Three Marriages, Three Careers, One Religion Change: Diann Wingert on Continuous Evolution
What have you outgrown? A job, a marriage, a whole belief system? My guest this week, Diann Wingert, has outgrown all three. Three marriages. Three careers. A full change of religion. And she wants you to know that isn't a failure, it's the whole point.
Diann spent years building a successful psychotherapy practice before she became impatient with a specific kind of conversation, the one where a client is more attached to their problem than to actually changing it. So she became a business strategist instead, built her Boss Up Breakthrough framework, and started helping ambitious business owners stop chasing generic six-figure formulas and instead build something built on their own specific gifts.
Diann calls the cultural default pick and stick: pick your person, your career, your lifestyle, and stay there until death or retirement, or you've somehow failed. She rejects it outright. When she left her second marriage and her Christian faith in the same season, she lost nearly every friendship she had, and the harshest pushback came from other married women who told her, in so many words, who do you think you are that you deserve better than the rest of us.
She isn't alone in walking away from something that was merely fine. Research from career-change firm Careershifters found that about a third of professionals aged 45 to 54 expect to make a significant career change before they retire, and the leading reasons in 2026 are an unhealthy work environment, poor work-life balance, and a values mismatch, not pay. Diann's own pivot followed the same pattern: not crisis, just the slow, growing discomfort of staying somewhere she'd already outgrown.
If you're sitting in a job, a relationship, or a belief system that isn't bad enough to justify leaving but isn't you anymore either, this episode is permission to stop measuring your life against everyone else's threshold for misery. As Diann puts it, this isn't a competition about who can sustain misery longer.
TRANSCRIPT:
Erica: Hey, girl. By now, you know I have Her Collective, my online community for ambitious women who are done doing it alone. Her Collective is for the women who are smart, capable, and driven, but they find themselves stuck on the sticky floors like self doubt, burnout, and waiting for permission that quite honestly never comes. Inside HER, you get more than motivation. You get real support, real strategies, and real momentum.
Erica: We work on things like clarifying what you want now and what's coming next, building confidence without burning yourself out, navigating hard conversations, career moves, and leadership moments with clarity, and surrounding yourself with women who actually get it. This isn't about hustling harder. It's about moving intentionally with the right tools and the right people in your corner. If you're ready to stop spinning, start choosing yourself, and build a career in life that actually feels aligned, I'd love to welcome you inside her collective. You can learn more and join us at www.joinhercollective.com.
Erica: Because honestly, girl, you were never meant to do this alone. What have you outgrown in your life? Has it been a job? A whole ass career? What about a marriage?
Erica: Well, guess what? I'm here to tell you that if you have outgrown any of those things, or any other things for that matter, it's absolutely okay. In fact, that's great because today's guest, Diann Wingert, is a former psychotherapist turned business strategist. And y'all know those psychotherapists, they go deep. This might be one of my favorite episodes of all time, and I am officially obsessed with this woman because she is all about continuous personal evolution, which, oh my god, we all need to be doing this.
Erica: And if you are truly doing that, it might mean that the job that was once perfect for you isn't anymore. And that might be true of your marriage. It might be true of your friendships. But what you are going to learn today, and what I know to be true, is that each person's journey of continuous evolution is different. But with Diann, she helps us make sense of this journey.
Erica: And she is going to talk all about living with the integrity of yourself, the sticky floor of shame and outgrowing things, and so much more. Y'all, today, I have former psychotherapist turned business strategist and coach. She helps ambitious outliers do business their way. Diann, I am so pumped that you are here.
Erica: Welcome.
Diann Wingert: I'm so glad to be here, and this is gonna be an awesome conversation, guaranteed.
Erica: Oh, absolutely. And here's what I love. So we talked one time and just totally vibed and connected on all levels, and I know that we're gonna cover so much ground today. But I wanna start by just fill me in. Who is Diann?
Diann Wingert: Well, my relationship status with myself is it's complicated. I've had three marriages. I've had three careers. I've even changed my religion. So I am a person who is, let's just say, unlike most, not resistant to change.
Diann Wingert: I love being on the path of continuous personal evolution, and, it keeps life interesting and exciting, but it does keep many people confused. Like, who are you now? And I'm like, buckle up, but don't get too comfortable.
Erica: I love this who are you now question, though, because if you had asked me who I was, like, I don't know, six months ago, you'd probably get a different answer.
Diann Wingert: It's so true. And let me just say this, that I think our culture unconsciously programs us to do what I call pick and stick, which means pick your person, pick your career, pick your lifestyle, and stick with it. And if you don't make it all the way to the finish line, aka death or retirement, depending on what your goals are, you somehow screwed up. I completely reject that.
Erica: I love that. To grow. Well, it gives you freedom. It gives
Diann Wingert: you so much freedom, and you're
Erica: not I mean, I hate to use the word married, but you're not married to anything. You know?
Diann Wingert: Right.
Erica: Gives you this ability to just say that's no longer working for me anymore.
Diann Wingert: Exactly.
Erica: On to the next. Well, what I am really curious about is how did you make this move from psychotherapist to business strategist? Because that is a big jump.
Diann Wingert: You know what? It's not as big a jump as you might think because I realized it it again, I think this whole concept of the continuous personal evolution, I've really come to understand, accept, and embrace is simply my life story and the life story of many people if they allow it to be so. But going back to what I said earlier, you know, you you go to a lot of trouble to become a therapist. It is literally not an easy path. Obviously, you have to have a bachelor's degree, then you either have to get a master's degree or a PhD.
Diann Wingert: Throughout that whole process, you are practicing under supervision. Once you finish your graduate school education, then you start collecting clinical hours. You have to have at least 3,000 of those before you can sit for your first licensing exam. And if you pass that, and the pass rates are about forty percent, months later, you get to take the second exam, and you have to keep re upping every couple of years. So it's a difficult path.
Diann Wingert: And considering most therapists are not paid well relative to that amount of career preparation, like, after going through all that, why would you give it up? The simple version, Erica, is this. I reached a point in my life where even though I was an excellent therapist, I had a very successful private practice, cash pay, and my clients loved me. But I started becoming impatient to have different kinds of conversations. And what I mean by that is I'm a really good problem solver, but some people who seek out therapy are a lot more attached to their problems than they actually realize.
Diann Wingert: So even though they allegedly want to change, they kind of are stuck to their story. Now I know you talk a lot about sticky floors. We're gonna get into my sticky floors later on in the interview. But I kind of realized that in my own life, I didn't wanna think about the past anymore. I didn't want to even reference the past as having any relevance to where I was now.
Diann Wingert: So I started becoming a little bit maybe impatient with some of my clients and thinking in my mind, my thought bubble, are we really still talking about this? And I wanted to move them forward to thinking much more about the future. And I've heard a lot of coaches who don't have the background I have say, well, here's the difference between coaching and therapy. Therapy is about the past. Coaching's about the future.
Diann Wingert: That is a gross oversimplification, but it does have a negative truth, which is therapy is focused on insight and healing. I came to believe that once you have enough insight to live your life in a better way and you've done the healing work, so now you have scars but no longer scabs or open wounds, therapy is no longer the ideal modality to move you forward. As a matter of fact, you're more likely to just keep spinning your wheels and staying in the same place, but referencing the fact that you used to be so much worse that you're actually still doing great. And I wanted to move the conversations I was having with people from problems to potential and possibilities. And so that's why I became a coach.
Erica: So I love this on so many levels because in my first career, I was a personal trainer. And everything that you were saying about, like, getting impatient with people resonated because I would see the same people for years, and we would never progress because they weren't doing the work they needed to do to move forward. Right? They weren't getting out of their own sticky floors. And then you talked about therapy being insight and healing.
Erica: And this is what I love about sticky floors is because the more in tune and more insight you have about them, the faster you can move through them.
Diann Wingert: You can move through them. Yes. But here here's the difference. This is some one of the things that you and I have in common. It's not enough for me to teach people things they don't know.
Diann Wingert: It's not enough for me to inspire people to do things they haven't done. I actually want them to take action, get uncomfortable, expand their comfort zone, realize that there are things they are capable of that they've never tested out and then start getting hooked on that. And we're talking about far fewer people who are able and willing to do that. And I wanna be very clear because I have no disrespect for therapists or therapy. It is absolutely life changing and life saving if you are addicted, you are dealing with the effects of abuse, you are dealing with the effects of loss.
Diann Wingert: Like, these are the kinds of things, and there are others that you require a healing modality based on insight and healing. But once that work is done, if you keep using that tool, you fail to progress. And I think coaching is about growth and change. And for that, you have to take action. So anyone listening who thinks that going to see a coach or working with a coach or collaborating with a coach is about learning, it actually isn't.
Diann Wingert: It is about implementation because that's where the magic happens.
Erica: And this may be me just not fully knowing the requirements of a therapist, but can a therapist play the part of both a therapist and a coach to where Yes. If they've helped somebody heal, can they then move into the progression piece, or does that kind of violate the the terms?
Diann Wingert: Such an astute question. I don't think anyone who's interviewed me and asked about this topic has inquired about that. So I'm I'm really excited it was you. Here's the thing. When I decided to move away from being a therapist and become a coach, I was still in the state of California.
Diann Wingert: We subsequently moved to Oregon, where my license would have been invalid anyway. But my professional liability insurance said, you still need to maintain this coverage because even if you put your therapy license on inactive status, the fact that you have been a therapist means for the rest of your working life, whatever you call yourself, you will be held to a higher standard of accountability, responsibility, and liability. So what that breaks down to is, yes, if you're a licensed therapist, you can incorporate coaching into what you do, and you will be, you know, covered under your professional liability insurance. So you might say, okay. Well, then why didn't you just stay a therapist to coaches?
Diann Wingert: And here's why. Therapy has an established market value. In every community, the insurance people, you know, if you if you're on an insurance panel, they will say, this is what an hour of therapy in your community is worth. There is a standard. If you want to move beyond that income ceiling, that sticky floor for your income as a therapist, you're gonna have far more challenges doing so because therapy's been around for a hundred years.
Diann Wingert: People are familiar. They know what they know what they think therapy is and what therapy's for. And so if you are a therapist who coaches, you will have trouble asking for more money for that service because they're still seeing you as a therapist. And what's also true is that I think many coaches these days are practicing therapy without a license and without the professional training, and they don't even realize it, especially life coaches. Like and I've even heard many well known life coaches say coaching is the only thing anyone needs for optimal mental health.
Diann Wingert: Irresponsible lie, okay, in my book. I'm very direct. But, I do think a therapist can coach. A coach should not do therapy. It's a little bit more constraining if you are trying to do coaching under your therapy license.
Diann Wingert: It is covered. Coaching is covered as a modality for helping under the therapy license. But I would question why someone would go to a therapist who actually wants coaching. Maybe because they would feel safer, because they know this person is legitimate. They know this person has gone through a rigorous process.
Diann Wingert: There's a greater level of maybe trust, respect, a feeling of safety. But I still think it's preferable to do what I've done, which is to let the therapy license go, but let people know that when they hire me as a business coach and strategist, they're getting all of the wisdom and knowledge about human behavior and human, like, challenges that a therapist knows. For example, you know this because you're an entrepreneur. Entrepreneurship is like the ultimate personal growth challenge Mhmm. Because every fear you've ever had, every limiting belief you've ever indulged in, all of your unhealed family trauma
Erica: Oh, bubbles
Diann Wingert: up. Dealing with authority figures, sibling rivalry, like, all of that stuff, it all comes to the surface. So I think it's an unfair advantage in a way to be a business coach who understands that far better than most. It certainly helps me.
Erica: Interesting. Very interesting. I love it. Alright. So you've led me directly to the talk about sticky floors.
Erica: And, I mean, we're talking three marriages, changed religion, changed occupation. What are your sticky floors? I know it probably sounds anywhere with this conversation.
Diann Wingert: Oh, and I just opened it right up. Here's the thing. I used to be embarrassed about those things. I used to be ashamed about those things. Thank you.
Diann Wingert: To allow the fact that other people would have and will judge me for those things. Like, well, why would I trust you? Why would I respect you? Why would I hire you if you can't keep a marriage together? If you have abandoned your Christian faith, if you have just go down the list.
Diann Wingert: And I believe that I reached a point in my life where what I thought of me was so much more compelling than what other people thought of me, might think of me, or I was afraid they did think of me, whether they ever shared that knowledge or not. I felt like I was not living in integrity with myself to continue and maintain some of the choices that I had made. And I think it's honestly quite unfortunate that because of the length of human lifetime, we are forced to make the decisions about who we are, what we want, how we live, who we decide to share life with, whether that will include children or not, what our income requirements are going to be, what our occupational path is going to be at an age and stage when we can barely find our ass with both hands in a rearview mirror. Like, it just takes longer to grow up and develop and self actualize and really know yourself. And by the time that happens, we've already checked all those boxes.
Diann Wingert: So for me, I wanna be clear. I'm not reckless. I you could tell by the way I speak. I think deeply about things. So I was not just recklessly going from one marriage to the next, one decision to that.
Diann Wingert: My first marriage was five years. My second was fifteen. The current marriage I'm in, I've been with this man for twenty six years. So I got better at choosing. But what I also got better at, and this relates to career choices and even the choice to change my faith, they happened slowly over long periods of time of growing awareness about the discomfort between what I had decided and how that decision played out over time.
Diann Wingert: It may sound arrogant, but I'm willing to accept that as a possibility. I believe that I have outgrown things that used to suit me really well and no longer did. And believe me, I am a creative problem solver, and I tried everything to make it fit or to alter it so that it could fit my new reality and only abandoned it when that simply was impossible. But I did say yes to change, and I still do, and I always will. So what are my limiting beliefs?
Diann Wingert: You know what? I'll I'll tell you what. I am not afraid to disappoint people. I am not afraid to take risks. I am not afraid to fail.
Diann Wingert: Of course, I try to avoid all those things to the best of my ability. But I think at this point and I've had a lot more sticky floors in the past. At this point, I would say the perpetually sticky floor for me is that I still think I take a lot longer than I'd like to to implement change once I recognize the necessity of it.
Erica: Hey there listeners. If you have ever felt like you're stuck in a place, held back by self doubt, perfectionism, or that pesky inner critic, you're not alone. We all face those sticky floors that keep us from reaching the heights we dream of. But guess what? It's time to shatter those limiting beliefs and toxic behaviors to uncover infinite possibilities.
Erica: My book, Glassy Leads and Sticky Floors, is your ultimate guide to smashing through barriers, overcoming limiting beliefs, and stepping into your full potential. This book has been endorsed by none other than the great Mel Robbins, best selling author and motivational powerhouse. It's also been featured in Success Magazine, so you know it's packed with insights that work. Inside, you'll find real life sticky floor stories, practical strategies to help you navigate your own sticky floor moments, and a whole lot of inspiration to keep you climbing. This isn't just a book.
Erica: It's your road map to success, confidence, and freedom. Grab your copy of Glass Ceilings and Sticky Floors today at www.ericaandersonrooney.com. Whether you're in the boardroom, the classroom, or just starting out, this book is for you because no one, and I mean no one, deserves to stay stuck, no one deserves to feel small, and you have glass ceilings to shatter. Let's do this. I mean, that's got my wheels turning, Diann.
Erica: I feel like you've gone through more change than a lot of people that I know, and I mean that in a good way. Right? Like, the way you just framed everything to me, it sounds amazing, honestly, because it's in if it is not fulfilling me, if it is not bringing me joy, if it is not bringing me happiness, it's not for me. And I think so many people sit and stay in marriages, in careers, in situations because they are not that
Diann Wingert: bad. And Yes.
Erica: I don't know if your situations were that bad, but
Diann Wingert: No. No. Actually actually, they weren't. And that was the biggest shade that I got. I mean, when I left my previous marriage, I left the Christian church at the same time.
Diann Wingert: It was it was it was necessary. And I will tell you, I lost every relationship I had, and I even needed to move to a different community. And what was I mean, I even got hate mail from other Christians, which was like, wow. That's really disappointing. But the biggest surprise to me and, actually, when I think back, it it really shouldn't have surprised me.
Diann Wingert: I think it was more just just a profound level of disappointment. Most of the feedback that I got was from other women who were also married, who were also in careers, who felt like he doesn't cheat on me. He's not an addict. He's not a gambler. He doesn't beat me.
Diann Wingert: So, therefore, on the balance sheet of all the ways that this could be worse, my marriage is good enough just as you said. And and the shade I got from other women is, who do you think you are that you deserve more or better than the rest of us? And I'm I mean, if if it had happened one time, I would have been like, bitter, but it happened multiple times. And I realized that when we allow ourselves to evolve, it is so fucking threatening to unhappy people. Because how dare you give yourself permission to uncheck a box, make a change, disrupt your life because you believe that you deserve and can find or create something better.
Diann Wingert: I'll be honest with you, and I probably that that probably was perceived as arrogant to them too when they said, who do you think you are that you deserve better? Like, my marriage is is mediocre, and you don't see me getting a divorce. And my career is fucked up, but you don't see me making a change. And I said, with all due respect, I didn't think about you at all. Like, my life and the changes I made, this isn't a competition about who can sustain misery longer.
Diann Wingert: Like, it did not occur to me that I should compare myself to anyone else and what they may be going through because it's my life. The only people I considered were the people I was working with when I changed careers, the people I would no longer be I mean, I lost all my therapist friends when I became a coach because they thought I was going to the dark side, and I'd sold my soul to the devil. But, when I left my marriage and I and the church, I was a total like, they all rejected me, and that was a huge loss. But the people I considered were my then spouse and my children. Nobody else.
Diann Wingert: It's not a competition sport life, this life thing, you know? And and it wasn't that I was looking for happiness. I just really couldn't be myself and live in a way where I actually felt like me. I felt like I was just wearing a mask and performing so that I could fit in with everyone else, and that that became extremely painful.
Erica: Well, here's the thing. Number one, people who are doing the work to evolve and to better themselves or people who are further along in a success journey than you are are not going to say those things. Right?
Diann Wingert: People So true.
Erica: Fantastic fucking relationships are not gonna look at you and be like, well, I hope that she doesn't cheat on you, so why don't you just say? No. They're gonna say you need to go after what you deserve and what you want and what makes you happy. Right? And I think too, after hearing everything that you said, is that there is such a level of self love that you have for yourself that I think so many people are missing.
Erica: That love is what has really rooted you in a lot of your choices, which I just think is amazing.
Diann Wingert: It's so funny because I've never thought of it that way. As a matter of fact, because I had an abusive childhood, I became an expert at tolerating my own suffering. And sometimes I wonder if I didn't use up my capacity for that because of everything I endured growing up, and I simply didn't have the resources to continue doing that. Also because I I evolved from Christianity into Buddhism. And one of the primary tenants of Buddhism is nonattachment.
Diann Wingert: That suffering is a result of attachment and clinging. And I, in many ways, interpreted that to mean as I continued along on my Buddhist journey, not just being attached to possessions and people, but being attached to identities and who we think we are because that's all a construct anyway. So if who you think you are is all made up, it's very likely that you're indeed someone else if you start stripping away those layers. And that was a big part of the journey too. Yeah.
Erica: Absolutely. Oh my gosh. This is probably one of my most favorite sticky floor stories of all time, Diann. I'm gonna rank you right up there in one of my top favorite episodes. But before we run out of time, you are such an amazing business strategist.
Erica: I know you have this boss up breakthrough framework, and I wanna hear what is this how can we utilize it because it sounds great.
Diann Wingert: Awesome. Well, I talk about this on my own podcast, the driven woman entrepreneur, but you do not have to be a woman or an entrepreneur to benefit from using the tools in the BossUp breakthrough toolkit because, women who are in their careers and men who are in careers or entrepreneurs can use them. The bottom line is I created it as a result of working with many self employed people over time. Some of them are independent professionals, attorneys, physicians, physical therapists, other psychotherapists, people who've, you know, gone into their own business, but it hasn't really fulfilled its potential as a business because they haven't fulfilled their potential as the business owner. I was sick to shit of all the generic cookie cutter advice that's being given by so many business coaches.
Diann Wingert: It's like the six figure this and the 7 figure that and the secret to this, and all you have to do is that. I think the prevailing message out there is you need to be an entrepreneur. If you work for someone else, you're a dunce. Okay? You're a loser.
Diann Wingert: Like, you need to be an entrepreneur. Like, that's the only way you can have self respect. And why wouldn't you do it? It's easy, fast, fun, lucrative AF, and almost completely passive. Like, you will literally make money in your sleep.
Diann Wingert: Come on. What are you waiting for? And the truth is the vast majority of people who start their own business expecting that are not only gonna get nowhere near the promised land. When they don't, they're gonna blame themself. So what's actually wrong, in my not so humble opinion, is the message.
Diann Wingert: Entrepreneurship is hard work. You have to expect that. You have to be okay with that. You have to be willing to do that. And the hard part is that there is no perfect plan.
Diann Wingert: There is no proven process. There is no five step, 10 step, 57 step. There is what is right for you with your gifts, your talents, your goals, your values, your background, you know, and how you craft that into a standout, sought after business that is built on your unique brilliance. That is what the BossUp breakthrough is for. It is for people who already have a business, who have already attempted to be successful with all of this mass marketed advice, been really disappointed and disillusioned, not because they're not making money, not because they're not getting clients, but because it feels like it's just not quite allowing them to bring the best of them to the table.
Diann Wingert: So what I help them do, and I'm working with people exclusively one on one because I like to get into their biz shiz, like, up to my eyelashes, you know, holistically, the person and the business. Chances are they are doing too many different things for too many different people, and they're not locked in on their most unique offer so that it can really stand out from the rest and be profitable and fulfilling to them. So that's what the purpose of the boss at breakthrough is. And, basically, like so many other people who've created their own framework, it was based on my own frustration and disillusionment with spending tens of thousands of dollars on courses, coaches, and other programs that ultimately let me down. So I'm like, well, fuck this.
Diann Wingert: I'm gonna burn all this down. I'm gonna do everything in the opposite way of what I've been taught, and now I help people create businesses that are unique to their gifts. It's very fulfilling.
Erica: And that's what everybody needs because the world is a big place, and I don't even know how many billions of people are in here. But for all of the people looking to start businesses, you know, one of those limiting beliefs is always like, oh, there's so many people who do this and there's so many that. And it's like, yes, but no one is you. No one takes your unique strengths, your stories, and how it worked for you, and there are however many hundreds of thousands of people that need to hear that message from you. So I
Diann Wingert: You know what I just realized?
Erica: What?
Diann Wingert: And I thank you for this. I just realized that one of the reasons why I prefer working with established business owners who need to change their business to unleash its full and their full potential is because I'm not afraid to change. I am not afraid to start over. I am not afraid to say, I don't care how big the sunk cost is. I don't care how long I've been doing this.
Diann Wingert: It's not working for me now. And so I don't have fear of helping other people do that and can make it easier for them to do that because I know the mindset hacks I had to use on myself to pick up the pace and not have these changes drag out so long.
Erica: That's powerful. And it makes me think of I read this just this morning, Diann. I'm reading a book all about the ego. It's called the ego is the enemy, and there is a chapter there. And they were talking about the CEO or owner of, TY Beanie Babies.
Erica: You remember Beanie Babies?
Diann Wingert: Oh, yes.
Erica: And how because he was so just like, this is what we're gonna do, and we're never gonna change it. And I could put a TY sticker on a bag of dog shit, and they would buy it. And that company is like, no more.
Diann Wingert: Blah blah. Well, you remember Blockbuster Video. Like, every suburb had at least one of them. And I remember because I've read this story that when Netflix came started it, it was just like a twinkle in somebody's eye. And the CEO of Blockbuster said, that's never gonna work.
Diann Wingert: People love coming to their corner Blockbuster, going through the aisles, and finding out their favorite movies are not available because somebody didn't return them? Hell no.
Erica: Like, I have Can you imagine the level of Oh. That one.
Diann Wingert: Oh, dude. I would change my name and go into the witness protection program. Like, I wouldn't I wouldn't want anybody to know I was that but, you know, it's such a good point. Like, why are we so afraid of change? Why do we cling to our sticky floors when they cause us so much suffering?
Diann Wingert: I think it's because allowing ourselves to evolve, whether it's leaving your career and starting a business, pivoting or rebranding in your business, burning your business down and starting a new one, or even deciding business is not for me and going back and getting a job because we are afraid of making mistakes. We are afraid of being disappointed. We are afraid of looking bad to others, and we need to deal with the identity ego aspect of it. You have to become a different person to live a different life, and I think that's really overlooked.
Erica: Yes. And that's why all of those things, like the fear of what other people will think, the fear of failure, those are all massive sticky floors. Uncomfortable but familiar. Exactly. And the one question that I love to ask all of my guests is if you could go back in time and talk to Diann from so many years ago, maybe before you started this consistent personal evolution, what is the one piece of advice you would give her?
Diann Wingert: Trust yourself. I have really good intuition. I think it's one of the reasons why I came through my childhood as resilient and resourceful as I did. And I have allowed many people to talk me out of what I believed because I thought, oh, they're more experienced. They're more knowledgeable.
Diann Wingert: They're more educated. And if I've learned one thing over the last couple of years, last couple of decades, honestly, guts don't lie. Your intuition is a resource and maybe the most precious and powerful and trustworthy resource you have. So I wish I had understood that much sooner.
Erica: I love that. And, Diann, if somebody has heard this and they are like, damn, I need to work with her. I need to, like, have her get into my business. Where can they find you?
Diann Wingert: Well, as much as I love people who fall madly in love with me and want to hire me on the spot, and that does happen, I would actually like to encourage them to go to my website, DiannWingertCoaching.com. And Diann has a funky spelling, so you're gonna have to trust Erica to spell it correctly in the show notes. But, you will find at DiannWingertCoaching.com, there's a terrific quiz there. My podcast is there. My blog is there, and you can find all about how to work with me.
Diann Wingert: And if you don't wanna go to my website, then you should go to my public podcast, which is called the Driven Woman Entrepreneur. If you don't mind my swearing and you don't mind my highly opinionated nature, there's a lot of juicy goodness right there.
Erica: Well, guess what? They're here, so they probably will welcome that. And you do have an amazing page, which is titled shiny objects. And so, of course, I was like, oh, what's that?
Diann Wingert: Gotcha.
Erica: I'm gonna link that page. But, Diann, thank you so much for being here today. This was so fun.
Diann Wingert: I love spending time with
Erica: you. Same. Wasn't that an awesome conversation? I tell you, Diann, Garin fucking teed it right at the beginning, and it was so inspiring. I hope that it helps you on your continuous journey of personal evolution.
Erica: But until next time, friends, please rate, review, and subscribe to the podcast as it truly helps it land in the hands of the person that needs to hear it the most.
RESOURCES MENTIONED IN THIS EPISODE:
- Ready to stop shrinking yourself to fit a life you've outgrown? Join HER Collective, Erica's community for women in corporate America.
- Diann Wingert's coaching site and Boss Up Breakthrough framework: DiannWingertCoaching.com.
- The Driven Woman Entrepreneur, Diann's own podcast: The Driven Woman Entrepreneur.
- Connect with Diann Wingert on LinkedIn.
- The Ego Is the Enemy by Ryan Holiday, the book Erica mentioned about the Beanie Babies and Blockbuster CEOs: The Ego Is the Enemy.
RELATED EPISODES:
FREQUENTLY ASKED QUESTIONS:
What does Diann Wingert mean by “pick and stick”?
Pick and stick is Diann's term for the cultural pressure to choose your career, partner, and lifestyle once and stay there until death or retirement, treating any change as a personal failure. Diann rejects this outright, having changed careers three times, married three times, and changed her religion, all as part of what she calls continuous personal evolution.
How common is it to want a career change in your 40s or 50s?
Very common. Research from Careershifters found that about a third of professionals aged 45 to 54 expect to make a significant career change before they retire, with unhealthy work environments, poor work-life balance, and values misalignment as the leading reasons, ahead of pay.
What is the Boss Up Breakthrough framework?
It's Diann Wingert's coaching framework for established business owners who are making money but feel disconnected from their work. Instead of generic six-figure formulas, it helps business owners narrow in on the one unique offer built from their own specific gifts, story, and values, rather than copying a cookie-cutter strategy.
MORE FROM ME
Follow me on Instagram @ericaandersonrooney and @joinhercollective
SUBSCRIBE & REVIEW
If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts. Your support helps us reach more women who need these insights. Thank you for tuning in to the Glass Ceilings and Sticky Floor podcast. See you next week!
Hi, I'm Erica!
In the last 15 years, I climbed to Chief People Officer, 6x'd my income, walked away from a culture that stopped matching my values, wrote two books, and built HER Collective to help thousands of women rise to power and lead in the age of AI. I've learned a thing or two about smashing ceilings and closing gaps, and Glass Ceilings & Sticky Floors is where I open the playbook, the receipts, and the real stories to share it all with you.
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