Q&A: Why Do I Still Feel Anxious When I’m Clearly Doing Well?

9 Jun 2026 · 50 min · 19 chapters

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In short

Q&A on (1) what to do with an extra $600/month from a side hustle using a goal-timeline approach, (2) why people feel anxious even when finances are on track, focusing on financial therapy, account-checking habits, and investment policy statements, and (3) an update on using short-term rentals for early retirement, including lessons from selling before Hurricane Helene.

Guests (callers)

  1. Caitlin (Portland, Oregon): W-2 household with mortgage at 2.6%, ~$400k in retirement, 3 months emergency fund, savings for vacations/car repairs/home maintenance, young kids (3.5-year-old and 1-year-old twins). Wants retirement in 20–22 years; side hustle adds ~$600/month pre-tax.
  2. Jane (Anonymous): Federal employee, ~$140k–$155k income, mandatory retirement at 57 (eligible at 53). ~$325k TSP (mostly Roth), ~$90k brokerage, ~$100k Roth IRA, ~$15k HSA. Constantly rechecks accounts despite deleting apps.
  3. Charlotte (update): Asked in Jan 2022 about STRs funding early retirement (target Dec 2025). Owned 2 STRs, sold in 2023; Hurricane Helene later devastated Chimney Rock/Lake Lure. Retiring June 30, 2025; slow travel planned.

Key claims & notable examples

  • “Timeline it”: fill short-term “potholes” (big expenses in next 5 years like car/trips/roof) and secure long-term by maxing retirement earlier.
  • Coast FI framing: fully funding retirement can eliminate the “retirement bill,” creating psychological relief.
  • Anxiety root: mandatory retirement at 57 may drive powerlessness fears; financial therapy helps unpack scarcity-based hypervigilance.
  • Behavioral triangle: thought/behavior/action—delete apps and set specific “check” days; worry can be redirected to improving an investment policy statement.
  • STR lesson: short-term rentals compete with hotels (Marriott/Hilton), not other landlords; avoid influencer/ego-driven decisions. Charlotte lost ~$80k but avoided prolonged unrentability and geographic concentration risk; properties survived the hurricane.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Listener Question about Extra Income

0:45 to 3:24

Caitlin asks about managing additional income from her side hustle.

“Financial psychology, increasing your income, investing, real estate, and entrepreneurship.”

Analyzing Financial Goals

3:24 to 5:12

Joe discusses how Caitlin can prioritize and analyze her financial goals.

“You were kind of laughing when you said it's going to get better.”

Three Strategies for Managing Extra Income

5:12 to 7:41

Joe shares three strategies for utilizing Caitlin's extra income effectively.

“So my mental framing, immediately it went to, all right, we've covered the basics.”

Benefits of Early Retirement Savings

7:41 to 9:32

Discussion on the psychological advantages of early retirement savings and Coast Fi.

“Is she ahead or is she behind on all those goals, just use a calculator, work with an hourly financial planner, do whatever she's going to do.”

Wrap-Up of Listener Question

9:32 to 14:05

Revisiting Caitlin's question and summarizing the advice given.

“retirement bill for the rest of your life, if you're maxing out your 401k, you've just freed up two grand a month.”

Wrap-Up of Listener Question

14:12 to 15:32

Revisiting Caitlin's question and summarizing the advice given.

“So they hit that trifecta of quality, affordability, and it's ethical.”

Wrap-Up of Listener Question

15:36 to 16:57

Revisiting Caitlin's question and summarizing the advice given.

“It's summer, so if you've got outdoor space, you want it to feel like you because you want to be out there as much as you can.”

Listener Question: Financial Anxiety

17:18 to 19:58

A listener shares their financial success but struggles with anxiety.

“I am employed with the federal government and I make between$140 ,000 and probably$155 ,000 a year.”

Exploring the Roots of Anxiety

19:59 to 21:06

Discussion on the psychological roots of financial worry.

“but I can hear the suffering in your voice.”

Character Analysis: Jane Eyre

21:07 to 23:48

Using Jane Eyre as a metaphor for addressing anxiety and worry.

“Like you spoiled the end of King Lear a few episodes ago.”
Show all 19 chapters

Worrying as a Natural Response

23:49 to 26:30

Discussion on how to manage worry rather than eliminate it.

“I did this a long time ago with a therapist.”

Creating an Investment Policy Statement

26:31 to 28:00

Advice on setting an investment policy to control financial anxiety.

“Ooh, so I disagree with you here, Joe, but please go on.”

Understanding Financial Anxiety

28:00 to 37:48

Explore the roots of financial anxiety and the importance of financial therapy.

“Instead of how can I check my numbers another time today when I know they're going to be okay.”

Understanding Financial Anxiety

37:55 to 39:58

Explore the roots of financial anxiety and the importance of financial therapy.

“Monarch is basically like having a financial advisor in your pocket.”

Understanding Financial Anxiety

40:04 to 41:38

Explore the roots of financial anxiety and the importance of financial therapy.

“There's always something you want to get better at.”

Charlotte's Journey with Short-Term Rentals

42:01 to 44:41

Learn about Charlotte's experiences and challenges with short-term rentals leading to her retirement.

“My first question aired on episode 352 way back in January 2022.”

The Distinction Between Rental Types

44:41 to 48:22

Understand the differences between short-term and long-term rentals and their market dynamics.

“And maybe I'll call you back in another four years to let you know how much fun we're having on our travels.”

Cognitive Biases in Real Estate Investing

48:22 to 53:33

Discover how emotional factors influence investment decisions and the importance of awareness.

“You don't realize just how fickle your audience is going to be.”

Embracing Slow Travel

53:45 to 54:57

Get insights into the concept of slow travel and its benefits for a richer life experience.

“That's affordanything.com slash mistakes.”
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Transcript

Automatic transcript. May contain errors.

0:00Joe, when you were a financial planner, did you ever have the issue that your clients, their financial plan is technically working, but emotionally it just doesn't feel secure?

0:10Paula Pant:All the time. How did you address that? We, well, why don't we get into that later? Oh, we're going to get into that in the middle question of today's episode. But first, we're going to address a question from someone who's wondering what to do with an extra$600 a month. And then we're going to talk to someone who is calling with an update. Sounds like an adventure. It is. Welcome to the Afford Anything podcast, the show that knows you can afford anything, but not everything. This show covers five pillars. Financial psychology, increasing your income, investing, real estate, and entrepreneurship.

0:51Acronym, double I FIRE. I'm your host, Paula Pant. I trained in economic reporting at Columbia. Every other episode-ish, I answer questions from you. And I do so with my buddy, the former financial planner, Joe Salcihai. What's up, Joe?

1:03Paula Pant:You know, I was out buying groceries this morning, and I realized that my wallet is just like an onion, Paula. It has many layers? Every time I open it, it makes me cry. Oh. Well, with that, we're going to go to our first question, which comes from Caitlin. Hi, Paula and Joe. This is Caitlin calling from Portland. Oregon. My question in a nutshell is what to do with slash how to think about the extra income I bring in through my side hustle. My husband and I both have stable W-2 jobs that cover all of our expenses and my side hustle brings in about an extra$600 a month before taxes. where should I put this money and how should I think about it?

1:52Paula Pant:For context, our long-term goal is to be saving for retirement. We plan to retire in about 20 to 22 years and we currently have just under 400k saved in various retirement accounts. And our short-term goal is to beef up our savings. We have about three months of expenses saved in our emergency fund. And then we have a couple of other savings accounts, one for vacations and another for car repairs and home maintenance. We also have put a little bit of money every month into our children's 529s and investment accounts for our kiddos. Also for context, our children are very young. We have a three and a half year old and one year old twins.

2:47Paula Pant:So I guess our other short term goal is just surviving this young child phase of life. And our expenses are going to go down dramatically when our children are no longer in daycare in a few years. So that will open up a bunch of money that we could then later be putting into retirement accounts and into our kiddos, five, two, nines. We also have no debt except for our mortgage, which is at a 2.6 % interest rate. So no debt to pay down. All right. I'd love to hear your thoughts. Thank you so much for your show. I appreciate all of your great advice. Caitlin, twins. I have twins. I'll foreshadow the future, Caitlin.

3:32Paula Pant:You were kind of laughing when you said it's going to get better. It gets so much better. it gets so much better when the twins went to kindergarten life was good no more child care oh my goodness my wallet was very happy my wallet was not like an onion then what's your wallet like then what makes you giggle like a i don't know laughing gas a cantaloupe a honey crisp apple i like those a lot okay so like a piece of fruit that sparks joy yes as opposed to a vegetable that makes you cry yes exactly this is an interesting problem paula because really you You know, the way I see it, there's three ways she can handle this.

4:08Interesting. Okay. I actually, and Joe, you and I did not discuss our answer beforehand. My mental model is not three potential solutions. My mental model right now is follow-up questions around goals. So I'm curious to hear what your three potential solutions are.

4:23Paula Pant:Well, to go where you're going, I think the important thing to do is exactly what I think you might be alluding to, which is I like the fact that she's timelined out her goals, right? She's looking at the goals. And for people that don't know my methodology, but you know very well, Paula, that's number one on my list. Timelining. Model it all up. Yep. Timeline it all up. Take a look at how the goals fight against each other. So what I'd like to know is how are you doing toward each of these goals? It sounds like you're doing great toward them. Yeah. So just on paper, it looks good, but I want to know, am I further ahead on this one than I am this one?

5:02Paula Pant:because the first way you can do things is just like fill it in potholes. Take the pothole, find out where the potholes are, fill those in. That's option number one. So my mental framing, immediately it went to, all right, we've covered the basics. No debt, emergency fund is good. There's some savings for college. There's good savings for retirement. There's savings for things like vehicle repairs, et cetera. where my brain went immediately is, all right, in the next, let's say five years, five years is a relatively short-term bucket. In the next five years, are there any major big ticket expenses that you are anticipating?

5:43For example, maybe you might be buying a car in the next five years and you might want to pay cash for that car. You might want to take some kind of a family trip in the next five years, some major family vacation. Maybe there's some renovation that you want to make on your home that might happen in the next five years. And maybe it's not even an aesthetic or cosmetic renovation. Maybe it's simply that the roof is 20 years old. Given the age of the roof, it likely will need to be replaced. My brain immediately went to likely big ticket expenses that could happen in the next five years.

6:21Paula Pant:And that for me was option number two, which is begin with the beginning of the timeline, right? Where am I at now? What are those first things that I'm looking at? And use the fact that you have this money coming in monthly to make sure that those aren't pitfalls anymore. Erase the pitfalls from the short term, which then you can guess where I'm going with the third one, which is - Is it the other end of the line? The end? Absolutely. Just go, you know what? I'm going to start with the end of my life and I'm just going to make sure that I am going to backfill. And so I get freedom from worry forever at an earlier age.

6:59Paula Pant:I may worry now and I may struggle a little bit now, but I'm going to make sure that when I'm, you know, let's say that she's fine at 62 now, now I'm fine at 61, then I'm fine at 60, then I'm fine at 59, 58. You kind of start this countdown going, which is cool because of gamification and also the$500 a month. $600 a month. The$600 a month. I almost shortchanged her. The$600 a month goes further because the return on that money, if we put it toward long-term goals, means it's easier to backfill that way. So of the three things, I would model it out no matter what and see where she's at with each stage of the timeline.

7:43Paula Pant:Is she ahead or is she behind on all those goals, just use a calculator, work with an hourly financial planner, do whatever she's going to do. Figure out where she's at with those. But my bias is secure the long-term. That is my bias as well. And the reason for that, Caitlin, is because it's twofold. Number one, there is a tremendous psychological advantage. We talk on this podcast about the concept of Coast Fi, which I guess everybody has their own semantic difference in what that means. But I define Coast Fi as the point at which your retirement accounts are well-funded enough that you don't have to save for retirement anymore.

8:27So if you think about the payment that you make into a retirement account as quote unquote a bill, the retirement bill that you're paying monthly is likely one of the biggest bills, if not the biggest bill, that a lot of people pay. If you are fully maxing out your 401k, if you're 49 and under, a full max out is$24 ,500 a year as of the 2026 contribution limits. That means you're spending more than$2 ,000 a month on your retirement quote unquote bill. And if you can eliminate that bill from your overhead, that creates a huge amount of breathing room when you no longer have to pay the 401k bill because you fully funded it out.

9:13That is what Coast Fi is, or at least that's how I define it. And there is a certain freedom that comes with knowing that you have eliminated the retirement bill forever. Even if you can't retire today, once you've eliminated needing to pay the retirement bill for the rest of your life, if you're maxing out your 401k, you've just freed up two grand a month. Yeah.

9:41Paula Pant:And I can't just stop thinking about too, how it's the easiest of the three. It's the easiest of the three approaches in terms of you have to dedicate less money to it. You have to dedicate fewer dollars per dollar that you're trying to, um, to get toward the goal because you're working on, on using that time advantage to your advantage. And the cool thing is, is I feel like, you know, once, uh, once diapers and daycare goes away, her short-term issues are going to be less four years from now anyway. So if she can just buckle up for the next four years and put this money toward long-term, it's going to get really rosy very quickly.

10:19Right. Joe, your twins are 31 now?

10:23Paula Pant:30. 30. Almost 31. Oh my goodness. They'll be 31 in the next couple of weeks. Ah, congratulations. How can they be 31 when I'm only 35? It's so weird. And Caitlin will like this. I'm sipping on coffee today, but look at, I've got one of the Columbia Valley's famous waterfall mugs. Oh, beautiful. I can never say the name of it. And everybody in the Portland area will be screaming at their device. Uh, Multnomah falls, I think Multnomah, maybe whatever I say at my friends from Portland always correct me. So it's a beautiful waterfall. Have you been here before No, I've been to the Portland area, but I've never been to that particular waterfall.

11:08Paula Pant:Beautiful. All the waterfalls along the Columbia River Gorge are just gorgeous. Great place to spend a lot of time. The gorge is gorgeous. Gorge is gorgeous. As is wine country. Let's just go to Portland. Forget it. Caitlin, we're coming to visit. All right, Caitlin. So there from Joe, those are your three options. And then from me, those are, I mean, really it's my mental framing echoed Joe, but coming at it from a different construct. I came at it from the next five years big ticket bucket, and then also the just max out retirement. You know, the earlier you can max out retirement, the better.

11:41And my bias does tend to go towards maxing out retirement for the same reason that you echoed Joe, because the younger you are, and you will never be younger than you are today, every dollar that you put in there goes so much further. Joe's laughing at me now.

12:00Paula Pant:You heard it here first, everyone. You will never be younger than you are today. Well, no, I say that because sometimes when I say the younger you are, people get disheartened because they're like, well, I'm not young anymore. Oh yeah. Right. You know, exactly. And so I want to make the point that yes, you still are young as a relative term. And so an older version of you is going to look back on the you of 2026 and think, wow, I was so young back then. Every day you wait is a mistake. Right, exactly. See, there's a method. It was better than the first blush. I was like, wow, that should go on a book cover.

12:38Paula Pant:That's deep. Well, thank you, Caitlin, for the question. And congratulations on the great management that you're doing of your family finances. We're going to take a moment to hear from the sponsors who make the show possible. When we return, we are going to address that opening question. What happens when your financial plan is technically working, but emotionally it feels scary still? So how do you address that? We're going to tackle that one right after this. In business, there's no room for guesswork. Every shipment matters. Every deadline counts. When you're trying to keep operations running smoothly, the last thing you need is uncertainty.

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17:15Welcome back. Our next question comes from Anonymous.

17:21Paula Pant:Hi, Paula and Jo. Thank you for taking my call. I am going to soon be 37 years old. I am employed with the federal government and I make between$140 ,000 and probably$155 ,000 a year. I am eligible to retire at 53 years old, but I'll be required to retire at 57 years old. I'll have a pension and social security. And then as far as my investments go, I have about$325 ,000 in a thrift savings plan, a TSP, which is equivalent to a 401k. That is mostly invested in a Roth account. Then I have about$90 ,000 in a brokerage and$100 ,000 in a Roth IRA. and both of those follow the Paul Merriman's Four Fund portfolio.

18:18Paula Pant:And then I also have about$15 ,000 in a HSA through Fidelity that's invested. So I'm doing all right. I know that. But what I struggle with is I constantly check accounts. I constantly will run my numbers. I do spend money on things that are important to me, like international travel and domestic travel to see friends and family. I can't seem to find peace when it comes to my accounts. And it's the same thing every year. I know what I'll need to set my contributions for to max my TSP and to max my IRA and to max my HSA and to balance out my brokerage accounts and whatnot. It's a lot of money that I'm investing and I'm proud of myself for that.

19:14And I have recently deleted my apps temporarily, so I'm not checking them constantly,

19:21Paula Pant:but I do download them back in order to invest. My question is, I'm trying to understand why I feel so neurotic running calculations and checking accounts and how can I find more peace while still sticking to a journey that I'll be on for a while. Anonymous, thank you for the question. I can hear the struggle in your voice. It's actually really heartbreaking to hear your question because you are doing so well, and yet I can hear how much suffering, and I don't use that word lightly, but I can hear the suffering in your voice. I can hear the struggle. So let's talk through what might be at the root of it.

20:09And then let's talk through a few tactics that might help address it. Oh, we've got more important things to do than that.

20:17Paula Pant:Are we going to give her a name? We need to. We want to be called anonymous their whole life on this show. I was thinking during her discussion, who is a character from literature? who worried a lot, but came out fantastic. Things went really well. One of my favorite books was Jane Eyre. And I think that the character in Charlotte Bronte's book, Jane Eyre, Jane, I think Jane is this person. I think Jane ends up in this very, very good place at the end of the book, even though all the way through the book, she's very worried and rightfully so. I won't spoil what happens in Jane Eyre for people who haven't read it, but it's well worth reading.

21:12Like you spoiled the end of King Lear a few episodes ago.

21:16Paula Pant:Well, if you haven't read King Lear. You had 400 years. It's on you. I should probably say that about Jane Eyre as well. We probably had enough time, but anyway, I thought we could call her Jane. Perfect. I love it. Jane, thank you for the call. There are a few things that I think might be happening. Number one, my ears perked up right away when you said that there's mandatory retirement at age 57. The reason that stood out to me is, you know, it's one thing when retirement is voluntary. A lot of people listening to this are eager for a voluntary retirement, But there is a world of difference between a voluntary and a mandatory one.

21:59To have a mandate that one must retire, A, there's a bit of powerlessness there, that no matter what is happening in your life and no matter how good of a performer you are at work and no matter what is happening in the broader economy, based on no other factors beyond your age alone. You must retire. That's a very different scenario. And knowing that there is a lot of age discrimination against older workers in the workforce and being 57 and then going out and trying to get a job at the age of 57 is nothing like getting a job at the age of 37. And even that, people struggle to get to find work at age 37.

22:49You think about how much harder it would be 20 years in the future. I would guess, or I would at least offer the hypothesis that that might be contributing to some of the worry.

Read the full transcript

23:04Paula Pant:My reaction, Jane, to your question was, I can have a lot of conjecture as to why you're worried, but I think that that's going to be the key to your success. What's the deep down reason that you feel the need to continually rerun the numbers and recheck? An emerging field, which is a great field and has been necessary for a long time is - Financial therapy. Financial therapy. I'm sorry. Sorry, I stole your punchline. But it is, Paula. And I think that this could be a good insurance policy. And just having somebody to walk through this, who's a trained professional to walk through what the deep-seated feeling is.

23:54Paula Pant:I did this a long time ago with a therapist. It was pretty wild, Paula. Mine was around eating. And what was wild was that my desire to eat fast food, why did I have a desire? I know that the nutritional value is crap. I know that it's doing nothing for me. And at the time, I was much more of an athlete then than I am now, but still I was fighting this, what felt like an uphill battle. And I ended up talking to somebody about it. And after a series of sessions, we realized that my love of fast food went way back to the time when I was a kid and my mom would put my brother and I in the car. We would meet my dad for his lunch break at General Motors.

24:40Paula Pant:My dad didn't have a lot of time. So we would go to this fast food place called Dog and Suds, where we would eat hot dogs and fries and root beers. And so in my head, deep, deep down, Paula, I equate fast food with warm, fuzzy family love feelings. That is a lie. There is nothing truthful at all about that. But it took us several sessions and then it hit me like a ton of bricks. I get a warm, fuzzy every time I pull into a drive-thru because of this childhood memory. So wait. So when you say that is a lie, what you mean is the equation is not objectively real, but it is subjectively truthful. Exactly.

25:25Paula Pant:Fast food does not equal love. Right. That Big Mac is not going to love me back. And it's funny, even now I still fight it. I fight it very well, but I still fight it. I'm very happy when friends come to town and we get to go to TLC a burger place downtown. Oh, is that the place that we, you and I went? That's the iconic place that you and I went. Oh, that place is great. Yeah. Yeah. You know, those travel guys, Jason. Yeah, yeah, yeah. Yes. Yes. He came to Texarkana and went to TLC and it was incredible. But anyway, that's, that's neither here nor there. I still like looking for a fast food recommendation in Texarkana, Texas.

26:03Paula Pant:Yes. You just got one. I still love a good hamburger, but I know that part of that feeling is an emotional reaction. So I think there's that, but I also think this, I think that Paula and I telling Jane to stop worrying, or if anybody tells you to not worry, or, you know, I think even deleting your apps is you telling yourself, I shouldn't be so worried. I think that's fighting your nature. And I think that's a waste of time. Ooh, so I disagree with you here, Joe, but please go on. I think it's this, when I had clients that were worriers, me telling them not to worry or me trying to say worry less or it's going to be okay, wasn't a fix.

26:48Paula Pant:There were a couple of things that were a fix. If you're a worrier naturally, if we can take that worry and we can assign it a task that is much more useful, then I think that we might be able to marry some of the emotional piece of our humanity with the logical piece of our humanity. This is where an investment policy statement really helps. Because if you set yourself an investment policy statement that says, I am going to check my accounts on this day and this day, and for you running your numbers is an issue. I am going to run my numbers on this day, this day, this day, and this day. And you make that your investment policy.

27:38Paula Pant:And then instead of going to check your accounts every day, you're tweaking your investment policy statement. If you think your investment policy statement's not right, or you're obsessing about the fact that my investment policy statement, how can I make it better? I think, how can I make my investment policy statement better? How can I make the machine operate better, work more in my favor? That's a kick-ass thing to worry about. That's a fine thing to worry about. Instead of how can I check my numbers another time today when I know they're going to be okay. I like where you're going with that.

28:16Although we also don't want Jane to get into a habit of constantly tweaking and updating the policy statement.

28:22Paula Pant:But I don't think you do. I don't think that's the outcome. I've never had that be the outcome. Okay. But to your earlier point, Joe, about how you think that where I disagree with you is your earlier statement around deleting the apps might not work or deleting the apps might be the wrong approach. I think deleting the apps is enormously important and keeping them deleted is tremendously important. And I think that because of, you imagine a triangle, right? And the three points on the triangle are thought, behavior, and action. These three things as the three points of a triangle all influence one another.

29:01Your thoughts and feelings influence your actions, but also your actions influence your thoughts and feelings. Like each point of this triangle, they influence the other two. And so if she takes the action of deleting the apps and keeping them deleted, and instead of when she needs to make new contributions, do it on a laptop or a desktop monitor, do it on a website, not on an app. That action can eliminate some of the subsequent thoughts and behaviors that it influences because the apps are designed for constant checking and constant checking fuels a certain neuroticism. It fuels a certain worry.

29:51That's what apps do. So use behavioral modifications You know, use changing action as a method of changing thoughts and feelings. In other words, act first and the feelings will eventually catch up with it.

30:08Paula Pant:Maybe. I feel like that's still a leaf versus the root of the tree. I agree. The root of the tree is understanding what anxieties or traumas fuel a scarcity mindset, because oftentimes financial anxiety comes from a fear of not having enough. And that fear of not having enough often comes from some experience or experiences that we have had in the past, or that we have seen other people have. And that's where those roots are. And I agree, that is what a financial therapist can help unpack. And by the way, the reason that we talk about financial therapy specifically and not just therapy in general is because there are many therapists who are not trained to talk about money and who, in fact, they themselves may have their own hangups about money and they have little to no training as to how to help people with their money, which is insane if you think about it, because you think about the number of marriages that crumble due to financial arguments.

31:15You think about the fact that so many Americans report that one of their top three stressors is money. It's actually rather silly that the field of psychology has been so slow to catch up to the emotional relationship that humans have with money, but that's how the field has developed. And that's the reason why the nascent field of financial therapy, specifically financial therapy, people who are trained in that niche, that particular niche, that is the reason that that is so important. And AI can never replace a human, but AI can be a complement.

32:00Paula Pant:I definitely am not against deleting the app. I think my bigger point was that that's not where my focus would be. It would definitely be on the financial therapy piece. I think that's a far more important thing to solve. And I'm excited for her because I think Jane's doing such a great job of saving that if she's able to explore that and really get some leverage on that feeling, I know having been through it with my fast food thing, Paula, it's pretty empowering to get beyond it because my gut reaction still is, oh, that just sounds so warm, fuzzy. And then immediately my conscious brain goes, yeah, it's not, it isn't.

32:49And so then if you think back to that triangle, because Joe, what I hear you say is your conscious brain, you know, the cognitive override to the feeling. So if you go back to the triangle, the action modification, so deleting apps, for example, or heck, if you find yourself overchecking websites, you might block certain websites from yourself or give yourself permission to only access certain websites at certain times, right? That's the action part of the triangle. And then the thought part of the triangle is learning specific phrases that can be the cognitive override. And then the feeling part of the triangle is financial therapy.

33:30And so those cover the three points of the triangle.

33:33Paula Pant:It's a great question. And by the way, the fact that Jane, you asked this question, there are so many people that are afraid to ask this question. Yeah. Yeah. Thank you for asking. Yeah. The fact that you did was pretty, it's pretty kick-ass yeah because so much of our relationship with money it is a a deeply emotional relationship i went from being an okay financial planner to i think a really good financial planner sounds like i'm talking i'm pat myself on the back but i think that i was a really good financial planner because I started focusing on this stuff. And I found that this is what my clients needed was much more the behavioral aspects, the emotional aspects of their money.

34:24Paula Pant:We started focusing on timelining out the goal, the goal attainment. How do I feel about these goals versus each other? The value, you know, the values, maybe this is why I'm so attracted to Vicki Robbins' work, the value that we place. Are we spending our dollars on things that we value? And I think it isn't just money. I mean, you mentioned Spark Joy earlier. I think it's the magic of Marie Kondo. I mean, it's organizing for God's sakes. What about Sparking Joy? But I think that when we solve for happiness, when we begin solving for happiness, like good things happen, whether it's cleaning out the closet or how we work with our money.

35:06Yeah. I think a lot of us are driven by the fear of not having enough. And oftentimes, if in our early life, we didn't have enough or felt as though we didn't have enough, those imprints last regardless of the present day value of our portfolio. The key is to notice them and not be ruled by them. So Joe, I think your analogy with food is a good one because in the same way we have a deeply emotional relationship with food, that's exactly what the relationship with money is. Driven much more by fear and joy than by objectivity. So Jane, I hope we gave you some food for thought. Pardon the pun. Oh, I see what you did there.

35:54Yeah, couldn't resist. I'm going to link in the show notes to a couple of episodes that we've done with Dr. Brad Klontz. He is one of many financial therapists, and there's some fantastic ones out there. But he shares insights into things like money vigilance or money hypervigilance, which you've described, money anxiety, some of the things that can really affect us. So we'll put those links in the show notes. I'll also link to an episode. It was an interview that I did on Emma Chamberlain's podcast that was about the same topic. We'll link to that in the show notes as well. That's some good further listening.

36:40So thank you, Jane, for the question. And please call us back and give us an update on how this all unfolds and what progress you've made over the span of that year. We're going to take one final break to hear from the sponsors who make the show possible. When we return, speaking of people who call us back, we are going to hear from someone whose question originally aired in January 2022. At that time, she called to ask whether or not short-term rentals could fund their early retirement. And well, you'll hear how things have unfolded since then over the span of the last four years. It's the start of summer.

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41:52Welcome back. Our final question today comes from Charlotte.

41:57Paula Pant:Hi, Paula and Joe. This is Charlotte calling with an update. My first question aired on episode 352 way back in January 2022. In it, I asked about short-term rentals funding our early retirement, which was slated for December 2025. At the time I called, we owned one STR and were looking to grow our portfolio to three or four. We ended up purchasing STR number two in March 2022. I was totally caught up in the Airbnb post-COVID craze, and our first property had really been a unicorn. We bought it low, it stayed booked, and it made us lots of money. The second property was the opposite. We paid too much for it, put too much into renovating it, and when it still wasn't performing like we had projected by the summer of 2023, we re-evaluated.

42:58Paula Pant:Poor performance, plus the sheer number of hours and attention it took to manage two short-term rental properties, from afar convinced us to sell both in the summer and fall of 2023. We never could have expected that the following year, fall of 2024, a hurricane would come through and wipe out the town in which both of these properties stood. Hurricane Helene devastated Chimney Rock and Lake Lure, North Carolina in one fell swoop. Both properties survived the hurricane, but would have been unrentable for 8 to 12 months following, and the town of Chimney Rock was effectively wiped off the map. I'm so grateful that we sold when we did, even though it was a hit to the ego, and we ended up losing about$80 ,000.

43:48Paula Pant:dollars. I'm also so grateful for the new owners that the properties survived. So many did not. The good news, we did not fire in 2025, but we are just now six days away from retiring as of today. We will leave home to start slow traveling on June 30th, but don't worry, Joe, we have a backup plan if we don't love it. And we're approaching all of it with a beginner's mindset. I'd imagine if I had had Paula's rental course, not a paid advertisement, we could have avoided the mistakes that we made with these rental properties. If anyone takes something away from my story, please buy the right way, not with emotion and not because some influencer on YouTube told you it was a sure thing.

44:39Paula Pant:Thank you so much for all that you both do. And maybe I'll call you back in another four years to let you know how much fun we're having on our travels. Amazing. Congratulations. I love this. Wow. Charlotte, thank you so much for the update. Congratulations. And of course, by the time this airs, you will have fired. You will be in this new phase of life and you'll be about to start some beautiful slow travel. You know what that means? They need to come to Texarkana. They have to. Yeah, that's right. There's a, what is it called? TLC, that fast food place in Texarkana. Yeah. Yes. I'm always up for a hamburger.

45:22Paula Pant:It isn't love, but I can still figure out a way. There is so much going on here. I love that she identified that, you know, I think a lot of the time when people begin thinking through their portfolio, getting into real estate. This is my experience. Getting into real estate just seems obvious, sounds easy, and it's not. It truly is not. And because there's so many charlatans out there, Paula, who are telling you that it's easy and that, oh, you should do this. I saw somebody just last week again saying, hey, you know what you should do? forget investing in your 401k, you should flip houses. Are you kidding me?

46:05Paula Pant:Like if all the ways to buy real estate, let's pick the most time intensive one. That's more like a job than any other one. Like if you're going to buy real estate, flipping houses is the last thing you want to do. Yeah. You need a good team of people that you, you have to have a machine. It's, it's so much like it. It's so frustrating. So flipping is a full-time job for sure. Yeah. Again, not a paid advertisement for your course or for any course, but learn what you're doing. If you're going to do something as specific as buying a piece of property or two pieces of property, or, you know, she went from three pieces of property that she wanted to zero.

46:44Charlotte, your experience also highlights, and this is a lesson that I want the wider audience to take away the distinction between a short-term rental versus a medium to long-term rental. Actually, I'll put those in three separate buckets because a medium-term rental is its own bucket, but each is distinct. And the reason my instinct was to immediately put medium and long-term rentals in at least under a similar branch of buckets is because those two are medium-term or long-term are both a bit more akin to owning a commodity, whereas short-term rentals, as you know very well, Charlotte, short-term rentals are akin to being in the hospitality industry.

47:34As a short-term rental owner, your competition is Hilton, Marriott, Sheraton, Hampton Inn, right? Your competition are hotels, and that's very different from long-term rental properties where your competition is other landlords. So even though the underlying asset is the same, you know, the use of a residence, one thing that I hope that everyone who's listening to this understands is that despite that underlying asset being the same, that can create a false sense that that means that short-term rental and long-term rental are comparable when in fact they are two completely different fields.

48:20Paula Pant:I get people first get into short-term rentals. You don't realize just how fickle your audience is going to be. And the fact that you are, Paula, in people's mind, you're competing against Marriott. I know people don't think they are like, no, no, no. Yes, you are. Increasingly, I feel like the quote, you know, started off as couch surfing in the sharing economy. It's not that at all. People are going to Airbnb because they want a Marriott experience. And if you're not willing to be able to provide that, or you even thought through the systems to provide that, you're going to get a few bad reviews.

48:53Paula Pant:And when you get the bad reviews, that's a death knell to your short-term rental. Well, and now there are also major companies that are in the short-term rental business and they have economies of scale. Yeah, exactly. So it's nothing like what it was. Medium-term rentals, I won't go down that rabbit hole right now, but there's a lot of opportunity there for the people who are interested in that. We will table that discussion for a different day. But if you're interested, go back and listen to our interview with Jeff Hurst, because there's an opening in the economy right now in that space. All of that said, Charlotte, I want to highlight a couple of things that you've done really well for the sake of illuminating that to the rest of this community.

49:41You talked about the importance of not letting sunk cost, not letting ego, not even letting loss aversion drive your decision-making. So you overcame a lot of cognitive biases that trip people up, right? That is a hallmark of good investing. You said, who cares about sunk cost? Who cares about loss aversion? Who cares about ego? I'm going to make the best decision that I can based on present day data. And that was what you did. And that is what a good investor does. But it is also, you know, we were just talking about how in the previous question, we were talking about how money can be a very emotional topic.

50:27That is something that is very difficult to do. So I want to applaud you for not letting sunk cost and ego and loss aversion get in the way.

50:36Paula Pant:I know that you and I I both talked to Claire Flynn Levy about stock market maestros. And what strikes me is how similar the behavior of a great investor was with what Charlotte did, Paula. To your point, the best investors, one great trade of a great investor is they're willing to say, I didn't make the right call, that the call was bad. And instead of holding onto it and letting your, again, to your point, ego get in the way and go, no, no, no, I'm going to figure out how to make this a good call. They're willing to make the necessary cut. There's another risk that this highlights, which I think also a lot of people don't pay enough attention to, which is this specificity risk.

51:29Paula Pant:the risk of two houses in the same community that there is a risk there now that volatility of being in one place can be a really good thing or a really bad thing in a weird weird weird coincidence paula yeah while we've been recording i checked my email i get these redfin notices because I'm looking at houses in the same area that Charlotte's talking about. And I received 10 minutes ago, a red fin notice about a house that just went on the market. That's$425 ,000. So it's, so it's pretty wild that, that this particular, this particular area of Lake Lure Chimney Rock is an area that I'm becoming very acquainted with and absolutely love, absolutely love.

52:25Paula Pant:And it was so sad to see the hurricane just take out Chimney Rock. This was the area that Paula, you saw on the news of houses just going down the hill, the entire house going down the hill during the aftermath of the hurricane. It was horrible, horrible devastation, but also just an unbelievably beautiful part of the country. But having two houses, well, first of all, having one house there, when you're dealing with a piece of real estate, that's a lot of money in one community. Having two houses, three houses, four houses in one community, you do begin to carry this risk of I'm invested in this specific geographic location.

53:12Paula Pant:And I think knowing that is an important part to winning at whatever investment you're in, knowing what your potential Achilles heel is. And if you think that your investment doesn't have an Achilles heel, you haven't looked hard enough. By the way, since we've been talking about rental properties and Airbnb and some of the mistakes that people make, we do have a free ebook. It's called Seven Expensive Rental Property Mistakes to Avoid. It's free. It's at affordanything.com slash mistakes. That's affordanything.com slash mistakes. And it's all the ways. Well, it's not all the ways. It's seven ways.

53:54But it's seven of the most common ways that people, especially in the beginning, can make mistakes when they're choosing a property, a rental property or an income producing property. Well, thank you for the update, Charlotte. Congratulations on everything that you did that brought you to where you are now. You fired and you're about to embark on an amazing adventure.

54:17Paula Pant:It sounds so fun. Please do call us back in a few years and give us an update as to that slow travel. And by the way, for anyone new to the community who's wondering what we mean when we talk about slow travel, it means, you know, when you've got two weeks of vacation or three weeks of vacation a year, you might have to rush your experience. experience the beauty of having time having the wealth of time is that you get to travel slowly and it creates a much deeper and richer experience and it's something that i hope that anyone listening to this who wants to be able to have that in your life it's something i i hope that you can create and that's what this show is for joe we did it yeah and what a wide range of discussions today.

55:06Paula Pant:I mean, the financial planning timeline system, which I love talking about, the emotions around our investments, which I think are really important for us to pay attention to. And also, we thought it was going to go this way. We did a lot of planning, but we had to change our plan and it still worked out. Right. We have some very resilient people in this community. Resilient, conscientious, driven. I'm inspired every day by the stories that you call in with. Speaking of you calling in with questions, affordanything.com slash voicemail is where you can call in if you have a question. That's affordanything.com slash voicemail.

55:49So again, I won't drive to too many things. I'll just say if you all want to download seven expensive mistakes that new rental property investors make, it's affordanything.com slash mistakes. And if you want to call in with a question, it's affordanything.com slash voicemail. Thank you so much for being part of this community. If you enjoyed today's episode, please share it with the people in your life, friends, family, neighbors, your Airbnb tenants, your TSP rep, the people who create the app that you're about to delete person at the fast food drive-thru any parent of twins.

56:21Paula Pant:They need this. Please share it with all of those people and more, because that is the single most important way that you spread the message of F-I-I-R-E. Thank you again for being part of this community. I'm Paula Pant. I'm Joe Salcihai. And we'll meet you in the next episode.

From the publisher

#722: Free lesson: affordanything.com/mistakes

Ask us a question: affordanything.com/voicemail 

What happens when your financial plan is technically working — but emotionally, it still doesn’t feel secure?

Caitlin and her husband have their core expenses covered, but her side hustle brings in an extra $600 a month. With young kids, daycare costs, and long-term retirement goals all competing for attention, she’s wondering where that extra money should go right now.

Anonymous is in a strong financial position for retirement, with a pension, solid investments, and high savings rates—but is still constantly checking accounts, rerunning projections, and struggling to feel at peace with money.

Charlotte is calling back several years after asking whether short-term rentals could fund her early retirement. After buying, renovating, and eventually selling two Airbnb properties—just before a devastating hurricane hit the area—she’s reflecting on what she learned about risk, hype, and investing with emotion.

Resources mentioned:

Charlotte's original call: affordanything.com/episode352

Paula interview on Emma Chamberlain's podcast: youtube.com/watch?v=VOP7S4w8s0I

Midterm Rentals with Jeff Hurst: affordanything.com/episode712

Interview with Brad Klontz, Ep127: affordanything.com/episode127

Interview with Brad Klontz and Adrian Brambila, Ep551: affordanything.com/episode551

Share this episode with a friend, colleagues, and your AirBNB tenants: https://affordanything.com/episode722
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