The Money Whisperer: Why Real Financial Independence Starts With the Conversations We Avoid

Business Insights, Free Agent Podcast, General, Women In Business

The Money Whisperer: Why Real Financial Independence Starts With the Conversations We Avoid

Most of us were raised to keep money behind closed doors. We don’t bring it up at the dinner table, we don’t compare notes with friends, and we certainly don’t admit when something has gone wrong. But that silence has a cost—one that shows up in marriages, in families, and in the choices we make about the second half of our lives. What happens when the very thing we refuse to talk about is the thing quietly deciding our future?

My special guest is Jeannie Dougherty

Jeannie Dougherty is an emotional behavioral money coach who came to this work not through Wall Street or a finance degree, but through personal loss. After both of her parents died of Alzheimer’s and her family discovered that a relative had liquidated her mother’s entire estate rather than spend it on her care, Jeannie went looking for answers that financial advisors, attorneys, and wealth managers couldn’t give her. She found them in an unexpected place—a dance workshop about money—where she met her first money coach and eventually earned her own certification. Today she helps individuals and couples understand the psychology and emotions driving their financial decisions, rewire how they talk about money, and step into self-employment and business ownership with their eyes open. Her perspective blends hard-won lived experience with a practical, no-nonsense view of what it actually takes to build something of your own.

“Money is very personal to me because I’ve watched it be used as a tool and a weapon to destroy families—and I’ve seen it help families in times of great need.”

In this episode, you will be able to:

Recognize why money stays a taboo subject in families and what that silence quietly costs you.
Start the financial conversations couples avoid before debt, credit, and cash flow force the issue.
Understand the emotional and generational forces that shape how women and men handle money differently.
Test a business idea through part-time work, pop-ups, and real conversations instead of betting everything at once.
Use AI as a tool without trusting it blindly, and surround yourself with mentors who will tell you the truth.
Reframe self-employment in retirement as a path to more freedom, more income, and more choice.

Rewiring How Couples Talk About Money

When Jeannie works with couples, she rarely starts with spreadsheets. She starts with values—because two people can love each other deeply and still hold completely opposite beliefs about risk, spending, and security. One partner tends to be the visionary who is ready to leap; the other measures every dollar and braces for what could go wrong. Left unspoken, those differences don’t just strain a budget; they strain the relationship. Too often, she explains, couples handle money with threats, power plays, and the silent treatment, so nothing ever actually gets resolved. Her twelve-week coaching program is built to change that pattern by helping partners name the emotions that surface whenever the future comes up, so a hard conversation stops feeling like a fight and starts feeling like a plan. The goal isn’t to win. It’s to give both people enough clarity and enough trust to make big decisions together—about a business, a move, retirement, even medical care—before a crisis makes the decision for them.

The resources mentioned in this episode are:

Connect with Jeannie Dougherty for a couple’s money consult to work through a major financial decision together.
Explore Jeannie’s twelve-week couples money coaching program designed to rewire money behaviors and emotional triggers.
Join Meg Schmitz’s First Friday Networking group, held virtually on the first Friday of every month, to connect with other independent business owners.
Listen to Karen Covey’s podcast, Off the Fence, for perspective on money, marriage, and difficult financial crossroads.
If you’re an independent business owner outside of a franchise, find a supportive networking community—because we’re stronger together.
Listen to the Free Agent Podcast with Meg Schmitz for real stories of self-employment and business ownership.
Contact Meg Schmitz to schedule a free, no-obligation call for insights into entrepreneurship and franchise opportunities.
Use the form on the Free Agent Podcast page if you’d like to be considered as a guest on the show.

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Click to Take the Leap into the full interview transcript of the Free Agent Podcast, Episode 8.21 with Meg Schmitz and her guest, Jeannie Dougherty

Free Agent Podcast with Meg Schmitz – Guest: Jeannie Dougherty, Emotional Behavioral Money Coach & Couples Money Coach

Meg Schmitz: Hello, everyone, and welcome to, or if you’re a repeat visitor, welcome back to… my podcast is called The Free Agent. My name is Meg Schmitz. If you are dialing in, there’s a reason why I call this free agency, Because anyone who’s self-employed has left the security of a team. You’ve gone out on your own, you took the leap, and you are a free agent. You’re looking for your posse, you’re looking for your team. The mission of my show is to share inspiring conversations with real people who took the leap into self-employment. business ownership, sometimes the conversation is about franchising as well. But everyone is looking for freedom, some type of freedom. From corporate refugees and executives tired of the desk job, to entrepreneurs and investors looking to share camaraderie and inspiration through their own business journey, my podcast aims a spotlight on real people who stepped into the unknown to control over their destiny and became their own boss.

Jeannie Dougherty: Hmm.

Meg: These conversations probably don’t come out in every… Living room, dining room, family gathering, people… people are really afraid to talk about money. And that’s why I wanted Jeannie to join me today. So, Jeannie Doherty is the money whisperer, the financial expert in my networking group. Thank you for saying yes, and welcome to the show.

Jeannie: Well, thank you so much, and Meg, it’s a true pleasure and honor to be here, thank you.

Meg: Well, the audience needs to hear what you’ve got to talk about, and, why people are… and I don’t know if it’s American, if you’ve done a study about this, people in other countries, but talk about what you do and why you do what you do, because it’s very personal to you.

Jeannie: Yeah, I never worked, on Wall Street. I don’t have a finance degree, so I’m not Little Miss Numbers, like, who walks in and goes, Meg, like, just get me inside your business and I’ll figure out your numbers for you. I mean, that is certainly one way, but it’s usually to sell you a product or a service in addition to what they’re doing. So, Yeah, I mean, so, like, tax relief, all that stuff, getting another loan, that’s typically what a lot of people do when they work with business owners. But for me, it was very personal because both of my parents passed away from Alzheimer’s, and I did have a corporate job. And it wasn’t working, even though I was even long distance, taking care of my family. And, it was just one of those things, I was like, well, how the hell am I supposed to make money and take care of myself, and still have the flexibility. Like, I wasn’t even trying to, like, make, like, millions of dollars. It’s like, can I just have the flexibility to take the time off when I need to? And, you know, it’s just hard. There wasn’t a clear answer. And so I couldn’t find anybody who really knew anything about money. Like, how do you really transition yourself? Because they’re like, well, you should have money to start a business. Well, newsflash, a lot of people bootstrap, and we have to, for a lot of other reasons. We either have expenses, or we have to work part-time, you know, in order to keep insurance, like, I could just go on and on and on. And so there isn’t always a crystal clear path, and it’s a lot of risk-taking. And… So, you know, and a lot of the times, as a woman, you’re shut down, because I heard it more than once when I first started a business. Other business owners wouldn’t talk to me if I at least was in business for at least a year. So the first year, a lot of people shunned me. And that’s where a lot of businesses go to die, and in the first 5 years, the 50% of them for sure die. So, it’s an interesting road to sign up to be like, I want to go open my own business, and I’m like, Good for you, I hope it all works out. Hopefully you have clients or customers, a contract, something, but a lot… a lot of us just start with, I have an idea and I’m going to go do this. So, money is very personal to me because I’ve watched it be used as a tool and a weapon to destroy families. And I’ve seen it also, help families in time of great need. And… Part of my story is that when my mother was very sick, my parents were divorced, they both died of Alzheimer’s, but when she died, we confirmed that another family member liquidated her entire estate, it was a million dollars, and did not spend that money on her care. And so we went to court, and we lost. There wasn’t anything we could do. The money was all gone.

Meg: Oh, no.

Jeannie: Yes. And so, when I went to financial advisors, I spoke to attorneys, I talked to bookkeepers, you know, wealth managers, people kind of know some of the red flags, but they’re not really going to do anything about it, because that might mean money out of their pocket. And so they’re just gonna kinda, okay, if this looks good enough, I’ll take it. And so, now that we do most of our banking online, it’s even faster for people to be scammed and taken out of their money. It’s no longer, like, waiting for the check in the mail, necessarily, although checks are still being written, but just using that as an expression. It’s just done so anonymously that anyone can take it. And it’s usually somebody who knows you who takes it. Not always, you know, some random person on the internet. But, it was very personal to me because it was taken out of greed. It was taken because they felt they deserved it, and they felt they didn’t owe us any explanation, even though there were plenty of benefits and plenty of cash that should have provided more care, but that was refused.

Meg: Wow.

Jeannie: So, I thought, well, I want better answers. So, I couldn’t get them.

Meg: Nope.

Jeannie: I couldn’t get them from anybody. Like, people couldn’t really answer, like, what happens in families, you know, I talked to other therapists, and they’d be like, well, I don’t know, or… you know, I have my own family, I don’t… like, a lot of people just don’t know. They don’t know enough to say, like, well, here’s something you could do to change it. Here’s something you might want to think about if it’s not going the way you think it is. And, I was taking dance classes. Because I was grieving, and I was going through litigation, and it’s really nice to kind of shut your brain off for a couple of hours a week, to not have to listen to another person tell you another story, but more importantly, you have time not to think and just be. And so it was really… it was powerful, you know, and a really good experience, and every time I share this, only women… I wouldn’t say only, but mostly women get it. Men usually just stare at me like, you took Dance classes, because you were grieving, and it’s like… Yeah. Well, I mean, you know, you probably might have a heart attack sooner than I will, but, you know, that was my plan. So, When I did that, I walked into dance class, it had been, like, 2 years, and there was a flyer on the wall about dance and money, and I went, I should go. I should go! I’m going, Meg! I’m gonna go to this dance workshop about money, and I don’t know what it’s about, but I’m gonna go. And I arrived, and I met my very first emotional behavioral money coach, which is what I later became certified as. And I finally, you know, in that first training, I finally was, like, illumination as to why families move in certain directions, why they are, like, opposing forces, why they lie like dogs, why mental illness is covered up, all kinds of things. And it was just like, oh, now I can see Why this happens? And how to avoid it in the future. So, I really didn’t have a big plan, you know, for money. I didn’t really think I was even going to become a money coach after the… after… it was like I worked with the money coach for a year. I didn’t think anything else about it, but I… at the end of it, I was like, I think I could do this, and he was like, you could. You’re really good. And I was like, okay. So, that kind of led me down to the path of going through money coaching training, and that’s when I realized I’ve been doing a lot of money coaching in my other business, and I went, oh, no wonder! So, that’s kind of, my short story of, like, you know, money got real personal real fast, and I was like, I want a better answer than the basic information you You can read on the internet. Or in this case, what AI can generate.

Meg: It’s so interesting to me right now in the season that I’m in, season 8 of my podcast, I’ve got a few more people… I’ve already interviewed a couple of other people about money, and I’ve got a couple more who are coming up, and then you popped on my calendar for today. Why do people have such a hard time talking about money and doing… Doing good things with it.

Jeannie: So, a lot of times, money, the way we learn about it is, money is sometimes, like, if you talk about… it’s like a sin in the family. Like, I mean, like, a religious thing. Like, you don’t talk about your money, whether it’s good or bad, you just don’t, because you don’t want to seem prideful, and you also don’t want to seem like a mark. Why? Because families know who the predators are. They just don’t always want to say it out loud, but they know. Yeah. But the other piece is, you know, how do you talk about money? So, if you come from a very competitive mindset, which is a lot of families, which is… you know, you must not be doing as good as me, or if you’re doing better than me, then you should be doing this, and you should be doing that, and, like, nobody really understands expenses or cash flow. That’s one of the things I notice in most families. Nobody really gets it anyway. So people have these, ideas of what money should be doing, but it’s not. So, I think, people don’t talk about it because they’re embarrassed, they’re ashamed sometimes, even for, like, no good reason. And then other times when it’s going well, like, you… who do you tell? oh, my portfolio’s doing amazing! And some people are like, are you kidding me? You have any idea what I’m trying to deal with over here? And you’re talking to me about your portfolio. And they’re like, well, I mean, I have been taking care of myself financially. And, you know, it’s like it becomes like a nasty disconnect.

Meg: Dude.

Jeannie: So, and it’s even more interesting when people are dating or choose to marry somebody. You eventually have to have that money conversation. And, that’s… I find that fascinating, because people are all over the joint, necessarily talking about cash that’s in the bank and their credit score, so…

Meg: Ugh, the number of people I am aware of who got themselves into serious financial… Straits. Because… They and the spouse did not have the conversation ahead of time about credit scores, debt load… Cash flow, paycheck.

Jeannie: Identity, identity theft, like, I’ve met more people who were dating, or unfortunately were married to somebody who basically had access to their social security and ordered credit cards in their name, and blew it up, and then just left it.

Meg: Yikes.

Jeannie: Yeah.

Meg: Okay, so getting to the root cause, this is… and I don’t… I don’t know that it’s cultural, and I don’t know that it’s sexual, even, that… But men and women do… do handle money and the money conversation differently. Why are women behind?

Jeannie: Well, you have to understand, first of all, about how money has been treated in the Western world, particularly here in America. About 50 years ago, women could finally own a bank account, and then have their own credit card, you know what I mean? So, it was always the expectation that a man would take care of us, whether it was a father, brother, uncle, or husband. And so, women were often forced to have to go to their husbands, fathers, uncles, brothers, and ask them for money. And most of the time, they were told no. So that’s not a really empowering psychic position to be in. Now, you and I both know, there are women out there that are, like, amazing at money, and many of them resist being married, or if they are married, they’re married to somebody who does not get in the way.

Because they know this one’s the money. But that’s very few and far between. Like, we’ve had women millionaires in this country, I think, like, in the early 1900s. I think this woman was in Montana, I think, and she even ran for office, you know, and it’s just… It was unheard of, but she was just somebody who had just kind of defied the stereotype. So, that’s part of it, is that we come from a place that women don’t necessarily have the financial power. But I will tell you, that men are just as confused, they are just as, knee-jerk, and they are just as, you know. They think about only one thing, you know, like, meaning they just have micro-focus instead of, like, can you look at all the options instead of just one? And men are taught that, often by default, often by their fathers. And why is that? Because they’re supposed to know, they’re supposed to be not emotional about money, and yet they’re hyper-emotional about money as much as women. If you don’t believe me, look at the President of the United States. He’s very emotional about money, and so is everyone who follows him. It’s… I’m like, oh yeah, women are too emotional. Right, here we go.

Meg: So generationally, and this is what one of the two of the other people I’ve interviewed recently, or I’ve been interviewed about, generationally now. Talking about… Alright, so I’m 63, my son is 35.

He is my financial manager. He manages my portfolio of money. I have no problem talking about it. My mother, generationally, oh, Maggie, you talk about money all the time. Like, yeah. Because… there shouldn’t be stigma around making more of it and doing good things with it, and that’s what I’m an advocate of. When… when you’re working with women who are younger now, what are some of their obstacles or hang-ups?

Jeannie: So, some of the obstacles and hang-ups are, can I afford my own place? Where should I live? Do I want to create a housing situation that I buy a home, not necessarily with a family member, but with a really good friend? And it’s not a, you know, back in the day, that would have been like, oh, you mean… You have a relationship with a roommate? No, they’re like, no, I’m just two platonic people who want to own property, who, you know, just want to own property. The other piece is crypto. Many women are doing better in crypto than men are. Hello. But that doesn’t mean the scamming hasn’t stopped. No, you still have to be really careful. It also means that more women are paying attention to investing long-term, and men aren’t. There are more women in college than men are right now, and so that’s impacting, you know, again, this power structure. Where do you want to put your money? Just so everyone knows, the trades are incredibly, you know, they are moneymakers. I mean, you do not have air or heat. The HVAC person is your godsend, and you will pay them. You will find a way to pay them. It’s the same thing with a plumber. Plumbers are often the richest trades, water in your home. You don’t have running water? Oh my god, that plumber, you will find a way to pay for it. And that’s what I mean, like, so… even if you have a trade, you could still be incredibly wealthy. Irrigation, same thing. Like, it’s just… there’s nothing wrong with it, but if we still run by very old, what I’d say, standards of, like, blue collar versus, you know, white collar, then we’re just gonna get stuck, because you know, it’s going to be entrepreneurs that are going to really lead the way in the future. People are going to be leaving corporates, because of AI, but also because they have run the, if you will, their route. Like, there’s no other place for them to go. And I’ve met more women who have just said, you know, I’m working here at this organization, I’ve worked here for, whatever, 10, 20 years, there’s nothing else for me to do. I’m not, like, they’ve already hit their glass ceiling. they could stay, you know, just kind of, you know, go into cruise control and wait, you know, maybe all their kids are out of college, and that’s not a bad decision, but more of them are leaving. And I have seen more men who are 50-ish, who are like, I’d better hang on to this job. I don’t know what’s gonna happen. And it’s like, well, okay. Nothing wrong with that, but what do you think should happen?

Meg: Yeah. So many stories going through my mind at the moment. The… the people you’re talking about are my sweet spot. Those people who are in transition, or want to be in transition. and want to take control over their financial destiny. But I do run across it, Jeannie, with… And I dedicated one of my seasons of my podcast to couples in business together. So what do you see with couples And money… couples in business together, because I remember part of what you do is to help couples reprogram the dialogue around money. talk about… tell us about that. What… what do you do to help couples in particular get more honest, real, and comfortable Talking really about a business, cash flow, profitability. How do you help.

Jeannie: So… Yeah, so what happens a lot of times when I’m working with couples, they are often… one of them wants to own a business, or they have a business opportunity that’s gonna show up. If they haven’t already opened a business. And so, they usually have no business experience, and all I can say is, welcome to the entrepreneurial club. None of us really do. We all kind of figure it out as we go along. But there can be real consequences in your marriage, and it can be real consequences to your financial future if you, oh, we thought we would have $20,000 extra by now, and you’re like, nope. no, no, no, you’re down by 10. That’s your… that’s what’s going on. So, what my experience is, is that you have somebody who’s more visionary, and their ability to take a risk is, like, sure. And then they’re often married to somebody who’s, like, constantly measuring all of the dollars, and who are, you know, risk adverse at best, and then, you know, for them to imagine, you know, getting more clients, or customers, or charging more, I mean, it’s just too foreign, and it’s extremely painful. I just had a conversation, one person wanted to open a business because they didn’t feel like getting a job. They thought it would be easier, and I’m like. Maybe not! Depends on the job, and it depends on the job.

Meg: Do a little reality check on what’s easy.

Jeannie: Yes. And so those are money values. So my biggest experience working with couples is trying to help them see what are your different money values, and where are you the same. Because if you’re diametrically opposed. then, unless you’re both, like, financially stable, then yeah, you could probably do that. Like, one person will open a business, the other person will work a job. That should work. But it usually isn’t. I mean, I think you and I both agree that most marriages, people are interdependent, financially speaking. Like, somebody’s carrying the insurance, the other person’s, you know, taking off every third Thursday in order to handle childcare. You know, so it’s… it’s not as, black and white, as financial experts, like advisors and wealth planners can explain, and it’s not as easy to realize, like, well, what do you do if it’s not working? Like, how long do you go down this road of maybe opening a business full-time until you realize it’s not going to work? Because you don’t have the skills to make it work, or you don’t have the cash to make it work, or whatever it is. And that, I find, is really the biggest problem with couples, is they don’t know how to talk about, if this isn’t going to work out, can we have an adult conversation so we are not in the red by 10,000 a month, and now we’re… we don’t know what we’re going to do.

Meg: And it happens a lot, where… Somebody’s not talking about money, because They are in the red, and the other one isn’t asking because they’re afraid to know. One of the… one of my favorite, well, she’s a podcaster, and she’s also been a guest on my show a couple of times. Karen Covey, her podcast is called Off the Fence. She’s a divorce attorney. So people are on the fence. Do I fall this way? Do I fall that way? I don’t know, I’m kind of comfortable on the fence, because I don’t have to deal with all the scary stuff. When you get off. But this topic of how money can destroy Whether it’s a marriage or a family, it’s… it’s a powerful tool for good. So, how do you help people rewire, reprogram their relationships so that they can talk productively about whether it’s good or bad.

Jeannie: Yeah.

Meg: current position, you’re in a marriage, and let’s try to keep it that way, if that’s what you want.

Jeannie: Yeah, I often think of a sports metaphor, because I would… I’m slightly tall. When I say slightly tall, I’m just a little bit above average. I’m only 5’9″, but apparently, to some people, I’m a giant, so I’m not. I’m not… no, the WNBA is not calling for me, so… but, I think about this all the time in basketball, about what we call a triple threat. Which is, you’re standing there holding the ball. You could pass it, you could dribble, or you could shoot. And so I try to give them, like, really simple ideas, like. Here’s what’s gonna happen if you pursue the course of, say, dribbling. Like, oh, I’m gonna go forward and follow my plan. Here’s what’s gonna happen when you realize you are blocked. You cannot shoot, you cannot dribble, so you’re gonna have to hand off. And what does that mean? That might mean that you’re gonna work only part-time, or you will have to figure out another way to supplement whatever expenses you have in your business, meaning you might work part-time, you might do something else. Or you might have to tell your spouse, and your spouse will help you problem-solve it. Like, that would be another example of a pass. And the last part is, do you shoot? Well, the shooting would maybe be your marketing and your sales, and it’s sort of like, how often are you able to get a sale? And that’s when I think people are like, oh… I mean, I thought it would just be like, you know, people would hear me and they’d understand it, but if you’ve been in business more than 5 minutes, you realize that you sound like everybody else, so you don’t stand out. You’re not clear enough with your own offer, let alone what it is that you can do, and you haven’t had enough coaching to help get you there. And… and then people are like, oh… Oh, because, like, people who become self-made, or millionaires, or billionaires have enormous amount of coaches that are supporting them through sales, through marketing, through money, through business deals. Like, they have got a bench like you’ve never seen. It’s, like, 20 people deep. And they trust them implicitly, because they’ve actually shown them how to do it. So, that’s what I mean, but you’ve got to be able to have a real conversation about, like, hey, here’s what your risk is if you start a business. You don’t have any money, you know, to back it up, and a credit card really isn’t backing it up, because you’re going to owe on that. And if you really want to start it, can you go work for somebody else to find out how this really… how this business might look? Have you thought of that? Have you thought about, maybe doing this part-time, or for a period of, say, no more than 3 to 6 months, because you at least have savings to cover that. And if it’s not working, or it’s kind of, you know, it could go any moment, you can still get a job. And sometimes people just look at me like, well, why? I just want to do this! And I’m like, I get it. But this isn’t just fulfilling a job description like you’ve done in corporate America, which is, you know, you go to the meetings, or some of the meetings, you write up some fabulous emails, and send off a report. Like, it’s a whole different skill set. And you often are the one who’s holding all of the roles, so you’re the visionary, you’re the marketer, you’re the salesperson, you’re the one who’s making sure you have, like, pens to write with, you know? Like, you’ve got tools. And AI is helpful. But AI, it requires you, the programmer, to give it the right prompts, and for you to be able to distinguish what is right and what isn’t. And so I think that’s a real liability for a lot of new entrepreneurs who are relying on AI, thinking it’ll give them the right answer. And the answer, it hasn’t. And part of it is because they’re not talking to enough people who are also business owners who could say, yeah, you could use that, but, I mean, what’s your network like? I mean, who do you know? Because that’s the thing. People actually make money together. They actually sell and buy each other’s products and services. They’re the ones who are willing to make an introduction for you. This is what people are willing to do for you.

Meg: We have learned, my husband is who I’m referring to a lot lately about AI, and depending on what tool you’re using, Claude or Gemini or ChatGPT, there is… a proclivity for AI to agree with the writer.

Jeannie: Yay!

Meg: know that, and so that… that piece of advice is get your AI to be… You’re… to play devil’s advocate. hey, I want to start this business, I want to do a residential cleaning concept, I live kind of far away from a city, so am I stupid? Is this a bad idea? And AI better come back and say, well, yeah, you’re not in a densely populated enough area, but if you just put it out there, then AI is going to agree with you. Okay, well, let’s put together a business plan.

Jeannie: Yeah.

Meg: So you really have… you… people, if you have not heard this, you need to hear the…

Jeannie: Yeah, so I wanted to say something about a statistic that I just… like, again, about 60% of what AI gives you is a lie, meaning it’s not true, and it’s up to you to figure out that 60%. And that becomes a major issue down the road if you don’t know when it’s lying to you.

Meg: Yes. I think about a recent situation where For book club. I put in the title of the book and the author, and it gave me the wrong… the wrong summary.

Jeannie: Hello! How hopeful!

Meg: Yeah! So, how much more information do you want than the actual title and the actual author, and now… So, it did me no good in preparing for book club that night. I’m a little under the gun on… but I think we’ve all read stories about lawyers who put together a deposition, or their documentation was off, and the judge figured out that they were plagiarizing and, you know, disbarred for that. So be really careful about your AI use.

Jeannie: Yeah. So, here’s something that I’ve worked on with couples. Some of them are really, really savvy, like, they have really good jobs in, like, AI, the AI sector. But their stuff is really about the back end, the security, and again, that’s a very helpful tool if you’re going to be using AI, but that doesn’t mean they have the right mindset to run a business. just because you’re a critical thinker does not make you a good business owner. So what hap… what are some of the money-making ways is that you have a brilliant idea, but you’re willing to talk to people, like, real people, not just sit in your basement and chat away on AI, and start, like, going, well, for instance, you know, the cleaning business. I’d love to start a residential cleaning service. And, you know, one of the first questions I would have is, like, well, did you want to do that full-time, or just on weekends? you could start on weekends only, and do it yourself, and see how you’re doing. And if you’re like, oh, no, no, I want to hire people. Okay! But you have no income coming in, so who, you know, like, do you have a loan or any… you know what I mean? Like, how would you know? And if you realize that, okay, you made good money, but then you were exhausted because you had to work every weekend, and then I’d be like, okay, you made good money, so now maybe you could hire some people. And then, you know, maybe if it goes on a little longer, you could actually hire people to run the business. And I’ve seen this happen many times at the federal government level. There are many employees who have, like, they’ve got the pension, they’ve got all that, and they’re not gonna quit, because they love what they do. They’re real subject matter experts in, like. I wouldn’t even say bureaucracy, like in science and law and policy making, so they’re necessary, if you will. But what the difference is, is that they’ll be like, I love wine and chocolate Meg. And so they’ll start a specialty business because they followed their passion. But then they decided, like, the best model they could after about 3 years of trying different things, so they were willing to, what? go through the risk of, like, let me try this and see if this would work. Oh, no, I have to keep it local. I’m not gonna be shipping chocolate all over the place. That’s not gonna work for me. Good plan. But then I’m gonna have to hire somebody who’s gonna be able to run, sort of, the local wine and chocolate shop. And when they do that, all of a sudden, the world gets so much better, and so when they’re ready to retire, they already have a business that’s thriving, and they don’t have to be there full-time. But they took the risk on what they loved, what they were doing. So it wasn’t laborious, like… I’ve met people who are good at cleaning, but no way do they want to go into other people’s homes and clean. No way. No way.

Meg: That’s a really interesting conversation that I have with people all the time about Passion versus profit?

Jeannie: Yes!

Meg: And so, what I say to people is, after understanding why we’re even having this conversation, is if you’re going to start a business, you’ve got to figure out profitability, because otherwise it’s going to suck you down. There’s something about the dollar sign on the inside of your forehead. My time is worth this. Whether it’s a real number or not, usually it’s not a number that is reality-based.

Jeannie: But take…

Meg: something that you’re passionate about, and so I’ll ask, this thing that you’re passionate about, does it nurture your soul?

Jeannie: Yes.

Meg: Does it allow you to unplug and let the pressure out? Because if it’s one of those two, then don’t do it. Because once you own it, it’s going to live in your head 24-7, and you’re never going to step away from it. Now, passionate… I’m passionate about wine. But if you don’t understand state laws, county laws. opening a taproom or opening a tasting room is what I really mean. There are a lot of ways For something that you enjoy. to be potentially rewarding, but to your point earlier, surround yourself with knowledge… knowledgeable people who can help you avoid the pitfalls. AI can’t do that unless you ask it to help you identify the pitfalls. That’s why you need to have mentors, and you need to have a network of people who will tell you the truth.

Jeannie: Exactly. And that’s why, as soon as you were talking about Tasting Room, and I was like, oh my god, Meg, think of pop-up tasting room, because this way, you can figure out locally where you can go, but you want to go to festivals and places where people would want to taste the wine, not instead of you’re just sort of like, don’t you want to come all the way in the middle of nowhere and drink wine? Well, who’s gonna drive there?

Meg: That’s right. That’s fair.

Jeannie: a big problem.

Meg: We were just in, we were in Raleigh, Durham, and, talking to some people who had driven down from Washington, D.C, and we were talking about wine country.

Jeannie: Yes.

Meg: Virginia.

Jeannie: Yes.

Meg: You’re out that way.

Jeannie: Yes! I know, I know all about it. People hire, like, buses, like, you can, like, find them on Meetup, like, you know, some of the wineries, they’re like, oh, would you like to do a wine tour? So it’s a little bit like a beer crawl, like in, you know, cities. You just get on the thing, and boy, people get ripped, roaring drunk, but they’re not driving. And that’s what it is.

Meg: And so, years ago, when I lived out there, this is… 2005, let’s say. Wine country isn’t… wasn’t then what it is now. Those people had to do what you’re talking about. They had to struggle, they had to suffer, they had to attract, they had to market, they had to hope that people would show up and not call their wine stinky, smelly, or awful, because it didn’t compare to Napa or Sonoma. Some of the better wine areas of our country. Well, now look at it. It’s a thriving… thriving… tour bus route that’s out there, and it’s… anyway, back to the whole idea of have an idea figure out how to monetize it. It’s going to take you some time before you’re an overnight success.

Jeannie: Right, which is why I said, pop-up! Try a pop-up first! Try it! And, and I’ve met more people who’ve done that in retail instead of getting signed up to brick and mortar, full-time, because they’re like, I honestly don’t think I could handle a January in retail, which is, you know, for those of us who know, it’s pretty slow, unless you’re, like, maybe in Hawaii or Florida, where, you know, more winter visitors, so more people are willing to spend, but still.

Meg: Yeah. Well, the whole subject of money, I think, is such a great topic. What are you doing? What offerings do you have for people who would be interested in following up with you about.

Jeannie: Yeah, yeah. So, how I like to work is every couple’s different, but the couples that I work with are ready because they’re ready to make a change. You know, they’re like, we’re getting closer to retirement, we’re not on the same page, and we need to figure out our money values and what we can do next. So, I offer what I call just, like, a couple’s money consult to help them make a big decision. So, sometimes it’s about education, sometimes it’s about where you’re gonna live, sometimes it’s about surgery. Because you’re both not on the same page when it comes to medical health, I kid you not. And, they just need that question answered, you know? They just, they don’t know what to do, because they don’t have enough clarity from a doctor who can’t talk to them about their finances. Sure, they’ve been sold insurance. What does that mean exactly in terms of coverage? They don’t really know. And then… because, you know, hospitals don’t know either. I don’t know. They’re just gonna give you the bill afterwards. come on. Gotta do better, right? But then, you know, the other thing that I offer is actually, like, a 12-week couples, money coaching program that allows them to rewire their behaviors, because you can talk about money, but how most couples deal with money is with threats. They power place. Silent treatment. And so, surprise, nothing really gets solved. Now, if you’re both more of the agreeable kind, which is, you know, sometimes happens, and I’m lucky, you know, when I get couples like that, and they’re just, you know, they’ve been talking about money for a while, and they just know they need to get to the bottom of it, then we just have to figure out what emotions are being triggered when we talk about the future, so that you’re able to navigate in a way that doesn’t feel painful. It’s actually sort of like, oh, well, of course that could happen, I could do that. And I’ll do this. Because money’s moving all the time on this planet, all around, all around. And it’s really up to us to create the opportunities by saying, I’m ready now, I will accept money here, I’ll accept money over here, we can do this, and we can do that. And owning a business, particularly in your retirement, it’s actually a very good plan. So I wish more people who were thinking about ending their, corporate careers would be like, I should open a small-time, you know, even if it’s just a part-time business. find out something that you could do, or something that you would like, or, as I gave the example, the wine and chocolate people from the federal government who were crazy about it, found a way to start it sooner, and then decided, oh, I’m gonna have somebody run it. I’m not gonna do this whole time, this is crazy. And then they suddenly had a profitable business, and they loved it in their retirement. I mean, I’ve met people who started a business, I kid you not, on Meetup. A hiking group. And they made, over 6 figures a year, by advertising certain hikes throughout the region.

Meg: Fun.

Jeannie: I mean, like, come on, doing what they love, without having to be like, AI’s gonna show me how to, you know, I don’t know, create a business online. I’m like, well… Which part of it is true?

Meg: That’s right. Going back to the trades and women. This is a big initiative for me in the state of Wisconsin. Trades… and you’re absolutely speaking my language. Plumbers, electricians, HVAC. This is why enfranchising these service-based businesses do so well, particularly for people who are retiring, and have… still have gas in the tank, but they don’t want… they don’t want to do the thing, they want to… they want to own the thing, get the rewards from the thing, but they don’t want to do the thing. And I totally just lost my train of thought, which is not the first time in this podcast that I’ve done that. That’s okay.

Jeannie: Yeah, it’s okay.

Meg: But women, it’s women in trades. And I love Mike Rowe and Dirty Jobs. I don’t know if he’s still.

Jeannie: Yeah, yeah, yeah, I don’t think he is, but yeah, I know what you mean.

Meg: but there’s so much money to be made, and I’m… do you see… I’m hopeful that women are feeling… are believing that they are capable and confident and more willing to go into those Trades, but a lot of women are still ending up in college.

Jeannie: Yeah, so here’s the funny thing. So this is where the internet and AI and the trades and women all combine. It’s called the internet, and having your own channel. So there are more women who are doing, construction, home improvement in their home, and they’ll say, well, I learned how to do this, and so then they start, like, renovating different parts of their home, or they’ll buy another home and renovate it. For whatever the reasons, and it’s just them walking around, like, moving, like, bores and a hammer and nailing and stuff like that, but then they show the end result. I’m not a fan of a lot of their designing, per se, but I don’t live there, so I don’t really care, you know what I mean? But that’s actually a moneymaker.

Meg: There are so many women in franchising.

Jeannie: Yes.

Meg: who are… Women in a man’s world who own… Oh my gosh. I’ve been working with a gal who bought a 100-year-old older than that home, and had to have it renovated, and could not get contractors to show up. And so she has all the skill sets. And a job that’s on a different coast, working remotely. So she’s got all morning to dedicate to her business, getting the crews together and getting them out the door is the biggest part of the… of the issue she’s found. So now here’s a woman in a man’s world who’s not doing the trade.

Jeannie: Yeah.

Meg: They are, they’re the industry expert. And so she’s keeping her job, and now she’s got a great side income that’s going to be a six-figure income, and will allow her to exit the job that she doesn’t want to keep forever.

Jeannie: Yes! Yes! Yeah, and sometimes it’s not following your passion, it’s just following where the gaps are, and then closing them for yourself.

Meg: Yes. Come on, women, get out there and do it. You can be a free agent, too.

Jeannie: Yeah.

Meg: So… So… As the money whisperer. What do you want people to take away from this? interview as maybe an action item or a mission? How do you want to impact people so that they… they put into place what they have heard you talk about today?

Jeannie: So, what I would say is that as this year continues, we’re going to see major advancements in AI, but they’re not all going to be solid or good. And what has been solid is our voyeuristic tendencies of the internet for us to watch other people and learn and build relationships, even if it’s online. But it’s really the offline piece is where I think a lot of people are missing what they need in order to run a business. And, one of the things that I work with people on is understanding your money… your own money psychology, and attracting people that have a money psychology that’s complementary to you. Because there’s nothing worse than, you know, having to be like, oh my god, this guy was supposed to, like, remodel my… Business, my brick and mortar place. And he’s… and this happened to a business owner. He took the money and went on vacation, and then… and then decided to come back three and a half weeks later, and did a pretty crappy job. I mean, it was awful. To say that this man’s business was roasted, online is putting it mildly. But, I mean, like, she had put all her money down, there wasn’t any way around this, and nobody was coming in like, let me give you another $15,000 to help you rebuild the… whatever, the walls, whatever she was doing, and she was just devastated. She’d been in business for a number of years. So I feel like, the more we realize that there’s gonna be big surprises and things we can’t see, but if you’ve got a network of people who are like, whoa. can we help you out temporarily? I think we’ve got at least some temporary shelves, or, you know, what can we do to help you so you can have this conversation? You know, like, that’s where people realize that they’re in a business community and people really care about them. Instead of, it’s me trying to go against the world, and I’m like, boy, I would change sides in a heartbeat. I just don’t want to be, like, me against the world. That does not work for me. It’s too hard.

Meg: And this is why I have the First Friday Networking group, because.

Jeannie: Excuse me.

Meg: stronger together, and we don’t have to be in competition. Even if you’re in the same lane, everybody’s going to be differentiated because, number one, our emotional upbringing, our emotional reaction to things.

Jeannie: Yeah, yeah.

Meg: We… we choose how we’re going to react, and we choose how quickly or how slowly We’re going to… implement once the thing has happened. So… come… come to the First Friday group. You’ve come once. Yes.

Jeannie: I’ll be back.

Meg: We’re meeting again, it’s always the first Friday of the month, virtually. which makes it so great, because I can see in the chat, people are connecting in the moment. I can see from their facial expressions that, connection, something is… Yes! Something is happening. And for anyone who’s an independent business owner and not part of a franchise, find yourself a group like mine. Because you’re… we’re stronger together, and then you get to run into people like Jeannie. I’ve got accountants and attorneys and other support people, but your approach is so wise to… and it made me think, Jeannie, about a conversation I had with my parents’ money manager.

Jeannie: Mmm.

Meg: just last week, at 93 and 88, they’re worried about having enough money to have a caregiver come in overnight. They have planned… my dad is 93. He’s scrimping and saving, and it’s all piled up in this… and it’s a very large pile of money now, but they worry… About something they don’t need to worry about, and yet their money manager who’s about my age, is approaching it from a fear-based point of view. So, generationally, I want people to listen to this interview, too, and realize that You don’t have to do it the way your parents did it, you don’t have to think the way that they do, and if you’re working with a money person who’s not genie, who doesn’t understand your money psychology. Then go work with Jeannie, because you need to understand the emotional component behind what’s holding you back from being really profitable.

Jeannie: Yeah, and I’m sorry your parents are so worried and so scared. That’s the whole point, is that this money person was supposed to say, you have this pot of money to go do this, now you can take this money and go do whatever else you want to do with it. Or, if it makes you feel better having a backup, great, then what else do you want to do with the rest of your money?

Meg: Right.

Jeannie: And that’s where it could go, and I’ll just say could, just because I don’t know who the person is, but I agree with you. Money’s all about this nasty competition. You’re either gonna win or you’re gonna lose, and then losers don’t have any money, and it’s like, that’s not… That’s not true. I’ve met so many people who’ve been down and out and who have made money, and even in their retirements, miracles happen. And so… That’s not true.

Meg: And again, that is the prototype person I love to work with, because they still have gas in the tank. Yes. They didn’t get the reward that they wanted from the government or for their corporate career. Well, now’s the time they can have an impact in their community. They can do the things that they really wanted to do, and do the research to find out the financial upside. That’s what we’re there to do.

Jeannie: Yeah.

Meg: That’s what you and I are here to do, and that’s the good work that we do.

Jeannie: That’s right.

Meg: Well, thank you so much for taking the time today to be with me and to talk about the hard subject, but really, let’s go make more of it! Money!

Jeannie: Or if it gives you more choice. Just more choice. And when you have more choices, you have a better way of looking at, you know, what do I want to do, and now that I have some options, it’s not like there’s only one thing you can do, and that’s you’ve got to survive under Social Security. Well, that’s not going to work anyway, so we better come up with a better plan.

Meg: Okay, go find Jeannie. If you’ve listened all the way to the end of this interview, go find Jeannie, because she’s going to help you solve your problem. Thank you again for joining me today.

Jeannie: Thank you!

Free Agent Podcast with Meg Schmitz – Guest: Jeannie Dougherty, Emotional Behavioral Money Coach & Couples Money Coach

Jeannie Dougherty: Hmm.

Jeannie: Well, thank you so much, and Meg, it’s a true pleasure and honor to be here, thank you.

Meg: Oh, no.

Meg: Wow.

Jeannie: So, I thought, well, I want better answers. So, I couldn’t get them.

Meg: Nope.

Meg: Dude.

Meg: Yikes.

Jeannie: Yeah.

Meg: Do a little reality check on what’s easy.

Jeannie: Yeah.

Meg: current position, you’re in a marriage, and let’s try to keep it that way, if that’s what you want.

Jeannie: Yay!

Jeannie: Yeah.

Meg: So you really have… you… people, if you have not heard this, you need to hear the…

Meg: Yes. I think about a recent situation where For book club. I put in the title of the book and the author, and it gave me the wrong… the wrong summary.

Jeannie: Hello! How hopeful!

Meg: That’s a really interesting conversation that I have with people all the time about Passion versus profit?

Jeannie: Yes!

Jeannie: But take…

Meg: something that you’re passionate about, and so I’ll ask, this thing that you’re passionate about, does it nurture your soul?

Jeannie: Yes.

Meg: That’s right. That’s fair.

Jeannie: a big problem.

Meg: We were just in, we were in Raleigh, Durham, and, talking to some people who had driven down from Washington, D.C, and we were talking about wine country.

Jeannie: Yes.

Meg: Virginia.

Jeannie: Yes.

Meg: You’re out that way.

Meg: Yeah. Well, the whole subject of money, I think, is such a great topic. What are you doing? What offerings do you have for people who would be interested in following up with you about.

Meg: Fun.

Jeannie: Yeah, it’s okay.

Meg: But women, it’s women in trades. And I love Mike Rowe and Dirty Jobs. I don’t know if he’s still.

Jeannie: Yeah, yeah, yeah, I don’t think he is, but yeah, I know what you mean.

Meg: There are so many women in franchising.

Jeannie: Yes.

Jeannie: Yeah.

Jeannie: Yes! Yes! Yeah, and sometimes it’s not following your passion, it’s just following where the gaps are, and then closing them for yourself.

Meg: Yes. Come on, women, get out there and do it. You can be a free agent, too.

Jeannie: Yeah.

Meg: And this is why I have the First Friday Networking group, because.

Jeannie: Excuse me.

Jeannie: Yeah, yeah.

Jeannie: I’ll be back.

Jeannie: Mmm.

Meg: Right.

Jeannie: Yeah.

Meg: That’s what you and I are here to do, and that’s the good work that we do.

Jeannie: That’s right.

Meg: Well, thank you so much for taking the time today to be with me and to talk about the hard subject, but really, let’s go make more of it! Money!

Jeannie: Thank you!

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