#150: Why You MUST Write Your Purpose In Pen & Your Path In Pencil With Heather!
4 Nov 2025 · 23 min
Heather Monahan shares her career journey of setbacks and successes, arguing you should commit to your purpose but stay flexible about how you get there. She offers advice on goal setting and building confidence when life doesn't go as planned.
Chapters
Come on this journey with me each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. Fasten your seat. I'm ready for my close up. Hi, and welcome back. I'm so grateful you're back here with me today. Okay, so as usual, lots of interesting things going on. I'm sure there's lots interesting going on in your life, too. Okay, here's the the message I've been thinking a lot about over the past week. Write your purpose in pen and your path in pencil. Here's what I mean by that. Forever. I did not think that way. This is a very hard concept for me to grasp. I used to think, write your purpose in pen and your path in a black Sharpie. I thought for sure I knew exactly what was happening in my life. And that was so incredibly wrong. It's amazing. And what I want for you, because I don't want you to have to think the way that I did, is it's impossible for any of us to know outcomes. It's impossible for any of us to know what's going to happen outside of ourselves, our world, our industries. So many different things can happen. And the more that we adapt this. Write your purpose in pen, that doesn't need to change, but your path and pencil, because your path is going to change so many times. The easier life will become and the more accepting we can become, which will allow us to flow through the changes and challenges much easier. Right? When we write things in permanent marker, we freak out when suddenly they no longer exist or they're not possible or not feasible. When everything's written in pencil and can be erased and changed on the daily life becomes much easier. And again, I'm just learning this, so definitely I am not a Jedi over here on this, but I'm really starting to embrace it. And I want to share with you what happened this week that kind of, kind of gave me this epiphany. Okay, if you don't know my whole story, the long and short of it is that I did really well in corporate America. I had a successful career. I was a chief Revenue officer. And after 14 years at the same company, being promoted three times and named one of the most influential women in radio, I was fired. Three weeks later, when the CEO I had worked for became ill, he chose his daughter to replace him and she fired me immediately. So that was my first big, you know, write your purpose in pen, your path in pencil moment. I didn't know it at the Time I hadn't heard those words before. I was just more in shock, right? And I took messy action, ultimately posting about getting fired, which landed me on the Elvis Duran show. Elvis imparted so much confidence in me when he told me that I was obviously writing a book. And he changed my life, the trajectory of my life that day, because I googled how do you write a book? And that's how I wrote Confidence Creator. From there, I googled how do you sell books? And I figured out speaking. I'd been speaking my whole career, so that was easy. And that's what stumbled me into, literally, I had no idea, the professional speaking business. So there's so much we just don't know outside of our own limited worlds. And my old limited world was the media business. And no one paid speakers back there. So for me, I was learning so much so quickly and really writing my path in pencil, right? Because I got fired, didn't know what I was going to do. So that was in pencil. Then I asked for help that landed me on the Elvis Duran show. That was in pencil. He told me to write a book that was in pencil. I wrote the book that led me to the speaking business. That was in pencil, right? All these things were unfolding, not in permanent marker. And I'll Never forget in 2018, when Confidence Creator came out, I thought, okay, go all in on this book, promote the heck out of it. Find out how to sell millions of books so that you don't have to worry about income and, you know, you found success as a new first time author. That's just how I think, right? And again, I was still thinking in the permanent marker way of thinking that this is what I'm gonna do. I'm gonna be a bestselling author, sell millions of books, and this is my business. And then suddenly what I started realizing was this space. Speaking opportunities I were getting were more money than the books I was selling. I wasn't selling millions of copies, thousands. And there's a huge difference when you're selling millions versus thousands of books. So I started. I don't want to say I gave up on Confidence Creator, but I shifted and I was frustrated, right? I remember thinking, well, my plan had been, this is the way I saw it going. I was going to be this bestselling author and this was going to change my life. And it wasn't. It ended up being that I had to pencil it over to the speaking business and kind of shipped away. So there definitely was a day, probably sometime in 2019 where I remember Thinking, huh? The book did well. I'm happy with it, but it didn't do what I thought it would do or what I knew it had the potential to do. And I remember I kind of just threw my arms up and said, oh, well, you know, it's over a year now. I've got to move on and really immerse myself in the speaking. And that's when I went all in on my TedX and getting my TedX done and, you know, doing more and more speaking engagements. And then, of course, in pencil, the pandemic hit. And that completely obliterated the speaking business literally overnight, right? And I had to transition into a virtual speaker and a coach and a consultant and all this insanity. And then ultimately landing a deal with Harper Khan's leadership for my new book, Overcome youe Villains. Okay, so why am I sharing this with you? I'm sharing this whole concept. Write your purpose in pen and your path in pencil. Because I would have made my life so much easier had I embraced this. And I want you to try to embrace this. I'm trying to embrace it now. Here's what happened this week that made me think about all of this. So this week, like anyone, right? There's good things that happen some days and bad things that happen. And, you know, we never know. Walking into a week or a day, we have our hopes are things that we think are gonna happen, but, you know, you never know. And I'd had some challenges. My son was sick this week. There was a Covid outbreak in his school. My son was back at home. You know, just some small setbacks. First world problems again, nothing, you know, devastating. But I was definitely feeling a little discouraged. And I went for a workout one morning, and I'm coming back in my car and here's something important for you to do. If you don't have a Google Alert on yourself, take one out. Now go to Google. Type in, how do I take out a Google Alert on myself? So I have a Google Alert on myself. And on any client that I'm interested in approaching or any big speaking opportunity I wanna land or anything important to me, I take a Google Alert out. That way, when they hit the newsfeed with any upcoming information, exciting new information, you get an email in your inbox. You don't always have to be searching for it. It's delivered to you. So that morning I got out of my workout, I turned my phone on and I saw an email from Google Alert Heather Monahan. And I opened it and I about fell over my first Book Confidence Creator. Remember I wrote and self published this in 2018. Now it's 2021. Had just been named on the Forbes list. Top five books for women in business that must read. You know the top five must read books in Forbes? Not making this up legit. Go Google it. And I'm sitting there looking at the list and looking at my book Confidence Creator on there and remember how I had said, I don't wanna say I gave up on it, but I had moved on from it because it wasn't following my timeline. Right. So your purpose is in pen, your path is in pencil. I had my purpose in pen. My path in pen. And when anything didn't go the way that I thought it should or would or had hoped, I kind of moved on from it. Right. So I thought, okay, well great. I'm glad I wrote Confidence Creator. It's a great book. I got great feedback on it, amazing reviews. It didn't take off the way I thought it would. So I moved on to my TEDx and then from there I moved on to teaching at Harvard, Then I moved on to my speaking business and then I moved on to my Harper deal. Right. I just kept moving on, moving on. And what's so interesting is I always knew that book had the potential to have something this big happen for it, but I just thought it had to happen in my timeline. And what's so important for. I want you to know this, because I don't hear other authors telling me this. Here I am years later and I'm finally hitting some of the lists I had prayed to get on. Right. No, they didn't happen in 2018, but it just hit the Forbes list on 2021. I never saw that coming. I mean, I was so proud. I started crying when I saw the list. And then there's something. Another reason it really got to me emotionally is it took me back to 2018. I have my second book coming out now in two months. But it took me back to being a first time writer and remembering what that was like and remembering my hopes and dreams and what I thought was gonna happen, which didn't. Right. But here I am years later and I am finally achieving some of these marks that I thought were gonna happen back in 2018. Clearly the path is in pencil, not in pen. And it was another funny tidbit to the story is that yes, I had wanted to hit the Forbes list, of course, the short list for must buy women's books and many other things that I wanted to achieve, but I kind of had Moved on. But back when I first decided to write my book, I went to my family and I tell us the whole story actually about this in my new book, Overcome youe Villains. But, you know, one of the things that was really hard for me was that my mom was very upset with my book and didn't want me to publish it once she read it. And then my sister, who's an attorney, super smart attorney, advised me not to write it because she said it's very similar in her legal opinion to the Jen Sincero book. You are a badass. And she said, I just don't think this is gonna bode well for you. You could get sued. Her book is huge. You don't want to put yourself in a bad situation. I would not move forward. So both my mother and my sister had told me not to move forward with my plan and goal with. With my first book. When it was literally two weeks away from launch. Luckily, I called my editor. He had written 19 books. He reminded me, don't take advice from people who haven't been where you're going. Reconnect with your why. Why did you write the book? I reconnect with my why. I reminded myself they haven't written books. Their advice is meant well. Right? And coming from a place of good, however, it doesn't have to be my decision. I don't have to take on their advice as my decision. I thanked them both and moved on with my plan, brought the book to market. And I'm so grateful today, by the way. I did that. That was super hard. You know, I'm not saying that was easy. I didn't know if my mom was ever gonna speak to me again, and just was a really very hard time. I was doing something so different that no one had ever expected from me. You think people are gonna be so excited, but again, it's not in pen, it's in pencil. And it can change. And it definitely changed. It did not turn out the way I thought it would.
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Okay, but cut to now. Why am I telling this whole story now other than this is a great chapter in my new book Overcome youe Villains. But the reason why I'm telling you this to you now is when I opened up the Google Alert and I read Top five Books for Women Forbes list. I looked at the books on the list. Guess what book is right next to Confidence Creator by Heather Monahan Jen Sincero's book And so it was kind of this serendipitous moment for me to see full circle that I'm so grateful again. People care about you. People love you, they want to support you. They're coming from a place of love and trying to protect you, which I so appreciate. But when you tune into that voice inside of you, you will know the answer for you, whatever that is. And while it was not easy, it was simple. I knew that I was moving forward with that book, even though I felt so scared of what lie ahead of me. But to see Jen since Arrow after, after Confidence Creator on the list was kind of that moment where I said, gosh, why didn't this happen back in 2018? Right? It would have been such a watershed moment, but I'm still grateful for it. So grateful in 2021. And it's just the reminder that just because things didn't come in the timeline that you thought they were going to come in doesn't mean they're not coming. You just might need to wait a little bit longer, which is really what I had to do then. So crazy. I have a second example of this. Write your purpose in pen, your path in pencil. Okay, So I explained to you I got fired. First thing I did was write and self publish Confidence Creator. Then I launched my speaking career. When I started seeing that I made more money, way more money speaking than selling books, I decided I think I need to get into the speaking business. Let's figure out, you know, research. How do you become big in speaking? One of the ways is to do a TEDx talk. And so I went all in on my TEDX talk. I applied for 100 different TEDxS. By the way, this whole story is in the new book too. This is a chapter and I talk about how I got my TedX talk, what went into it, the challenges I had to overcome and how the outcome actually was behind the scenes. So I went all in on this and in my mind that TedX was gonna blow up immediately because I knew it was gonna be so good cause I worked so flippin hard at it and I'd have 50 million views. This is what I decided in permanent marker, not in pencil in my mind. And that it was gonna happen immediately. And that when it would happen, my speaking business would explode. I'd be book solid, making millions and boom, life is good. Okay, let me tell you what really happened, which again, there's more detail on this in the new book. But I delivered the TedX talk. It was amazing. It got promoted to Ted, which I didn't even know that could happen. My TedX talk is now on Ted Crazy. I have a TED Talk, which originated as a TEDx talk, and I'm so proud. So to me, I'm like, okay, this is just one more indicator. It's going to get millions of views. Well, guess what? My TED Talk today still still only has 45,000 views. I think it's, you know, it's still less than 50,000 views. Nowhere near, in my mind, with my permanent marker that it was supposed to be. And I got really discouraged about that. And then, of course, right after that, this came out. November 2019. The pandemic was a couple months later. And then everything disappeared. All my momentum disappeared. It just. It was a really frustrating time for me. However, I'm here today to give you good news and hope in that purpose and pen path and pencil. I just landed the largest international speaking engagement of my entire life. I'm sharing the main stage with the CEO of Bain Capital, Colin o', Brady, Jim Kwik. So many unbelievable rock stars. I mean, literally a speakers, the best of the best. And we're going to be speaking for thousands of CEOs and presidents of companies. It's the biggest international speaking engagement of my life. And so it was so funny. I was working with the team on my speech and the event and going through some administrative stuff with them, and one of the guys on the call said, hey, I just wanted to mention what. What really put us over the edge with you? They were looking for a speaker that could address sales, and they had found many, of course. Right. There's probably thousands of great speakers out there that can speak to the topic of sales. And so he said, what really put us over the top with you? What blew us away was your TED Talk. And in that moment, hearing that, it brought everything full circle to me. I had worked so hard at landing that TedX. I had busted my butt to promote it, to get out and get PR and press for it, to do the best job that I could. I had so, so many hopes and dreams in that talk. And when it came out on Thanksgiving Eve, which is the worst time possible, a holiday you don't want, nobody's gonna be sitting around watching talks when they're, you know, celebrating. And so it was just this really, everything kind of was, oh, it went poorly, went poorly, you know, and I didn't get the views I thought I would get. And then as I sat on that call and heard the reason, that they really ultimately went with me instead of all these other great speakers was that they loved my TED Talk and so it didn't go I knew my TEDx talk would be important and I really believed it would be. It turns out it is. And it was. And again, that was in 2019. I did that and here we are in 2021. It made the difference for getting me this opportunity today. So don't give up on those hard work things, those big things, whether it be writing a book or landing a TEDx talk or anything that you are working on that's important to you just because in your mind you wrote it out with a permanent marker that it was going to go this way specifically. Maybe it's still three years away and in three years you're going to see how it came full circle. And I always say this, you can't see the dots connecting looking forward. But today, right now, in 2021, I can look back on 2018 and 2019 and I would say to that younger version of me a couple years ago, hang in there. I know it's not going the way that you thought it would with your permanent marker writing out your plan, but I can promise you this, it might just be much better than you expected. Let it be written in pencil so I hope that message resonates with you. Okay, hold tight. We're going to be right back and I'll be answering one of our listeners questions. Meet a different guest each week.
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Okay, I got a great question from one of our listeners who's read the book, who's done the program, who's done the course, and done a lot of this and by the way, the course, all that stuff you get as free. I have a $500 bonus bundle for free. When you purchase my 2499 book, you pre order it. Now you get the 500 bundle, the course, the workshop, the the first chapter. So many things. So please check that out at overcome your villains.com okay hey Heather, there's one thing I'm struggling with. I find myself doing for others or creating goals that benefit besides myself. It benefits other people, not myself. Much of this is due to trauma that I went through growing up and feeling like I had to take care of everybody else, be the peacekeeper, be the optimistic one. But for me it's different. I tend to be harder on myself and focus on what I can do better, downplaying my success and not embracing the positive value that I actually create. Your tip on journaling and using positive language is simple, but it's helped me a lot. With that being said, I also have a hard time creating goals for myself. Not sure what your advice is. As a big part of the business that I've created is all about doing good. And I'm in a business where people typically say what's in it for me? And I don't want to be like that. Let me know if you have any suggestions. Okay, so here's the thing. You don't need to feel guilty for success. Instead, flip it this way, the more success you have monetarily with your business, whatever it is, the more good you can do in the world. When you are a good person, money and success is only going to intensify that it's not going to make it. It is not bad to have money. The more money you have, the more freedom you have. The more freedom you have, the more opportunity to do good in the world you can do. When I was making a lot of money in corporate America, I was sitting on the board of a major charity, doing so much work to help others, right? The more affluence I had, the more wealth I had, the more free time I could contribute to give back. So realize it's not only is it your job to set big goals and go after them for your success and your life and happiness, but that way you can in turn give back and do so much more for others. Also, you can inspire others. The more you share your story, my frequency and story is gonna be different than yours. And your frequency and story is gonna connect with a different audience that mine doesn't. So it's your duty to share your story. It's your duty to share your successes. And I remember learning this the hard way when I had an assistant livestream a story that I gave on Facebook. I didn't know she was doing it. I never liked to share my wins before this, and that day changed my life. I received hundreds of DMs saying, Heather, you could do it. I can, too. Thank you for giving me the courage. Thank you for inspiring me. It's our job to share our wins. It's our job to inspire others and to make this world a better place filled with hope. And if you're having a hard time setting a goal, I would say reverse engineer it. Put it out on social media. This is what I did. Hey, guys, I've got a second book coming out. I'm super excited about it. I didn't have my second book coming out. I wanted pressure put on me by my community because I knew they'd ask me about it. Reverse engineer your goals. Tell your circle of friends and family. Hey, I'm doing this. Hey, I just set a big goal for my revenue for my company this year. Here's what I'm going after. Write it down. Get intentional about it. Read that goal every single day. Visualize yourself achieving that goal. You tell other people about your goal. Ask them for help or ideas. Start really living in. This goal is happening. Just remember, it doesn't have to happen in permanent ink. It can happen in pencil. Just like it's kind of happening for me. So I hope that helps. And until next week, keep creating your confidence. And don't forget, if you haven't signed up for my book launch team yet, please go to overcomeyourvillains.com, scroll to the bottom of the page and sign up for the VIP book launch team. We go live on Zoom. We have the most unbelievable group of people. We have amazing live team meetings. I would so appreciate your help. No one succeeds alone, and that includes me. Until next week, keep creating your confidence. I decided to change that dynamic. I couldn't be more excited for what you're going to hear. Start learning and growing in. Inevitably, something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. Come on this journey with me.
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