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Breaking the Rules as an Overachiever

with Heather Whelpley

I’m excited to share a conversation I recently had with an expert on imposter syndrome and perfectionism. She has inspired thousands of people at different companies and conferences across the United States through her keynote speaking engagements and webinars. Heather Whelpley is a speaker, author, and consultant who guides women to let go of others’ expectations and instead create their own rules for life. 
Heather published her first book, An Overachiever’s Guide to Breaking the Rules, in 2020, which I just finished reading myself. I could not wait to explore so many of the topics that Heather talked about in her book on a recent episode of Elite Achievement. I start our conversation by asking what initially inspired her to leave her corporate role after a decade of working at multinational corporations.

Heather’s Early Days as an Entrepreneur

“It was really two different things,” Heather begins. “And I will tell you, one was pretty out there, and one was very concrete and tangible. The first thing that happened was about five and a half years ago. I was having a career development conversation with my manager, who I had a great relationship with. I was telling her that I wanted to be a director, be part of strategy, and be a team leader. And in the middle of this conversation, a voice came to me loud and clear and said, you are lying right now. I’d never heard anything like this before, so it was like, I have to pay attention to that voice. I also didn’t know what it meant. Then a few months later, my job changed very concretely to something I knew I was going to hate. My entire body had this visceral reaction against it like no, this is not going to work, you’re going to have to make a change very quickly. It was also my birthday when I found out about the change, which I feel was a message from the universe. I knew a change had to happen. But I didn’t know what that change was. I’d never considered being an entrepreneur. I decided to take that step back and think about my options. Should I apply for another job at a different company? Should I try and negotiate out of this role? Or should I broaden and consider things I’d never considered before?”

Heather explains how she took a few months and did a deep dive, going through the exercises she outlines in her book. She started talking to entrepreneurs, and as she explored those conversations, possibilities began to open up. Heather shares that she was flooded with ideas, most of which she didn’t end up doing, but it inspired high energy and creativity that led to her giving notice to her employer five months after she found out her role was changing. She knew she wanted to coach and speak, but it wasn’t all clear yet. 

“The whole first year was like throwing spaghetti at a wall to try and figure out what this business was really going to look like,” Heather says. “But that’s what inspired me to leave my corporate role.”

I’m so appreciative that Heather shared a couple of very specific things. I heard her say that she took a step back and asked herself, what are my options? I know it can be tempting, in the moment when you’re feeling emotional, to make these decisions that can’t be undone. It’s okay to take a step back, pause before deciding, and explore options. And the second thing I heard Heather say was that she had a lot of conversations. So often, when we’re trying to make a big decision, we get all up in our heads. And I heard her say she started talking to a lot of entrepreneurs. And through those conversations came this energy. It’s that reminder to take action because that’s where we can get a lot of clarity.

“Yes,” Heather confirms. “For me, it’s always been this balance between self-reflection and outward action because I learned without doing both, I can take action that’s not really aligned to who I am, and that true inner voice, and my own values. I learned so much from every single person that I talked to. I had some family members who were entrepreneurs but not my direct parents. And so, I didn’t know what being an entrepreneur was like. I didn’t feel like I knew what those possibilities were until I started talking to people. And that’s when the ideas started flowing. That combination of reflection and outward action has always been really important to me.”

I resonate with the blend of self-reflection and outward action. One of the questions that I keep reflecting on is why I feel like whatever I achieve is not enough. I constantly want to do more and go bigger. And when I saw Heather’s book, I thought, hmm, maybe I’m an overachiever. So, I ask Heather, how do we know if we are and what is the definition?

How to Know if You’re an Overachiever – What’s the Definition?

“Oh, that’s such a great question,” says Heather. “So first of all, I want to be clear, there’s nothing wrong with achieving. There is nothing wrong with making an impact or working hard. These are good things. And I still want them even though I wrote a book called An Overachiever’s Guide to Breaking the Rules. I still want to have a successful business and do well. To me, the crux of being the overachiever is partly just in that first part of the word, which is the over. The overachieving, the overdoing, it’s working harder than you really need to work. And the root of that is that somehow, somewhere, you are tying your worth to achievement. At least that’s what it was for me. I don’t want to give that answer and say that it’s true for everyone. It was certainly true for me. I was trying to prove at least a part of my worth as a human through this external achievement by getting things done, doing them well, and having them validated by other people. And if that’s the race you’re in, it isn’t ever enough, partly because we can’t ever prove our worth. We are already worthy. So, you are trying to run a race that can’t be won because the race doesn’t even exist, which I know sounds a little bit out there. But it is true that you can’t prove your worth by doing anything because you are simply worthy as a human, regardless of what you do, which is not something that I was necessarily used to. There are some tangible signs that you might be in that category, like burnouts, although, right in this moment, in our world’s history, burnouts stem from many different reasons. But yeah, the burnout piece, or if you are staying in a job that you don’t like or working with a client you don’t really want to work with because you are ‘successful.’ Or that you are getting external validation, and the world’s definition of success that’s been handed to you, but it doesn’t fit who you are. That all falls under this category of the overdoing, overachieving, where you’re tying your worth in some way to that external achievement.”

How Can You Overcome Overachieving? The First Step is Redefining Your Definition of Success

It sounds like understanding how you personally define success is an important part of this work. So, I ask Heather if she has any recommendations on how someone could start to identify their own definition of success. She shares that by creating space, you can ask yourself questions to know what rules you are playing by. Is your definition of success something you have been taught? Did your parents define success and failure, or perhaps your teachers and bosses? Even as entrepreneurs, we are constantly getting messages about what a successful business is supposed to look like, and as Heather points out, it’s always bigger and better. 

“Bigger and better may be right for you, or it may not be,” Heather says. The first step in defining what success means to you is unraveling what it doesn’t mean to you. And to understand the definition you’ve been given and sift through what part works for you and doesn’t. Because it’s not about throwing it all out the window. It’s about looking at it and saying, of what was given to me, or what I’ve learned over the years, what still holds true for me now, and what doesn’t? And then I think, asking those questions of what do I really want? What do I desire? What do I want my life to look like? What’s the impact that I want to have through the work I’m doing in my day-to-day life? And yes, those are big questions. And I will tell you, particularly as women, we often aren’t taught how to ask ourselves those questions like, what do I want? What do I need? We may be taught that it’s selfish to ask those questions or follow through on what we want and need. So, asking yourself, even in little ways, like what do I want today, can help you to start to uncover what’s important to you in the broader scheme.”

I think this is really challenging in this day and age with social media. There have been many times in my business where I’ve scrolled through social media and started to compare my business and where I’m at to someone else. And this is such a problem because I don’t really know what I’m comparing myself to! I’m comparing myself to this image that I see in this perfect post, but I don’t know the background. So, I appreciate how Heather asked questions to help us understand what we have been taught about success and then explained how to unravel what it truly means for you. I was taught success was earning a lot of money, driving fancy cars, buying Rolexes, and living in this big house. So, it’s essential to pause and ask, is that what I want? Is that how I define success? 

“And, of course, your happiness comes into this as well,” Heather adds. “Like, what do you find fulfilling? What makes you happy? And not just happy on a surface level, but that real joy, and experiencing joy and pleasure and purpose in life? And I will tell you, especially when I first started my business, I felt the same way about comparison. I felt so behind. In every part of my business, even though I was in year one, I still felt behind from where I was supposed to be. I had this very strange notion that I needed to match my corporate salary in a year, which did not happen. I just had this built-up expectation or standard in my mind that wasn’t true. I don’t know where it was coming from, these messages are all around us, but sometimes it was provoked by very specific people, and not in a way where they were trying to provoke it. I will tell you, a while ago, I went through and quite literally unfollowed all of those people, some of whom I know and respect. I was like, I’m not gaining anything from this, it’s making me feel behind in a game and in a race I don’t even want to be playing in. And so, let me just exit myself entirely because I can’t control all the messages coming to me. But where I can, let’s take control and take it off of the board, so I’m not getting those messages in the first place.”

Heather mentioned something so important by asking, is it a game I even want to be playing at? That was me last year when I told myself this story that the only way to scale my business was to create a course. I thought I needed to create a course and have a launch plan. And I studied, and I looked at all the influencers. And let’s be clear, I am not an influencer. That is not my role. I am a coach; I help people achieve their goals. But I totally went down that comparison rabbit hole and all the “shoulds,” which is probably also a sign that you are overachieving if you’re focusing on the should. Heather agrees and explains that “shoulds” are not only about overachieving but that they also come from the rules we are handed. And much of that includes bias for women and the idea that we should put others before ourselves or that we can’t say no or disappoint anyone. There are also messages that we should be productive all the time. Those indirect messages over the course of our lifetime can start to build a narrative that our value is in working hard and being liked. Heather explains how when we evaluate the rules that have been handed down to us, we can start to decide if we want to keep playing by them.

That was an important part of Heather’s book that I connected with, this whole concept around rules. Before reading the book, I don’t think I realized that I had all these rules. And sometimes they are really silly rules, such as it doesn’t count as a 30-minute Peloton ride unless I hit a 200 output. Why is that a rule? It is not in the Peloton user guidebook. I ask Heather how we can identify these rules and then learn to break them.


So, How Can We Break Our Own Rules as Overachievers?

“The ‘should’ is always a really good indication of a rule,” Heather says. She explains how a should isn’t always negative, but it’s when accompanied by “always” that it can indicate a rule we are following. She shares an example of when she was in the process of moving and stayed with a friend for a few months to avoid having to sign a lease. “I talked to my parents about this move,” says Heather. “And I said, you know the other nice thing about moving in with my friend is I’ll save some money. And my dad looked at me and said, it’s always good to save money. And I thought ding, ding, ding, ding, ding. That is a rule I’ve been taught that’s probably true 80% of the time, but not the other 20%. And I will tell you, as a business owner, I have really had to learn how to spend money because I was taught that rule growing up, that it’s always good to save money. And so that “always” was an indicator of a rule that I’ve been taught.” 

Heather shares how rules can become beliefs regardless of where they come from, such as literally out of someone’s mouth or through social media messages and other things around us. And those beliefs may or may not be helpful to us, our business, or our communities and world. I ask Heather how we can start to break a rule once we become aware that we have created and are following it.

“This is such a great question,” says Heather. “And so, part of it, I think, is then creating new rules. So, for example, mine is, you know, I had all these rules around, I have to be productive all the time, even though I always loved fun too. So, I never had a problem having fun. But I would feel this pull if I was just relaxing and doing nothing, back to my computer or back to work. And I would say it was even worse when I started my business because it really is all on you to a degree as an entrepreneur. And especially when I was in that phase of, I don’t know what I’m doing. I have no clue what my business is about, and I need to make money. I was putting an undue amount of pressure on myself. And so, I started examining. I finally stopped and said, why am I doing this? Why am I working so hard and overdoing things and putting all this pressure on myself? And for me, the answer came immediately, which is, I’m doing it to prove myself, to prove my worth, which goes way back to these rules related to high school and weight and dating and all these things that are really deep for me. And so, uncovering those rules that I was following, and then saying, no, I want a new rule for myself. I want the rule that I am worthy for who I am, not what I do. And that was the rule that really stuck with me. Other people have rules like, I can be responsible without taking responsibility for everything. Or I can care without caring about every single detail and taking responsibility for it. So, once you identify some of these new rules, they can sink in over time. It can be an act of reflection, or you can see what arises that really resonates with you. And then start acting as if you believe those rules, even if they are uncomfortable, even if you don’t fully believe them yet. And this leads to one of two things. So, one is you take action if it’s a more concrete rule like I don’t have to be responsible for everything. I can care without taking responsibility for everything. You take action based on that. And you realize, oh, I don’t actually have to be responsible for everything. Things work out most of the time. Other people step in and take responsibility. Everything didn’t fall apart. And it reinforces this belief, and you’re creating a new story in your mind. The other side, like you can’t really ever prove your worth. But if you start acting based on the fact that for me, I’m worthy for who I am, not what I do, even though there wasn’t concrete evidence of it out there, there is with letting go of responsibility. The story still sunk into me over time. And I realized over the course of months, maybe even a year, that I actually really did believe it. And interestingly, you brought up the course thing a few minutes ago. I also thought I needed to have a course. My most popular speaking topic was imposter syndrome and what to do about it. So, I was like, well, great, let’s create an imposter syndrome course. And I love courses. I mean, this is what I do. I’m a speaker. So, I had no issue creating the course at all, but it was the marketing side. So, I hired a digital marketer who tried to put it out there to all these things on Facebook that I will tell you I didn’t really like. I loved designing the course, but I didn’t love anything else that had to do with it. And the entire thing failed. Literally one person signed up for this course. And I almost didn’t care. I was a little disappointed. I was frustrated with the money that I’d spent; that was certainly true. But I didn’t feel like a failure. I was like, oh, this course failed. But I’m not a failure. And it was really the first time in my life that I felt quite detached from the outcome. I could learn from it. But I wasn’t sucked into the outcome as a person. It wasn’t a reflection of me. And that was the first time in my life, especially my business, that I noticed that, and I was like, oh, that’s because I now believe this. And because of that, I can experiment, try new things, and have things fail. And it’s okay.”

One of the rules that Heather pointed out in the book that I underlined is, “I carry all their details and emotions in my head in a way that most male coaches I know simply don’t. They just let it go.” And I find that to be true. I’m constantly reflecting and ruminating and thinking about my clients. And many of the clients that I work with care a lot about the people they serve as well. Because of that, I ask Heather, how can we better let it go?

How to Let It Go

“It’s such a good question because empathy and connection are good,” says Heather. “Research says that women carry a higher emotional and mental load than men do. And I am a single non-mother. Mothers do this even more. Women are the ones who remember it’s dress-up day at daycare. And, of course, this doesn’t go for every woman or every man or every relationship. But if we’re talking about cisgender, heterosexual relationships, even those that are equal on paper, as far as how duties are being split up, it doesn’t end up being equal from an emotional and mental load perspective. And that’s where this comes in. And it’s because of that bias and those rules that we’ve been handed saying that women are supposed to take care of everyone and put everyone above them. That’s where this mental and emotional load comes from. So, part of deconstructing that is deconstructing the rules that you don’t have to be that, that you don’t have to take care of, and have responsibility for, every single detail out there. But I think part of it, too, is determining what of this do I like, what’s helpful, what’s beneficial, and what’s not? Because like I said, empathy and connection are really good things. Caring about people is good. We need more caring and connection in our world. But the overdoing or feeling like you are responsible for other people’s emotions is not particularly helpful. The other piece that helps me to let go is finding those activities that help me disconnect. So, hiking is one of my biggest things, no matter what’s going on in my head. If I go out for a solo hike and get out on the trail, everything’s good in about five minutes. It allows me to disconnect completely, let go of any ruminating thoughts I have, or sort through things and just let it all go. So, I think finding out what those activities are for you. And for some people, it’s sitting there and doing nothing, sitting quietly for a few minutes and taking a deep breath. For some people, it’s an active release, and for others, it is a community that helps you to let go. It’s different for everyone. But knowing what helps you is beneficial.”

I found myself crying in yoga this past weekend. And I thought what the heck is that? I’m literally in child’s pose at the start of the class, and tears are coming out of my eyes. That must have been an active release of things I’m holding on to, and of course, I’m reading Heather’s book. So, I’m probably working through all of my own inner critics and everything.

“Tears are such a huge release,” confirms Heather. “And sometimes we know why we’re crying, and there’s a very concrete reason. But other times, it’s exactly what you said, like I was just sitting there. And I’ve also found that particularly for women like us who tend to be moving a lot and always going and always working hard, emotions can come up if you slow down. I’ve felt that myself, that a child’s pose, sitting on the couch, or even a slow walk, can bring up emotions. I’ve had coaching clients tell me when I slow down, I start to cry and I’m not even sad, I don’t know what’s going on. And it’s just a buildup of emotions inside of you that need to be released. So, I think of it as a very healthy thing. And, of course, if anything ever feels like too much, that’s a good sign to reach out to a therapist or someone that can help you through those things. But crying is a release, and it’s a good thing.”

This leads us to talk about manic mode, which is this space where I feel like I’m constantly going. I talk fast, walk fast, and am busy, busy, busy. I feel like I’m in manic mode a lot.

How to Identify When You’re in Manic Mode (and How to Get Out of It!)

“Yes,” says Heather. “So, how do I define manic? This is a term I made up. If you Google it, you probably will not find it. And I want to be very clear, I’m not talking about manic mode as it relates to an actual mental health condition. This is something more where I feel somewhat like you were just describing Kristin, like, I’m moving faster than I really need to. And sometimes that is a physical movement like rushing through the grocery store when I don’t need to be rushing through the grocery store. And sometimes, it’s a mental pace where I feel like my brain is kicked up a couple of notches from where it needs to be. And sometimes that can be helpful, like when we want to move fast through things and connect all the dots all the time and go quickly. But it’s not how our bodies were meant to operate day-to-day. We’re actually designed to be slower most of the time and then have these huge intermittent springs essentially. But today, most of our world is designed where our entire body is amped up more than it needs to be. So, this is that manic mode. When I first realized this, I think I was quite literally returning something in Kohl’s, and I was like, why am I moving this fast? I don’t need to be rushing. And when I notice that now, I just stop and take a breath and remind myself, I’m not actually in a hurry. And even if I am, the ten seconds I’m going to save by moving my body faster is not actually helpful at all. And then when I stop and take that breath, often physically slowing myself down will mentally slow myself down as well. So doing those things like taking a breath, taking a slow walk, laying on the floor, whether you’re actively meditating or just lying there, all of those things can help you move out of manic mode.”

So, this is probably why I have felt compelled to meditate more. I have not done a great job of building past a five-minute meditation. But even laying there for five minutes is helpful. Heather confirms that yes, five minutes is long enough for our brain to slow down. While we have a lot of undue expectations on what meditation is supposed to look like, Heather reassures me that whatever creates space is good, whether it is thirty seconds or thirty minutes. 

I want to talk about the inner critic and true inner voice. In many of the coaching conversations I have, we need to unpack some of the stories and the limiting beliefs keeping us from reaching our goals. So, I ask Heather to explain the difference between the inner critic and the true inner voice.

How to Differentiate Between the Inner Critic vs. the True Inner Voice

“The inner critic, I mean, to a certain degree, is just what it sounds like,” says Heather. “We all have it. Even if you haven’t heard that term before, it’s that inner mean girl telling you you’re not enough, you need to be working harder. You always need to be doing more. Anything you’re doing isn’t good enough. Maybe you hurt someone’s feelings, or you should have asked for more money or less money. I mean, all of the things, right? It depends on the person what your story is, and of course, the situation as well. But the inner critic really is circular. Often, it’s ruminating up in your head. And the interesting thing is the inner critic is trying to protect you so we can treat it with some compassion. It’s trying to protect you from embarrassment, shame, things like that. But at the same time, it’s doing its job a little too well. And it can really keep you small by listening to the voice of that inner critic. And that voice oftentimes comes from those messages, again, going back to those rules we’ve been taught or past experiences. Or, maybe something wasn’t perfect and you got called out for it in a pretty humiliating way. So, your inner critic does a lot to protect you from that feeling again. The true inner voice I consider to be the core of you. You can call it your soul, your inner mentor, the future self. There’s a lot of different words that you could use to describe that true inner voice. There is a spiritual or religious connotation to the true inner voice for some people. For other people, there’s not at all, but it’s really the core of who you are. I also like to compare the heart voice to the head voice or the body, and what your body is telling you, your intuition, all of those things are your true inner voice. And the problem is, the true inner voice is very strong, but it’s not always loud. Especially when we aren’t used to listening to it, or it’s kind of been trained out of us not to listen. Because sometimes the true inner voice wants you to do things that are not particularly logical. And our world tells you, you should only do the logical things, the things that make sense on paper. And I will tell you, I have no problem with logic, but I’m probably pretty evenly split between logic and intuition in how I make my decisions. But I also know that when my true inner voice is really clear and telling me I need to go do something, it’s never steered me wrong, even if it doesn’t make sense on paper. So, a year and a half ago, I moved to Colorado just because I wanted to. And because I felt called to move here, it was really that true inner voice telling me you need to do this. It made no sense on paper. My business contacts are in Minnesota. And yes, we’re in the middle of the pandemic, which temporarily made it easier to move, but I didn’t know what that would look like long term. I enjoyed living in Minnesota. It’s where I grew up. But the second I got here, I felt at home, and there has been no impact on my business. In fact, my business has grown substantially. Similarly, in my business, for the first couple of years, I did what everyone told me to do in my business. I was listening to the experts out there. I was following all their rules. And yes, I learned a lot from that. So, I don’t regret trying all those different things. But my business took off when I took that step back and was like, what actually works for me? What’s my intuition telling me that I need to be doing? What makes me happy? That’s when my business actually got successful. I could parse out head voice versus heart voice, the inner critic ruminating versus that soul and what is really right for you. Your body also plays a role in this. What are the messages your body’s giving you about the decisions to make? And what’s right or wrong for you?”

I ask Heather how we learn to listen to our inner voice more than that inner critic. And she responds by saying we have to create space. She explains that she has discovered just how important it is to have space to hear yourself think. Journaling can help with a little bit of structure and prompts, such as what I’m really longing for is… or what I’m feeling right now is… Setting an alarm for five minutes and writing continuously can help uncover something or act as a nice purge. Either way, Heather reiterates that we need space, quiet, and time to hear ourselves, not just the voice in our head but in our heart. 

I highly recommend getting a copy of Heather’s book, An Overachiever’s Guide to Breaking the Rules, and ask Heather where our readers can go to learn more about her and her work. She recommends her website, where she has information about her speaking, and her blog. You can also order signed hardcover copies of her book there. She also recommends LinkedIn as the best social media platform to connect with her, although she is also on Instagram

With that goal achievers, keep celebrating your weekly wins, noting your lessons learned, and identifying your priorities for next week so you can consistently pursue progress in the direction of your goals.