There is an old saying that youth is wasted on the young.
Caroline Simmons did not get that message because this lady has done more in her 35 years than many have over a 65-plus year lifetime! Her latest feat? Becoming the first female mayor of Stamford, Connecticut.
She’s kicking butt, taking names and bringing lots of women with her! Listen now in the latest episode of the Think Tank of Three Podcast.
Podcast Transcript:
Reischea Canidate-Kapasouris:
Hi, I’m Reischea Canidate-Kapasouris alongside Julie Holton and Audrea Fink, we are your think tank of three.
Julie Holton:
Our guest has quite the resume. She worked for a policy lab at Yale University, which was focused on mental health, poverty, and maternal mental health for families. She’s a former visiting assistant professor at Wesleyan University, where she taught a class on state and local government.
Audrea Fink:
Prior to that, Caroline worked at the Department of Homeland Security during the Obama administration, where among a long list to duties, she served as director of special projects in the counter-terrorism coordinator’s office, no big deal. She also interned at the US Department of State for the Middle East Partnership Initiative, where she assisted with economic empowerment programs in the Middle East. Wow!
Reischea Canidate-Kapasouris:
Yeah, kind of an awesome individual, I’m just saying. For the last seven years, she served as state representative here in Stamford, Connecticut, from my district. And now is the city’s first-ever female mayor, as I mentioned before. And folks, she’s still a few years shy of 40, I kid you not. And oh, by the way, I did not mention yet. She’s married with three young boys all under the age of four. So Mayor Simmons, welcome to Think Tank of Three.
Caroline Simmons:
Thank you so much. And this is such a nice, positive way to start the morning with… my boys are screaming all morning. This is so nice. Thank you for having me. I’m so honored to be with you all, to be with this amazing group of power women today.
Reischea Canidate-Kapasouris:
Well, let’s get right into this, because I know your time is very limited as we just listed off all this stuff that you have done and what you are doing. Let’s talk about the campaign for a hot minute for running for mayor. You ran against a hometown and national celebrity and former major league baseball manager, Bobby Valentine, who had a moment or two of the ‘good old boys’ ways referring to you at one point as a 35-year-old girl in an interview, it’s something all women have had to deal with in any number of career situations. I’m wondering how often you have had to deal with the, what I call, ‘little lady’ syndrome of the political and professional spectrum?
Caroline Simmons:
Yes. So I definitely have had to deal with that, as I’m sure many women have throughout their careers. When I first actually started serving in the state legislature at the capital, my first week there, I was in the elevator and someone asked if I was the intern and how was liking my internship experience. And I had to laugh and let them know I was a new representative. And I think that it was definitely a weakness I had to overcome on the campaign; being a young woman. I think people don’t necessarily see women in executive leadership roles. There’s still a shortage of women in so many industries. And so we have so much work to do to overcome that barrier. And so I think that I had to try really hard to combat that uncertainty people had about me and that my opponent was definitely putting out there.
But I think also ultimately helped make me stronger. And I think that all the weaknesses that he tried to expose about me in the campaign could also be turned into strengths because we need more young people getting involved in our government. We need more women getting involved in our government and making their voices heard. And so we found that a lot of voters that resonated with them because our city is younger. Our city is more diverse. Our city is made up of over 50% of women. So we ended up using that as a strength of our campaign.
Julie Holton:
I can’t help, but wonder how many women in our audience have had their age used against them at some point. As if, if that’s the only thing that someone can hone in on is to say, call you a ‘little lady’ or a ‘girl’ instead of focusing around the actual issue at hand….
I remember one of my very first jobs. My boss told me I was climbing the ladder too quickly for a little girl my age. And I was like, you also are the one who is helping me climb the ladder. So am I doing something wrong or are you? But also the fact that a little lady, like a young lady, my age, it’s like, what is wrong with our society? Especially, by the way, when we’re also bombarded at the same time with all the skincare commercials and the anti-aging creams. And it’s like, well, should we look older or younger? I’m not really sure what you want me to do.
Reischea Canidate-Kapasouris:
Wait, how are you climbing a ladder too fast? No one will ever say that to, oh, you’re climbing that ladder a little too fast. That makes no sense.
Audrea Fink:
Also wasn’t Obama, the youngest president we’d ever had, and that didn’t turn out so poorly.
Caroline Simmons:
Exactly. And it’s so true. They always say that to women, you’re climbing too fast or you’re too ambitious. And as if it’s a bad thing, and they would never say that to a man. And also, what kind of message is that sending to young girls? We want young people to make their voices heard and to get involved in the community. They’re our future. And just the wrong message I think to be sending.
Julie Holton:
Politics for sure can be a dirty business. How do you keep yourself centered when things are so cynical and it’s such a competitive space to be in?
Caroline Simmons:
It definitely can be a dirty business. And I’ve had so many experiences, whether on the campaign trail, knocking on doors. Reischea, you probably remember those days when you’re knocking on a door, someone slams the door in your face, or they’ll say something negative directly to you. And I think one thing I’ve learned is you have to have a sense of humor about it because not everyone is going to like you or agree with you, but as long as you’re trying your best to do the right thing and serve the community. And I think, just being self-deprecating, I come home and my three boys don’t have any idea that I’m there. They just have a wet diaper and they want their mommy. And so that can be very humbling and grounding. And I try to remind myself not to take the negativity too seriously, because, again, not everyone’s going to like me, but as long as I’m trying my best and trying to improve people’s lives for the better, that’s all that I can do at the end of the day.
Audrea Fink:
I love that. I think it is so important that we remember how small that negative energy really is in the world. So long as you are doing your best, working your hardest, trying to create something good. There’s always going to be negativity. You’re always going to have someone disagree or dislike you, but that’s not about you. That’s about them. You just keep doing what you’re doing. I love that. Speaking of the potentially negative environments, though, you worked for the Department of Homeland Security as a woman. What was that environment like? Especially considering as we talked about the little lady syndrome, you were in your mid to late twenties, that’s a big job for a young woman, and that’s cool. Talk to us about that.
Caroline Simmons:
It was an incredible experience. It was so rewarding to get to work alongside men and women at that department who were in charge with protecting our Homeland from a range of threats, everything from terrorist attacks, to cybersecurity issues, to hurricanes. So it was a really rewarding experience, certainly still an old boys network in Washington, and at a lot of the departments.
I will say though, I was so fortunate, that when I came in our secretary of Homeland Security was Janet Napolitano, who was this incredible woman and mentor. She was a two-term governor of Arizona and the first woman, secretary of Homeland Security. Well, there were only three, but she was the third secretary, and the first woman. And so she was an incredible mentor to me about how to display strength and courage at a really difficult agency that was dealing with a range of difficult threats. And so I think I learned so much from her about how to be tough and how to be brave, and also how to bring a sense of humor. She had to remarkable sense of humor and just how to work hard, no matter what the challenge is. As long as you work hard and try to do the right thing, she really taught me that important lesson.
Reischea Canidate-Kapasouris:
We recently had a guest who was talking about understanding the rules of the game and the rules of the environment for which you are playing. You are or were at that point. Well, you still are being in the political realm, let’s face it. But in that Department of Homeland Security in a field, majority men, a more difficult area than most people would expect or anticipate; this isn’t just like the business world, right? This is national security stuff and things of that nature and beyond. So in building on what you were just saying, I’m just wondering in learning, and especially in the 20s for your age, how did you adjust yourself going into that type of an environment, having to understand how to present yourself as a woman, young woman, in this really heavy area? This is not just venture capitalism here. This is the bigger stuff than that.
Caroline Simmons:
Yeah, you’re right, Reischea. I mean, there’s still far too little women in the national security field, and there’s been a number of articles about that recently about the need to elevate more women. And it was definitely a challenge. I faced a number of moments and doubts early in my career there where I didn’t have high self-esteem and I doubted myself and it was definitely an intimidating environment to be in. And I think one thing that I found helped me succeed there was to put my head down, work really hard, take the opportunity to learn from the people around me and to learn from the secretary of Homeland Security, Janet Napolitano, she was this incredible strong woman leader of the department, and she helped bring a number of women up through the ranks, too, under her leadership.
So I think that was really helpful, but I would be lying if I said that I didn’t have moments of doubt and uncertainty being a young woman in my career at a department that was dominated by a number of men, and you’re right, Reischea, in a field that is typically dominated by a number of men. But I think just working hard, putting my head down and showing that I could produce the work that really helped me.
Julie Holton:
Let’s talk about how you got started down this track because it’s so interesting. I think even reflecting back, I’m only a couple years older than you, so it’s not like I’m way ahead in the age game here. But I remember thinking back on it in my 20s feeling like, why do people keep bringing up my age? I’m just here doing my thing. But I realize now that not a lot of people, let alone women know at a young age, the path they want to go through in life. And so I think that’s why we keep bringing up this age thing, because at various points in our journeys, or whether we’re 65 or 45 or 25, there are a lot of people who still don’t know and it’s okay, but don’t really know where they want to be or what success is going to look like for them. So I’d love to really hone in on your track and how you got started and how you’ve known with each career change you’ve made that you were doing the right thing for you and for your family?
Caroline Simmons:
I love that question because I think there’s so many points along the road where I wasn’t necessarily sure I was on the right track. And what I always say to young students, especially young girls, is don’t be afraid to fail along the way, because oftentimes when one door’s closed for you, another door opens up. And so I shared the example that when I first ran for student government in ninth grade, I lost my first election badly. And I thought, oh, I’ll never be in government or public service. And I was always so nervous about public speaking in school, but I think just because you fail the first time at something doesn’t mean you can’t still pursue that passion or that you can’t be good at it with practice and time. So I like to share that lesson. And then another time I failed is in college.
I became really passionate about international security and foreign affairs after the 911 attacks. And I wanted to study Arabic and ultimately become a CIA agent. It was around the time, those Matt Damon Bourne Identity movies had come out and I was obsessed….. You can probably remember those….
I was obsessed with him, but I took Arabic in college and it was one of my worst grades. It completely brought down my GPA. And I think we have so much pressure on us as women to be perfect and to be a perfectionist and to succeeded at everything. But oftentimes you learn the most in life through failing at things. And when you challenge yourself and take on things that you might not get that perfect A at, or you might not succeed at perfectly the first time, I think that’s often the time that you see the most growth. And I look at all the opportunities in my career where I failed, or I didn’t necessarily get something and it ultimately led to a better path or it helped me learn and grow and get stronger. And so I always try to share that message along the way.
Reischea Canidate-Kapasouris:
I so wish we could find another word for fail because you’re so right. It’s when you don’t succeed necessarily at that thing, or you don’t get to it the way you thought you would. It’s because you had to learn that, well, that wasn’t the way to do it, or, well, let me try it a different way. Because fail has that negative connotation. But bottom line, everybody who is successful says the same thing.
You learn more from when you don’t succeed than from when you do, because when you don’t succeed, then that teaches you that lesson of how to change it up, go a different direction. So I served on the Democratic City Committee for Stamford through the first couple of months of your term as mayor. And one of the things that you get to do as mayor, of course, is have… Obviously, set up your staff, however you want, which you’ve put in a lot of women, but also certain appointees for different commissions throughout the city that are mayoral appointees. Out of the gate, you send out these uber-qualified, diverse women for seats that are looking to be filled. I was around for the administration before you, we did not get those kind of candidates, or at least not the amount that you came, that came our way almost immediately. How important is it for you, Caroline, to foster that type of an environment that showcases the talent that simply is being an amazing woman?
Caroline Simmons:
It’s so important to me to lift up other women and to promote a more diverse cabinet and more diversity in all of our boards. I think our city is, obviously, we’re a representative democracy and our city government is supposed to look like the people that we serve. And we have an incredibly diverse city. One of our greatest assets in Stamford is, we have people that speak 65 different languages that come from all over the world. And so I want our government to be more responsive and to look like the wonderful city that we represent. So we’ve really made it a priority to get more diversity on our boards, to lift up more women, to lift up more women of color, to lift up more Latino women on our cabinet.
I’m so proud that we just hired. It’s actually just hit the press so I can announce it on the podcast. We just hired our city’s first diversity, equity, and inclusion officer; who’s this amazing woman named Carmen Hughes. Who’s going to work to really embed racial equity and inclusion across all of our city departments and our boards, and to really try to make meaningful change there.
I think so often we talk the talk as politicians about DEI and about diversity and equity and inclusion, but we really want to make significant progress in reducing the injustices that we see and making our city a more inclusive and equitable place. And I think that starts with getting people to serve in our government and in our boards that look like our community. And for anyone listening, that’s interested in serving in our boards, we would love to have you apply. We’re trying to get more young people, more diverse voices. So if you check out our website at stamfordct.gov, you could find openings for our boards and commissions. We would love to have you apply.
Reischea Canidate-Kapasouris:
You do need to be in Stamford, Connecticut though, just saying.
Caroline Simmons:
That’s true. That is true.
Audrea Fink:
I love that you’re this focus on diversity. I want to ask you a question, though, because when we talk about women being participatory and being part of the process, instead of just being the people who receive whatever the benefits or the activities of the government are. We really want that representation because we want to be understood. We want what our challenges are to be understood. We want what our needs are to be understood. You are a mother of three. And so right off the bat, for me, I think, oh, that’s amazing to have a woman understand in a government level, what I might go through.
Having said that, when you left for maternity leave, you only took one week off. That single week, stressed a lot of women out. And there’s been a lot of pushback, I think, with this idea of women and men, right? More parental leave being needed. And now we have this amazing woman in office and she took one week. And what does that say? What was the thought process and the reason behind that quick turnaround and how would you respond to someone who says, this is the thing that we worry about with having a man. How would you approach that subject?
Caroline Simmons:
Sure. And it was honestly such a hard, hard decision to come back that early. And it’s something I didn’t want to do. So I’ve been a strong champion for paid family leave and women being able to take 12 weeks. I think it’s so important for women and men and for parents to be able to have that time, to bond with their children, to be able to have that recovery. And it’s always something that I’ve wanted to promote for other women and will continue to promote. And I was hoping to be honest with all of you, to have been able to take more time than I was planning to, we did, after about a week, we did have a number of serious incidents that happened in this city. One was a partial collapse of a building, of a terrace in a building down in downtown Stamford.
Another was, there was a series of snowstorms as well as other public safety emergency-related issues that I decided fortunately we were still in Zoom world. It was during COVID. And so I was really fortunate to be able to resume my duties while being able to still stay at home and have that flexibility to be able to operate via Zoom, to be able to be accountable for these emergencies. But what I said to my team is, not all women and not all families have that. And I want to make sure that we’re fighting for more family-friendly policies for women who are frontline workers.
We look at all the women who served as nurses and emergency responders and frontline workers during COVID, who didn’t have that luxury. And so that’s something that I want to bring to this office as mayor; is to make our city more family friendly and to be able to fight for opportunities for families that don’t have that luxury of being able to Zoom from home with their kids and to have that support network in place. And so I will be honest. So it was really hard going back that early. And I want to still make sure that all women and families have the opportunity to have more time that they need and deserve for their recovery.
Julie Holton:
Of course, it was so hard. I mean, physically, mentally, all of it. And I think it’s really important in all fairness to say that men who are mayors, who are also fathers, don’t get the spotlight put on them in the way that you did with this.
And it’s one of those things that women navigate, whether they’re mayor or in politics or in any workplace setting where there’s that balance between having a new child, having a newborn, but also just parenthood, being a parent, being a mother balancing with the work requirements. Your job as mayor obviously has additional pressures that someone else may not have depending on their role in the workplace. Like you said, your city was under fire with multiple things happening that really needed the guidance of the city, the top city leader. So, but, it’s just so unfair that women especially are put in the spotlight and even called hypocritical when they don’t do, as they say. And the reality is we don’t even look at what men are doing, let alone criticizing them for it when it comes to the time they spend with their children. So that right there negates any negative opinion, in my opinion.
Reischea Canidate-Kapasouris:
What was it that another guest we had on had mentioned? Alicia Holt, and she was talking about men, the difference in men and women, and how they look at things. And someone will take something that a woman has done and put that across the entire, just swath that across the entire swath of women, and then have to rethink, I don’t know if we’re going to go down that road with that type of a hire again, or an African American person, a Latina, whatever. I’m not sure if we’re… They’ll put one thing that may have gone wrong or something, and that counts against the entire group. They have no trouble or problem whatsoever hiring 10 other white guys. And they’ve had plenty of issues with those same male people, but it doesn’t matter, but we’re going to go and get Billy again, even though Bobby was a mess and Tim was a mess. But Billy is going to be the one that’s going to work out. Isn’t it so interesting how that still just plays out no matter what the situation is?
Caroline Simmons:
It is so true, Reischea. I find that to be so true. It’s almost like a stereotype of this happened with one woman, and then you put it on the whole population as sort of like, an I told you, so that’s why we can’t have women in these roles. And what you were saying too, Julie, rings so true in terms of, they don’t ask those questions to men. And I mean, so many times on the campaign, I got that question, how are you going to do it? How are you going to manage it with three kids? And my husband who actually was a politician, ran for office when I was pregnant and he was running; he never got that question. How are you going to manage it? And same thing, I think when you bring your kids to events, you sort of can’t win either way.
When I would bring my kids, people would say, that’s inappropriate. You shouldn’t bring your kids. But then when the dad brings the kids, it’s like, oh, he’s such a good dad. That’s so cute. He’s got the kids with him. And then if you don’t bring the kids, it’s like, oh, you’re a bad mom. The kids are at home. So I think there’s so much judgment all around when it comes to women. And I think we just need to be more accepting and women need to do this too. We need to lift each other up and not pass on judgment and accept that everyone’s on their own journey and their own path. And to be supportive of whatever choices women are making.
Reischea Canidate-Kapasouris:
And we do do that. We tend to bite one another, as opposed to saying, Hey, you know what? She’s got to do it this way. And that’s how it’s working for her or finding ways that are working for her and whatever the situation is, as opposed to why is she… And we tend to do that. And I think part of that is also because we want to succeed and we want to move up and instead of seeing ourselves as a ladder for one another, we see each other more as competition over and over again, which is why you Julie, and Audrea started this podcast, which is very much in our intro. Stop that competitive nature and start lifting one another up. But it’s going to take time for us to properly do that as opposed to seeing that individual as, well, that’s my competition and I need to knock that person down. As opposed to saying, that might be my competition, but if we’re in competition, then we’re helping lift one another up.
Caroline Simmons:
I love that metaphor, lifting each other up the ladder. And it’s so true. Instead of competing with each other, when one moment does well, that’s great for all women, that lifts everyone up. And I think that’s such a great point, Reischea.
Reischea Canidate-Kapasouris:
Okay, so now you’ve got the husband, you’ve got these three boys. Let me ask you, what role does your husband need to play, or perhaps already does play in lifting up and recognizing a woman’s worth; to help teaching those lessons from their perspective as well, and to help forward that on? Because obviously we can’t do it all by ourselves. No one can, not a single human being can do it by themselves. But if you’re helping to teach at that young age, then you start changing that mentality before they get to the point where certain parts of the world are today.
Caroline Simmons:
Absolutely. I think I’m so grateful to my husband. He’s an absolute saint and I could not do this without him and my sisters and my mom and my mother-in-law. I mean, it really takes a village and I’m so grateful for the help that we have, because it would not be possible. And I think you’re right, it’s so important that we teach our kids the message that moms can be strong and be in powerful roles and have to work. I think of my sons, it still breaks my heart when they’ll cry, when I leave in the morning to go to work and they get so sad that I’m leaving them and I try to explain to them what I’m doing. I’m going to try to help people. And sometimes I’ll say I’m going to see the firefighters today and then they’re like, “I want to come.”
And so that’s maybe not the best thing to share with them, but I think just teaching our kids that we have our own lives too, and that it’s important to work and to contribute to the world. And I think, I hope my boys, will grow up with that mentality, that their mom can be strong and that it’s important to appreciate working parents and what they’re doing. And I try to teach my sons about what I’m doing in the community. And I hope that will resonate and that they’ll forgive me or someday appreciate the long hours and the times that I have to miss bath time.
Julie Holton:
Well, right. And that’s the reality of it too, is all kids everywhere would love for moms and dads to always stay home and never go to work and only get to play. And that’s just not the way the world works. So we have to teach them one day at a time. Caroline, this has been so good. It’s just so, so invigorating to hear you talking about just this real life balance of working and having your kids. Before we go, we are collecting advice from successful women in our communities and sharing it in our Think Tank of Three forum. So we have three rapid fire questions for you. Starting with number one, is there a lesson that you’ve recently learned that you wished you had learned earlier in your career?
Caroline Simmons:
Yes. I would say communicate, communicate, communicate. Everything is about communication. And I think of times that I failed or times that there has been challenges at work, it has always boiled down to communication. Same thing when it comes to marriage and kids. I just think it’s so important to overly communicate and for young women too, to make your voice heard on an issue you care about, it’s never too early to make a difference and to fix a problem in your community and to make your voice heard.
Audrea Fink:
From all the lessons you’ve learned over your impressive career, what would be one piece of advice you’d offer to another career woman?
Caroline Simmons:
I would say that it’s impossible to have it all and to be perfect at everything in any given moment. I mean, right now I am not a perfect wife, or a perfect mom, or a perfect mayor. But I think to wake up each morning and to strive to do your best in the things that you’re passionate about, to give all that you have, to try to bring positive energy, and even to try to make a difference in one person’s life every day. I think that’s all we can strive to do. And I think, as women to give ourselves that the house does not have to be perfectly clean and organized. I think to embrace those imperfections of every day and to not put too much pressure on ourselves and to try to bring that sense of humor is so important.
Reischea Canidate-Kapasouris:
Oh, I have embraced the messy house. I have just had to ‘let go and let God’. Again, another thing that I just don’t get along with is the house cleaning, and it’s like at some point. In today’s professional setting, what do you think the most important skill for a woman is?
Caroline Simmons:
I think the most important skill is to be compassionate and to have empathy. I think that is such a critical skill that women bring to the table. As mothers, as wives, as partners, as friends, as sisters, we bring that empathy to situations is so essential. And I think, I got a lot of criticism on the campaign; will she be tough enough or will she be able to get things done? And I think people don’t always necessarily see women as the tough, hard boss that’s going to be able to be effective. But I think there’s so many ways to be effective, and I’ve found so far that bringing compassion and empathy to meetings and to relationships in order to get things for our city and to get things done has been so effective.
And I think there’s all different styles to getting things done in a meeting. And I think I’ve found that bringing that empathy and compassion is one of the most effective ways you can get something achieved. And I think something we need more of in this world.
Audrea Fink:
I just want to take a moment to call out that while you took this amazing time for us today. Right behind you, is your kid talking to himself and having a good time. And I just love that. I love that. I love that there’s a balance. You can be both. It may not be perfect. It’s going to be perfect, but thank you for being a mom in addition to being a podcast guest that I just, I love that. And I just want to call it out as being a really amazing moment for me personally, on this podcast.
Reischea Canidate-Kapasouris:
It’s like you’re feeling my brain, Audrea, because I was literally thinking that exact same thing.
Audrea Fink:
Chills. I was like, yes, this is it.
Julie Holton:
Yes. Let’s normalize taking a fun day at the park and pausing to do a podcast, but not having to be perfectly put together to get on a Zoom; because we record on zoom, to get on a Zoom call. Uh-uh (negative) that’s not how we do it at Think Tank of Three. Just pause your day, a little podcast, get back to your day. Yes, this has been just so great. And I love too, that you’ve taken the time to talk with us. Mayor Simmons, you mentioned earlier the city’s website, what is the best way for our audience to connect with you if they want to connect with you further?
Caroline Simmons:
Yes. And thank you so much, Julie and Audrea, and Reischea. This has been so inspiring and empowering. Thank you for all you do to lift up women and I’ve so enjoyed this podcast, it’s been the highlight of my day and I’m glad the kids weren’t screaming too much. Thank you for being so understanding. So best way to reach me would be at my email, which is csimmons@stamfordct.gov. That’s csimmions@stamfordct.gov. I would love to hear from you or anyone listening on any feedback you have or questions or ideas you have on how we can improve our city.
Reischea Canidate-Kapasouris:
Caroline, thank you so much for joining us today. It has been an absolute pleasure. I always enjoy talking with you, spending time with you. And once again, just another phenomenal woman just doing her thing, being a woman.
Caroline Simmons:
Thank you all so much. What an amazing way to start the day. I wish I could do this every day. You three are amazing super women. And thank you so much for the podcast today and for the opportunity to connect with you.
Reischea Canidate-Kapasouris:
You’re so very welcome. And that will do it for this episode of Think Tank of Three.
Audrea Fink:
If you have topics you’d like us to cover or guests you’d like to hear from send us a message at thinktankofthree@gmail.com. Subscribe to the Think Tank of Three, wherever you listen to podcasts and connect with us online. We blog weekly at thinktankofthree.com.
Julie Holton:
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