TCC Podcast #252: Finding Courage with Heather Hubbard - The Copywriter Club
TCC Podcast #252: Finding Courage with Heather Hubbard

On the 252nd episode of The Copywriter Club podcast, we dive deep into courage with Heather Hubbard. After some unforeseen events and challenges, Heather shifted from powerful lawyer to powerful CEO of Simple Courage. Heather describes Simple Courage as more than a mantra but a mission and movement to both individual and collective change.

Here’s how it all goes down:

  • Why the drastic shift from lawyer to Simple Courage movement.
  • What to do when we can’t get ideas out of our heads.
  • Making major shifts and strides in the middle of a pandemic.
  • Dealing with dysfunctional relationships and tragic life events and moving forward.
  • Saving face and not being true to one’s self.
  • The standards that are set by society and how to break them.
  • Why being uncomfortable can be good and bad.
  • How to choose or recreate your own stories.
  • The 4 types of courage and changing between each.
  • The difference between fearlessness and courage.
  • Showing up brave because you have to rather than wanting to.
  • How to figure out why we’re afraid of something in the first place.
  • Why it’s important to stay curious and color your hair pink.
  • Things we let slide because we think we’re being brave.
  • Leaning into your values and taking a stand for what you believe.
  • What we are actually afraid of happening when we have Simple Courage.
  • How Simple Courage can work in your favor if you allow it to.
  • The everyday effects of the different types of courage.

Listen to the episode or read the podcast for inspiration on stepping into your own power.


The people and stuff we mentioned on the show:

Kira’s website
Rob’s website
The Copywriter Club Facebook Group
The Copywriter Underground
Tamara’s website
Simple Courage website
Simple Courage podcast
Heather’s program
The Alter Ego Effect by Todd Herman


Full Transcript:

Rob:  What does being courageous mean to you? Is it being brave enough to run into a burning building to save someone? Is it standing up for what you believe in, or maybe standing up to protect others? Most of us grow up with the idea that courage is a good thing to have, but we’re not always courageous in the things that we do. Our guests for the 252nd episode of The Copywriter Club Podcast is Heather Hubbard. She’s the founder of Simple Courage of movement that is helping people embrace courage and change their lives, and we think that you’re going to like what she has to share.

But first, before we get to that, Kira is still on maternity leave. This is starting to feel to me like the never ending maternity leave. So I have my special guest hosts to help with some of the comments on this episode, Tamara Glick. Tamara is a copywriter, brand stylist, brand voice specialist, and so many things. She helps us with some of the stuff that we do in the think tank. Tamara, welcome to the show. Thanks for being here.

Tamara:  Thank you so much, Rob. Man, oh man, I am so excited about this conversation. This is the deep meaty stuff that I love. Forget the small talk, tell me about your biggest fear and your deepest secret, I’m a vault. That’s everything I want to know. So thank you so much for having me back for this one, Rob.

Rob:  You’re not getting my deepest secrets, but we’ll be talking about some other things on the show.

Tamara:  That’s okay.

Rob:  And also just as a reminder, Tamara has actually been on the show as a guest before, that’s episode number 142 of The Copywriter Club Podcast. If you want to listen to what she shared there, all about like style, copy style, all of that stuff. It was really good interview, so check that out. Before we get into our interview with Heather though, I’m going to switch things up a little bit and instead of telling you about The Copywriter Think Tank, which of course is still available.

If you’re interested, go to, but next week we are opening up The Copywriter Accelerator, and this is our 16-week program. We only do it twice a year. This is the last time that we’re doing it this year. It opens up next week. It’s eight modules, talking about things like mindset packages, processes, pricing, branding, getting yourself in front of the right clients, x-factor, all of the things that lay the foundation for a successful business.

It’s not a course, it’s a program that you go through with a community of other copywriters and as we’ll be sharing in the free Facebook group and in other places, there have been some amazing copywriters who’ve gone through that program and just done really incredible things with their business. And so if you are interested in hearing more about The Copywriter Accelerator, go to, get on the wait list. This next week there’ll be a webinar all about pricing.

The webinar is free, so you can check the data out, learn a little bit more about the accelerator and see if it’s a fit for your business. If you’ve done anything with us before, you know that Kira and I are into the hard sell thing, but we will tell you the information you need to make decisions, see if this is right for you. So go to

If you’re listening to this between August 24th and September 1st, the doors are open, so you get yourself in there. If it’s before that, get on that wait list. And if it’s after that, sorry, you’re going to have to wait until next year. So here we go.

Okay. Let’s jump into our interview with Heather, with her story and ask her how she became the founder of Simple Courage.

Heather:  It’s a really long journey and a really long story, so I’ll try to keep it brief. I was going through a lot in my life at a point in about, I don’t know, 2011, 2012? And I started on this journey of really trying to discover who am I? What am I here to do? And why is my life a complete mess? It looks great on the outside, but inside, internally it’s a mess. And so it was on that journey that I really had to start looking at my own fears. And it was during that time that I discovered the concept of Simple Courage for myself.

And I thought, “Oh, that’s really brilliant.” It was one of those like moments, those like aha lightning moments where I was like, “Oh, this is good. This is really good. This is not just for me.” And so I wrote it down, I got a Sharpie and I got a post-it note out and I wrote down, Simple Courage. And I posted it up on the wall in front of my computer and my desk because I knew that it was really, really good and it needed to be shared with the world.

So I just looked at it and sat on it for, I don’t know, five, six years, because this is what we do when we’re afraid to bring something to the world. I thought it was too big for me, too big for my voice. Recently I was a lawyer, I was a partner at a really large law firm. I was a strategic coach and consultant, and so I thought everyone wanted my brains, and my strategy, and my advice, and that’s how I would monetize my life.

I wasn’t sure that I could actually bring a mission, a message, a movement to the world. And so it literally sat up on that wall. I kept just looking at it for years and years and years. I guess I was slowly doing just little bits and pieces with it. And in May of 2019, I decided that I was really going to develop a keynote around it because I was already doing a lot of public speaking, and so I did that.

And then in May of 2020 during the pandemic, I decided I was going to stop the podcast that I had, Hustle & Flow and move to Simple Courage. And the pandemic really did a number on my business. I used to do really high in masterminds, coaching consulting, and I knew I had to pivot. And I was like, “Well, if I’m going to pivot, why not go all in on Simple Courage?” And that’s when you and I started working together fall of last year, and here we are.

We’re recording this now in May of 2021 and we’re about to do our founders launch. So it was a six-year journey.

Rob:  Heather, when you said your life was a mess or whatever, tell us a little bit more about that. What was so messy? Because being a high-end attorney, leading new masterminds, whatever that sounds pretty great. So what was the mess?

Heather:  The mess was that I had a lot of really dysfunctional relationships personally, with my husband, with friends, with my family, with my colleagues, with my bosses. And what I mean by that is I was very much a people pleaser and I didn’t have very good boundaries at all. And quite frankly, I let people walk all over me. I don’t think I realized I was doing that, but it was pointed out to me from a therapist when I was doing an intervention with my husband. There was a year when literally everything in my personal life seemed to be just going wrong.

My husband was an addict, I had been covering that up for years. My sister died that same year. I was in a walking boot for eight or nine months that year, because I tried to run a half marathon and had a stress fracture. It just seemed like everything was going wrong. And so I was showing up in the courtroom, I was showing up in board rooms being big and brave and fighting, and yet behind the scenes, it just seemed like my life was… Like I was a fraud, like I was a complete mess in so many different ways and yet no one had a clue, no one had a clue.

Kira:  How do you come back from that? What are some steps you take when you realize things aren’t aligned and I’m showing up one way, my life has a different way? What happened behind the scenes to get to you to the point where you were able to make those bigger life changes and business changes?

Heather:  Unfortunately I feel like everything had to fall apart for me to be ready to actually make a change. And I would love to say that I saw it coming or I was being proactive. The truth is I really do feel as though I fell hard on the floor and was like, “Something has to give. There’s something wrong and I don’t even know what it is, but I know that I need to seek out answers.” And so for me, it was really organic, I just started seeking.

And that’s the only word I know to use for that, I just started seeking. And so I started exploring anything and everything, consuming a lot from different types of therapies to reading books, yoga, meditation, retreats, EMDR. I feel like I just immersed myself in anything and everything and I was just open to, there must be an answer out there. But even that in itself, that was a journey, and what I found was there is no answer.

I really was looking for that how to book, that formula, that checklist and it didn’t exist, unfortunately, because that was my preference. Just tell me what to do and I will do it.

Rob:  The perfect checklist didn’t exist, but you created this formula for yourself. Tell us a little bit about what Simple Courage is. What does it mean? What does that look like?

Heather:  In many ways, it’s not even a formula, it’s something I’m still discovering. Simple Courage for me… So many people had always told me that I was courageous and that I was fearless because they saw my outward appearance. And in many ways it was true, because often I am fearless in business and there’s just no fear there. And so it looks like I’m courageous, but I’m not really, but so many people used to say that to me.

And so I started to think, “Well, if I’m courageous in these areas of my life, then surely I can find a way to be courageous in these other ways as well.” And so I really started to explore my relationship with fear and the way that it was showing up in my life, because so many people had always told me that I didn’t have fear that I thought I didn’t, which wasn’t true at all, I did have fears.

But it turned out that as I peeled back the layers, I realized that all of my fears were wrapped up in not being enough, disappointing people, not being worthy enough. It really related to all of these roles and expectations that others had for me and that I had for other people. So it was just this fear of never being able to live up to my potential or to live up to expectations.

And it was in that process that I started to become open to the concept that what if everything that I had told myself was wrong? And what if everything that others had told me was wrong? And a lot of this came from mindfulness concepts, a lot of this came from 12-step concepts. And I was like, “What if courage is not this like extraordinary running into a fire or going out and leading the charge in some business setting or activist setting? Maybe it looks a little bit more subtle than that.”

And for me, it was taking small steps. So each and every day, I was just getting a little bit more uncomfortable with what it looked like to show up in a way that felt true to me, but that the world was telling me was wrong and inappropriate. In many ways, it almost took me out, because I didn’t have a support system, I didn’t have anyone trying to help me move through that, and it’s really hard to be uncomfortable.

We say that it’s not a big deal, but it’s a big deal. And so it’s really not a formula for me. It’s really about just being open, being curious to exploring where did these stories come from? And do I want to choose a new story? And if so, what does that look like? And am I willing to take a small step and being a little bit braver in a new area each and every day? I suspect that I will be exploring and learning things about myself with Simple Courage until the day I die, whether that is tomorrow or I’m 111.

Kira:  Can you talk us through the different types of courage or just how we can think about it? Because I feel like since learning from you and working with you, it’s changed the way I look at courage too. And I feel like you’re really good at talking about the different perspectives we can take, so we have that awareness.

Heather:  In my mind, there are four types of courage and one is not really a type of courage, but I think we think of it in that way, so it’s worth talking about. And the first is fearlessness, so I was referring to that earlier. A lot of times when we think of courage, we actually think of fearlessness because we see someone doing something that we wish that we could do, but we’re afraid. When we think about fear and fearlessness, it’s really about the actor and not the act.

Some people are not afraid of jumping out of an airplane and others are. Some people are not afraid of public speaking and others are. So it’s not that the thing is scary, it’s just what you perceive. So if you do not perceive something as scary, if you’re not afraid, then you don’t actually need courage because you are fearless. That’s the first category. The second category is extraordinary courage, and in my mind, this was what I had always really thought was courageous. It’s what we see in movies and it’s what we hear about as children.

They’re firefighters, they’re police officers, they’re often in the military, or we think of like brave heart or someone like really going to battle. And even if it’s not physical, there’s still like some life-threatening situation there where it’s like really, really scary and you might die. And few of us are ever really called to show up with extraordinary courage, and oftentimes we think, well, that’s not me. But that’s not really the standard. That’s extraordinary courage.

The other two types of courage is really where I think we spend most of our time, and one is simple courage, and one is false courage. They are indeed the everyday courage that we tend to turn to when we’re doing uncomfortable things. Most of us rely on false courage. False courage is when you are scared, you are uncomfortable, but you show up as brave and you really do have to muster up courage, but you’re doing it because you think you have to.

You’re doing it in order to get the approval of others. You’re doing it because that is the role and the expectation for you. And it is the kind of courage that in many ways helps us build successful careers. And so we don’t think there’s anything wrong with it, except it often will take us out. It leaves us feeling completely depleted, exhausted, resentful, frustrated, and feeling as though there is something missing or there is something wrong.

Simple courage on the other hand is showing up, again, you’re scared, you’re uncomfortable, but you must rep the courage to show up in a way that is true to you. And there may be criticism, there may be backlash. There may be repercussions for showing up with simple courage, and it’s why so few of us want to rock the boat. It’s easier in so many ways. It feels easier to show up with false courage because we are rewarded by others for showing up in that way.

But the problem is, it is often a life or death situation, not physically, but emotionally. It’s like a life and death situation for our soul. This is where we can go days, months, years, or we’re at the end of our life and we’re like, “Whose life did I just live?” And it was because we were so worried about what others would think of us, and so we just fall back into that false courage pattern.

That’s the mission behind Simple Courage is helping people see that you don’t have to live life that way. There is a better way that may feel more uncomfortable in the moment, but the more you do it, the easier it gets and the results are so… they’re more lasting in that like you have more fulfillment and you’re more satisfied with who you are at the end of the day.

Rob:  As you talk about the different kinds of courage, as I think about it, I can think of some situations where it’s like, okay, maybe I need to be more fearless or maybe I need extra ordinary courage. And there’s others where simple courage is needed. But I guess the real question is how do I get started? If fear is holding us back or something else is holding us back, how do we take that first step into courage?

Heather:  I really think in so many ways, the answer is curiosity. As a lawyer, I was trained to be highly critical and judgmental. But I think we’re like that as a society, as a whole. We’re born into families and educational systems, governmental systems, religious systems that teach us that there are rules. There is right and there is wrong, there is good and there is bad. And so if you want to be more courageous in your everyday life, you have to be open to looking at why you’re afraid in the first place.

Just getting really, really curious as to where is this fear coming from? And what am I afraid is going to happen? And you’re going to probably start to discover that you were taught things as a child that relates to your values and your morals that you never… It’s not like you developed them, you simply inherited them. And they are so ingrained in us and taught that when we go to challenge, so if we’re curious and we see that.

And then we’re curious about, well, what would happen if I challenged that? What would happen if I did something different? That’s when we start to write… the fear will like hijack our brains and our bodies and we were like, “I’m going to die. I can’t do that.” And so just being curious as to, well, what is that about? It really does open your eyes to see just how strong the grip of fear can be.

And then when you start to think about the fact that it’s just a story that’s been told to you, it can change your relationship with how you see it. And then just getting curious with trying things out. You don’t have to go all the way. If you’re really, really scared about trying something, you’re like, “Logically, I get it. It’s not that big of a deal. Logically, get that if I dye my hair pink, it’s not the end of the world, but we might think it depending on our family, our industry.”

And so it’s like, “Okay, well, maybe I don’t have to dye my hair pink tomorrow, but what would be something like a smaller step that I could take that still makes me feel a little uncomfortable, but isn’t going that far?” And when we stay in that place of curiosity, both in exploring where these stories come from, as well as being able to take small little steps to play a different role or to be a little bit more courageous, it makes it more doable and doesn’t have to feel so heavy and so cumbersome.

Kira:  That makes me want to color my hair pink just when you talk about it, or maybe just starting with like a little strand underneath here. Could you share the examples… I know we talked through the four types of courage. Can you share an example of each? Extraordinary courage, we get that, it is a firefighter, but can you give your own personal examples for fearlessness, simple courage, false courage, and make it a little bit more real to all of us?

Heather:  Sure. Let’s see. Fearlessness, I’m not afraid of a microphone. I love a microphone. Anyone who’s ever like, “Oh, do you want to be on the podcast?” The answer is, “Yes, please,” because I love to talk. Seriously, give me a microphone and I come to life, so I am fearless with that. Whereas I know some people, they get really worried. They want to prepare, they want an agenda and I just want to have a genuine conversation. So I am fearless when it comes to speaking in that sense.

An example of false courage for me, I still show up with false courage, but less and less because I try to be so aware of it. But when I was in law firms, especially and I was a manager in the law firm and I wanted to be successful. I was often the only female in those rooms. There were a lot of inappropriate comments that were made. There were a lot of sexual comments that were made. I remember you’d walk into an office and there were guys and they were joking around and they might be looking at a Playboy as they’re drinking whiskey and I wanted access to those rooms.

And so I pretended as if those things did not bother me. Not only did I not say anything, I didn’t even let it show up on my face. In my mind, I thought I was being brave and courageous, when the truth is I wasn’t really being brave and courageous at all, because it was not aligned with my values and it did make me feel uncomfortable. The flip side of that, an example of simple courage would be when you do speak up.

And I did get to the point where I started being an advocate or I started saying like, “This isn’t okay because if you’re sitting here looking at a Playboy, then that tells me that you objectify women. And the fact that you guys are sitting around here together, in an office setting, not in your own home, a private setting, doing your own thing. Then it makes me believe that the reason why we don’t have women at the top of the company is because you don’t actually take women seriously.”

I started to have those conversations and indeed I got feedback once of like, “You push the women’s issues too much.” I potentially could have lost my seat at the table. They still allowed me to be there, but that would be an example of simple courage for me. It was standing up and speaking up knowing that I might get kicked out.

Rob:  I think we’re getting to that in some of the examples that you’ve shared, but let’s talk about some of the benefits, the results that happened when we really do step into courage. It’s not just about having a seat at the table or keeping the seat at the table. It’s not just about being able to jump out of the airplane. Where does it get us?

Heather:  I can share where it’s gotten me and it always amazes me to see others results as well. But for me, simple courage, a lot of it, at least right now, so I’ll speak in the context of right now. It relates to activism, and so I have been speaking up a lot more on social media. Even in developing Simple Courage, we were trying to decide, how much of this do we want to be open and honest that we are a brand that is here to bring down the patriarchy? And we are a brand that is going to be very, very vocal about our beliefs related to social justice and to change?

That took simple courage for us because we were taught to believe that if you take that strong stand, you’re going to lose business. And indeed, when I started taking that stand, we had clients upset. We had clients reaching out and we had clients asking for refunds. And the interesting thing is we always… Our number one value had always been, we believe in a world that is equal and we don’t shrink from disbelief.

And so, we had so many podcast episodes related to racism, and diversity, and things like that. So it really shouldn’t in our minds have been shocking to others where we stood on issues, but we came out and said them in, I guess, an even more direct way than ever before. And we were worried like is that even the right approach? Because we do believe that everyone needs to come together and at the same time, we’re not willing to make room for people to come in and argue that all lives matter.

And so we’re continuing to each and every day work through that, but here’s the interesting thing. Yes, we lost some customers. Yes, we had people that were upset and we had even more people reach out to us via email, via private message to say, “Thank you so much for taking a stand. Thank you for being so courageous. You are modeling behavior that I want to. I want to be able to be more outspoken as well, but I’m worried I’ll lose business and I’m not quite where you are, but thank you so much for showing us what’s possible.”

One of the rewards of living into simple courage is that you start to see that you’re going to get aligned with the people who matter anyway to you. You’re going to attract the relationships that matter most and you’re going to lose some people, but you’re going to gain others. And life is going to be so much easier when you’re working with people who do share those values with you. And it frees you up to speak more.

If I have one conversation that feels really uncomfortable, well, the next time it’s not as scary. And so then I go even a little bit further, and a little bit further. And before you know it, you’re just comfortably having conversations that may be a week, a month or a year ago you were afraid to have at all. That’s one benefit, but the thing is, it’s like I sleep better at night. I don’t have to pretend, and I don’t have to fear or worry about where the country is headed when I know I am rooted in my truth and speaking my truth, such that I know I’m making a difference.

Now, for me, that’s that’s activism, but for other people with simple courage, so I’m thinking of some of the betas that we did earlier this year as we were trying to develop. Because it’s like, “Okay, that works for you, Heather, but is it going to work for others?” And we had so many amazing examples come out. We had one woman who had not spoken with her father in over a decade, and they started to have a courageous conversation and mend that relationship.

We had another person who really started to address the grief of a family member who had been sick, where they had just jumped straight into problem-solving mode, that they didn’t even realize that that was standing in their way. We had someone else who shared that in the moment as she was having a conversation with her mother and her daughter, they realized that they were passing on social conditioning that they didn’t even realize they were doing.

They were feminists, they want to dismantle the patriarchy and yet they caught that they were actually passing along social conditioning that had been passed on to them and being able to be aware of that, and catch that, and stop it in the moment. We had someone else who had some mental illness in their family and they hadn’t been addressing it because of the stigma, and they were really concerned about what others would think.

And the most interesting piece, at least to me, with all of that is when people came in to explore some of the Simple Courage work and the beta, what they thought they were going to explore were things related to business. Like being courageous either in business or activism and turned out, they found that there were other areas that they had been ignoring, where they needed to be more courageous.

And as they explored those areas, they realized that they naturally started to become more courageous in their business as well without actually having to address that issue head on. Everything is just so nuanced and complicated, and so it always just blows me away where other people’s journey through Simple Courage takes them.

Rob:  Let’s break in here and chat about a couple of things that Heather’s talking about. Again, Tamara, you’re the perfect guest host for this episode, because I know this is the stuff that you really, really groove on. But let’s talk about courage. How do you practice it? What is it that stood out to you as you heard Heather sharing the four types of courage?

Tamara:  Oh my goodness. I think first of all, one of the things that goes through my mind as I listened to Heather talk, and as we think about the concept of courage is The Wizard of Oz. How can we not think of that? The Cowardly Lion and how he musters up courage and how we all are challenged with mustering up courage in different ways, at different points in our lives, in different situations in our lives. That, It’s just to me an indelible way of thinking about what it takes to become courageous in different ways and how something that seems so simple can be so challenging.

But when I think about the four types of courage, it’s just an amazing framework for life, really. Fearlessness, extraordinary courage, false courage, simple courage, do we not all require each of these four types of courage in some measure or another at different times of life? And the intersections of curiosity, fear and bravery, it’s really where all the good stuff lives. Isn’t it?

Rob:  I’m going trust you on that. Yeah, of course it is. Of course it is. As I was thinking through this, what courage really is and what it’s not, there are all kinds of examples where maybe we think we’re being courageous, but we’re actually hiding. And it’s actually the opposite thing that would be the courageous thing to do. For instance, it might be the kind of thing where you’re afraid to stand up for something because you might be called out or whatever.

That’s pretty obvious, it takes some kind of courage to do that, but oftentimes we do things that we think, well, I’m showing courage by stepping back, or by doing something and the thing that we really want is the opposite. For example, let’s say the thing we want is to be on stage speaking,. That is a scary thing for almost everybody. I know Seinfeld has the joke where everybody fears speaking more than they fear death, which means that you would rather be the person in the coffin than the person giving the eulogy at a funeral.

There’s this thing, it’s so scary, and yet it… Our system is trying to protect us and saying, “No, you’d be safe. Step back. Don’t do this thing.” And we tell ourselves, “Well, the courageous thing is to protect myself,” or, “The courageous thing is to let somebody else go forward and really…” Sometimes we just have to reframe and say, “Okay, it’s not really fear that I’m feeling, it’s excitement. It’s just manifesting in a way that feels scary,” or whatever, and it takes courage.

I don’t know if any of that even makes sense or not, but it’s this thing. Where we’re Heather ties courage to our values and living our values, it really opens my eyes to what is true courage.

Tamara:  I think you’ve said so many important things there, Rob, and in particularly two, one where our vocabulary of emotion in practical use may be so much more narrow than the vocabulary of emotions that actually exist. So we chalk something up to fear when really the fear is secondary to the deeper emotion that’s actually primary, but we’re not sure how to express it. I know what you’re saying is true that a great percentage, 80 or 90% or whatever the metric is of people who are terrified of public speaking, and for me, that’s a fearless area.

I, like Heather love a microphone. Thanks again for having me on. I think that that’s something that I try to understand, but I don’t have firsthand experience with it. There certainly are times where I have felt nervous to be in front of a crowd because of something like judgment, something akin to feeling like I could be judged or feeling like maybe there are other people in the room that are better, or smarter, or different than me, hold different views. Those are the things that I fear.

I’m not actually fearful of speaking, I’m fearful of the judgment that could happen. And I think that that is also where you said something else super important, where Heather ties fear to our values. That’s the crux of the issue. In the work that I do with individuals on personal style or copy style, it’s really all about self-expression. And to me, that’s the thing that people fear the most in the world.

It all comes down to being accepted for the self that we express and the truth of the self that we express. And I think that tying fear to values and similarly understanding a greater vocabulary of emotions can really get us to, what is the primary thing that feels like fear, but is actually the reason for the fear?

Rob:  You’re wise in the ways of courage. One of the things that Heather was talking about there with fear too, is that sometimes when we start acting out in the way that is true to us, true to our values, we start to repel people. Especially, when it comes to things like standing up for say, political beliefs, or religious beliefs, or some of these things that tend to be very divisive and we’re afraid to do that, to turn off part of the potential audience, to push away potential clients, or even friends and acquaintances.

And oftentimes, and I’m certainly not advocating for offending all of your friends by doing crazy things here. But I think from a marketing standpoint, sometimes it’s really good to act out of courage in support of those values that we have. Even though it may repel some of our audience away, it attracts those people who are a better fit for our businesses. I can think of a lot of examples of people who do this in different ways, and it’s interesting. People talk about and say, “Such and such is still crass,” or, “He’s so offensive,” or whatever, but that person is offensive to one audience, but attracts an entirely different audience, and is able to make things work.

And if that’s where your values play, and again, not everybody needs to make politics front and center, or religion front and center, or whether you love Coke or Pepsi more front and center. That’s not necessarily where all of the conflict happens. But being courageous in living our values will attract the right people to us and push the wrong people away.

Tamara:  Mm-hmm (affirmative). And I think this comes back to our sense of authenticity in ourselves. The courageousness to act in a way that is in alignment with our values, if that value is traditional or if it is not traditional. I think that there’s an argument for both being divisive right now. I think that’s really where that message of authenticity and whether you’re truly being courageous or not is so important. I think that some people will put on that cloak of, “I need to be more crass. The world is very sweary now, and I should be that way.”

But if that isn’t authentic to you, in fact that isn’t a courageous move because the motivation is courageous. And I think that’s part of it. I think when you’re talking about how we niche and how we express ourselves to match up with our ideal target market, that is one application of courage in an entrepreneur’s life. I think that it’s an interesting thing how intimate and deep courage can be. And that really is why entrepreneurialism is so challenging in every way.

It’s what we confront every day as entrepreneurs, even in the smallest things that we do or that we choose not to do. We’ve already confronted if we choose to go out on our own, the question of, “What will others think of me?” Which tends to be a place of fear for most people and the idea of feeling courage to express oneself in that larger sense. But in every action, in every step, the same question is something that we beg of ourselves. And sometimes it’s not just who will other people, or what will other people think of me rather, but it is who do I think I am for stepping into this authentic open version of myself? And that takes a lot of courage.

Let’s go back to our interview with Heather and find out a bit more about the different types of courage and how they show up in our lives.

Kira:  I want to just back up a little bit and go back again to the different types of courage. How do we know where we fall with the types of courage? Because I feel like I understand the concepts, I love the examples you shared. But in my day-to-day, I feel like I jump around from maybe being fearless one moment to having false courage, to probably less extraordinary courage through my day, at least, but I’m jumping around. And is there a way to really understand where we hang out the most and almost evaluate our current status with courage?

And then as a follow-up to that, is there an ideal that we’re working towards? Is it to be purely in simple courage or maybe that’s not what we’re striving for? It’s like mostly simple courage, but it’s okay to be fearless, a little fearless, and even a little bit of false courage is okay too.

Heather:  I think that we can totally go in and out of this all of the time. To think that we’re going to be in any one box all of the time or that we need a perfect ratio or formula, I feel like that in and of itself is an of patriarchal conditioning. Where it goes back to that checklist or the formula or what is the ratio I’m striving for? Because if you just tell me the rules, then I can achieve them. For us high achievers, just tell us the rules and then we’ll go for that. There is no answer to that. There’s no perfect answer. There’s no rule. There’s no formula.

But I will say, fearlessness, you’re afraid or you’re not afraid, so you are, you’re not. And it’s perfectly okay to be fearless. I think it goes back to that curiosity piece, the awareness piece. If you know that that’s where you are, then it’s just, “Oh, okay, cool. I’m fearless.” And that’s really cool. It’s a way to embrace who you are. Like, “Look, that’s really cool that I’m not afraid of that.”

With extraordinary courage, you don’t really plan for or prep for that. It’s really in the moment. It’s fight or flight. You’re going to react however you react. It’s truly a life and death situation, physical danger. So for the most part and where I think we can learn, and where we can grow is mostly having awareness around false courage versus simple courage. And that really is based on the underlying motivation. So are you trying to be courageous in order to be accepted by others?

Are you trying to be courageous to fit the role and the expectations that others have for you? Or are you trying to be courageous because it’s what you want to do for yourself? A question I often get is, is false courage the same as fake it till you make it? And the truth is, you can use the whole fake it till you make it to support simple courage. The question is simply, why are you doing it? What’s the underlying motivation? I think to think that we would never have false courage is asking us to live up to an expectation that’s not realistic.

We’re human, so I think that it’s always going to be there. From my perspective, I love mindfulness because it allows me grace and forgiveness that I wouldn’t normally offer myself. When I witness that I am in a place of false courage, I don’t have to say, “You’re a bad person, you’re not doing this right.” I can just say, “Look at that. Isn’t that interesting that I’m not in a place where I’m willing to truly show up in the way that I want, for whatever reason.” And I’m just going to witness it, and I’m just going to be present with it.

Because that in and of itself is going to allow me to move through it. But yeah, I think most of us want to start to move into a place of more and more simple courage, simply because the more true we are to ourselves, the happier we will become. And I think that that is that elusive thing that we’re always seeking, searching for, chasing after is that happiness. I often think of Bronnie Ware’s The Five Regrets of the Dying, and the number one regret that she discovered in speaking with so many people who are on their deathbed was that most people felt as though they wished they had had the courage to live a life true to themselves.

And at the end of the day, I think that’s what simple courage is. So if you’re cool with dying with regrets, then false courage it up all day, every day. Far be it for me to tell you that this is what you need, but if you want to move towards a life that you’re like, “You know what? If life is to choose your own adventure, I had some really good adventures and I’m glad that I chose them intentionally as opposed to just following the path that was put in front of me and expected of me.”

Rob:  I’m guessing that this is resonating really well with a lot of people in our audience, simply because people often go to copywriting because they want more control in their life, and they want to do things differently than maybe they were doing in the corporate world. I want to shift the conversation just a little bit and ask about your business, and particularly as you transitioned from being an overworked attorney into coaching, and then this discovery that you wanted to do something bigger or better.

Walk us through that process, how you went from knowing that you weren’t doing the right thing, to figuring out what is the thing that is the right thing.

Heather:  My guess is with a lot of copywriters, you have an idea of what you want your life to look like, but you wonder, is it possible? That’s the biggest thing. So Simple Courage, as opposed to note, I’ve always wanted to speak, and write, and really have a mission-based, movement-based business. That was always the case. From the moment I was a little girl and I imagined what my life was going to look like when I was an adult, it was basically having a microphone, and a large audience where I was making a difference.

The only thing that ever kept me from doing that was a belief that it wasn’t possible. And that was either because I didn’t think I was good enough or other people told me I couldn’t. I’m not a copywriter, but I suspect that you’ve probably heard more than once that your ideal vision for life is not possible. You know what I mean? Either you can be a creative and enjoy your day and your time, or you can be a business person and make money. You can’t have it all. You can’t have both.

And so, even if we rebel against that, we do internalize it, and we start to take it in, and we make decisions around that, and related to that. For me, I knew I wanted to do Simple Courage, but I had my own fear. It’s very meta. That’s why I’m like, “I don’t have all the answers. It’s my journey too.” It’s all of our journeys of, how do you just move forward towards that?

And for me, I think I’d shared in May 2019, I was going to a speaking workshop. I felt very comfortable speaking, but I actually had been invited to a conference to speak on a topic I hadn’t spoken on before, I didn’t have much time. And so, I thought I just need someone to help me quickly put this speech together. I went to a renowned public speaking school to work on this. And while I was there, I don’t know what it is about post-it notes, doing another post-it note exercise, I had this look on my face.

And the teacher came over and she was like, “Are you confused? Do you need help with something?” And I was like, “No, I’m not confused.” And she was like, “Well, there’s this look on your face.” And I said, “I’m having a moment.” I said, “I’m really sad because I’m working on this how to speech, when what I really want to talk about is simple courage. What I really want to talk about is something bigger and more meaningful.”

And she was like, “Well, why don’t you talk about that?” I was like, “Well, no one wants me to talk about that. No one’s paying me to talk about that.” She was like, “Well, why don’t you put it together and just start charging money for it?” And so I was like, “Yeah, why not? Why not practice a little simple courage there?” And so what I decided in that moment was, “I’m going to hire these people. I’m going to work with them for a year, and I’m only going to work on Simple Courage.”

Even as I’ve got my business going on, doing the high-end masterminds, the coaching, the strategic, over here I’m going to explore the simple courage. And for me, that was all I could do at the time, was to make it almost like a hobby or a side project. And so as I worked on that and as I put it together, I then got a little bit braver. And so when people were asking for me to come in and do workshops and speaking, because I was public speaking at the time, I started saying, “I only offer one speech now, and it’s simple courage.”

I was like, “What’s the worst that can happen?” And so people were like, “Sounds great.” And they paid me for it. And I was like, “Oh, look. Now I am a paid speaker for simple courage.” And then as I was doing the podcast, I had a really successful podcast. And I knew I wanted to talk about simple courage. I was like, “What’s the worst that could happen if I closed one down and started another?”

And that’s where… It’s not like I was fearless, there was a ton of fear there, but I just said, “Let’s just do it. Let’s just try it. Let’s get uncomfortable.” The first thing I did was, I made an announcement. I committed to, “I’m going to stop this podcast so that I can work on another.” And then as I was working on a piece in the business and I would say, “Well, what if we did this with Simple Courage?”

It’s not as if I burned the whole business down one day and just said, “Let’s take this huge leap.” It was with little bitty steps that felt really huge at the moment. They felt really scary that I said, “Let’s just try this. Let’s just try this. Let’s just try this.” And so slowly, over time we decided to fully transition and end our masterminds and strategic work so that we could go all-in on Simple Courage.

It might look as though this just happened in a single moment, but as often happens, when you look behind the scenes, it was a journey. It was just small steps in the making that eventually to others, the outside world, looks like one huge leap.

Kira:  To a copywriter who’s listening and is like, “I want to make a big pivot too,” what advice would you give them now that you’ve been through it, through the pivot? Maybe some practical advice on what you would do differently, or maybe what you did exactly. And then even just some mindset advice about how to handle that transition and change, because like you said, it’s not easy along the way. It could take a month. It could take a couple of years. What advice would you give based off your experience?

Heather:  One of my frustrations, and the interesting thing is I don’t actually have an answer to it, but I want to acknowledge it, is I’m an all-in kind of girl, which means I struggle with having my attention pulled in multiple directions. When I left my law firm, for example, I did not have a side hustle. And you might have a lot of people doing that now, they’re in corporate, but they have the side hustle and they want to build it. That’s not my personality.

Even when I left the law firm, I didn’t really have a plan, but I knew I had to exit out to be able to go all-in on that. I was doing a little bit, like you and I, we were doing some research and development. We were doing a little bit on the side, but I was really still focused on serving my current clients. And I wasn’t able to really go all-in until February of this year. And what I wish was that I had a different personality, I guess, because I really wish that I could have been developing and digging into Simple Courage even more back in fall.

Because it’s been frustrating for me, how long it’s taking me to bring this life. I’m such an action taker, I’m a quick start on Colby that I just wish that we were further along than we are right now. And so much of that was being an all-in kind of girl. For those of you who can juggle both, then that’s what I would do, that’s what I would recommend. It definitely is going to provide a better safety net for you to make the pivot, but still keep with what you’ve got.

I’m trying to think, could I have any other advice? The other piece is I think… When I was doing the other parts of the business, when I was doing the strategic coaching, the masterminds, I never had fear putting those offers out there. And because I have insecurities around Simple Courage, because it feels more creative, I have a lot of insecurities around that. Do people want that part of me? I very much have noticed that I get a little bit more paralyzed. I do procrastinate a little bit more.

And so with that, I’ve just tried to be gentle with myself. I’ve just tried to say like, “Yeah, I get that in other areas of your life, even in business, it’s easy for you to take action, but you were fearless there, Heather. And you’re not fearless here. You’re scared. You are scared to death.” In that sense, you just have to know that it’s okay for it to take a little bit more time and to just be a little bit more forgiving of yourself and a little bit more gentle with yourself as you’re taking the action.

The question is, are you showing up every day? Not are you showing up every day the way that you would if you were fearless? Because you’re never going to be able to compare. You’re never going to be able to compete. But if you show up every day and you’re getting a little bit more uncomfortable every day, then you’re doing the thing. That would be my recommendation. If the pivot feels huge, if the pivot feels big, if it feels so overwhelming that you have these days where you just feel paralyzed, know that any action is better than no action.

Rob:  Heather, as you talk about that, I’m curious, what things went wrong as you went through this whole process? Where did you struggle?

Heather:  When I started my first business, it was just me, and I’m scrappy. There was really not much I could screw up, because I had time on my hands. And when we were transitioning to Simple Courage, my business had grown and I had a team, I have employees. And so there were a few transitions happening there. One was the roles and responsibilities weren’t going to look the same, and they wanted to be a part of Simple Courage, I wanted them to be part of Simple Courage.

But part of that was trying to figure out, “How do we make that transition with the team? And who’s going to do what?” And as I was developing it all, I had employees who were ready to go and I still had to get it all out of my head. I have to say, in so many ways when you’re developing something from scratch, it’s almost easier when it’s just yourself initially. That definitely, I don’t know if I would call it a screw up, but there’s definitely been a lot of hiccups in trying to make that transition to being able to keep your employees employed while you’re burning down one revenue stream and starting another, figuring out how they’re going to move over, what their roles and responsibilities are going to look like.

And it’s really hard to delegate things or build systems around things when you’re developing it for the very, very first time. That has been a huge learning curve and even more of a reason to maybe not really do the whole all-in kind of thing. That works when you have the time, space, ability, finances, and it’s just you. When you have an entire team, that probably was not the best approach. It’s worked out, but definitely, there were many, many uncomfortable moments this spring trying to figure all of that out.

Kira:  Heather, I still have so questions for you, but we’re going to wrap, so we’ll have to bring you back to ask all the other questions. But can you talk to us a little bit about where you are in this process? The next steps, you mentioned the founders launch. Can you talk about what you’re about to launch and what you’re most excited about right now?

Heather:  Yes, yes, yes. We are through our betas. We’ve gone through all of our beta programs and I know you participated in one. We loved having you in there, Kira. We are now moving to our membership. That really is the core of what the program, well, not the program, but the platform is all about. It’s about community. And it’s about being in a place where it’s not curriculum-based, but it is being in a place where you have the ability to explore, to stay in a place of curiosity, to be guided so that you’re not having to figure it out on your own.

And to be surrounded by others who are also committed, and in this same place of wanting to really get aligned with their values, be true to themselves, to get uncomfortable, and to be more courageous every day. That’s going to open in September, but we’re doing founders launches this spring. For anyone who is like, “I need this in my life. I want this in my life,” they are going to have the opportunity to raise their hands now.

And just from a business perspective, the way that’s working is we’re giving crazy insanely discounted pricing for anyone who joins lifetime pricing, lots of perks, lots of bonuses. Mostly because it lets us know the interest level, and it lets us reward those who are willing to invest in themselves and us before doors open. That’s where we are, that’s what we’re super, super excited about, is inviting in our founders now, and then giving them lots of love over the summer. And then really gearing up for this amazing community that will start getting together starting September 1.

Rob:  Heather, if somebody is interested in that or they want to connect with you, or they want to listen to the new podcast, basically get more Heather in their lives, where should they go and what should they do?

Heather:  The easiest way to do that is just go to That will definitely get on the email list, because that is where we send out all of the links for founding member offers, all of that good stuff, and we don’t put that anywhere else. Definitely get on the email list, and you can also follow us on Instagram, that’s also Simple Courage. Right now we have a pop-up podcast, so we’re playing with that concept. I love strategy and marketing and all the things.

So we’re playing with this concept of a pop-up podcast, here today, gone tomorrow, so they can come listen to that while they still can. And that’s on any podcast app, again, Simple Courage. We keep it easy. We’re going to have a more creative one coming out later in July. But if they subscribe to the pop-up podcast, that’s going to turn into the other permanent one. If they’re subscribed, they won’t miss an episode.

Kira:  Well, thank you Heather, for joining us today and sharing so much behind the scenes with Simple Courage. I know you’ve helped me look at courage differently, and helped me personally and in business too. And I am excited to be a founding member. I will be a founding member as well. And so anyway, thank you for being here with us. We really appreciate it.

Heather:  Thank you so much for having me on. It’s been a pleasure.

Rob:  That’s the end of our interview with Heather Hubbard. And before we go, obviously, as we do every week, there’s a few more things that we want to touch base on. Number one thing that jumped out to me from this second half is the one way that we show courage isn’t necessarily by bravely moving forward, but sometimes it’s stopping to ask for help. We don’t have to do everything on our own. Sometimes it takes a lot of courage to admit that we can’t do this on our own, and that just started to occur to me as Heather was talking about how this shows up in our business and what keeps happening to us as we go through some of these struggles.

Tamara, what else stood out to you from this part of the interview?

Tamara:  For me, a lot of this felt like important messages to the collective right now. There was both the collective and the individual, but as I think about what Heather’s saying in this second half of your conversation, it strikes me that we’ve been as a collective, such a state of exposing places in which false courage is coming up versus the opportunity to exhibit simple courage in everyday life. And I’m excited about how we might be able to refine our ability to recognize this and to call upon simple courage more regularly with both more tact and effectiveness than maybe we’ve individually or collectively been able to do before.

And I think that’s actually one of the challenges that humanity has right now. It’s about, of course, effecting our ability to achieve more in life in general, but also in our work too. If I think about the collective and how we’re exposing places in which false courage is coming up, versus the opportunity to exhibit simple courage as a collective, when I think about it as individuals, I think back to what simple courage is, and I think of course of Shakespeare, “To thy own self be true.”

And what does that mean especially as we look at our futures coming out of the past year and a half that we’ve all experienced, and the changes that we each have been confronted with potentially making in our lives. And for a lot of us that is, professionally leaving something that we’ve done before that felt safe and that felt positive, and acceptable, and trying something new, having new ideas of how we want our lives to look. And as Heather said, the only thing keeping us back from experiencing that is the belief that it’s not possible, or the belief that others have instilled in us that it’s not possible.

And the act of rebellion that it takes is the challenge that we have now. Are we willing to take that act of rebellion to experiment with how we want our lives to look, and using simple courage to step by step choose something new in our professional lives, developing something that is exciting to us, and that feels aligned for us, but that maybe hasn’t been given to us as a path that is acceptable or that will be successful on some other external scale of success?

Rob:  Yes. As you mentioned, the last couple of years, last year and a half, it’s come really clear to everybody that life is not safe. And certainly there’s a lot to be said for trying to make life safer, but the fact of the matter is, it’s not 100% safe. And that means that it does take some amount of courage to step out into the world, and do the things that we want to do. And obviously you can apply this to all kinds of things, and I’m certainly not taking a side favoring like, “Oh, he’s talking about should you wear a mask or not?” I’m not talking about that.

The world, isn’t a safe place, no matter what, before, after the last year and a half, and it still takes courage to get out there. Some of the things that we tell ourselves, things that aren’t unsafe feel unsafe, like getting on stage, like getting in front of the right clients, like pitching a client that you wanted to work with and don’t know. Some of those things can feel safe and they’re not unsafe physically, but emotionally, there’s some costs that go into that.

So stepping into a courageous role is something I think that more of us can do. And as I was listening to Heather talk about this, it actually reminded me of the book, Alter Ego Effect which has been passed around. It’s Todd Herman’s book about, how do you put on this alter ego, this other personality that allows you to be something that you’re not? And I think these two ideas of simple courage, alter ego go hand in hand and allow us to step out into a world that sometimes is physically unsafe and sometimes simply feels unsafe, and lets us move forward in the things that we want to do.

Tamara:  There was something interesting to me in this tension between false courage and simple courage, that you almost need to have the false courage for a split second in order to have the simple courage. And I think in that way, false courage is okay to have, because it’s what will lead you to the actual step you have to take, that leap that you have to make. And for me, I love that you’ve brought up Todd Herman’s book, Rob, because I think in it, he suggests that the real alter ego isn’t Superman, it’s actually Clark Kent. Superman is the real guy.

And I think we all have that in it. We could probably have a whole conversation with Heather about superheroes and the four types of courage, but in real life application, that false courage moving to simple courage, that step of recognizing your… for me, Wonder Woman. For me, knowing that Wonder Woman is the real me, Diana Prince is just the person that I walk through everyday life with. That’s what allows me to stand on that precipice.

When I’m making and particularly the courageous choice to pivot in one’s career or to pivot in the decisions one has made up until a certain point, it’s that standing on the precipice, I can see Wonder Woman now. I see the wind in her hair and I see her standing on that precipice, the place where you’re about to take the leap of faith, the moment of not knowing whether or not you will fly or whether or not the parachute or the safety net will appear.

That’s when you choose going from that false courage to take the step in the simple courage of being in the risk. Feeling that fear and doing it anyway, is at once terrifying and completely freeing.

Rob:  Agreed. Courage, for lack of a better definition, is the principle of action. Having it allows us to take action, but also it’s necessary in the moment of acting. It definitely makes us more able to accomplish the things that we value, things that we want, ultimately.

Tamara:  That’s so true. And I think that taking of action is particularly important when we look at it in terms of the journey we’re taking to courage and to making those leaps, and knowing that we don’t really have to do them alone if we can find a community that can support us through that leap, and through that change. And I think that’s part of what makes a courageous person able to walk those steps or take that leap.

You can have that courage and stand on the precipice and be there for such a long time. If you feel you have no support at all, will you take that step on your own? I think it’s so much easier. It’s still scary, you still need to have that sense of courage, but it is easier when you find a community that can support you through that change.

Rob:  Let’s go back to the original idea you started with, the Cowardly Lion was advised, if the lion hadn’t had the Tin Man, and Scarecrow, and Dorothy, and maybe Toto, he never gets to the end. Actually none of them get to the end. They all needed each other, which is the point of the story. But where he was lacking courage, supposedly throughout the entire movie, it was the community that helped pull it out of him. And so I like that, I like that frame. And that might be a pretty good place to stop here.

We want to thank Heather Hubbard for joining us on the podcast today. If you want to connect with Heather and find out more about Simple Courage, you can find her podcast, which is also called Simple Courage on your favorite podcast app. Be sure to check out, where she’s doing some pretty cool things, helping in particular women be more courageous in the things that they want to do with their lives and with their careers. So make sure you check that out.

Tamara:  That’s the end of this episode of The Copywriter Club Podcast. The intro music was composed by copywriter and songwriter, Addison Rice. The outro was composed by copywriter and songwriter, David Muntner. If you enjoyed what you’ve heard, please visit Apple Podcasts to leave your review of the show.

Rob:  Thanks for listening, everybody. And I want to thank Tamara for coming on and sharing your insights here, so thanks for being here, Tamara. You should check out her podcast and everything else that she’s doing. And we will see you all next week.

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