Creating Confidence with Heather Monahan
Confidence Classic: The Truth About Confidence, Criticism, and Real Legacy with Dr. Wendy Osefo
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
Full Episode
Hey there or love it. People are going to say something. And that's why when I was thinking about going into the show, I said in my life, whether it's being a professor or being a commentator, I lead with authenticity. I'm always true to who I am. Like I never go in there. Like I know people, even in the political realm, they don't believe what they're saying.
They're saying it because they know it will get attention or because, you know, they're being a voice or mouthpiece for someone. Everything I say, I believe. And even in the classroom, everything I say, I believe. So I say that to say with shooting the show, I came into it with the same mindset.
So if you don't like what you see on the TV, I'm okay with that because it'll be different if I was faking or I was pretending to be somebody and I'll say to myself, oh man, I wish I was just my authentic self. Maybe they were like that. No, you get what you get. And so I'd rather be hated for who I am than love for who I'm not. So this is who I am. If you don't like it, move along.
Come on this journey with me. Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. I'm ready for my close-up. Hi, and welcome back. I'm so excited you're back here with me today. Thank you. Okay, so, oh my gosh, as if the hits just... Keep on coming around here. We've got a hurricane heading for Miami right now.
And I'm so sad to share with you that my longtime mentor and good friend, Bob, passed away yesterday. And I'll tell you, when you deal with so much sadness, as I know you are, right? We all are, whether it be from being in quarantine, just dealing with the pandemic, the news, losing a job, getting furloughed, panicking about what's happening to our economy and our world, the political situation.
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.
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