretty excellent proof of concept. And I think it's like Scott, as Casey was talking, I couldn't help, but reflect on it. Scott and I were both directors of new site development at Jumpstart at different times. I followed in his incredible footsteps and benefited from all of the things that he figured out there.

That model was like rinse and repeat, hub and spoke. When I did it, we were 15 to 20 sites a year created new. And I understand that struggle of kind of like building that community investment and connecting all the pieces. We, because our model is relatively simple and replicable, we were able to do it.

Fast forward to my experience at uAspire, like that was a very different model and it really needed that foundational support to enter into a new community. And also college affordability wasn't really understood at the time. So we needed a super intelligent group of people who really carefully vetted the organization to help us make the case for why a hyper focus on the affordability piece was the way to address the higher ed issues that the Bay area was facing.

So, yeah, we're three non profit growth dorks and we can talk

about just that. Here we go. I know. Casey and I in our prep call, we were like, literally, it could be a day episode. Nobody wants that except for us. So I'm going to tone it down 

Scott: Tempting. It's tempting. 

Erin: Yeah, exactly.

That'll be episode two. Only if the audience asks for it. Just kidding. So we want to hone in on you, Casey, because your bio kind of gave some great highlights about your transitions. And you've obviously been at Greenlight for a long time, but I know there's transitions built into that.

Personal and professional, right? So 13 years in one place, but it's not been the same thing for that period of time, especially given that impressive growth you talked about. So we, what we like to invite our guests to do is we kind of launch into the conversation is just talk us through your career trajectory, to this point.

And in particular, we'd like to ask you to hone in on the choices that you've made along the way. And sometimes we recognize that those choices are due to, like, intentional decisions or intentional choices versus chance. And I know there's a little bit of both in your background. 

Casey: Yeah, I was gonna say for my story, I would say it was maybe a 50-50 or maybe 60-40 chance. But it all aligned and got me to this point. So I'm going to take us back to college, which feels so long ago now, but probably where that first pivotal intentional decision did come, that kind of, I think then was the domino effect of the early, probably my early years in my career.

So I was, and I actually don't know, Erin, if you know this, but for Scott, well, I was a track athlete. So I competed. For 10 years and in, in college, I was a jumper and a hurdler and had a pretty successful track career and ended up earning a coveted NCAA postgraduate scholarship which was awesome.

And. And much needed if I were going to be pursuing anything post undergrad because my family was not in a position to pay for college, let alone graduate school. And I was the first in my family to go to college and unfortunately the only one to go.

And so just a side note. uAspire will always stay close to my heart because there's a deep personal connection around mission and work that I surely, and as well as many of my friends growing up in rural South would have benefited from many moons ago. But back to this kind of pivotal moment.

So I was approaching graduation. I got this postgraduate scholarship. I had three options on the table Peace Corps, graduate school, or trained professionally to compete in track and field as a professional and ultimately would have been a heptathlete competing, which since the Olympics are just two weeks away, I feel like can definitely like, woohoo for heptathlon, on heptathletes.

And. it was a tough decision because out of all of those options, nobody in my family had ever had one, let alone any of those opportunities had ever explored it. Most of them would have taken me out of where I grew up in Virginia and away from my family unit friend, you like my kind of base to strike out on my own.

I ultimately chose to pursue graduate school and utilize that scholarship because I thought and was worried if I didn't, I might not ever. What would be the chance? Other things would have gotten in the way. And I felt like I had this scholarship sitting there and maybe that was like a sign to, to use it.

So I ended up choosing graduate school and I had fallen in love with the idea of going to New York city. And so I was the only place I applied to graduate school and ended up going to Brooklyn College. I was an English major and thought I was on the trajectory to study American literature, Southern literature, and ultimately go into a PhD program, teach, and then coach at a women's college somewhere.

I thought that was like the path. And so I left rural Virginia. Went to New York City, went to Brooklyn and having not really known anyone, to be honest with you and questioned all along the way if this was the right idea, by the way learned very quickly to not make eye contact on subways, to not say good morning and ma'am and sir at any point.

And definitely not to use y'all at any point during my foray there. But I was doing uh, grad school full time. I was working full time because the scholarship was great, but it covered all of the tuition, but did not cover room and board. And so I had to work full time and I was working in an, a paid internship in athletic communications at Columbia University and had a very full load, but I felt like something was missing. 

 All through high school, all through college, I was still very much wanting to impact my community and had sought out volunteer opportunities and local organizations to be able to feel like I was weaving in the fabric of community by being able to impact and give back. And that was missing in New York. And I saw a flier for this literacy program that was taking place at one of the public schools in Harlem, right near Columbia's campus that I could walk to and started volunteering in that literacy program.

And it was that like that proverbial light bulb went off of, oh, my love of reading, my love of books, all things related to reading and literacy and this call to want to be able to give back and have equitable opportunities that I never saw in the South given. I could, that I could do that.

That makes way more sense than your PhD program and teaching at a college and coaching track. Although I love track, I thought that just makes so much more sense. And that was about halfway through that master's program that lightbulb went off and I definitely didn't think it would be a good idea to just stop grad school and make a pivot. So I thought, Ooh, I should probably finish this. Like, let me finish this through. But I'm not going into a PhD program. It's, it does, that doesn't make sense. 

And from that point on, when that kind of moment was made. And when I graduated from that master's program, that's when I started working, always volunteering, but also starting to work in the nonprofit sector and worked in the nonprofit sector ever since I will call out that there was another decision made.

But also chance, if we equate love to chance. 

But I also ended up falling in love unexpectedly like towards the tail end of being in New York and a grad program. I applied to Teach for America. It was very early on when Wendy had established. It was early days but I thought, Oh this can help be that foray in that literacy piece and the work that I was doing in that literacy program, as well as starting to make a career for my first kind of career decision move.

I got in and I got assigned to the Mississippi Delta.

And so that was on the table, but then the person that I fell in love with got a job in Casper, Wyoming to be a head basketball coach And this was, pre FaceTime and texting, right? this was the Nokia phones, right? This was not that.

So it was thinking, Oh, I don't know. How is the long distance going to work? And I'll be in Mississippi. He'll be in Wyoming. I don't know if this is going to work. And he asked me to join him in Wyoming, and it was one of those, I was raised as a feminist. So it was one of those, like, I'm not going to follow a man to Wyoming.

 My aunts will kill me! That's not how they, how they raised me, but there was something there about love that I thought, I just want to see where this is going to go. So I said, no to the opportunity and said, yes, Casper, Wyoming, which I will be honest. I had no idea where Casper was in Wyoming, and I kind of knew that Wyoming was one of those box states out west um, and and we got there, and I started working for the Girl Scout Council of Wyoming, so it was my first official nonprofit job leading their programming statewide, and and really leaning into kind of mentorship work for young people.

Casey: And. That was my first nonprofit job. And so I can definitely speak to, you know, other pieces along the way, but I wanted to share that because there's, for me, there's those, Moments of where you are at a crossroads, you have to make a decision and I felt like at the time, those are decisions I had to make, not for me, not something that somebody else made for me, or there were key ones, and so much of it was following instinct, where I felt pulled, like that calling and feeling pulled and what felt right, even though all the signs were like no, what are you doing?

No way. Like, this is super risky. This could go sideways. In so many ways, and where I questioned myself, for those two big decisions early on, right? Like, should I have gone to New York? Should I have done this? Should I have followed this guy to Wyoming when I know nothing and no one there.

And and yet I'm really proud of myself for being, you know, young and naive in so many ways, but also listening to my inner voice and following my values and and staying true to who I was that I think has been probably with me at every other decision point in my career path that has come along the way.

So I'll stop there because I could go on for many moons because I made a bunch of different pivots and turns along the way until I got to Green Light. But I always think there's something powerful about the start. 

Erin: Yeah. Yeah. I'm so glad you went through that. And I, as a New Yorker, I'm surprised and slightly disappointed that we just knocked the southern hospitality right at you shortly after your arrival.

Casey: Accent.

I know a lot. Yeah. The accent has been gone since New York.

Erin: You still have a little bit of an accent. I'm just going to tell you that. Maybe it's been informed by the many other places you've lived and we'll get into that in a moment. But I also think, thank you for sharing all the vulnerability that went into those early decisions and like you were young. You were building your life experience. You didn't have a huge track record to go off of.

So I think those are really helpful examples. One of the things I always tell my coaching clients who are at a crossroads is like, this is a decision. I know it feels like the decision right now. It's a decision. And more often than not, if we don't make the right one, we can make another one and we can make another one and we can make another one.

And so, but it sounds like you really followed those instincts, listened to your heart and landed in the right place throughout. That's beautiful. And I was struck by this idea that you thought you were going to go into teaching and coaching. Which I feel like when we talk about what you do at Greenlight right now, I'm going to come back around and be like, you are a teacher and a coach, just in a different context.

So I do feel like you came back around on that one. Yeah.

Casey: So true. I know that I ended up picking up a second master's when we were in San Francisco at the University of San Francisco teaching because I, a student , taught and thought I was going to be in a classroom. Um, At some point, this was like fast forward, probably eight years or so.

And. And it's the running joke within my family and friends of all these years, I kept thinking in some way, shape or form, I would be in a classroom teaching and I haven't technically made it into a classroom like the in the traditional sense in elementary school or a high school or a college, but everything that I do, especially, I would say the last, 13 years of Green Light, but really the last six in the role that I'm in now overseeing our national portfolio and learning function has absolutely been that. So thank you for recognizing that because it's something that we always get a good laugh at if I've done all this and thought that I would be there.

I thought that I would be there. I thought that I would be there. TFA, thought that I would be there and then never actually went in. And yet this is probably what I live and breathe and do and love every single day

Erin: Well, not yet. Who knows? But not all classrooms have four walls, right? I think you, you make classrooms in your community work. So I do want to hone in on the choice that you made to go to Greenlight. So I think we're fast forwarding a little bit. But in your bio you introduced it by saying you were invited by a long time mentor and former funder.

So that to me speaks to the power of a network in providing choices. So can you just tell us a little bit about that transition and what drove it for you?

Casey: Yes. So to my great fortune when my husband, so spoiler alert, the person that I followed to Wyoming, I married and I have a beautiful family with and we've been together for quite a long time. He made a career transition himself and was offered a fellowship at Harvard, which brought us from San Francisco, where we were living at that time to Boston. And at that time I was running an early literacy program in the Bay area. called Raising Reader that I absolutely loved. And hopefully many who are listening will know or now know of it's phenomenal. And right around the time when we were moving to Boston and I think you could see like, like my fingernail marks, leaving San Francisco all the way across the country where I love San Francisco and the Bay, I love Raising Reader.

I was like, what in the world are we going to do in Boston while he's doing this fellowship. And to my great fortune, Greenlight Fund had just selected their second investment to bring into Boston, and it was Raising A Reader. And I never heard of Greenlight, of course, because at that time, it was just known as a Boston thing.

And they had selected the executive director, Donna DeFilippo, to lead Raising a Reader for Massachusetts there, set up its own 501c3, and Donna was at the place where she was like, I can't do this alone, I need a number two, and our mutual friends at Raising a Reader and our broad network said, oh, Casey, moving there.

I was thinking I would volunteer with Raising A Reader because I wanted to still stay in touch. And Donna was like, Oh no, I need you to come work with me. And I think I did a little dance. I have to say. It was one of those where it felt like chance, all stars aligned. And it was probably one of the greatest periods of my life.

One because Donna's a phenomenal leader but also because I got a front row seat in Green Light's model. And that's what began the mentorship of Green Light's two co-founders, John Simon and Margaret Hall. And I got to see what it was like to be a grantee, to be on the receiving end of. The phenomenal check and the beyond the check supports and.

And thought, well, this is the greatest funder I've ever had. Why can't all funders be like this? And so fast forward from there, we Bill finished his fellowship. We moved to D. C. and then ended up getting wooed back and moved back to San Francisco because we loved it that much. We had to live there twice, move back to San Francisco and was doing a fellowship with Room to Read at the time, which I loved. They do literacy and girls education work in developing countries outside of the U. S. And I was about halfway through that fellowship. I was pregnant with my second son, and John and Margaret called and said, we'd love to catch up.

We're going to be in San Francisco in a couple of weeks. Can we go out to dinner? And I always kept in touch with them because they were phenomenal mentors. So they knew I was back in San Francisco and wanted to catch up over dinner. But I had no idea why. Because John, you know, he's a venture capitalist.

I knew he was still doing a lot of deals at that time. He was With General Catalyst then and was doing a lot of deals in Silicon Valley and in the Bay and West Coast. I was like, why Margaret with them? This is weird. And so we, a couple of weeks forward, we had dinner and. Towards the end of the dinner set, they said, we think we're ready to take the Green Light Fund outside of Boston.

Would you consider launching a pilot for us in the San Francisco Bay Area? And I think I fell off my chair in that restaurant because I was like, wait a minute. You're, this isn't just a Boston thing. I, we, you actually really wanted to take this I, I just couched them as this Boston thing. And I was thrilled because I remembered from a couple years prior of how phenomenal it was to have their support for Raising a Reader that positioned us to go statewide in Massachusetts, not just in kind of Boston Metro, and that they were critical board members, advisors, cheerleaders, connectors, all those things and thought, wait, that's, then it's like, of course, they, I don't, I've never known another funder that's done that.

And how amazing would that be if. Other communities, including the Bay Area, would have it. And I immediately said, I know you probably should, like be like, Oh, let me think about it. And I was like, of course, I committed to Room to Read. I got to finish this fellowship.

Yeah. That I was one of their first fellows. And so I was like, please let me finish this fellowship. And then, you know, and then I'll lay the groundwork for this. And they were like, of course. We'll work around that. And then I was like, and you can't tell, but I'm also pregnant with my second son.

Uh, So I'll need some bonding time. And they're like, we'll work around it. And the rest is history. I finished the fellowship and laid the groundwork for Greenlight in the Bay area, gave birth to Adam, bonded with him, and then officially launched Greenlight in the Bay. And In March 2012. And I always, it's easy for me to remember how long I've been at Greenlight because I just think of how old Adam is.

Since he's been, as I've grown the baby there he's now soon to be a teenager. He'll be 13 in a couple months.

Erin: Wow. That's awesome. And it's helpful to have that physical manifestation for sure. Both on, on solid growth trajectories. Yeah. Super helpful to hear you talk through that. And I'm hearing at various points in your career trajectory, you dance, fall off your chair, hurdle and jump all the things.

Scott: Thanks.

Casey: Women are medicine. I've learned.

Erin: All right. Well, let's pause. I know we're going to get more into your experience and your growth at Greenlight. In particular, when we talk about like work and life transitions and growth, let's jump into strengths. And I know Scott has a number of questions on that front.

Scott: I wrote down the chance dance. This may be, you may have come up with something.

Erin: Love it. 

Scott: So. As Erin queued up, transitioned to talk a little bit about your strengths and can you share with our listeners, what would you say you're exceptionally good at?

As you share that, if you can also reflect on how you got good at that?

Casey: Oh, these are great. And it's hard. Oh, it's so hard to like, talk about yourself in

Erin: Don't worry. I'll fill the gaps. Go ahead.

Casey: I would say, I think what I know to be true, but also what I've been told. So it feels like that affirmation too, is probably one of my greatest strengths is building, nurturing, maintaining relationships.

I am highly relational. And I think within that, I'm a lifelong learner and I don't say that lightly and probably constantly going back to school is a signal of that for sure. But to me at the core, I'm so curious about the world and especially about people and who they are. And what their story is and how they got to probably a lot of conversations you're having on the pod, how they got to where they are.

And that I will forever be whether I'm meeting somebody for the first time uh, you know, I'm that person on the airplane that you probably don't want to be sitting next to because I typically start talking to people and really curious and have conversation the whole flight. But it truly comes from a place of, I, I feel like there's something I can always learn from others on.

And there's a I think also I try to impart deep empathy that I've never walked in anybody else's shoes. I've walked in mine and I've had life experiences that have informed who I am and decisions that I make and how I go about in this world and I want to understand others and where there's points of connection, it's great to call that out and where there's.

Points of variance, or parting. I like to understand that, too. And what that means and what's up. So, I'd say that's probably one of the biggies is that deep value relationships, being highly relational. Part of that is empathy. Part of that's curiosity. Part of that's trust which I think they're all probably connected. 

So I think that's what I would lift up. There could be others, but to me, that's so central to who I am and how I operate within Green Light, outside of Green Light and my life. How I am with my kids, my family my volunteer work that I feel like it's probably a common thread throughout and that most people would say, I maybe they'd say Casey's a talker, they probably would say that, but but also just that she built strong ties and strong relationships, and I think it served me well at Green Light in particular, because I feel like our work in the social sector is so highly relational.

We talk about systems. We talk about things operating in different silos and now there's a lot of talk about AI. I feel like something, some articles, some blogs, something with the social sector at AI is hitting my inbox five times a day. But I think at the end of the day, it's human beings that are advancing this work.

It's human beings that are negotiating different systems and different silos and breaking down barriers and walls. And I'll lean in to building and strengthening relationships with those human beings every day of the week and twice on Sunday

Scott: Just in this short amount of time of getting to know you, Casey, I wondered if you were going to lift this up as your, your superpower. And that's my word, because I know it's hard to talk about those things that we name or others help us name that we're good at.

And I, you know, two, two thoughts. One is, I'm thinking about how this is purely observational that so many folks who I know who are the first, you know, and how, whatever that first is, whether it's like first to get across the high school graduation finish line, first to get a BA, that there's often a characteristic is that they're really good at maintaining and building community and networks.

And there's so much, there's so much of the forward looking that comes with being a first, and the importance of those new relationships.

Casey: That deeply resonates for me, Scott, I would say. Very much so. And I also think there's probably a lot of analogies for. Former athletes too. There's so much about probably any activity you would do, but since I leaned in on my activities were sports and particularly into track that it served me that has served me in dividends through the years from time management, leadership,

hard work, investing in yourself. Like, there's just so much of that. But if I think about it for 10 years, I was on a team that was. Supporting me, supporting each other, pushing each other, challenging each other. And I always had, I know Erin will love this. I always had a coach or more than one coach. Who had my best interest at heart and the teams, but who was invested in what I can do to help you be your best, to shine your best.

And in the case of track, which is beautiful, anybody can do track because there's so many different events. that you can choose and plug into and help you find which ones are the right ones for you that fit your interests, your skills, And then you can next level up, but none of it done in isolation.

And so I often wonder if that team dynamic, that coaching dynamic that I grew up in, shaped the early part of who I was at that time. Cause I started when I was, I think it's 1213. Right. And so think about that period of that you're developing and growing and starting to have a perspective on the world and an ID and your identity and who you are, that I've tried to find and cultivate that in every aspect of my life sense, but doesn't necessarily mean being on a track anymore running laps, which my knees can't handle. Um, I think you're onto something there and I would be curious for or any athletes, former athletes listening, I wonder if this resonates for you as it does for me

Erin: I was not an athlete at that level. But yes, and yes, I should say I, so one thing I just want to add to your list of strengths and there's many more than one, but I think you have a really interesting way of balancing that deep relationship, empathy, trust building with systems oriented thinking.

I think I, you're a builder. You built Greenlight in the Bay Area, and I know there were examples of that before in your career, at that point in your career, and you've been building Greenlight, its national impact in that teaching, coaching role internally and externally for the last 13 years. And I think that's a pretty rare combination of being able to really value and build both relationships and like systems and operations.

I just appreciate that about you.

Casey: on that. I don't know if I would have called that out, but I love that. And it's probably 1 of the things that has always drawn me and excited me. Like, I still, I joke, I still skip to work every day, but it's, but I. I work from home when I'm not on a plane. So it's like skipping from the kitchen to the office.

But I still do. And I think that always surprises people because I think in this day and age, maybe not just for the social sector and nonprofit sector, folks don't stay for huge chunks of time anymore. It's more of an anomaly and they're always surprised when they hear how long I've been at Green Light.

And. But for me, it's. If I was in the same job, and it was a little bit of brown dog day, I probably wouldn't be but the fact that by nature of what we do at Greenlight, truly every day is, I feel like is there's a new learning opportunity, a new challenge, just something new, and the fact that we've been In growth mode and building an organization that now has a pretty significant national footprint and will continue to grow that footprint.

It's kept me on my toes in the best way possible to be in a position to think about how we build this organization. How do we build this team? How do we always best support our portfolio organizations? Cause that's The whole point of this to get impact and community. But how do we do it in a way that is scalable and sustainable?

I will say we haven't fully figured it out. I haven't fully figured it out. There's still things I'm trying to figure out. Um, But the challenge of it has been very exciting and gets me jazzed. I will not kid you every single day that I've been a Green Light. Yeah.

Erin: Well when you do figure it out you should transition to book writing mode because a lot of people will want to know what you've figured out. And I would say Greenlight has redefined growth mode. Like lots of organizations grow and then maintain and sustain. You're just, you're constant growth.

It's really impressive. I want to jump into the blending of work and life. Because you've given me some interesting stats when we prepped for this chat. I would love to frame this part of the conversation as like your lessons learned and or your tips for our listeners because I think you have a robustness of experience Casey that not many people necessarily have and you've managed it incredibly well. So you said, and then you'll have to tell me if I get these things wrong, but like seven, I think in your time, just a Green Light. Or maybe in your career. You'll do. You'll correct me

Casey: In my life, it would be. 

Erin: Seven states, three kids, two dogs, four.

You've lived in four cities with Green Light and plus one is a grantee. And there was a period of time where I feel like you were moving everyone to two years. It's for like good and significant reasons and all of those things came along with you including your very big and growing job. So help us understand like how did you, how do you manage all that?

What are your tips and tricks for the blending of work and life from your vantage point?

Casey: Yeah. That's I know when you lay it out like that I'm tired already. And what I will say is, I didn't manage it. Well, there were moments where I felt like I was going to have a total breakdown. And there were moments where I may not have shown up as the best partner or the best mom because of being tired and exhausted. And there was a moment where I was notorious for doing red eyes at Greenlight, because we've lived, San Francisco and the Bay, and I was flying a ton and flying to a lot of our East coast sites. Like, I was trying to maximize time with my family, fly at night, show up, for the meeting that was 8 AM and I arrive at 5 or 6 AM in the airport bathroom.

And, everybody knows I love Starbucks hot chocolate. Get that to help me get going. And then always folks saying, How are you this happy and awake this early in the morning coming off a red eye? I'm like, I don't know. This is just who I am. I'm so sorry. But it's but realizing that I can't sustain that. 

Pre pandemic, I think I made a decision. I'm never having a red eye again. And I haven't. I just can't. I've also truly done my best. I can try to prioritize my family and my kids. First, it's really important to me that they see me as a working parent. They see that this work brings me joy and it's an investment in myself, but it's also a financial investment in my future.

I'm building my retirement account. I'm contributing to my family. That has always been extremely important to me to feel like I had that independence and partnership with my partner, their dad, my, my husband. And that also meant that I couldn't always be at everything and I might miss a birthday here or there which I have and I try not to feel too much guilt over it.

And I look at the long game and the long road of, I've got 18 plus years of helping to shape and nurture three human beings and then some, post as they leave the nest as one of ours has but, missing this one thing is not going to in the grand scheme of things is not going to affect that overall shaping and influence.

What has helped is that I have had a phenomenal partner who is a phenomenal dad and has leaned in even though his career path has skyrocketed in a pretty significant way. He shows up and shows out for his kids always first and foremost. And so between the two of us. I feel like we got it covered.

It's like the, we, like the man to man coverage, he's a basketball guy. So like man to man, we have it. And I trust him when I'm not there, I have deep faith and trust. And when he's doing his thing, then I'm there. And then when we're together, it's like, hopefully gold. But I think having him has been phenomenal.

Also being at Green Light, especially, I would say is so supportive of somebody coming and being their whole self and that and an honoring and a value of if they are, that's going to be phenomenal for Green Light and phenomenal for impact for organizations in our work. And so that means I've got great flexibility and if I truly can't miss something.

Somebody else steps in and I do the same for them. 

Also, uh, two years ago, our board approved the first ever sabbatical program at Green Light and. I was able to take advantage of that last summer, tied into this last hopefully move for a while when we came to Omaha last June, I started my sabbatical in July and it's a six week paid sabbatical program when you hit six years and anybody in the organization Gets to take advantage of that, which I absolutely love.

No matter where you sit within the organization, it's honoring that commitment in time of six years. At that time, I was 12 years old. And so Greenlight graciously doubled the sabbatical time for me. So I ended up having 12 weeks and truly unplugged from Greenlight during that time. But the fact that I was able to do that, it was paid time off for me to do that.

But the phenomenal team and leadership of Greenlight being able to Sub in for me while I was gone so that I had full faith in my team and my colleagues at Green Light that I could step away and didn't feel like I had to peek in and, lean in and make sure everything was okay to have my team at a place and the organization at a place where I could walk away for 12 weeks and guess what things didn't fall apart.

They went just fine without me almost to the point where towards the end of it, I was like, Do they even want me back? I'm like, am I even needed there anymore? there was the enthusiastic, Oh my God, she's back. And plugging back in, but I know a lot of nonprofits, a lot of philanthropy don't have those programs.

And I would advocate very strongly that you should invest in your people in that way. It is a phenomenal gift that you're giving a person to their family That will truly pay dividends for the organization over the long haul. So those are just a couple of examples, Erin, that I would lift up if I hate the word balance.

I think it is impossible. I think it is, there's no point to having a debate over work life balance. To me there's ebb and flow. There's ebb and flow as you're, as you are experiencing your life and the different chapters that come with it. And there's going to be times where work is going to be ebbing.

And then there's going to be times where life is, and to, Be at an organization or company or an entity that recognizes that and has built flexibility in and a culture of support and truly leaning into collaboration, teamwork, not just as buzzwords, but actual the, like actually realizing it in an organization I think makes it so you can navigate the ebb and flow in a sustainable way as possible. And to me, that's not balance, or maybe it is, maybe some would argue it is. But to me I would articulate it more in that way than I would say, that I've, I have figured out what it means to balance and have work life balance.

Erin: Yeah.

Casey: To me it's elusive. 

Erin: No, that word can sometimes make it feel like you should be, which is the SH word in coaching. You should be aiming for some standard that feels untenable for most. And what I hear you saying, and this is sometimes how I relate to my own journey is like, over periods of a lifetime, there might be a need to shift your relationship with your work, and your work might be able to shift with you, and sometimes it doesn't.

And you need to bring your talents elsewhere. And it sounds like Greenlight has really continued to meet you where you're at throughout your journey, which is a beautiful thing. I also heard you lift up the power of the guilt factor, for working parents or caretakers.

It's real. We had more time, so there'll be part two, folks. I would definitely want to dig into that because it sounds like you've recognized that and you've evolved your understanding from it and not everyone has, I was just talking to someone who's preparing for a busy travel season in the fall and I was sharing with them like and I think this came up in our chat, too, Casey, is like, I always used to get so stressed, like, the week before my travel, because I knew it was coming, it was going to be stressful for everyone, and then once I was in it, I was in it, once I was back, things were fine, and my son had grown up in ways that I didn't expect, and I was like, oh.

That was actually a good thing. Thanks to the support we were able to provide, but you also talked about the importance of partners, both within work and your life. I appreciate you putting a fine point on that. He's a special guy for sure. We could do a whole episode on him too, 

Casey: I hope he listens to this. 

Erin: I know we have to start wrapping up, but there's at least one more question we wanted to ask. So I'll turn it back over to Scott.

Scott: This has been a fantastic conversation, Casey, and I'm going to introduce a question that may be a little tough, so if you have to take a moment, what's one of the best pieces of advice that you've ever received or given? And it can be professional or life. I know

Erin: But not about balancing them because we hate that word.

Casey: I know. 

Erin: Don't say it. 

Scott: That's right.

Casey: Can I cheat with two?

Erin: Sure can.

Scott: Yes. 

Casey: I did have a mentor say to me, Any room that I enter. And these days, I guess we have to take it from a virtual and in person uh, lens. I should always ask myself and potentially in the nature of the room, who's not in the room and who should be. So I think that's one that I've held for probably 15 years now.

 And it is that question of who is in the room, who's in this conversation, who's in this decision, who that and that, that should be, that's not at the table that's not in the room. It also, when Hamilton came out and from where it happened, it was light bulbs.

And that was Ethel's advice well before that time. But that's probably 1 that I would say always comes back to me. Green Light has served me well. And other instances have served me well. And I think especially. As Green Light has made a commitment and my own values and commitment around racial equity in particular.

I think that's a very important question to be asking. So that would be 1. I think. Advice that I have been given, but I also in part, because I mentor a lot of young women. Or early on in their nonprofit social sector careers. To be curious, I think be curious and open to what you might not expect and what might happen. So being curious, like asking questions, really investing and wanting to learn and about things that you don't know.

 Being curious is an acknowledgement that I don't know everything. And I never will probably know everything but I am interested. So I think that's one part of it. But in tandem with that, like being open, when I was in college, high school, college, grad school, venture philanthropy didn't exist.

So I could have never picked this as a career back then. Right? Like how would I, it literally did not exist. And so I have, I found when I'm mentoring, particularly young women they have like the next 10 years mapped out or want to have the next 10 years mapped out of their career. And then I should do this and I should do grad school and then I did this and then, and I, I like, wait a minute what about life?

Like, what about. Life's curveballs or love or opportunities to try this or do this, or you volunteer here and realize that you actually have a passion for this. How are you accounting for that in this really roadmap plan that you have? How are you accounting for the side roads? How are you accounting for the exit?

Um, and I'm not saying to not have a North Star. I'm not saying to not think about your future and think about how you may want to get there, but, like we say, with any good strategic plan, if a strategic plan goes from A straight line to B, it's probably not. There should be curves along the way.

And I think about that for how our life maps out, probably how our career careers map out. I never could have predicted my career path. And where I've ended up 15 years ago, let alone 20, 25, 30 years ago, and. And thank goodness I did some of the things you do, which is have mentors stay in touch, But I also was open to those curve paths and the exits and the U turns frankly that sometimes come into play when you don't plan for them. And it's actually probably those moments that I've learned the most from and brought the most joy from. 

Erin: That is a beautiful summary of the conversation to date and commercial for part two, which we're now all locked into because you've left them wanting more Casey. Oh,

Scott: Yeah, I'm so glad you shared both of those, Casey. They were fantastic. It made me feel really quickly. It made me think of the first piece of life, who's not in the room. So in Massachusetts, the governor has a tradition of putting a portrait in his or her office of someone, who they're drawing inspirational leadership from, or, they're signaling that is important to them and no surprise.

It was two high school students who suggested to our governor, she actually asked for public feedback that the frame be empty for those who are not in the room in meetings that the governor is holding. And I think it's that same sort of mindset. So I love that.

Casey: I just, you gave me chills. God, that's a phenomenal recommendation from young people who are so wise beyond their years. And a very powerful imagery for the governor leading and how she might lead in Massachusetts. So, thank you for carrying that. I might actually steal that.

Scott: No, it's always the youngins, right?

Casey: Oh,

Erin: young ones. We were young ones. We were them. Now we listen to them. All good. Casey, thank you so much for spending this time with us. It was a real joy. We appreciate it so much.

Casey: This was a gift. There's not many times that I get to pause or any of us probably get to pause and think, think back along the paths, along the way, when and how and why we made different decisions and choices. And so, I deeply appreciate the space that you all have provided.

I hope that it's been helpful for those listening and I'm really excited to listen to your other episodes and episodes to come and see what I can learn from our other leaders and just deep gratitude for both of you and what you're doing.

Erin: Right back at you.

Scott: Yes, co sign. Thank you, Casey. 

Erin: Have a great day. 

Casey: All right. Bye y'all. 

Scott: My gosh, what a gem of a human being.

Erin: Exactly what I think of every time I talk to her. She's special in all ways.

Scott: And, you know, it was just thinking about : not every classroom has four walls, as you so smartly pointed out, and just thinking about some of the best teachers who've, I've had the fortune of calling colleagues when I worked inside formal school settings have so many of those characteristics that Casey has, whether it's like the growth mindset, whether it's the keen attention to empathy, the making sure the people around you feel known.

Yeah. She's just like a natural teacher.

Erin: Awesome. Well, this is fun. Once again, Scott.