Episode 32 – Commit to Collaboration with Brit Gilmore & Caitlin Crosby

It is hard to imagine a more effective and inspiring commitment to collaboration than that of Caitlin Crosby and Brit Gilmore. These women have created the wildly successful and impactful brand, The Giving Keys. The Giving Keys, through their social impact employment model, support job creation for people transitioning out of homelessness. This week, Jessica gets deep with Caitlin and Brit and dives into their relationship, collaboration, drives, and dreams. Also, this week continues a special series of shows where Jessica takes us through the themes of her brand new book, “Imperfect Courage,” one chapter at a time!


Jessica: Hey there, it’s Jessica Honegger, founder of the socially conscious fashion brand, Noonday Collection, and this is The Going Scared Podcast, where we cover all things impact, entrepreneurship, and courage.

Today’s guests on the show pretty much summarize the entire purpose of my podcast. Caitlin Crosby is the founder of The Giving Keys and Brit Gilmore is the president of The Giving Keys, and together they are collaborating to create an impactful business called The Giving Keys that is truly changing lives around the world. This podcast truly does encompass impact, entrepreneurship, and courage.

The Giving Keys employs people who are transitioning out of homelessness to make necklaces from keys with engraved inspirational messages like Fearless, Hope, Believe, or Courage. And when the wearer encounters someone else who needs the message, they are encouraged to embrace their word then pay it forward by giving their product to a person who needs the message more. They’re then invited to share their giving story on the company website. Since it began in 2009, The Giving Keys had provided job opportunities to more than 70 people who have been affected by homelessness, helping many move into permanent housing, and collected thousands of Giving stories. They have sold more than 500,000 keys.

I wanted to have both Caitlin and Brit on the show. As a founder of a socially conscious fashion brand, that is similar to The Giving Keys, I’m so aware that a brand is about so much more than the founder. I love the quote by Maya Angelou that says, “I come as one, but I stand as ten thousand.” So I wanted you to meet one of the really important people that’s helping The Giving Keys to grow and create a huge social impact, which is Brit—their president. And Caitlin and Brit have such a beautiful relationship. They truly have committed to a life of collaboration. And that is what the topic of this podcast is.

As you remember, we are covering a special series. This podcast series is all about Imperfect Courage. Imperfect Courage is the book that I launched about a month ago. I hope that you have grabbed a copy. If you haven’t, you one. Because this series goes chapter by chapter through the book. And the chapter that we are covering this time around, is Chapter 8, “Commit to Collaboration.” Brit and Caitlin are such a powerful example of what it looks like to come together to create a culture of collaboration that is creating a culture of collaboration among the homeless and among other organizations in Los Angeles where they are based.

So without further ado, here is the dynamic duo of Caitlin Crosby and Brit Gilmore.


The Giving Keys 101

So, I’m having two guests on. I’ve done this one other time before, but in order for everyone to know who’s talking, Brit, why don’t you share a little bit about you, your family, where you’re from, and then Caitlin will share a little bit and then we’ll be able to know. You guys have actually really distinct different voices. So, I think we’re gonna be good with this, but let’s just start with a logistical thing.

Brit: Nice. Awesome. Yeah. This is Brit and I am originally from the Detroit area. I moved out to LA almost nine years ago now, which is crazy. And I really started out in the fashion industry knowing that I wanted to do something where philanthropy and fashion were merged. And came out to LA on a scholarship to the Fashion Institute here in downtown and met Caitlin a few years after I graduated.

And it was just this really cool alignment of the dreams and desires that I had had from graduating high school and wanting to move into a really impact-driven fashion company. And where The Giving Keys is at and where Caitlin was at with getting that company built and it just, yeah. It aligned really, really well. And it’s been six years almost…

Jessica: Crazy.

Brit: Since I came on board.

Jessica: Crazy. Crazy. OK. Caitlin, what about you?

Caitlin: Yes. So, born and raised in Los Angeles. Would you want me to tell the origin story of The Giving Keys yet, or just more of my background before Giving Keys?

Jessica: I think we know now. OK. Brit’s got probably a bit of a peaceful, grounded voice. Caitlin’s got the excited Hollywood voice. Can we just say that? So, I think our listeners now know who is who. OK. So Caitlin. Yeah. I would love to hear, first of all, I’m just super excited to have y’all both on today because I feel like so many of us know who The Giving Keys are, especially this audience because we obviously Noonday Collection is a social impact brand. But I feel like as founders, Caitlin, you and I, we get the spotlight a lot and a lot of times it’s like we don’t get to bring it out into the open how this takes a village. We did not do this on our own. This takes a village and I feel like so many women are afraid to ask for help or to reach out to…in order to reach a giant vision, the reality is you’ve gotta have other people to come alongside of you. And so, I’m super excited to get both of you guys on the show today and to talk a little bit more of what that looks like. So, before we launch yet, give me the 101 of what Giving Keys is. But then I actually wanna just step back a little bit and just hear the story behind the story about…a little bit about your growing up. But yeah, go ahead and give us The Giving Keys 101.

Caitlin: OK. Giving Keys 101 was started about 10 years ago. I was on tour doing music, writing songs and I had a website at the time called “loveyourflaws.com” about body image issues. And no matter what I did in entertainment, it was never about entertainment. I actually hate performing. It was always about putting out messages, certain messages into the world, whether it be about eating disorders or insecurities or religion or homelessness or social justice or whatever. I was always just really wanting to use art and creativity to put out topics and issues that I’m passionate about.

So, at the time it was “Love Your Flaws” and my album was called “Love Your Flaws” and I had t-shirt’s and bags and key chains and everything said, “love your flaws” on my merchandise tables on tour. And one day in New York, passing through on tour, the hotel key was…I thought it was really cool. It was this big key. So, I put it around my necklace, got compliments on it. It was just something that I wore as part of my touring outfit, whatever. And then I was at a locksmith one day and the person in front of me got numbers engraved and I said, “Oh, do you have letters? Can you engrave “Love Your Flaws” on this key?” And then I saw all these old used keys on the side and I said, “Oh, while you’re at it, can you engrave hope, love, faith, dream, belief, fearless, breathe, let go on these other keys?”

Jessica: You’ve got that down, girl! I mean you just rattled those off.

Caitlin: And yeah. “So, how much would you charge me?” So he said, “$8.” So, it was $3 per key, but then $5 to engrave letter by letter what the word would be. So, then after that went to different bead stores and bought different jewelry and clasps and this and that, and would make jewelry out of them with my cuticle clippers and my tweezers and would make them on planes and backstage, etc., in my hotel rooms and would start selling them on tour. And then they started selling out more than my CDs.

So, I knew that people were really resonating with the words and because I had gone all around the world and took thousands of pictures of people holding up their “love your flaws” pictures, I was very comfortable and passionate about just people’s journey in life and what they’re going through. And so I was always going up to them talking to them about their story. So, this was just kind of like an extension of love your flaws in that way of saying, “What are you going through in your life? What word do you need to embrace?” So, then for a few months, it was just that. It was just about what word do you need?”

But then, it morphed into…after touring and meeting so many people that needed these words as well as myself and I would wear a different one every day, and I would give them away to people and I was like, “Ooh, this should be the thing. This should be what it’s actually about. It’s not just about us. Let’s keep our eyes open for other people that are hurting and need the words on these keys too. Let’s make it a pass it on, pay it forward movement.” Because I was always about movements and I was always about wanting to start something that will change the world ever since I was in elementary school, junior high, I was always just wanting to be radical and start something and do something that will help people.

And so I think, yeah. So, it started that way. And so people would write me on MySpace at the time. “OK. I gave my key away like you told me to. So and so was about to commit suicide. So, I gave them my key. So, and so was…my mom had cancer, I gave her my keys. Someone was being bullied, I gave them my key.” Yadda, yadda yadda.” And so I was crying all the time I was like, You know what? I should make a website to store all of these stories so other people can read them other than my mom and I reading them and crying all the time.” So, then I knew that something was really special with these keys and so I thought I want the money to go to some sort of charity and I waited for the missing link for about a year or so.

And then I met this young homeless couple on Hollywood Boulevard. I was leaving church one day and I left Bowlings, they were planning an Invisible Children documentary. And yeah. So, I saw this young couple and they were holding up a sign that said, “Ugly, broke, and hungry.” And it really caught my eye and it looked like a love your flaws sign. And so I went up to them I was like, “Why does your sign say that?” And then got to talking and I ended up taking them to dinner. And so during dinner, I had my “aha” moment that I should start paying them to engrave the keys instead of a locksmith.

So, then little by little, I just hustled, hustled and got them into stores and would sell them at a million random events. And then they saved up enough money to get their own apartment. First, they were just staying in a motel then they got their own apartment, but when I met them, they literally lived and slept in a dumpster in a cardboard box. So, anyway, that’s the origin story. So, that’s the story. But in a nutshell, our mission is: we put out products that have inspirational words on them, not only keys, now we’ve expanded, but the whole premise is: we employ people that are trying to transition out of homelessness. So, the more we sell, the more jobs we can create and the more people we can try to get off the streets.

“The whole premise is: we employ people that are trying to transition out of homelessness. So, the more we sell, the more jobs we can create and the more people we can try to get off the streets.” Caitlin Crosby on The Giving Keys

Jessica: I just feel so much kindred-ness with y’all’s mission because so many social impact companies are give back, but they’re missing that piece of the actual job creation. Creating jobs for vulnerable communities is no small thing. It requires a lot of effort and grit and really taking a long-term view because people fall and then they have to get back up again and I love what you guys do. Now, tell me what’s the timeline? Because when did you start that? When did you take that initial couple out to dinner and realized, “I’m gonna pay it forward towards homelessness?” And then you started selling them everywhere. And then catch me up between then and then to when you met Brit?

Caitlin: Yeah. We just had our 10-year anniversary, which is incredible, of when it first started. So, in 2008 is when I first started making them and selling them on tour. And then I met Rob and Sarah, either in 2009 or 2010, somewhere in there. I think it’s on a website somewhere. When I last asked Sarah. And then the timeline of meeting Brit was…well, I’ll back up a little bit. Once we started getting traction and the first couple PR hits we got was super helpful and then we were in maybe, I don’t know, 50-something stores around the US or world.

And at that point, I just had a production manager, a director of sales, and then a few people making them and maybe a handful of random people here and there, but that was pretty much it. And Brit was my one friend that was in fashion that I knew was actually a good person and have a good heart. And so we got together a few times and then this one day, our production manager quit and I texted a few people, “Does anybody know anybody? We pay pretty much nothing.” But no health benefits or anything like that. It was still at that level.

Brit: “But we’re changing lives.”

Caitlin: Yeah. But we’re still in that point, I guess in, I don’t know, at that point in 60, 70, 50? I don’t know. Yeah. And then and so I texted a few people, and said, “Does anyone know anybody who wants to be a production manager?” And Brit was like, “I actually might be interested.” But Brit had a really great job at that point. She was…well, I’ll let her tell her story. But from my point of view, I was like, “Oh, really?” Because I knew I remember hearing that her job had health benefits and all of these things and we definitely didn’t have that at that point.

So, the fact that she said that she was interested, was awesome. And then she knew so many people like this guy, Daniel who was one of our best guy friends and she brought him to then be the production manager at some point and help out and he was volunteering. And then I remember we had a consultant, which was also one of Brit’s friends from London. And I was so stressed and I remember he said, he’s like, “You need to pick one person that you trust more than anyone here.” Because I was getting emails and texts and calls from all the different people whether it be our director of sales or production or whatever. And I was like, “I’m going crazy. This is so stressful.”

And he’s like, “You need to pick one person that can be your filter that everybody goes to her and then she can just go to you so you can get the information from her and that can be your funnel. And who do you think that person should be?” And I was like, “Brit.” She’s definitely the one I trust the most big-picture-wise that I feel like can go above all of the departments. And so that’s how that started.

From Passion to Mission

Jessica: So, did you have this like because I know for me, Noonday, it was like I was just selling out of people’s homes and it just took off and suddenly it was like, “Oh, wait a minute, this is a business. I need to make this into a business. I need to treat this like a business.” Do you remember a decision point where you were like, “I’m gonna scale this. This is gonna be a business, this isn’t going to be just like, oh, like keys, fine.” Do you remember that decision-making point

Caitlin: Yeah. I think also I was in a different space because at the time, because I was acting and doing music like this, I wasn’t even thinking of it as a business because it was just my like, “Oh, this is like my charity.” That’s how I saw it. As “this is my give back in my life.” A personal thing and I wasn’t taking any kind of salary or anything like that. I didn’t think of it in that way because I was making money in doing the other stuff. So, I think the thing that shifted was I had already been paying this guy who was doing our website, he was also our production manager, and then some of our employees that were transitioning out of homelessness.

But this one day I did an MTV. I was on an MTV show at the time. And so MTV was really great at giving us our first little push of press. And then I met…oh, no. It wasn’t that. It was I met this guy through this thing called Summit Series and he had just launched on Huffington Post when the Huffington Post was the coolest new place that everybody was getting their news from. At the time, it was the number one news source. And he’s like, “I want you to write the story.” Because he loved the story and so I wrote the story of The Giving Keys and how it started and the mission and everything and they put it on the front page and it got a shmillion views and I got hundreds of emails from stores all over the world. And I was managing the stores that we had myself at that point, which I loved doing, but it just got like, “There’s literally no way I can respond to all of these emails.”

And so that day I remember when the Huffington Post came out, I was freaking out and I was at some dinner party for my friend that got engaged and next to me was sitting this girl, Elizabeth. And I was telling her about what I was doing, and I was like, “I need to find somebody who can head up my sales and take care of all of these stores.” And she was like, “I think I’m your person.” And she was Miss Louisiana. And she moved out here to do acting and modeling and it wasn’t really working out for her. And so she’s like, “I think I’m your person.” So, we met the next day at Don Cuco, a Mexican restaurant, and she gave me her resume over chips and salsa and I was like, “You’re hired.”

And she was like “Great!” And so she really helped. So, I think that was the first time where it felt like more of a business. Also, my business manager at the time who would do all my finances, I would just pay the first couple cash and then he was like, “We can’t do this anymore. Caitlin, we have to set up…” Because it was getting too crazy, we had cash everywhere and not being able to track things. And yeah. So, I think once he started he’s like, “We need to turn this into a real thing.” And I wanted to turn it into a non-profit at the beginning because that’s what I used to call it because I wasn’t taking any money and I didn’t really know what a non-profit was other than it’s some sort of charity.

I didn’t really have a name for what it was that I was doing. So, I think it was a combination that was the time I was a business manager saying, “OK. We need to do this for tax reasons and to have some organization.” And then also, especially once I had Elizabeth and the guy Gilbert at the time, having to pay them in a proper way other than cash. So, that made it official. And then getting in the showroom…

Jessica: Getting pressure. When you start paying cash, you know you have a business. So, it’s OK.

Caitlin: Yeah. That’s a really funny quote. But yeah. And also I think at the beginning, and this was before Elizabeth came to when we got into a showroom, even though we’re already in stores when I first learned about the showroom world and reps, that felt real too. Pitching to a bunch of reps that were then going out and pitching other than me, that felt more real.

Jessica: Cool. I love that. It just kind of took off without you sort of, and you had to start grabbing the tail and letting it drag you a little bit.

Caitlin: Oh, yeah.

Cultivating a Career with Impact

Jessica: OK. Brit, so Caitlin has started this thing. It’s been a few years, she’s not paying cash anymore, which is a good thing. She’s got employees, legitimately and you come in. But I’m wondering what drew you, because I’m sure it was still a startup. You probably weren’t getting paid the giant bucks that you could in fashion. So, tell us a little more about that.

Brit: Yeah. I think that’s a really easy answer. It was the opportunity that was most aligned with the dream that I had for my career. And I had been in the fashion business really since I was 16 years old, I worked in retail and then went to fashion school and then worked in a bunch of different fashion jobs and I had gotten to the point with the fashion industry where it just didn’t feel fulfilling and I hadn’t found that opportunity or created that idea that really merged impact and fashion together. So, this was one of those moments where I was just like, “Oh, my gosh. Everything just aligned.” It was really perfect in terms of just what I wanted and what The Giving Keys needed at that point in time.

“It was really perfect in terms of just what I wanted and what The Giving Keys needed at that point in time.” Brit Gilmore

Jessica: And how did you know Caitlin? How did you guys meet?

Brit: So, we met through a mutual friend at his birthday party, actually. And it’s a funny story because we were at this club in Hollywood dancing and I think our first conversation was about our dance moves. And yeah. It was a context that we don’t find ourselves in often now, but we were just there celebrating a friend’s birthday and we connected. And I think maybe the next time we saw each other is when we talked about Giving Keys and what she was doing with that and what the vision was and I let her know I was really interested in volunteering my time if I could come down to the office and support in any way. I just wanted to get involved in whatever capacity she needed.

And within a few months is when the production manager that she had at the time had stepped down and she was looking for somebody to fill that position. And it happened to be…I think the really cool part of the story is that the day that she reached out to me about that job was the same day that my employer at the time laid off 35 of its 50 employees. And so the timing was just really serendipitous.

Jessica: OK. So, you have a background in fashion and merchandising, but you’re now the president, so you’re playing definitely more of an operational, managerial role developing others. Has that been a giant leap and do you feel like you found your sweet spot or are you still getting to play in fashion? Tell me a little bit about that.

Brit: Yeah. I think. So, my journey was production manager to then web manager to then managing director and then president. And I think the parts of the…I guess the way I would have described my job for the majority of the time that I have been in it is that I was the person looking at whatever the next initiative was and figuring out how to organize the team around it.

So, Caitlin’s been the visionary of the company and has really cast a lot of ideas about where Giving Keys could go, and we typically don’t have the infrastructure for each of those ideas in place. And so, the first thing that I did was re-platform the website and really get that digital experience and the ability to purchase online more streamlined, easier. Really get the site to be something that aligned with what the brand stood for and telling that story in a digital way and then getting the team onboard and building out our HR program and getting production more organized and just each of those new frontiers or areas of the business needs a lot of attention on the front end to get up and running and then you hand it off to people that can effectively manage it or coordinate it.

So, I felt like that was a lot of my job was like that operational, let’s create some infrastructure and some disciplines. But it’s funny because I think there’s also this other side of me that is creative and I love product and I love photoshoots and I love the more artistic, creative sides and…

Caitlin: And she’s so good at all that too.

Brit: Thank you.

Caitlin: I wish there was like five of Brit because even though she has had to do a lot of the technical operations and managing the people, she’s really the only person that I also trust to do anything creative.

Jessica: She’s a unicorn. You found a unicorn. Every business owner needs a unicorn.

Caitlin: I know. I just wish there was another one.

Jessica: Caitlin, I will not steal her from you. OK? I’m not kidding. I’ve had some moments in the past. I’ve got, oh, Brit. She looks like she’s killing it. I could use a Brit.

Caitlin: Yeah. I know. Everybody can use a Brit. Seriously, I think if I could clone her so then there’d be another one so one Brit can do the all the impact and partnerships and help with that. But then also help with photo shoots and design and products and spend time dreaming up things like that as well as managing people because she has the heart to. So, she can talk with people about how they’re feeling and try to manage their emotions.

Jessica: So, I’m curious, Caitlin, because I remember at the beginning of starting Noonday and we’re starting to hire people and I’m like, “Oh, I really like managing people. This is not…I’m not a good manager because I just want people to get it and move on. And I’m not good at managing people’s feelings.” And I think it’s mainly because I’m just like, “We got stuff to do. I got to go after this vision and you just need to run fast behind me and if you can’t keep up, I don’t know what to do for you.” So, was that similar? Or I think you’re a little bit more of a feeler than me. A little maybe more caring about others.

Caitlin: Too much. It like keeps me up at night.

Strength in Collaboration

Jessica: So, maybe yours is the opposite where you’re like, “Oh, my gosh. Managing people will swallow me up alive.” And you couldn’t do the whole, “Hey, you’re not performing. This isn’t working.” When did you realize this is not…managing is not a role…and then you realized that Brit was actually that, that she really thrives there?

Caitlin: Oh, from the beginning. And I used to feel…well, I think I’ve gone through seasons like at the beginning because I was doing so many other things. I wasn’t even…I would manage our first guy that was doing our website and our production manager and the girl that became our director of sales. But I wouldn’t even think of it as I was managing them. It was just we’re all working together and getting, “Hey, this needs to get done. Let’s do this, this has to happen. Have you done this?” Da, da, da, da. So, I didn’t even know the language of managing people. I didn’t know what that really ever meant. It was just like, just got to get stuff done.

So, but then I think once I learned more about business as it all unfolded and realized that there started when Brit came along and started having meetings with people that she was managing because we had to make an org chart to say who was reporting to who. And then I started seeing that. So, there was never really an opportunity to have those meetings. I guess I would…like even when I would have if…Brit technically reports to me, but I feel like the way that I manage her is how I did it at the very beginning with the other people outside. I don’t feel like I’m managing them, I just feel like we’re all working together to try to get things done. So, I think for the first time, I technically was managing somebody for just a few months and I was like, “I have no idea how to do this. I don’t know.”

“I don’t feel like I’m managing them. I just feel like we’re all working together to try to get things done.” Caitlin Crosby

It just felt like a weird new pressure. I don’t know the language that I was supposed to speak and it made me feel better because I was feeling bad about that for a while. And then I think once I had talked to a few other people like this one guy, he’s…I forgot his name, but we did a TEDx talk together at this really cool advertising agency called 72 and Sunny. But he used to head up. He was…he worked for huge companies and he was like “Oh, yeah. I do not manage anybody.” He goes, “A lot of people like me and a lot of people like us, we just should not manage people.” He goes, “I do not manage anybody.” So, I think the more I would hear things like that, that made me feel better that it’s just, “I’m not supposed to do that because it’s not going to be effective.”

Jessica: That transition was hard for me though. When I realized maybe because I felt like I was supposed to be good at everything for a while. And yeah. You feel like, “Oh, gosh.” You want your people to have good managers. But I think in order to scale a company it’s realizing your weaknesses and your strengths and then finding those people that have those strengths, which is so cool that you found that and bring it.

“I think in order to scale a company it’s realizing your weaknesses and your strengths and then finding those people that have those strengths.” Jessica Honegger

Caitlin: Yeah. And I think it’s what you were saying at the very beginning. To answer your question, ahead of time, even though you asked it earlier, I think it really is all about a team. And I think I don’t like…it’s uncomfortable for me when people come up to me, whether it be at conferences or wherever, a pop-up trunk shows whatever and people are super complimentary like, “You’re inspiring” or “thank you.” Or whatever. And it’s like I almost don’t feel like I can receive it. I’m a little numb to it just because I’m like, it’s not about me at all. This is…

Jessica: It takes a village.

Caitlin: Everybody. It’s everybody on our team, equally. And so, I don’t feel like…I probably feel like I should take a little bit more pride in it, but I really feel like I don’t like when people are complimentary. And that sounds maybe bad, but I just don’t feel…

Jessica: You want them to see the village? Yeah.

Caitlin: Yeah. I just don’t. It’s just not about me at all. I really don’t like. And I feel like sometimes you have to make it about you whether you’re doing podcasts or speaking and so it’s like you’re telling the story so that it ends up being about you. But I don’t feel that way. Like it’s how you have to tell the story, but I know that, and I want everybody to know, that it is really about every single person in our building. We all need each other. We all need each other and everybody at our office works so hard. And I think now I’m a new mom and certain things that if I stayed as late as all the people stay in the office or get in as early as other people do, I literally would not see my baby and I do struggle with that so much right now. But it’s all the extra hours that they’re putting into the office is taking them away from other things in their lives.

And well, I know we all do also once the baby goes down and people are done with dates or this or that, we all a lot of times do emails at night as well also. But I think the hours that they’re spending and the grind and the hard work and the meetings and every single day is…so it’s really about the whole team.

The Giving Keys Mission

Jessica: It’s a sacrifice. It is. And I think that’s how you’ve been able to scale and build. Right? Because you know it’s not all about. I wanna go back to this issue of homelessness, Brit, because was that something that you were already passionate about or did beginning your work with Giving Keys give you the passion? Which came first?

Brit: Yeah. I think, in general, the whole idea of people living in poverty, whether that’s homelessness or internationally, people experiencing severe poverty. That was something that became really important to me pretty early on. And if I was gonna identify the source of that passion or that desire for justice and for there to be equal opportunities for everybody, I would say it really did come from the family that I grew up in because my dad was a pastor and my mom was always really involved in community development work. She still runs a food distribution program for families living in neighborhoods in Detroit that are just underserved and don’t have access to food. So, I grew up with parents that really valued that and demonstrated that and brought us into community development work and service-driven projects really early on.

But I think the pivotal moment for me really was on a trip when I was in high school, I was a junior in high school. I went to India, London, and Thailand one summer. And I remember being in India and walking out of this coffee shop and I saw this little girl who was probably six or seven years old. She had one and a half legs and was holding a baby begging for money. And I remember being so shocked at the reality that people were walking past her like she was invisible and thinking, “How could you walk past a little girl begging for money?” And I came back from that trip really, really, really inspired to do something. And so, I told my mom, I was like, “Can we do something? I’ll throw a benefit concert, let’s start a non-profit. I just wanna raise money to send back to support anybody who’s doing work to support these kids that are living on the street in India.”

And something else I find really important to say in attachment to that story is that I grew up in the U.S. around adults experiencing homelessness and I didn’t necessarily live in a culture that was nurturing the idea that we should be stopping for these people. And I remember my family cared about that, but I guess what I’m saying is in the U.S., we treat people that are adults experiencing homelessness like they’re invisible all the time.

Jessica: Yeah. We do.

Brit: And so it was like the same thing with that girl, that little girl. Well, it was crazy to me that their culture was desensitized to this little girl experiencing homelessness. We live in a country where we’re desensitized to adults experiencing homelessness and we’ll walk past them and not acknowledge them. And to further that point, I was working with a friend on a project in Bethlehem and I was staying with a Palestinian family while working on that project. And I was doing that while I was working at the Giving Keys and started sharing about my job. And I remember the father of the family being blown away that we even had a need for an organization or a business to create jobs specifically for people that were transitioning out of homelessness because they would never allow homelessness in their community.

“We live in a country where we’re desensitized to adults experiencing homelessness and we’ll walk past them and not acknowledge them.” Brit Gilmore

And we’re talking about Bethlehem. This is not a part of the world that is well-served or has means. And so, to hear him coming from a place of poverty saying, “Oh, my gosh. If we saw someone on the street, we would 100% stop for them and invite them to stay in our home.” You just would never let that happen. So, I think it’s just good to audit what we feel is normal and take stock of that. So, that trip to India really was the moment that instilled the desire to commit my time and energy and career to doing something to stop that even though it wasn’t homelessness in the traditional sense.

Jessica: Yeah. I feel like we all have that moment. I definitely had it, which I write a lot about in my book. It was when I went to Kenya when I was a freshman in high school, and I saw a woman running a brightly colored fruit stand and it was in a Nairobi slum and I realized jobs could be a way out of poverty and then before that I had gone and worked in inner city, D.C. for a summer with a bunch of other kids and had realized there is poverty in the United States and it’s two miles from the White House. And I feel like we all have those moments where we wake up, it’s what we choose to do when we do wake up. Caitlin, I’m curious, I know you just took this couple out to dinner. OK. So, a lot of people would have passed on by in that moment. Do you remember your first moment you said as a kid, you were on fire? Tell us about that.

Caitlin: Well, I don’t think it was ever an “aha” moment. I think I was born and raised in LA. And it’s so funny, my mum just wrote me a text message a week or so ago and she said something like, “Yeah. Your whole life since you were a little girl, you were just obsessed with injustice and you were obsessed with Martin Luther King and you were obsessed with Rosa Parks and you were obsessed with people that were experiencing homelessness.” She’s like, “Those are your three main things that you were just not OK with.” And she’s like, “Every year you want to do a report on Martin Luther King. And even if you just did a report on Martin Luther King in a different class or different subject, you somehow wanted to bring it back about Martin Luther King or Rosa Parks. You were obsessed with that.”

So, I think and I was always going up to people that were on the street, whether it be buying them food or just having conversations with them or giving them hugs or ask if I could pray with them or bring them somewhere, bring them to youth group with me or church or whatever. And so it was just my whole life I had just always been like that. So, it wasn’t one particular, it wasn’t like, “Oh, I met this one.” The first couple Sarah and Rob, that was anything new, it was just normal.

Focusing on Humanity

Jessica: OK. That was just how you lived. You were like you’re hurting, you’re human, you’re not an object, you’re not less than and so you humanize people. So, let’s talk a little bit about that because I do think and I’m in this work of justice and yet, I do get uncomfortable around homelessness. I’m like, “Oh, I wanna do something and I don’t know what.” So, aside from buying The Giving Keys, which we will continue to do. And I love all the new stuff you have coming out. I love the earrings and…

Caitlin: Oh, it’s so cute.

Jessica: So cute.

Caitlin: And so many have color. I’m so excited about all of our colorful things.

Jessica: So fun. So fun. So, I love all the new products. But in addition to that, because I know you guys are, in addition to the Giving Keys, are really wanting to be the leaders of this issue in LA, especially. So, what are some tips maybe Brit, you share a couple, Caitlin you share a couple of what do we do? The complexity that happens in our souls when we encounter homelessness.

Caitlin: I love the idea of I heard someone say once if there was only one homeless person, everybody would be like, “Of course, we got to help them.” But because there’s so many, I think people get so overwhelmed that they don’t do anything. They’re frozen because they’re so overwhelmed by how many people this issue affects. But yeah. But just think about it, there was one person that you pass in your car and they are holding up a sign, I think it would just be natural and normal to be like, “Oh, of course, here’s some money or here’s some food. Do you want a sandwich? What can I do? Can I help?” So, I think, like you said, it’s just about human-to-human contact interaction and genuinely caring for what they’re going through. And I think…but, obviously to be balanced and have wisdom, I think you can’t trust everybody.

And so, I think it’s a case by case like sometimes there’s somebody that is outside of 7/11 and I’m not going to say hi or buy them food or talk to them because I don’t feel safe and I don’t feel like that would be wise. You can just have that discerning feeling sometimes when you see somebody. And so I think it’s just about when your heart tells you, “I wanna connect with this person and encourage them.” But as far as the issue of homelessness, other than buying our products, which does directly help the issue I think what people can do in their communities is just go up to people and have conversations with them and ask if they’re hungry and buy them food or buy them blankets or shoes or underwear or toothpaste or mouthwash or floss or just take and be like, “Hey, do you wanna walk over here to this Target?? Or, ”Hey, do you wanna walk over here to this 7/11 and let’s go shopping at Walmart or wherever.” And let’s just ask them what they need. And that’s a case-by-case and I think Brit can maybe talk more about.

Jessica: I love that your default though is I feel like so many of our default is like, “Oh, they’re just gonna use it for drugs or they…why aren’t they trying to find a job.” Or whatever, all of the things that you hear and I think it’s like switching the default for it to be on, “Oh, that’s a person that I could just as easily be in that position if it wouldn’t have been for whatever, fill in the blank. And just to have that moment of humanizing the situation because I feel like that’s your default and I feel like we have to actually make that switch for that to be our default in order to even be able to discern. Because otherwise, our default is always gonna be like, “They’re gonna use this for drugs and I’m out.” And we don’t even treat them as humans. So Brit, what about you?

Brit: Yeah. I really believe that there are so many phases to homelessness. And if there’s anything that I’ve learned at The Giving Keys, it’s that. That there’s so many reasons why someone could experience homelessness that have nothing to do with drugs or a criminal background but could be falling on a hard time financially. Imagine if you were a minimum wage worker or an entry-level worker who got disconnected from your family, you moved to a different city, you experience a significant medical problem and the medical bills are just so overwhelming that you can’t afford your rent, and then you get out on the street and the trauma that that brings into your life, it’s just…you just never know.

“There’s so many reasons why someone could experience homelessness that have nothing to do with drugs or a criminal background…Imagine if you were a minimum wage worker or an entry-level worker who got disconnected from your family, you moved to a different city, you experience a significant medical problem and…you can’t afford your rent…the trauma that that brings into your life, it’s just… you just never know.” Brit Gilmore

And I think that that’s the thing I would say that I love about Caitlin’s approach and really what inspired her to even be able to carry out an idea like this is that restoration of humanity, looking at people with hopeful eyes and seeing their potential and not making the first negative assumption. And so, I think in terms of ways to live that out is if you see somebody in your neighborhood that’s experiencing homelessness, that person is your neighbor. Just because they don’t have a roof over their head doesn’t mean they’re not your neighbor. They live in your community.

And so, being able to go up and just say, “Hi, I’m Brit, what’s your name?” And just starting a conversation there and saying it doesn’t even have to be a question about like, “How did you get here and are you looking for help?” It can just be, “Hi, I’m Brit. How’s your day going?” And I think that that’s really powerful and that’s a step in the right direction. It doesn’t have to be…you don’t have to have all the answers for everybody in your community, but just treating them like…yeah.

Jessica: I talk about that in this chapter, “Commit to Collaboration,” because it’s about listening and it’s about making generous assumptions because I feel like so many of us walk around with assumptions about others that we have no right to make. But if we can just come and be a listener and like, “Hey, how’s your day going?” And find those points of connection, I think that’s what humanizes people instead of project-icizing them.

Brit: Yeah. I think it’s so important, specifically with homelessness because they just don’t get treated like human beings all too often.

Caitlin: Oh my God. And think about this, guys, think about you know if you’re having a hard time in life or that week or that day and you’re going through something, whether it’s with your family or a relationship you’re in or your job or whatever. I know for me personally, sometimes I get in ruts and I feel depressed and I feel anxiety and stress and this and that. And sometimes just talking to a friend, helps so much. Even my therapist recommended that I call a friend on my way to work in the morning, so I can vent things and, or call them on the way back and just so I have a place to vent that I feel comfortable and heard and not judged. And it’s been helping me so much the more I do that. And I actually haven’t been doing it the last couple weeks and I feel a difference. I feel more stressed and I feel more depressed in all the things.

So, my point in saying that is knowing that having a conversation can help me so much with whatever I’m going through, I feel like somebody that is living on the streets, they might not have that and with whatever it is that they’re going through, which is probably really intense to be able to provide that for them, just a listening ear and the connection and so they can just talk and vent, I think that would be the goal that they would feel like their burden is lifted a little bit and they can just go on throughout their day with what they’re experiencing just with a little bit of a maybe a lighter load.

Jessica: And we all have that. It doesn’t require money or a skill or. I know for me, I’m like, “Oh, I don’t have any cash on me today.” Guys rarely do any of us have cash on us anymore. But we all have the ability to listen and just say, “Hey, do you need to vent about something today? Because I assured you’re liked. You wanna vent to me?” And that’s really empowering to realize we don’t have to have some special skill or some passion for homelessness or whatever, you just set your heart on that default of, “I want to love another human today. I have something to give.” And it takes the pressure off because I think we can either get paralyzed or we feel pressure and then that leads to inaction, which is the opposite of what we’re all called to do, to help and connect.

So, this is The Going Scared Podcast and what y’all are doing is no small thing in 10 years. I mean 10 years is no joke. There are so many people that start things and stop them, or it gets too hard or whatever. So, I would love to hear in each of your lives how you’re going scared right now. Maybe Brit could go first while Caitlin thinks about it.

Caitlin: Oh, I finally got my answer. I got. But yeah. I got it. I think.

Brit: You go first because I’m still thinking.

Going Scared as a Working Mom

Caitlin: OK. OK. OK. I think what my answer would be something…I hope this answers the question, but right now one of the things that I’m struggling with is being a new mother and the massive amount of mom guilt I’m feeling with working so much and when I’m not at the office, which is pretty much every day, by the time I get home with traffic and which I might leave, I just don’t get to spend good time with him. In the morning it’s like my time with him is I’m getting ready and he’s pulling on me. And so, I feel like every time I’m with him, he’s pulling on me to give him attention and half the time I’m on my phone having to do work emails and I feel horrible about it.

But then I simultaneously feel bad at the office and I feel like people are judging me even though no one’s said anything about this. But I just feel like, “Oh, they’re…because no one else here has kids so they probably don’t understand.” But it’s like I feel like my friends that are mom friends think that I don’t spend any time with my little boy and so I feel judgment there. But then people that I work with that don’t have kids, I feel judgment there. So, anyway, so what I’m trying to go through is, it was something that…what’s your name said? Glennon Doyle Melton. What’s her name, again? Glennon? Melton? That’s something about and I just reposted it on my Instagram. She said, “The most revolutionary thing a woman can do is not explain herself.”

Even saying that makes me want to cry because I feel like I have to be, no, but to my friends that spend more time with their kids like, “But don’t you understand that I have to work this hard because I have to provide for my family and feed my son.” But then I feel I have to justify myself to people that I work with. “No. Don’t you understand I have to leave because I literally only have one hour to be with him and I need to bond with him. Otherwise, he’s gonna blah, blah, blah.” And so, I feel like I have to justify myself and explain myself. And so, I’m really working on just being like you know what, people are not gonna understand and you are gonna be maybe judged and I have to be OK with that. And I’m just gonna try to power through and try to work on not explaining myself and just do what I know what I feel is right and what I need to do to take care of both things as best as I possibly can.

Jessica: Well, it’s deciding to quit living into the perception of other people. And it’s almost like you’re making assumptions that you’re being judged and oh, my god, I’ve been there. I have a whole that’s a huge first part of my book is about…

Caitlin: Girl, we need to get together, or I’ll just read your book. Or I’ll read your book or both.

Jessica: It’s hard. It’s hard, but I think for me, it was being able to embrace the paradox that I can be a really good mom and I can be a really good CEO. And when my daughter was five, she was finally able to verbalize all the stuff you’re feeling right now. She was like, “Mommy, if it wasn’t for you, Jalia and Daniel wouldn’t have a job and Jack wouldn’t have a home.” And she started naming these things that she had grown up now seeing and she goes, “And also, our family wouldn’t be the same if you wouldn’t have started Noonday.” And that’s when I realized that Noonday was not at the expense of being a mom, but it was for her flourishing.

Noonday was for my family’s flourishing too. And I think you just have to own that and agree because I think when you explain yourself, you’re sort of living into that. It’s like you’re explaining yourself to yourself, really. And I think when you can just be fully present at work and fully present at home because all that energy that you’re doing trying to kind of control how others are gonna perceive you is then robbing you from you at the present moment, which is all you have.

Caitlin: Yeah.

Jessica: So I love that. I think that to stop explaining ourselves is what…it’s least in an action that can help us to be more present and that is going scared because it takes a lot of courage, I think just to own the story that you’ve been given. And the story you’ve been given is that you’re the freaking boss lady, CEO of The Giving Keys, and you’re a freaking awesome mom to your son. And that’s your story and you’ve been given everything you need to be good at both of those.

Caitlin: Yeah.

Jessica: And that’s the truth. But it is hard to live into that. Thanks for sharing that. Brit, what about you?

Going Scared and Being Vulnerable

Brit: Yeah. I would say it’s definitely an internal journey of going scared. I think because I’ve been so in work mode like committed to my job that there’s been…well, I guess some backstory would be that I moved out to LA right when my parents got divorced. And I think I just kinda like hit the ground running and kind of had to in a certain sense to build a life and survive and provide for myself and be able to get on my feet in the new town. But just running so fast for so long, I think it was a way of avoiding dealing with some of the pain and just experiences that I was in before I moved out here.

And all of those family dynamics totally affects marriage and totally affect all your other relationships. And so as I’ve been in counseling and just intentionally trying to slow down and look inward, I think it’s the process of facing some of those painful memories and really allowing myself to process them at the depth at which they need to be processed because I’ve been happy to be like, “Oh, no. I’m totally…I’m good. I understand what happened.” I could explain it and be very cerebral about it, but it’s getting down into my emotions in my body. And I’m really processing some of that because I know there’s things that have gone on that have not been dealt with that hold me back. And so, I think it’s the process of just going back into some of those experiences.

And having conversations with family and friends and my husband about those things and what it’s made me believe about myself and believe about the world and believe about just the way things work. So, and I think that specifically ties into marriage and community. So, I really want to address some of those fears and my tendency to be super independent and be more vulnerable and be in a place that allows me to have the richness of relationship that I’ve had in the past and I so value but have been not seeking or valuing or prioritizing as much. So, I think that’s one thing. And then also I started a master’s program and just the process of doing work.

Jessica: Nice.

Brit: And the master’s program and investing in skillsets that aren’t as natural for me but are really important to me in the kind of work I wanna continue to do. That’s just…I took my first mid-term in however many years over a decade a few weekends ago. And I was so anxious about it, but I passed. So, it’s good. But I think it’s just a new…it’s, I did it.

Jessica: Did it.

Brit: I did it. I got an 88%.

Jessica: Mid-terms. What the hell?

Caitlin: Oh my God. It gives you PTSD.

Brit: But just wanting to balance all that and invest in the stuff I care about, but knowing that it’s gonna stretch my capacity and my understanding. So, yeah.

Jessica: Well, I think stopping and feeling our feelings is one of the bravest things that we can do and I talk about that in chapter six on the podcast with Curt Thompson, who’s a psychiatrist. And I think, ultimately, we’re so afraid of really being alone in our grief and being alone in our feelings. And I think that when we realize we’re not alone, which I love that that’s the life that Caitlin’s lived by bringing others along around her and that’s the life that you’re choosing to live, Brit. I think as we realize we’re not alone, we don’t choose isolation, don’t choose aloneness, call the person on the way home from work and vent, make the time, don’t overwork just to hide your feelings. So, stop and do the work to process these feelings.

“Stopping and feeling our feelings is one of the bravest things that we can do.” Jessica Honegger

And then to do that in the context of community, that’s where it’s at because, you know what, if we don’t do that, we’re not gonna last. And then what’s gonna happen to homeless people? Because we’re gonna be burned out. We’re not gonna last. So, it really ends up fostering your purpose to stop and do the hard work of internal, recognizing the narratives and then the external of doing that with others. It really ends up contributing to our purpose.

Caitlin: I love that.

Jessica: Which for you guys is ending homelessness. Hello?

Brit: Yes, we can’t do it on our own, but we can do it all together.

Jessica: Thanks so much for tuning in to today’s conversation. As a reminder, I am on the road right now, celebrating the launch of my book, Imperfect Courage. And I would absolutely love to meet you. It’s been so much fun to meet Going Scared Podcast listeners. Head on over to jessicahonegger.com to see the remaining dates and cities. I cannot wait to see you there. And as a reminder, don’t forget to head on over to Amazon, Target, wherever books are sold, buy Imperfect Courage, or Audible, hello! I downloaded Audible for the very first time, you get the first month for free, and you get credits to buy books. So, I already bought a couple books for free. So, head on over there too if you want my book for free. I mean, that didn’t sound bad.

Thanks so much for tuning in today. Our wonderful music for today’s show is by my good friend, Ellie Holcomb. Going Scared is produced by Eddie Kaufholz. And I’m Jessica Honegger. Until next time, let’s take each other by the hand and keep going scared.