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Grounded Wildness ~ Break Free From Performing Your Life And Start Living It With Heather Whelpley

In this highly competitive environment where everyone seems to be thriving, it can be so easy to fall into the trap of constantly proving your worth. Sometimes, at the detriment of who you truly are. This begs the question, are you performing your life or are you living it? This is the premise of Heather Whelpley’s book, Grounded Wildness: Break Free from Performing Your Life and Start Living Itwhere she tackles the problems many women face in trying to prove, please, and perfect their way through life. In this episode, this speaker and award-winning author joins Rosie Zilinskas to tell us more about this, diving deep into the pressures of this world and the constant pursuit of perfection. Heather also shares her journey from the corporate world to becoming an entrepreneur. She talks about her struggles of being an overachiever and discovering the freedom that comes from owning your worth. Let this conversation inspire you to live out loud. Stop performing and start living today!



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Grounded Wildness ~ Break Free From Performing Your Life And Start Living It With Heather Whelpley

I am pleased to have Heather Whelpley join me. We’re going to dive right into the conversation discussing her upcoming book, Grounded Wildness: Break Free From Performing Your Life and Start Living It. She is a speaker and award-winning author. She’s going to share her insights on what it means to perform in our lives, how we can stop performing, and how to start living authentically.


We’re going to talk a little bit about the pressure of having to prove your worth, pleasing others, and the constant pursuit of perfection. She’s also going to share her journey on how she was in the corporate world and how she was able to stop being an overachiever and become an entrepreneur. Stay tuned for my conversation with Heather.



Heather, thank you so much for being here. How are you doing?


I am great. Thank you so much for having me, Rosie. How are you?


I’m doing well. I’m excited to have this conversation. I’d like to jump right into the conversation. I know that you have a book coming out.


I do. We’re doing this a few days before the official launch of Grounded Wildness: Break Free From Performing Your Life and Start Living It. It’s coming out on Tuesday, October 17th, 2023, on my website, and on November 2nd, 2023, with the eBook, audiobook, hardcover, and journal on Amazon.


Along those lines, the first thing that I wanted to ask you is you talk about performing in your life, what do you mean by that? How do you stop performing, and how do you start living your life?


I feel like the entire book answers that question. I’m going to dive into it. I love it because we all perform in our lives to a degree. That can generally be thinking about what are the masks that you put on. I think of performing as anything that takes you away from you. It’s all of those comments or conversations that feel a little bit off.


I’ve found that they tend to fall into four different categories: Proving, Pleasing, Perfecting, and Rebelling. Those first three all have something in common. Proving, pleasing, and perfecting, which is what we do to try and prove our worth through living up to the rules, the standards, the expectations, and all of those shoulds and supposed tos about how we’re supposed to show up in every part of our lives. It’s from how we’re supposed to show up in the workplace to what our bodies are supposed to look like, to be likable, to all these forms of being good.


All people, regardless of their gender identification, have rules that are handed to them. This book focuses on those that are specifically handed to women growing up. Rebelling is the opposite side of that. I don’t see it as much as proving, pleasing, and perfecting. I will fully admit it. It’s when you’re pushing against those rules, standards, and expectations, not because it feels authentic, but to push because you’re like, “I’m going to do something different because it’s different. I’m going to argue for the sake of argument, even if it doesn’t feel authentic and real to me.”


I see both of those. For me, that showed up in a whole bunch of different parts of my life. In the workplace, that showed up with my voice in particular. I was one of those millions of women out there who got feedback that I could be too direct. I was asked to slow down. I had a manager, who’s an amazing manager in many ways, tell me to sit on my hands in meetings as a reminder to slow down. Because I was also this overachiever and overdoer, I took all that feedback way to heart and followed it all to the nth degree, which made me sit in meetings, questioning my voice, how to show up, and how to share my voice and share ideas without getting that feedback that I could be too direct.


Over time, that caused me to start performing with my voice, where I didn’t feel inauthentic or fake by any stretch of the imagination. I knew I was holding back in a way that went beyond simple awareness and emotional intelligence. I was filtering myself over again. It showed up in that part of my life and with my body. I’m feeling ashamed of my body, and I had to prove myself in other ways because I didn’t feel like I was in a larger body growing up.


I felt like that wasn’t good enough, and I needed to prove myself because my body wasn’t what it was “supposed to look like.” It wasn’t beautiful and desirable. All of these ways of proving, pleasing, and perfecting showed up in my life and are common among many women out there. I’ll answer the second part of your question, but there was a lot there. I wanted to pause and hear your thoughts.


I like how you had the proving, pleasing, and perfecting. That goes along the lines of women in the corporate world trying to get a footing and figure out how they can get those new opportunities or advancement opportunities. You said that your manager told you to sit in your hands because you were lively with your hands. How is it that you took that feedback?


It almost sounds like you took it to heart. You took what he said and applied it. It’s just one person. How do women in the corporate world specifically take feedback like that and learn from your story, not take it to heart as much, but at the same time listen so that they can learn from the tools they’re being given to develop those tools?


I love that you asked that question because I never want to come across as thinking we should ignore feedback because feedback can be important. I’ve gotten wonderful feedback from some of the same managers and people who also gave me feedback that I was direct. They gave me valuable feedback that was great for my career and my life as a whole.


I also want to point out that you use the pronoun, he. All my managers were women. Every single time I got this feedback, it was from someone who identified as a woman. It’s not every day, but it did happen more than once. I think about 20% of that feedback was helpful. It was helpful because I didn’t want to railroad over anyone. I want to be inclusive. I want to listen. What would’ve been helpful would’ve been for me to take a step back out of my perfectionist self and be more objective and ask what of this feedback is useful and helpful. What can I throw out the window?


Some of that’s being useful and helpful on an individual level. We’ve all been in those situations where we’ve gotten feedback that is not actionable and helpful. Even if you try and follow up with the person and learn more, you’re not getting anything that’s helpful. That can be feedback to throw out the window.


It’s also important, and I got this originally from Tara Mhor’s book Playing Big, where she said in that book, “Remember that every time you’re getting feedback, it’s coming from that person’s perspective. This goes from both positive and constructive feedback. When someone gives you a compliment, it’s coming from their perspective. When someone is giving you constructive feedback, it’s coming from their perspective.”


NWB 82 | Grounded Wildness
Grounded Wildness: When someone gives you a compliment or constructive feedback, it’s coming from their perspective.


It’s a neutral way to look at feedback. That’s been helpful for me across all kinds of feedback to say, “What if this is just their perspective? What’s helpful? Where am I finding commonalities across feedback that I want to take in, use, do something with, and change?” Sometimes, that question is also, “What of this feedback might be based on bias?” That’s not all feedback by any stretch of the imagination, but I do look back on the feedback that I’ve gotten, and it is highly unlikely it ever would’ve been given to a man.


I hear particularly from Black women who get the feedback that they’re angry when they’re not angry. They’re not showing any emotion that is even remotely inappropriate. Because that feedback is based on bias, that’s the feedback that they are getting. It’s helpful to take this step back and choose what is going to be helpful and useful. Ask yourself some questions about it, and do your best to let go. I’m curious. You’ve been in the corporate world, and you coach women. What do you think about this feedback piece because it can be complicated?


The specific feedback that you received where you should sit on your hands, can you imagine a man getting that feedback and being like, “What are you talking about? I’m not going to do that.” It’s ridiculous that they’re asking you to sit on your hands because you’re expressive. I agree with you that taking what you need, what serves you, and leading the rest is going to be the right thing to do.


However, there is good value if someone’s telling you, “You need to improve your turnaround service,” or something that’s specific. That’s recommendations that you can work on and develop. Feedback can be tricky. I love the quote that you said that it’s from that person’s perspective, and that’s key when getting feedback.


I’m going to add one more thing to that because many of us want to be liked as people, but we want what we’re putting out in the world to be liked. It simply isn’t going to be liked by everyone, no matter what you are creating or doing, because we all come from that different perspective. I had a helpful realization when I thought about this from anything new that you’re doing, creating, or putting out into the world. I was like, “There are Pulitzer Prize-winning books that I didn’t like. There are Oscar-winning movies that I didn’t like. There are movies that didn’t get the best reviews, but I love them.”


A lot of it is perspective and not everyone is going to like everything that you put out in the world. It doesn’t mean you should ignore it all either, but it’s a helpful thing because, as women, we have been given these direct and indirect messages that part of our worth is in being liked by everyone and that everyone should like everything we do. It’s simply not possible.


I’m going back to the introduction that you gave us. Knowing your worth is something that I find a little bit controversial. As a human being, we’re priceless. When I talk about knowing your worth, can you show your professional value so that you can get paid commensurate to what you believe you should be getting paid? A lot of times, women don’t know how to express their worth or professional value. You talked about that a little bit.


That goes along with the people-pleasing where we, in the corporate world, have been programmed, especially the Gen X-ers or the older generation. We’re programmed to not talk back, respect authority, and not talk about pay. How did you come again to start shutting that and start living your life authentically without the people pleasing, proving, and realizing your worth?


It is a journey. It still comes up from time to time. There are two different parts here. I’m glad you brought them both up. One is that deep realization that you are worthy as a human no matter what. You don’t have to prove, please, perfect, rebel, or do anything in order to prove yourself. You don’t have to work harder or do more to prove yourself as the value of a human.


I had some deep realizations around all of these rules that we are handed that tell us that we are supposed to prove, please, and perfect to show our worth, to hustle for our worth, and to show other people through our bodies and likability. I had this deep realization when I was in the middle of a breakdown of like, “I was never broken. It was always those rules that were handed to me that were broken. I never had to prove my worth.”


This is a race that can’t be won because the race doesn’t exist. You can’t ever prove your worth because your worth is inherent. I realized that in all areas of my life, as it related to my voice and speaking up, as it related to owning my strength as a speaker. When I left my corporate roles and became a speaker, I felt a lot of arrogance, self-questioning, and things getting on the stage. I was like, “I have value to add, but I don’t have anything to prove.”


It allowed me to show up better in relationships, dating, and all of these areas because I realized that in any place where I felt like I was broken, I was never broken. I was always worthy. That was massive for me. Interestingly, that realization allowed me to own my worth in the second way that you’re talking about it in an easier way.


I don’t think I’d ever put that connection together until now as we are talking about this. You ask that question together because we do need to own our worth in a valuable way. When you don’t feel like you have anything to prove and you don’t feel like something has to be perfect in order to share it or that you feel like you don’t have to be perfect in order to put yourself out there, that allows you to own your value in an easier, stronger way. You can be like, “This is what I’m good at. I’m not perfect, but here are all the things that I’m great at. Here are the places that I am adding value in my role to my clients and company.”


It allows that second part to be easier. It allows me to talk about my strengths without feeling like I’m bragging or I need to shy into the corner. I’m not allowed to talk about it. I should put my head down. Hopefully, people will notice. When you are able to be free in your worth, it allows you to do all those other things a lot more easily.


It’s interesting that you said, “There is no race to start because the system is a problem.” The fact that men are the whole patriarchy. I spoke to a woman who did a lot of policy writing on the pay transparency laws. She started doing that several years ago. She said, “It’s interesting how women try to get to that value or worth when they start here, and the men are already way up here. The system is what we need to work on.”


I love that you had that realization that it wasn’t you that was the problem. It’s not that you shouldn’t take responsibility for your life. When it comes to the system and the way the system is set up, it’s rigged. It’s so interesting because what I have found is a lot of women are trying to advance in their corporate careers by working harder. They don’t have a strategy to move up the corporate ladder. There are strategic things that women can do to get to that next level, whatever level there is, instead of working harder. Can you relate to that?


I was in corporate jobs for several years in a wide variety of HR and leadership development roles. I had no idea how to set boundaries. I had no idea how to do less. It was partly proving my worth through achievement and success piece. I genuinely like to be involved in everything. I’m an enthusiastic person. Yes was my automatic answer to everything for a whole variety of reasons. That meant I was burned out and tired. That meant sometimes I didn’t have the capacity to work on the things that were most important. I got bogged down in emails and things that were not as important, which most people can probably identify with.


It’s been true both in my corporate career and in my business, where I’ve had to take a step back and be like, “What is going to make the biggest difference here? What is going to make the biggest difference in my business and the impact that I want to create?” I see that frequently with women inside corporate. This is a small example, but it impacts many people by automatically accepting every single invite that you get to a meeting.


Do you even know why you’re there? Do you understand the purpose of the meeting? Do you know why you were invited to it? If you don’t, ask those questions because you don’t have to attend every single meeting. That can easily free up some space to work on what is most important. Automatic yes does not have to be your go-to and modest up-run dive. How you go through life is to say yes to everything. We need to take that step back and say, “I can figure out what is most important.”


Sometimes, if you don’t know, you can talk to your manager to figure out what those priorities are that are visible, going to create the most impact and be good for your career, the broader team, and the organization. They can all go together, which doesn’t mean it’s easy. I know a lot of people have more work on their plate than what they can complete. I don’t want to make it sound like, “This is your own issue. You need to figure it out.” It’s a broader issue. It’s an issue we can influence with our personal decisions by questioning and choosing.


I want to be clear. When we’re saying breaking free from performing in your life, what I heard from you is realizing that you are not broken, you are not the problem, and the system needs to change. Did I get that clear?


NWB 82 | Grounded Wildness
Grounded Wildness: Break Free from Performing Your Life and Start Living It

Yeah. This is both a systemic and an individual piece because the proving, pleasing, and perfecting that we feel and sometimes rebelling never originates inside of us. None of us are born feeling like we need to prove, please, or perfect. That does come from the messages, rules, expectations, and environments that we have around us.


I want to be clear. Every person on this planet is handed rules that come not from society and culture but from our families, teachers, and personal experiences. Some of them are good messages. Everyone has ones that are handed to us that are not helpful that we need to break down and choose to let go. I do want to be clear about this. I have found that when I started to separate my worth from those things, I was like, “I was never broken. It was the rules that were broken.”


It was easier for me to take personal accountability for the things that were mine because I had greater self-compassion. I could say, “This is why I feel this way. It’s because of these rules and expectations that were handed to me. This is where I can make a change. This is where I have personal accountability. This is where I have responsibility.”


When you don’t feel like you have to perfect things, or you don’t feel like your worth is dependent on things going well or that you have to do well and everything, when you feel like your worth is not dependent on that, it makes it easier to try new things, change, and listen to the feedback that is helpful because your worth isn’t dependent on already doing everything perfectly. It has given me more freedom to listen, change, and take personal accountability with greater self-compassion at the same time.


You’ve heard about the quiet quitting and the people not being engaged. I was reading an article on how people can become more engaged. The one thing that I don’t see people talking about is that when you’re in your day-to-day, you’re not paying attention because you’re used to the activities that you do. They’re generally the same.


When you get to the point that you’re like, “I have to do this again,” that’s when you need to make a change and bring novelty into your work. Once you bring novelty and if you are working on a brand new project that you’ve never done, it makes your brain pay attention. That’s when you start becoming alive.


I saw this TEDx speaker say, “If you want your year to get longer instead of shorter, do new things, travel, and try different activities altogether.” Your brain, when it starts trying all these new activities, it feels like time expands. He also said, “That’s why when we’re little kids, everything is new. The time is long when you’re a child.”


I’m going back to the workplace. If we don’t get out of our comfort zone and try to do new things, it becomes repetitive. That’s where you get stuck. I know that you talk a little bit about reigniting your confidence. Sometimes, when people don’t know what to do, that’s when they become disengaged in quiet quitting. How would you recommend someone in the corporate world to reignite that confidence or re-engagement in their work?


I have many ideas that came to me as you were asking that question. One, I love that you brought up aliveness. That’s a chapter in the book Grounded Wildness. It is called Following Aliveness. That’s something that we can use in our lives as a whole. Sometimes, reigniting that confidence and aliveness is paying attention to like, “What makes me feel alive at work and outside of work?” If you’re in that quiet quitting phase at work, start by paying attention outside of work. One phase of our life can bring it into another. Sometimes, if you’re burned out, you need to sleep, rest, and rediscover your aliveness.

“Sometimes, reigniting that confidence and aliveness is just paying attention.” – Heather Whelpley Share on X

I live in Colorado. I love to hike. It makes me feel alive immediately. It reconnects me to my liveness in all parts of my life. It helps me to center back into myself and get rid of some of that inner critic and other opinions people have and get into myself. Following aliveness is something that we can use in all parts of our lives, including in the workplace.


Are there parts of your job that do spark aliveness? Is there something you heard about at a town hall or whatever that’s like, “That sounds interesting. Could I get involved in that? Could I do something different?” Sometimes, that means taking on an extra project. In my last corporate job, I asked my manager, and I was like, “Can I design this course called mindfulness and self-awareness?” I was interested in it. I ended up running it through the wellness club. It’s not an official part of my job.


It gave me joy and aliveness. It allowed me to explore this whole other area that I was interested in. It wasn’t in my day-to-day job. Following aliveness can repark you. We all have parts of our job we don’t like. I love my work. There are still parts of it that I’m like, “If I could figure out how to outsource that one, I would.” The more we can stop and say, “What brings me alive? How can I do more of that? What deadens me? What doesn’t make me feel alive? How can I decrease that?” Not to zero because that’s unrealistic, but how can you decrease what deadens you and increase what makes you come alive?


That’s a question we can ask across our entire lives. When we are more alive, that confidence is going to be a lot easier to come by because we’ve been around those people who are alive. They’re not even thinking about, “Am I confident?” They’re alive and present in what they are doing. The confidence comes across. There is a connection here between aliveness and reigniting your confidence.


I like that because a lot of times, you don’t think of doing new things or asking to be involved in that new project. That’s when you start paying attention because you’re like, “It’s something new. I have to pay attention. That’s when you feel a little bit more fulfilled. At the very beginning, you had mentioned that you were an overachiever. Are you still an overachiever? How did you let go of being an overachiever?


I would say I’m like 90% let it go. I’m still an achiever. I want to be clear. I enjoy being productive and creating an impact. I love the work that I do. That is all true. My first book is called An Overachiever’s Guide to Breaking the Rules. Someone asked me at the beginning of that. They’re like, “You wrote this book on letting go of overachieving, but writing a book is an overachiever thing to do. What do you think about that?” I was like, “That is a good point.”


NWB 82 | Grounded Wildness
An Overachiever’s Guide to Breaking the Rules: How to Let Go of Perfect and Live Your Truth

I overachieved in high school and college. I didn’t always take the standard path, but I overdid everything. I already mentioned in my corporate career that I had no boundaries. When I got into my business, it was even worse because I felt like everything was on me. I put all these expectations and pressure on me. I was burned out.


I finally stopped, slowed down, and asked myself, “Why am I doing all of this?” The answer came to me immediately. It went back to prove my worth and not through any one person or my parents. It is these general cultural messages that we get, especially in the US and many other cultures around the world. You always have to do more, and busyness is your worth that you always have to be productive. I overdid all of that.


When I finally stopped to explore that, I could see those messages that I got, and I was like, “I don’t have to keep following those messages. I can choose to let go.” It was a journey. It did not happen overnight. It was several months of active work of being like, “I am worthy for who I am, not what I do.” Choosing to let go of that and challenge those rules that I had gotten allowed me to have a lot more freedom in my life. Before I realized all these other rules around likability and being good in our bodies, the overachieving one was step one. That was the gateway.


I talk about that in a lot of my speaking engagements around creating your own rules for success and taking that step back and saying, “You might’ve been handed all these rules, but what’s your definition of success? What’s important to you? How do you want to be showing up in the world? What do you want as opposed to what you were told you were supposed to want?” There might be an overlap there, but it’s worth asking those questions and creating some space to reconnect to yourself and separate from all those rules.


One of the things that women are apt to, like you said, is we are rule followers and people-pleasers. I’ve said this 1 million times on my show, but men apply for jobs and have the skills. Women feel that they have to follow all of the job qualifications. That translates into you’re a rule follower. I worked with one of my clients. She’s like, “I can’t apply for that job because I don’t have all the job qualifications.” It turned out that she was a rule follower. She didn’t feel that she could apply for that particular position.


When you have more than 80% or 90% of the job qualifications, you’re overqualified. By that time, the job is gone. I like that you were specific in saying that it’s a journey because understanding why you tick the way you tick is important in finding that big why. Why are you doing things? You ask yourself that. You’re like, “Why am I doing this in your journey?”


You can ask yourself that question with openness and neutrality. For a long time, I asked myself that question with judgment. I was like, “Why are you doing this? Why can’t you figure it out? Why can’t you set better boundaries? Why are you burned out again? Why do you feel guilty about this?” All of these are self-judgment-wise, as opposed to pausing and being like, “Why am I doing this? What’s going on here? What has been fed to me from everything around me versus what’s my own personal accountability?”


The open neutral to self-compassionate why is where change comes from. Change does not come from self-judgment. If self-judgment worked, we would all be perfect now because we have been judging ourselves since we were twelve years old or earlier and younger, depending on the person. That middle school time is when we started judging ourselves and trying to prove, please, and perfect. When we can ask why with openness, that’s what leads to change and freedom.


Pleasing is always such an issue for me because sometimes, you don’t know if you are saying yes because you’re trying to be helpful and provide value or if you’re a yes person. Yes, because they told you to do it instead of reflecting and taking a look at what they’re asking you to do. I also like that you said, “You don’t have to accept all the meeting invites.”


It’s one of those things that you have meetings back to back, and you feel like you have to go to all of them. You may not have to go to all of them, but when it comes to the people-pleasing component, what are some questions that are good questions that you can ask yourself? Am I doing it to provide value, or am I doing it because it’s what I’ve always done?


The question you asked is a good one. Am I doing this to provide value, or it’s aligned with my values? Is it because I’m doing it because it’s what I’ve always done? You may not know the answer to that question when you get started. Starting out with openness and starting to pay attention. The other piece that’s been helpful for me, especially in saying yes or no, is noticing how I feel in the moment of saying yes or no and afterward, like later on or when I’m doing the thing.


Do I feel excited, or do I feel resentful? Does it feel overwhelming to say yes, or does it feel fun to say yes? I already told you. I like to say yes to a lot of things because I’m enthusiastic and want to be involved. I would have to fo fast forward myself and be like, “How am I going to feel doing it? Am I going to feel overwhelmed then? Am I going to feel resentful that I said yes then? Am I not going to be able to give it my full time and energy? Even though I want to do it, I don’t have the capacity to do it.” I’m asking myself those questions.


I started asking myself this question in a corporate job. I had said yes to an ongoing project that was volunteer work that I loved. I was excited about it. It was aligned with my values, but it was four extra hours of work on average a week for a year. It was massive. I said yes. It felt like an aligned and enthusiastic yes. I still should have said no because I didn’t ask myself these fast-forwarding questions. Do I have the capacity to do this? Am I going to be able to do this? I forced myself to do it. I did do it, but I was exhausted.


This was many years ago. I still use this question. If I say yes to this, what am I saying no to? Oftentimes, those two options or multiple options are not stacked right next to each other. It’s not like, “If I say yes to A, I’m saying no to B.” It’s worth asking yourself that question. If you say yes to this project at work or this meeting, are you saying no to sleep? Are you saying no to spending time with your friends and family? Are you saying no to exercise? Are you saying no to a different project that creates greater impact and visibility for you in all of these things?


I try to get in the habit of not automatically saying yes. Pausing is first of all. For anyone who’s an automatic, “Yes, sir,” get yourself some more time. Tell the person like, “I’m going to get back to you on that one.” You don’t have to say yes or no most of the time. You don’t have to say yes or no at the moment. Get yourself a little extra time. Reflect and choose more consciously on what you’re going to say yes and no to.


NWB 82 | Grounded Wildness
Grounded Wildness: Most of the time, you don’t have to say yes or no at the moment. Get yourself a little extra time to reflect and then choose more consciously what you’re going to say.


This was a huge issue for me. It still comes up occasionally. I still get to the point where I’m like, “I said yes to many things there. Let’s take a step back and figure out what I’m going to say no to.” I haven’t dug in so deep. It used to be every day, I said yes to many things. I don’t anymore. It does make a huge difference in the work that I’m putting out there, my overall well-being, aliveness, and all of those things that we’ve talked about.


I love how you said, “If I say yes to this thing, what am I saying no to?” You are taking a little bit of time to reflect and say, “Is this taking away time from me from working out or sleeping.” As women, we always give to those people around us, but we don’t put ourselves first either. One last question. You talk about the slow walk away from yourself. I know you’ve already talked a lot about that. When did you realize that you were almost saying no to yourself by saying yes to other things with the slow walk away?


My corporate career was this slow walk away for me, even though I also had fantastic experiences. I worked for good companies, had great managers, and did amazing things. There were many good things about my corporate career. I have no regrets about it. I’m happy that I was in corporate for several years. It was that slow walk away, particularly from my authentic voice and sharing it.


I talk about this in my keynote on Discover Your Authentic Voice and How To Use It To Lead Change. I realized that I have these two sides of me that are both authentic. One side is this sweet, happy, bubbly, and cheerful side. It’s the definition of how a woman is supposed to show up in the world. That is a real part of me. I call that side the sweet girl side.


I have this other side of me that is fiery, bold, and direct. I realized in my corporate career that a sweet girl was always welcome at the table. She never got criticized or told to slow down or be less direct. She was always welcome at the table, whereas this fiery side of me got mixed reviews. There were people who loved it. I got complimented for being able to show up in meetings with senior leaders in my twenties and being able to share ideas and opinions. That was also the side of me that got criticized and feedback. I felt like that side might be too much for people.


I started to rein it in overtime and pulled her back. Don’t get me wrong. I was never quiet. It became this imbalance where I felt like I was holding myself back 20% or 30%. I’m not even sure. I’m trying to think if there was an exact moment when I realized this. I always felt like I was a little bit disconnected from my intuition and the guiding force inside of me. It was a slow journey to get it back and to start listening to myself.


I don’t know that there was an exact moment where I was like, “I had this slow walk away from myself.” Now, I’m walking back to myself. It happened through all of this other work that we’ve talked about creating space to listen to myself and recognizing where those rules had told me that I was supposed to hold back and I was too much.


None of us are ever too much as a person. The rules are telling me that. It was a slow walk away, but then it was a slow walk back. It was because of following aliveness, creating the space to listen to myself, and realizing how the rules and expectations impacted me. It was a conglomeration of all of those things. We all need more space.


The first chapter in the practices part of Grounded Wildness is called Create Space because, without some space, you can’t follow aliveness. You can’t know what you want. You can’t listen to yourself. It’s hard to be confident and to take up space in your work when you don’t have any space to be in the first place. I believe that is step one to coming back to yourself if you also feel disconnected or feel like you’ve had a slow walk away from yourself, whether that’s in work or your life as a whole.

“It's hard to be confident and to take up space in your work when you don't have any space to just be in the first place.” – Heather Whelpley Share on X

What was the transition from going from corporate to becoming a speaker?


I was in my corporate jobs. I worked for several years for two large multinational companies. I lived in Australia. I worked in Latin America and the US. I had a great career. In the end, my job changed outside of my control. I had never had any intention to be an entrepreneur or a speaker. The speaker piece was in the back of my mind as this secret dream.


I wrote on a Facebook post in 2013, years before I became a speaker, that my secret, maybe achievable dream was to become a motivational speaker, inspiring people to be their authentic selves. This popped up in my Facebook memories a few years ago. I was like, “I knew what I wanted to do several years ago.” I wasn’t listening to that voice.


My job changed. It changed in a way that was outside my control and in a way that I knew I was going to hate. I did have no interest in this job change. This happens sometimes in places of employment. Things happen outside your control. For whatever reason, at that moment, I paused and was like, “Let me explore what I want to do next.” Instead of saying to my manager, “This isn’t going to work,” or immediately applying for other corporate roles, which I could have done, I took that step back. I have been doing this for several years, and I started my corporate career late. This was in my late 30s. I was like, “Let’s take a minute and think about what I desire and want in my career.”


I did the book Designing Your Life, which gives you all sorts of different reflections and questions. It took a few months to do that. I say that that’s like a book you do rather than read. It’s true if you’re working with a career coach. These things do not happen in a week. They happen over time. Because of that, I was like, “Entrepreneurship is for me.”


As soon as I started considering that, all these ideas started coming towards me for books I could write and speaking engagements I could do. Even within that, my first year or two of running a business, there were lots of failures and figuring things out. I was not a speaker right away. I was doing more coaching. I was going to write a different book that I shelved. I had the entire book outlined. I was about to start writing it. I shelved the entire thing because I was like, “This is not my book.” There was a lot of experimentation.


I found a combination. I wrote An Overachiever’s Guide To Breaking The Rules. I saw that people resonated with that. I started speaking on imposter syndrome, which I still speak on, and tons of people resonate with. I speak a lot for women in employee resource groups and conferences on that. This whole idea of creating your own rules for success and being that perfectionist overdo or overachiever and taking a step back and saying, “What do I want?” It is that keynote. It resonated with people.


As I looked at my business, not all of it was going great. There were things like multiple failures in my business, but I love to speak and write. I was creating an impact there. I need to work on it both. We always need to improve our craft and the business side of things. It was coming to me. The feedback was there. People were like, “This is impactful for me. I’m taking things away I can use at work. I can use it in my personal life. I’ve never thought about this before. This is thought-provoking. I want more of this.” I started to shift away from the things that weren’t working towards the things that made me come alive and were work.


It gave me joy and created an impact that overlaps all of the things. It was a journey. I never considered being an entrepreneur until several months before I put in my notice and did it. I’m glad I spent several years in corporate and I’m doing what I’m doing now. I love it. It’s been a good journey, but one of ups and downs and all around for sure.


Everything that you shared with us is incredibly impactful and valuable. Heather, is there maybe one particular tip that you want to make sure that the audience understands that would be valuable for them in their corporate world?


I’m going to say two if that’s okay. One is we’ve talked a lot about these rules and expectations. Simply starting to notice in your life, work, corporate world, and roles outside of work, where are those rules showing up for you? Where do you feel like you need to live up to some standard that maybe didn’t come from inside you but came from other things? Simply, as a step one, start to notice that because that is going to be your walk back to yourself. You can separate out and choose on purpose.


Not all rules are bad. I don’t think we should throw all the rules out the window. You get to choose on purpose. I still adapt my communication style depending on who I am with and the audience. I don’t feel like I’m walking away from myself by doing that. I can be authentic, hold onto myself, and adapt at the same time. They can both be true. I don’t have to twist myself into someone that I’m not in order to be effective. Recognizing the rules helps people to start to do that.


Tip number two is what I talked about earlier, but I’m going to reiterate it because it has been the foundation not only for me but for many people and women that I’ve worked with, which is to create some space for yourself. Create some space where you do not have to be in demand to others, not helping others, or not listening to a podcast or an audiobook.


Sometimes, we think of these things as you have to do these in big ways. If you’re feeling the need for that, do it. Take a vacation by yourself and challenge yourself to make that happen. It can also be taking a 20 or 30-minute walk on a regular basis without looking at your phone, listening to a podcast at the same time, or setting a timer for five minutes and writing to a prompt like, “What I’m feeling now is. What I want is.” We can build in these small ways of creating the space to reconnect to ourselves. That is going to lead to only good things in your corporate career and your life as a whole for your well-being, freedom, joy, and everything. Notice the rules and create space.

“Notice the rules and create space.” – Heather Whelpley Share on X

Tell us about the name of your book.


It is called Grounded Wildness: Break Free From Performing Your Life and Start Living It. Starting on October 17th, 2023, that is going to be available on my website, which is You’ll be able to get signed hardcover copies there, assuming you are in the US. Starting on November 2nd, 2023, the hardcover eBook, audiobook, and companion journal, which I’m excited about, will all be available on Amazon. You can get both of those there.


My website,, is where you’ll also find information about all my speaking engagements. If you liked what you read here and you’re interested in bringing me into your organization for a women’s leadership event, International Women’s Day, or an employee resource group, all of that information is going to be there.


Heather, thank you again for taking the time and giving us so much value. Saying no to meetings was huge. Thank you again, Heather. I appreciate you.


Thank you so much for having me. This has been a great conversation. I appreciate it.



I had some great a-ha moments from my conversation with Heather. I liked that she said that by separating our worth from external factors, we take personal accountability for our lives with greater self-compassion and that societal rules are the ones that are broken and we are not. Heather leaves us with two great tips. She says, “Follow aliveness.” She suggests paying attention to what makes you feel alive, both inside of work and out. She also says to challenge the rules. Heather is also gifting us with a guide. It’s the ultimate guide to saying no at work, which can be found on her website,


If you are ready for your next promotion but you’re not sure where to start, I have a great tool for you. I would like for you to complete the free three-minute checklist to find out what’s holding you back in your career. No more guessing games. You will be able to pinpoint exactly where you need a boost to accelerate your career. Once you’re in the know, you will be unstoppable. With that, remember to be brave, be bold, and take action. Until next time.


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About Heather Whelpley

NWB 82 | Grounded WildnessHeather Whelpley is a speaker and award-winning author that works with women to break the rules that cause us to prove, please, and perfect so we can reclaim freedom, rediscover our voices, and take up space. Her podcast, Grounded Wildness, and two book, An Overachiever’s Guide To Breaking The Rules and Grounded Wildness: Break Free From Performing Your Life and Start Living It, will guide you in breaking the rules and reclaiming your freedom. Before becoming a speaker and author, Heather worked in a wide variety of HR and leadership development roles for multi-national companies in the US, Latin America, and Australia for ten years. Heather lives in Colorado where she spends as much time as possible hiking, exploring, and getting connected to her grounded and wild self.