#114: How You Know It’s Time To Bet On Yourself & Take The LEAP with Heather!
4 Nov 2025 · 20 min
Heather reflects on being fired and why that moment taught her to bet on herself. She's hit speaking milestones like her first Google keynote and now declines unpaid speaking gigs, arguing creators need to value their time and stop apologizing for it.
Chapters
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. Welcome back.
I'm so excited you're here with me. What do you think about the new two episodes a week? I want to hear from you. Definitely want to know if you like this new setup. I hope you do. I'm doing it for you. Okay. So interesting. This week I had my second in person board of directors meeting in Naples for HealthLinked. And I'll tell you a few different things. One is that things are changing so fast right now. So, for example, I live in Miami, but my board of directors meeting is in Naples. Because HealthLinked is headquartered in Naples and Naples, basically there is no coronavirus at all. No one wears a mask. You don't need masks. I'm vaccinated, but. And again, no judgment zone if you are or if you're not. Totally your call. But it was so surreal that I was there for a couple of days and literally driving just a couple of hours away. It was a completely different experience and kind of surprising. I adapted to it really quick. So quick that I was driving home last night from Naples and I forgot to even have a mask out when I got back to my apartment building in Miami where I did need it, and I just forgot about it. I just jumped out of my car. So literally within 48 hours, I had completely adapted to this idea that coronavirus is gone so crazy. So depending on where you're going, things are very different. I also read that Walmart announced, no longer do you need to wear masks in Walmart as long as you're vaccinated, which is a huge deal. That's a massive U.S. employer. Right. So things are moving quickly. It's funny because a year ago right now, I would not even be able to believe that, you know, this would be happening as we were all still on lockdown a year ago. Just. It's so crazy. The past year is so crazy. Our lives are crazy. Okay, so back to being surreal for me. I used to work, or I worked for a company that was headquartered in Naples for 14 years. I actually lived in Naples a long, long time ago when I first started working for them. But what's bizarre now is that when I go over for our board meetings and we do a dinner as well, and you know, just going over to Naples now for Health Linked is so bizar. All the companies in the world. I was hired by A company that's headquartered the exact same place the old company I used to work for was headquartered. A little surreal, and I'm not going to lie, it's always a little awkward when I arrive. Well, it's only been my second time, right? So having gone there for 14 years for this company that ended up firing me and now going there for this new company that appreciates me, supports me, encourages me, is so grateful I'm on the board. You know, it's so bizarre. And for me, experiencing this, it's just. There's no words. I definitely feel a little emotional when I roll up to Naples, you know, because your memory just triggers immediately and you start thinking back to, oh my gosh, that last time when I got fired and driving away from Naples and how devastated I was. And gosh, it just was emotional. However, each time I go back, it's less and less. Right now it's becoming Naples is about health. LinkedIn Naples is no longer about that company I used to work for. But of course, I always wonder if I'm going to bump into people from the old company right when we're out for dinner. And it's just. It's surreal and a little nerve wracking, I guess, is the best way that I can put it. It's just the whole thing is freaking bizarre, frankly. Okay, so I am now a part of a team where people want me there, are grateful for me being there, and it feels completely different. So wherever you are, with work or in your life, give yourself a moment to assess. How are the people around you responding to you? For a long time, I was around people that really didn't want me there, specifically one person, but I would just try to ignore it. And I'm so grateful now to be surrounded by people who want me there, who are so appreciative of my opinion. You know, for years I had pitched myself to be on that company's board and I would get the runaround. I don't know about you, but I hate the runaround almost as much as I hate crickets. Right? Oh, we'll discuss it. We'll get back to you. Great idea. Food for thought, bs. So, you know, when I look back, if I were to give advice to my younger self, I would say, leave, get out of there. And even though it would have been scary, and I'm not saying it's easy, right, because you have a paycheck and you feel like you're in a safe zone, a familiar zone, what I didn't realize is the CEO position was going to change. It was going to be handed off to the woman that hated me. I was going to get fired anyways, right? So why not make the leap? Why not bet on yourself and take charge of that situation? That's the advice I would give me, is believe in you. Make the leap. You'll figure it out. And the sooner you do, the bigger and faster you're going to move and the bigger your business will get, right? Instead of, I'm coming up on my four year anniversary of being fired. That'll be July 27th of this year. And I think to myself, can you imagine how far ahead I would be right now had I left 10 years ago? Oh, my gosh, it would be insane, right? So, yes, I understand making a change can be scary. But I do want you to know that I wish I had made mine years ago, back when I felt that woman turning on me and belittling me and patronizing me. That's just not a situation for anyone to be in. Life is too short. And this past year has definitely taught us that. So make the move. Bet on you. You're worth it. And there are people out there that will appreciate you and want to be around you. Okay, so this is so crazy. I get home from Naples where literally there's no coronavirus. I roll into my apartment, there's coronavirus here, people wearing masks. So I put my mask back on and it was so funny that I'd forgotten about it. I get into my apartment and I say, okay, I've got to get organized and get ready for the upcomin. And something so big and so exciting is happening. This week. I have my first keynote presentation for Google. Boom. I mean, that's bucket list. And I'll tell you, I've had a lot of bucket list moments in the last year. I did a keynote for ypo, my first one. Then I did my YPO forum, which was huge. My first entrepreneur organization South Florida event. That was a live in person event. And I hadn't done one, a live event in a year. So there's been these big moments, right? And that's the one exciting thing of coming out of a pandemic is there's going to be big firsts again, right? Like, haven't done this in a year. And it's super exciting and it feels amazing.
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But the Google one I had really wanted to have the footage of me speaking with the logo behind me selfishly. And I get that. That's you know, whatever first world problem, get over it Heather. And I will. But I'm so excited to do my first Google keynote this week. I'm so optimistic about it, about what that means for my business and moving forward and I'm just. I'm super grateful for it. However, I am still really looking forward to the day I get to be there on their campus live and get that Google footage behind me. That will be next. This one's happening live from my computer. But the cool thing is that I am grateful for is that same day I can do a keynote on the other coast and I never even have to board a plane, right? So all of my events this week are virtual. Last week was all in person. This week it's all virtual. There's so much changing every week I feel like I don't know what to expect and what next live event will be booked and scheduling and figuring things out with my son. But the cool thing is, with so much change and so much opening and so much positive things happening, who knows what to expect next? And that makes me feel really excited. You know, don't forget, there's a fine line between fear and excitement. I choose excitement. I hope you're choosing it with me. Hold tight. We'll be right back. Meet a different guest each week. Okay, so I've been asked a lot, and I've seen so many DMs about this, asking me about getting fired. And then the other one is asking me about how to handle when people ask you to do things for free. So let me address the first one. Listen, getting fired is not a negative thing. We need to shine a light on shame. Extinguish the shame and reframe the conversation. You have been redirected, not rejected. There is nothing to be embarrassed about. Oprah Winfrey's been fired. Mark Cuban's been fired. J.K. rowling's been fired. I've been fired. You are now in good company. Whatever negative connotation you have for whatever situations in your life, reframe it. Shine a light on the shame and put it to work for you. It's exactly what I did. It's working out pretty well, and I strongly encourage you to do the same. The more you embrace it and are a champion of it, then you don't have to hide from it. And I actually just saw a post. Someone said, listen, I have to say I was lying. I told everyone I left the car business because I was over it. But the reality was I actually was fired. There's no shame in that game.
Own it.
That means those people weren't for you. You just fired your villain and it's time for you to take off. Embrace it. Put it to work for you. Okay, the other thing I've been asked a lot about this week, and it's because of a post I did on LinkedIn. I was so frustrated that three times in the same day I had DMs to me asking me to speak for free. Now, here's the thing. People provide a service, right? And I'm sure there's plenty of people out there that you know, are very, very independently wealthy and just want to do things for free. Good for you. That is not my personal situation. Currently, it's that time of year again.
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The goal is to be there one day, but right now I need to pay my bills and compensation's really important to me, right? Getting paid and evaluating where is my time best spent. My keynotes are a lucrative position for me, especially as live events come back because I get paid a lot more for live events than I do for virtual. So when people frankly waste my time with DMs that'll say something like hey Heather, are super interested in collaborating, working together, huge event coming up, I think you'd be great for it. Here's the thing I Could just dish everybody off to my agent. But I think that's kind of cold. If I'm gonna see the message, I wanna respond to it, right? Because. Cause people want to have more of a personalized response. Totally get. I'd want that too when I reach out to people. And you might make a good new connection and you could be networking, you never know. So if I've got the time, I see the message, I wanna respond. And it's been frustrating cause literally, as I mentioned, three times in the same day, I basically engaged with people in DMs and it was that each one of them had a non paid speaking opportunity that they felt I should do for free. One was international, which would mean I'd have to stay up till midnight or something. It was so crazy, it's actually comical. But here's the thing, if you don't value your time, no one else is going to, you know either. And when I first got into the speaking business, I felt I needed to do things for free because I wanted testimonials. I've got thousands of testimonials now. I don't need anymore. I'm good. Right? So maybe if you're just starting out, you want to do that to build up a little bit of credibility. Test your messaging. That's great. I'm beyond that. I'm 46 years old, I've tested my messaging, it's solid. Right now I'm in this business, I get paid for speaking and I don't want to disrespect Google and my other paying clients. That's ridiculous to me. I value them, they value me, we're doing business together. So I basically respond back to people. Hey, my podcast is free, my ebook is free, and my clubhouse events are all free. However, I am a paid speaker and if you would like to work with my agent to find a way to book me, please do so. I basically toss them off because I get very annoyed. But here's the thing, you don't need to apologize for that, right? For a while I felt, oh gosh, you know, that's not nice of me. Or what if it is a charity and there's no way. Well, here's what I came up with. I can toss people a prerecorded video link that they can use so that they can gain some type of a benefit from a message that I'm able to position non paid opportunities separately and differently than I do the valuable paid speaking engagements that I have, which respects my clients and myself.
Right?
We need to respect our time. So coming up with solutions like Clubhouse, like my podcast, like, you know, sharing a prerecorded video with someone that allows me to feel that I'm still doing good in the world, I'm still putting good out there. But most importantly, I'm valuing my time and my services, which is really important. And I want you to value your time and your services without apology. And it just remind me that, you know, Gary Vaynerchuk charges, I think charges $300,000 for a 60 minute keynote. That was the last I heard at the end, right before the pandemic had hit. That is what he was charging. And I don't think he ever apologized once for it.
Right.
I don't think he was sitting in his DMs feeling bad that people were asking him to speak for free. I'm pretty sure he would send the keynote fee or send the link to the agent and keep it moving. And that's what I'm doing and I hope that's what you're doing too, because you are valuable, you are worth it and people will treat you the way you teach them to. All right, until next week. I hope you love the shows this week. Please leave a review, subscribe, Rate, Review, Share it on social it means the world to me and it really helps so much. Until next week. I'll be creating my confidence. I know you will be too. I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. Come on this journey with me.
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