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On the Brink with Andi Simon

331: Jodi Flynn—How To Go From Dreaming To Doing, At Work And In Life

Oct 3, 2022

Hear how your hoped-for success starts with self-awareness

As I continue to share with you some of the great podcasts I've done with amazing women over the five years of On The Brink, I'm re-posting my interview with Jodi Flynn, a remarkable woman who is helping other women succeed. She's also the bestselling author of Accomplished: How to Go from Dreaming to Doing. You will hear how Jodi's system of self-assessment reveals how your unconscious often creates negative chatter in your mind that tells you that you don’t have what it takes, keeping you from living the life you know you are meant to have. Learn from Jodi's wisdom and see if you too can have an aha moment that opens up all kinds of possibilities for you.

Jodis bookThink about where you want to go and then get there

Jodi's approach helps strong, Type-A women let go of their stress so they can truly believe in themselves, and with clear vision and confidence, take positive actions that will help them achieve the success they want.

During our conversation, you will learn how to remove the barriers that keep you from having the experiences you know you were meant for...whether that's gaining more clients, growing your team, winning awards and recognition in your industry, getting that promotion, speaking, podcasting, writing a book. If you’ve dreamed it, listen to this podcast to see if you can actually achieve it — with a little of Jodi’s help.

About Jodi

Jodi Flynn is the founder of Women Taking the Lead, a podcast and community of ambitious entrepreneurial women who want to go BIG. She helps her clients see how extraordinary they are and then set priorities and develop an action plan so they can achieve their biggest goals with ease. To connect with Jodi, you can find her on LinkedInFacebookTwitter and her Women Taking the Lead website.

Key takeways to help with your own life and career:

  • How Jodi's constant fear of judgment and being wrong held her back 
  • How she used “small bursts of courage” to push herself out of her comfort zone, allowing her to be more successful in her corporate career
  • The importance of self-awareness in leadership to better assess others
  • Being aware of personal limits to consistently stay in a healthy mindset
  • Choosing the right team 
  • The importance of taking care of your mind, body and emotions to perform at your best 
  • Focusing your attention on one thing at a time 

Want more on how to believe in yourself and your capabilities? Here are 3 great podcasts 

Read the transcript of our podcast here

Andi Simon: Welcome to On the Brink With Andi Simon. Hi, I'm Andi Simon. I'm your host and your guide. I'm an anthropologist who works with organizations that need and want to change. I'm also an author of an award winning book,On the Brink: A Fresh Lens to Take Your Business to New Heights that you can find on Amazon, and in all kinds of formats. Our podcast is designed to help take the themes of that book and expand them, multiply them in all kinds of ways and bring you close to people who are in fact on the brink and changing in very transformational ways.

I have with me today Jodi Flynn. Now I've done a podcast on Jodi Flynn's podcast, and you need to look her up on Jodi is really an inspiration. A little bit about her background, and then I'm going to turn it over to her. Jodi is a founder of Women Taking the Lead, a podcast and a community of ambitious entrepreneurial women who want to go big. She's looking for women who are type A, who already are successful, but have not achieved the level of success that they would really like to achieve and then moving along. But sometimes it gets stalled. And we work with businesses often the same way. They've been growing great, and all of a sudden, they stall.

So Jodi helps her clients see how extraordinary they are and set the right priorities to get organized and into action, so they really can achieve their biggest goals with ease. She became an Amazon Best Selling Author with the release of her book, Accomplished: How to Go from Dreaming to Doing. Welcome, Jodi, and thanks for joining me today.

Jodi Flynn: Andi, it's so great to be here. I'm so glad we're back having a conversation again, this time focused on your community. And so for those of you who are listening, we're so glad you could join us. This is going to be all about you.

Andi Simon: Well, from two women who are a little type A and who both accomplished great things, I'm going to share all of our little wisdom. So let's start with Jodi. Tell us about your story. Clearly, you have arrived and are moving. You want to share it. Tell us how this whole thing happened? What's your journey?

Jodi Flynn: It's really funny when you hit a certain age and people are like, What's your journey? You're like, What do I leave out? But I think I can sum it up by hitting the high points. I was a very shy child. I had a hard time talking to people when I was out in public. With my family, closest friends at home, it was fine. I could be myself and be exuberant and my natural self was in full effect. But when I would go to school or go out to work, and then off to college, I was held back. I would hold myself back because I was afraid of doing or saying the wrong thing. It was a little bit of social anxiety.

And so I spent a lot of those years stressed out, and that caused me to be exhausted. So I would say, although I was a good student, I did not feel like I was very accomplished until I could kind of get over myself and my ego and stop worrying about what other people were thinking and doing. Because the reality is, most people are so busy, they're barely paying attention.

Andi Simon: Now Jodi is telling you something you would never ever know if you were looking at her, like I am, and listening to her talk the way she does. So keep telling us, what happened? And how did you overcome this exhausting, stressed out, I can't talk to people?

Jodi Flynn: It was a series of events. There were some books I read, like Don't Sweat the Small Stuff and The Four Agreements that helped me to see things from a different perspective. When I said, Get over myself, I think that really started with Don't Sweat the Small Stuff, and it's all small stuff. And then I just had some experiences where I realized like, oh, people do want to hear what I say. People do appreciate my perspective. So I started taking some risks and that's what you have to do.

When you do feel like you're kind of tight in a box and you're not fully being yourself, you're not living the life you want to live. You do have to take some risks. So I would just take some small risks, I call them small bursts of courage. I would take these small bursts of courage, I would take action. And the feedback I got was really great. And it allowed me to explore more and more just being my authentic self out into the world until finally, when I was in my corporate career, I just felt like I was rocking and rolling. It was in my corporate career that I put a lot of what I learned into action.

And you know, for anyone who may have read the book already, a lot of the stories I draw upon are from my journey from high school to college, my corporate career, all the things that helped me to learn to just be myself and put my skills, talents and experience out into the world. And it manifested in a few different ways that we'll probably talk about a little more, but it started small and grew from there.

Andi Simon: Now, since your book has those stories, can you share one or two in that corporate vein? I have a hunch a lot of women listening are going to be in that corporate zone and want to know, What did she discover? And how come I can't get rid of the small stuff?

Jodi Flynn: So one of the things I discovered, because my bachelor's was in psychology, and I was actually three credits shy from achieving my master's in counseling psychology, but I'd known for well over a year, I did not want to have my master’s in counseling or to be doing counseling. But long story short, I never pictured myself working in the corporate environment. I thought I would be working with people one-on-one, or maybe in small groups. And so when I was looking for it, I needed to pivot because I wasn't going to complete my master's. So I took an entry level position just to pay the bills.

And I remember when I was looking at job postings, now this was back when you would look them up in the paper, I'm dating myself a little bit. I was afraid to apply for jobs that paid well, because I didn't feel like I had anything to offer a company. I had my psychology degree. I had just about finished my master's in counseling. In my view, the corporate world would not value what I had to offer, which the reality is, I didn't value what I had to offer. And I put that story on my future employers.

So I took a job that paid very little. It was one of the lowest paying corporate jobs. You could take the entry level. And it was when I entered that corporate arena, like within six years, I would get promoted five times. What I learned along the way was, it wasn't my schooling that was my value, it was my intrinsic abilities, my ability to listen, to work in a team, to get along with a lot of people, to get buy-ins from others. I was organized, I was hard-working, and I was ambitious. If there was an opportunity to rise through the ranks for me, it was like a game. I'm like, Alright, this is a corporate game we're playing. The next level is this, this is what's required to achieve that level, I'm going to move towards that.

Andi Simon: Now, the game metaphor should not be underestimated, because you didn't take yourself too seriously, but seriously enough, because we play games all the time. Adults love to play professional games and all kinds of games. But when you said the word game, what came to mind is how I often use games to help people relax. And my goodness, they can create and they perform well as long as it's not serious. And all of a sudden, you found a way of visualizing yourself that said, I can play this game. It isn't really about what I can't do, but I can really play it well. So where did it take you?

Jodi Flynn: Oh, my goodness. So I was in mutual fund operations. And I eventually became the Assistant Vice President of Corporate Quality. I started just opening up new accounts, kind of like anyone who works in a bank or financial institution would. You get the application, enter the information on the system, send it along, and the next one pops up. Very rote. And then it turned into ultimately, I had a job that perfectly suited my personality. It was all about inspiring and motivating other people, bringing out their best even though they weren't in a job that they would have said like, Oh, I dreamed about this from the time I was 10 years old. It wasn't about being in your dream job, it was about doing your best, getting the most out of it. Like forming strong relationships with the people around you and working together as a team towards something greater. And that was incredibly fulfilling. So ultimately, what ended up happening was, I put myself in my dream job even though initially it was just an entry level job to pay the bills while I figured out what I wanted to do.

Andi Simon: No, but you know, both in your book and in the podcast, you're exploring: How do we learn what we are? Because you said it so well, I can't aspire to this job or to be able to help people to be better teammates if I didn't even know that was possible, or in some way, anyone paid for that, or there was a need for it. So this self-awareness piece is not to be underestimated. You had a big mirror going along that you kept looking at and it echoed back. You know, talking about how you help people with their self-awareness, because this is something you're doing now a great deal, right?

Jodi Flynn: And it's all self-awareness. Andi, I'm sure you can relate to this too when you meet somebody who is self-aware versus somebody who is not very self-aware. The results that each one of them is getting is night and day. So self-awareness, as leaders, we're very focused on the people around us. But it starts with you having to understand your own motivations, your own values, your own emotions, and I can't underscore that enough. Emotional Intelligence starts with your own ability to recognize the emotions that you're feeling and managing them. And when you're able to recognize what's going on with you, you're better able to recognize what's going on with others.

Andi Simon: So with my clients I will often say to them, "The success you want, the happiness you want, the life you want, it all starts with you." But when you do have a really good understanding of yourself, it will ripple out and you will find that you intuitively know how to interact with others. Now, do you have a mirror for them when you're working with people or other key little triggers that people might take away from the podcast and say, Ah, I missed that. I haven't really looked at myself with fresh eyes in a while. What do you help them do?

Jodi Flynn: Oh, my goodness there's so much going on, and yes, in the podcast, because my guests like you are just amazing people. I ask the same questions of my guests every time but their answers are all different and the conversation goes from there. I'll have people who regularly listen to the podcast where all of a sudden, I'll hear from them and get an email and be like, This podcast was amazing. When she said this, it totally resonated with me. So I'm drawing out my guests their own experiences.

So my guests act as a mirror for the people who are listening to my podcast as well. I have an assessment that I use in my business. And when people are thinking about working with me, the first thing that I'll ask them to do is take this assessment. The assessment captures their perception of themselves, the people around them and the world at large. And so as we're debriefing their results, I can pick up certain traits that are going on like perfectionism, or focus on the past, or not feeling valued by others, or not feeling very connected to the people around them. It's really a mirror, but it's really meant to be a conversation starter.

Like, here's what it's showing, but it doesn't end there. What's your perspective on this? Tell me about this. Does this resonate with you? And from there, I get stories, and either that's me, or kind of, but it looks more like this. And it's just a tool we can use to get the conversation going, like engaging somebody in a conversation about themselves, like all of a sudden, you know, the aha moment. Like I'm snapping my fingers and those aha moments just start coming up like, "Oh, that's why I do what I do." Oh, that makes perfect sense. You know, type A people who are exhausted. I'm like, are you delegating? "Oh, is that why I feel so burdened and exhausted in my business?" Yes, yes. Because you're doing it all yourself.

Andi Simon: Now, they're successful women. And yet they need a moment where they can think about themselves in new ways. I'm thinking about my own career as we go through how often we get so focused on what the job is to get done, that we never take any time to reflect on how we're getting it done, or whether there's another way to get it done or whether it's not getting done. We're goal oriented and have a path and we're hopping on it and we're pushing forward and looking good, but it becomes important that how do they know when it's a good time to pause and come see Jodi?

Jodi Flynn: Usually what happens is, my clients are in a place where they're feeling like they're just doing too much work in their business, or that their business or their job is eating them alive. To some extent, it's not why they started their business and they don't feel good. It's interesting Andi, when we start working together, some of the same things I see—a lot of perfectionism. I do see a lot of, "I'm so driven for results that I took on these extra projects even when I didn't have time to do it. It wasn't a good idea but I was so driven and I wanted the results, and I wanted the win."

What comes up also is another theme with my women, it's in the podcast subtitle, is self-doubt. It's so interesting with the women I work with, they are successful. If you ask them, "Who in the room is more expert than you at what you're doing?" They'll say, "I'm the expert in the room. I do a better job than all of these people." What shows up in their work is, "I don't know if they'll like this. I don't know if it's good enough." The perfectionism will eat them alive.

So even though in one conversation, they can acknowledge, "I'm the expert, I can't think of anyone who can do a better job than me," on the other side of it, they're overworking themselves. Even though the scope of a project will say they'll deliver X,Y and Z, they're like maybe I should also do A, B, and C, because I don't feel like this is enough. They really want everyone to be wowed with their work, to feel okay.

You know, it's getting them to realize and look at themselves differently. "You are the expert in this conversation. This is who you are, everything you do is valuable." And so as we're talking, I'm having them do exercises, and also just report back in on different meetings and stuff like that. And getting them to recognize that everyone around them also sees them as the experts and are already wowed with what they're doing.

Andi Simon: It's very interesting listening because remember, you had your aha moment when you had a burst of an awareness. And in a sense, you're helping them have their aha moments when all of a sudden these smart people need to have a pause and take a good look at what's going on. In fact, we've all either worked with or had people working for us, or sometimes ourselves, realize that we're pushing the limits, not quite sure where the limits are. And we are convinced that we can, but sometimes it's not necessary. It's interesting.

I've been interviewing women CEOs for a book I'm working on, on how they can turn into great businesses. They do it differently. They do it with a lot of collaboration, a lot of teamwork, a lot of empowerment. And I'm wondering whether you're seeing a difference. I don't want to say those who are successful and can manage it and those who reach a stall point. I mean, is there anything that you're seeing that is interesting, that I should pay attention to as I'm doing my research on these wonderful women CEOs and entrepreneurs?

Jodi Flynn: Well, I'll agree with you that my clients start feeling a lot better when they start collaborating more, and delegating work and outsourcing, and hiring a team member as well.

Andi Simon: That is interesting because that's what I'm finding in the ones who do really well. When one second I can see what has to get done but I don't share with my guys and they go do it, and then they come back and they tell us how they've done it. And we talk about small wins. And then the next thing, and I can see where they have to go but they have to get it done. And it's done in a very exciting way. And our guys all seize control of it. Off they go. And she's fierce. And it's as if each one is telling me a different story along the same lines. They're different sharers, and they don't have to be all things to own. It's just very interesting. Sounds like you find the same things.

Jodi Flynn: Absolutely. I've seen that it looks a little bit different for each person. It's definitely a collaborating partnership, outsourcing. I had one client who when she hired me, she said to me, "I either need to sell my business or bring on a partner. And I've had a partner before and I didn't like it. It didn't go well." And so we kept it open. I said, "Okay, well, let's start and then we'll see where we end up. You'll probably make this decision in the long run." And by the time we were done working together, she did neither. Because what happened was, she started trusting her team. She had done a great job hiring people who knew what they were doing and so she allowed them to do it. She didn't go to the meetings as often. She started letting them meet with clients on their own.

Then there was this one day, we had a call and she had an epiphany that she wanted to share with me and I said, "Well what happened?" and she said, "They're better off without me. I'm in the way when I'm around." And what was really great was, because a couple of meetings before, I had said, "Okay, what are the long term goals? What should you be doing?" She said, "I should be doing visionary stuff. I should be hiring. I should be looking at long term strategy. I should take vacation because I haven't had a vacation in awhile."

So when she had the epiphany that her team did better when she wasn't around, I was like, "Great. Now you have all this time to now do the things that you know you need to be doing as the business owner." That was such a great feeling. And for other people, other clients, it might look like setting boundaries around certain relationships, like resetting expectations.

With relationships and outsourcing and delegating, and teams and partnerships, there's always a time where we need to come back and have a realignment, just like a car. We have to get everything aligned again. Are we on the same page? Maybe we should talk about our expectations, reset them, and that creates stronger relationships moving forward.

So, you know, as we get into that process, it's almost like in the beginning of our relationship when we start looking at relationships. What's it gonna take to get everything in alignment so it feels good? And we might do it a little bit again. What I want them to take away from it is, this is something you can continue to do because now you have the skills to identify when a relationship needs to be realigned and to do the work to get it there.

Andi Simon: Now, I will tell you that you have come a long way from that shy little girl who had trouble talking to people. Even as I'm thinking about my own business that we have grown over the last 15 years from a startup to really successful as a corporate anthropologist helping companies change and as a book author, we're global in nature, and we do a lot of culture change, and we really help people who are stuck. And there's nothing worse than not growing and not knowing how to.

It's just very interesting because when they have their aha moment, like your woman did, all of a sudden you can see their eyes light up. They just saw it with a whole new story and off they go. I get great vibes out of it. It's less about what I do, then how I help them do it. And it's a transformation.

So as transformers, we're coming to wind down our time. We wanted to start at the beginning with the things we want them to hear. But I'd like to end with some of the things we should remind them about. My first reminder here is that these are strong, successful women, but good enough may not be great enough. As you're thinking about where you're going, it might be a great time to do a Jodi Flynn and begin to think through, What am I missing? And how am I doing it? And where do we reflect? What are some of the aha moments you don’t want our viewers to forget?

Jodi Flynn: And you know, Andi, I'm gonna leave them with the basics because this is the thing, sometimes it's too simple for complicated minds. Oftentimes being type A or being ambitious, our minds are so complicated, that we overlook the key foundational things that will actually take us to the success that we desire.

So those things that I want to remind them about is: take care of yourself. You're not going to be successful if you're exhausted and overworked and burdened. Just be active in a way that feels good for you. Eat nutritiously by eating foods that you enjoy eating. Get good sleep, hydrate yourself, all the basics.

Then, pay attention to yourself and your own emotions and how you feel about certain things and your core values and what's important to you. And then I would say, these are really important baby steps that will get you to the destination that you seek. I have a client who told me she actually started implementing some of the things I talked about in the book and she had tripled her business. And I was like, Oh my God, and she isn't in the startup phase.

So right, let's acknowledge it's easier to triple your business when you're in startup phase. But it was still financially a significant amount of money. It was nothing to sneeze at. And I said, "Oh my God, what did you do?" She's like, "I focused on one thing a day. And as long as I got that one thing done, that day was a success. It's one thing every day. And before I knew it, my business had doubled. And then it tripled." And I was like, "That's beautiful."

Andi Simon: Wow. So the lesson learned: Let's focus on one thing a day, if that works for them, might not be perfect for everyone listening, but it is a simple sale. You know, let's not make it too complicated. We don't have to undo everything when we have to make a new you, we just have to slow down and focus. That's a great story. I have had with me a marvelous woman whom you need to know more about. Jodi, how could they get ahold of you, and tell them about where the book is and what your website is, and let's help them find you if they need to.

Jodi Flynn: Yes, my website is You can find all the different social media platforms on there, as well as the podcast and back episodes. And my book is Accomplished: How to Go from Dreaming to Doing and you can find that on Amazon.

Andi Simon: I've had with me Jodi Flynn, who's a wonderful, wonderful woman helping others do better and begin to think about how to dream and not get frustrated about what you can't do. Thanks for joining us at On the Brink With Andi Simon. Our podcast today has been such fun, come back for more. And send any requests or questions for me to You can find more at I look forward to hearing from you. Have a great day.