Is It Time for Us to Get a CFP?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger

Episode Title: Is It Time for Us to Get a CFP?
Date: October 14, 2025
Guest: Chris from New Hampshire
Theme: Navigating Retirement Decisions with a CFP

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Episode Overview

This episode centers on a listener, Chris, who seeks reassurance and expert guidance about whether he and his wife are truly ready to retire, and how working with a Certified Financial Planner (CFP) can help. Chris describes his journey into, out of, and possibly back into retirement. Jill analyzes Chris’s financial situation, discusses risks and strategies for drawing down assets, and explores the value a CFP brings to complex retirement planning.

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Key Discussion Points & Insights

1. Listener Background & Current Situation ([02:31]–[07:17])

• Chris and wife (both nearly 60) have been saving and investing, and Chris recently hired a CFP at Fidelity.
• Chris’s wife is retired; he partially retired but went back to work “out of boredom” and misses true retirement.
• Chris earns between $225,000 and $250,000 annually.
• Primary questions: Did they make the right decision to get a CFP, and can Chris retire confidently considering market uncertainty, healthcare costs, potential government shutdowns, and timing of Social Security?

2. Complete Financial Picture ([04:27]–[07:17])

• Assets:
  • 401(k): $410,000
  • Rollover IRA: $1.775M
  • Roth IRA: $104,000
  • Wife’s IRA (from 403(b)): $561,000
  • Brokerage account: $750,000 (including $370,000 in high-yield savings and $380,000 in stocks)
  • Bank savings: $40,000
  • HSA: $6,000
  • House (fully paid): Estimated $1.3M
  • No other properties after recently selling a vacation/rental home
  • Potential inheritance: Estimated at $1.5M–$2M in 8–10 years (using $1M as a conservative figure)
• Spending:
  • Baseline monthly: $13,000–$13,500
  • Anticipated bump to $15,000/month (mainly pre-Medicare due to healthcare costs, home renovations complete, $50,000 earmarked for an upcoming wedding)

3. Retirement Income Planning, Social Security, & Asset Drawdown ([08:55]–[13:52])

• Chris and wife have not yet drawn Social Security; plan is both to wait until age 70 for maximum benefits:
  • At 67: Joint $5,884/month
  • At 70: Joint $7,300/month
• Jill recommends exploring “substantially equal withdrawals” or an annuity to bridge the gap between retirement and Social Security at age 70.
• Importance of considering the “tax bomb” lurking in large pre-tax accounts.
• Jill encourages running scenarios: If Chris and his wife spent aggressively from their pre-tax accounts, factoring in inheritance and home equity, would they still have enough in the long run?
• Jill notes they're not banking on inheritance but acknowledges it as a meaningful possible cushion.

Memorable moment:
Chris: “It sounds much better when you say it.”
Jill: “You’re doing right, you’re doing great.” ([13:14]–[13:18])

4. The Emotional Side of Retirement Planning ([13:14]–[15:55])

• Chris admits to being “addicted” to monitoring investments daily, which drove the decision to bring in a CFP.
• Jill applauds Chris’s self-awareness and discipline, reiterating that getting help to navigate distributions and tax strategy is wise after years of successful DIY investing.

Quote:
Chris: “I don’t know how to take the money out. I don’t know, you know, all those decisions that would drive me crazy. So I need a professional to do that.” ([13:38]–[13:52])

5. Stress Testing the Plan: Risk and “What Could Go Wrong?” ([13:52]–[16:55])

• Jill’s main suggestion: Ask the CFP, “What could blow up this plan if I retire now? How do we guard against that?”
• Encourages the use of scenario planning, especially considering a potential market downturn or major unexpected expenses.

Quote:
Jill: “What am I guarding against? What am I not seeing? Tell me how this plan implodes.” ([15:52]–[15:54])

6. Healthcare Cost Concerns Before Medicare ([15:59]–[16:55])

• Chris worries about rising healthcare costs pre-Medicare.
• Jill reassures him their plan can absorb premiums up to $1,500/month for two people, and notes many retirees work part-time for benefits if desired.

Quote:
Jill: “If you got really bored again, you could go work and do something equally as boring and get coverage.” ([16:12]–[16:17])

7. Portfolio Allocation: 60/40 vs 70/30 ([17:41]–[19:21])

• Chris’s portfolio was 60/40 stocks to bonds; Fidelity is suggesting 70/30.
• Jill: “Are you willing to forego upside to protect more of your downside?” She encourages Chris to have the advisor show scenarios for each allocation, highlighting there’s no single right answer—comfort and risk tolerance matter most.

Quote:
Jill: “It’s not like right or wrong; it’s how you feel. That’s one of the few feeling questions that we have.” ([19:20]–[19:21])

8. Wrapping Up: Action Steps & Mindset

• Jill encourages Chris to let the CFP prepare scenarios, revisit after the meeting, and not underestimate the emotional relief from having expert guidance.
• She reminds Chris that, with a paid-off house, assets, upcoming inheritance, and no dependents, “You are okay.” ([16:55])
• Jill’s final advice: Ask tough questions of the planner, trust their analysis, and remember to evaluate how much risk and flexibility is tolerable.

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Notable Quotes & Timestamps

• Chris: “Did we make the right move in our situation? … Am I good to stop working? My confidence is not there.” ([02:50]–[03:29])
• Jill: “You have a lot of money because of this, this rollover obviously, and the 401k … this is all your pre-tax money, right? Hasn’t been taxed yet.” ([08:32]–[08:58])
• Jill: “You’ve done a really good job managing this … Without the inheritance, I would tell you to keep working, by the way, I really would.” ([13:52]–[14:02])
• Jill: “My number one question for the advisor would be like, ‘Tell me what the scenario looks like if I retire at the end of this year.’ … And what blows this plan up?” ([15:55])
• Jill: “It’s not like right or wrong; it’s how you feel. That’s one of the few feeling questions that we have.” ([19:20])

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Important Segment Timestamps

• Listener call-in begins: [02:31]
• Assets walkthrough: [04:27]–[07:17]
• Retirement income drawdown strategy: [08:55]–[13:52]
• Emotional realities of financial planning: [13:14]–[15:55]
• Healthcare cost discussion: [15:59]–[16:55]
• Portfolio allocation decision (60/40 vs 70/30): [17:41]–[19:21]
• Final wrap and action steps: [19:21]–[19:47]

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Tone & Style

Friendly, direct, and reassuring. Jill Schlesinger keeps the conversation jargon-free, empathetic, and practical, putting financial decision-making in real-world terms and emphasizing emotional comfort as much as mathematical precision.

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Takeaways for Listeners

• Getting a CFP is about not just math but peace of mind and guidance on drawdown strategies, taxes, and risk.
• Stress-test your plan with your advisor: Ask what can go wrong, and be honest about your risk tolerance.
• Healthcare, market downturns, and other variables should be built into your scenario planning.
• Emotional relief from delegation and expert input can be as valuable as investment returns for retirees.

Chris’s story is a relatable example for anyone on the cusp of retirement, wondering if it’s finally “okay” to stop working, and how to approach that new chapter with confidence and clarity.

Transcript

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[Chris]

First of all, thank you so much for taking my call. I feel like I'm talking to a couple of rock stars because I absolutely love your show.

[Jim]

Oh, you're very sweet. We're just regular people. Don't worry, Chris. Just you and me talking with the millions of others, maybe thousands, a lot.

[Chris]

Of people, and hopefully you can sort of help me out today too. So I appreciate it.

[Jim]

Fantastic. What's up?

[Chris]

Well, I first reached out to you guys, wondering if it was time for us to get a financial planner and if it made sense. And in that time frame, in the last couple weeks, we actually did go ahead and get one. Okay. So my first question I would be, I guess would be, once we go through things, did we make the right move in our situation? I feel. I feel good about it, but I'd love to hear your thoughts on that. And then the other big question is, you know, am I good to stop working? My confidence is not there. Just with everything going on in the world right now, and we're gonna need health care. The price of that and government shutdown and Social Security.

[Jim]

It's so much. It's too much. It really is. So, Chris, how old are you?

[Chris]

I'll be 59 next year, and my wife is 60.

[Jim]

Okay, next year.

[Chris]

I'm sorry, Next month.

[Jim]

Oh, next month. Okay. So I'm just gonna say you're both 60. Let's do that. And are you both working full time?

[Chris]

No, my wife is retired. She retired a number of years ago, and I am still working. I actually took a pseudo retirement about three years ago and then found out all my friends were still working, so I decided I had an opportunity to go back. So I'm working again, but I'm very bored and want to stop.

[Jim]

Wait a minute. It's like I have nobody to play with. You should have gotten some older friends is what you should have done.

[Chris]

Yeah, so it was a little embarrassing, actually, but.

[Jim]

Oh, did you go back to the same place?

[Chris]

No, no, no. I had some friends who I used to work with who called me out of the blue and said, we have this opportunity. Is this something that would interest you? And I said, you know what? Right now it does. And so I jumped on board, and here I am.

[Jim]

All right, how much are you earning right now?

[Chris]

Between 225 and 250.

[Jim]

Okay. And let's go through what you guys have saved and determine whether or not you really can do retirement for real this time. So you said your wife is retired. Does she have a pension or is she retired and have just retirement accounts?

[Chris]

Just a retirement account. She was a teacher, but she worked part time.

[Jim]

Okay.

[Chris]

Yeah.

[Jim]

So what have you guys amassed in terms of your assets? Let's go through and do retirement first.

[Chris]

Okay, so 401k. I have 410 okay, we have a rollover IRA of 1.775.

[Jim]

Oh, that's the old job. I got it.

[Chris]

Correct. Yes.

[Jim]

Okay. Got it. Okay.

[Chris]

A Roth of 104.

[Jim]

Okay.

[Chris]

My wife, her 403B just rolled over to an IRA. That's 561.

[Jim]

Okay, that's good.

[Chris]

Very good. And then we have a brokerage of 750. So that's 370 is in a high yield savings, and 380 is in a bunch of miscellaneous stocks now that we've moved over to our cfp, who moved everything around a little bit.

[Jim]

Okay, got it. But half of savings, which is good. And beyond that, brokerage savings. That three. Something. Do you have other money that's in the bank? Boring CDs, something.

[Chris]

See. Checking and savings, 40,000. HSA 6000.

[Jim]

How about the amount of money that you spend?

[Chris]

So it's been a tough one because we moved into a new house a couple years ago, so there's been tons of renovations. I've been trying to figure it all out. Somewhere around 13 to 13 and a half, I would say.

[Jim]

Okay.

[Chris]

And that's one of my concerns is because we'll need health insurance. And so when I do my numbers in my head, I'm like, okay, we're probably more around 15 for the next six years or so.

[Jim]

Right. All right, well, let's see how this works out. Tell me about the house. How much did this house cost, you know, or what's it worth?

[Chris]

Right now it's worth about $1,300,000.

[Jim]

And do you have a mortgage?

[Chris]

We do not.

[Jim]

This is good. And is there anything else in your financial life that we should know about? Do you have a vacation home or rental property or anything like that?

[Chris]

Well, we had a vacation home slash rental property, actually. I reached out to you guys last year, but we ended up. We didn't touch base, which was fine. We ended up selling it about two months ago, which is why I have a good amount in our brokerage. So we don't have that anymore. The other thing, I guess I hate even talking about it or bringing it up, but there it will be. Inheritance down the road.

[Jim]

Why do you hate it? It's just reality. Well, I know we're not counting on it, but you. If you have parents of some means and you think that it is likely that, you know, it does change the trajectory. You hear me ask this question. He. Do you have someone you have to take care of? It's the inverse of that. So we just. It's just data I know, I know you're not wishing anyone ill or death on anybody, but like, what do you.

[Chris]

Suspect it will probably, it's probably 8 to 10 years and probably between 1.5 and 2, but. So I've been putting it in my head as maybe a million just to play it safe.

[Jim]

Yeah, yeah, yeah, that makes sense to me. And. But no one needs your help, obviously, because there's some money that's out there, right, in terms of your parents. Okay.

[Chris]

No one needs our help. And our kids are both launched and they're doing well. So that's all good.

[Jim]

Okay, great. Is there anything big coming up in terms of your spending that would argue for you to continue pseudo retirement, job, back to work moment. Do you. In other words, do you feel like.

[Chris]

Oh, you know what?

[Jim]

I really do have like another hundred grand on this house to do and like, maybe I should just do that.

[Chris]

The house is done. We have a wedding next year, which we're contributing about 50,000 to.

[Jim]

Oh, you got off cheap.

[Chris]

I know.

[Jim]

God, I mean, I hate to say that because I know people. You're hearing this, but they're. I mean, these weddings are insane. Everybody. I'm just saying it right now, okay? You know, you have a lot of money because of this, this rollover, obviously, and the 401k and the rollover and the 403b that has been rolled over. This is all your pre tax money, right? Hasn't been taxed yet.

[Chris]

Not as the roth. Yeah, the 104. Correct.

[Jim]

Okay. Now, has there been a conversation with your advisor about a strategy to extract this money?

[Chris]

Well, we just signed up with the planner, so we actually have a meeting sitting down with them or him in two weeks. So it's really in the initial stages. So he wants all of our expenses and all that stuff. And so we haven't had that conversation yet, but I feel really good. It's that. Can I say where it's at? Does that matter?

[Jim]

Sure, yeah. Why not?

[Chris]

So it's at Fidelity and we have all our money at Fidelity I. Which makes it nice and easy.

[Jim]

Yep.

[Chris]

It's right down the road from our house, which is great. I know the person. So we feel really good about all of it. But we haven't had those conversations yet. Which is one of the reasons I wanted to talk to you, because I trust you guys.

[Jim]

Yeah, I mean, listen, you're going to have this conversation. I mean, I think that there is a question that, that if you were to step down, right. How are we producing? I'm going to go Back one step. Are you and your wife both in good health?

[Chris]

Yes.

[Jim]

Okay, so I'm assuming that the game plan would be something like this and maybe your advisor will have something different. But I think that the game plan would be something like, okay, we have 10 years before you're both going to claim Social Security. Right. Ish. Do you know what your Social Security benefit is about?

[Chris]

I do at 67. Mine's 3716 and my wife is 2168. So 5884 at 70, which is what my plan is, is I'm 4608 and she's 2688. So 7300, basically.

[Jim]

I mean, so here's what we have to think about and your advisor will probably weigh in on this. And a lot of the Fidelity advisors have been, I've been talking to some of them offline and they've been talking about, you know, this may be a case where using an annuity for some of the rollover money because they can buy low cost annuities. So would there be a use case, potentially, yes, of buying an annuity for part of the rollover, the 1.775 and your wife's 560, using some of that money to fund an annuity where you get essentially paid, Right. You're going to get a, a salary for the next 10 years where you can cover your 15 grand a month. Would that be sufficient for you guys or some portion of that and be able to kind of get yourselves to your Social Security age of 70, where you're going to have this 7,300 and where, you know, obviously by the time you're 65, then you have Medicare. But you know, it's still going to be expensive. It's not going to be as expensive as the years before that. But for the next five years you'll pay up, you'll be okay. Then you have the money that you need. And then in 10 years, what would you be left with? Some leftover money from their retirement accounts. Because you do have a lot, $2.8 million. A lot of money that you have. I think I added that up correctly and that you then have the Roth that keeps going. You haven't touched your brokerage. The advisor will run some scenarios, but I think that's probably even if they don't use an annuity, I think that the idea is you use, you take the money out in these substantially equal installments to get you through the next 10 years, which solves the problem of your tax bomb that is potentially going to go off and that, you know, honestly at the end of that period there'll be some inheritance. So even if you depleted everything, okay. Which you're not going to do, but let's say that you depleted half of your retirement money, your non taxed retirement money and you end up in 10 years and you got say a million, a million and a half bucks that's still left. And then you get an inheritance eventually and you've got your house and you've got your Social Security. So it kind of sounds like it works to me. Again, I think that an advisor will have a much more detailed analysis of what could go wrong. But I think that's kind of the game plan and I imagine that that's what you thought the game plan was. Right.

[Chris]

You know. Yeah. It sounds much better when you say it.

[Jim]

Why is that? You're doing right, you're doing great.

[Chris]

I think. You know what? I've. I've always done everything, all my finances, our finances, myself.

[Jim]

Yeah.

[Chris]

And so it's just gotten to a point. I'm one of those people where I got kind of addicted to it, you know, looking at the market every day, looking at my. Literally every day, looking at our balance at fidelity.

[Jim]

You got to stop that. You got.

[Chris]

I know that it's driving me absolutely crazy and that's what I want to stop. And that's the main reason we got, we got somebody. Because I don't know how to take the money out. I don't know, you know, all those decisions that would drive me crazy. So I need a professional to do that.

[Jim]

Yeah. And I think that that's, I mean, you've done a really good job of managing this. I mean, obviously without the inheritance. I would tell you to keep working, by the way, I really would. Because I think that that's your little bunny at the end of the 10 year period. Because if you are going to spend 15 grand a month, which is not insignificant money. Right. That we need to make sure that you have enough of an asset base to be able to produce that. And producing 180 grand a year ain't nothing. And you can see that you could spend all the money in your Rollover account in 10 years pretty quickly. Right. Right. Okay. So now if you pretend that's gone, then what are we left with? And again, this is crude math, it wouldn't be exact. But you're left with having about another million bucks in your current 401k, your wife's rollover, that, that's a million bucks. Then there's the brokerage account, which would probably be at least a million bucks by then, plus the inheritance. Now we're talking. So all of this is to say, do you have the permission structure for a real rather than a pseudo retirement? Yeah, I think you will. I would just double check with the big question to say to a financial planner is, what am I guarding against? What am I not seeing? Tell me how this plan implodes. What's like you just to understand you may choose to take the risk. You know, they may say, okay, you know what, we ran this number, but like, stock market goes down by 40% next year or in the next few years, you got problems, and you want to know that. You may say, okay, I'll live with it. You may be able to live with that risk. But my number one question for the advisor would be like, tell me what the scenario looks like if I retire at the end of this year. What's the game plan to get the money out of the retirement accounts and what blows this plan up? Those are the questions.

[Chris]

Okay, that's very helpful now.

[Jim]

Yes, go on.

[Chris]

I'm sorry, Healthcare. I know that's supposed to apparently go up, I don't know how much next year, but I think of things like that.

[Jim]

Yeah, you should. But you've already accounted for that because you said 13 to $13,500 a month and then we went to 15. Yeah, it's not going to be more than $1500 for the two. It's not. And you know, there are. I mean, if you got really bored again, you could go work and do something equally as bored, boring and get coverage. You know what I mean? Like, it could be also, Chris, that you say, you know what, this job I'm bored with, but I could do something else for 50, 60 grand a year just to keep my mind working. And you know, I. I've heard people do all sorts of really interesting things and it gives them access to health coverage and they'll do that for five years. So, you know, maybe that's something that you could consider.

[Chris]

Yeah, okay.

[Jim]

But it's not. I don't think you're gonna need it. I think you're gonna be okay.

[Chris]

Okay.

[Jim]

I really do.

[Chris]

Yeah. I. I think I had it in my head that I. That we're okay.

[Jim]

You are. You are. I. You sound like a nervous Nelly. You're right up my alley. I am too. It's like, let me run this number another way.

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[Jim]

What if this happened? What if that happened? What if this happened? I know it's very, it can be very agonizing to live in that, that head of yours of ours. We all do this, okay? But you got a house that's paid for. You sold the other house, the kids are launched, you got a little wedding coming up. And let's see what the, the, the, the Fidelity advisor says, because I think there could be, I think you're going to be pleased with any results of these scenarios that they lay out. You know, I mean, are you going to bum out your friends if you say, I'm out of here?

[Chris]

Maybe a little bit, but that's okay. They'd understand. Okay, one quick question. I know that I, I was at 60, 40 in everything that we had, and when I moved over to fidelity, they're recommending 70 30.

[Jim]

Okay, how do you feel about that?

[Chris]

When they, when they explain it to me, I'm like, okay, I guess because we have the brokerage, because of, I'm trying to think of the reasons I felt okay with it because it's a pretty substantial amount. I just didn't know. I thought I was.

[Jim]

I think that it really depends on how you feel. Are you willing to forego upside to protect more of your downside? That's what you ask. And you might even say to them, okay, show me what this looks like. If I'm 6040 versus 70 30, tell me what my outcome looks like. Then I think, you know, you could have different choices. That's, listen, I'm always about, what am I giving up on my upside and what's the trade off there? What am I protecting against in the downside? They have all the data. I mean, believe me, everyone at Fidelity has this data at their fingertips, which is, you know, here's what we look at the, you know, any, any 30 year period, this is what we know, blah, blah, blah. But what I do think is if you feel like you want more comfort and you're willing to say, let me give you an example, they may say to you, well, 70, 30, we feel very comfortable generating your 15 grand a month, but if the markets go down, could you do 12, could you reduce your spending? Could you say, I'm not going to take a trip that year. That may be something that you think about. Maybe you say, yes, I'm totally willing to do that, or no, no way, and I'd rather have less money at the end of the day for the kids and the future grandkids and all that, and, and have a little more comfort today.

[Chris]

Right? Okay.

[Jim]

All right. It's not like right or wrong it's how you feel. That's one of the few feeling questions that we have.

[Chris]

Gotcha. I like that. Okay, that's very helpful. Thank you.

[Jim]

You're doing great. Chris in pseudo retirement, bored in his back to work going back for full retirement, not pseudo retirement. So good luck to you. Let us know how it goes and if you have any follow up questions after you have the meeting with the advisor, you let us know. Okay, good. I will.

[Chris]

Thank you so much.

[Jim]

All right, if you are like Chris and you're in retirement, then you're out of retirement, then you're back working and all these things are happening to you and you don't know what's next. I think it's a great time to at least check in with us and if it's something that's about retirement, but maybe it's about taking a new job. Maybe it's this idea of, oh my God, I don't know whether or not I should build a new home or I don't know whether I should sell my house. I don't know whether I can afford to jump into a new house or whatever it is. Get in touch with us. Go to jillonmoney.com, click the contact us button, write us a note. And if you'd like to join us on the air live, check the box. Mark will do everything else. He's so good like that. While you're on the website, please sign up for the free weekly newsletter. And don't forget that we've got all sorts of content that lives on the website. We've got another podcast, we've got a radio show. There's the blog, there's videos, there are resources. Everything [e-mail] youm can subscribe to us on the Odyssey app or wherever you find your favorite podcast. I wouldn't mind it if you could leave us a rating and review wherever you listen. And of course, try to put your hands metaphorically on someone's back. Someone needs a pat on the back today and it's going to make that person feel good. It's going to make you feel even better. Change your work, change your wealth, change your life. Thank you for listening. We'll talk to you tomorrow.

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