We Should Not Have Access to This Much Power With Meg McKeen
In this all-new ep of AUIMLB, returning guest Meg McKeen joins Mary for a conversation about what happens when you stop following the script and start building a life on your own terms. From becoming a full-time digital nomad to running innovative networking events and empowering women in traditionally male-dominated industries, Meg shares how curiosity, experimentation, and a willingness to challenge convention have shaped her path.
To learn more about Meg, visit her website: https://www.adjunctadvisors.com/
Check out her podcast, "Bound & Determined": https://www.adjunctadvisors.com/bound
Follow her on Instagram: https://www.instagram.com/megmckeen/
And see her live on her Midwest podcast tour: https://www.adjunctadvisors.com/livein2026
Have a question or thought for Mary? Leave us a voicemail for your chance to be featured on the show: https://www.allupinmyladybusiness.com/voicemail/
Don’t forget to subscribe so you never miss an episode, then come hang with us on Instagram (instagram.com/allupinmyladybusiness) & Threads (threads.com/@allupinmyladybusiness)!
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My business is your business. It's all within my lady business. With me. Mary meets me. I'm so happy to have you here again.
SPEAKER_02I'm so glad to be here again. It it is always a hell yeah when Mary asks. So I'm grateful for all the little ways in the intersections of our lives and stories. So happy to be here with you today.
SPEAKER_01Yeah. Welcome to everybody else who's also joined today for this meeting of the Ms. The meeting of the M ladies. I'm once again joined by Meg McKean. Right, you've been on before, right? Yeah. Yeah. I uh I as I was saying it, I'm like, yeah, she has, or do I just spend a lot of time thinking and talking about her? Well, let's say both is true. That's super stupid. All of these things are so true. I just love you so much. So, Meg, uh, I don't even know how to begin a digital nomad. Do you refer to yourself as a digital nomad? That is what the that's what they say out there. Meg used to be here in Chicago and I saw her all the time, and then she was like, I don't want to be here or anywhere anymore. And so she sold all of her stuff and now she just floats around the world being cool and hot.
SPEAKER_02I do float. That I'm not on like a magic carpet or uh uh exhibit in a parade, but I do travel around and yeah, it's been five years of living this way, more than five years now. And it it really works for me. It works for my nervous system, it works for my business, my life. And I'm really, really glad that I took the the proverbial leap five years ago.
SPEAKER_01Um, and I mean, you know, you've got you've got the ability to do that, like to be able to just float around. And it's amazing, like I feel like there's a lot of people that would love to be able to do what you're doing. I would love to be able to do uh what you're doing. Like not having a place, like what is why do you think it works so well for you to be able to just not have like a home? Like, do you have do you have anything you consider a home base? I do not.
SPEAKER_02No. Um I'll share just maybe some interesting tidbits about the infrastructure of a nomad life. You do have to be a resident of somewhere. And so I have basically a post office box in South Dakota in Sioux Falls. And I am a citizen of South Dakota now, a resident of South Dakota. It's where I get my mail. It's where I travel once a year to go to the doctor, it's where my car is registered, my business is registered, I have a South Dakota driver's license. South Dakota is one of just a handful of states in the United States that are friendly towards full-time travelers. So when I tried to do this in Chicago, I just ran into obstacles left and right because the system wasn't built for people like me. And so I was constantly, honestly, trying to cheat the system to make it work. And as a woman who prefers to live in her integrity, I realized several years ago I need to get a better system in place here. So I'm I'm not hiding anything. I'm not or like someday the rug's gonna get pulled out from underneath you and you're gonna have to like I was bringing people down with me. You know, I was using a girlfriend's place for my driver's license. And I'm like, yeah, but I don't live there, and that's gonna affect her a lot of different things. And so this felt um felt like the right move. And so, yeah, so I I technically do not have a place of residence, a physical place, but I do have residency in South Dakota.
SPEAKER_01So I have a real why South I understand that they're more empathetic to the cis to the the life you're trying to lead, but like South Dakota, like does that mean you vote in South Dakota? It does. That's cool. I mean, unless you turned, I mean, even if you did turn. I mean, I don't know.
SPEAKER_02I didn't know you're we're we are on the same page and we are we are aligned there. And it is the one, the one part about this process that has not been easy, and I learned that the hard way. There was basically the bottom line is locally they don't want full-time travelers to have an opinion about what's happening in South Dakota because we're not there. It's fair. I'm also not paying an income tax to the state. I'm not utilizing the resources, I'm also not contributing to the resources there because I'm not there. And so where do you file your taxes? South Dakota.
SPEAKER_01So they are you aren't paying taxes to South Dakota?
SPEAKER_02Well, no, I'm using South Dakota. They don't have a state income tax. What? So there yeah. There's no personal income tax there. So when you ask why, there are many layers to the decision where you choose to attach yourself. And that one had a uh has a significant financial upside for me as a business owner, but also as an individual. It's a dance that I do, full disclosure. I work in insurance. It's a very um conservative industry by definition, by design. I have really strong relationships with uh a professional group in South Dakota. And we don't typically talk about politics because we're not aligned. And I have had to do some of my own internal work to remember what it is I'm there to do and the contributions I want to make to the lives, particularly of the women that I work with. And can we do that in a way that is professional and respectful and both allows us to get done what we need to do with this kind of obvious mismatch? Um and it's it's not easy. And there are days that I I do struggle with it. But I've also gotten to know some really, really wonderful people in South Dakota and everywhere else that I have traveled that have really challenged me to let go of some of my bias and my stereotypes. And when you live the way that I do, it would be rude and inappropriate of me to come to any new city with an expectation about what is true or untrue about it. And so traveling this way has allowed me to see parts of our country that I had never spent any meaningful time in and honestly get to know the people there, the local cultures, customs. I did not know what a big deal college football was in Oklahoma until I went and said, Like I had no idea, for example. And I have hundreds of stories like that. And I do think as humans, as citizens, as people navigating our own journeys, we should be spending more time in places that maybe make us uncomfortable and maybe make us question some things and challenge some things. And I very, very much was living in in a very happy bubble in Chicago, but it was a bubble.
SPEAKER_01So Yeah. I mean, I I'm from I feel like this is the second time I'm bringing this up on the podcast recently, but when I'm from Nebraska, as you may remember. Yeah. And Oklahoma is like the or like the the like one of our biggest rivals is the Oklahoma Sooners. We, as if I'm still part of it. Um, but when I went to University of Nebraska at Lincoln, there was a t-shirt you could get in the student union that said, um, Oklahoma sucks, but Colorado swallows on the back. Um and uh yeah, anyway, just some mild homophobia that you could purchase with your meal card. Yeah, right. Um great. Yeah. Why so when you go to places like Oklahoma or Grand Junction, Ohio or Grand Junction, Colorado, where you presently uh your butt is, um, like these are a lot of like very kind of rurally, like why do you wind up in those places?
SPEAKER_02Well, there's a different, a different rhyme and reason for each of them, but uh sometimes it's work, you know, it's where the the jobs are, where the clients are. Because I work on a, I'm a consultant, so it's a lot of project-y kind of stuff. I'm in Grand Junction right now. I'm I'm partnered and he's from here. So we're spending some time with family of his that lives here. So this is his stomping grounds, it's his playground. And so um, we're hanging out for a bit. I will say, overall, having moved to Chicago when I was 30 after a divorce and really going all in, gosh, I love Chicago. I still do for many, many ways and many reasons. It really held me in a season of transition. I made great friends, I love live music. I mean, it is a city that if you want to be busy and surrounded, you can be anytime, day or night. I also have evolved as a woman. I know myself better, I know my nervous system, I know what I need. And towards the end of my time in Chicago, I was craving um just a lot less noise, physical noise, but also the noisiness of constantly looking over my shoulder and kind of worrying or anticipating what was going on around me and thinking 10 steps ahead. And and I knew that I mean, I loved and still did love that chapter, but that I was ready for something different. I just didn't know what it was. And so as I've traveled, I have intentionally avoided New York City and Miami and LA because to me they are so different from Chicago, but energetically they feel the same in my body. And so I've been, I have spent a lot of time in what I call the little big cities in Cincinnati and Tulsa, and um I was in Maine and Portland and Portland, Oregon. I mean, I've been all over and do find myself really thriving in liberal college towns, are kind of my if I'm going into Claude and I'm figuring out where I should spend some meaningful time, my parameters are um pretty much that. I like to be in a university environment. I want to be able to walk. I want people to be engaged and interested in their community and what's going on. And that seems to be in alignment for me in terms of what I'm looking for in my life right now.
SPEAKER_01Yeah, I mean, I it's I also want to go back to you using Claude for that. Like I don't, I I I don't really use AI. And I I when I hear people that I know and like that are using it for like interest, I'm like, that would never occur to me to like use Claude to figure out where I'd want to go. Like I use like when I when I use AI, it's like usually like, you know, make sure that my I've got you know tense agreement in my verbs or whatever. Like I'm not, I don't know. I actually don't know. I maybe, maybe I am being left behind by AI because I just don't understand it. Um, but like how how like I I wanted actually let's just talk about it. What like using AI for that?
SPEAKER_02How do you use AI in your I I have to say, I don't know. I don't know if we're if this episode is gonna age well or or one or both of us is gonna come back 10 years from now being the fool. I don't know. I also, you know, I think about when the internet was a thing and cell phones became a thing, and and there's a certain amount of resistance that I think is healthy and appropriate. And I think we're asking good questions. I'm hugely interested and curious about the environmental impact and what every little query I'm putting in there is doing. Um, I'm not oblivious or ambivalent to that or what's happening in the workforce. I also don't want to be one of those people that, and that wasn't, that didn't really come out right, one of those people. But I do want to be a person that is curious enough to see what things are about before I make a judgment. So it's interesting because the thing I don't use AI for, there are many things, but is my writing. I have found, and you know this, I'm a very prolific contributor to the nonsense on LinkedIn. And right now my feed is very, very one note. And I can tell that you can tell so hard. So some of the like can you feel it? Is it a feeling? Do you want to touch weird questions that like I know these people? Like, I'm fortunate to have actual relationships. These are smart people, and I see them running their original thought through AI and thinking that the finished product is better and it's not. I miss, I do miss the humanity of it. And so I made a decision very early on when you know AI was still like, what does that stand for? Um to not use it for my writing because I think A, I like to write and I think I'm a good writer. So I I don't know that I need it, but also I think the cream is gonna rise to the top, literally. It always does. Yes. And so I will stay true and strong to my voice and the words that I choose and the clumsiness of it and the weird sentence fragmentation and all the things that I do that that make people want to read more. I'm gonna keep doing that.
SPEAKER_01And so I hate that the dash has been kind of taken away from me. I I feel like I can't use it when I'm writing because it makes it feel like I'm cheating and I'm not.
SPEAKER_02But like, isn't that the whole large language model? We gave it to them, right? We showed them that it's effective and we showed him as if I'm, you know, personalizing this stuff.
SPEAKER_01It's definitely a man. Claude is a man. They all are men.
SPEAKER_02Or Claudette, if you want to feminize it. But yeah, it's uh it's interesting. I do use it. You know, I'm I'm a one-woman show as a business owner. I'm there's a lot that I don't know. There's a lot of time that I spend ruminating and running around in circles and questioning things. And and I do use it as a sort of one-off um thing to bounce ideas or, you know, is this a total waste of time? Is this a shiny object for me? Uh, and that's been really helpful. One of the things right now that I've I've really leaned into, I'm taking my own podcast on tour. And there's just a ton of back-end logistical um venues are a big thing. I'm looking for a very specific aesthetic, a vibe, and energy where I host these things. And if you ask the question in in a really intentional and thoughtful way, it's pretty remarkable what comes back to you. And so I would say the majority of venues I found, I could have found through a Google search, but were actually kind of spit back to me through Claude. So that's awesome. I don't know. I don't know that I don't know at the end of the day if it's the right thing or not. I am not all in, you know, I've not completely systematized my business and I'm not putting all my personal financial data out. Like I'm I'm not, I'm certainly not, but I'm curious and in so many ways in my life, I've led with a sense of curiosity and it felt appropriate, feels appropriate in this case too.
SPEAKER_01Not gonna say I haven't used it for uh, I mean, I'm not like I'm like, I'm just never I mean, I definitely have used it. I'm not even gonna pretend like I haven't, but I haven't like it using it for like it, it seems like using it to figure out a vacation situation. It would never occur to me to do that, but it actually seems like a good use of it, like a way to do a better inquiry into something. I mean, I know it's not like an old lady. I'm like, did you know that you can use this bot, this bot inside the computer to do things for you? Yeah, we should not have had access to this much power. I it's I don't think that AI should have been a like a consumer grade like product that we have access to. Um, but then it's also like, but who do I want to have access to that? I want like scientists that are like, you know, trying to go towards progress. Um so let's go back to these events that you throw in these like the like the group that you're doing in like what what are they exactly?
SPEAKER_02Like when you're you're doing consulting things where you're going into like insurance companies and saying this is how you should sell things, or are you like I yeah, I this has been eight years in July that I've been doing this, and it it is not, I cannot answer this question succinctly or logically, but everything I do is in the insurance industry, but I do a lot of different things and I call them odd jobs with like so much respect for myself that it changes every day and it changes every quarter and every year, depending on what the industry is asking for, what I think it needs, and honestly what I want to be doing. There are things that I did in the earliest days of my business that I don't do anymore because they're not in alignment for me. I did it, I needed to make some money, but there's other people that do it better, or it's just not the energy that I want to live in right now. But right now, a huge part of what I'm doing is speaking, particularly to groups of women inside the insurance industry. And sometimes those are private companies that bring me in, and other times they're larger member-based associations, like I talked about earlier, that have actual conferences and conventions to support women in the industry. And nothing I do is technical in insurance anymore. I don't talk about coverage or pricing. I know those things because I've been here for so long. But everything I'm doing right now attaches to what I call the human experience that we're having as professionals. And so sometimes it's sales coaching because there's an element, obviously, of humanity in the way that we're doing that. I will go into companies and do private workshops on change management and on some leadership topics. But the podcast features women in the industry, their stories, women that are adjacent. Our mutual friend Katie has been on. She's my sobriety coach. I had her come on and talk about sobriety as a lifestyle choice. And still to this day, that episode has performed exceptionally well. But in general, I wanted to create an environment where one woman who's driving home from work or feeling a certain way would know that she wasn't alone. There was another woman figuring it out just like she is as she goes. So that was six years ago. The podcast is now a hundred episodes. I've had a lot of fun playing with all sorts of different experiences related to the podcast. But I love being in conference environments and being on stage and being in the room, but there's a certain intimacy to it all that I have really missed. And I can create that as an MC, as a host, as a guide, but I really wanted to be in not hotel ballrooms where the air conditioning is too much and the chicken breasts are dry. Like I want to be in spaces that are creative and thought-provoking in small groups and kind of get to the heart of it. And so the podcast tour, as I have called it, is really it's everything I have wanted in the way that we connect and relate in person that I was missing. Nobody else was doing these sorts of small-scale, intimate, non-conventional events. And so I did the first one in Dallas several years ago. I didn't actually record it. It didn't dawn on me to record it, but I invited a woman from the local community in Dallas. We had a group of gals sitting around a table in a really cool workspace and we chatted for two hours. I gave them snacks and a journal, and they went on about their lives. And then the next year I took it to Ohio and I had several stops in Ohio. Last year I went to eight cities up and down the Pacific Coast Highway and kind of meandered my way there. This year I'm headed to the Midwest by popular demand. It's also my roots in the industry, but also in my life. And so it's in in many ways like coming home. And there's six stops this time on the tour, all in the Midwest. And basically, without boring everyone with the details, it's two and a half hours on a weekday morning. I provide coffee, tea, a very easy breakfast. I sit in conversation for about 30 minutes with another woman. We record that, and that becomes a podcast episode that goes out into the world via the feed. But then after the recording is done, we turn off the equipment and we just have a conversation for the last hour or so. And it's a chance for the women in the room to ask questions of me, of my guest, of each other, to share what resonated, where do what thread do you want to pull on from that conversation? And then they like go on about their day. We're done by noon. So they can go back to work if they need to. They can go home and have the rest of their day, get the kids off the bus, like all the things that we are pulled to do as women, we can keep doing those things without this massive hardship, but still getting this nice like shot in the arm of connection and intimacy that I believe and I know so many of us are really craving. And the cool thing is, and I'm really happy with the way the Midwest tour has come out, all the businesses that we are meeting in. So we're meeting in art galleries and a candle making studio, a bookstore, a cooking uh like cooking class space, all of them are owned by women. So they're local small businesses, and we're supporting them obviously by hosting these events in these spaces. And so there's this cool just trickle down effect that we're having in the local communities. And because I travel full time, I come to you. And so I'm not asking you to book a like I'm going to be in Omaha in September. And you don't have to, maybe you have to drive an hour if coming from Lincoln is a big deal, but it's not a big deal in the grand scheme of things. And so I've been able to marry my lifestyle choices, my decision to travel and to talk about the things I want to talk about and and do small scale events. Um, it works because I have corporate sponsors that see the value in these things. Tickets are 25 bucks. Who comes to them? Women in insurance. And that's all that I all that I say. And sometimes I have some gals that are just in my life that, you know, my mom is coming to Grand Rapids because I'm never gonna tell my mom she can't she can't come to one of my events. Um, Chicago will be a lot of friends because again, I don't lock down the tickets and um it's gonna be really fun and something a little bit different. But mostly women in the industry and some of them know me, many of them don't. You know, they find out through word of mouth or social media that I'm doing this. And it's just different and it feels good and in alignment for me.
SPEAKER_01So the podcast tour is something that you is this how you record your podcast. This is just like a one part of your podcast is that are we these episodes and then other episodes are just regularly recorded. Yes, guys. Exactly. Um and so that sounds like a fun way to spend some time driving around.
SPEAKER_02There are there are these moments when I was in so doing the tour last year, I started in essentially Seattle and drove to San Diego and had several stops along the way. And I remember driving through the redwoods in California, just like taking the long way and thinking, as you know, and we talked about in our last conversation, I work in the insurance industry, but I have been kicking and screaming the whole way. It it's my choice to be here, but it has been a struggle to find the ways that I can be me in an environment that in so many ways feels like it wasn't built for me. And so I'm driving with, you know, this banner in my backseat and in a case of, again, like journals and swat. Like I'm I'm having this out-of-body moment thinking I can't believe A, that this is my life, but B, that this is what I get to do to make a living. Like this is what pays my bills. And there's other things, of course, that are less creative and less, you know, maybe fun or different or outside of the box, but all of it together has created an income stream that supports the kinds of things I want to do and the environments that I want to be in. And honestly, I did not think it was possible. I was my own harshest critic when I started doing this because I just, I just couldn't see the path.
SPEAKER_01Well, I mean, it's, you know, I think, especially, I think I think about when I was a little girl, and the only thing I thought that I could do as a job was either a teacher or a nurse. I mean, that's that was basically when I was a little girl, that was like kind of the only thing that women were, you know, and like if when you terms of when you thought about a job. So I just thought to be a teacher because that's what women did. Like I, and it's weird, and so I think that for our I think that, you know, I think we were sort of getting more messages, I guess, to a certain extent. And then the next the generation behind us definitely got more girl power and all of that. But I don't think it's surprising that you are doing something you could never imagine because there were a lot of not a lot of things for us to even imagine to be. And, you know, I think we've wind up we wind up joining this job force that was really like not made for women. I mean, it's all based around men's strengths and the things men want to do and the way they want to structure it and the moms at homes they don't have to think about breastfeeding rooms or period breaks or whatever the things that we, you know, would be ideal in a world that was even beginning to treat us as an equal in it. And so, you know, you in your redwood forest, you know, in your car driving around, like figuring these things out, it's like, you know, I having these moments where you're like, oh my God, I get to do this. I think that's because we you actually gave yourself the space to figure it out and find a way to make it work because you can't, I mean it's hard even say what you do. You know, like it's you know, like this morning I was at the gym and uh I had to go earlier today because we were recording this now. And they were like, What do you why are you recording, you know, what do why do you have to leave? And I'm like, Oh, I'm recording a podcast. Like, oh, you have a podcast and what's it about? And I find that can I can never really say what it's about because it's just like it's just women and me talking about with being a woman in the world, it doesn't really have a good thesis statement. And I feel like that's part of the reason why I I like don't really know how to talk about it or promote it or whatever, because I don't really have, but I don't want to necessarily define it either. My point to this all is is that when women do this, like you're not the first woman I know I've met that's like, I'm I figured out a weird way to make my life work. And it's always like, oh, it's weird, I don't know how to do it. And I do the same thing to myself. I mean, it's everything I do is, you know, weird for the average person, but by giving yourself the space to do this, can you imagine if more women were able to, if more people in general able to actually just think about what they actually want to do and how they want to do it and what it looks like? Can you imagine how weird and different and awesome the world would be if we could allow ourselves that kind of freedom to do that?
SPEAKER_02Yes. And I I want to say, you probably don't see this because you're in it. You see the world through your lens. But when we met, I was transitioning away from the corporate world. I had a lot of uncertainty about what was next. I did not think I was gonna stay in the insurance industry. And I would go to your co-working space at the time, and you gifted me a, or we bartered for a brainstorming session. And you showed me less through action, but just by presence, that you can do this. I did not want to build a DJ company. I did not want to own a co-working space, but you were evidence right there in front of my eyes that whatever thought I had that life had to look a certain prescribed way, that that was untrue. And at that point, I was already divorced. I had left the corporate world. And I do think, you know, confidence is a muscle. We build it over time, we only build it through action. And and you, Katie, other women that I've been so fortunate to know and just sort of like stalk respectfully, but also glom on to have shown me. And one of the I've I have given so much resistance to not focusing solely on the insurance industry, and so many, so many people challenge. Like all the stuff you talk about. It's relevant for women all over the world. Why are you only talking to insurance people? And part of it is strategic. They know me in the industry. I have I've worked for some great companies. I don't have to sell myself the way I might have to in another industry. I also know the industry. And so I speak the language, I see the good, the bad, and the ugly. But I also have been the women that I'm trying to reach in the industry. I know what it feels like to sit in these offices that smell of like old mahogany furniture with, you know, brass, burnished gold hardware that hasn't been moved since 1980. Like I know a wall of really thick books that like, you know, you used to have to use, but you don't anymore, but they keep it there anyway. Yeah. And they're they're plaques in our industry. They're all sorts of plaques, and the plaques mean different things. And I know what they mean because I've I worked in an office many times and there were plaques there. But there's all these little signals and symptoms of what's going on in the industry. And and I don't have all the answers, but I'm I know a lot. Um, I know a lot and I know how to be helpful and impactful in that space. And so I choose to stay there. I'm not, I don't disagree that there's opportunity outside the industry, but several women in the last maybe six months, and this is a this has happened. I've been doing this for eight years. I certainly don't have it all figured out, but I've figured out some things. And so women that are newer, just like I was when I met you, I see you, you are successful by my measure, and I want to figure that out. I want to know what your secret sauce is. And so now women are coming to me and they're asking me those questions. And, you know, of course it's so deeply personal, and and I can't, I can't shortcut the process for anyone. But it is fascinating now to look at my own journey through their lens and the things that that I've learned and the mistakes that I've made and what I would do differently. And I think at the end of the day, it's do you have a compelling story to tell? Do you have something that the world is curious about and wants to know more about it? And are you brave enough to open your mouth and and share it? And a lot of us are hiding, to your point, the beautiful, brilliant, life-changing ideas, I believe are out there. They're already out there. We are just sitting back, we are sitting on our hands, we're swallowing our words, we're scared to death. Like all, and all of that is true. And I have felt that way. The very first person I told, I initially my business, I wanted to just support women. Um, and I do many, I many of my clients are women, but I do work with men as well. Many of the people that hire me are men. And the first piece of advice I got back then was you can't work with just women that's discriminatory, and you'll end up getting sued. And I was like, well, you know, I have about six months of cash socked away, and I don't really want to spend it on what was discriminatory.
SPEAKER_01Wait, what why was this discriminatory?
SPEAKER_02Because of the world we live in. If you create spaces that are only for women and not inclusive, then there's a perception of exclusion.
SPEAKER_01And yeah. Despite the fact that the fight, despite the fact that most rooms are filled with white guys and they say that there's no re there's no discrimination going on there because everyone's welcome there, but are they really?
SPEAKER_02You said it very. And I and the thing, you know, and I support again, men and women in an ecosystem where it's it is largely, as you mentioned, affluent white men at the top. And so I struggle some days, many days, with you know, I'm I'm hosting these events, I'm having these conversations, I'm helping women to see their value and their worth. And and at the end of the day, they make more money, which makes more money, makes more money for for the people at the top. And in many ways, I I don't think the system, at least the insurance ecosystem, is gonna change dramatically in my lifetime. But I do think the way that we attach with work is changing. And I see a lot more women setting tighter boundaries around what they are willing to give to work and what they're asking for in return. And I think that's a win. You know, as much as I want to see sweeping revolutionary change everywhere, everywhere that it's it's needed, I'm also practical. And these systems were built to protect people in power. And they are protected and they have the power. And to let that go will require a major upset. And we haven't seen it happen yet in the insurance industry. And so in the meantime, it is a great place to make a living. And you can have a beautiful life and you can do the kind of things that I'm doing and that we've talked about today. But you also have to remember the wider ecosystem that we're playing in.
SPEAKER_01Well, it's interesting because insurance, I mean, I'm really glad there's a person like you that is in insurance because I feel like insurance is very much a male-dominated industry. I would, I mean, they're all, but it's insurance seems very opaque to me. And we all have to have it for all sorts of things. Most people a lot of don't have it. In my business, the amount of money I spend on insurance is insane. Same. And I don't even offer health. I'll I and the the the insurance that I have to, I have like six different types of insurance for toast and jam. And and it's like, and we keep having problems where we're having venues or whatever that are coming back to us and being like, you know, you have to carry this astronomical amount of insurance in order to work here. And it's like, you know, and where it's like, you know, they'll be like, you know, you need to have a pol like a, you know, like a $5 million policy. And I'm like, there isn't a universe where a DJ is causing $5 million worth of damage. And that policy is going to be so expensive that then I have to pass that price, that, that on to the client. So then our prices have to increase for a policy I'm probably never going to use. And then if I do wind up filing a claim, are they gonna cover it? Are they gonna say sorry that or they'll cover it, then they drop me? Like there's no, there doesn't seem to be any guardrails even around insurance anymore either on that as well. And it sucks because, you know, it's like I have it's like I there, and there's even policies that I can't even qualify for that I've been asked to have. It seems to be kind of recently that insurance had become more crazy. Or maybe my business has gotten to big enough to the point where I have to have these things.
SPEAKER_02Yeah, and that's true. I mean, you you have more people out there, you have more opportunities that you have more opportunities for things to go wrong. And you know, and insurance forces us to think about the hard days, not the good, the good positive ones, unfortunately. I I cannot answer your question cosmically about what's going on with insurance, but I will say, as a former practitioner of insurance, and I'm still licensed as an insurance agent, but I don't do any of that anymore. Um, I maintain it so that I understand what's going out there in the marketplace, but what's going on. But in general, you know, and I did listen to the conversation you had with your attorney about this specific issue. And I'm I'm like yelling at my phone as the podcast is playing. I'm just like, it's so frustrating, and I feel it too. I see these contract requirements set for me. And I'm like, listen, I'm just coming in to do a 60-minute keynote. I'm flying in, I'm not bringing a car, you know, I'm not, I'm not bringing a big A V setup, and you're asking me for a million dollars of auto liability. Granted, I have that because that's pretty standard, but it's this total mismatch between what we call the exposure that we present in insurance, you as the business owner, versus these sort of template boilerplate requirements that have put out, they're they've been put out for everybody. Every single vendor that comes on that property is getting the same requirements. And some of them, yeah, they need a $10 million cyber policy. Mary doesn't. And so this is where, and and this will be as like soapboxy commercially as I will get. Many, many, many of those things are negotiable if you have the right person negotiating for you. That is not your job. That is your insurance agent's job to look at what's being required of you. They're not attorneys, but they know enough to be dangerous and say, this doesn't make sense. This is not practical for the scope of what Mary's doing as a DJ, what Meg is doing as a speaker. Let's see if we can negotiate this. And in many cases, you can. The truth in insurance is it's there to pay claims. There's money built into the system to pay for the things that happen. And so anybody that's out there thinking the whole goal is to never have a claim, to never use it, that'd be great, but that's not practical. You are, you should use it, not every day, not for the little, like easy little I cut my finger onesie twosie things, but it's uh it's a tool that should allow you as a business owner to take more chances in your business because it's there and it's correct. When it becomes cost prohibitive, just like you described, and it means you can't keep growing and scaling your business because you've run into a brick wall, then it's time to do that negotiation. It's time to look at, okay, I mean, I'm not going to give you a masterclass in business. You could do that for me, but do you have to charge more? You know, I did a unilateral price increase in 2026 for a lot of reasons, but the cost of my insurance was a part of it. It guess what? It gets spread to everybody now that I work with because I have to eat that cost and I refuse to make less in this economy because of an expense like that. Right. I can't. I can't. And it's not all trips through the redwood forest, but I it does cost me to live this way and to support the life that I live. And ultimately, my so many of my clients benefit because of my mobility. I just happen to be in Indianapolis in November. So sure, you know, now you're not paying for airfare and a hotel and all that stuff. So it the net effect is it works out for my clients' benefit 99% of the time. But no, these are these are not easy questions to answer. The thing that we're running into right now is there is such a negative perception of insurance. And I have been guilty of spreading it. And I hope in what way? Perpetuating it's it's a money grab. It's, you know, you pay for this thing and you never need it. Like, where in our economy do you never get to see the product that you've bought? You know, I go to the dentist, I get my teeth cleaned. At least I'm somewhat guaranteed I won't have cavities. No guarantee if I do my part. But in the uh the lack of education around it, we create fear in you. And then guess what? We dangle an insurance policy in front of you that can just wipe that away. I've recently was sitting with a insurance salesperson and they were talking about the way that they they do this, the way that they sell insurance, and they ask all these really leading questions about all these scenarios that could go wrong in your life or business. And my nervous system, like my heart started to race, and I'm not even the client or the customer. And I'm like, why, why are you doing that? You know, Mary, at 3 a.m., when you wake up, you know what's on your mind. You know what you are worried about. What if we could solve that? What if we didn't create all of these other scenarios to freak you out and intimidate you and then sell you something? What if we brought you in to the competition?
SPEAKER_01On that same conversation, it's like, you know, it's like there are it's it's Mes Melissa likes to say like a circle jerk of liability, where it's like you're just trying so hard to make it so that you never have to pay the price of doing business. And that is something that, like, you know, like you can't it's like it it creates this illusion that you're pre you're covered on everything at all times. And then something happens where you actually need to use the insurance and either you didn't buy enough or this is the one thing they don't cover, or because the person was walking across the street when the thing happened and streets weren't covered in the policy or whatever. Right. And it does really feel like a cash grab. It does feel like, you know, the, you know, you all the all the horror stories you hear about people like hey, needing a liver transplant. The insurance company decided they weren't gonna get the liver transplant because, you know, the the You checked the wrong box or you put the wrong code on the form.
SPEAKER_02Yeah. I've heard those stories too. And in full disclosure, I don't insurance is very siloed segmented. I've never, other than a consumer of health insurance, I've never worked in that arena. And that's by design. It's a whole other beast. But your point is valid and you know, ultimately insurance companies, and I I do believe this, and I hope you know me well enough, I am not bullshitting you here, they want to pay the claims that they're obligated to pay on behalf of you. If you hire somebody, uh, and I don't know if you use subcontractors in your business or not, but if you did, if you hired somebody to come in and do some setup for you and they did something wrong, they left a cable, they didn't secure it to the ground and somebody tripped and fall, fell. Ultimately, you hired them. You would like their insurance to pay for that, right? If you don't have the right controls in place, it's gonna end up falling on you. And so people are trying to protect themselves, but they're trying to protect what they built. And the insurance company doesn't price for everybody else's mistakes. They price for yours. And so they're not wrong to ask about do you have contracts and do they include this? And do, you know, that all means something, unfortunately, in this very litigious world that we live in, that anybody at any time can be sued for anything and then hopefully ultimately dismissed. But there's still a lot of financial and emotional headache that go along with that. And so insurance is one of the things you can do. A lot of people are focusing, like, okay, what's within my control? What maybe I have I changed my hiring practices, maybe I ask better questions, maybe I'm I stop looking the other way when so-and-so says what he says to that employee because that's a liability. You know, there's there's a lot of layers to it. And I'll pause there because I, again, I I see both sides. I'm a business owner. I barf when I get my renewal because I'm like, bro, like I'm a small business. Like I don't just have unlimited capital sitting around to pay these bills. And especially if it's a year where you're not seeing remarkable growth in your business, but yet your premiums are growing remarkably. You know, that is hard.
SPEAKER_01Well, and we're seeing a year right now where like we are having like the last two months. I mean, you know, just uh it under the hood, like, you know, look, our leads are down, our our we haven't hit our goals our last two months. But whatever. I mean, it's not like you know, it's we're still making money. It's just not going a hundred percent the way it normally goes. And, you know, it's feeling very recession-y, you know, it's beginning to feel a little, little recession-esque. And, you know, I it's a thing where I don't know how to protect myself from that, but I don't know if I can. You know, like it's it's like if we're all going down, I guess we're all going down together. Um, I don't think I'm going down, but it it definitely is like when I look at, you know, EPLI and, you know, uh liability, umbrellas, all these other things I have to get. And it's like, wow, that was that's a and even work workers comp to me. I mean, I don't even get me started on workers' comp. I hate it more than anything in the world. Um, but because it's my biggest expense. Like workers comp experience is literally in one of my top four biggest expenses that I have for my business. A policy I've never had to call, I've never used knocking on all the wood. Like I've never had to use it. It's just very annoying to see that much profitability just disappear. And so, like on these, you know, in these months where things are a little lighter, it's like, geez, it'd be kind of cool to not be spending, you know, $3,000 this month on my workers' comp and my, you know, or whatever else I have to spend the money on. And it's, I don't know, especially when it feels like the whole country's falling apart and I still have to pretend like I'm running a normal business in a normal time.
SPEAKER_02Right. Same. And I I don't have the responsibilities that you have necessarily in my business, but I do feel the greater responsibility to what am I doing here and what is my what is my contribution. I I want to say, and this is Lighthearted and you left us on a very heavy note. But I want to go on the record. It was not the insurance professional, but it was you that went jargony on us that started talking about EPLI and workers' compensation. Like that is a hard and fast rule. I meet people where they are. I do not use terminology like that because if you don't understand it, and why would you? I've lost you. And I love that you went there. Those are very, very specific types of insurance that you can buy for a listener who's not familiar with the process. And as you're, you know, you didn't always have employees. And when you started to have employees, now you have a responsibility legally to provide workers' compensation. And you have to pay for that. You have to figure out how you're gonna make that expense every month. And I I have my own version of that, right? And I think the nature of what you do, what I do, where income is irregular, revenue does change seasonally and cyclically. And and I know you're you started Toast and Jam, right? Like at the end of the last major recession. And so you're coming in. Am I right about that?
SPEAKER_01Has it been like 20 years? It was actually the beginning. It was twenty two thousand five was when I okay.
SPEAKER_02So you you were in it. Oh gosh, that's so so you went through like those first several years of finding your footing all while the economy was trying to sort itself out.
SPEAKER_01Yeah. And I will say, like for us, it actually wound up working out for us because we were um, I think people that would have gotten bans got DJs. And so now I got brought into venues that I probably wouldn't have been able to get into um during the pandemic. And I think that kind of wound up elevating the idea of DJ as a reputable, you know, vendor. Uh, you know, I think I mean, I I that's my I mean, I don't have any like hard numbers on that, but that's my my anecdotal feelings on it are that like part of the reason why we got as good as we, you know, as as as successful as we did as quickly and solidly as we did is because we were able to get work in better places that we probably wouldn't have normally gotten into had the pandemic not happened. Or not the pandemic, the recession not happened.
SPEAKER_02Well, and I was gonna say the pandemic was a similar experience for me because I was a year and a half in when that started and just changed ever I mean, who knows what the business would look like if it weren't for that. But on the flip side, when things opened up again, because I had put my head down and kept going and talking about the things I wanted to be talking about, then when things opened up again and people needed speakers and they needed consultants to talk about these things, I was already there. And so it was this weird like, what am I doing in the middle of it? And then after it was like, oh, okay, maybe that, maybe it makes a little bit more sense now. So I don't know. I don't know what this next season is gonna look like. And I think we talked a lot during pandemic times about the pivot. And I think for a lot of us, that's what the answer looks like. And when I think about revenue streams and sources right now, I'm always thinking about what happens if one goes away, either by choice or by, I mean, the things happen. And so where can I continue to grow expertise and interest and a brand so that when things shift and they will, I'm still in a position to be able to benefit from that. So, and that's the strategy of all of this, right? Is like it can feel it can feel good, but also I need it to be sustainable and I I need it to support me.
SPEAKER_01Well, and you've been flexing that muscle for quite some time. I mean, I, you know, it's like with all of the layoffs that are coming around AI, it's like a lot of people are gonna have to pivot. I mean, I don't know where the billionaires think that people are gonna be paying for the things with AI has taken all the workforce away and they have nothing to do. Um, but you know, I there's I mean, it's kind of like how Airbnb and Uber came out of the recession and you know, do Uber Eats and all these other things got bigger around, you know, they all like the the downsides always produce, you know, interesting or innovation, whether it's good or not, that happens. And so something cool is gonna come out of right now. I don't know what it is exactly. Um it's hot flash dance.
SPEAKER_02Yeah, oh yeah. I mean, I it's so funny. I just shared uh that with a group of girlfriends. Um I'm like, y'all to see what Mary's doing. This is so great. And maybe it's that, or maybe it's something you haven't thought about yet. But I do think your your nature similar to mine is what do the people need? And does it make sense for me to give the people what they need and and be married to it to a certain degree and loyal to it, but also willing to try some new things. And I think that's the it's this, it's scary, but it's also I think where the joy people ask me all the time, like, why don't you just pick something? Why don't you go all in on, you know, be a sales coach, be a speaker, be a this, be a that. And it's like simply what fun is that? You know, I love that I get the chat.
SPEAKER_01Like I like I don't want to do that, you know.
SPEAKER_02You know, it's hard for people to understand what you do if you do so many things. And and isn't that volatile? And couldn't you create more consistency with revenue if you did one thing? And and like all that might be true, but as you know yourself, and I know you do, and I'm, you know, I'm figuring that out too. I think there's something, you know, really cool and empowering about like, yeah, cool, thanks for the wisdom, but I'm gonna do it, I'm gonna do it my way. I saw something on Instagram yesterday. I've been spending way too much time on the socials in general lately, but it was kind of like how cool that you're creating a life for yourself that no woman in your family has ever done. And the way I live, the way I relationship, the way I work, all of it is different than any other woman that I've known in the history of my family. And I was like, huh, that feels like a lot of pressure and maybe some ego, but also what does that mean to your earlier point? What is this gonna look like now for my niece who's 12 and figuring out who she wants to be in the world? And and she's got choices and options now that I didn't have or maybe I had, but wasn't confident enough to exercise. And I don't know, I like to be naive enough to think that we're gonna leave it better than we found it.
SPEAKER_01Yeah. I I definitely, I mean, I feel like I'm I feel like I'm unraveling a lot of generational trauma. Yeah. Uh with the way that I'm living. Like there was a lot of it, and I'm just kind of I want it to just end with me, um, which I think is a lot of pressure that I put on myself. That's a little unfair because, you know, I don't know, it took d you know, hundreds of years for this trauma to build up. It's not gonna like get destroyed in one fell swoop, but you know, I just you know, I I don't know. I just want to feel good. I'm able to look myself in the eye at all times. That's my that is my my guiding light, is just I want to be able to look myself in the eye at all times. Do you think you can now? You know what's interesting. I I feel like I should be able to, but then I just all I have are like my my my perception of people who don't like me's opinion of me. Ooh. And it really I it's like I think I need to do like EDMR or like some kind of like weird hypnosis or something because I'm so sick of other people's opinions influencing whether or not I'm going to do something or if I can feel okay about something.
SPEAKER_00And it is like it is the you know, the the evil brain not being good to me stuff that gets in there and can't seem to let go.
SPEAKER_02Well, you let me know when you figure that out, let me know because I I could use the magic formula for giving less shits about what other people think too. Um it's real hard. There is a woman, she's still she's become a friend and was a huge influence in the earliest days of building my business. And I hired her for a a one-on-one coaching. We sat in her living room on the couch, and she's like, Can I give you some feedback? And I'm like, Yeah, that's what I'm paying you for. I'm like, she's gonna tell me my website is great and like on the right track. And she's like, more than anybody I've ever met, you care what people think, what other people think. And I'm like, Huh? And she's like, I hear it in every decision you make, everything you're ruminating and everything you're chewing on is well, if I do this, what is what is that gonna mean? And I've already said it to you six times today. I have a business that doesn't make sense to other people. I'm positioning a business that works for me. I love working in, like allows me this beautiful life, and yet I position it as a thing that other people don't understand. I still do it.
SPEAKER_01It's so And it's like your job to explain it to them, and you're like Yeah.
SPEAKER_02In her philosophy was like, let them be confused. Like the ones that are curious are gonna go down the rabbit hole and they're gonna see the thing that they're looking for and they're gonna be like, hell yeah, Meg is for us. And she's not wrong. Like I trust her, and I trusted her then to just ride the wave and let it be messy and let it be confusing to people. And she's she's right. The people then that kind of rise to the top are the ones that want the story, they want the layers, they want the nuance, not the ones that are like, can you come in and 10x my sales team tonight? Like, no, I don't do that.
SPEAKER_01And if you did any research, also no one can do that. Actually, no one can do that. There's a lot of people that claim that they can do that, but no one can do that. I mean, that's the one thing when I around like speaking and podcasts and everything, when people are like, you know, what's your what's what can they walk away with by seeing you or whatever? And it's like, you know, like what kind of what kind of like, you know, edge can you give them? And I'm just like, I can give nobody an edge. All I can do is tell you that it's whatever you want to do is possible, but there's no like I feel like there's no corners that can truly be cut that's gonna make anything be as good as the thing that if you didn't cut the corners.
SPEAKER_02Does that make sense? It makes total sense. I'm I'm in the throes right now of negotiating these podcast tour sponsors. And as prudent business people, and I don't blame them, what's the ROI? They want to know that if they give me a check for X amount, that there's going to be a certain amount of progress made in their business or a certain amount of revenue. I cannot give you a number. I do not know. I will never be able to give you a number. This is an attachment to an experience, a feeling, an outcome, not necessarily a number. And some companies either get it, but they can't justify it, or they just don't get it at all. And it's not the right fit. And that's one of the things, and I think you described it really well. If that's the kind of game you're playing, we're just not the right fit. I don't believe that you can do that for the kind of things that I like. You can say that you have 5,000 five-star reviews on Google. That's great data, but you can't say that your guests are gonna have 10% more fun because they hire toast and jam. Like it just doesn't work that way. And so sometimes it's just educating the ask. Like, let's talk about this in a practical sense. Like, what do you actually want? Do you want me to guarantee you that $100 million of revenue is gonna walk in your door on Monday morning because a woman sat in an art gallery for two hours hours on Tuesday morning and paid $25 to be there? Like let's be practical about this here. And most people will kind of rewind a little bit once you explain it in those numbers. But it, you know, I'm not for everyone, you're not for everyone. And some people are looking for the quick fix. And it's usually fear and uh urgency, you know, and honestly selling to salespeople. Yeah, but like so many of the people that I'm negotiating with are they own insurance organizations. And so they are salespeople at heart in many cases, and so they're they're just least likely to open up their checkbook and want to pay for something that they can't quantifiably justify. And and so A, I have a different kind of approach when I have those conversations, but B, I put a lot less stake on them too. Like, if I had to guess how it's gonna go, it's probably a no. And if it's a no, why am I investing my time and energy?
SPEAKER_01And it's so hard. We all want to be wanted by the person that doesn't want us. Yeah. I mean, it is it is like I mean, at least I do.
SPEAKER_02I shouldn't project it on everybody, but like No, I think context matters, but yeah, to a certain degree. I mean, I certainly made most of my relationship choices um through that lens up until more recently. And in business in the beginning for sure. Now I'm I talk a lot about boundaries and it's almost an experiment. Like how how tight can I create my boundaries so that I I really am letting in only the things that serve me, the ideas, the people. And again, we talked about the bubble. It's not that, it's more from a a business standpoint that I don't want to rewrite a new keynote for every client because you know, John wants this and Mary wants that. Like, I want to talk about the things that I know are resident, resonant in put the effort in and be present, but not reinvent the wheel every time I'm doing this.
SPEAKER_01Yeah, no, I mean it's there's been decisions that have been made about how things are supposed to go. And it's like, if you're not doing it that way, it's like, well, can we just try just like can I just do it? Let me just try it. Let me just do the thing. Like, trust that I understand this enough. And if I failed at it, whatever, this wasn't a good one. But I pro I bet you it's gonna be fine. I bet you it's gonna be good. So, how can people can any so can anybody attend your lady insurance situations?
SPEAKER_02Sure. I mean, I'm knowing the the millions of women that listen to your podcast and that will hear. Millions. Sure. Yes. The tens of women that if you're gonna be in the Midwest in September, head on over to the website. I'll be in one of them for Chicago because it is home base and my roots in a sense. I'm doing Megan Friends and I'm introducing uh the women in insurance there to some women from my community that have been influential and supportive and inspirational to me. So we're gonna do a panel, and you are gonna be one of one of my dear panelists. So yeah, this girl. I'm really excited about that. That's gonna be great. So um my website, adjunctadvisors.com, is kind of central command for all the stuff that I'm working on. I'm on LinkedIn right now, definitely a little more professional, but I'm having a lot of fun on Instagram right now, talking about my my nomad travels, doing quick little sound bites, reels about life living this way and the things that come up. So all sorts of ways to to find me. I'm very Googleable, I learned.
SPEAKER_01Yeah, me too. My name is a bit less normal than yours news, but you know, I am highly Googleable.
SPEAKER_02Meg in insurance is pretty. I'm not gonna say I'm like the top hit, but I'm on the first page. So exactly.
SPEAKER_01Insurance Meg. Um, all right, Meg. Well, until next time, thank you so much. Enjoy wherever you are and wherever you're going and uh never get a mortgage again. Yay! Thanks, Mary. Bye-bye. Thanks for listening to All of the Millady Business with me, Mary Missy. Uh, we'd love for you to like, review, subscribe, follow us to All of the Millady Business on the RAM. And if you're a female identifying person and you want to dance, you can follow us. I mean, everybody can follow us, but if you want to be a part of the magic at hot watch dance party, find out where I'm gonna be hot, yeah, or anything more else. You know, money, thank you, quiet. And listen to my radio show, radio show, on trip radio, trip radio.org Monday, every Monday, on the post and five, and we get alright, guys, peace out.






