Alli Gage: AI is reshaping corporate America, and the next economic shift will be about replacement, not recovery. For the Childfree person over 50, that corporate shift doesn’t have to be a crisis. It can be a call to action to launch an AI-proof small business. Welcome to the Childfree Life by Design Podcast. Today, we’re talking about small business 101, what a second career might look like for you, and specifically the pros and cons of starting an AI-proof small business after the age of 50. I’m Alli Gage, here with Dr. Jay Zigmont, and in this episode, we’re covering how to leverage your Childfree flexibility in order to pivot into entrepreneurship. We’re gonna talk about why small business is a resilient career choice for our current work world, and how you can use AI to immediately become a more productive founder. If you’ve ever wondered if it’s too late to start something new, or how to turn your professional experience into a business that makes you nimble and resilient, this is the conversation that will give you the clarity and the tools to make intentional decisions to support the life you want.
Intro: From Childfree Insights, this is Childfree Life by Design, the go-to resource for building the Childfree life you want. Every episode gives you practical guidance, clear direction, and meaningful conversations to help you live intentionally and design a future on your terms. This podcast is for educational and entertainment purposes only. Please consult your advisor before implementing any ideas heard on this podcast.
Alli Gage: So let’s dive into the core question. Why start a business later in life? You’re 50, 60, maybe even older. Conventional wisdom says you should be coasting towards a defined retirement date, not launching a startup. But the reality is that late-stage pivots into entrepreneurship can be driven by usually one of four main factors. We have the traditional ones that we see, like to make more money, to make a difference in the world, or to create a lasting impact, or even simply as a hobby, something fun to keep your mind engaged. But for our audience today, we’re talking about the critical fourth motive: starting a business as necessity to future-proof your income against the wave of AI replacement. So Dr. Jay, I’m really excited to hear your thoughts on this. Let’s start by talking about what are those different considerations when you’re starting a business at 50 or 60 versus 20 or 30, and how do you see AI impacting those considerations?
Dr. Jay Zigmont, CFP®: To be transparent, I’m not sure there’s 100% future-proof anything. We don’t know what the AI world’s gonna look like. But the bonus of creating something that’s your own is you can pivot. You can go where it’s gotta go. I’ll give you an example out of my life. So we built Childfree Trust® to be people’s power of attorney and executor and trustee. All of the laws at the 50 states say that has to be a person or a company or something along those lines. And that’s gonna mean humans are gonna do it for a lot longer than AI ever be able to do it. Now, AI might be able to do it at some point, and we probably have to plan for that future. But it’s a business that is human-driven, where the human matters. The human has to make some decisions. They have value in where they’re at. And I think the bonus for our Childfree folks is you have that flexibility to play with things and see what it is that you enjoy that could actually make an impact to both you and the people around you that you can make some money on. And I’ve had all different types of stuff. And I had a conversation the other day with somebody whose job is to be a death doula. We’ve had folks on the podcast that do that. I don’t think AI’s gonna take that job. I’m just gonna call it out. Maybe, but who knows? But it’s a way to make an impact that goes beyond you and, by the way, make some money. And when you get to that second half of life, being your own boss gets you flexibility, but as I always say, I work for a crazy man, ’cause I am a bit crazy on this stuff. But it also allows you to do things the way you wanna do them. Which most cases for people that’s, “I wanna do this right. I worked in the corporate world, I saw this, that, and the other. They made these mistakes. I want to do it right.” And whatever that right means to you. And it’s always a judgment call, but if you’re doing it right for the right reasons, you can get there. So what I always ask folks is, if you’re gonna start a business, there’s two questions. The first question is, who do you wanna serve? And the second question is, how do you wanna serve them? It is that simple as where to start. But then it becomes the question of, can I actually do that? What does it take to start the business? And I think those two questions are a good place to start.
Alli Gage: I think those are two foundational pieces, right? And how do you see AI changing how we look at those two pieces?
Dr. Jay Zigmont, CFP®: When I wrote the book, and it came out years ago now, I wrote those two questions, and it wasn’t about AI. But what’s key in that question is, who do you wanna serve? How do you wanna serve? When you think about things that are serving people, that tends to be things that are more AI-resistant, let’s call it that. Because really this question about service is about going that next level, about doing things that others can’t, helping people out, whatever it may be. Where AI does help us, and it makes things more efficient, and it can help you run your business, but I’m not sure AI is serving us in the same way. It does tasks for us, but I don’t know, Alli, do you think it serves you?
Alli Gage: AI and technology in general, I think of it as how can it allow us to be more efficient and effective? And when I was thinking of that specific to AI and business, it expands the opportunity dramatically to be efficient. But that’s where I think we need to be very deliberate, or we have to be more mindful in order to actually be effective. Because having these tools may allow us to get somewhere really fast, but is it where we wanna be? Who knows, right?
Dr. Jay Zigmont, CFP®: I look at it as, in the financial planning world, AI for good or AI for evil. And I don’t mean to make it draw on that black and white of a line, but let’s talk about it as an example. And in the financial planning world, the folks that I think that are using AI for good are ones that use AI to allow more time for the humans to be human, to go talk to each other, to be there serve. AI note takers, absolutely, that’s AI for good. I don’t know there’s any value in me taking notes in a meeting and being distracted during it. The AI for evil is, how do I replace the human part? And that’s where I think what AI can do and will do is it’ll democratize some things. So over time in the financial planning world, I think using AI will make financial planning services accessible to people that otherwise couldn’t afford it, which is good. At the same point, there is a purpose and a thing around the human interface that the AI can’t do. I was working with a client yesterday, and I’m trying to figure out how to build AI that can do good behavioral coaching, life planning, all that, but it’s such an art that I’m not sure AI’s gonna get there 100%. AI that enables us to do more of what we do, like our craft, or what we do well, is awesome. AI that just replaces us, it’s probably not what people are making businesses to do.
Alli Gage: That’s a very good point. I know you’ve worked with a lot of clients who have started businesses, so what have you found or what do you see as the biggest obstacles for starting a business later in life? And what are the solutions for those that you recommend?
Dr. Jay Zigmont, CFP®: I think the first question I always ask folks is, why are you doing this? And by the way, it’s never as clean as that list. It’s like, I wanna do this because. And it might be because I want to have a legacy around this, or I wanna make an impact in this area, or I just enjoy it. All of those are gonna have different purposes and different structures. So when I work with folks, I’m gonna first ask them those two questions of who do you wanna serve and how do you wanna serve them? Then I’m gonna ask them, “All right, what’s the point?” Now, from an IRS standpoint, a business is something with a profit motive. That’s the difference between a hobby and a business. So the question is, do you have a profit motive? And the answer is yes, you have a business. The next question is, how much of a profit motive? Are you trying to, like, get rich with this? Are you trying to, like, pay your bills with this? Are you trying to break even? You might be making pottery, and you’re making pottery and you enjoy doing it and you want to break even so that you can cover your costs and maybe make a little extra so you can cover your supplies and buy something new. Awesome. That’s a business, but it’s not the same as, “Hey, I want to make a million dollars on this business,” or I want to make something that’s worth hundreds of millions of dollars and sell it.” All of those have a different purpose, and I think the challenge is to be real about it. What I tend to find when you work with clients, really their business is, “I want to own my job. I want to be a therapist. I’m gonna have my own shingle. I want to own my own thing. I want to do it my own way.” Cool. That’s really owning a job. It’s not creating a business where you have employees. You’re not creating a structure that’s gonna be something you can sell afterwards. It’s really all about you and your job, and that works fine. But what’s gonna happen is getting clarity on why you’re doing the business and how it’s gonna function and how it’s gonna impact your life is gonna be different. So if I go back to that pottery example, what I often will tell somebody, if you’re doing something with a profit motive, but not trying to make a whole lot of money on it, you set aside X amount, I don’t know, ten, twenty thousand dollars to start the business making the supplies. And then the rule is the business can’t lose money. You don’t want to start a business just to lose money. That’s called a charity. You want to figure out at least how do you have enough boundaries to do that. And what’s interesting is people go, “Well, that might be a little harder.” And it is. And if you want to do it as a charity and a giveaway, go right ahead. You want to do pro bono therapy work, awesome. That’s a charity, not a business. That doesn’t mean it has to be a nonprofit, like file with the government. But your purpose needs to match your plan.
Alli Gage: Since we’re talking about AI and small business, what are the ways that you recommend someone that decides they wanna start a small business, how can they really leverage AI to make their business more efficient and profitable from the start?
Dr. Jay Zigmont, CFP®: The way I’m looking at AI right now in business, the question I will ask my team is before we hire somebody, can AI do it, and can it do it 80% as good as a human? And if it can, we probably should use AI to do that with some guidance. And I think when you ask people that question, “Can it do it 80% as well?” They’re like, “Yeah, but it’s not doing as well as I would do it.” You’re right, but it’s saving time. So how do I use that to do the stuff I don’t really want to do? Can you use AI to help you reconcile your books and do bookkeeping? Absolutely. Can you use AI to help write content? Absolutely. But if we go to that content, 80% content might work for you, but if the point of your life is you’re an author, 80% content doesn’t work. Which environment are we in? I think as I’m looking at somebody starting a business, there’s a trend now of, hey, I’m gonna start a business, be a solopreneur, so I’m the only employee, and I’m either gonna use AI for everything or contract everything out.” And you’re seeing people do this. There was somebody recently talking about can you make a billion-dollar business just you and a bunch of AI agents? And we’re gonna see that. I’m not saying that’s what you wanna do, but if you can do it that scale, you can do it day in, day out. And the key is it’s the question, how can I be more efficient with AI? The problem is that efficiency, actually what it takes is you learning how to be more efficient. My wife, she always fights me back on this, but I’m gonna go, “Hey, I’ve got an idea, I need to go fight with AI.” And she’s like, “Why are you fighting with AI?” I’m like, “Because that’s how you get the best out of it.” I was using AI the other day. I was working on some content that I was working on, and I was like, “All right. Here’s my outline. Here’s where I wanna go. Here’s where it is. Here’s all my content library. Get me a first draft.” And the first draft it gave me was terrible, and I’m like, “No, you did not listen to me.” I said, “Follow this outline. I want it this length, this where I wanna go.” And you do have to fight with it because each time you fight with it, it’s learning, “Oh, I know what you mean now. I know how you wanna do this.” And people go, “Well, but that’s gonna take more time.” And it does upfront. But now I’ve spent a whole bunch of time arguing with this AI, and now it knows how I like to write and how I like to do first drafts. Now, mind you, AI’s not doing final drafts of anything I do, and because I’m working in this Childfree area where there’s not existing content, I’m writing up stuff that’s never existed before, so I have to give it most everything. But you know what it’s really good at? Checking my references and my formatting and my structures and all of that fun stuff that makes me more efficient, but I have to put the time in upfront to teach it how to do that. And that’s where people give up. They’re like, “Hey, I had AI do this and it sucked.” The reality check is any time you ask AI for something the first time, it’s not gonna be the level you want. It’s about how do you keep working it. The goal for us as business owners is we have a responsibility to learn every single day how to get better. So that is going in with that AI that you’re like, “It couldn’t do this.” You wait a couple months, a new model comes out and you’re like, “All right. Let me try this again,” or, “Let me use an agent,” or, “Let me do something to automate.” And you have to have a barrier of, these are the critical things I won’t let it do. So like right now, AI, I won’t let it talk to clients. And I think that’s gonna be the case for my clients for a long time, if not forever. But I will let it do a lot of the analysis on the back end. I had a client that had some unique situation, and I’m like, give me five ideas of how to handle this. And it gave me five, and two of them I had already thought of. Two of them were dumb. I’m like, “Nope. AI, you missed this.” And then one I was like, that might work.” And that’s where you’ve gotta get to.
Alli Gage: To your point, Jay, I loved how you talked about the fighting with the AI. It’s obviously not to the same extent, but similar to the idea that you’re training a new employee, right? You want this AI feature to be able to do things on its own, you need to spend that time up front. So can you share how long did it take you to get it trained up to the point where now you can get better first drafts out of it?
Dr. Jay Zigmont, CFP®: If you think about content, we’ll just use that as an example. The first article or whatever I have it write, it’s not saving me any time. It’s actually probably gonna cost me time on that first one. The second time I use it, it’s now cut my time in three-quarters or half. And what happens is if you think about, all right, I’m putting that time into training it as an employee. Let’s use that example. I do like this idea of using AI agents as employees and working it through. All of that time you invest upfront is to save in the future. So I’m okay if it costs me for the first time I do it double the time. Essentially the way you think about it is if there’s something you’re going to do more than two to three times, you train an AI to do it. If it’s something you’re gonna do, like, weekly, you spend a lot of time training the AI to do it right. For example, for our financial planning, AI does a set of notes for our CRM. It also sends a draft for an email to send to clients. Every time it does that, we have to give it like, “No, you missed this. You messed that up.” And it’s a concept program. But here’s the thing. We write notes after every single meeting, and we send emails after every single meeting. So if it takes me 40 hours to get the AI to write it the way I want, now it’s saving me an hour or two of work every day for the rest of my career. That’s the way to think about it.
Alli Gage: Thank you. That really puts it into the right frame, ’cause I think a lot of people hit that first roadblock, get frustrated with the first piece, like you said, that’s never gonna be exactly as you want it, and don’t take the time to really train it so that you can use it. To that point, what are the biggest mistakes you see people when they use AI in a business or a startup?
Dr. Jay Zigmont, CFP®: I think the mistakes, I see a couple different things. One, gotta have a line between personal and professional. We’re not gonna mix our usage of technology, our bank accounts, anything like that between personal and professional. If you’re training AI to be your workplace, be your workplace. If you wanna go have a personal conversation with AI and ask it all your medical questions, you want a separate instance, a separate world. You don’t wanna be mixing those things. Same with your finances, same with everything else. You need to figure out what is business and what is personal and find a barrier between that. I actually use AI extensively on a business standpoint. On a personal standpoint, I use it to research some stuff for me, but I don’t really use it as much. And that’s because if I’m gonna book a trip for me and my wife, yes, I can use it, and I have to give a list of top places to go, and actually AI’s really nice now, I had to look at a hotel, and I’m like, “Look at these weeks and see which places have these type of rooms available.” That’s great for research, but because it’s a personal thing and I wanna make sure it’s the right thing for me and my wife, I don’t let AI make the final decisions or actually do that work. On the flip side, I’m actually okay if AI’s scheduling my work trips because that’s just me, and if it makes a mistake, I can do that. So it’s like this barrier between personal and professional that becomes important.
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Alli Gage: That’s a very good piece. I had never considered that before actually. So you also had mentioned that indispensable skill of learning neuroplasticity. I’m just gonna let our listeners know that if they haven’t already watched Dr. Jay’s episode that came out about three or four weeks ago now on AI in the workplace, he talks a little bit about how learning is such an important and indispensable skill, learning, relearning, all of that. How does it apply to entrepreneurship and starting a business, especially later in life?
Dr. Jay Zigmont, CFP®: If I go to the medical world, there’s a great example, and they look at medical professionals, and if you’re a specialist where you’re seeing new cases every day, you continue to learn every day. If you’re a generalist and you see the same thing every day, you stop learning. One of the bonuses of owning your own business is if you’re doing this well and you are really good at one thing, you’re gonna get to keep getting better and better at that, and you’re gonna have a challenge. And running a business is gonna come with its own set of challenges you wouldn’t normally think about. Oh, I gotta file with the state for my LLC or something. You would not do if you didn’t have a business. And that sounds like something you don’t wanna do, but it requires you to learn. It requires you to be working through your brain of, oh, how do I do this? For example, a lot of folks will start a business ’cause they’re good at being a therapist, but the first problem of having a business is, “How do I get clients?” That’s a marketing question. You may have never done that in your life. You may need to work with specialists on that, work with consultants. You may ask AI. But the bonus is that business is forcing you to learn. It’s forcing you to figure out how to use AI. It’s forcing you to figure out better ways to serve people. And if you’re doing that right, you are building your brain, and actually you will keep your brain for longer. There’s actually some research around this of if you sit in front of a TV and just watch TV day in, day out, 1% of your brain matter is dying off each year. I don’t know about you, but I don’t have that much to lose, so I want it to keep growing. And by having a business, you get to do that. I also love when people have a business, they get to go to conferences about that business or go try things or be part of communities, which is always a benefit.
Alli Gage: I think there’s definitely benefits, like you said, both mentally and physically. There’s a gentleman that has a brick-and-mortar business just down on the main street here in Paris from me, and he has to be late 70s. But he opens, closes every day, physically fit, and I can see how that really benefits him by keeping him going both on the mindset side and the physical side, which is really cool to see. And I think the AI conversation in all of this piece, to me, one of the places I see it taking us is that mix of what you were saying, like the craft, what do we love, what are we good at, versus the need, how, who are we gonna serve? And I would love to know your thoughts on this, how does AI inform the decisions for learning? I see it adjusting because the need changes as the foundations of how we do business and how we interact and all of that change. Do you see that change that is AI that informs the need side of it and what we will keep learning and how we learn? Or how do we attack that learning piece that you were just talking about?
Dr. Jay Zigmont, CFP®: As adults, we learn by experience. We learn by doing. We learn by trial and error. This worked, this didn’t. That’s the whole point with AI. When I talk about fighting with it, that’s what I’m doing. I’m trial and error. And I do yell at it. I mean, I’m not one of those that’s like, “Thank you very much, AI.” No, I’m like, “You’re stupid, you messed this up.” And they’re like, “No, you’re stupid because you didn’t ask me the right question.” If you saw my prompts to the AI, you might see some of that. But what it is, is it’s requiring me to put words around stuff that I have not had to put words around. Where I’m like, “Oh, I’m trying to solve this problem. AI, solve it.” AI’s like, “What problem?” You have to be able to explain the problem in complete detail. Being able to explain that, using that part of the brain and going, “I don’t know, just do it.” Well, no, I have to actually make a conscious effort to explain it. And if I have the right experiences, I keep stressing different areas of my brain and I’m like, “I don’t know what this is. Help me understand.” Now, my team, if I send them my AI outputs, they don’t like it because I always ask the AI to give me almost like a literature review, it’s a giant report on everything. Because when I learn something, I want to learn everything about it. So if I’m asking a question about this marketing thing, it’s gonna give a strategy, but I’m gonna ask it, “All right, help me understand why.” Now, I do that because that’s the way I learn. My staff then knows, scroll to page six and the answer’s on the bottom. And that’s a balancing act. You have to figure out what you want to learn about versus not, and the trap you have to be careful not to fall into is to let AI just give the answer without you doing the learning. You want to understand what the logic was behind it rather than just saying, “Oh, I trust AI.”
Alli Gage: I think that’s a big piece. We don’t wanna outsource our thinking to AI. Like you were saying at the beginning, how can we leverage it to actually get us to a higher point? And if you can get that knowledge of understanding, “Hey, here’s the strategy, and here’s all the whys behind it,” in such a condensed way, even though it may be 100 pages of condensed but as opposed to thousands, right? So I think that’s genius in how we use it versus outsourcing our thinking. Because that’s something that I found interesting. I’ve heard a lot of negative reports coming up about when we do outsource the thinking part. It’s like a muscle that we stop having. Have you heard about this at all with AI?
Dr. Jay Zigmont, CFP®: There is, but here’s the thing, if you’re running your own business and you’re doing this right, you’re using it as a thinking partner, not as a replacement. There’s some good work right now on this looking in school systems, kids are starting to not know how to write an essay because they’d ask AI to write an essay. No, that’s not the point. The point is to go and put some words on paper and figure out how to do this. When I’m asking AI to write content and help me on it, I know how to write content. I’m not asking it to do something I can’t do. Or I’m asking it to put in APA formatting. I know how to do that by hand, and I’ve actually given people feedback. It’s a nightmare. It’s a pain in the butt, but I know how to do it. Now what I’m doing is I’m using AI once I know. If you, on the other hand, use AI to just make all the decisions, if you’re doing that as your business, then your clients might as well just use the AI to do that. Why do they need you to be in the middle?
Alli Gage: Very good point. So Jay, when you work with your clients and someone is 50, 60, and they’re thinking of starting a business, what are the pros and cons that you go through with them at that age, and for someone specifically that’s Childfree?
Dr. Jay Zigmont, CFP®: My question is, why? Why are you doing this, and how does it impact your life? So I’m always gonna ask what your life is first, and then figure it on the way back. For example, I was working with somebody that loves to travel. I’m like, “Great. How do you put travel plus your work together?” And they’re like, “Well, I have to have this business ’cause I’ve already worked on this business idea. I have a business plan. I have all this other stuff.” And I’m like, “Yeah, but it’s getting in the way of the life you wanna live.” “But I have this business.” And I’m like, “I understand. The question is, how do you structure that business so that it matches your life?” Since you’re running your own business, maybe you work two weeks out of the month on your business and you travel the other two weeks. It’s about that balance between the two because the unfortunate thing is when you’re running a business, at least if I’m running a business, I always wanna be the best at it. I wake up every day, I put more hours into what we’re building at Childfree Trust®, Childfree World, Childfree Insight. I’m spending 80 hours a week on this. Now, that’s not allowing me a lot of time to travel, and the travel I am doing is to random conferences and going to Des Moines for something or whatever. Not places you wanna travel to. But I’m doing that for a purpose for a period of time. And that’s the hard part, is to make sure it matches what you want out of life and not just you feel like you’re bored and you need to do something.
Alli Gage: I think that’s the biggest key, and I’ve heard this so many times throughout the years is, once again, what is that vision? Where do you wanna be? And then build back from that so that you’re not just creating another job. Because there are a lot of people who start a business, and nothing wrong with that. “I love what I do. I just don’t wanna do it for somebody else.” But is that going to get you to that end goal? And I think a lot of times people end up down that road and then realize that it didn’t give them maybe the time, freedom or flexibility and location freedom that they had or really wanted truly deep down if they had taken that time to really take the step back. So I think what I’m hearing for you is really the first step is really to understand those first questions about your amazing life, who you wanna serve, how you wanna serve them, and why. And then you can really build from there using AI as your booster. Does that capture it?
Dr. Jay Zigmont, CFP®: It is, but it’s also about setting boundaries. What are the limits? And I’ll give you an example out of my life. So, I run both Childfree Trust® and Childfree Wealth®, and I have some clients still at Childfree Wealth®, but I’ve limited the number of clients. I’ve also limited the days that I meet with clients. I usually meet with clients on Mondays. So I sent all my clients an email and said, “Hey FYI, the only day I’m gonna have available for clients is Mondays. If that doesn’t work for your schedule, please let me know. I’ll find you another planner on our team. But you can schedule a year out in advance on Mondays.” I sent that email at 8:30. By 9:00 AM, my email was full of appointments for the rest of the year for all my clients, ’cause they know, oh, I provide a certain service. This is how it works. These are the rules. And there was not a complaint at all. As a business owner, I have to bend over backwards for my clients.” Yeah, but you also have to set good boundaries. So what I said to them was, “Yes, I want to serve you. This is how it works. If that doesn’t work for you, please let me know.” And everybody found a way to make it work. And that’s the hard part. As an owner of a business, you feel like, “I’m gonna lose clients. I’m gonna do whatever if I set boundaries.” But it is the most important question.
Alli Gage: That’s a great piece, because I think we can end up, like you said, in many situations that wasn’t what you plan to create for yourself if we don’t have those boundaries. And to your point of sometimes we have to fire clients, not necessarily in every industry or every type of situation, but sometimes we worry that creating boundaries, no matter what it is, it can create that barrier. Am I gonna lose more clients? Will this negatively impact the business in some way? Have you ever found that creating a boundary had made a negative impact in the business?
Dr. Jay Zigmont, CFP®: One of my colleagues gave me this and genuinely I stole this. He said: Look, there are A, B, and C clients. A clients are the ones you would work with no matter what, whether you got paid or not, but you could get paid. B clients are the run-of-the-mill, they’re fine. They pay their bills. There’s no problems. C clients are the ones you take if you’re broke and you need the money. You don’t really wanna work with them, but you need the money. And my argument is if you’re gonna start one of these businesses, you’re trying to make it fit your life, is you really are only gonna work with A and B clients. And that may mean firing some C clients or making it hard for them to work with you. And by the way, over time, ideally, you’re only working with A clients. You’re only working with the people that bring you joy by serving them. And if that’s the case, you’re getting paid to enjoy what you’re doing. You’re getting paid to play baseball. That’s the ideal structure. Now everybody goes, “I might lose them.” If anybody comes to me with a business and they’re already running it, my first answer is double your pricing or raise it by 50% at least. And people are like, “But if I do, clients will disappear.” So I did this with somebody who’s had a dog walking business, and I said, “Double your price.” They wouldn’t do it. They went up by 50%. And they were worried clients would leave. I’m like, “So if some clients leave, the amount of people that are paying you more will actually make up for it.” Here’s the fun part. They raised their price by 50%. They have more clients than they had before because people are like, “Oh, obviously it’s a better service. This is more exclusive.” And it’s that psychology that you’re like, “I don’t understand this.” And they’ve raised their prices again, and still clients are bashing down their walls where they have a waiting list. And I’m like, “This is the head trash we have.” Oh, client’s gonna leave. I gotta do this and the other.” If you’re providing a good service at a reasonable price, you get crazy and eventually won’t afford it, you can get there. One of my colleagues he’s a fitness trainer, and he hated doing one-on-one coaching. He only wanted to do group coaching. So he started doubling his hourly price, and he just kept doubling and doubling and doubling it. And what he found was every time he doubled it, he got more clients. Now, his rate is something over $1,500, $2,000 an hour. And all he does is he works with athletes like, football folks or whatever that can afford $1,000 or $2,000 an hour. And what he said was, “Hey, if I’m getting paid $1,500 an hour, I like doing the one-on-one coaching.” All of a sudden these B clients became A clients ’cause I’m getting paid that much. And it’s just these things that are stuck in our way, and if the answer is you’re running a business, you’re like, “I don’t like this type of client,” or, “I don’t like this type of work,” price it until you do like it or get rid of it.
Alli Gage: I love that. So Jay, say our listeners, they’re Childfree, they’re over 50, they’ve thought about what they want their life to look like, they’ve thought about the type of business they want, who they wanna serve and how, what are some of the biggest things that demographic really needs to consider beyond that? Are there any risks or things that are different considerations in somebody at maybe 20 or 30 when it comes to potentially medical, physical health stuff? What things should we consider?
Dr. Jay Zigmont, CFP®: It’s more about you’ve gotta make sure the business doesn’t have a negative impact on you. So that could be financially, that could be emotionally, that could be physically, whatever else it is. It’s gotta be something that adds. Now let’s be real, whenever you start a business, the first six to 12 months probably is not gonna be great, and you’re probably gonna lose some money, and it is what it is. But you have to set limits. The bonus of running a business is now actually you can write off some of your health insurance as part of that business expenses. You might be able to write off some of the expenses you have for your computers and your internet and other things, where it starts benefiting you. But the same time, you need to build enough of a limit of, at this point I put too much in and I gotta call it a day. You don’t wanna give up your future for a business that’s dying. We see this a lot with restaurants. Restaurants are a terrible business. People love doing them. They’re very social. There’s a lot of good things. But making money at a restaurant is really hard. It just is. And people will put their entire life savings into this restaurant hoping something turns around, and too many times it doesn’t. It’s just high upfront cost. Everything costs more now. If you’re serving meat in the US, the prices for all meat have gone up so high that you can’t price it that a client will pay for it. But your heart is in it. And I’m like, “Yes, I understand your heart is in it. I have to acknowledge that. At the same point, that business is now hurting you.” The bottom line is the business has to help you, not hurt you.
Alli Gage: Jay, before we get into our deliberate details, are there any other takeaways or thoughts that you want to make sure our listeners know about when it comes to starting a business over 50?
Dr. Jay Zigmont, CFP®: I think the one thing is you might have watched a bit too much Shark Tank or other things where entrepreneurship is seen as this glamorous thing. I’m gonna tell you the reality is it’s not. How do I make payroll every week is a big thing if you hire two people. You have to be realistic about it. And, it’s okay if you try start a business and then you’re like, “This sucks and I don’t wanna do it,” then get rid of it. It’s okay to try things and be like, “I always wanted to.” Great, do it. But be okay to say, “You know what? This is not adding joy.” I’m not saying give up just to give up. I mean, if I gave up every time I ran into a wall, I would’ve given up on my business 100 times over. But you need to be real with yourself of, is this going in the right direction? Am I doing the right thing? Is it bringing me joy or not?
Alli Gage: Great words to leave us with. So we’ve reached our final segment. As you guys are aware, it’s called Deliberate Detail, and this is where we share small, intentional things that we’re doing to design an amazing life. We share what it is, why it matters, and what it costs. So Jay, what’s your deliberate detail that you wanted to share with us?
Dr. Jay Zigmont, CFP®: Right now, my playground is playing with AI agents and seeing what they can do. It does cost some money. I had to buy a new computer that does it and I’ve gotta find some time for it. But I’m playing with it. I want it to call and make my appointments at the dentist. I’ll start there. We’ll see if it works. This is one of those, I think I’m gonna be yelling at it more than expects. But that’s my playground.
Alli Gage: As long as your playground doesn’t end up in unnecessary root canal, we’ll be happy. That’s awesome. And I’m excited to share this week too. It’s something that I’ve been thinking about, and I may have even mentioned at one point in time on a different episode. But next week I’m starting to get a meal delivery service, which this may not be for everybody, but the meals are actually prepared fresh by what they call a chef every week. So I’m really excited for this. Just allows me to really dive into all my passion projects and the work stuff, and not have to take the time to think about meals and all of these kinds of things. So I’m really excited for that, and for people to know that the cost is actually not that bad. I’m in Canada, so the full price the meals are about 13 to 13.50 per meal, which is like maybe $10 at this point in time with the exchange rate. And so definitely not the same as eating at home obviously, but way better than eating out, and health-wise it’ll be way better than eating out. So I’m really, really excited. I didn’t order it in time for them to start this week, so they’re starting next week, but that’s my deliberate detail that I think is gonna make a difference in not having to stress about what to eat and make it every day. So that’s a wrap on Small Business 101. Remember that in a world that’s being reshaped by AI, corporate changes is really your chance to stop building someone else’s dream and start designing your own AI-proof life. And if you enjoyed this episode, hit follow, leave a review so more Childfree people can find the show. And if you’re interested in diving further into your amazing Childfree life, you can find all the resources you need at Childfreeinsights.com. Until next time, keep designing on your own terms.
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