Creating Confidence with Heather Monahan
Confidence Classic: The Truth About Confidence, Criticism, and Real Legacy with Dr. Wendy Osefo
Tue, 03 Jun 2025
This episode is deeply personal. I open up about the recent passing of my longtime mentor and friend, Bob, and what he taught me about legacy, leadership, and living with intention. I’m also joined by TV personality, educator, commentator, and Real Housewife Dr. Wendy Osefo. She shares how she navigates public criticism, imposter syndrome, and the pressure of high visibility. We dive into what it means to be confident under scrutiny, how to reframe insecurity as part of your growth stage, and why being authentic will always outweigh being liked. Tune in and own your confidence. In This Episode, You Will Learn The mentorship that changed the course of my career. How to own your identity and shake off imposter syndrome. Why every confident woman still has insecure moments. How to have conversations across political divides. What balance really looks like as a working mom. Tips to manage decisions, set priorities, and say “no” without guilt. Resources + Links Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553! Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/ Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn Dr. Wendy Osefo on Instagram & Twitter
Chapter 1: What mentorship shaped Heather's career?
There's so much going on and having people close to you that you lose during this time. It's just... It's crushing. As you know, we lost my son's dog two weeks ago and then losing Bob yesterday. It's just, oh, I lost it. So I wanted to share what I learned from him. I think it's really important. And he's the only guy that ever taught me about this.
So I want to teach it to you because I want his legacy to go on beyond him being here. So I got into the radio business. Oh my gosh, I was so young. Maybe I was 23. Anyhow, I ended up moving to a publicly traded company, became the VP of sales and EBP CRO.
OK, during that time, I was back and forth to New York a lot, working with one of our vendors, our partners out there, which was our national rep firm. And at the time, he happened to be the president of one of the divisions. So he was very, very high up, much more senior than me. And he represented essentially the industry. I represented one company.
But for whatever reason, he was always kind to me. He was really into data and research. And I didn't know much about it. So I was super interested. So I would always ask him questions. And of course, we know people love when we're interested in them and their work. So he would take me into his office and share, you know, presentations with me and data and teach me.
And it was so nice, so generous with his time. And so we built a friendship and a camaraderie years ago, more than a decade ago, probably 15 years ago. And over the years, we would stay in touch, talk on the phone, text, email, whatever. And then when I was in New York, I'd always stop by and see him. And then the CEO of that company died. And the new CEO wanted him out.
He didn't want to work for him. It was a complete disaster and Bob left. Bob found himself in transition, which I know a lot about. We all know a lot about transition these days. So he called me and said, Hey, what do you think about me being your consultant? Which I was super excited for. Number one, I'll take any help I can get. Number two, I already love this guy.
He was so helpful to me and so different from me. So I thought it would be a great compliment. So I brought him on as our consultant. Eventually, I ended up hiring him as my right hand. When I became CRO, I promoted him to VP of sales. So a little weird, right? He's 20 something years older than me, tons of experience. And some people thought that was odd, but I trusted him. I really liked him.
And I saw value in him that could add value to the team. So we worked together and things were good. But whenever we would spend time alone together, I would want to get into... the specifics of revenue generation, what's going on with losing clients, what's happening with different categories of business, all the normal conversations you would have around revenue.
And he would always change the conversation to two things, legacy and footprints in the sand. And I remember when he first did this with me and I would think so weird what he talks about. Right. I thought it was so strange and I didn't really understand. I would appease him and listen to whatever he had to say.
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Chapter 2: How can you overcome imposter syndrome?
to be more of a mentor, to be more of an inspiration, to work harder because this man was the hardest working person in the world. And that's all. That's what I had to say. But please answer that question for me. What is your legacy? And if you don't have one yet, if you haven't thought about it yet, Bob's challenging you too. Bob wants you to leave the footprints.
And so do I. We'll be right back.
Meet a different guest each week.
Hi, and welcome back. I'm so excited for you to meet my guest today, Dr. Wendy, who's an award-winning researcher. Dr. Wendy is a Nigerian-American television personality and progressive political commentator. She's a contributor to The Hill, founder and CEO of the 1954 Equity Project, and professor of education at at the Johns Hopkins University. Oh my gosh.
Chapter 3: Why do even confident women experience insecurity?
You're also, you've got a show on Radio 1. You've got a BA in political science from Temple. I mean, you've got a PhD in public affairs. Your bio is probably one of the most impressive of anyone that I've had on the show. And I'm blown away. So thank you for making time and being here today with us. Oh, thank you so much for having me. So I wanted to start with...
I met with Bravo a couple of years ago about doing a show with them and I ended up walking away and we never made a deal. One of the reasons why, and I'm so curious about this for you, was I was so concerned with building credibility in life, you know, being a mother, reaching a level of quote unquote status or, you
and then losing it as a result of immersing yourself in something that some people might think would chip away at everything that you've built. Did you have thoughts like that when you considered this?
I did think of the negative connotations that naturally come with reality shows and what that can imply. But the truth of the matter is you have to be authentic to yourself. Those shows cannot define you. You actually have the ability to define those shows.
And I think it's really interesting because a lot of people have said to me, I think that just having you on the show, in a sense, is elevating the franchise, right? Who I am and what I am is something that can never be taken away from me.
Whether you see a camera on me as I'm hanging out with my girlfriends and, you know, we're having a few drinks and you hear me say something witty or smart, that doesn't negate the fact that I'm constantly interacting in these streets marching for Black lives. It doesn't change the fact that I'm speaking truth to power when it comes to politics.
It doesn't change the fact that I'm the first Black woman to receive my PhD in my department. Those things can never be taken away from me. It's sort of the argument as women that we face that is often said, you're beautiful, but you should dress differently so people can take you seriously. If the way you dress can take away from your brains, then that doesn't make any sense.
So that's what I look at it as. I could be completely wrong, but who I am and what I've done can never be stripped away because of social choices I make with my girlfriends. No. And I don't do anything crazy. I'm really not, you know, there's some crazy things, but I don't do anything crazy. So you just get to see my fun side.
Well, I think that's a great analogy and an excellent point that no one can strip you of your accomplishments, your experiences and who you are. And as long as you know who that is, you're fine with whatever else happens outside of you. And to me, that really sounds like confidence. Would you describe yourself as being confident? I think I'm confident.
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Chapter 4: What does authentic engagement in politics look like?
My closest friend in the political sphere is actually someone who sits on the different side of the aisle from me. And we learn so much from each other. And I say that to say, I think that people make politics a nasty word, but it's really not. Like, I learned so much from other people. And I just wish that we would remove all of the, you know, just the cattiness that comes with it.
Yeah.
It's a good one to hear because it definitely isn't the norm that I see. And I was around a few friends the other day for a socially distanced birthday party. And one woman brought up Black Lives Matter and specifically the riots. And immediately I could feel my body shrink back. I didn't even want to engage in the discussion for fear of...
For fear that I would say the wrong thing, fear that she'd get angry, fear that I didn't do enough and I'd be called out. And there's this sense that you, back to politics as well, that if you engage in the conversation and this goes sideways, everyone's going to be pissed off and it's going to end in an argument.
And I've seen it unfold so many times that way that it's almost, you know, a learned behavior now that, oh, don't get into that conversation versus someone, if you know going in, someone like you is open to, that's your opinion and that's your right. And, you know, I'm happy for you that you have that curious mind and maybe we can see some middle ground.
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Chapter 5: How can working moms find balance?
So how do we get people to stop arguing or how do you detract from the argument when people start it?
Well, my first question to people, if I find that they sit on the same side as me or they sit on a different aisle as me, my first question is why? Why do you believe that? Because sometimes people don't know why they believe or they vote for a certain political party. They just say, oh, I'm this. I'm a Republican. I'm a Democrat. Mm-hmm. And I challenge people all the time and I say, why?
And it's just a simple question, but it leads to a conversation. It'll say, you know, I was raised in a blue collar town and, you know, my blue collar town, this happened or this president gave a similar, like there's always a story. And if there's not a story, it makes people start to think, okay, why do I believe this political view? So I always start with why. I am an educator at heart.
That's what I am. I'm a professor. So I come to people at the very root of every issue and we build upon. I think the thing is when people say Black Lives Matter, you may already think, all right, what do I associate Black Lives Matter with? And so because you've said that, I know the type of person you are.
Or if someone says, I'm a Trump supporter, someone may say, okay, because you're a Trump supporter, I already know who you are and what you think. No. just simply take things to the basics and say, okay, you're Trump supportive. Cool. Why? Tell me why. And that throws a lot of people off guard because they think you're going to attack them.
If you say Black Lives Matter, you know, some people may be like, why do you don't think all lives matter? No, just say, oh, Black Lives Matter. Oh, okay. Why? educate me, you know? And when you start having conversations like that and taking out the antagonistic nature of it, it's simple. It's like, okay, tell me why. Oh, okay. That's why. Well, let me tell you why I believe what I believe.
And then they're like, uh, no one has ever told me that no one has ever talked to me like this is usually, you know, banter and you're stupid. You're this, you're that. And we don't need all of that. Like, tell me why. And I'll tell you why we can move forward and then have a glass of wine. I like that approach.
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Chapter 6: What is the importance of legacy?
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Chapter 7: How do you manage criticism in high visibility roles?
Turn your business idea into with Shopify on your side. Sign up for your $1 per month trial and start selling today at Shopify.com slash Monaghan. Shopify.com slash Monaghan. Shopify.com slash Monaghan. Around the topic of Black Lives Matter, myself specifically, and I know for other people as well, didn't know what it meant. So when it first... And I know it's been out for years.
However, I was ignorant to it. I wasn't educated on it. I didn't know. And so when... these conversations became massive in the past few months, at first I was thinking, well, that doesn't sound very nice because why wouldn't everybody matter? And I definitely thought that. And as I learned more, I've learned a lot. And as for all the good information you can get out there,
Sometimes there's really bad conspiracy theories, which I'm sure you hear many, especially this year with everything that's going on. And so it's trying to discern what is actually real, legitimate, factual information or quote unquote fake news and just conspiracy theory. That's been challenging, I think, for a lot of people. Absolutely.
I agree with that. And I think that, you know, if nothing else, I've had a few friends who have said that this year they've just educated themselves and they've learned more about people, about organizations. And I just think that that's really important. So, you know, when you when people are saying Black Lives Matter, it's not because, you know, white lives don't matter or anything.
you know, the lives of other people don't matter. Just simply saying we feel as though right now black lives are under attack. I cannot remember in my mind when I have seen a police officer kill a white man on tape. I cannot, I cannot, like I can't. But if you ask me, have you seen a police officer kill a black guy on tape? I could say, yes. I could literally say Philando Castile.
I could say George Floyd. I could say Rashad Brooks. I can name these people's names. And so I just think it's important for us to have these conversations, not because white lives don't matter. We're just saying that black lives are currently under attack and that's really what it is. And, you know, I have these conversations with my friends. You know, I was saying this the other day.
My son was invited over to one of his classmates, you know, houses. Everybody's in quarantine. Let's get together. And the mom said, you know, you guys should come over. Just got him a new, you know, water gun and all this other stuff. And I had to tell my child that he couldn't go and he didn't know why. And I said, because I don't want you playing with a gun. My sons, they're seven and five.
I have never bought them a toy gun. That may seem foreign to people, but that's because you have incidents like Tamir Rice. There was a 12 year old black boy who police pulled up that he was playing with a toy gun. They thought it was a real gun. Before they even looked at him, they killed him. He was 12. He wasn't doing anything. He was just playing. And that was it.
My sons will never have the privilege to play with a toy gun. Like that whole story of, you know, the Christmas story with the boy. His mom said, you'll shoot your eye out. Yeah, that's not relatable to my family because no one in my family that I can know of great, great has ever owned a gun. And the only person who did was my grandfather because he was a police officer.
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Chapter 8: What are effective strategies for political conversations?
But I just feel like I always run myself into the ground trying to make everyone else happy that I realized in order for me, Wendy, to be okay, I have to be okay letting go of some responsibilities and not being super mom sometimes.
Oh my gosh. I remember I was the same way with breastfeeding and feeling like it was my obligation and that pressure and the craziness. Oh, I feel you on that one. So I'm so glad your year is up.
over i am so like no if i hear another breast pump machine again i will kick it down the freaking road i hate it i can't do it anymore it's not a good sound if everyone listening has not heard it i'm not advocating for it it is brutal and if you were the person that was ever sitting next to me on an airplane
absolutely oh my god that wasn't good all right so tell me how I know a lot of people struggle with committing to something this is the example you just gave your son has a big project coming up he needs your help you had laid out a number of different shows that you were committed to doing and now you've got to go back to them and tell them I can't do this how do you approach that conversation
Oh, that's a great one. How do I approach that conversation? Well, all honesty, I always try to have a middle person. I'm a scapegoat type of person. Like, listen, I can't do it. And so I'll have, you know, my publicist or someone like reach out and be like, oh, something came up. It's not necessarily good, but... I'm a stickler for calendars. So I try to avoid those conversations.
Like when the school gives out the calendar for the year, everything is in my calendar. So I give myself 24 hours before, 24 hours after. Because if this is the date for the spring concert, that means we're going to have to practice. We're going to have a wardrobe, you know, make sure the wardrobe works. So if the spring concert is on a Wednesday, then I check out Monday.
So Tuesday, Wednesday and Thursday is all, you know, for me. So it's, it's always about managing and my husband and I, we sync our calendars. He's super busy as well. He's an attorney. So he has a million things going on. So we always try to, one of us is always present. We try for both of us to be present, but we always have one of us present. Um, And it's worked so far.
So fingers crossed that it continues to work.
Well, I am impressed because you guys definitely have a full plate. What kind of advice do you have for other working parents knowing that there's a very high probability that we're going to be teaching our kids at home yet again starting this fall? And as an educator, is there any advice that you can give us? If you can...
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