Building Mental Resilience While Building a Business

Talking about Self-Awareness and Anxiety (with Hello Monday’s Jessi Hempel)


MORRA AARONS-MELE: I’m Morra Aarons-Mele, and this is The Anxious Achiever. Each episode, we look at stories from business leaders who have dealt with anxiety, depression, or other mental health challenges, how they fell down, how they picked themselves up, and how they hope workplaces can change in the future.

I doubt that there is a person in the world who would disagree that running a business is stressful. I mean, you could be the world’s chillest person, but a few months into managing your own venture, I am willing to bet you might be losing some sleep. It’s part of the package, I think, when you run your own shop, no matter how small or how big it is. I mean, I have heard the same fears and anxieties spoken by the founders of Spanx and JetBlue, giant companies, for example, as I’ve heard from friends who run really small consulting firms, or catering companies, or small nonprofits. “Can I make payroll? Is this all going to fall apart like a house of cards? Are my competitors catching up to me? Am I the right person to be leading this venture?”

But I think the difference between those who make it work and those who fail is resilience, which is itself a form of courage and strength. So today, we’re going to discuss how to build your resilience muscles with Cheryl Contee. Cheryl is the award-winning CEO and co-founder of the firm Do Big Things, and before that, she was CEO of Fission Strategy. She’s also co-founder of the social marketing software Attentive.ly, which was the first tech startup with a Black female founder in history to be acquired by a NASDAQ-traded company. Before all that, Contee co-founded Jack and Jill Politics, where she wrote as Jill Tubman on the leading Black audience-targeted blog during the 2008 and 2012 election cycles with her co-founder, Baratunde Thurston, who was Jack. We’ll talk about that a little bit too.

We met in a very different era, I think, of both of our lives in politics in the early 2000s, but I want to talk for a minute about what it was like for you to be an online personality. I think it’s really related to the topic of resilience. I knew you in, I think, 2004, 2005, 2006, and I knew your blog, but I didn’t know you were your blog. I’m curious how being an anonymous, but quite famous, blogger helped you become an entrepreneur looking back. Did it inform your decision to say, “You know what? I can be an entrepreneur because I’ve gone through this crazy journey online”?

CHERYL CONTEE: That’s a really good question, Morra. I would say that a few things happened. Writing under a pseudonym or a nom de guerre and having that really explode in a way that none of us could have imagined … and most Black people who were talking about politics of that era, right, at like 2006 and 2008 were writing under a pseudonym just because no one had ever been that outspoken on the internet in the way that we were doing. America has a tendency to shoot at or hang outspoken Black people, so it seemed like a good idea at the time. But as it became more famous, I started to get the sense that, “Look, I’m going to get out at some point.”

MORRA AARONS-MELE: Mm-hmm.

CHERYL CONTEE: Right? I can either take control of this or let it happen to me. I mean, having that… talk about anxiety, having this basically hidden Batman/Catwoman role, in which I was being loud and taking on the Congressional Black Caucus and NAACP on the internet, and then by day, I was Morra’s Black friend like, “Yeah,” like that was… It was a little stressful, right?

MORRA AARONS-MELE: Well, not only that. You were working on K Street at that time, right? You were working in the establishment of Washington, D.C.

CHERYL CONTEE: Yeah. Absolutely, as I was taking on the establishment by night. So yeah, that was stressful. I will definitely say it did create in me a lot of resilience in terms of… We would get attacked. We would get hacked. It was stressful at times taking on… being an individual and taking on these big entities, powerful entities, with the community behind us. But what I will say is that being that anonymous blogger, and then coming forward, and blogging as myself, it gave me a lot of credibility, right, among prospective clients in that, look, I’m now one of the OG influencers online. You know how important internet influencers are, and I know intimately just how the internet has changed the power mapping among individuals versus organizations, and it provided me with a platform.

MORRA AARONS-MELE: So, you talk a lot about resiliency in the context of entrepreneurship. What do you mean? What do you mean by that? How is an entrepreneur resilient in a way that someone who may not run their own business isn’t or doesn’t need to be?

CHERYL CONTEE: Oh, you absolutely have to be resilient, especially if you’re running a tech startup. I mean, in my book, “Mechanical Bull: How You Can Achieve Startup Success,” part of the reason I named it “Mechanical Bull” is because it’s a wild ride. You’re really tested in terms of how long can you stay on that bucking bronco, that is, your business. Look, in America, 90% to 95% of startups fail in their first year. Of those who make it, 10% of those … 5 or 10% of those will fail in their third year.

MORRA AARONS-MELE: Yeah.

CHERYL CONTEE: Whether you like it or not, you’re going to have to figure out how to be resilient as your business does or does not succeed, and then what do you do next? How do you tell the story about what was successful and where things went awry, even if it wasn’t your fault? There are lots of reasons why a business might not survive its third year that have nothing to do with the hard work, and the ambition, and the great ideas, and the dynamism of its founders.

MORRA AARONS-MELE: Right, and that is true. Can you give me a specific example of a really resilient moment in your career as a now veteran startup entrepreneur?

CHERYL CONTEE: Oh, boy. Well, I will say we had a client way back that we just hadn’t quite properly vetted. As it turned out, we were starting to get feedback like, “Hey, if this is your client, you should know more about these people.” It turned out their motives for working with a group like us were disingenuous. We were pursuant of that. At the same time, we took a lot of heat from that professional community. But how we decided to approach it was just to stay true to our mission and say, “Look, we made a mistake. You should know that our values haven’t changed. We’re going to show that. We’re not going to talk about it. We’re going to show you.”

MORRA AARONS-MELE: So, you tell that now, and it sounds like you had a plan, you executed, but I can imagine that there was anxiety there. I know if it was me and that happened, I would think, “Oh my gosh, that’s it. I’m done. The company is done. We’re going down.” Did you have those feelings of anxiety and catastrophe at the time?

CHERYL CONTEE: Yes, girl. I was like, “We are in really big trouble.” I tell people now like, “Look, your reputation … There is nothing more precious than your reputation and your network.”

MORRA AARONS-MELE: Yeah.

CHERYL CONTEE: I wouldn’t have been able to launch my businesses without my network and would not have been able to keep them without that network because look, what also happened was while we may have lost a few clients, there were people who stepped forward who heard us talk about the fact that, “Look, we may have made a mistake here, but here’s who we are, and here’s who we’re going to continue to be, and what we want to do, and who we want to work with,” who came and said, “We believe in you, and we’re going to support you. We know that you could probably use this work, and we’re here for you.” If you have that supportive network and community, and you are that kind of person, like I know you are, Morra, where you’re helping other people along the way, when you need help, you’re going to find that come back to you 10X.

MORRA AARONS-MELE: Yeah, and you actually talk a lot about resilient communities. I want you to talk a little bit about why you’ve adopted the term “cognitive resilience.” I actually found this one. I was researching you, and you said, “Cognitive resilience is a clinical term used to describe the body’s ability to buffer itself from external trauma.” Why is that an important term not just in your life and your work but in your work as an organizer, as a progressive?

CHERYL CONTEE: Well, I actually got that from some folks who work in philosophy and in academia. That’s an academic concept, cognitive resilience. I think that we absolutely as Americans right now and even globally are in… We’re facing very difficult times. Even if things were going smoothly, we’re in a very volatile time with a lot of technical changes and innovation that are changing how we work, and how we live, and how we communicate and connect with our neighbors. So, having that cognitive resilience of like, “Okay. I’m intaking this information. I’m finding ways to process it, and I’m finding ways to be creative,” right, is really important.

MORRA AARONS-MELE: Mm-hmm, but protect myself from it. There’s got to be a level of protecting myself from its damaging effects as well.

CHERYL CONTEE: Absolutely. I have things that I do to keep myself more resilient and that I’ve tried to coach my team on, as well. Those include just relaxing. Okay? Part of cognitive ability…

MORRA AARONS-MELE: What? How? What?

CHERYL CONTEE: Look, I come from an African-American culture. I think that the other subcultures in America often are like… We often get accused of being lazy, right, which is the opposite. So much of America was built by Black people. Okay?

MORRA AARONS-MELE: Mm-hmm. Yes.

CHERYL CONTEE: Including the Capitol Building and the White House. So, we’re not lazy, but I would say that we… Part of how we as a culture develop cognitive resilience is to just try to stay relaxed, see the humor in a situation, and get your work done, but your work doesn’t define you.

MORRA AARONS-MELE: Mm-hmm. Mm-hmm.

CHERYL CONTEE: Right? Especially if you’re a slave, right? You would better believe that your work doesn’t define you. Right? So, there’s a lot to learn there. I think just like… Can you relax into this moment and accept what’s happening, and breathe, and find the best? Do your best and find your best in it. Can you keep things in perspective in general and find people… I have an executive coach and have had one for some time. We have had executive coaches for some of our execs just to say, “Hey, do you need to talk to somebody externally here to think big,” right, “about where you want to go next with your career, or how do you improve yourself,” right, “in facing a challenge that’s in front of you?” So, definitely a big believer in executive coaching and then wellness. Look. Meditating, right-

MORRA AARONS-MELE: Mm-hmm.

CHERYL CONTEE: Meditating, like it’s not… Sure, it might be a little bit of California voodoo. I’m here in Silicon Valley. Okay, that’s real. But you know what? Meditation is just hacking your brain.

MORRA AARONS-MELE: Mm-hmm.

CHERYL CONTEE: Right? It’s literally just… So, if you see it that way of like, “I need to hack my brain so that I can cultivate more cognitive resilience, like things pass… things happen in front of me or pass through me. I am not them. They are not me.” Right? I can Tai Chi, just let that itch go. Right? That takes practice.

MORRA AARONS-MELE: How do you as a leader of a startup with so many internal and external pressures reinforce that because it’s… We all know that we should meditate and do yoga. How does a leader actually make that part of her and her team’s day?

CHERYL CONTEE: You just do it. I mean, look, I schedule things. I schedule meditation. Right? It’s part of my calendar. If you’re like me and you are living and dying by your calendar, it’s like, “Okay. This is the half an hour where I meditate.”

MORRA AARONS-MELE: Right.

CHERYL CONTEE: Right? Or I’m starting my day…

MORRA AARONS-MELE: Don’t Slack me.

CHERYL CONTEE: Yeah. This is not the time, and I tell people on Slack like, “Hey, I’m now going to meditate.” A lot of people do meditation. I was actually just at… We were both at the NPR How I Built This Summit, and I asked a room full of startup founders, and investors, and other executives like, “How many of you meditate?” You know what, Morra? Almost all of them raised their hand.

MORRA AARONS-MELE: Yeah.

CHERYL CONTEE: Yet, I’m willing to bet… Yes, meditation is one of those secrets of success, okay, in this world.

MORRA AARONS-MELE: Yes.

CHERYL CONTEE: Okay? So, if you’re listening and you don’t have a meditation practice, let me tell you, you are not competitive, okay, because your competitor is meditating like a champ.

MORRA AARONS-MELE: Boy, I think that’s not the point of… To make meditation competitive is not the point, Cheryl.

CHERYL CONTEE: That’s not the point, but I’m just saying that if that’s the way, if that’s how I’m going to get you there, then just consider that your competitor probably has an active meditation practice. What I challenge them in the room and what I’m challenging you who are listening is don’t make meditation your dirty little secret.

MORRA AARONS-MELE: Yeah.

CHERYL CONTEE: Okay? If you are meditating and you know that it is making you more effective as a human being, and as a leader, and as an executive, it is incumbent upon you to model openly with your… because that’s how we normalize it.

MORRA AARONS-MELE: I want to talk about another side of this coin because I think, especially for women in business and for people of color, for people who don’t fit the “dominant” majority, there is a relationship between anger and anxiety. Right? I know often as a woman – and I’ve been told this by my therapist – what I experience as anxiety is really anger that I’m scared to feel.

CHERYL CONTEE: Wow, that’s deep. No, I think that makes a lot of sense. I mean, the way I think of it, Morra, I think of anxiety as the anticipation and the inner preparation for something bad or disappointing to happen, right-

MORRA AARONS-MELE: Mm-hmm.

CHERYL CONTEE: -which creates a lot of stress, right? For example, if you’re a person of color, and you’re driving around, and you see a police officer, that involuntarily is going to create anxiety and be like, “I don’t know what’s going to happen next.”

MORRA AARONS-MELE: Yes.

CHERYL CONTEE: So that’s different. That’s anxiety, but right, the anger of that is like, “Why should I have to feel that way?”

MORRA AARONS-MELE: Exactly.

CHERYL CONTEE: Right? Like, “Why should I have to be afraid of the people who are supposed to be protecting me?” I feel like anger is the knowledge that something bad has happened. Right? Dealing with that anger, dealing with the aftermath and the ramifications of when someone I know has been arrested by the cops. Right? Like, it’s happened.

MORRA AARONS-MELE: Yeah.

CHERYL CONTEE: I have a lot of feelings about that. I’m scared and angry. Right? Something bad has happened, so I do think you’re right that… I think there is a relationship between anxiety and anger, and I think they’re… At least for me, sometimes I feel angry that I have to be anxious, like I’m angry that I have to worry about whether or not someone is going to discriminate against me in this moment.

MORRA AARONS-MELE: Yeah. What do you tell… I mean, you have a team of… You have a very intentionally diverse team at Do Big Things. What do you tell them about having all these big feelings and working through them while still being productive, and getting their work done, and being present mentally at work? It’s hard, right?

CHERYL CONTEE: It’s not easy. Look. Just for those who are uninitiated, Do Big Things is a digital agency. We specialize in new narrative and new tech, the new era in which we all were living in for causes and campaigns. So, we work with organizations like Everytown for Gun Safety. We’ve worked with Greenpeace, Friends of the Earth, NAACP, all kinds of different types of organizations plus political campaigns. We’re working with great companies like Google and Etsy, NBCUniversal on stressful stuff like our project with NBCUniversal is called Erase the Hate, and it’s… Some on-air, but mostly on their online properties, trying to lead a conversation and manage a conversation online about tolerance. If you’re the community manager, the online community manager for that, you’re seeing stuff. Okay? You’re seeing some not necessarily tolerant stuff, and that’s stressful. This isn’t just selling soap, right?

MORRA AARONS-MELE: Yeah, yeah.

CHERYL CONTEE: I mean, this is stuff that could be really meaningful to people’s lives. I’m sure it’s very stressful. What I try to lead is the conversation of, “Let’s be honest about how we feel,” right, “Is this creating feelings for you? Do you need to take a break? Are you under stress? Do you need help?” Right? Keeping that bottled in and creating that safe structure where we at Do Big Things are a team. If there’s something going on, you may not feel able to talk about this in this open environment, but you should find someone to talk about this with, whether it’s internally or externally, because I know something just happened out there in the world that impacts how you feel about the work that we’re doing, period.

MORRA AARONS-MELE: So, what can an aspiring entrepreneur listening today … What is the number one thing they should do to start building resiliency muscles, right? They’ve got their idea, they’re early in their journey, and they are nervous, and anxious, and all the what-if’s. Can you help practice resiliency?

CHERYL CONTEE: Yes. I think you can help practice resiliency. Here’s what I would say. It’s like, look, anxiety is important to listen to. When I get nervous about something, instead of reacting to that nervousness and having it create a vicious cycle, say, “Oh, okay. I noticed that this is making me anxious. This is making me a little nervous. There’s something for me to pay attention to.” See it as information.

MORRA AARONS-MELE: Yeah.

CHERYL CONTEE: Take a step to the side of it and say, “Okay. This is interesting information. I should ask some more questions, or I should get a little more understanding before I move forward.” The other thing I would say is trust yourself. Sometimes, anxiety is you second guessing yourself, or comparing to other people, or just like, you’re reading the tea leaves in the most skewed way.

MORRA AARONS-MELE: Mm-hmm.

CHERYL CONTEE: Neuroscience tells us now that we make decisions not from our frontal cortex, not from the logical part of our brain, but from an older emotional part of our brain. How that mechanism actually works is that that part of your brain, which is closer to some of the animal brain, the middle of your brain, it takes in literally millions of inputs. Right? So, it’s always out there scanning. It takes in millions of inputs, and then it cranks it through a black box and makes some calculations, and the output of that is a gut feeling. It’s an instinct. It’s an inner knowing. Right? It’s your intuition. That is the smartest part of your brain trying to communicate to you.

We have been taught so much that you should ignore that. Your intuition is like some crazy female superstitious stuff. No. Okay? That’s old. That is old information. Okay? The new science tells us that that is the smartest part of you, and so if you really can trust yourself, meditation helps with this. Really start to listen internally to what you already know. Okay? The answers are already in you because your brain has been working behind the scenes to help you figure this out. If you can cut through… learn to cut through the noise of the anxiety or use it as like, “Oh. Ping. There’s something for me to pay attention to. What do I already know? How do I sink back into myself?” That, the answer is already there of what to do. You know what to do.

MORRA AARONS-MELE: Cheryl Contee, thank you so much.

CHERYL CONTEE: Thank you. It’s a pleasure to be here.

MORRA AARONS-MELE: An award-winning bilingual journalist, spokesperson, TV personality, and internationally recognized parenting author, our guest, Jeannette Kaplun, has over 20 years of experience on TV, radio, and the internet. In 1999, she co-founded Todobebé, where she was chief content officer for 13 years. She also co-hosted two Emmy-nominated Spanish-language television shows on parenting for Univision and for Telemundo. Now, Jeannette is CEO of Hispana Global, which she launched in 2012, and it’s a bilingual platform for Hispanic women where she shares tips about life, parenting, technology, travel. She has a lot of good advice on something that I have frankly avoided talking about this season. Although, I’m really feeling it today, which is parenting guilt as an ambitious achiever who has anxiety around, “Do I spend enough time with my children?” So, we dive into that, and we talk about the illusion of control when you are running a business.

So, when did you first realize, “I have anxiety, and I bring it to work”?

JEANNETTE KAPLUN: Ooh, I actually did not realize for the longest time that I had anxiety. I thought as a child and as a teen that I had butterflies in my stomach, that I used to get very nervous, or sometimes I would get stomach aches. I thought that was actually normal. When I was in my early 20s was when I really realized for the first time that that was not normal… that a lot of people had it, but it’s not supposed to be there. So, it’s weird to understand as a teen and then a young woman that so many things that you thought on a day-to-day basis were part of you, are part of you, but that there’s different ways of dealing with that and that it has a name.

MORRA AARONS-MELE: So, you say butterflies in your stomach, like what… Tell us what that really felt like because that’s a sweet name for something that may not have been sweet.

JEANNETTE KAPLUN: Well, it’s an elegant way of saying sometimes I would get stomach cramps. I would get nausea.

MORRA AARONS-MELE: Yeah.

JEANNETTE KAPLUN: Really go into a lot of details. If I had a really big test, I would get very, very anxious. I would perform really well until, of course … if you are not handling it well, sometimes you become paralyzed by anxiety, and that’s when the stomach cramps became really bad. I even had to run to the bathroom when I was taking one of the standardized tests in my junior year. So, that was not fun because I was not allowed back into the testing room.

MORRA AARONS-MELE: Oh my gosh. Of course.

JEANNETTE KAPLUN: Yeah.

MORRA AARONS-MELE: They thought you probably cheated or something, right?

JEANNETTE KAPLUN: Yeah, but there were no cell phones back then.

MORRA AARONS-MELE: So, I want to fast-forward to the moment when you were in your 20s, I think, when you co-founded a media company, took on investors, the whole nine. Was this something that was a part of your vision as you emerged into a professional? Did you say, “I want to help start a media company. I want to be this media mogul?” Was that all part of your plan?

JEANNETTE KAPLUN: If I’m really honest with you, no.

MORRA AARONS-MELE: Oh, okay.

JEANNETTE KAPLUN: I was an accidental entrepreneur the first time. I really thought that I was helping out my husband at the time. When we were creating this company, I thought I was really helping him until he raised enough capital to be able to hire somebody else, but I fell in love with online content creation, and the internet, and community building. So, that’s when I realized, “Hey, this can really be built. This is something that I can be really active in, and I love it” because I always thought as a journalist… I studied journalism in college. I really thought that I would always be employed by somebody else. My aspiration was to be Editor-in-chief or Director of News, but I never envisioned myself as creating a media company from the ground up.

MORRA AARONS-MELE: I would imagine when you were starting the company that you both, you felt free. Right? You’re doing your own thing. You’re building this company. Was there a transition or a size that it got to where you went from feeling free to feeling… and in-control to feeling, “Oh my gosh, now I’m losing control because I don’t know what I’m doing?” Talk us through the journey of control in the business because I know that’s a lot of… That’s a motivating factor for a lot of entrepreneurs.

JEANNETTE KAPLUN: Well, when you create a business, yes, you have the illusion of control. So, anything that happens is your responsibility, either good or bad, but at least you’re controlling it. But with each round of investment, and this is something that I feel is not discussed enough, you start losing control. You get diluted, and other people come on board. They might not have the same vision. They might not have the same goals or share your mission. That becomes very difficult for an entrepreneur to know when to let go, and what’s normal, and what’s not because you’re not going to be able to grow if you are overseeing everything and you are micromanaging everybody.

As part of growth, you need to learn to delegate. But the problem with losing control is when you are partnering up with people that might not share that vision, or investors sometimes change, and that can… Sorry. It’s very difficult for me to articulate it in words, that sensation of not being able to share that vision anymore. Once you created a company and you have different visions of what you’re doing and why you’re doing it, that I think is a moment in which you might feel that things have gotten out of control and you might want to retake control, but maybe it’s not possible anymore.

MORRA AARONS-MELE: Did that happen to you?

JEANNETTE KAPLUN: Yes, and I think that’s why I have such a hard time articulating it because in many ways, even though it’s been seven years, I’m still processing that shift and that moment in which I realized that I needed to take a different direction and that I needed to close a chapter in my life to start another one, and to write actually another book in my life.

MORRA AARONS-MELE: How did your anxiety come into play during the phases of starting a business, building it, and then as you described, realizing, “Oh, dear. I have to leave. I have to start a new chapter”?

JEANNETTE KAPLUN: Well, anxiety can play a positive role and a negative role. So, when you’re building a company, it gives you adrenaline. Right? That anxiety makes you hyper-alert. It makes you think of all the little details, everything that could go wrong, so that is actually really good because that way, you can stand for different scenarios. The problem with anxiety is that it’s associated so closely with impostor syndrome, and you feel that you don’t know anything that you’re doing, and you start doubting yourself.

If you start asking too many people for advice, then you get very confused, and you can actually become very scattered, and that’s never good when you’re building a business. You need to be hyper-focused; you need to know why you’re doing things, and you need to trust your vision. Sometimes when you’re dealing with anxiety, the problem is that you start second guessing every single step that you’re taking, and that can paralyze you. The reality is that as an entrepreneur, the worst thing that can happen to you is to stop moving. You always need to be moving. Either you’re falling, and then you get up, and then you learn from that mistake, or you keep moving, and you keep moving towards that goal that you have.

If you become paralyzed by anxiety, by fear, by fear of failure, you cannot grow that way, and you won’t be able to grow your business, and it becomes this self-fulfilling prophecy in which you start spiraling into a never-ending cycle of, “Oh, I know I couldn’t do this. Oh my goodness, this is failing. What am I going to do? What’s the worst thing that can happen? Oh, it’s happening.” It’s horrible. If you don’t take care of your health, and that includes mental health and physical health, then it becomes very easy to lose control of your company, what you’re building, and to feel like a failure in many ways as a person and to your family as well, if you have one.

MORRA AARONS-MELE: You just brought something up that no one has ever brought up actually on the show certainly, and I love it, and I’d love to ask your advice, which is that sense of, and I think a lot of us can relate to it when… You don’t necessarily even have to be an entrepreneur. You’ve built something. You’re driving something, whether it’s a project or your company, and the impostor syndrome sneaks in, and the doubt sneaks in, and you get all that advice, and you lose your way a little bit. Do you have any advice for re-centering and checking back in with your gut, your “mother wit” I always call it, your instinct?

JEANNETTE KAPLUN: Well, there’s different things that are helping me deal with those sensations. Right? The first thing is that I’ve learned to recognize the symptoms of when anxiety is rearing its ugly head and trying to gain control over my mind and whatever I’m feeling at the moment. So, that’s the first thing that you need to understand, how you work, how your mind works. So that way, when anxiety is really getting out of hand, you talk yourself down. Breathing exercises help me tremendously. Taking a pause, resetting, and even writing down what I’m feeling and what I need to do and establishing priorities because the problem is that it’s very easy to become overwhelmed. There’s so many things, so many responsibilities that we have to deal with on a day-to-day basis, on an hourly basis, on a minute-by-minute basis that it’s so easy to lose track of what’s really important. If you have a hundred priorities every single day, trust me, that means that you have a problem because not everything can be urgent. Not everything can be an emergency.

MORRA AARONS-MELE: That’s right. Something interesting also is … I think that once you start to find success, a lot of people in your life have a lot of opinions. I mean, this is so true for me. The more success you have, the more impostor syndrome actually might creep in, which feels counterintuitive, but I think that can be true for some of us. Then, you solicit advice and you start to doubt yourself while you’re actually becoming more successful, and so, it’s really hard to take a step back and say, “Wait a minute. I got myself here in the first place. I do know what to do.”

JEANNETTE KAPLUN: The more you know, the less you know, right, because you’re more aware of everything that you’re lacking. So impostor syndrome can totally, totally overtake all of your other emotions, and you feel that, “Oh my goodness, everybody is going to realize that I have absolutely no idea about what I’m doing, so I’m going to trust other people who seem to be the experts.” Right? But there’s a reason why you’ve achieved what you’ve achieved. There’s a reason why you’re doing it and connecting with people in a way that others are not. So, you have to remember that, even if it’s just reading one comment from a customer, a client, a community member, or, in my case sometimes, a reader. Go back to what you know, what you have done. The effect that you’re having on other people might help you center yourself and realize, “You know what? I need to go with my gut.”

MORRA AARONS-MELE: That’s right. I want to talk about your shift because you went from an uncomfortable period, exiting out of your first successful business to I think a much more intentional plan for your second business. Talk us through what it felt like when you exited Todobebé and how you picked up pieces and realized that maybe a different kind of business was the right step next.

JEANNETTE KAPLUN: Well, walking away from Todobebé was extremely difficult for me, but I realized what I wanted to do. What I wanted to do with Hispana Global, which is the company that I founded in 2012 was build something that I could control, that could help others but that I could control. So, I designed the logo myself. I programmed everything into WordPress. I designed my blog. I started creating all the social media handles, designed the style manual, interviewed different freelancers, and that way, I was able to not only understand every step of the process but also feel that I could control the company that I was building. I really felt the need to do that because I was not feeling that at the end of my tenure at my previous company.

So, for me, it was taking back my story, taking back my voice, taking back my power, and figuring out how to use it in a positive way and also make a living out of it. That’s how I built Hispana Global, which I absolutely love, but I kept it small on purpose. My goal has never been to achieve multimedia success in 10 different languages and to sell it to one of the big conglomerates. That’s not my exit strategy. I wanted to build a company that I loved and that the people who would come on board to work with me would also believe in that vision.

MORRA AARONS-MELE: Along the way, have you had people, even from your past business life, coming and saying, “Come on, Jeannette. Let’s scale this. Let’s do this,” and is it ever tempting?

JEANNETTE KAPLUN: It’s very tempting. I’m not going to lie. Of course, you could scale much more. Maybe help even more people, right, by being a bigger company, and that’s when it becomes very sexy to try to lose my focus and say, “You know what? Let’s grow it. Let’s sell.” Then, I remember what I felt seven years ago, and why I built this company, and why I designed it. I created it very purposefully in a way that I could manage it and also be present for my kids.

MORRA AARONS-MELE: Yeah.

JEANNETTE KAPLUN: Then, I’m like, “You know what? It’s very tempting. Let’s talk in five more years. Now is not the moment.”

MORRA AARONS-MELE: Well, I think you and me both share a sort of tension, right, in that we are mothers first, but we are also serious professionals. We also have our hands in lots of different creative pots, and we write, and we travel. I mean, I’m sure you have those moments. I actually have to admit that I was at the airport yesterday and realized that I had forgotten to buy a ticket, so.

JEANNETTE KAPLUN: That could totally happen to me.

MORRA AARONS-MELE: But the sort of managing it all and keeping control, it gets you. It gets you.

JEANNETTE KAPLUN: Yes, and sometimes balls fall to the floor. It’s like you’re trying to keep all the balls up in the air, but one is going to fall.

MORRA AARONS-MELE: I’m going to ask you a question that I haven’t addressed all season, but I think with you and me, we can address it, which is for me … a lot of my guilt around not being there as much for my kids sometimes can really make me anxious. So, I’ll be on a trip, and I will think of something I’m missing, or I’ll get a call from school, or my husband will tell me something rough that happened at school, and it will send me into waves of anxiety. I think that that anxiety might be rooted in guilt, in mom guilt. Does this happen to you? How do you handle it? Do you have any words?

JEANNETTE KAPLUN: It happened to me, but I realized that guilt is useless. It’s one of those emotions that really does not help with anything in your life. So, I found a way around it. I found that if I could make peace with doing my best and trying my best, then I needed to let go of the guilt. I can’t feel guilty for doing my best. I can feel guilty when I’m not trying my best. So, if I’m trying my best to be as present as I can be with the resources that I have, with the time that I have on my hands, then you know what? That’s okay. It means that sometimes I will miss out on important things. I haven’t told this to you before. I missed my son’s first steps because I was working. I was taping a show.

MORRA AARONS-MELE: Me too.

JEANNETTE KAPLUN: So, I missed that, right? I was in tears once I realized that, and it was my first child. So, it was pretty intense, that moment. I felt extremely guilty about it, but you know what? I was making a living. I was working hard for what I dreamed about, and it was fine. Once I came back home, I saw him taking another few steps. They weren’t the first ones, but… You are going to be missing on a few things, but the reality is that we are not going to be there for our kids 24/7. Our goal as parents is to prepare them to actually leave us, to be independent of us.

So, there’s so much that our children are learning by us working outside of the home, but I think we also need to be very, very cognizant of that, that it’s not all bad. We need to take a break from the narrative of all these responsibilities and the effect that taking on these responsibilities outside of the home … what effect it’s causing on our kids. I think we need to really understand that we are doing the best that we can. Sometimes, we’ll achieve what we need to achieve. Other times, we’ll fail, and we’ll learn to do better the next time.

MORRA AARONS-MELE: Ha.

JEANNETTE KAPLUN: Deep breaths. I told you. Breathing exercises work.

MORRA AARONS-MELE: Well, my dear, Jeannette Kaplun, thank you so much.

JEANNETTE KAPLUN: Thank you for having me here.

MORRA AARONS-MELE: That’s it for this week’s show. If you like what you’ve heard, be sure to subscribe and submit a review in Apple Podcasts or wherever you get your shows. If you have an idea for the show or want to tell us your story, drop me a note at anxiousachiever@gmail.com, or you can tweet me @morraam. That’s M-O-R-R-A-A-M. Special thanks to the team at Harvard Business Review, my producer Mary Dooe, the team at Podcast Garage, and all of our guests for telling us their stories from the heart. From the HBR Presents Network, I’m Morra Aarons-Mele, and this is The Anxious Achiever.



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