Bossing Up In Business: Navigating Entrepreneurship with Diann Wingert

Catharine O'Leary: Hey everyone, welcome back to kickstart the conversation. I'm very excited today to talk with my colleague Diann. Diann has a 20 year career as a psychotherapist, and she became a business strategist and coach for ambitious outliers, which I'm excited to find out what that means because as an economist, we talk about outliers all the time. So Diann's passion is helping others unlearn the beliefs and behaviors that hold them back so that they can proudly stand out instead of fitting in using her signature framework, the boss of breakthrough, which I love. Diann has extensive experience with creative entrepreneurs with the strength and struggles of ADHD. She loves dark fiction, strong coffee and laughing out loud, Diann is also a peloton enthusiast, and want to ask about that as well. And practicing Buddhist and hosted the driven women entrepreneur podcast. And Diann and I have been having some really cool conversation. So I want her to come on, kickstart the conversation and share some of her insights. So welcome, Diann, to kickstart the conversation.

I'm delighted to be here and can't wait to dig into the juicy goodness that we've been talking about offline.

Catharine O'Leary: So what we were talking about just now, which was really interesting, I think, because because we've been, I've been having a lot of conversations around when people leave corporate, or people leave a job, right. So they, they have decided that I'm done with the boss, right? I want to be the boss of me. I'm done with having a boss, I'm done with having the structure I'm done with. It didn't really think structure, I don't think I think they just think I'm done with answering someone I want to work on my own schedule I want to work with, you know, the people that I want to work with and so on. And that sounds great. Right? That sounds amazing. But I think that there is and we were talking about a shift in the in the way that that you actually have to set yourself up for the day, or the week or the month or the year when you have to be the boss of yourself. So when you're the boss of you, there's a lot that goes into that, that I don't think people like are right. Like, I don't think that they are buckled up, as we said, for that journey. So let's say what are your thoughts on that? And how people kind of come into it?

Well, I'd love to unpack this with you. Because I think it's we've we've all heard it said that the vast majority of small businesses fail within the first few years. And I've always been fascinated by that. Because for someone to be an ambitious outlier for someone to say, You know what I'm going to do my own thing, I'm going to hang up my own shingle, I'm going to put up my own shop, I'm going to become the boss of me, I'm not going to take direction from anyone anymore. I'm going to decide what I do, how I do it, who I do it for what I charge and all of that. And I think there's a certain glamorization of entrepreneurship that's going on right now, even though we've all heard for years that the vast majority of small business ventures fail. It's also true that 80% of all businesses in the US in particular, I don't know the statistics for Canada 80% of all businesses in the US are sole proprietorships micro businesses. So why are so many people choosing this, when so many people fail at it, and what's causing them to fail more interesting to me is what's causing them to succeed. So I think about this a lot, because of course, the people I work with my coaches, I want them to be successful. I like to be successful. And I like to help the clients I'm working with be successful. So there, there are skills that we need, absolute skills that we need, but I also think there are huge changes in mindset that I don't think we talk enough about what I call think like an entrepreneur, I have learned both the hard way through my own experience. I've been self employed since 2010. I think there's a huge, huge difference, Katherine between saying, I'm tired of having a boss, and I'm ready to be the boss. It's why I called my framework, the boss up breakthrough. Because it's not about necessarily being a boss of other people. If you've raised even one child, you know how to do that, or even a dog, but it's being the boss of yourself is is an internal job. It's a not only a mindset transformation, I actually believe it is a transformation of our entire identity. We are not looking to someone else to hold us accountable for doing hard things for doing things we don't feel like doing for making decisions that are scary and uncomfortable and fill us with dread. We still need to do it because we are literally where the buck starts and stops. And I think people are not always prepared for that. Particularly because I work primarily with women. I think women in the western world are conditioned from a very early age to be good girls, to be polite. To be respectful to raise their hand instead of talking out of turn. And what goes with that is a very strong desire to avoid making mistakes, we want to get the A's we want to be liked, we want the teachers to like us, we want to do well at our ventures. But you cannot succeed as an entrepreneur, if you're not willing to take risks, and taking risks means dancing with the possibility of failure. Women have a really hard time with this. And they don't really know that they do. They attribute it to other things. They'll say, Oh, I can't finish this, because I'm a perfectionist, or I can't seem to push publish on this new website, because I'm a procrastinator. Well, maybe that's so maybe that's so but underneath all that may be a strong determination, not to make mistakes and not to fail, and it is absolutely paralyzing.

Catharine O'Leary: It can be absolutely, and I think that the, you know, like it, as you read through a lot of the books as you're like, I mean, I'm an avid reader, so I'll, you know, consume, all the books were on marketing and sales and anything that I that I can get my hands on. And one of the prevalent, you know, conversations from entrepreneurs that have, you know, done very well, in our seven 810 figures, whatever, like, they had a lot of failure at the beginning, and they still have failures, like they're still failing forward. And, you know, there is, I think that there's a fear, especially when you're starting out, or when you're, you know, like, all of a sudden, you've got, you've got the household on your shoulders, and you've got, you know, the income on your shoulder, and you've got the kids college or, you know, whatever, you can't fail, like there's there's a, you know, like too much riding on it, lose the house, you know, like we can't have like, there's there is no room for failure. And I think that being an entrepreneur, you have to have some room for failure. Not that not saying that you have to like lose everything. But you have to have that mentality to be able to give yourself the grace, that that that you know, that launch didn't work, or that lead magnet didn't work or that you know, that product just you know, didn't didn't sell and then you move on, you learn and you move on and fail forward. But I think that that's, that's hard to to get your head around. I think sometimes it's an

inside job. We have to go under the hood and tinker around. And I do a lot of strategy work with my clients. But I also do a lot of mindset work because nearly every human being has doubts about their competency has doubts about whether they can see things through a lot of the people I work with have ADHD. So they have doubts about being able to be consistent at something even something they love. And nobody wants to make glorious mistakes in front of others. But I think by giving ourselves permission to screw things up without that meaning that we are a screw up without looking for evidence that because I made a mistake, or a series of mistakes, or many mistakes, even the same mistakes more than once like, oh my gosh, I'm not even learning from experience. If we could just observe that as these are growing pains. This is the learning curve. If you study or read the biographies of very successful entrepreneurs, you find out that many of them failed at multiple companies not just launches or products that multiple companies, some of them have gone bankrupt more than once. And they finally succeeded. So I think there's a certain amount of grit and determination and commitment to see it through whatever it takes that many people I think a lot of this really isn't our fault. Okay. I think there's a certain glamorization of entrepreneurship in the last decade. And I think especially targeted to women, by women, like high profile. You know, what a friend of mine calls web celebs and, you know, celebrity entrepreneurs, the way they market, what they do their courses, their programs, their masterminds gives people the impression, Hey, give your boss the middle finger, come on over here into the entrepreneur, entrepreneurship pool. It's easy, it's fast. It's fun. It's lucrative. You will be making money in your sleep and literally anyone can do it. Come on into my program, I will literally take you by the hand all the way to the end. What they don't tell it's probably in the teeny, teeny, teeny, teeny teeny print that their lawyers make them do. Results may vary. And the honest truth is that less than 3% of people who buy into these programs accomplish the desired result. Why? Because it's a whole different way of thinking. And we have to be able and willing to accept full responsibility for our consequences, not say, Well, I paid so and so $20,000. So if I didn't get the result, it's on them. If that's the way you're thinking, you're not quite ready to think like an entrepreneur, like I teach a concept that I call radical self acceptance. And it's, it's a simple decision. I choose to accept myself, regardless of the results I accomplish. And the results are just data. And if it's a success, I'm going to continue to do it. If it's not, I'm going to take an objective look at it and determine what needs to change. So I can try again. But my self esteem, my self worth my agency, my competency, my ability to be a successful entrepreneur is not up for grabs. It is not tied to any particular result. And I'll tell you, I think this is a message that people are really hungry for, because one of my most popular episodes of the driven woman entrepreneur podcast, is an episode titled lessons from a failed launch, I really did not want to record that. And I sure didn't want to share it. People loved it. I have never gotten more DMS on anything, because they said thank you for normalizing how it feels when you screw up and how important it is that we normalize that and acknowledge it and talk about it and say, yep, that happened. And this is what I'm doing now.

Catharine O'Leary: And I think that's, that's super important in that you can't tie your self worth and your, you know, your intelligence level, like, you know, like, I mean, it drives me bonkers. It's like, Well, I obviously can't do this. Like, I mean, like, that didn't work. So it's me like I obviously like it's something in me that can't do it. It's like, well, hold on, like, like, did you have the right target audience? Did we have the right mechanism? Did we have cold traffic? warm traffic? Did you have jayvees? Like what like, like, there's a ton to look at. Before you ever make that decision. I think that that's what, you know, like, if you really high up in corporate, those are the kinds of things that you actually look at when, like a CMO who doesn't look at the advertising for Superbowl or something like that and say, Oh, well, you know, it's me. Obviously, that didn't work. We didn't like generate, you know, millions of dollars. Well, that's not what they say. Right? They they say Okay, give me the analytics, how many? How many people watch the show how many people watch the episode, how many people? Like there's a whole there's a whole framework to analyze the information because it's just information. It has nothing to do with your like your actual identity. And I think that's that's super important. Because I hear people all the time saying, Oh, I tried, I tried to do an online course it didn't work. So it must be me. Wait a minute. Is that the topic? Did you find your like, were you were you niche down enough? You know, were you were you targeting the right people? Like, you know, like, there's a lot going on in that before. Before you jump to its me. In fact you should never jump to is me is what you're saying? If

there's let's put it this way, if you if you want to beat yourself up, like Be my guest, but I just don't think there's anything good that comes from it. I don't think I think when we are blaming ourselves, shaming ourselves, shutting ourselves, we're doing any of this stuff, feeling bad because things didn't work out the way we want it. I mean, a be disappointed. It is disappointing when you spend a ton of time and energy and effort and opportunity cost and focus and attention. And it doesn't work. But feel the feels I do I do not believe that we should just gloss over it and just move on to the next thing because you will burn out with that, like feel the feels. Take a little time, have a little tantrum, don't go public with it. But feel the feels and then get curious. I am very fortunate that I encountered Buddhist teachings about 20 years ago. And what I've learned from that about mindfulness has really served me well in my own business and then the work that I do, because mindfulness, you don't have to change your religion. You don't have to shave your head and start sitting cross legged on a cushion and trying to make your mind go blank. That's not That's not what it is. Being mindful in your business is simply this. Be open, open minded, be curious and be non judgmental. And when you think about applying, openness, curiosity and non judgement to why this didn't work out. Instead of thinking I knew it, I'm a loser. You'd be surprised. I mean, I think in fact, I think curiosity is one of the most important qualities that I look for in someone, you know, who is moving into an entrepreneurial venture, because instead of jumping to conclusions, or having knee jerk reactions to things, it's like, Well, hey, I wonder why this thing that I worked so hard on, didn't play out the way I thought it would like, I wonder what happened. Instead of seeing that as evidence that you don't know what you're doing. Now it's possible there's a skill gap. I'm not saying that when when things don't work out, it's never your fault. It may be a skill gap, you might need to hire some help. But it's never a good idea to blame yourself. Because that literally takes the Creative Problem Solving our brains are more than capable of and disables it. When we are feeling strong, negative emotions. It's like when you're feeling shame, guilt, fear, just all the yucky stuff, which is part of being human. But when you're feeling the things about yourself in your business as a result of a decision you've made, it literally disables your creative problem solving, your objectivity, your logic, your rationing, your reasoning, and you need those things to come back online, so that you can fix the problem. Once we get hijacked by our emotions, especially negative emotions, we need to steer clear of making any additional decisions from that fact, I tell my clients when they, for example, they pitch a client that they were certain was going to hire them. Yeah. And they're really eager. And then they get ghosted, or they get a no. And they kind of tumbled down the spiral. I say you need to stop, drop and roll. The minute you have a disappointing outcome, you're going to get hijacked by your emotions, you're going to start thinking all kinds of negative crazy things, you're no good to yourself or anyone else. Stop what you're doing. Drop the ruminating, and go move your body, I don't care. If you do push ups, sit ups, run with your dog, do a dance party in your living room, move your body because that will help you process the negative emotions and circulate them and get them out so that your rational mind can start coming back online to help you figure out what to do next.

Catharine O'Leary: And I think that this is this goes back to being the boss of you. Yeah. So. Right. So because now you have full accountability, and, and responsibility for how you proceed forward in the day. Because if you're working for corporate and you have, you know, like the pitch doesn't go well with a stakeholder or maybe with a customer, you have to go back and analyze the information because you have to report it, you have to say, Okay, well what happened? What can we do better? I mean, the higher ups are actually expecting that, when you're your own boss, there is no higher up, like you are the higher up. So how, how do you, you know, like, that's where the, and we talked about this a little bit where entrepreneurship is probably the the largest personal development, you know, path that you'll go on, or journey that you'll go on. Because you do have to be the boss of yourself, like, totally, you have to, you know, you have to decide when you can take sick days and, and, you know, vacation days, and you know, all that like what your schedule is going to be. Because sometimes it's easy to say, Oh, I don't feel like working today. But there are repercussions for that. So and it's also easy to say, You know what, that didn't work. I'm That's it. I'm out. Like, I'm out, I'm out for the week, I'm done. Like I can't even well, that has some repercussions. So you know, like that, that mental shift of getting into, okay, hold on, I can have my temper tantrum. And I agree, don't do it, you know, online, but you know, then how do you get back on the horse? I guess? How do you how do you, you know, how do you make sure that you keep going? And I think that's where you know, the why of what you're doing and the vision of what you're doing comes into play. There's so many things

in business that are scary. It is scary. Sometimes it's not scary to launch. Sometimes it's really exciting and sexy and glamorous, and that you feel you're filled with optimism and anticipation of future success and riches and all that because you have no experience to inform you that that might not happen. So I think it's I think this is one of the reasons why there's so many serial entrepreneurs, because at least my personality type and especially anyone who identifies with ADHD traits, or ADHD ish. The beginning is the most exciting part because you fall in love with this idea that you have, and most people will start a business, most women in particular will start a business based on passion and purpose. Yeah, not not because they're anticipating how much money they're going to make, they often have, they're passionate about anything from teaching people how to groom their own dog, instead of taking them to, you know, a salon, or teaching people how to better manage their finances. So they are something that they are passionate about sharing with others, and they want to get paid for it or something they feel a sense of purpose about, and those are their drivers. But one of the mistakes a lot of women in particular make and oftentimes, highly creative men as well, is that we don't factor in the other two piece that I think are absolutely crucial. And that is planning and profit. You know, just because you're really excited about something and you just can't wait to share it and you're all fired up. But you if you don't have a plan, it's not a matter of if it's a matter of when you're going to get stuck, you're going to reach what I call the messy middle and it might come actually, pretty soon after the launch, you're going to feel stuck, you're going to feel confused, you're gonna feel doubt. And a lot of people at that point, just think, well, I've sort of lost my mojo, like, I'm just not feeling it right now. So maybe this isn't the right thing. And they hop on to the next thing. This is very common for people with ADHD. So they have multiple starts. But no, you know, no sustaining. And it's oftentimes if we just start with passion or purpose or both, but we don't have a plan, and we haven't worked profit. And because it is a business, it's not a hobby, it's not a charity, and it's not something to fill your time. It's like if it's a business, then you need to make a profit. And if we don't understand how to do that, or why that's even necessary. We're really handicapping ourselves from the very beginning. And it's sadly very common.

Catharine O'Leary: Yeah, and, and I think that this also goes to, like, even like, not like leaving a business starting another one is leaving a strategy and starting another one, like, yeah, Facebook challenges didn't work. So now I'm gonna go to this or this didn't work. Now I'm going to go to the tick tock, and I'm going to dance on tick tock, or I'm going to do like, and the thing is that, and I can't stress this enough, there is no silver bullet here. It's it's all about consistency and working your message and making sure you're being clear, concise, and that you've got an ideal target audience that's really niche down. Because if you have that, then you know, then you can work with the launch that didn't quite work. And you can figure out why. And you can start, you know, tweaking some things. But just jumping from one thing, like one, you know, one pot into another is not going to help you.

And it's oftentimes how people spend their first few years being an entrepreneur because they buy into the glamorized version of having your own business because it sounds easy, and it sounds fun, and you don't have to have a boss anymore. And you're gonna make money in your sleep. And like Who wouldn't love that. But we're not really prepared for the actual rigor for the actual risk tolerance that we need to be able to look at the data that we create and do what I call separating math from drama. Math is neutral math has no opinion, math is not indicting you as a human being, as having high worth or lower your math doesn't care. Drama, is all the stuff that we tell ourselves about what the math means. And I think, you know, it's a harder sell, I think, telling people the truth, telling people, they actually need at least a rudimentary business plan, they actually do need a profit plan, because that's flying in the face of all that they're hearing from these high profile celebrity entrepreneurs. I just don't want to see people fail, especially women starting a first business after 50, which is a very rapidly growing group for all kinds of reasons. Because there's less margin for you recuperating from a loss. I want to see them especially women who've been wanting to have their own thing for years, sometimes decades waiting for the kids to grow and leave. Now it's my chance, it's my turn, I'm gonna do the thing I've been wanting to do for so long, but they're not set up for success because they've been sold a bill of goods that is not based on realistic expectations. So I'm going to keep on telling the truth that there are things that you need to do and maybe they don't feel sexy, or fun or exciting or glamorous. But if you don't do them, you're gonna be feeling more pain and suffering down the road. I guarantee it. It's just it's

Catharine O'Leary: just foundational stuff. Really. I mean, like it You know, you build, you build a strong foundation, you can build up from there. And you know, like it can, and we were talking about this, like, if it's not your zone of genius, and you don't love doing and then outsource it, like don't know, you know, like, you don't have to do it all by yourself. That's that's not what, that's not what the intent is actually, we we want you to do to bring in people and bring in the help that you need. But you do need the foundation in order to move forward. Because if you don't have that it is going to crumble, there are going to be cracks and things are going to, you know, then you're going to end up with like what I call duct tape and bubble gum in the messy middle. Trying to keep it all together because you don't have the customer experience, you know, journey really mapped out or you don't have the fulfillment really, you know, scaled up the way that you need to so just, you know, set yourself up for success and do some of the some of the foundational work and you'll go a much you know, it'll help it'll help your failing forward a lot easier, I think, yeah, and

buying another course enrolling in another program, joining another mastermind, or starting another business or constantly switching tactics, that's never going to fix a lack of foundation problem. So if you were if you really want to have your own business, if you really want to boss up and learn how to be the boss of yourself, make the decisions, take the responsibility and enjoy the benefits. Yeah, there are some steps that even if you've been in this, and I think this is really important for people to hear, even if you've been at this for a while. And I've certainly known quite a number of people who started their business with literally a wing and a prayer, they had no idea they enrolled in program after program worked with Coach after coach tried tactic after tactic. They're now five years in, and they're still not making a profit. And their spouse, if they have won has given them a strong side eye and saying, if you don't start making money with this thing, you're going back to work. It is okay. If you've been doing everything wrong, if you've been like literally dabbling for years. But you've reached a point where you're like, but I still want this and I'm ready to lay the foundation instead of like trying to build things on something that isn't solid, and it's never going to hold, you can still turn things around and all of your past mistakes will actually inform your thinking about how to do better in the future. Sometimes, I used to say I'm one of those people who always has to learn everything the hard way. And I think there's a lot of us out there. And as long as we can be open to that, be curious about it and refuse to judge ourselves. You can turn it around at any stage of the game. So you don't have to throw in the towel. Even if you feel like oh geez, this is me. Okay, great. Yeah, this is good news. Because now you know what to do.

Catharine O'Leary: Exactly. Diann, this has been a fantastic conversation. How would people find you or get some more information about what you do? And how, how they can work with you.

I like to tell people, if you like the sound of my voice and what I have to say with it, you should check out the driven woman entrepreneur podcast. And I have a quiz called What's holding you back? If you are struggling a little harder than you think you should be. And you're not quite sure. What is that one core pattern of belief and behavior that's really getting in your way you could take the quiz, then you'll get a follow up series of emails with a bunch of resources for just that specific problem. And I think you already have the link so you can include it in the show notes. Absolutely.

Catharine O'Leary: I have the link and I you know, I love my quiz. So I've already taken So Diann, what what's kind of the final words that we should be leaving our audience with what what would you like people to walk away and, you know, kind of be able to think back and say, Oh, that that was the thing that I needed to know.

I think the most important thing is what I mentioned earlier about radical self acceptance. No matter how many times you've screwed up, no matter how many times you've made mistakes, no matter how much fear, uncertainty and doubt FUD you may have about your ability to be successful as an entrepreneur. If you practice radical self acceptance, the way I described it, you make a decision, you make it one time, and then you just keep practicing it. You can steer clear of a lot of the mental suffering that keeps us stuck and repeating patterns that are never going to change until we do something different. Yeah,

Catharine O'Leary: I love that radical self acceptance. So thank you Diann, for being on kickstart the conversation and to everyone out there listening. Stay curious and ask a lot of questions and you know, connect with your ideas. clients with that curiosity it will take you a long way we'll see you next time