Dr. Jay Zigmont, CFP®: Welcome to Childfree Life by Design. Today we’re talking about preparing for major life changes and what it means for people who are building a Childfree life on their own terms. I’m Dr. Jay Zigmont here with Bri Conn, and in this episode, we’re covering how to financially plan for risk, how to design a powerful support system and the unique advantage of Childfree flexibility.
If you’ve ever wondered how to make a major move or career pivot without the traditional safety net, this conversation will give you the clarity and the tools to make intentional decisions that support the life you want.
Intro: From Child-Free Insights, this is Child-Free Life By Design, the go-to resource for building the child-free 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.
Dr. Jay Zigmont, CFP®: So Bri, major life events can be stressful for anyone and being Childfree means we have more money, time, and freedom usually to do things, but we also have more responsibility to intentionally design our plan. Does that make sense?
Bri Conn, CFP®: It makes a lot of sense. There is the freedom to do what we want, but also, the analysis paralysis. I can sometimes come with that too, of what the heck are we gonna do? ’cause we have so many options. Whether it be a career pivot, relocating, relationship shifts, or just retirement. Do we wanna do that as well?
Dr. Jay Zigmont, CFP®: Yeah, and it’s the hard challenge of Hey, if I could do any career anywhere, what do I do? Okay, cool. I found something I wanna do, now, how do I actually make that change?
Bri Conn, CFP®: Yeah. Taking the steps, going, okay, we’re gonna make a change. We know that we wanna find a different job and we have found what we think we wanna do, but we can’t just go ahead and quit our job tomorrow. Because we’re not preparing properly for that. So what are the things you need to consider? Is there a specific timeline for this money? Do we need different skills or education? Those are just a few of the things that we’re gonna go over and dive deeper into.
Dr. Jay Zigmont, CFP®: Alright, Bri, so let’s work a couple examples on this. Let’s start with the, hey, I wanna either change my job or take a sabbatical or go to education or do something new with my work. Where do I start?
Bri Conn, CFP®: So the first thing we’re gonna start with is figuring out, do you have debt paid off in an emergency fund? Especially if you’re gonna do a sabbatical. If you’re changing jobs, then as long as you’re continuing your income, I’m not as concerned about having all of that done because you’re gonna continue bringing income. But if you’re taking a sabbatical, we really wanna make sure we’ve got those things done. And in addition, we also have a sabbatical fund, because you don’t wanna be on sabbatical and depleting your emergency fund down to zero.
Dr. Jay Zigmont, CFP®: Yeah. And there’s a slight difference between people taking a sabbatical and taking a mini retirement. If you’re at a point in your finances where you could retire, you don’t really need the money, but you’re gonna take this mini retirement to figure out what you wanna do, where you wanna go, is different than, Hey, I’m taking a sabbatical to figure out what I wanna do next. I have to do something next.
Bri Conn, CFP®: And knowing before you make that shift, I think too, is incredibly important because, just think about, would you wanna take and go, oh, I’m gonna be done forever, and then realize, darn, I actually need to earn more. I don’t think that sounds fun.
Dr. Jay Zigmont, CFP®: Yeah, you need to have a financial plan. And part of this also, let’s be real in this world we’re in, you have to have a plan for your healthcare if nothing else. Anything can happen during that time period. Next thing I know, you’re on a sabbatical, you’re climbing some mountains somewhere and you don’t have insurance. The whole point is we’ve got more freedom, but we have to be deliberate about the way we design the plan, and the way we execute it.
Bri Conn, CFP®: Yeah, working with a financial planner can help you do this because if you’re just doing it on your own, there are so many times where we just don’t know what we don’t know. Getting professional help to create a plan to go on sabbatical is incredibly important. I have seen people who have made jumps and really not had a plan before, and now they’re coming and they’re going, yeah I made this jump, but I’m realizing maybe I shouldn’t have done it the way I did it. Being very deliberate about going, okay, I know I wanna make this change in the coming year, coming two years and saying let’s work on a plan to get there.
Dr. Jay Zigmont, CFP®: Fire prevention is a bit easier than firefighting.
Bri Conn, CFP®: Yes. That is exactly the case and why I would say talk to a professional, see exactly what needs to be done for you.
Dr. Jay Zigmont, CFP®: And let’s talk about job jumps for a second. Because in theory those should be pretty simple. I quit this job, I start there. But that’s not always the way it happens. One of the things when you look at this plan, you’ve decided, hey, I’m gonna change jobs. I wanna take a look at timing and see if it matters.
I had somebody, they were looking to change jobs and we figured out if they waited three months, they would not only get a large bonus, but they would also vest their 401k and save a lot of money. You might wanna switch tomorrow, but are you willing to give up $75,000? In this case, they weren’t. Another good example of this is healthcare. If we’re here at the end of the year, and for your healthcare at your current employer, you’re already over the deductible or out of pocket max and you’re essentially in free healthcare for the rest of the year. Maybe I wait.
The other one that happens often when you switch jobs is there’s some type of pause in between the time you’re covered on benefits from one to the other and or pay. The worst case I’ve ever seen, somebody had to go a month without a paycheck. If you can afford that, great. If not, I don’t really want you to be going into your emergency fund to bridge a month. We need to figure out what do we need to do to cover the expenses for that month.
Bri Conn, CFP®: Yeah, and you can ask people too, when you’re doing interviews, what day does everything start? How does this timeline look? Most employers are not gonna have an issue with you asking these questions. It shows that you are thoughtful. I changed jobs in the middle of the year. Benefits didn’t start for 90 days. So I just knew I had to continue my other insurance for those first 90 days until I got the new insurance. Because I wasn’t going to have any coverage otherwise.
Dr. Jay Zigmont, CFP®: Yeah, and you may have the Cobra coverage. So let’s shift from, Hey, I got a job offer to, now let’s say I’m gonna relocate. I don’t know about you, Bri, but if my wife and I are gonna move, I want to be planning this six months in advance. You don’t always know, but we started doing all the things we had to check off to move to get prepared for that because you do not wanna have to move with no planning.
Bri Conn, CFP®: No, ’cause you never know what’s gonna happen. I just did a big move here as well, and we were planning for this way in advance. In fact, to even get an appointment at the DMV in order to get our driver’s license, it was two months out. Two months before we moved, we scheduled our appointments. I love a good spreadsheet and so I had spreadsheets of everything. Registration, mail forwarding—all these different things that might come with a cost. Are you paying movers? Paying a mover is not a cheap expense.
Dr. Jay Zigmont, CFP®: Yeah, I’m getting too old to do the “friends come over for pizza and beer” move. I always plan on everything costing 50% more than whatever you got planned. There’s always something like, oh, our couch doesn’t fit and we have to get a new one. I will tell you, my first step on moving intentionally is making some Goodwill runs. And that’s not to buy stuff; it’s a one way thing. Movers charge you by the pound and by the mile. There’s some stuff that does not need to move. There’s actually a theory out there that you should move every three years anyway, just to clean up your house.
Bri Conn, CFP®: Based on how many times you asked me if I had gone to Goodwill yet, that doesn’t surprise me.
Dr. Jay Zigmont, CFP®: There’s stuff in my garage that I’ve moved three locations that I don’t think I need. We relocated, we’ve talked through some of that, but the other thing we have to do with relocation is all of that paperwork. You change states, you gotta change all your estate paperwork. I’ve looked at people’s estate paperwork and I’m like, where’s this address from? And they’re like, oh, that was three moves ago. If you’re now a resident of a new state, you need an updated will or document for that state.
Bri Conn, CFP®: Yeah, that’s something I would say is a priority when you move. That’s something you can do with Childfree Trust® too. Go ahead and say, Hey, we’ve changed states. We wanna go ahead and update our documents.
Dr. Jay Zigmont, CFP®: And remember, you gotta update your insurance and your 401k forms. If you’re doing any rollovers for 401ks, you tend to have to update your address on an old 401k for 30 to 90 days before they will make a move. It’s part of the fraud protection. And one of the ones people often miss is car property taxes. You need to notify the city you just left that you no longer live there. I moved a state and I got a bill a year later. They pretend it’s still sitting in your old driveway.
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Dr. Jay Zigmont, CFP®: All right, we talked about relocation and jobs. How about changing our relationship status? Like getting married or getting divorced. A lot of things change from a legal and financial standpoint once you cross that line.
Bri Conn, CFP®: When you’re going to get married, one big thing people forget is thinking “this is my money, this is your money.” Once you’re married, it is “your” (plural) money if you don’t have anything to protect it. When I was getting married, someone said to me: “Everybody has a prenup. It’s just, do you write yours or does the state write it for you?” That clicked for us. We wanted to write our own rules.
Dr. Jay Zigmont, CFP®: I’m a big fan of prenups. I actually prefer if you do the financial part with a financial planner. I want you to be having the conversation that the prenup triggers. “What would happen if…” “What happens to my stuff if…” I’ve done a bunch of work with couples before they get married, and I’m going to be perfectly frank, I don’t have a 100% track record of people actually getting married after that conversation. If you find out you have fundamentally different values—one’s a saver, one’s a super spender—you need to reconcile that.
I use a theory called “compatible baggage.” We all go into a marriage with baggage—work habits, crazy in-laws, political beliefs. You have to have compatible baggage. For my Childfree folks, this is the question of, “Hey, do we both agree we’re Childfree?” If you go into the marriage and try to change someone’s baggage, you are just going to be unhappy.
Bri Conn, CFP®: Exactly. And I don’t view that lower success rate as a failure. It’s a good thing because it means you’re preventing people from going into a marriage that might end up making them unhappy. I would much rather know that before I’m married.
Dr. Jay Zigmont, CFP®: Yeah, and for my clients who ask if they should get married, the first question I ask is, “Do you need healthcare?” If not, it’s really up to you. Turns out about one third of Childfree folks will never marry. The current 2026 tax code actually has more benefits for people to be single than married in some cases, like the salt tax cap being by filer. You want to be deliberate about how you’re designing your life.
Bri Conn, CFP®: I will tell you the facts and the numbers, but I will say it’s up to you to decide the rest, because I can’t answer that for you.
Dr. Jay Zigmont, CFP®: The flip side of marriage is divorce. I was just on a podcast talking about “gray divorce”—divorce over age 50 or 55. As a financial planner, I will sometimes give advice that is completely different than the legal advice they’re getting because I’m watching out for their numbers. I have a fiduciary duty to you, even if the advice makes no sense for the other person.
Bri Conn, CFP®: Having a prenup can help make a divorce easier because you’ve already written some of the rules. Divorce, no matter how it comes about, is hard.
Dr. Jay Zigmont, CFP®: From a financial standpoint, I treat this like a business that’s breaking up. We are negotiating across the table. I work with clients and say, look, from a financial standpoint, watch out for A, B, and C. Pull a credit report to make sure your spouse is off all your credit cards. Lock your credit report so an ex-spouse doesn’t take out credit in your name. Weird things happen in divorce.
Bri Conn, CFP®: Get your beneficiaries updated too! I’ve seen multiple times where ex-spouses have been listed as a beneficiary because someone forgot to update their forms 10 years ago.
Dr. Jay Zigmont, CFP®: I had a friend whose acquaintance passed young in their 30s. He didn’t update his pension beneficiary after he got remarried. The pension went to his ex-wife. Legally, there was nothing the new wife and kids could do. That happens all the time.
What we’re trying to say is that whatever move you make, you want to have a plan. We do it with a deliberate plan designed to match our life. Anytime you go through a big life transition, you shouldn’t do it alone. Build a team to help you cross the T’s and dot the I’s.
Bri Conn, CFP®: Exactly. Intentionally choosing to invest in moments of joy is just as important as investing in your future. Until next time, happy designing.
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