Unmasking Authenticity: Empowering women to trust themselves and embrace their true desires
In this episode, Mic chats with the fabulous Diann Wingert. Diann shares her personal journey of taking off the mask and being true to herself. She discusses her childhood trauma and the masks she wore to survive. Diann emphasizes encouraging women to trust themselves and embrace their desires and priorities. She also explores the balance between strength and femininity and challenges societal expectations. Diann discusses her transition from therapy to coaching and the barriers that hold women back from starting their own businesses. She emphasizes the importance of embracing failure, taking risks, and stepping outside one's comfort zone.
Work with Diann:
https://www.diannwingertcoaching.com/shiny-objects
Free Quiz:
https://quiz.tryinteract.com/#/5e86e90dce39a3001432b6db
Listen:
The Driven Woman Entrepreneur Podcast
https://www.diannwingertcoaching.com/podcast
Connect:
https://www.linkedin.com/in/diannwingertcoaching/
Listen to the full episode:
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Mic (00:01.817)
Hey everyone, welcome to the Kindling Project Podcast. This is Mick and today I am joined by Diane Wingert. I'm so excited. Diane, you are a former therapist, turned business strategist and coach who helps female consultants and coaches create profitable, sought after, right size business based on their unique expertise using your signature framework, the Boss Up System. Welcome. Hello.
Diann Wingert (00:30.638)
I've really been looking forward to this call and I know it's gonna be juicy.
Mic (00:34.937)
So good. So Diane, okay, this is our first interaction. So our listeners know. And here's the thing, girl, I pride myself in being a straight shooter. I'm 50 now. I don't have time for bullshit. Girl, you don't have time for bullshit. And so I really perused your website. I read your blogs. I listened to your podcasts. And Diane, can I tell you, I'm going to be serious with you. Hats off to you. Fantastic body of work. What?
Diann Wingert (01:02.158)
Thank you.
Mic (01:03.039)
No, really what resonates with me so deeply is that you're such a straight shooter, too And sure you have fancy degrees and we can get into that but mostly yeah, you're this woman you're living in your truth
Diann Wingert (01:09.038)
Mm -hmm.
Who cares?
Mic (01:17.945)
And I read this in your website and I'm like, Oh my gosh, this is my woman. This is my girl. This is not my first rodeo and I've made all the mistakes. So you don't have to. My goal is to shave years off your learning curve. So you get farther, faster, and with lots less frustration, fatigue, and fuck this, which is like, Oh my gosh, she's talking my love language. I know. So let's get started. Okay. One of the things that you said,
Diann Wingert (01:39.118)
Yep. Those are my words. Yeah.
Mic (01:46.969)
Building something authentic requires taking off the mask and having the courage to be true to oneself. Can you share what mask did you have to take off?
Diann Wingert (01:57.774)
Oh God, I think I had multiple layers and this goes way earlier than the COVID pandemic where everybody else was wearing one too. You know, I learned very early in life. I was adopted and I was adopted into an upper middle -class family with a largely absent father and a very abusive and really mentally unstable mother.
So luckily for me, I was a gifted kid. I was very bright and I was very observant. And I figured out pretty early on that this was not a safe person. So I started developing resiliency from a very early age and stage because I needed to keep myself safe. And I think that the mask wearing started with recognizing, watching her behavior, watching how she would go off on some of the kids. They were a
bunch of adopted kids in our family. She was like Mia Fair. It's so cringy. I don't even know if I want to say it, but at the height of her insanity, there were two biologicals and eight adopted. And I'm not talking foster kids. I'm talking legal, legitimate adoptions. So the family got bigger and bigger and bigger, and she got crazier and crazier, and then it started shrinking. And it was literally the best way I can describe it without completely horrifying you.
Mic (02:49.177)
How many?
Mic (02:53.945)
Okay.
Diann Wingert (03:17.262)
is it was like a cross between musical chairs and Hunger Games. Like one kid after the next just started disappearing. Like literally, I kid you not, I would come home from school. There would be one less bed, one less place setting. A kid would just be gone. And I'm not talking babies. I'm talking like full on like six, seven, eight year old kids. Disappeared, who knows? Unadopted.
Mic (03:21.625)
Oh boy.
Mic (03:41.081)
Where do they go? Oh, to this day, you don't know?
Diann Wingert (03:45.71)
Oh, no, no, by the time everything was said and done, there were two biological kids and two adopted kids left. I have no idea what happened to the others. I honestly and people always ask me because I don't blame them for being curious because it's such a crazy situation. Did you ever go look for them? You're probably wondering, too. So I'll just cut to the chase, because as you say, I'm a straight shooter. I did not. And I'll tell you why.
It took everything in me during childhood to survive this household and to prepare myself for my future on my own. I became extremely self -sufficient and the masks I learned to wear to get through the childhood and get out of that house and never look back was to be compliant, to be.
the consummate good girl to get good grades, to never talk back to if I did anything naughty or wrong, I concealed that shit like a professional criminal. And so I also had, sure.
Mic (04:55.129)
Is I'm sorry, Diane, is that the only reason you think you made the cut? Is that the only reason you were still standing at the end of all this hunger games, if you will?
Diann Wingert (05:03.854)
I, that's a good astute question. I thank you for asking it. I believe that even though she was crazy, I figured out what set her off, the behaviors that the other kids would engage in that would set her off and she would go after them. And I would try to tell them, don't do that. Can't you see that's why you're getting beat? And I was able to steer clear of those things and mask.
my other struggles because one of the reasons why she would get rid of some kids is if they had learning disabilities or behavioral problems, that was a hell no for her. So I had a specific learning disability. I also had ADHD and I was in the gifted program. So I was very neurodivergent, but nobody knew what that was back then. So I would do what I had to do. Like I would cheat off other kids' papers.
but I had the persona of the good girl, the teacher's pet, the, you know. So I did what I had to do to get through and to get out. And I didn't really know that I had these brain -based differences until considerably later in life. I have a lot of shame. I wouldn't say guilt, but I have a certain amount of shame about setting the course to survive and not trying to take the other kids with me because I just didn't think I had.
Mic (06:03.129)
Mm -hmm.
Diann Wingert (06:25.902)
I had the bandwidth. I didn't think I had the capacity to do anything but get through and get out. And that's what I did. So there was a lot of masking going on, including not appearing to be bothered by one sibling after the next disappearing. I didn't question her. I didn't shout. Of course I thought it was crazy. I wondered why the authorities weren't at our door like every other day. But I...
Mic (06:48.793)
Sure.
Diann Wingert (06:54.976)
I was the quiet survivor. I just didn't give her a reason to be mad or upset. I didn't give her a reason to find fault with me. And so I made the cut, so to speak. And yeah, I'm not proud of it in that sense, but I am very proud that I was able to figure out what I needed to do to keep myself safe and keep on going.
Mic (06:57.145)
Hmm.
Mic (07:18.521)
Okay, well, this feels like this could be an hour conversation, but honestly, you're a child, you are just trying an adopted child too. And you're seeing what's happening to your peers. You're surviving. So you have to give yourself a lot of grace to say, I did what I could with information I had in front of me at the very young age, not to be able to have the mental capacity to see the bigger picture.
Diann Wingert (07:29.838)
Yes, yes.
Diann Wingert (07:41.294)
Yeah.
Diann Wingert (07:45.198)
Yeah, that's fair. I appreciate that.
Mic (07:45.465)
So that is fair. Of course, of course, because I come also from a lot of childhood trauma. And so I understand now as an adult, I can reflect back and say, oh, I wish I could have, would have do it. As a young person, you can't do that. You don't have the capacity to make those decisions. But so now that you understand all these things and you've done the work,
Diann Wingert (07:59.436)
Hmm. You're a kid.
Mic (08:07.225)
and where you are today, when someone, if I ask you, what do you stand for and what do you believe in? What really surfaces for you?
Diann Wingert (08:18.574)
I think what I stand for most now is encouraging other women to trust themselves. I think one of the reasons why we develop these masks is because we are socially, culturally, oftentimes in our religious institutions, all of our public institutions, from public school to corporations, we are conditioned to be good girls, to do what we're told.
to not ask for more, to not challenge authority, to strive to not make mistakes, not be a problem to other people, not be a burden to other people. And we're rewarded for those things. I mean, people will say, oh, she's so nice. Or she's so sweet. I used to think those are compliments too. Now I realize that they are reflective of how well you are performing a very narrow role.
that has been assigned to you, which probably has little to nothing to do with who you actually are. I think some people are born to stand out, but we are all culturally conditioned to fit in and blend in because we punish those that are different. You're different in any way. You're going to be ostracized. You're going to be punished. You are going to be bullied. If you're gay, if you're biracial,
If you have any physical differences, behavioral differences, like kids learn very early in age, even if you don't grow up in a crazy family like mine, kids learn from a very early age that there are accepted ways to look, to be, to feel, to show up, and there are unaccepted ways. And even though we like to claim that we are progressive and we are accepting and we embrace diversity, we do not. That's bullshit.
Mic (10:11.801)
Mm -hmm.
Diann Wingert (10:13.376)
Institutions exist to get people to conform to the norm because it makes them easier to manage. And you're just focusing on everybody being kind of in the middle. They're always gonna be outliers and you're not gonna meet the needs of those people. So you have to get them to behave like everyone else. So I think human beings, and part of this is also biological. Like if you think back to our very, very, very ancient ancestors, like we're talking cave days.
Safety comes in the form of being part of the tribe, being part of the group, being part of the collective. If you're an outlier, you're going to get picked off by another tribe or a wild animal. So it's in our genes, it's in our DNA to be part of a group. But I think women don't often know who they are, what they want, what they need, what they prefer, what matters to them, what they stand for.
until 50 or even beyond. And it comes as quite a rude awakening when all of a sudden your kids are grown and flown, your marriage is either blown up or barely functioning, your career is looking at you like, isn't it time to ease on down the road? And you don't even know who the hell you are. That's not an uncommon experience. I think it's what most women go through. And now you've got all the disruption.
of menopause at the same time, it's a genuine crisis for a lot of women, I think. So I stand for normalizing all of that and encouraging people, women in particular, like get to know who you really are, your needs, wishes, wants, preferences and priorities, even if you don't assert them, because the time will come where your life will depend on it.
Mic (12:07.001)
So true. I receive everything you just said. And for me is that to mirror back what you're saying, no child escapes their childhood without these false narratives, these labels that we've attached to. And we attached them and we own them as our truth. And it's a false narrative. So I agree with you from that perspective as well. But.
Diann Wingert (12:21.614)
Yes, yes.
Mic (12:34.297)
I'm going to just play devil's advocate here. Do you feel though, and because you do work with a lot of entrepreneur women, is there a flip side from being good girl, which many of us are trained to do very well, to feeling like, well, they and I have to go compete in the real world. So I'm going to turn on the power side. And then the power side of us sometimes comes off like we're bitchy and strong and not really authentic ourselves, but we feel like we have to show up that way in the world. And I often think, boy, can we,
Diann Wingert (12:44.46)
Mm -hmm.
Mic (13:04.203)
Can we be strong and feminine? Can we be powerful and use our voice, but also be vulnerable and have the softness that it is us as a feminine being? And is there shame in that? What are your thoughts on that?
Diann Wingert (13:19.118)
Hmm. These are such good questions. You know, I think sometimes there is a backlash, Mick. I think sometimes, you know, the degree to which a woman has felt sort of oppressed or repressed or suppressed, or maybe she's just done it to herself. And now she's like coming out in a big way. I'm making up for lost time. I think when this is like very dramatic, whether it's because she's now like the kids are...
situated, maybe they're off to college and now she's been a stay at home mom, she's going out into the workforce and she's gonna go kick ass and take names, or maybe she's been quietly languishing in a lousy marriage and now she's liberated herself and now she's gonna declare, I am woman, hear me, whatever the tipping point is, if it's really dramatic, if she goes from submissive and demure to,
Mic (14:07.033)
Mm -hmm.
Diann Wingert (14:17.998)
you know, aggressive and demanding. That's more than just a course correction. That's a reaction to something. And I don't think that's healthy either. Because sometimes when we have a lot of buildup, like we're feeling like resentful, maybe we've been the good girl is the perfectionist, people pleaser, you know, just suppresses her own needs and just does what's expected of her and what's wanted of her. But maybe,
Mic (14:20.601)
Mm -hmm.
Diann Wingert (14:46.91)
underneath that she's seething, she is filled with rage. Once she gets to the instability, the chemical instability of perimenopause and menopause, sometimes all that stuff comes flying out like, holy cow, like she's a witch on a broomstick, you know? And sometimes that's a temporary, like, biological correction. But I don't think it's, I don't, I wouldn't say it's healthy behavior for a woman to be a
Mic (14:49.977)
Mm.
Mic (15:03.211)
Yep.
Diann Wingert (15:15.886)
aggressive to the point that even people who like her are calling her a bitch. It might be a misunderstanding about what she thinks power takes, what it requires.
Mic (15:21.367)
Mm -hmm.
Mic (15:27.129)
Yeah, sometimes I think it's just another mask that they feel like they have to put on again, not being authentic to themselves. Like you actually can be really powerful and strong and use your voice and still be feminine and soft. If you choose to be, I'm not saying all women are this way. I'm just, I've noticed this either black and white and Diane, maybe you feel this way too. I'm tired of women for us having a choice. We have to be this or that career or stay at home.
Diann Wingert (15:50.518)
Mmm.
Mic (15:52.631)
soft or strong. It's like these choices that we've been given normalized in society have
have put us on these boxes and the we're just not desperately like, no, get me out of this box because I'm a lot of things and I'm messy and I'm still strong and I'm brave and I curse and I, you know, I'm all of, all of me, all of you is a beautiful complex package with so many colors. And that what's, that's what makes you so beautiful and magical. And so I feel this way by women. Yeah.
Diann Wingert (16:23.694)
This is such a great conversation. This is such a great conversation. I agree with you a thousand percent. As a matter of fact, I like to think all of the facets that we have are like colors in a stained glass window. You need all the colors to create the beauty of that window because they compliment each other. And I have two thoughts about this. One, in a way it's not our fault. I've studied neuroscience for 30 years.
Mic (16:45.337)
Yes.
Diann Wingert (16:52.334)
And how the brain actually works is at its most simple, like a simple computer. The brain works to observe, label, categorize, and store information to be retrieved later. We are accustomed from our earliest cave days, you observe an animal that you don't recognize on the savanna. You have to make a very quick determination. I'm observing this thing.
What is that thing? Have I seen that thing before? Do I know what kind of animal that is? I don't have a label for that animal, but I do have a category of animals that look like that. Maybe it's a cheetah and you've only seen a panther before, but what you know about panthers is that you want to run like hell in the other direction and climb up the highest tree you can find. So it's normal for human beings to want to put everything into categories.
including other human beings. But I think we need to fight that because every person is an amalgamation of a variety of things. I think it's a shortcut that hurts us all. And it is one of the very first things that leads people to be biased and to have stereotypes and to become racist or transphobic or whatever. Because if somebody fits in this box,
with this label and you've decided which labels are good and which labels are bad, you stop paying attention to anything else about that person. They're either all good or all bad. It actually takes more work in our brains to defy those boxes. And I do think, because I know how old you are, I do think that when we cross over into our 50s, this is the time where we begin to reject.
Mic (18:45.497)
Mm -hmm.
Diann Wingert (18:49.134)
so many of the conventions and the conditioning and the conformity that we've to some degree more or less willingly gone along with until that point. Because once we stop producing estrogen, we don't give quite so many fucks about what other people have to say biologically. It's the most fascinating thing. I want to tell you about a book. If you haven't read this,
Mic (19:14.649)
I love this. Okay.
Diann Wingert (19:17.646)
You're gonna probably order it as soon as this call is over. The book is called The Female Brain. It's by a female neuroscientist, female, I think she's a neuro, I forget what kind of physician she is, but anyway, she's a physician, Lou Anne Brizendine, The Female Brain. In chapter seven, The Mature Female Brain, I literally, I think my heart stopped and my brain wheels stopped turning for a second when I read basically, I'll paraphrase,
Mic (19:30.489)
Okay.
Diann Wingert (19:44.266)
menopause, which I like to call the estrogen evacuation. When estrogen has left the building, and this is even true if you supplement, because as many women do, I'm on hormone replacement, I have been for years. When you're no longer producing your own estrogen, estrogen is called the tend and befriend hormone for a reason. From the time we go and start having periods all up into menopause, we are under the influence of a powerful psychoactive substance that our own
Mic (19:47.609)
Mm -hmm.
Diann Wingert (20:14.03)
body makes called estrogen, which literally programs us to want to take care of others. It's why we're still here and not extinct. So when you go through menopause, it's literally and it can happen suddenly or gradually, you literally go from what the fuck is with all these? They're so ungrateful. They're so demanding. I literally want to run away. I don't want to care about anybody anymore. Fuck you all. And it's like,
And then they think, oh my God, am I getting Alzheimer's or what's the matter with me? And you go to your psych, then what does your doctor do? They put you on antidepressants. I'm not depressed, I'm waking up.
Mic (20:45.337)
Great.
Mic (20:51.833)
My gosh, I love I've written this down. I cannot wait to get this book because you have just described me to a T. I am now on this campaign. Yeah, like it's time we get selfish ladies is what I tell my friends are like self. I'm like, yeah, selfish. And this is how I I I I and they're like, Oh my god, that doesn't sound like you, Monica. But no, it's not because if I show up as me, I'm going to be so much better for all of you my entire ecosystem.
Diann Wingert (20:58.414)
Of course, it's normal.
Diann Wingert (21:04.526)
Hmm?
Diann Wingert (21:17.324)
Yeah, and you're showing up without resentment. See, I think, you know, we all know about time management. I think what we have to start practicing at 50 and up is energy management and obligation management. Because let's be honest, up until 50, most of our time, energy, effort, focus, attention and dollars is being directed towards what?
other people want, expect, and need from us. And once the estrogen evacuation has taken place, we are now thinking, well, hold on, what about me? And if you don't know the answer to the what about me, because honest to God, nobody's ever asked you what you want, because they're too busy trying to get you to do what they want. And now it's like, geez, what do I want? It can be really crushing.
Mic (22:06.263)
Mm -hmm.
Diann Wingert (22:14.19)
think, God, I'm this far into my life and I don't know what I want. Maybe I don't even know who I am. It's not your fault, my friend. You have not been given permission and you have not had role modeling or mentorship for more mature women that this is a natural part of life. And you are about to cross into what very well could be the most interesting, the most satisfying and the most fruitful stage of your life.
But if you don't know what's happening, it probably won't be. And if you look to the culture around you, it for sure won't be because the message from our culture at large is if you're over 50, let's be honest, over 40 in many places, it is time for you to shrink and fade. It is time for you to shut the fuck up and go be quiet somewhere. And if you want to play pickleball, that's acceptable. And if you want a day drink and watch the reality TV, that's all good and fine. But.
Don't even think for one second about being more visible and taking up more space because we're not interested. And that's why we have to do it. We have to give ourselves permission because otherwise we're missing the opportunity.
Mic (23:23.801)
So true. Oh my God, so good. Everything you're saying. So now you've built the business around this to help women release some of these labels and tell me a little bit about your approach, your signature sauce. And also please tell the audience how you pivoted careers to where you are now.
Diann Wingert (23:41.9)
Hmm. Well, I'll tell you what, I have recently come to claim this label. I am on the path of continuous personal evolution. And the reason why I felt like I needed to take charge of that narrative is because part of the conformity that we are conditioned to in our culture is what I call pick and stick.
We're like, we're barely old enough to know our ass from our elbow. We're 18 years old. We've been under the influence of our parents all these years. Now we go to college and everyone's like, what are you gonna be? How the fuck are they supposed to know? They don't even know how to be independent yet. So you got to choose your major. And I think there's a lot of emphasis, and this has been true for many, many years. You are within a very short period of early adulthood, supposed to figure out what your academic path is, what your occupational path is.
what lifestyle you aspire to, then you gotta find a mate, and this is for heterosexuals largely, find a mate, settle down, buy a house, have a family, get a promotion, and we're like on the thing, and then you start comparing yourself to everybody else, and how, you don't start, we've been doing it all along, let's be honest. You're like, how am I doing compared to everyone else, and reflecting something called the social clock. Gosh, I thought I'd be further.
at 30, 40, 50. Why did you? Oh, because you're looking at what everyone else is doing and assuming that you're supposed to be doing the same thing without ever asking, is that what I want? What if I don't want to get married? Because it turns out, I mean, I was adopted. You might think it's a crazy or a bold choice to decide to have children of my own, but I did. I have three kids. None of my kids wants kids. And so I think I've done a good job of raising them to think for themselves.
instead of just following along and doing what everyone's doing. But I think I've had three marriages, I've had three careers, I've even changed my religion. It's not because I'm unstable, it's not because I lack the ability to commit, it's because I know who I am and I give myself permission to outgrow things. Like I seek mastery in what I do. So if I go into a profession,
Mic (25:57.145)
Mm.
Diann Wingert (26:02.51)
My first career was in medical sales. My second career was in psychotherapy and social services. And I crawled all the way up the food chain. I was a clinical director of a big agency with multiple programs. Then I decided to go into private practice. After about five, five or seven years, I don't remember exactly, in private practice, I realized, you know what? I've loved this career. I've excelled in this career. I've helped so many people through this career, but I don't want to do it anymore.
because psychotherapy is focused on insight and healing. And at 50, I wanted to be helping people grow and change and reach their goals. I didn't want to continue to have conversations about healing. Now, I do not think coaching and therapy are equal. A lot of people seem to be confused about this. Therapy is absolutely the modality you need.
Mic (26:50.137)
Mm.
Diann Wingert (27:00.302)
If you're dealing with trauma, you're dealing with abuse, you're dealing with addictions, you're dealing with serious mental health disorders, and you need healing, you need coping strategies, you need strengths, you need insight about how to make changes in your life so that you don't continue to suffer. But once things are good, then what? Maybe at that point, therapy's not the ideal modality. Maybe if you're like, life is good, actually life is very good, but...
Mic (27:26.617)
Thanks for watching.
Diann Wingert (27:28.558)
I feel like there should be more. I feel like I want to set new goals. I want to reach new heights. I want to change things up. I think coaching is better suited to that. So I gave myself permission to close my business, get the coach training, start working online and going from there. Because I realized there's a lot of women. I was working at the end of my private practice career with mostly women in this age group, 40 to 60.
who wanted to make changes in their life, but didn't quite know themselves well enough to trust that they would make the right decisions. It was a very natural transition into coaching. And then I just decided the ones I really enjoyed working with the most are ones who had the audacity to want to start their own business at 50 and beyond, because that was exactly what I did. And I think it's really exciting. It's an unconventional choice.
But I think it can be an extremely satisfying one that many of us are well suited to. We just need a little bit of help to get there.
Mic (28:32.409)
Oh, so true. So you have so many women in your ecosystem and you've worked with hundreds if not thousands. So can we talk a little bit about what you think keeps women stuck or some of the barriers holding them back?
Diann Wingert (28:44.238)
Yes, I've talked about some of them already in that. I think our cultural conditioning to be good girls and to avoid making mistakes, that puts us at a serious disadvantage when we want to start our own business. If we don't want to make mistakes, if we're perfectionist, if we want everything to look really good, oh, and also people pleasing, I would say perfectionism and people pleasing are two of the big things that hold us back because
Mic (28:46.809)
Mm -hmm.
Diann Wingert (29:13.87)
Truth be told, when you decide to start a business, even some of your best friends and family members are gonna throw shade. They might even tell you they think you're crazy. What do you wanna do that for? If you don't have any friends that are entrepreneurial, they may say, oh, we believe in you, we just don't wanna see you hurt or disappointed. Why don't you let me be the judge of where that should be a problem? So I think...
Mic (29:22.777)
Mm.
Mic (29:26.873)
So true.
Diann Wingert (29:40.91)
There's not a lot of role models. There's not a lot of other women doing this. So we have a lot of fear. If we have been perfectionists, which my password for one of my accounts is recovering perfectionist, because you just have to keep working on this and keep peeling away at the layers of this from this good girl conditioning. But when you're a perfectionist, you have low risk tolerance. When you have low risk tolerance, you don't want to make mistakes. When you don't want to make mistakes,
you do everything humanly possible to avoid failure, you are never going to be as successful as you could be in your own business if you don't learn how to dance with failure, because you're just gonna keep doing the things that you are already certain will work when there might be something so much better for you, but you're not willing to try it because it might not work out. So I think women are at a disadvantage because we don't have usually.
We don't have as much experience with normalizing failure. And I'll give you a perfect example. One of the most popular episodes on my podcast and one that I certainly got the most DMs from is an episode called Lessons from a Failed Launch. Because nobody's talking about failure. Nobody's normalizing it and nobody's is showing it off. Hey, you want to talk about my fuck up?
Mic (31:08.045)
Yeah.
Diann Wingert (31:08.11)
And so I think it's really important because if other women realize, oh, wow, you have a profile, people know who you are, and you're willing to talk about your failure publicly, like, hmm. And it's not because I'm a badass, I'm an I .M., but I just think that if we get accustomed to the idea that you have to be willing to take risks and make mistakes and get it wrong without making that
mean you don't know what you're doing, you're not qualified, you don't have what it takes to be self -employed, or that you're a failure. Like these are mindset issues and we need to address that.
Mic (31:48.793)
It is so, so important. And this message, I really want our listeners to pay attention to this because first of all, failure is the word alone makes it sound so negative, but it's actually an immense, massive opportunity for growth. I mean, I've learned more from my failures and from people telling me no, than I've learned from any success I've ever had.
Diann Wingert (32:10.954)
Yes.
Mic (32:11.993)
And two, I would say, Diane, you know, so many people to your point are so afraid to start things because of perfectionism. The idea that we lean into what our strengths are, which is nothing wrong with that. Obviously there's some power in that. But growth doesn't come from our strengths. Growth comes from capitalizing or at least honing in and spending time on the things we aren't good at. That's how we get better. It's not that...
Diann Wingert (32:19.086)
Hmm.
Mic (32:39.545)
It's not rocket science here, people, but we lean too much. I see society well, oh, I can't do that. That's not me. I don't know how to do that. I don't know how to start a right. I don't know how to start a business. I don't know anything about finance. I don't know. I don't know. I don't know. In the meantime, I'm like, you don't have to know, but you can learn and you can learn enough to get you to the next step. And to me it's like focus there because your strengths, I will clap out your strengths all day long.
Tell me, tell me the story where you weren't strong at something and you did it anyway. And girl, I'm going to be like, yes, yes. Celebrating you. Those are the moments.
Diann Wingert (33:19.246)
It's easy to do something. I mean, first of all, if something is a strength, it's because you have experience doing it, because you've practiced doing it. But think back to the very first time. I mean, every single thing we've mastered in our life, every single one.
We did it for the first time, once upon a time. And the first time at anything, whether it's driving a car, asking for the job or the promotion, having an uncomfortable conversation with a parent or a spouse, like firing someone at your job, like every single thing that's hard, we have done once upon a time for the first time. And...
Every time we do something new, it's outside our comfort zone. And we have what I call FUD, fear, uncertainty, and doubt, 100 % of the time. Because the truth is, no matter how much you might have gotten some consultation or advice, you still don't know exactly what's going to happen. You couldn't. It hasn't happened. So if you've done anything in your life for the first time, and you did it again, you already have this skill.
Mic (34:39.097)
I I love this. I know it's sort of when you were saying listing those things I remember thinking that anxiety I felt when they handed me my baby for the first time and said okay you can leave the hospital and I thought What do I do with this I don't have a rule book and What and now you know now I have a 21 year old 19 year old and I still screw up But I am getting better at this parenting thing So you're right. You've got to start
Diann Wingert (34:51.662)
It's yours now. You're like, oh shit.
Yeah, no clue.
Diann Wingert (35:06.03)
If we, yeah, if you have to start, and you know what, the thing is, is that some of my biggest areas of growth are not mastering things I suck at, but recognizing the time it would take for me to become minimally competent in certain areas, looking at my capacity, looking at my bandwidth, looking at the commitments that I already have, and then coming to the determination that,
the time and energy and effort and opportunity cost it would take for me to learn how to master this new skill, whether it's like building a website, editing a podcast, whatever it is, is it a better use of my time to learn that or to hire someone to help me with that so that I can spend more time in my zone of genius? For me, especially with my history,
I was the most stubbornly self -sufficient person on the planet. Like, I mean, really to the point it was ridiculous. I would pack my grocery bags so full so I could make fewer trips to the car. And when the bag boy in the supermarket would say, can I give you some help with that? I remember firing back one time. Do I look like I need your help? Like, it's what you were saying earlier about like the aggressive. He looked at me like, scary. And I thought, you know what?
Mic (36:25.433)
Yeah, right.
Diann Wingert (36:30.03)
You do not have to do everything yourself. And it's probably not smart to try. Sometimes the growth for me anyway, if you're kind of person I am, sometimes the growth comes from recognizing that I don't know how to do something and that I need help and having the humility to ask for that help or hire it.
That's been where a lot of my growth is because I've always had this thought, well, how hard can it be? And then I found out, oh, she's much harder than I thought and very time consuming.
Mic (37:01.689)
It can be hard.
Yeah, I actually wrote a quote here. I don't remember if it was you or one of your guests that said, being a Jill of all trades is not a flex, even if your ego freaking loves it. Did you say that? Yeah, I love it. I thought, yes, that's so exactly true because sometimes our ego will not sometimes all the time our ego gets in the way of everything we want to just get done and accomplished. So Liz, another thing that you talk about in some of your coaching is option versus opportunity. Can we talk a little bit about that? Because I
Diann Wingert (37:13.678)
That's me.
That's me. Yeah, yeah, that's me.
Diann Wingert (37:34.326)
Mm hmm. Yeah. I'm so glad you prepared the way you did. It makes for much better conversation, much more nuanced. I really appreciate that. I have principles in the way I coach that I try to make them memorable, but there are really ways to encourage people to think strategically and learn how to trust their own intuition. Because I think if we've spent most of our life looking to others,
Mic (37:36.011)
I thought, I think this is brilliant. Yeah.
Diann Wingert (38:02.318)
the authority figures, the experts, sometimes husbands, to tell us what to do and give us permission to do it like life is one big game of Mother May I. We're woefully unprepared, not only for menopause, but for starting a business. So taking responsibility for those things. And I think just recognizing that you know more than you think.
It's okay to fail and not everything that presents itself to you as an opportunity you can't afford to miss actually is. Like I have ADHD. A lot of the people I work with have ADHD and between you and I and everyone listening, most people who are entrepreneurial have ADD -ish traits, right? And so an option versus an opportunity is, you know, when people are really good at marketing,
marketing their coaching program, marketing their mastermind, marketing their whatever, their course. It may look like an opportunity. It may look like I need this, because of course most of us have FOMO. And if we're starting our business thinking, I don't know anything. I don't know anything from anything. I don't know anything about anything. Who am I to start a business? We become a little gullible and a little dependent.
and sort of expect, oh my God, even though maybe you've been, I was successful at several previous careers and still when I started and just going from psychotherapy to coach, I still somehow thought I needed to buy all the courses and go through all the certifications. I'm overqualified. I am overqualified. I have started successful businesses with my current husband and my previous husband. Like I'm overqualified for what I do.
Why did I feel like I needed to sign up for all those things and take all those things? Part of it is because women are conditioned to think we're not enough. We're not pretty enough. We're not sexy enough. We're not thin enough. We're not smart enough. We're not capable enough. And the list goes on. So we carry that into business. And I think what I see happening quite often is that something is actually just an option pretending to be an opportunity. I'm going to give you a couple of examples. Most of us,
Mic (40:21.913)
Please.
Diann Wingert (40:24.526)
And you've probably done this, you're going to start cracking up as soon as I started rattling these off. We started business and we think, what do I know? So we get on everybody's email list because we got to get all the freebies. We got to get all the opt -ins. We got to get all the lead magnates. Then we got to have all the courses, all the coaching programs, all the Facebook groups, all the memberships. And we got to listen, of course, we can listen to all the podcasts and read all the blogs. And it's like, it's no wonder we don't have time to make any fricking money, but it's because...
Mic (40:37.665)
Yep.
Diann Wingert (40:53.838)
One, we don't trust ourself. And two, we don't recognize the difference between an option and an opportunity. On the flip side, once you've got a blog or a membership or a Facebook group or a podcast, people start pitching you. People start pitching you. People say, hey, I want to be your guest and bring value to your audience. What the hell do you know about my audience? And what makes you think I'm not the value? So it's like, this is how I think now, but.
Mic (41:11.257)
Mm.
Mic (41:18.585)
Mm -hmm.
Diann Wingert (41:22.83)
I said yes to so many things because I didn't trust myself, because I didn't think I knew what I was doing, because I didn't have a lot of practice saying, no, let's throw that into the mix. And because I didn't recognize an option versus an opportunity. What changed things is that I realized I'm literally saying yes to everybody but me. I had to pump the brakes. I actually did something pretty drastic, which...
I only recommend if you're at the point where you're like, I'm consuming so much of other people's shit, I don't even have time or energy to produce my own. That is a really good clue that you need to full stop. And then come on, let's be honest, how many courses have you bought that you not only didn't complete, you probably didn't start? How many emails, like how many things did you think you needed? You said yes.
Mic (42:01.017)
Yes.
Mic (42:12.729)
Oh, yes.
Diann Wingert (42:19.982)
And now you feel like, oh my God, I'm so busy. I'm so behind trying to keep up with other people's shit. Unsubscribe. Yes, unsubscribe, unsubscribe. Quiet things down. Create some spaciousness because you can't make discerning decisions about what you need and what you can let go by.
Mic (42:23.833)
And then that just adds to the stress of your day. I hear you. I'm receiving this. Yes.
Yeah.
Diann Wingert (42:48.59)
If you've got so much going on that you're constantly in this anxious, overwhelmed state, once you quiet things down, unsubscribe from a lot of things, they're not going anywhere, you can go back if you miss them, you probably won't even remember what they were, trust me, then you can say, okay, so now that I've made things a little more quiet, I've created some spaciousness, now I need to think about what are my actual goals?
What are my actual goals? What are my values? And what would be an alignment with both of those? So that you're being a little more discerning and not just impulsively recognizing every possible request for your time as an opportunity. Most things you think, oh, I got to say yes to this because I don't want to mess out.
Or, oh, if I have this high profile guest on my podcast, she's gonna promote the episode and my business is gonna blow up. No, it won't. Oftentimes you have to test a lot of these assumptions out and realize you're spending a fuck ton of time chasing maybes that aren't even in alignment with the goals that you have and who you are. But you have to get quiet. You have to get quiet to recognize that.
Mic (44:08.633)
It's so true. So quiet offers us the opportunity to understand the difference between option and opportunity, which is a big difference. And too many of us are hopping on options versus opportunities and wasting a lot of time on options. That's what I'm hearing. And so, yes, so true.
Diann Wingert (44:23.31)
Yes. Yes. Yes. And we also have to be able to say no. That's a huge thing. You got to say no to yourself and to others, mostly to yourself.
Mic (44:36.313)
And I find, and maybe you also have discovered this with your clients, Diane, that a lot of us are just seeking knowledge. And you touch on this too as well. Like knowledge is power. And you share a story about the barista. Can you give me a little bit of that? Yeah.
Diann Wingert (44:50.254)
Oh, I'm so glad you came across that. Yes. I've heard for many, many years, knowledge is power. And I am a knowledge junkie. I love reading. I love learning. I just love. I just love having a full brain. So I was at a Starbucks with a friend of mine and I said to him, well, you know, Kevin, knowledge is power. And the barista.
leaned over the counter and kind of whispered in my ear, because maybe he thought I would be embarrassed. He said, actually, applied knowledge is power. I sort of got, I think my hair like blew back a little bit. I think I might have taken a step back from the counter. I said, thank you so much, because you're absolutely right. And I turned to my friend, I said, Kevin, did you hear what he said? And then I ended up writing about it because,
We love learning and this is something true for many women who want to get on this entrepreneurial path because we don't think we know what we're doing, because we don't trust ourselves and our own intuition, because we think the more is better. We don't know the difference between options and opportunities. We just keep signing up for things and listening to things and going to people's webinars and all this. I just need more. I need more because of course we all believe we're not enough and we never will be. So more is better, right? More is not better, my friends.
More is not better. More is confusing. More is overwhelming. More is exhausting. Because you're going to start at some point getting conflicting advice, and then you're not going to know who to follow. And where this leads to, when you've made the decision to start your own business, and you're not being discerning about the information that you're accumulating, somebody called it being an information whore, and someone else calls it being an information hoarder.
Like it's true, most of the time we don't even go back to read these things that we so desperately thought we needed. But then it plants this idea in our mind that I won't feel ready until I've learned all these things. Well, I got news for you. New things keep being foisted onto the market. New apps, new platforms, new programs, new like AI.
Diann Wingert (47:14.894)
And so the new thing comes out and listen, I have ADHD, I'm up into the shiny object syndrome as much as the next person. But if we don't have the discernment, if we don't know our values and we don't know our goals and we don't know how to say no to options and recognize true opportunities, we clutter up our mind and our life and our business with this belief that well, before I can do this,
Mic (47:20.825)
Yeah.
Diann Wingert (47:41.102)
I have to do this, which means I have to learn this. It's like your list of prerequisites just keeps getting longer and longer and longer and longer. And I honestly have known women who have been trying to start a business for seven years because they are stuck in perpetual learning mode. You would be amazed how little most men know when they start a business in comparison.
Mic (48:07.609)
Yeah, what a difference. So you have to figure it out. So true. So listen, you, I could talk to you for hours, but here at the kindling project, we really are about encouraging women to that it's never too late and that little spark within them. Like we want to help fuel and fan. So give me or give our listeners your three kindling's, you know, your three tips for women reinventing themselves. We've talked a lot about women.
Diann Wingert (48:09.422)
Because you have to figure it out along the way anyway.
Mic (48:37.563)
in their 50s, through going through menopause or after menopause, tell me what are your three kindling?
Diann Wingert (48:44.27)
Three things. One, adopt a mindset of radical self -acceptance and begin to practice it. Radical self -acceptance is very simple and no one can give you permission to adopt this, including me. All it means is I choose to think that I am enough and I can continually work on improving myself. These things are not mutually exclusive. You are enough right now.
and you can continue to improve yourself. You are not lacking anything and you do not need to meet any requirements before you can continue. Second thing related to that is we need to start giving ourselves permission and stop looking to others to give us permission. If you want to do something, do it. Now, if you are married and you need to invest some money in what you're doing, obviously you need to have the conversation with your spouse or partner.
but waiting for someone else to say, yeah, I believe in you. Yeah, I think that's a good idea. Yeah, you should do it. Don't put that burden on yourself. It's completely unnecessary and may not happen. And three, I think women over 50 in particular need to make the courageous decision to become comfortable taking up space. And what I call,
show up, stand up and speak up. At an age and stage when women are told it's time to shrink and fade. I think we have to make a decision. Am I going to get bolder and more true to myself? Or am I just going to age out and live with regret? Obviously, you know which one I chose.
Mic (50:34.649)
I'm right there with you and thank you. Those are really powerful and very meaningful. So as you and I have to have you back by the way, because I know we're running long here because I need to hear about the zone of genius. I want to hear about some of your takeaways from 20. I have so much to unpack with you, but we don't have time for all of it. Yes, please. But I do want to spend a few more minutes on you. What's happening in your world? Tell me what the, what sort of magic are you cooking up and what are you dreaming about these days?
Diann Wingert (50:53.102)
I'll come back anytime. Yeah.
Diann Wingert (50:58.83)
Okay.
Diann Wingert (51:06.894)
I have been working within my current business since 2017. And I mentioned to you a few minutes ago, Mick, that I've come to accept that I'm not a person who picks and sticks. I'm a person who is continuously evolving. And sometimes that means letting something go that I've put a lot into because even though in some ways it's still satisfying,
In some ways, it's still fulfilling. In some ways, it still has meaning and it's helping other people. It has gone to feeling like kind of a too tight pair of shoes. I can still walk. It's just uncomfortable every step of the way. So I reached a point in my business over the last couple of years that I thought I need to make some changes. And I don't know exactly what it's going to look like. I know that.
Mic (51:49.881)
I love this.
Diann Wingert (52:00.014)
2024 is the year I've declared I'm going to rebrand my business and the podcast. I don't know where it's going to end up exactly. I've enlisted help and support from several different consultants that I'm working with consecutively. I'm going to be working with a rebranding expert and graphic designer starting in April. March is SEO. I'm studying the SEO about what are people attracted to in my stuff.
And it's just spending a lot of time with myself and just recognizing what brings me joy and what makes me feel a little tired or resentful, what conversations I'm really not interested in having anymore and which ones light me up. And I think I learned this lesson when I closed my therapy practice.
I got all kinds of different responses from my then clients and I found new therapists for each of them. But I learned then that most people are threatened by others growth when it takes them in a new direction where they're not going to be going. They feel it's selfish. They might feel that you're abandoning them. And I've learned for me when I need to grow,
I can't look to anyone else to give me permission to do that. And people will be disappointed. And I accept that that's part of the choice to honor who I am and my particular journey. So, you know, ask me again in a few months, but I know that there are big changes ahead. I've been laying the groundwork for that by spending a lot of time alone, going for long walks, journaling, and also having meaningful conversations with other people who...
have been part of my journey and are recognizing changes in me and I'm interested in their feedback, not their permission, their observations. So this is gonna be a year of a lot of change. And I'll tell you, I think this is probably one of the things that I think has been most meaningful for me. In the past, when I would make big changes in my life, I felt so much confusion, guilt and shame.
Mic (54:03.641)
I love this.
Diann Wingert (54:21.486)
because everyone around me just does one thing indefinitely and I'm not that person. And I realized I not only didn't have permission, I didn't have a lot of role models either. But since I've embraced it fully, since I've decided I am practicing radical self -acceptance with being this kind of person who needs to live this kind of way and to honor myself, I need to let myself continue to grow and evolve even when others don't understand or approve.
I'm in a place where I feel really good about that now, but it took some effort to get here for sure.
Mic (54:54.425)
I mean, I started the podcast saying one of the things that I admire about you is that you're a straight talker and you don't only talk the talk, you walk the walk and circling back to your personal journey now is exactly what I'm talking about. You epitomize every single word. You live the words you share with others. I mean, this personal evolution that you're on seeking this mastery, I'm here for it. I'm so excited. I cannot wait to see you in bigger and better stages taking
I see you in such massive platforms. So keep going, keep doing you. You're such a bright light. I really do appreciate you. And the nuggets of wisdom that you've shared just in our hour together is something that I'm eternally grateful for.
Diann Wingert (55:27.118)
Hmm.
Diann Wingert (55:40.654)
Well, this is just the beginning for you and me, right?
Mic (55:43.933)
Yes, let's do this. So listen, is there anything else? Do you want to leave in our audience with some of your handles? Of course, I will include everything in the show notes, but how can people find you immediately and follow you and listen to you?
Diann Wingert (55:57.166)
Okay, what I like to say is if you like the sound of my voice and you like what I have to say with it, you should definitely check out the Driven Woman Entrepreneur podcast and I'm sure that you're going to link to it. And if you are either struggling to start a business or you are struggling in that business and you don't quite know like what is going on with me, I'm putting in the time, I'm doing the work, but I feel like something's holding me back. I created a quiz called, not surprisingly,
What's holding you back? And there are six different common patterns that I see with female solopreneurs, patterns of belief and behavior that tend to hang people up and make them less successful than they could be. So I'll give you the link. You can put it in the show notes. Take the quiz. It's going to tell you what your result is. And then you'll get a short series of emails that are going to give you a ton of resources for how you can start addressing that obstacle and getting it out of your way.
Mic (56:56.845)
Fantastic. This is wonderful. Thank you so much again for being here and remember listeners until next time. It only takes one spark to light the fire within. So make it a great day everyone. Thanks again, Diane.