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Good Life Project

7 Aug 2025 · 53m · 15 chapters

Episode artwork

It’s Never Too Late to Let the Real You Shine. A Love Story. | Sherri Dindal

In short

Sherri Dindal’s late-life reinvention—how quitting a 26-year investigator career, healing from trauma, and posting raw Gen X/midlife content led to millions of followers and a new identity centered on authenticity, joy, and “taking up space.”

Guest background

Sherri Dindal (“real Slim Sherry”) is a storyteller, comedian, entrepreneur, and founder of natural skincare brand Wholesome Hippie. She left home at 16, had her first child at 17, worked as an investigator for 26 years, and was married to a cop. She describes a traumatic childhood and years of masking, secrecy, and apathy as survival.

Key claims

Authenticity can be reclaimed at any age; healing is ongoing (no finish line); trauma and conditioning can be “unbecome”-ed; forgiveness (especially self-forgiveness) unlocks peace; Gen X women were conditioned to be “seen and not heard,” and social media can reverse that invisibility.

Notable examples

COVID illness in 2021 as a “second chance” to do deep work; a TikTok sound/Gen X post that rapidly gained ~40,000 followers; “Daily Dose” videos mixing humor, nostalgia, and tough-love healing; clapback videos used early to confront ageism, including blue hair/tattoos and cussing despite backlash.

Written by AI. May contain mistakes.

Chapters

4:04

Sherri's Transformation and Career Shift

Sherri discusses her journey from investigator to content creator.

“I'm somebody who's been And following along, laughing along, enjoying poignant moments and insights, fellow Gen X are here.”
6:11

Healing and Unbecoming

Insights into Sherri's healing process and the journey of unbecoming.

“And then you start discovering a bunch of people, millions of people, actually, that are like, that was my story too.”
8:20

The Power of Authenticity

Sherri shares the importance of authenticity and connection.

“I sort of started chipping away, not on purpose.”
10:49

Gen X Experiences and Visibility

Discussion on Gen X's experiences of invisibility and reclaiming space.

“And again, this collective of people that are like, hey, we were the generation that everybody, we were the forgotten, they call us the forgotten generation, right?”
14:03

Unpacking Generational Conditioning

Explore how societal and familial conditioning impacts self-identity.

“And I think apathy is sort of our hallmark of our generation.”
21:15

Embracing Change and Self-Discovery

Discussing personal transformation and the journey to self-acceptance.

“was there, was this a slow bill towards a moment or happening an incident that just shook you and said, I can't live as this person anymore.”
28:00

Finding Peace and Self-Forgiveness

Explore the importance of self-forgiveness and letting go of guilt for personal healing.

“If I had already had discovered peace and happiness and what joy felt like, because I used to believe that happiness was for other people, you know, and that joy was just like a joke.”
33:14

Reinventing Life Through Online Sharing

Learn about the host's journey of creating videos and sharing personal stories online.

“you get really ill with COVID and you recover and then you look around and realize so many others have experienced the same thing and are not here anymore or have long-term struggles.”
42:00

Breaking Societal Expectations

Learn how Sherri defies societal norms and embraces her authenticity despite criticism.

“And you hit a point where you're like, all right, I can't actually be me and do that thing, even though it seems like the algorithms remind me.”
45:30

Finding Freedom in Authenticity

Discover the liberation that comes from embracing one's true self and ignoring judgment.

“And some people just, they're just in such a bad place in their own lives that they would like to drag other people down with them.”
Show all 15 chapters
49:14

Embracing Life After 50

Understand the joy and opportunities that arise from living authentically in midlife.

“something that helps them to evolve, helps them to wake up.”
52:56

The Importance of Enjoying Life

Realize the value of enjoying life and living without regrets, especially as you age.

“We're sold this bill of goods that like you have to do everything when you're like young, because there's going to come a point when you're old that you're not gonna be able to do those things.”
56:00

Embracing New Experiences in Midlife

Discover how Sherri Dindal is saying yes to new opportunities in her fifties.

“I didn't have those were not in my cards.”
57:32

Defining a Good Life

Sherri shares her perspective on what living a good life truly means.

“Hey, before you leave, if you love this episode, safe bet you'll also love the conversation we had with Karen Waldron about rewriting the midlife narrative to one of joy, grace, and possibility.”
1:00:47

Defining a Good Life

Sherri shares her perspective on what living a good life truly means.

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Transcript

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0:00Jonathan Fields: So what happens when a former investigator who spent 26 years keeping her true self hidden suddenly decides at age 50 to just let it all out on social media? Well, when Sherri Dindal did exactly that, something remarkable and completely unexpected happened. Nearly 6 million people showed up to watch, to laugh, to cry, and heal alongside her. These weren't just casual followers. There were people, especially Gen X women, who saw themselves in her story of breaking free from decades of playing small and carrying trauma and silence of trying to fit into everyone else's boxes. And they watched in real time as she transformed from someone who thought joy and authenticity were for other people into a force of nature helping others reclaim their right to take up space.

0:45Jonathan Fields: I discovered Sherry in my own feed and Instagram one day and absolutely fell in love with how she shows up, how she tells stories, how just incredibly relatable and real she is. Sherry is known to her 5.7 million followers as the real Slim Sherry. She's a storyteller, comedian, entrepreneur, and the founder of natural skincare brand Wholesome Hippie. After 26 years as an investigator, she just completely reinvented herself, become this powerful voice for Gen X and a champion for authentic self-expression. especially for women who feel invisible or constrained by society's expectations. And along the way, she reclaimed parts of herself that had been dormant for decades.

1:23Jonathan Fields: And what makes this conversation so compelling also is how Sherry reveals the hidden gifts that often come wrapped in our greatest challenges. She shares how surviving trauma and learning to unbecome everything she was conditioned to be led her to discover a profound sense of freedom and joy. And her story really shows us that our most meaningful transformations can happen at any time at any age, that it's never too late to become who we truly are and to share that person with the world. So excited to share this conversation with you. I'm Jonathan Fields, and this is Good Life Project.

2:13Jonathan Fields: minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends, it's pretty much all he talks about in a good way. What's in your wallet? Terms apply. See CapitalOne.com slash bank. Capital One N.A. Member FDIC.

2:35Jonathan Fields: This episode is brought to you by Choiceology, an original podcast from Charles Schwab, hosted by Katie Milkman, an award-winning behavioral scientist and author of the best-selling book, How to Change. Choiceology is a show about the psychology and economics behind our decisions. Hear true stories from Nobel laureates, authors, athletes, and everyday people about why we do the things we do. Listen to Choiceology at schwab.com slash podcast or wherever you listen. Good Life Project is sponsored by Nature Raised Farms. So if there's one thing I have learned after 14 years of deep conversations about living well, it's this.

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3:52Jonathan Fields: No trade-offs, no second guessing. Look for Nature Raised Farms chicken in your freezer aisle and get back to simply enjoying dinner. Yeah, just really excited to dive into conversation with you. I'm somebody who's been And following along, laughing along, enjoying poignant moments and insights, fellow Gen X are here. All right. As we have this conversation, you're a storyteller, comedian, founder of a natural skincare brand, a wholesome hippie, a voice of Gen X creator. We'll talk about that because it's kind of like an interesting thing to be named that something like closing on 6 million followers on different platforms, brains behind the Gen X, some of the brains behind the Gen X takeover comedy tour, champion of all things Gen X and midlife, it's almost like you're on top of the world and sharing your true self.

4:39Jonathan Fields: But this wasn't your life always. This is a fairly recent moment in the history of your life. And I guess it was a couple of weeks ago, you shared a post where you were honored with an award that seemed to be really deeply meaningful to you. But in that post also, you start to share the fact that life leading up to this, the first 50 plus years or so, was profoundly different for you. So I want to take a step back in time and get a better understanding for what before times were like for you. I think I had a pretty standard, well, I can't say standard. I had a pretty common Gen X upbringing, I think.

5:18I didn't realize that until I started creating content. I started really making content and talking about the past and the history, my history. and what came from that was this discovery of a collective of people that were like, hey, you're telling my story. That was my story too. And I never realized it. I think you kind of go through life having your own experiences and whether those be good, bad. I had children and I've been married. And you do all of what life tells you you're supposed to do. You go through whatever you go through and then you land in this place where you're like, okay, this is who I am.

5:59When I turned 50, I just peeling back all of who I thought I was. And in discovering this collective of people, I think I also discovered I wasn't alone. And I think I always thought my experience, my past was unique. It was like, this is my story. And then you start discovering a bunch of people, millions of people, actually, that are like, that was my story too. And so it was comforting in a way. It was somewhat healing. It helped me to progress in my healing from my, you know, just again, my past and finding this space where I felt at home, I felt a camaraderie, a similarity, if you will. And it's been wild because I had a traumatic childhood and left home when I was 16, had my first child at 17, started a career, ran that career for 26 years, ran hard.

6:53That was basically my entire identity for most of my life, just being a mom and being an investigator. And those are the only things I thought I was good at. But I always had this gnawing feeling that I was supposed to be doing something else. I had some greater purpose that I just couldn't put my finger on. I couldn't really get past all of the baggage that I was carrying, I guess. And I finally quit my job. It'll be 10 years this year. I quit my job 10 years ago. I was burnt out. I was tired. I felt like I needed to be doing something different. And I didn't know what that different thing was going to be.

7:31I had zero clue what I was going to do. And I quit my job, started a business. And 10 years later, here I am. But three and a half years ago, even though I had quit my job and I'd started, I have a couple of businesses, actually. I started a couple of businesses. I still didn't feel like I was walking in my purpose. I didn't feel like I had really was, I just, again, knew that there was something greater that I felt called to. I just couldn't figure out what it was. And the reason I couldn't really figure it out is because all of the baggage was in the way. And so I started sort of this process of not just healing, but sort of unbecoming all of the things that I believed I was supposed to be and that I believe that I was and peeling back those layers and trying to rediscover the person that I always was.

8:15I just had become something I think other people had conditioned me to be. And so I talk a lot about that. I sort of started chipping away, not on purpose. When I first started making videos and content, I was just making them for me. I was, you know, they were therapeutic for me in a way to just start talking about these stories and memories that I had and trying to reconnect with a time when life did feel good. And I started chipping away a little at a time at some of those tougher, I guess, maybe even taboo topics or topics that people maybe suppressed and buried. And I know that I did. So yeah, I started telling some of the, some of what I consider to be just truths.

8:57You know, I think there's a lot of what you see online. You see a lot of people creating, you know, videos that are making, that'll make you laugh or they're doing dance trends or they're, you know, they're talking about this thing or that thing. And there's not a lot of real and you have, I guess the luxury when you create content to edit, right? Just like a movie that you make a movie, you can have the luxury of the edit and you get this well curated feed or pictures are perfect or the video is well edited. And a lot of there's, you just wonder sometimes how much of that's real. I, when I started making content, I was just doing that.

9:31I was just being myself. I was just finally for once being like, this is me and not the corporate version of me, not the version that everybody had raised me to be. I wanted to be raw and real and true to myself. And so that's what started to pour out of me and through these videos, like I said, that were therapeutic for me in the beginning to just really step into my authenticity and say, I'm tired of tempering myself and quieting myself or shrinking myself to make other people comfortable. And that's what I did. And what happened was millions of people apparently enjoyed that. And I'm not for everybody.

10:08I get that. I get that I'm not, I joke, I'm not everybody's cup of tea, but it's good thing I drink coffee because I don't really care. And, and it feels good to just, you know, finally, just honor myself and who I am. And in doing that, I think I honor a lot of other people, a lot of other people that wish they could have that kind of a voice or feel brave enough to speak their truth. And what's come of it is just this amazing ride of nostalgia and truth and again, authenticity and this sense of freedom, really. Just enjoying the ride and the freedom of being who I am and then also discovering friendships.

10:49And again, this collective of people that are like, hey, we were the generation that everybody, we were the forgotten, they call us the forgotten generation, right?

10:57Jonathan Fields: The invisible generation, yeah. Invisible generation, you know, forgotten. We still get skipped. You know, there's still TV shows or news shows that'll put up the generation. You'll see Boomer, the Millennial. They'll just skip right over us even now. And we're in our 50s. And the oldest Gen Xers are turning 60 this year, you know, which is crazy to think about. And so to think that all this time we're still being lost over or forgotten. And I love being able to breathe life into our stories and to give, not that we want attention, because Gen Xers are not one to want attention, just to, I think, to allow us to have space, to allow us to feel like we can take, we're allowed to take up space.

11:37We were raised on, you know, tough love and we're to be seen and not heard and brush it off, suck it up, rub some dirt on it. Like we weren't, you know, we weren't allowed to complain or whine or we often were, again, just kind of invisible and we were taught to be that way. And I think we've gone through our lives for the most part, living in that space and being okay with this is all the space that I'm allowed to take up. And we've accepted that. And now a lot of us are coming into this middle age of life, the ones that have survived that made it this far. I joke that our generation's the smallest because a lot of us didn't survive.

12:10And so the ones that are arriving at this point in life in their 50s and now turning 60 are like, you know what, I don't necessarily like that I have to live in this box that you've put me in. I want to take up more space. And I I hope that I give people the courage to do that.

12:23Jonathan Fields: I mean, there's so much that I'd love to dive into there. And I'm nodding along also because for so many people our age, this has been an experience. But it's also because part of the experience is that we don't talk about these things. And we don't talk about them in a public way, in a public forum. It's because we were the latchkey kids. We were the kids who were, you know, like whatever the opposite of helicopter parenting is, like that's what we experienced as kids. You know, it's like you get on your bike in the morning at some point. You wander home, hopefully not too bruised and banged up.

12:55Jonathan Fields: And it was really just the generation that was largely, in the early days, left alone. And then, as you described, as we sort of rose through life, became largely invisible. As somebody, we both started a number of companies, and nobody markets to Gen X. Nobody runs demographic groups for Gen X. there are very few products and services that are really focused on that sort of 45 to 60 age group. It remains to this day, largely invisible in the world of commerce and in service and in solution providing. And a big part of that experience when you're younger is the expectation that you're not really here to take up space.

13:37Jonathan Fields: And I'm curious for you, how did that actually show up on a day-to-day basis in your life? Oh, gosh, it showed up in, I think, almost every way. Again, going back to that idea of not just of being invisible, but being taught to keep yourself small and quiet. Again, that standard phrase, I thought it was just a phrase that I heard, that we were to be children or to be seen and not heard. and then I'm discovering millions of people who follow me or like, you know, that is so commonly shows up in my comments of, yeah, you know, when I touch on a topic that to what you said, we don't talk about, we just, you know, we've gone through life, we've sucked it up, we accepted it, that's what we were taught and for me, it showed up in a lot of ways of just sort of masking, you know, I think that it taught me to mask, it taught me to stay quiet, to keep secrets, to not draw attention to myself, it definitely taught me to be apathetic.

14:35And I think apathy is sort of our hallmark of our generation. It taught me to be apathetic. It taught me to be sarcastic. And a lot of those, what I've come to realize later in life is that those were survival techniques. Those were ways that helped me get through life and face all the, not just challenges in life, but the ugliness of the world. It helps your invisibility cloak to be even stronger, I guess. I think about how we as kids and then the way a lot of us were raised and the messaging that we heard from not just our parents, but from society in general. It wasn't just the people that were directly influencing our lives, but it was even just the general population.

15:18It's religion, it's your teachers, it's other role models in your life that have in ways passed on conditioning that as I talk about wires you a certain way. And it wired me that way and it showed up in my life every single day. And it's still, I'm still unpacking a lot of that. I'm still having to peel back layer by layer trying to get to the root of who maybe I really am. I never really knew that version of myself because it became buried under all that conditioning. And again, that hardwiring, it's almost like going in and ripping out those wires and allowing myself to believe that I deserve to feel happiness and joy and peace.

16:00And I deserve to feel a sense of freedom that I'm no longer bound by those that set of rules that were given to me and that were given to a lot of us. I mean, I think about that for the time, most of us came up with boomer parents, some had silent generational parents, but a lot of us thinking about latchkey kids. And when a lot of moms were going to work, you had dual dual income households that were really starting to evolve in the late 70s, early 80s. A lot of kids spent time with their silent gen grandparents. And so you had that conditioning and sort of a little bit of an even tougher love, if you will, in some ways, which is a lot of why the boomers are the way they are.

16:41But a lot of that was handed down from generation to generation. And the way that it shows up, I think for a lot of us, if we're truthful with ourselves, which I've had to really come into being not just telling truth, but being truthful with myself, is that that still shows up today in a lot of ways. It still makes us question ourselves. It might make us hesitate more. It might make us, again, that masking that I think a lot of us, especially Gen Xers, are so good at is putting on that tough face or that mask so that we show up the way we think other people expect us to or what makes other people comfortable.

17:19That was very much a taught, what would be the word? Sorry, words are hard because I'm 52. It was sort of a taught behavior or trait, if you will. And so it's, you know, it's learn. It's, I hope to share with people that you, that's not your destiny. You don't have to carry that around. That foundation that was built for you, you can tear it down and start with a new foundation that you're never too old, you're never too far gone, if you will. It's never too late to sort of reinvent yourself. And that's what's happened for me. It's just, and I never, never planned it that way. I didn't expect to be here where I am.

17:55Going from a person who was an investigator, most, pretty much my entire adult life, and towed a very hard line, working closely with law enforcement and just this, I was married to a cop and we both just pretty rigid people. You could be very rigid and you show up, you know, sort of in a more, can be a little bit more aggressive and assertive when you need to be, but also only when, only when you need to be. And I think coming up in that world made me even more, I was well conditioned for it, but I even conditioned myself even more to conform and show up in the world in a very particular way.

18:33And that just gets tired. Eventually, you get tired of that. That mask or that armor you wear gets heavy. As I moved into my 50s, I just was like, I don't want to carry this around anymore. I'm tired. It just was weighing me down and I wanted more. I try to share that with others in hopes that they'll find that discovery.

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21:13Jonathan Fields: For you, is this a gradual evolution? was there, was this a slow bill towards a moment or happening an incident that just shook you and said, I can't live as this person anymore. Like, this is not me. Like there's a part of me or maybe parts of me that I know are in there. Like in my private time, in my own mind, or maybe with my closest friends, I get to share that part of me, but I'm not actually living as that person. I'm not showing up as that person. And that's a heaviness that so many people carry, you know, Whether you're Gen X or not, that's a heaviness that I think, especially the deeper we get into life and we feel the responsibilities of life or maybe being a parent.

21:53Jonathan Fields: We kind of vary a lot of our identity in the name of towing the line, of being, quote, a responsible adult and fitting into whatever communities we're around. And you described the heaviness of that. It just builds and builds and builds. So I'm wondering, in your experience, was there a moment that just woke you up and said, no more? Or was it kind of like a gradual unfolding? It's actually a little bit of both. For me, it was always sort of this, there's always sort of been this something, but I never could figure it out. It was almost like there was this doorway that was locked. I knew it was there, but I couldn't figure out how to find the key or how to open the door.

22:32So there's always sort of this longing for something on the other side. but I couldn't find my way. And then there was this moment in time and that was 2021 for me. I got sick with COVID. I was pretty sick. I came out on the other side of that thinking that, yeah, I just was looking at the world through a different lens. At that time, everybody was feeling the weight of the world, this pandemic and people were dying and families were being torn apart where they were losing multiple people and their families to this pandemic. And I just came out on the other side that being very grateful that I had made it onto the other side, that I was here.

23:12And it was sort of a second chance for me. It kind of felt like a second chance, but it wasn't like my first second chance. You know, I had had a moment in time in my 30s, early 30s, where I had a horrific car accident. I was run under a semi and I walked away from that unscathed. Car was totaled. you'd have thought whoever was in that accident died. And I somehow walked away from that with a cut on my knuckle. I should have been, I was too, I think too young to appreciate that moment. I knew I was lucky, but I didn't really stop and appreciate all that had been given to me that I had had the second chance.

23:52And so I just sort of got back. I called somebody at work. I was in a company car, come get me off this freeway, got into another car and went right back to life. I didn't pause to really appreciate that second chance. It could have been a moment, I don't regret it, but I look back and go, man, if I had just figured it out in that moment, I could have got back another 18 years of my life that I wouldn't have wasted in that place that I didn't have happiness and joy and the freedom that I have now. And so when it happened again, and I felt like I'd had a second chance in 2021, I didn't want to waste it.

24:26And I started doing the really deep work, the hard work that I had always wanted to do. I just didn't know how to do it. I couldn't figure out how to get past certain things. And so I started really doing that deep, meaningful work, if you will, and just realizing the things that were holding me back was what I was holding on to, you know, that I couldn't find a way. Yeah. Well, you know, just the trauma that I had gone through and things that were still haunting me as an adult, you know, that I just, that had somehow kept showing up in my life, you know, these flashbacks and things that I think if I'm honest with myself, I couldn't let go of because in some way they were the only connection I had to the person who I was, right?

25:09Like this person that I lost through all of that. And so it was learning to let those go. It was learning to let go, learning to forgive, understanding and teaching myself that forgiveness is not a weakness. It's a gift you give yourself. It frees you. And it was coming to terms with those types of things and understanding that in the letting go process, I could start to find pieces of myself that I actually wanted to reconnect with. And that journey of healing, I used to think that healing was something you just did and then you were done. It's not. There's no finish line. It's not something that you're done with one day and then life is just great.

25:52No, it's more linear than that. It goes on forever. It's a process that you do day in and day out, and the healing itself gets easier. But you are always sort of in this process of evolution and rediscovery and learning about yourself. And it's the willingness to connect with that. It's the willingness to say, this is who I am. And these things happen to me, but they don't define me anymore, you know, and letting go of that. And I think a lot of people really struggle to get to that point of where they're okay with just letting go and forgiving and finding a place where they can be at peace. And that's what I had longed for my whole life was just a sense of peace.

26:30And I finally have found that. And like I said, it's still a process. I've come to terms with the idea that I'll always be in that some phase of that. but that it gets easier with time and letting go, being willing to let go of that armor that had been sort of woven into me through the conditioning and the trauma and all the beliefs. You know, the belief system that, you know, if you think about it, and a lot of people don't, the belief system that most of us carry was given to us. It's molded through your experiences and things that you do in life, but your early belief system is sort of given to you by someone else through the lessons they teach you and the expectations.

27:08And so it was coming to terms with the idea that I could still take parts of that belief system, that some of those things still are true to me. But I was allowed to start writing my own. I was allowed to start rewriting my own story and my own belief system in doing that. It's been amazing to come out of that and go, oh, this is what happiness feels like. This is what peace can feel like. And again, I hope for me in the stories that I share and some of the things I talk about is that I don't only affect my generation. I do talk a lot about my generation, but that I maybe will touch or reach or even older people sooner for the young people that they get there.

27:49I wish I could have done it in when I was 32, when that accident happened. Like if I had 18 years or actually at this point, it's 20 years ago. If I had that 20 years, like what, maybe where would I be now? If I had already had discovered peace and happiness and what joy felt like, because I used to believe that happiness was for other people, you know, and that joy was just like a joke. Like it wasn't real. You know, I didn't believe that it was something that existed, but it does. And you can find it. It's just often buried. buried, like I said, underneath all this other stuff, the baggage that we carry around that eventually gets very heavy.

28:22Jonathan Fields: You use the word forgiveness, which is, I think it's an interesting word because a lot of times when we hear that word, what we're thinking about is, well, who am I forgiving? It's another person, somebody who's done me wrong in my past. That may be a part of your story, right? But so often, the forgiveness that actually really unlocks so much of what we yearn to experience and feel is self-forgiveness. It's the parts of us that we feel have done other people harm or done ourselves harm that we can't understand often. And we just hold onto this blame and shame. And it's not directed at someone else.

28:58Jonathan Fields: It's literally directed to a part of us that we've kept down inside. And we're just, we were carrying that heaviness. So the forgiveness, I think a lot of times when people hear that word, it's like, well, who am I forgiving? Who's the person out there. But so often, it's a part of us that actually gives us the greatest relief. And also, in my experience, it's often the hardest one to forgive. I would agree with that because guilt and shame are two really big ones. And they're more internal. They're emotions that you feel for yourself. And so carrying around shame and guilt, I recently learned that shame is one of the strongest, if not the strongest emotion to overcome.

29:37And it encapsulates many other emotions that feed into shame. And so learning to shed that or learning to forgive yourself. For me, the shame and the guilt that I carried around wasn't something that I did, but I still felt some form of guilt and shame around that as if I somehow had played a part or it was somehow my fault. And I know now is one of the biggest things holding me back in my healing journey. I had thought back in my 40s, early 40s, I called myself healing. I was working on myself, but I realized that I wasn't. I had no idea what I was doing and wasn't being really honest with myself about what I needed to work on and what was really getting in the way of me finding joy and freedom or this feeling.

30:23Because freedom means a lot of different things for people, right? Freedom can mean what you feel is a sense of free, like we live in the United States and there's that sense of freedom, but then there's also the sense of freedom of just being able to do what you want whenever you want, or the freedom of being who you are and showing up for yourself first. And this is especially true for moms. We tend to not show up for ourselves. We show up for our families and our children often first. We will sacrifice ourselves. It's like the biggest sacrifice that moms make is for their kids, right? And so there's all these things that you can call freedom.

30:57But for me, freedom was just that. It was this ability to step into a place of peace and free from all the things that sort of I held for so long that just continued to pull me back into a past place that I didn't want to be. And I couldn't control that. And so that for me was freedom, was like, oh, I'm free of that. It has a place now. I have the power to control it. It doesn't control me any longer. That guilt and shame that you're talking about are two really large, big emotions that are hard to overcome, actually. And they are rooted in forgiveness.

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33:13Jonathan Fields: When you make the decision then in 2021, say this has been a slow build, you have this, you get really ill with COVID and you recover and then you look around and realize so many others have experienced the same thing and are not here anymore or have long-term struggles. This becomes a wake-up call to you. This becomes the second big moment where you're like, okay, I'm still here and I can't do the next season of life the way that I've done what's come before. So you make an interesting decision. I'm sure there are a lot of other things that you started changing and thinking about and people you were talking to, but one of those decisions that you described is I'm going to start just filming video and putting them online, right?

33:57Jonathan Fields: So you're, I guess around 49 at that point. So I was 40. It was actually 48. Okay. You're well into life. People know you in a certain way. You've got a certain reputation among the community. And then you're like, I am going to start creating videos. Now, for anyone who's seen your videos, we're having a grounded, calm conversation here. This is not the way that you show up in your videos online. You're funny. You're snarky. You're wise. You're throwing in tons of nostalgia points so that so many people can relate to so much of what you share. When you decide, and it feels like really apparent that this is not sort of like a made up character that you step into.

34:38Jonathan Fields: This is just a part of you that wasn't, it was being tucked away until that moment. So when you decide, okay, you know, I'm half a century into life almost, and I can't keep doing it the way that I'm doing. I need to actually show up as myself. And I'm going to start to just put up videos. Was this really just you? I just need to do this for myself and maybe five people will watch this. Or, or were you thinking to yourself, Maybe I can show up and inspire an entire community. Or what was going through your mind when you're like, I'm going to start just creating videos that are very different than the way a lot of people probably know me and just put them up?

35:14It actually didn't start that way. So while I was healing from COVID, I hadn't been on TikTok before that. I've been on some social media for years. I use them for my business, but I hadn't been on TikTok. and I think like a lot of people my age were like that's for teenagers and dance videos my I've got a couple of teenage young kids myself so I knew I was aware of it I was like yeah I wasn't interested but I found myself lying in bed for a month you know scrolling through that was what entertained me and I remember thinking I could do this like you know they're not the dance part but they were starting at that time people were starting to make content that wasn't just dance videos you know and so I was like oh I think I could do this and then originally I thought I would use it for my business.

35:58I was like, Oh, I'm going to start making videos for my business. And it never turned into that. I, in trying to figure out how to use the platform and learning the technology, you know, the first few videos I made out, they were just funny. They were just funny videos. They had nothing to do with my generation. I did not set out thinking anybody would see them. I honestly had zero expectations. I was just trying to learn the technology. And then one day, I don't remember why I made it, but I made a video that was the sounds only Gen X hears. And it was just opening clips, like few seconds of opening sounds to songs that would resonate, like would get you there like a dog whistle.

36:38As soon as you hear them, you know, you stop. And I made this video and it didn't do much at first because I was an investigator. My brain is wired to just go down the rabbit hole very, very easily. So I was down the rabbit hole trying to figure out how this stuff works. And somebody said, Hey, if a video doesn't work the first time, just repost it. So I did. And that I went to bed and I woke up and the next day, all of a sudden, I had 40 ,000 new followers off of that one video. I have no idea what's happening. I also fell into the trap early on listening to people who are like, Oh, you know, tick tock wants to put you in a niche.

37:11You know, if you try to make any videos or outside of that niche, then they are not going to perform well. So I was like, Oh, then I need to make another Gen X video because that video did really well. And so I started making videos about Gen X. I started just talking a little bit about just early on a little bit, just funny stuff about our generation. And slowly that built into storytelling. I've always been a chatty Cathy, I guess. And I love storytelling. I never really considered myself a storyteller, I don't think, but I could tell a good story. And so I started making Gen X, went right down into that niche and started making more videos for our generation.

37:50And that's really what started to take traction. So I thought, oh, that's true. You really just have to be in a niche and only do this one thing and those videos will do well. Well, what came from that was I get bored very easily. I can't only talk about this one thing. I don't have enough to talk about. Because of the trauma that I endured as a child, I don't have a lot of memories. You know, a lot of that's really just not, it's just a blank, it's just blank. And it's more like a movie reel, you know, little clips of stuff. I early on had a really hard time connecting with a lot of Gen X content.

38:23Cause I was like, I don't remember that much, but the, a lot of people would surprisingly comments would unlock a memory where I was like, Oh my gosh, I completely forgot about that. You know? And so it's been, that's where the therapeutic side of it came where I was like, this is very, this is good for me. It's helping me remember good things, right? I wasn't only holding on to the dark memories. And so it was good because it was helping me to reconnect with the good of my childhood, the stuff I really did love about growing up in the time that we grew up. You know, I mean, we were feral, but we were free.

38:55It was a lot different world. And that's been one of the most joyful things for me is that being able to reconnect with the nostalgia and the memories and the good times, right? I got bored. And I was like, I can't just talk about this one thing. And I'm not a believer in B. I don't like being told what to do. So that's just, I don't just don't, I don't like to be told what to do. And so I was like, you know what? Screw you. I'm not only going to do this one thing. I'm going to do what I want to do. And it felt genuine to make that content, but it also didn't feel as genuine as I wanted to be because I was like, I don't remember enough.

39:30And so I started talking about the one thing I could really talk about very authentically, which is aging. So I started talking, making videos about aging and midlife. And just why didn't anybody tell us that this is what the hell happens to you when you get to be this age? And I, you know, I've always been funny and very sarcastic, but I never considered my, I never really considered myself to be that funny. But I mean, if I look back, I'm like, okay, I've always been kind of funny. You know, those videos didn't take off right away. But then eventually those really started to do well. Also, also still connecting with the same audience just through a different genre, really, you know, it's like, Oh, we're all still at the same age, we're all going through it.

40:08We've all grown up the same way. And then menopause hit me. And so I started making videos about that. And those are hilarious, because menopause is just ridiculous. And so you can make fun of that all day. And I just broke the rules of the algorithm, which was that a lot of people do only just do one kind of thing. And I do multiple things. And through that, what came out of that was that I started making these daily dose videos because I was, again, they were therapeutic for me. They were funny, nostalgic, but then they were also somewhat healing. I was telling my own stories, but also the stories of others at the same time.

40:48And so what I recognized after a while of doing that, especially through the comments, was that there's this really brokenness to a lot of our generation. A lot of them haven't found a way out. They can't see the light at the end of the tunnel. They still are very much living in a place where I lived for so long. And so I started making these daily dose videos. They're kind of a tough love, kick in the pants, wake up type video. And they were really chipping away at some of the really tougher parts of life, you know, talking about the letting go and the finding peace and happiness and, and all of that.

41:24And so I ended up just being sort of this hodgepodge of content, you know, and it somehow worked, it somehow broke the rules. It's somehow not just on one platform, it wasn't just TikTok. That's where I started. You know, I started putting content on Instagram and Facebook. And next thing you know, now I've got, like I said, almost 6 million people where I still struggle to believe that there's almost 6 million people that care about one thing that I have to say.

41:51Jonathan Fields: I wonder if part of that also, you said you broke the rules of the algorithm, right? Which yes, you did. Because everybody tells you, choose your niche, stay really, like just boom, boom, boom. And you hit a point where you're like, all right, I can't actually be me and do that thing, even though it seems like the algorithms remind me. But when you decide, I just need to start talking about and sharing who I am and what I see and what I'm experiencing. you didn't just break the rules of the algorithm in no small way. You also broke the rules of culture, of society, about what a quote, woman of a certain age, the expectations about how that person would show up.

42:26Jonathan Fields: And you're like, oh, hell no. So it wasn't just the algorithm. It was bigger than that. Yeah. You just reminded me, I mean, especially early on. So I mean, I have blue hair. At one point, my hair was purple. I have tattoos. I'm 52. I cuss like a sailor, even though I'm being nice here on your podcast. I got a lot of hate early on. And I still do occasionally. I've learned to ignore it. You cannot dwell on the comments. It'll tear you down. But I used to see those comments and they would bother me. And at first, they did bother me. And almost for a while, made me even reconsider what I was doing, like putting myself out there.

43:09Because people can be so mean. I come from a time where if you talk trash, you get punched in the mouth. And now everybody does it behind their keyboard. So it's different. And so I didn't know how to deal with that, these keyboard warriors, if you will, the trolls. And so it almost discouraged me. And then there was a part of me that was like, no, that's not who I am. That just was more fuel on my fire. And so I started doing these clapback videos and started snapping back at people of their idea of ageism. I realized that in those moments, ageism was alive and well and how real it was, and especially for women.

43:49And so I used that as content. For me, that was like, you are low-hanging fruit. You are making this so easy for me. I can use this all day to chew you up and spit you out. And I did that for a while, and I don't do them as often anymore. Because A, I don't get in the comments that much for that kind of content. But I also recognize that I, the clapbacks, although people love them, my clapback videos always generally do very, very well. I realized that it wasn't really who I wanted to be. I didn't want to, you know, I didn't want to be here. I am talking about living in your, in your authenticity and, and, and being kind to yourself and finding peace and happiness.

44:24And then at this next, the next video, I'm handing somebody, you know, their entire dignity, you know, in one little video, 30 second clip. And I realized that it sort of was a little bit of a conflict for me. It made me come across in some ways almost as maybe being disingenuine, you know, that I was saying one thing and doing another. And so I'll still occasionally do it if it catch me on the right day, just rageful enough on the right day, I will still clap back. But I just, you know, I realized that that wasn't early on, it served its purpose. And people still say, oh, I really miss your clapback videos.

44:56But some people thrive on that. Some people just thrive on the negativity. And I didn't want to be perceived as negative. And those videos tend to be a little more in the negative space. And so I don't do them as often. But you're absolutely right that I did break all those rules. And not just what I say, and how I say it, but just in how I show up in general, right? The belief that like, you know, they're like, okay, grandma, with your blue hair, you're trying too hard, you know, those kind of comments, you know, and I'm like, I'm not trying this is just me. I don't have to try. I'm married. I got kids.

45:26I'm not planning to have any more kids. I have my own business. There's nothing that I need. But they don't get that. And some people just, they're just in such a bad place in their own lives that they would like to drag other people down with them. And so I tend to, like I said, I just try to ignore those people now, but yeah, they are out there and they come out in full force sometimes. Yeah.

45:44Jonathan Fields: And I mean, it's really when you, and again, as you were saying, like women are judged very differently than men, especially on social media where somebody can hide behind a screen or when there isn't really this direct thing. I mean, it's like, yeah, I don't know if you read Miranda July's All Fours, which is this tremendous book. But if you look at the reviews on that book, it's a novel about a woman in her 40s who's really just completely rediscovering who she is and what she wants out of life and sexuality and relationships. And a lot of the reviews on that book are like five stars and one star.

46:15What's it called?

46:16Jonathan Fields: Miranda July's book, All Fours. All Fours. It's so raw and visceral and powerful about what happens when a woman basically says, okay, I need to actually do this part of my life in the way that makes sense for me. And I know I've heard Miranda interviewed also, and she said she's taking a lot of heat. Some people absolutely love her and what she wrote and resonate so deeply in these all fours group chats going on around the world. And then other people just fiercely reject the whole notion that a woman in the middle years of her life could talk about things like this and show up in a particular way and consider these ideas.

46:55Jonathan Fields: And I see what you're doing as, it's so compelling in one way, because you're basically saying, just deal with it. This is me. Yeah. I tend to phrase it a little differently than that, but yes, you're absolutely right. It's like, you're not saying that overtly at all, but what you're saying is in the way that you show up, you're basically saying, okay, so I know who I am. And for decades of my life, I didn't show up as this person, at least in this way. And now I'm going to bring it all forward. And some of you may like that. Some of you may love it. Some of you may be inspired by it. Some of you may hate it.

47:30Jonathan Fields: Some of you may be threatened by it or offended by it, but that's not going to stop me from showing up in this way because I know who I am and why I'm doing it. And it feels right to me. I mean, does that land? Because that's the way it feels. I'm nodding because I'm like, that's absolutely, you know you captured that very well because that's exactly where i'm at and for me it wasn't until i was close to 50 for me to finally step into that space and it feels right it does it feels good it feels good to say you know what you said it way nicer than i would but screw you this is who i am and you don't have to like me because i don't care if you do or you don't you hit a point in life especially women i think finally hit a point in life where the especially the menopausal years for women where you just are like, I, yeah, this is who I am.

48:19Take me or leave me. But I don't want to be the version of me that you want. I don't want to be that person anymore. I lived that way for so long. I refuse to dishonor myself any longer for other people. For me, that deep sense of freedom in finding that of like, you know what? I refuse to dishonor myself any longer. And if you don't like that, that's a you problem. It's not my problem. And it feels, you feel lighter. You feel good to know that I feel good to know that I show up every day as this person who I am, the person I've always been, but tempered or hid or contorted for other people that I get to show up as this person every day.

49:04And that there are people out there that do appreciate it. There are people that look for that. They're looking for that little nugget of wisdom, something that breathes life into their day, something that helps them find courage, something that helps them to evolve, helps them to wake up. So many women, especially now that I'm on tour, so many women who come up to me and tell me that story of like, you saved my life. You have breathed life into a part of me that I thought was dead. And I don't take that for granted. It gives me purpose. I told you in the beginning, I didn't know it was this, but I always felt some sense of purpose that I wasn't fulfilling, that there was something greater I was supposed to be doing.

49:44I didn't know it would be sharing sage wisdom in my 50s. I had no idea it would be that, but it feels right. And I don't know where it's going to take me. I will continue. When I received the award that I received, I couldn't believe that I deserved an award like that. Like I really struggled. I was like, I was up for like three awards initially. One was for comedy, one was for motivational, inspirational, and the other was for the cheer of the year. And the first two felt okay. I was like, okay, comedy, sure. I can take that. Motivational, inspirational, I'll even give you that. But cheer of the year just really made me step back.

50:17I was like, I don't, I didn't feel worthy of that. I felt like there's so many people doing really like powerful, important things in the world that are deserving of something like that, you know? and when I won, I was in shock naturally, but so many people that came that either came to the comments or sent me messages that said, you absolutely deserve it. You've changed my life. You saved my life. They were near their end of their rope, you know, for, I don't know, a lot of people don't realize, but women in this age, uh, suicide rates are the highest for women in their midlife and especially late forties, early fifties.

50:53And so for them to have someone that they can look to, you know, that either makes them laugh or makes them think or helps them in some way to find whatever it is that they seek, whether that be peace or happiness or whatever, I will continue to show up for those people as long as I can, because I know what that felt like. I lived that way for so long to know that I'm helping even just one person, you know, is enough for me to keep doing it.

51:19Jonathan Fields: And also, you know, part of the way that you show up, there's this sense that, okay, so you know, this is resonating, you know, you're building an audience in the community and you're getting to show up and share parts of yourself. But like a big piece of this also, at least from like, from the outside looking in is it looks like you're genuinely having fun. Oh, I do. I do. And I think so many of us, we reach sort of like a certain point in life and we're like, oh yeah, the fun days, the carefree days, the loose, the goofball days. That left when I was 16 and I was just bouncing around with my friends.

51:52Jonathan Fields: And this is not the season of life for that. And you're showing up, you're like, no, no, no, no, no, no. This gets a seat at the table. And it looks like when you show up, it really looks like you're just having fun. And it's a reminder that says, oh, this can happen. This matters. You can show up this way. Some people may dismiss you, but a lot of other people actually won't. And a lot of other people will say, oh, I want some of that. I hope that they do. I am genuinely having fun. I look back at my early videos, where I was to where I am now, and just seeing how that's evolved and how much fun I've allowed myself to have.

52:34I think touching on what you just said about, you know, we believe that that all goes away because that laughter and fun and carefree spirit is only for the young. We're kind of taught that. I mean, there's a video going around right now, for example, where they're like interviewing people on the street saying, what year do you have to be born to be considered old? You know, and it's these kids that are like, oh, you know, 2000. And I'm like, oh, 25 is old now. Like I had no idea. It's this idea of young, right? We're sold this bill of goods that like you have to do everything when you're like young, because there's going to come a point when you're old that you're not gonna be able to do those things.

53:13And that's a bunch of trash. Like that's not true. For me, the best of my life is just starting. I mean, yeah, I've got my kids, those parts of my life will never be outdone. But I'm doing things in my 50s that I would have never done in my 20s. I would have never shown up the way that I do now in my 20s. And there's something to be said about, especially at this point in your life, of showing up authentically and just really enjoying the ride. And that's one of my standard lines. I say it at a lot of the end of my videos, especially my daily dose ones of just enjoy the ride. And I don't say it quite like that, but you just got to enjoy every moment of it.

53:49Life is so short. And we take for granted every day, every hour, every minute that goes by, We just take that for granted. And it is truly wasted on the young. And when you're young, you think you've got all this time ahead of you. You've got your whole life ahead of you. And those two second chance moments that I had taught me that those could have been snuffed out like that. Like that life could have been over. And all of those things I could have done, should have done, the regrets that maybe I would have had of the things that I didn't do, I don't want that for myself anymore. I just want to live and enjoy what life has to offer because you know what?

54:26It could be gone tomorrow. I don't want to be on my deathbed and look back and have regrets. And if I had continued to live the way that I had, I would have so many regrets. Just enjoy the ride, whatever the ride is, you know, whatever it is, enjoy it. Do the things that scare you and do the things that make you come alive. And those are the things for me. There's so many things that held me back because I was scared. Now I'm like, whatever it is, what it is. I'm going to do it. I'm going to do the hard things. I'm going to do those things that scare me because those are the things that for me, they make me feel alive.

55:02And then the things that make you feel, you know, that make you come alive, what those are the things you're passionate about. Those are the things that, you know, for, I tell with work, if you do a job that hit me, you hate, it literally drains the life out of you. I used, that was me get up every morning and literally cannot stand the idea of having to crawl out of bed and go to this place that feels like a prison. You should be doing something else. but find something that sets your soul on fire, that gives you life, that breathes life into your fire instead of snuffs your fire out, you know, and do those things because life is short and you don't want to get to the end of your days, whether you die slowly or you die suddenly and look back and go, God, I wish I had done those things.

55:46That's where I was after my second, second chance was like, man, that could have, it could have been gone. And I wasn't even 50 yet. And now I'm 50 and 52. I started really making that content at 50, but 52 be 53 this year. And I'm doing things I never imagined. I didn't have those were not in my cards. They were not on my being a content creator, going on tour, doing standup comedy. None of that was on my bingo card. Okay. It wasn't on my bucket list. And here, yet here I am in my fifties, suddenly doing all these things that I never would have done in my twenties or thirties. If you would have tried to convince me to get on a stage to do standup in my twenties, thirties, forties.

56:23I would have laughed and been like, there's no way. I would have never said yes. But I'm in my yes phase of life. I'm in the point in my life where it's like, say yes to everything that you possibly can. Because our days get shorter, not just in the sense that they go by faster, but we just have less time on this earth. And so you just got to do everything that you want to do and can do while you can still do it.

56:45Jonathan Fields: I love that. Feels like a good place for us to come full circle too. And so I always wrap these conversations with the same question. I kind of feel like you just answered it, but I'm still going to ask you in this container of good life project. If I offer up the phrase to live a good life, what comes up? To live a good life is not wishing that you were somebody else. Every time you wake up, you just wishing, not wishing that you were someone else live a life. The good life is living a life every day, just being who you are and not wishing you were someone else. And that's the good life for me.

57:17That's freedom for me is just being me. And yeah, I think that sums it up for me. Just waking up every day, not wishing that I was anybody but the person that I am. That's a good life.

57:31Jonathan Fields: Thank you. No, thank you. Hey, before you leave, if you love this episode, safe bet you'll also love the conversation we had with Karen Waldron about rewriting the midlife narrative to one of joy, grace, and possibility. You can find a link to that episode in the show notes. This episode of Good Life Project was produced by executive producers, Lindsay Fox and me, Jonathan Fields. Editing help by Alejandro Ramirez and Troy Young. Christopher Carter crafted our theme music. And of course, if you haven't already done so, please go ahead and follow Good Life Project in your favorite listening app or on YouTube too.

58:05Jonathan Fields: If you found this conversation interesting or valuable and inspiring, chances are you did because you're still listening here. do me a personal favor a seven second favor share it with just one person I mean if you want to share it with more that's awesome too but just one person even then invite them to talk with you about what you've both discovered to reconnect and explore ideas that really matter because that's how we all come alive together until next time I'm Jonathan Fields signing off for Good Life Project

58:42Jonathan Fields: With no fees or minimums on checking accounts, it's no wonder the Capital One bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends, it's pretty much all he talks about. In a good way. What's in your wallet? Terms apply. See CapitalOne.com slash bank. Capital One N.A. Member FDIC.

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1:00:21Jonathan Fields: Your team just added its 67th AI tool and also your 67th security blind spot. The good news? The Vanta agent works like a GRC engineer in the background, finding every app your team uses, scoring the risk, and drafting fixes for you. Vanta is the platform used by over 16 ,000 fast-moving companies like Ramp, Cursor, and Harvey, who are shaping the future with AI and staying ahead of AI risk. Get started at Vanta.com.

1:01:01Thank you.

From the publisher

What happens when a former investigator who spent 26 years keeping her true self hidden decides at age 50 to let it all out on social media?


Meet Sherri Dindal, who transformed from living life behind a mask to becoming The Real Slim Sherri, amassing 5.7 million followers by showing up with raw authenticity, humor and hard-won wisdom that's inspiring a generation of GenXers to reclaim their right to take up space. Her story reveals how two brushes with death led to an extraordinary reinvention, proving it's never too late to become who you truly are.


You can find Sherri at: Connect with Sherri | Wholesome Hippy | Episode Transcript


If you LOVED this episode, you’ll also love the conversations we had with Karen Walrond about rewriting the mid-life narrative to one of joy, grace and possibility.


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