NerdWallet's Smart Money Podcast - Smart Planning Sessions: Go “Work Optional” and Move Retirement Funds Penalty-Free (Plus: Your Midyear Money Check-In)

Episode Date: July 14, 2025

In this month’s Smart Planning segment, a financial advisor discusses how to transfer retirement funds penalty-free and how to adopt a “work optional” mindset.  How can you check in on your financial progress halfway through the year? What steps do you need to follow to move your Roth IRA from a robo-advisor to a self-directed platform without paying taxes? Before welcoming listener Dan to the show to answer his financial questions, hosts Sean Pyles and Elizabeth Ayoola break down how you can do a mid-year money check-in, including how to audit your budget, spot and cancel unused subscriptions, increase retirement contributions, and curb emotional spending to stay on track for year-end goals. They offer a detailed checklist to assess credit, spending habits, and financial planning priorities for the remainder of the year. Then, Elizabeth welcomes Taylor Schulte, a CFP® and CEO of Define Financial, to dive into Dan’s questions, starting with how to reallocate investments when transferring a Roth IRA between platforms. They discuss avoiding taxes using the 60-day rollover rule, how to minimize market exposure during the transition, and why custodians like Fidelity or Schwab may be better suited than Robinhood in certain situations. They also help Dan evaluate whether he’s saving enough for a “work-optional” retirement, offer guidance on budgeting for life now vs. later, and explain what to consider when deciding on insurance coverage like disability or term life. Inspired to navigate your finances with an advisor? Use NerdWallet Advisors Match to find vetted professionals today at https://www.nerdwalletadvisors.com/match  A rollover IRA can be a great option for money in old retirement accounts. To avoid a tax hit, know the steps involved: https://www.nerdwallet.com/article/investing/how-to-rollover-401k-roth-traditional-ira  Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header In their conversation, the Nerds discuss: midyear financial check-in, how to track your spending, canceling unused subscriptions, Roth IRA transfer steps, rollover IRA rules, robo advisor vs self-directed investing, avoiding taxes on Roth IRA rollover, rebalancing Roth IRA, saving for retirement in your 20s, financial goals 2025, budgeting after emotional spending, how to increase 529 contributions, setting beneficiaries, updating estate plan, disability insurance basics, work-optional retirement, how much to save for retirement, starting a financial planning firm, emergency fund tips, automating savings, avoiding subscription traps, midyear credit check, reallocating investments, understanding investment fees, budgeting as a single person, how to set financial boundaries, pay yourself first strategy, how to start budgeting weekly, tracking financial progress, saving vs spending balance, transferring mutual funds, how to do a 60-day rollover, and Roth IRA transfer tax implications. To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email [e-mail]. Like what you hear? Please leave us a review and tell a friend. Learn more about your ad choices. Visit megaphone.fm/adchoices

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How those ahead stay ahead. Sean, I'm about to grill you and ask you about those goals that you said that you had set earlier this year for your finances since we are now halfway through the year. Mm-hmm. Are you ready to be grilled? I think so.

I can handle it. Bring it on, Elizabeth. Welcome to NerdWallet's Smart Money Podcast, where you send us your money questions and we answer them with the help of our genius nerds. I'm Sean Piles. And I'm Elizabeth Ayola. On this episode, we talked to a CFP and listener about allocating investments for our smart planning segment. But first, since we're in July, I'm going to grill Elizabeth and then I guess she's going to

grill me about how much progress that we've made toward our financial goals this year, also known as a mid-year money check-in. And we love those. Well, I love those sometimes. Me too. So let's start by giving folks a quick framework for a mid-year money check-in. And we love those. Well, I love those sometimes. Me too. So let's start by giving folks a quick framework for a mid-year check-in. Set aside an hour, just an hour, and review your financial goals. Those can be the lofty ambitions that you had

at the beginning of the year, or longer-term goals like getting your emergency savings built up. Then look over your spending for the past few months. What are you proud of? What makes you feel maybe a little embarrassed? A few other areas to review are your debt, your retirement contributions, and your investments. The idea is to see how you've managed your money over the first half of the year. Find a few areas to make some adjustments, then

plan for the rest of the year because the holidays will be here before we know it. I'm going to add two things to that list, Sean. It may also be a good time to get a free credit report and check your credit health since we're mid year. And also you want to start thinking about planning for 2026 taxes. So you're not stressed out come January. Yes. Tax season turns out is never ending, I guess. So Elizabeth, let's start from the top.

Tell us what your goals were again, as you started out 2025. So for a refresher, first of all, I wanted to tidy up my budget because I had cobwebs. I also wanted to better track my spending, which is tied to my budget. The third thing was I wanted to replenish my emergency fund since it's now been a year since I've moved and I can't blame it on moving costs anymore.

And then last but not least, I wanted to bump up my retirement savings rate so that I can save more and hopefully one day achieve fire. Okay, pretty well-rounded list there. And where are you with all those things? Well, I am proud to say that I have cleaned up my budget. I updated my income and expenses, which had changed since the last time I updated it.

And then while I was doing that, I actually realized that I had multiple subscriptions to things that I don't even use. I even had two Prime memberships. Can you imagine that? Those are not cheap, Elizabeth. They're not. So they were just taking all my money and guess what I did? I canceled both of them. So subscriptions are one of those areas that's so easy to just acquire them without thinking. And then you are paying it month after month and you stop using the service and then you're

like, why am I paying for this? Just go in and cancel it. You'll be so glad that you did. Absolutely. And you know, I think everyone has fallen trap or most people to the free trial thing. And then you sign up for something and forget. But usually now I set a calendar reminder

so I don't forget. Oh, that's a good tip. Another thing, I started checking my spending weekly. So in all honesty and transparency, because that's what we do on this show, I used to check my spending, I think, at the end of the month, really. And then I'd be like, oh my God, who spent all that money? It couldn't have been me.

It was you, girl. It was you. It was you the whole time. Yeah. It was me the whole time. So spending weekly has definitely made me more aware of how much I'm spending. And sometimes I even check bi-weekly so that I have a better idea of what I'm allowed to spend for the rest of the week.

I've also been thrifting versus doing more online shopping so that I can be fabulous on a budget. Good for the environment. That's great. It's good for the environment too. Yes, Sean. I've been saying no to outings more. And then on weeks I overspend, I usually just cut back during the following week.

So I would say those are the major changes that I've made in terms of my financial goals. Does that help to reach your goal of saving more? Absolutely. I'm so proud to say, so I know everyone's different in terms of my financial goals. Does that help you reach your goal of saving more? Absolutely. I'm so proud to say so. I know everyone's different in terms of how they save, but I do like to automate my savings. But for the time when I had a lot of overhead, I started pausing my automations

and just putting in money when I could. But I also realized that that was making me overspend more because I just had more to spend, if that makes sense. That's why I'm a big fan of the pay-yourself-first strategy, where the money doesn't even enter my checking account. I have it allocated into my various savings buckets and that way I know I can't spend it unless it's for that specific purpose.

So now I've gone back to that and it feels great because I know that I'm saving every month and what I got left is what I got left. There you go. Okay. Are there any areas that you think you still need to improve a bit? Hmm. Yes. So I've said multiple times on different episodes

that I can be an emotional buyer. So I think there's always gonna be room for improvement there, but I still have a better handle on it now because I am budgeting, if that makes sense. So even when I am emotional buying, it's like, okay, girl, I know you're in a great mood, but you can only spend $100 versus, oh, I don't know how much I can spend

and I'm just gonna spend it. It seems like you helped establish more firm guardrails for yourself. So that way, you know your habits, you know your triggers, but you're not allowed to go as far in excess when you do want to emotionally buy something. Exactly, because I have a clear number.

I will say, though, there is one thing I still haven't done, and that is updating my beneficiaries on my estate plan. And I should, but since we're being transparent, I'm just too lazy to find a notary. And yes, I know I can go on Google and find one and I'm going to do it before the year ends. Oh, actually, there is one more thing as well. I just gave everyone advice about checking their credit report and guess who hasn't done that?

Me! So I shall be getting my free credit report also. One thing I'm going to advise you look into Elizabeth is the beneficiary designations on your accounts, like on your savings account, your retirement account. You can just set those up in your account settings and they don't need to be approved by an attorney or a notary or anything. You can just do it in a matter of minutes. It's super easy.

It's actually much easier than having a proper well set up. I agree. And I should be clear on that actually. So I need to update my estate plan. So I actually have my estate plan under most of my accounts but I need to update the people that I have on my estate plan in terms of who's going to distribute the funds. Who you're writing out of the will. Exactly. Oh I didn't want to be shady but exactly, exactly. Some people got to get out of there.

Okay well let's talk about your plans for the rest of the year. Are you making any big changes or how are you feeling about the plan you set out at the beginning of the year? Well, honestly, I'm gonna give myself a big pat on the back because I can be hard on myself. And I actually am very proud of my progress

and there's not really much else to fix. So I'm gonna continue with the positive habits that I've developed for this year. I am very happy with my savings rate and how my budget looks right now. One change that I did make is I was going back over all my accounts and I saw that I do have room now that I see my budget more clearly to increase my son's 529 contributions. So I have still automating those, but I've increased the amount that I'm putting in there and that's it really. So we are just setting it, forgetting it, saving and living our best life.

That's great. Well, you should be proud of all that you've done. I'm really glad that you've been able to check in with your spending more and you feel more in control of that. Thank you, Sean. Thank you. Thank you. But let's see where we are in December.

Cause we're going to do one more check in. Yeah. I'm going to hold you accountable. I love it. Now it's your turn. I'm going to grill you Sean. So where are you with your goals? Remind us of what your goals were, first of all.

Yeah, I had a lot that I wanted to accomplish this year and I still do want to accomplish. Starting out January, I wanted to sell my house. I wanted to reduce my discretionary spending, especially on clothes to save more. I wanted to start my financial planning firm, which is a financial investment too. I also wanted to invest more

regularly and rebalance some things in my garden, which I think is a financial decision too, because I was figuring out whether I wanted to spend money on my plants or propagate them and basically make more plants for free. So I had a lot on my plate. That is a lot of things, Sean. So now you have to tell us one by one, just like I did, what have you done, what haven't you? Okay, going through, I actually decided to rent out my house instead of selling it. I couldn't quite shake my 3.125% interest rate. Yes, I'm glad about that for the rest of my life. And that was a whole process,

and it wasn't cheap to move out of the house, but it's been great the first couple months of having a tenant in my house so far. We'll see, knock on wood. Hopefully it keeps going well. And then, you know, I did have some moments of emotional spending. It's been a really up and down past few months, just in the world at large. And I am aware that I'm doing it like you, Elizabeth. And I have my fun money budget that more and more has gone toward this emotional spending.

And I think I'm at a point now where I'm kind of coming to terms with it and reigning myself in and it feels better to be more in control of that. But I know I have this tendency, so it's a matter of checking in with myself and honestly communicating more with my partner about my own spending. Cause I find that when I'm vocal about what I want to buy, I'm less likely to buy it, but if I'm doing it all on my own, like scrolling privately on the sofa, it's so much easier to hit that buy button for some reason. What is that about?

Is it hearing yourself out loud, say like, I want to buy a new lawnmower and you're like, come on, Sean, do I really need a new lawnmower? What is it? I don't need a new lawnmower. That's for sure. But I think part of it is, yeah, it's like, do I need this shirt that costs too much money? No.

Garrah's going to say your closet is overstuffed as it is. You have a lot of clothes, so you can just spend that money on me instead. That's what he was always asking for an allowance. Sounds like my son. But I think it's just like kind of the reality check of let me get this out into the world. Let me be accountable to myself and to my partner and my budget and see if it aligns with my values where there's this almost process of self deception, where if I'm sucked into like a dopamine hole scrolling and wanting to buy, I can tune out the part of me that knows

that I shouldn't be doing it. And this helps me interrupt that bad thought pattern. So I think that's what's going on there. I think it's so important to talk about this whole emotional buying thing, because I think everyone is prone to it to some extent, right? And just kind of dispelling or rather taking away

that shame that comes with it. And like you said, being aware of your spending. So I'm happy that you're doing that. And I'm happy that you're about to trade some shopping for giving your partner an allowance. That sounds amazing. We'll see if that happens. I'll let you know. Garrett will be the first to report. But okay, back to my goals. Back to my goals.

I have a financial planning firm now. I got it up and running. Piles Financial Planning LLC. I'm excited to say is taking clients. So I've been starting slow and getting things established. I have my rinky dink website and email and all of that. It costs a little more money than I was expecting because I had never established a financial planning firm before and I didn't know how much money FINRA and the

state of Oregon would want for me. And it was kind of a lot. So that took some of my money, but I'm really proud that I got my company up and going in the time that I did. And I'm excited to see how it pans out. So that's been really cool to see come to fruition. Huge accomplishment. Congratulations. Thank you. And additionally, I am investing more. I'm upping the amount that I'm putting into my brokerage account. I have to buy weekly direct deposits into it, and that just feels good to do. And I also recently hit a big retirement milestone in my 401k. I don't like to brag about specific numbers because I feel

it's a little bit personal, but this is a big one. I recently crossed over two hundred thousand dollars in my 401k. That's amazing. Yeah, you're doing great,000 in my 401k. That's amazing! You're doing great, Sean. Thank you. No, but I know the feeling. It's like, oh my God, I'm rich now. Not really, but almost.

I feel like, you know, maybe one day, but it was kind of eye-opening. I looked back through all of my contributions over the nine years I've been at NerdWallet, and my first one, I think it was like $200 or something like that. And from that initial $200, I've grown it to this and it feels great. So I'm not going to let my foot off the gas, but it's nice to see all of the fruits of my labor and my diligent saving. That's right. Consistency.

That's what it looks like in investing. And once that compound interest starts kicking in, you just watch your money grow and it's a great feeling. Absolutely. We do also have to hear, because for the listeners who will not be able to see Sean on social media, he has on a Cher shirt. So I need to know what Cher song is going on your playlist

for your wedding. Man, there are so many heartbreaking Cher songs that are just are not appropriate. But I love her cover of Nancy Sinatra's Bang Bang. Oh, that's fun. That's like another sad song. But I think it would be fun for a little dramatic moment at the wedding.

And Elizabeth, you're wearing a Prince shirt. What's your favorite Prince song? Purple rain, purple rain. That's a classic. I want everyone to know that we didn't plan to wear these band t-shirts today. We are just so in sync. Here we are bringing our jams. I know.

So listeners, Elizabeth and I just did our little mid-year money check-in. Now, I'll encourage you guys to do the same. Again, set aside an hour, only an hour, out of your entire week and start by writing out where your goals were at the beginning of the year, then see where you are with those goals now. We know that life happens and any number of interruptions or emergencies can derail your plans. So just see how you can adjust them. Then look for a few areas where you want to make some improvements and get yourself set up for the rest of the year.

And you just heard Sean and me brag a bit about what we've done with our money this year and where we wanna make some changes. And we wanna hear what you've done with your money too. Please, please share it with us. You can do so by leaving a voicemail or text us on the nerdy, braggy hotline at 901-730-6373. That's 901-730-NERD to share your biggest money win of the year so far. You can also email them to podcasts at nerdwallet.com because

we're all about sharing our successes here on Smart Money. All right. We're about to get to this episode's smart planning segment, but before we move on, we have an announcement. We're running another book giveaway sweepstakes ahead of our next Nerdy Book Club episode. Our guest next time is Dana Miranda, author of You Don't Need a Budget, Stop Worrying About Debt, Spend Without Shame,

and Manage Money with Ease. To enter for a chance to win our book giveaway, send an email to podcasts at nerdwallet.com with the subject book sweepstakes. without shame and manage money with ease. To enter for a chance to win our book giveaway, send an email to podcasts at nerdwallet.com with the subject Book Sweepstakes during the sweepstakes period. Entries must be received by 1159 PM PT on July the 31st. We want you to include the following information.

Get a pen if you need it, your first and last name, email address, zip code, and phone number. For more information, please visit our official Sweepstakes rules page. All right, let's get to this episode's smart planning segment where we talk with a listener about reallocating investments. That's up next, stay with us.

Many of our listeners are looking for professional advice on elevating their wealth. So, we invited another financial expert onto the show to take a deeper dive into listeners' financial questions and also to provide smart strategies for building and leveraging their money. Welcome to Smart Planning. Let's begin. [♪ Music playing on speakers and speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers' speakers So today we have Dan on the show. We're going to answer his listener question. Hi Dan.

Hey, thanks for having me. Thanks for coming on. We also have Taylor Schulte, a CFP and the CEO of Define Financial. He's going to help us to answer Dan's question today. Welcome to Smart Money, Taylor. Thanks for having me, Elizabeth. So let's quickly get into it. Dan, can you first of all tell us, it's the middle of the year,

and I would love you to describe your year so far in one word. Ooh, exhilarating. Oh, that's exciting. You wanna tell us why you're exhilarating? Well, I released my first single, and so that's pretty exciting. And you know, it's like whatever,

like a thousand listens on Spotify, so it's nothing big, but that's- Awesome. It's a big deal for me, you know? I've been wanting to release music my whole life, and I finally took a step towards that and I hope to take more steps in that direction Congratulations, and now I'm gonna ask you to describe your finances in one word

Contained also very good. So on that note Dan you have contained finances Can you tell us why you're on the show today and what you'd like to discuss regarding your contained finances? So I appreciate your show. I listen pretty religiously and I think there's a lot of wisdom and insight. That's shaped how I've made my financial decisions as well. I use the information and make some educated choices for myself. I am interested when it comes to saving for retirement. I kind of felt overwhelmed when I first started in the early 20s. And so I started with an Ally robo advising account. And basically, as I've grown in comfortability with investing and general retirement finances,

I have a Robinhood account now where I have a self-directed account. So I don't love on my Ally account having about'm having about $100 a year annually taken out for the fees for the robo advisor. I feel that's money that could be growing exponentially for the next 40 years. And so as the money continues to grow as well in that account, it will go up from $100. And so I'm interested in reallocating my funds between my brokers out of Ally and into Robinhood. But because it's not a direct transfer, I can't do that because I have bonds and mutual funds that are in Ally that are not transferable to Robinhood.

And so I'm curious about the process of reallocating funds between institutions. Taylor, would you like to answer that for Dan? That's a really good question. And Daniel, I mean, I loved your word there contained. I don't know if I've heard that before. So I mean, great job on containing your finances and starting to take control of these things. Of course, there's certainly a reason for some people to pay an advisor or pay a robo advisor a percentage fee every year to help them with something that either they don't want to do or they don't know how to do.

It sounds like you've learned a lot and you want to start to maybe self-direct or self-manage some of these funds. So it sounds like you've made a lot of progress here on your investing and savings journey. In short, this does present one of the challenges of using some different up and coming services like Robinhood. I mean, Robinhood is a fantastic app, very slick, very user friendly and easy to use, but you're gonna run into limitations and restrictions

like the very one that you're running into right now, where if you were to leverage a custodian like Fidelity or Schwab, where fees would be very similar, if not the same to Robinhood, maybe you don't get some of the signup bonuses that Robinhood has going right now, but Fidelity and Schwab being much friendlier and more open architecture, allowing you to transfer different types of investments to Fidelity, not have to sell anything or Schwab for that matter.

So this is one of the restrictions and each robo advisor, in my experience, has some kind of unique limitation, even some of the bigger ones like Betterment or wealth front that we've run into in the past. To answer your question, there's not going to be any taxes if you were to sell the investments in the Roth, go to cash, and then transfer that money over to Robinhood. Now in some cases, I don't know the exact transfer process as to how Ally would handle it or how Robinhood would handle it, but sometimes they'll literally mail you a check for the amount. And then you need to take that check and go deposit it in your Robin Hood Roth IRA. And as long as that transaction happens within 60 calendar days, if you want to

learn more, you can Google or search the 60 day rollover rule. So as long as this is all done within 60 days, liquidate everything, take your check, check gets mailed to you. Then you take that check to Robinhood and deposit it in your Roth IRA. As long as you're within those 60 calendar days, you wouldn't be penalized for anything. The downside to doing this, it's not an extreme downside because you're only 28 years old. Your investing

journey is long, right? You've got decades ahead of you to save. So it's not going to impact you really at all, but in the near term, you know, you're going to be out of the market for a period of time. So let's say you're out of the market for, I'll be conservative and say 14 days or 10 trading days. Look, I mean, the market could skyrocket during that time and you might miss some upside, you might miss some downside.

We don't, we don't know. We don't know what's going to happen. That's typically the concern in these situations like, Oh gosh, I'm going to be sitting on the sidelines for a period of time during this transaction. It's typically the concern in these situations. Like, oh gosh, I'm going to be sitting on the sidelines for a period of time during this transaction. It's not the taxes because the taxes are irrelevant as long as you follow the 60 day rollover rule. But because you have decades to invest,

20 years from now you're going to look back at this time period. It's not going to matter at all what the market did during this five or 10 day period. And I'd like to add, Daniel, that you can learn more about rollover IRAs. We have a wonderful article on NerdWallet, which we will include in the episode show notes to learn more about rollover IRAs.

Awesome. Thank you. So Dan, it's awesome that you're investing and that you are growing on your investment journey. Can you tell us a bit about your broader investing goals? So what are you investing towards? What are your overall goals right now? It's a great question. And to be honest, it brings up life questions in that, you know,

who am I? What am I doing? Existential questions. So basically, I'm 28 years old. I think I thought I'd be married by this time in my life, and I'm not. And I enjoy being single. I have a house, and I'm blessed, and it's beautiful. But I think when I started saving for retirement, I was thinking, okay, I'm young now, let me start to save. So when I have a family and I have kids and my budget can't allow for saving for retirement as much because I'll have demands of a family, let me start now. And so that was my original plan. And I just want it to be financially wise. And so now what I'm coming up against is now that I'm 28, what if, what if I don't get married soon?

What if it's not going to be that And I'm saving so diligently for a future, but like, what about living now, right? I think that I'm coming up with that as well. So my contained finances are like, yeah, well, I'm doing all the things, but like, I also, I kinda wanna go on vacation. I kinda wanna do something and enjoy life a little more, or maybe more than a single, release a whole album,

and these things cost money. What I'm really working out is, whether I get or not, I want to be self-sufficient with my finances. I think that's very important. I want to be able to have enough money saved for retirement that I'm not a burden to anyone or I'm not able to provide for myself and I want to have a comfortable life. Also at the same time, I am currently working as a baker part-time and I'm part-time staff at a church. And I believe ministry is a lifetime call. I don't retire from that, right?

And so whether I would love to work for a church and not get a paycheck at all, like if I could fund myself, right? So I think like retirement and saving for that for me, that's part of what that looks like, is being able to be generous with my time, with myself, with my resources. I think in order to determine how much you will have to do both, because it is possible to do both, enjoy your money and also save towards your financial goals. It might be helpful to get a picture, maybe an overarching theme of what your finances look like. So I'll let Taylor take that off.

I'm just curious to hear from you. Like when you say saving for retirement, what does retirement look like to you? Is this I'm 28 now and I'm going to save and invest for the next, you know, 30 ish years and I want to retire at 65 and like literally shut it off and quit work and I've got my nest egg and now I'm going to go, you know, work for the church full time and I don't need to worry about getting paid. Like what does retirement actually look like to you? What are you saving towards?

What's the end goal? That's not so easy to answer. I don't see myself ever stopping working. I don't see myself ever stopping working. I don't see that. So like you said, yeah, like in 30, 35 years, being able to just continue the ministry work and not need a paycheck. That would be pretty ideal. In these situations, I like to use the word work optional. Have you heard of that word before? Sure. Yeah. Okay. I love talking about making, making work optional is kind of my retirement plan because you're 28, a lot's going to change between now and typical retirement age. Not in terms of like, do I want to retire? Maybe you love what you're doing and never want to stop, but it could also be the amount of money that you think you need. Maybe today you think I need a million dollars to retire, but 20 years from now you realize, no, my goals have shifted and I need a lot more money. I kind of equate it to, you know, taking a prescription. We wouldn't just take a prescription just because a friend told us we should, or

my friend's taking this one, so I'll take the same one. We're diagnosed first, right? By a doctor who says you're diagnosed with this thing. And as a result, you should take this prescription. And I kind of look at retirement planning the same way. Like what's the diagnosis? What are we trying to solve for? And then what's the prescription that we need to follow in order to reach that

goal, knowing that that goal is going to move and life is fluid and nothing's a straight line. So I think it's worth documenting some of those things and what it looks like. And for me at your age, I think one of the most important things that you can do is to track your expenses. It sounds so silly. I'm not saying put yourself on a budget. I hate budgets, but tracking your expenses and knowing exactly where every penny goes because every retirement planning conversation comes back to Well, how much do you spend? How much do you need to spend in retirement to fund your lifestyle? I'm a big budget guy. Unfortunately, and I'm paper. I'm old. I'm old school. Sorry to cut you off

But I've got it written out every everything, you know? Perfect. I tell clients the same thing. Like I don't care what your system is. I don't care if it's pen and paper, if it's some fancy technology, Excel sheet. It doesn't matter, but it sounds like you've got that habit now and you've got a system now and that's great. So continue that as you save more money and make more money and have larger investment accounts, don't stop that habit because that piece of paper or whatever it turns into is going to be wildly helpful as you continue planning towards retirement.

So tracking your expenses is a big one. And then I do love planning for these worst case scenarios. That's how I think about planning. I love to shock financial plans and say, what if this crazy thing happened? What does that do to the client's plan? And then from there, okay, if that happened, what are some options that we can pursue to recover from this crazy catastrophic event?

Now, when and if that were to happen, we're not trying to think on our toes in the moment and get emotional and make bad decisions. We've already thought through that this could happen. And if it did happen, here's what we can do as a result. The last thing I'll say here before you maybe ask some follow-up questions is along those lines of catastrophic events, we want to make sure that we are protected against these big things. So when it comes to insurance, I know you'd mentioned in the notes that you have catastrophic health insurance. It's great to be covered for catastrophic health insurance, but it probably makes sense to have additional health insurance on top. Maybe you do have that as well. But we want to make sure we have the right types of insurance in place.

We want to protect against the big things and we want to skip the small things. So if you have a proper emergency savings set aside in cash, we can probably skip the roadside assistance insurance and we can skip the iPhone insurance because you have adequate savings to pay for those things out of pocket. So we want to make sure we're insured for these big things. And I mention this because you had said something like, if something were to happen to you and you couldn't work, which brings up the idea of disability insurance. So do we have proper disability coverage in place? These things

at your stage are really important in addition to making money, saving money, investing properly. And Taylor, Dan also asked on a day to day basis, how does he know how much he can spend in terms of enjoying his life and saving for retirement? So how can he, on a practical level, find that balance? Knowing your income and expenses can be a good place to start, so you know how to slice up that money.

Yeah, it is a good place to start. Dan, there's a great book out there called Die with Zero that talks about some of these concepts. The generation of clients that, that I work with. They are largely baby boomers and they had done a great job saving money, squirreling money away, and a lot of them were passing away with millions of dollars, money that they never spent. And so there is this shift into thinking, I want to enjoy my life.

I don't want to die with millions of dollars in the bank. So Bill Perkins, the author of Die with zero talks about a lot of these concepts and this kind of balancing act. You can nail down all the things that we're talking about today, but there's still leaves this question mark of like, how much can I live in the now versus plan for the future? And there's not an exact science to it. So you have to be careful because, and I live this way too.

Like I want to enjoy my life now. I want to take my kids on trips. I want to travel. I want to spend now because I don't want to die with millions of dollars, but that line can be crossed too far really quickly. Right. And you can go too far in this direction of yoloing too much. And now you're really sacrificing your financial future.

So I guess it's a long way of saying your answer is going to be different than my answer. I think what's most important is that you nail down all of the basics that we're talking about today. You nail all these things down. So, you know, why I have an emergency fund in place. I'm tracking my expenses month after month. I've paid off, or I've got a plan to pay off high interest debt. I'm maxing out all the available retirement accounts that I've available.

I'm maxing them out every year. I've got the proper insurance in place. Nailing down all these things starts to, I think, make it more clear, like how much can I live in the now versus save for the future? That's helpful and I'm looking forward to read that book. Thank you. So Dan, how do you feel you're going to move forward based on the things we've discussed so far? I feel like I, based on our conversation, I'm less scared about liquidating and transferring like it seems pretty pretty normal and and nothing's going to be crazy and I'm gonna lose my money or have to be taxed so I feel comfortable with that. Yeah maybe one more

thing on that topic is I wouldn't try to navigate this transfer on your own. Sure. Typically if I want to get my money to Robinhood I should work with Robin Hood to get that money over there. And they should have a process in place to guide you through that. So I wouldn't go to Ally and just liquidate everything and tell them to send you a check in the mail and start to like, try to figure this out. Start with Robin Hood and say, here's what I want to do. Tell me step by step what I need to do to make this happen, to make sure that I avoid taxes, fees, all that sort of stuff. Fantastic. That's great.

Thank you. Dan, do you have any more questions related to retirement? Or at least do you have any more clarity around it than when we started the conversation? While I have Taylor here, one thing you had mentioned earlier was like, okay, well, maybe the big goal is to have a million dollars for retirement. And that's, that's your big, that's you have arrived. Like, I think back to when I was a kid, like 20 years ago, a million dollar home was a mansion, but a million dollar home now I'm like, oh, that's kind of like an everyday

home. So like, in 30 plus years, a million dollars isn't going to be worth a million dollars, like what I think of as a million dollars. So what's a real number I should be looking at? And I get you saying every single person is different for what they want for their retirement to look like. But like what's an average decent retirement that's going to be good for someone.

I don't know. It's going to be, it really, I hate to say that, but it is going to be different for everybody. Because Dan, you know, you mentioned that you produce or write music. Maybe at age 60, you've got residuals flowing in from all this music you've created. The amazing. And maybe a million dollars is more than you need

because you have all this residual income coming in for the rest of your life from all these amazing songs that you produce. Like we just don't know that. That's the challenging part. Now, as a starting point, I think you can plug the basics into a retirement calculator, be very conservative in your assumptions. We don't need to assume 10% returns every single year for

the next 30 years. So we can be conservative in our assumptions and maybe bump up inflation a little bit and bump down our rate of return assumptions and stress the plan a little bit and see where that gets you. The number is probably going to look absurd. Right. You're like, you know, I don't need $10 million, but you can still go through that exercise to see where it gets you. Because again, like life is not a straight line. There's going to be all sorts of bumps in the road. You're going to go backwards for a period of time and have to recover. Like, that's just part of life.

Yeah. Um, so I don't know the exact answer to that question. And that's why I typically, like, I think it's good to sketch these things out and have a loose idea of what we're planning for, right? We don't want to just be aimless about it. It's gonna change. But having a loose idea of like where we're headed. And then I think what's most important at your age

is making as much money as possible, doing something that you're passionate about, of course. Like we're not just selling stuff we don't believe in, but making money, saving money, and investing your money wisely, really kind of set it and forget it, right? We're not day trading stocks here. We're making money, we're saving money, we're investing it wisely, and we're not touching it and letting that money come bound for a long period of time.

That's really going to matter more than anything at this stage of life. And on top of that, everything else we talked about from tracking expenses and making sure we have proper coverage in place and emergency savings. So Dan, do you have any other questions? Yeah, actually something you had mentioned earlier was disability insurance. That's something I'm not familiar with. I don't know your professional situation. It sounds like you're working in a couple of different jobs here.

Uh, but typically a bread earner or primary earner in the family would want to carry disability insurance if he or she was unable to do their job. And there's a lot of little definitions in there. So all these policies are a little unique and different. So you'll want to work with an insurance broker who can explain all this to you and help you choose the right policy. But just in general, if you are not able to do your job, you're still saving for retirement. So if something happened to you today, Dan, you could, you literally couldn't do your job.

We've got 30 years of savings that you're going to miss out on. That's where disability insurance comes in. It's like, well, Dan has disability insurance. He can't do his job by all these definitions. And so, you know, here's a sum of money to fill that gap. So his family can retire. So it is really important insurance for someone in the working world who has a stable job. It is a little bit more costly than other forms of insurance, like term life insurance would be

incredibly cheap for you, Dan, where you might have some sticker shock on a disability policy. You may determine it's not as important for you now because you don't have a family, right? If something happened to you, is anybody on the hook for your debt? You know, is there anybody that you need to help fund, you know, for retirement? I don't know. So, you know, maybe for you at the moment, you decide I'm willing to take that risk. If something happened to me and I can't work, you still have to think for yourself too. It's like, how are you going to get by day to day if you can't generate income? So I think it'd be a worthwhile exercise to look into disability

insurance and learn about it. Retrieve some quotes, learn about some of the different definitions there. You might get just like a bare bones policy to start. And as you start to earn more money and feel even more contained with your finances, you start to increase that policy. But it is wildly important insurance. It's one of those just absolutes that need to be in place in addition to the right type of umbrella, the right type of auto insurance, having term life insurance, things like that.

That's great. Thank you. All right, Dan. Thank you so much for coming on. I hope this information was helpful. I hope you're able to decide what to do about your Robinhood transfer. And I also want to wish you good luck with the single. Thank you so much. I hope by the next time we hear from you, you have over 10,000 listens and more and more and more. That'll be amazing.

Thank you. And Taylor, thank you so much for coming on. Thanks, Elizabeth. Really appreciate it. If this episode inspired you to reach out to a financial planner, our SEC registered affiliate, NerdWallet Advisors, can help through their Advisors Match service. All you have to do is visit nerdwalletadvisors.com slash match or click the link in the episode

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