127. Ask Tori: How Do I Retire?

November 30, 2023

The following article may contain affiliate links or sponsored content. This doesn't cost you anything, and shopping or using our affiliate partners is a way to support our mission. I will never work with a brand or showcase a product that I don't personally use or believe in.

Tori, what do I do when it’s time to retire?

What should I do with an old 401k at a former employer?

Should I invest if I’ve maxed out my Roth IRA but not my 401k?

If you’ve ever had similar questions and wondered about the answers (or if you’re the person who sent these questions), then you’re in the right place today.  In this episode, host Tori Dunlap is answering these questions and more.


  • The strategic advantages of investing over paying down mortgages
  • The importance of planning for retirement in advance
  • Tips for managing a 401k after leaving a job 
  • The pitfalls of financial institutions like Edward Jones 
  • Options for transferring investments, including DIY platforms, robo-advisors, and Stock Market School

Additional resources:

How to Start Investing

Financial Feminist book

Stock Market School

Free Investing Workshop: Stock Market Secrets

What you need to know about mortgages with Kate Wood


Feeling Overwhelmed? Start here!

Our HYSA Recommendation

Order Financial Feminist Book

Become an investor and join our Investing Community, Treasury, with Investing 101

Behind the Scenes and Extended Clips on Youtube

Leave Financial Feminist a Voicemail

Financial Feminist on Instagram

Her First $100K on Instagram

Take our FREE Money Personality Quiz

Join the Mailing List


Tori Dunlap:

Hi, everybody. Welcome back to the show. My name is Tori. I host Financial Feminist, which is a show committed to talking about how money affects women differently and also how we can use money as a tool of protest in this bullshit capitalist society. If you’re an oldie, but a goodie, welcome back. If you’re new to the show, welcome. Hope you stick around for a good time and a long time. A couple housekeeping things before we get started. Y’all know the drill.

If you love the show, the easiest thing you can do to support us if you’ve ever gleaned just a little ounce of value from this show is subscribing. It’s one of the most helpful things you can do to support your favorite podcasts and is literally just a click of a button. So wherever you’re listening right now, hit the plus button, hit the follow button, hit the subscribe button. They’re all the same thing, just called different things. So that helps us a lot and we really appreciate it. If you want to go above and beyond, share the show with friends, leave a five star review.

We so appreciate the support. All right, we are doing a fun little ask Tori today. We haven’t done one of these in a while. You can submit voicemails with your questions. We are going to take questions from our voicemails that you all leave for the show, but also from our stock market school community, which is our year long investing education platform hosted by me where I offer step-by-step investing guidance and support, and monthly coaching and live workshops. You can get all of the deets about that down below.

And then we’re also going to take some questions from our just general community all about investing. If you are wondering where to go after this episode, if you listen to part of it and you’re like, “I want more,” well, we have a bunch of episodes on investing in the back catalog of the show that we’ll link, as well as an entire investing chapter in the book. We also have stock market school, so we’ve got a bunch of options of where to go next. All right, let’s take our first question about investing, and this is from our Facebook community, so I’m going to go ahead and read it here.

All right, can we talk about paying down our mortgages versus investing? Recovering Dave Ramsey person here. I’m buying a home after selling a home from 10 years ago. It has quadrupled in equity. My new mortgage payments will be about $450 a month. Oh my god, that sounds so nice. Sorry. $450 a month. I’m not sure where this person lives, but oh, I kind of wish I lived there. Gosh, a full disclosure, and maybe I’ll talk about this on an episode, and Kristen doesn’t even know this.

Kristen, this is going to be news to you. I looked at a house this weekend that I was in serious talks about purchasing and I was doing the math on how much this mortgage was going to be, and I don’t even want to tell you what the monthly payment was in Seattle. It was awful, and especially with interest rates as high as they are. So I just bless this person who’s only paying $450 a month. Oh my god, that sounds like a dream. Okay, my new mortgage payments will be about $450 a month over 25 years, which is unbelievable.

Yes, it is. Okay, I’ve done the math. Over 25 years with my current savings plus my new yearly savings, which is cutting out the commute and the equity built in my sold home, minus the mortgage interest I would pay over 25 years, it’s still a projected difference of $300,000 versus paying off my home in five years, which would be less mortgage interest paid, but also less money in long-term investments. So in case you’re wondering with all of that, basically she’s asking, again, do I pay down my mortgage quicker or do I invest?

She says, “Does anyone else feel a weird emotional pull to pay off your mortgage ASAP even when you’ve crunched the numbers? I hope all of this makes sense. So many thoughts flying around in my head right now. I would absolutely love Tori to talk about this on a podcast.” I’m doing it. Dear listener, dear reader, I’m doing it. Okay, so let’s talk about this. This is a question we get all the time. Again, should I pay down my mortgage faster or should I invest instead? The quick and dirty answer is you should invest instead.

I have an entire free investing workshop called Stock Market Secrets that we will link down below, and this is actually one of the myths I debunk that all of your debt needs to be gone before you start investing. Now, some of your debt needs to be gone. High cost debt like credit card debt should be gone before you prioritize investing.

But with something like a mortgage where your interest rate is normally three to 4%, right now it’s not great, but it’s normally under that seven to 8% that we could be expecting in the stock market, it’s actually more advantageous to put any additional money beyond your monthly mortgage payment towards your investing. Why? Because again, you could be making more money by investing, but also, let’s say hypothetically, you do wait until your mortgage is paid off.

Well, if your mortgage is a 30-year mortgage and let’s say you do pay it off early, let’s say you even cut it in half, which is an incredible accomplishment, right? Let’s say that you pay off your mortgage in 15 years and then you start investing. Well, guess what? You can’t get those 15 years back. And as we know from previous episodes of the show, time is way more important than the amount of money when it comes to investing. So you’ve just waited 15 years to start allowing compound interest to work harder for you.

And what happens with Dave Ramsey in particular and this mindset that all debt is bad and must be gone immediately and that you got to pay off your debt as quickly as possible is that it costs you actually a more fruitful, stable retirement. It costs you mental stability and peace of mind. This person is mentioning that she feels this weird emotional pull to pay off your mortgage. That’s not a fucking accident.

That’s like Dave Ramsey 101 shit, which is shaming you for having debt and making it your number one priority in your mind as opposed to actually crunching the numbers and being realistic about how life works. Let’s say you’re lucky enough to buy a house at 25. And then again, we pay off our mortgage 15 years early. Well, now we’re 40 years old before we even think about prioritizing investing. That’s not a great experience. And then let’s say that we prioritize investing after our 30-year mortgage.

Let’s say that we’re not able to pay it off early. Well, then we’re looking at you being 55 by the time you’re saving. The average retirement age in this country is 57 to 65, in that range. So we’ve literally done the math. We have a graph that I show you in the Stock Market Secrets workshop that demonstrates that the math works, the psychology works, the you protecting yourself for retirement works. So yes, continue paying your monthly payments. We’re not defaulting on our payments to do this.

But with your additional money as opposed to chipping away at your mortgage faster, it will probably mathematically make more sense for you to actually contribute towards your retirement, towards investing instead. So to this person who’s asking, should I pay down my mortgage faster or should I invest, you know the answer. It sounds like in this post you know the answer, but the little Dave Ramsey devil is on your shoulder being like, “Nah, you got to pay off your debt first.”

So investing is the right move here. All right, let’s take our second question. This is from our podcast community in a voicemail from Emily.


Hi, Tori. Thank you guys so much for all you’re doing. I have a really possibly dumb question, what does retirement actually look like logistically when you’re trying to take the money, when you’re at the stage of taking the money out of your IRA accounts? And are you having to sell all those stocks all at once and then you get that money and you get it in distributions, or you’re doing it a little bit at a time? And if that is the case, what if the market is really bad at the time that you’re retiring?

Let’s say if somebody was trying to retire like tomorrow and the market is super low and you have to sell all these stocks in there. So if you could provide a little bit more clarification on what the logistics will look like post-retirement and how you would actually pull your money out of those funds once they’ve grown and sat in those accounts for a while, that would be super awesome and helpful. Thank you so much.

Tor Dunlap:

I appreciated with Emily’s voicemail that I think we heard some wind chimes in the back and it was very ASMR soothing. I don’t know, I just really appreciated that. Okay, Emily, this is a question we get a lot, a question that we have answered in a full workshop in Stock Market School. So I’ll give you the TLDR. If you are anticipating retiring soon, this is not the time to start planning for how you’re actually going to use this money.

What I mean is if you’re 64 and expecting to retire at 65 with some money in your retirement accounts, that’s not the time to start thinking about, “Oh, I’m going to need this money tomorrow.” We’re going to backtrack a little bit. And if you can, we’re going to start thinking about you needing this money five to 10 years before you actually need it. I’ll give you the example of my parents. My parents are in their early 60s.

And for the past couple years, what they’ve been doing is slowly taking out money from their retirement accounts and from their general brokerage account, which as a reminder is not a retirement focused account, but is an investing account, and they’ve been putting it in what’s called a CD ladder. What is a CD ladder? It is various CDs with various terms, like year amounts.

So for instance, they might have one CD that matures, for instance, 10 years from now, and then they’ll have another CD that matures eight years from now, and then five, and then four, and then two, and then one, so that they’re slowly getting that money as they will need it. You are not taking all of your money out of your investing accounts for retirement at once. One, that’s going to be a tax nightmare. And two, the point is you want to allow your money to continue to grow, the money you don’t need yet.

So if you spend let’s say $50,000 a year, if your expenses every year are $50,000, maybe the time you’re thinking about retirement and those maybe five years before you’re slowly starting to pull out that money. If we’re retiring at 65, at 58, you might take out 50K. And then when you’re 59, you might take out another 50K, and then another 50K. You’re not taking out this whole lump sum of money at one time, but you’re moving it instead to places where your money is safe and at a less high of a risk.

You mentioned in your voicemail like, oh my God, what if I am taking out my money for retirement but the stock market isn’t performing well during that time? This is why we’re slowly taking out our money in anticipation of needing it to protect it in places that aren’t the stock market. Hence, a CD. And again, as a reminder, a CD, we’ve talked about this before, is a certificate of deposit. It’s like a souped up savings account. It is holding your money for a period of time. And in exchange for you not being able to access your money, you’re getting a higher percent interest rate.

So that’s one strategy that you can employ. My parents have done that, again, a CD ladder, and just being more strategic about when you’re taking out your money and how you’re using it. So the biggest thing to think about to your question is, one, no, you’re not taking out all of the money at one time. That, again, would be a nightmare in terms of managing it. But two, you want your investments to continue to grow, as well as during retirement season, let’s call it, you don’t want to hypothetically start planning for your retirement like six months before you’re set to retire.

This is something we want to think about in anticipation of retiring, and this is the perfect time, just like any time, to sit down and make sure that you are setting yourself up for success, not just right now financially, but in the future. So this is why my parents have done something like slowly siphon their money out of retirement accounts in order to protect it in lower risk or really no risk savings accounts. And the thing that they’ve done, because if you know a bit about retirement accounts, you might be asking yourself, well, how did they do that without paying a penalty?

How can you start withdrawing money out of a Roth IRA, for instance, without paying a penalty? Fun fact, you can take your Roth IRA contributions out penalty free. So your $6,500 that you’ve contributed year over year, and it’s been different depending on the year, but that contribution that you’ve made, you can take out penalty free. So that’s part of what my parents have done is take out their contributions, but not their earnings of their Roth IRA early so that they don’t have to take a penalty.

But it’s only if you’re under age 59 and a half that you have to pay a penalty for withdrawing your earnings. So if you’re over that age, my parents are now over that age, they can start taking even more money out of their Roth IRA. That might be an option for you. This is all in the weeds, right? But if you are somebody who’s trying to plan for early retirement, you are somebody who’s trying to help an older family member, or you maybe are an older listener to the show, then this is a just general piece of potential guidance.

But you got to figure out what’s right for you. You got to make sure that this works for you. And I’ll also say too, we have had so many conversations in Stock Market School about how do I stop working as soon as possible? And these are those strategies that are, again, slightly more complicated because they are more strategic. They’re kind of in a positive way gaming the system that exists so that you can say fuck off to your work life forever and retire. So yeah, that is my answer to that question.

You’re not taking all the money out at once. You’re being more strategic about it. And if you can, plan ahead. We’re talking years, if not a decade. That can be really, really helpful for you in strategizing your future retirement. All right, let’s take our next question.


Hi, Tori. A few months ago, I quit an incredibly toxic job that was severely impacting my mental health and my well-being, and recently I got a new job, which has been such a welcome change in terms of work culture and having a kind and empathetic manager. And I even managed to negotiate my salary to get 3,000 more than the job offer. Now that I’ve settled in at my new job, I’m wondering what I should do with my old 403(b) retirement account from my former job.

The account is currently managed by Vanguard. Should I leave those funds with my former employer, transfer it to a 403(b) account with my new employer, transfer it into a Roth IRA, or something else? I don’t particularly like the idea of leaving that money with my former employer, but I want to figure out what would be most beneficial for those funds. Thanks for all your help, Tori.

Tor Dunlap:

All right, first of all, congratulations are in order in two regards. One, you left that toxic job, baby. We got to love it. I just love that you decided, I don’t want to do this anymore, and then you negotiated and found yourself a better opportunity somewhere else. Double win for you of getting out of a bad situation and then putting yourself in a really good spot. So congratulations. All right, let’s talk about rolling over your 401(k). You’re 100% right. Your impulse is 100% right. We are not leaving our money with an old employer.

That is leaving money with an ex-boyfriend. I don’t trust my ex-boyfriend with my money. No, thank you. I don’t know what he’s going to fucking do with it. No. The reason we don’t want that to happen is, I mean many, one, we don’t know what the employer’s going to do with it. It’s your money, let me be clear, but they might switch 401(k) providers. And because you don’t work there anymore, of course, you might not know that they’re switching 401(k) providers. And then when you do go and try to find the money in a couple of years, you’re like, I don’t know where the fuck it is.

Two, it’s just you’re not going to remember your log-in. You’re going to have to manage a bunch of different accounts from a bunch of different past employers and that’s going to be a headache. We do want to consolidate. We do want to get your money out of your old employer. And we have two options, just like you said. We can either put it in our current retirement account offered by your employer. But if you don’t have a retirement account offered by your employer, you can roll it into a Roth IRA and that does not count for your Roth IRA contributions for that year.

So again, Roth IRA contributions for this year are $6,500. If you roll a 401(k) into that Roth IRA or into a general IRA, you are not contributing. That doesn’t count towards that $6,500 contribution. I will shamelessly plug. We have a partner tool that we use and recommend and love called Capitalize. They will literally do this for you for free. So if you are the person that’s listening and going, “I forgot to do that, or I have been meaning to do that and I don’t remember my log-in, and I don’t even know where the 401(k) lives, and I’ve been stressed about it, but I have just not looked at it,” well, cool.

Capitalize can help. We will put the link down below. Again, it’s entirely free. They will help you find your 401(k) if you’ve lost it, and then also help you roll it into an IRA. So Victoria, you have two basic options. Like I said before, the nice thing about rolling it over into a Roth IRA is you own the Roth IRA. You are the Roth IRA owner. It’s not associated with any employer. So you have more control over how you invest the money, where you invest the money. So that might be your better option.

However, either option is great. Just get it out of your ex-boyfriend’s house, get it out of your ex-employer. Make sure it doesn’t live there. And if you are somebody who’s listening who’s been meaning to do that, Capitalize might be able to help if you, again, don’t know how to do that whole process. So yeah, don’t leave it with your former employer. Let’s roll it over either into an IRA that we have, that we own, or into our current employer sponsored retirement account. All right, we talked about this before, Edward Jones, they’re on my hit list.

This is probably going to turn into a rant about Edward Jones, but this person is asking, “Hey, Tori. I’ve heard your episode, how the fuck do I get out of this hellscape that is Edward Jones.” So let’s go ahead and take a listen.

Speaker 1:

Hi, Tori. I have bounced around from one financial advisor that was trying to sell me whole life insurance to a new one with Edward Jones, but recently I don’t really want to be with them either. How do I switch to more of a robo-based investing or investing on my own from my current investments? How do I get my money out of there? How do I leave them? Or do I just leave it there and start my own thing and stop giving them my money every month? I love to have direction.

Tor Dunlap:

Oh boy! Okay, I’m taking deep breaths here because I just fucking hate Edward Jones. Sure. I’m going to go on the rant first, and then I’ll give you the advice. Edward Jones is bad. In case you didn’t hear the previous episode where I was mad at them, they’re just a terrible company. They take so much of your hard-earned money in fees. All of these places have fees. Don’t get me wrong. It’s how they make money. It’s how they stay alive. That’s fine. But Edward Jones has the most ridiculous unfair fees at the highest percentages I think I’ve seen.

It’s so much bullshit. It’s so much bullshit. And I am just going to tell you, if you are currently investing in Edward Jones, of course, this isn’t your fault, nobody told you, it’s okay, but get the fuck out. Look at me, get the fuck out. They are spending so much of your hard-earned money not actually growing your wealth, but on making themselves money. Just get the hell out of there. They’re not good. For comparison’s sake, I literally in anticipation for this episode, because Kristen told me we had a fucking Edward Jones question, I pulled up Edward Jones’ what they call schedule of fees.

This is easily Googleable. You can Google Edward Jones fees and find the same spreadsheet. They want to charge you for anything and everything. And it’s not like $2, it’s like 2%, which doesn’t sound like a lot. You’re thinking, 2%, that’s not anything. One, no other companies charge fucking 2% for this thing or for anything. And then the thing is, 2% of a million dollars, because we hope we’re all fucking millionaires, is a lot of money to just keep your account open.

So I just implore you so strongly that if you inherited an Edward Jones account, if you’re at Edward Jones because somebody told you like, “Oh, this is the place to go,” just get the fuck out. And then if you Google Edward Jones scam, you can get all this information as well. I’m not the only person saying this. Any good finance expert will also tell you the same thing. Okay, let’s talk about how we actually get out.

Fun fact, Edward Jones, because they have to squeeze the lemon that is you right before you leave, they’re like, “Let me get one little last drop out of this lemon,” they charge you a fucking closing fee. They charge you a fee for you to close your account. It’s a bullshit fee, but it’s worth paying so that we don’t have to deal with them anymore. You will pay a $95, most likely $95, exit fee. That is that last little squeeze the lemon juice on your way out. This is a transfer of an account fee.

So if you are trying to close out your account at Edward Jones and transfer it to somebody else, they’re going to get you on the way out. Now, if I was in your shoes, I might tell you with any other place that you don’t like, yeah, it’s fine. Keep it open. Just start investing somewhere else and just leave that account for now. Because it’s fucking Edward Jones, if I was you, I would pay the fee, call it a loss, and transfer my money over. You have three basic options for where you can start investing next, for where you can close your account and transfer your Roth IRA or your individual brokerage account.

Your three options are as follows. One, you can DIY your own investments. We’ve talked about this on previous episodes, but DIY platforms include Fidelity, Charles Schwab, Vanguard. The pro to these platforms is that they’re way less in fees. All of these bullshit fees that Edward Jones charges you, any of those three companies that allow you to do it yourself are not charging you nearly as many fees and definitely not the bullshit fees. So that’s the pro. The con is that just as the name suggests, DIY, you have to do it yourself.

And for the average listener of this show, they don’t feel confident enough to do it for themselves, and that’s okay. If you’ve ever logged into one of these platforms and seen all the graphs and charts and tried to figure out how to actually invest, and you’ve been like, “Holy shit, this is so confusing,” and then you’ve hit the bail button, you’ve just been like, bail, bail, bale, bail, then you know what I mean. So DIY platforms are great because they’re low fee, but you have to know what you’re doing.

You have to feel confident enough to manage your own investments and to make investment choices for yourself. I feel confident enough to do that. The average person completely understandably does not. So dear listener, that is probably not the best option for you. You mentioned robo-advisors. That is the other option. That is option number two. The great thing about robo-advisors is that you hand them your money and they ask you some information, your demographic information, your risk tolerance, when you’re expected to retire, and then they make choices for you.

They invest for you to depending on your answers. So that’s a great thing is you can get in and get investing quickly even if you have no idea what the fuck is going on. Some platforms that are robo-advisors, this is not an exhaustive list, but Ellevest, Acorns, Wealthfront, Wealthsimple, Betterment. There’s a bunch of other ones out there, but that’s an example of some of the robo-advisors. So the pro is that you’re investing quickly because they’re investing for you. The con, as you might imagine, is they’re going to take a small fee to do this.

Now, it is not an Edward Jones massive fee, but it’s somewhere between… Typically, it’s under like half a percent typically, which isn’t a lot, again, especially compared to Edward Jones, but that adds up. In addition, the thing we hear from our community a lot is that they are fishing for you rather than teaching you to fish. So someone might invest through an Ellevest or an Acorns or a Betterment, and they get cooking, which is great because we want to get started, but what happens is after a couple of years, they’ll come to me and they’ll go, “Tori, I don’t understand what’s happening though.

I don’t have any investing knowledge three years later than I did when I first got started. I don’t know why they’re choosing the things that they’re choosing. I don’t know what any of these terms mean still, and it’s my hard-earned money that’s just kind of like going into the ether and I’m crossing my fingers that people are making good choices with it.” So the pro of the robo-advisor, again, is that they’re getting you started fast, but the con is that they’re doing it for you and they’re taking a fee and you’re kind of left going, “Wait, what the fuck is going on?”

So call me the Hannah Montana of investing because I built you the best of both worlds. You get it? You get it? We built Stock Market School with you in mind. We literally teach you and guide you through DIY-ing your own investments in a safe place so that you can actually know what the hell is going on without the shame, without the jargon, and in a place where you can not only actually invest, but learn how to invest, get your questions answered, learn from me in coaching and in workshops and all of that.

All of the information can be found below, including pricing, including testimonials, FAQs. But we literally built Stock Market School with the Her First $100K community in mind, because frankly, we didn’t like any of the options that were out there. You can manage your money yourself. We’ve talked about this before. You don’t need a Wall Street chat, and yes, this includes Edward Jones in this case, to come and save you. You just need somebody to guide you and support you and give you the information that you need to make smart, educated choices.

So we would love to see you in Stock Market School if that’s of interest, but those are your options in terms of getting out of Edward Jones. Again, if I was you, I would pay, suck it up and pay that $95 fee to get out, and then move my money to either a DIY platform if I feel confident enough to manage my own investments, to a robo-advisor if I want to get started, or to Stock Market School and I would love to see you there. So those are your three basic options for actually moving that money out of Edward Jones.

I will round out this by saying, again, if you are at Edward Jones, they are scamming you. They are taking your money for things and for fees that don’t exist at most other companies. They’re just making them up, and that’s some bullshit. And we want your hard-earned money to actually go towards building your wealth, which is why the money’s there. Thank you so much for all of your questions about investing. As always, we have both free and paid resources around learning to invest that we will link in the show notes if you want to take your investing education further past this episode.

Thank you to everybody who submitted their questions. You can always leave us a voicemail and we might feature it in another Ask Tori in the future. We appreciate you being here. We’re so excited to watch you fucking build your wealth and grow it by investing. I hope you have a great rest of your week, and we’ll talk to you soon. Thank you for listening to Financial Feminist, a Her First $100K podcast. Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields. Associate producer Tamisha Grant.

Marketing and administration by Karina Patel, Sophia Cohen, Kahlil Dumas, Elizabeth McCumber, Beth Bowen, Amanda Leffew, Masha Bachmetyeva, Kailyn Sprinkle, Sumaya Mulla-Carillo, and Harvey Carlson. Researched by Ariel Johnson. Audio Engineering by Alyssa Midcalf. Promotional graphics by Mary Stratton. Photography by Sarah Wolfe, and theme Music by Jonah Cohen Sound.

A huge thanks to the entire Her First $100K team and community for supporting the show. For more information about Financial Feminist, Her First $100K or guests and episode show notes, visit financialfeministpodcast.com.

Tori Dunlap

Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over one million women negotiate salary, pay off debt, build savings, and invest.

Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.

With a dedicated following of almost 250,000 on Instagram and more than 1.6 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”

An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.

Facebook Group