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

Summary

Afford Anything Podcast | Make Smart Money Choices
Episode: "Q&A: Why Do I Still Feel Anxious When I’m Clearly Doing Well?"
Date: June 9, 2026
Host: Paula Pant | Guest: Joe Salciccia (former financial planner)

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Episode Overview

This episode explores the complexities of financial decision-making and the emotional landscape that often underpins our money choices. Paula Pant and co-host Joe Salciccia answer listener questions about what to do with unexpected extra income, why financial anxiety persists even when you’re “doing well,” and share a follow-up story about real-life lessons from short-term rental investing. The hosts dig into behavioral finance, real-life goal setting, and emotional resilience, providing actionable advice that goes beyond the numbers.

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Key Discussion Points & Insights

1. What to Do With Extra Side Hustle Income (Q1: Caitlin from Portland, OR)

[01:21-12:41]

Background:

• Caitlin has a stable household income, contributing $600/month extra from a side hustle.
• No debt except a low-rate mortgage, solid emergency fund, considerable retirement savings, and two young children in daycare. Wants to allocate extra money wisely with both short- and long-term goals.

Discussion Highlights:

• Joe’s model: Three potential approaches:
  1. “Fill in potholes”: Identify and shore up underfunded goals or gaps (e.g., beef up savings, kids’ funds) ([04:42]).
  2. Timeline focus (Near term): Think about large upcoming expenses in the next 5 years (cars, vacations, home repairs, etc.) ([05:13]-[06:22]).
  3. Timeline focus (Long term): Prioritize long-term security by stacking up retirement savings—accelerating timeline to “freedom from worry” ([06:46]).
• Paula’s perspective: Echoes the need to anticipate big five-year expenses, but leans toward supercharging retirement for its psychological benefits—reaching “Coast FI” earlier means more freedom and future flexibility ([07:57]-[09:41]).

Notable Quotes:

• “Timeline it all. Take a look at how the goals fight against each other.” – Joe ([04:41])
• “Every day you wait is a mistake.” – Joe ([12:26])
• “You will never be younger than you are today.” – Paula ([11:58])

Key Insight:

Use your extra income to either strengthen weak spots in your goals or to push aggressively toward long-term independence. Modeling out the impact is key, and accelerating retirement savings can buy priceless peace of mind.

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2. Why Do I Still Feel Anxious When I’m Doing Well? (Q2: “Jane,” formerly Anonymous)

[17:07-35:56]

Background:

• “Jane”: Federal employee, age 37, solid six-figure income, mandatory retirement at 57, significant investments (TSP, Roth, brokerage), enjoys life but wrestles with constant account-checking and financial anxiety.

Discussion Highlights:

• Paula identifies core issue: There’s a disconnect between Jane’s objective financial health and her persistent anxiety. The looming mandatory retirement may trigger a sense of powerlessness and scarcity ([21:14]).
• Joe on Behavioral Patterns: Suggests financial therapy as an emerging, valuable resource—relates his own journey of connecting subconscious emotional triggers with money behaviors ([23:22]-[25:28]).
• Constructive Reframing: Paula and Joe debate best tactics:
  • Joe: Assign worries constructive tasks—create an “investment policy statement” and schedule check-ins to channel the need for control productively ([26:20]-[28:00]).
  • Paula: Behavioral change (e.g., deleting investing apps) helps alter thoughts/feelings via changed habit loops. Suggests behavior, thought, and feeling as a triangle—each influences the others ([29:43]-[33:30]).
• On Deep Roots: True peace requires uncovering past experiences that drive money anxiety. Financial therapy (not just any therapy) should be considered for specialized help ([30:14]-[31:58]).
• Bravery in Vulnerability: Both hosts commend Jane for articulating the universal emotional challenge of money management.

Notable Quotes:

• “I can hear the struggle in your voice… How much suffering… It’s heartbreaking because you are doing so well.” – Paula ([19:29])
• “Fast food does not equal love… That Big Mac is not going to love me back.” – Joe ([25:10])
• “If you think your investment doesn’t have an Achilles’ heel, you haven’t looked hard enough.” – Joe ([52:41])
• “Money can be a very emotional topic. Driven much more by fear and joy than by objectivity.” – Paula ([35:03])

Memorable Moments:

• The “triangle” (thought, feeling, action) model for behavior change ([29:43])
• Joe’s personal parallel: emotional eating ↔ anxious money checking ([23:22])
• Highlighting the unique value of financial therapy versus traditional therapy ([31:07])

Key Insight:

Even the “well-off” struggle emotionally with money. True peace may require both engineered habit changes and, crucially, unpacking personal money scripts with a trained therapist.

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3. Real Estate Lessons & Resilience (Q3: Charlotte’s Short-Term Rental Update)

[41:55-54:15]

Background:

• Charlotte followed up on her 2022 question about using short-term rentals (STRs) for early retirement. Post-pandemic, she scaled to a second STR, only to face underperformance, management burnout, a forced sale with a loss ($80k), and then, mere months later, a devastating hurricane in that very area (properties survived but would’ve been unrentable for a year).

Story Highlights:

• “I was totally caught up in the Airbnb post-COVID craze… our first property had really been a unicorn.” – Charlotte ([42:11])
• Market “lessons learned”:
  • Don’t let ego, sunk cost fallacy, or influencer hype drive decisions.
  • STRs are hospitality businesses—with unique risks and workload.
  • Diversification matters: both properties were exposed to the same local disaster risk.
  • Positive: She and her partner adapted, sold, took the loss, and are retiring anyway in June 2026—ready to “slow travel” with flexibility and a backup plan.

Notable Quotes:

• “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.” – Charlotte ([44:27])
• “Your competition is Hilton, Marriott, Sheraton, Hampton Inn. Right. Your competition are hotels. That’s very different.” – Paula ([47:36])
• “Not letting sunk cost, not letting ego, not even letting loss aversion drive your decision-making… That is a hallmark of good investing.” – Paula ([49:25])
• “If you think your investment doesn’t have an Achilles’ heel, you haven’t looked hard enough.” – Joe ([52:41])

Key Insight:

Short-term rental investing is a business, not a passive asset class. Emotional detachment, situational flexibility, and risk awareness are vital; success sometimes means cutting losses and pivoting with grace.

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Timestamps for Key Segments

• [01:21] – Caitlin’s Question: Side Income Allocation
• [04:41] – Goal “Timelining” and Modeling Approaches
• [07:57] – Coast FI/Long-Term Mindset
• [09:41] – Retirement Bills and Psychological Freedom
• [11:58] – “You’ll never be younger than you are today”
• [17:07] – Jane’s Question: Persistent Financial Anxiety
• [19:29] – Emotional Suffering Despite Doing Well
• [23:22] – Financial Therapy and Emotion Roots
• [26:20] – Assigning Worry Constructively (Policy Statements)
• [29:43] – The Thought-Feeling-Action Triangle
• [31:07] – Distinct Need for Financial Therapy
• [35:03] – Behavioral Finance and Emotional Money Relationships
• [41:55] – Charlotte’s Update: STR Investing Lessons
• [44:27] – “Don’t buy with emotion…”
• [47:36] – STRs vs. Hotels
• [49:25] – Recognizing/Overcoming Cognitive Biases
• [52:41] – Risk Awareness (“Achilles’ heel”)

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Memorable Quotes & Speaker Attribution

• Joe: “Timeline it all. Take a look at how the goals fight against each other.” [04:41]
• Paula: “You will never be younger than you are today.” [11:58]
• Paula: “I can hear how much suffering… It’s heartbreaking because you are doing so well.” [19:29]
• Joe: “Fast food does not equal love… That Big Mac is not going to love me back.” [25:10]
• Paula: “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.” [35:03]
• Charlotte: “Not with emotion and not because some influencer on YouTube told you it was a sure thing.” [44:27]
• Joe: "If you think your investment doesn’t have an Achilles’ heel, you haven’t looked hard enough." [52:41]

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Thematic Summary

• Behavioral Roots Matter: Smart money moves aren’t just about finding “the right answer”—they’re about knowing yourself and your tolerances, plus emotional triggers.
• Financial Therapy & Self-Knowledge: Being “fine on paper” is sometimes not enough. Lasting change—and relief from anxiety—often means digging much deeper and possibly getting help.
• Real Estate Cautionary Tales: Emotional investing amplifies risk and can cloud judgment; flexibility, humility, and strategy beat hype every time.
• Community and Resilience: The Afford Anything audience consistently demonstrates adaptability, resilience, and the willingness to learn from setbacks.

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Further Resources Mentioned

• Episodes with Dr. Brad Klontz on money anxiety and financial therapy
• Paula’s free ebook: “7 Expensive Rental Property Mistakes to Avoid”
• Afford Anything Voicemail for future questions: affordanything.com/voicemail

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Final Thought (Paula):
“I’m inspired every day by the stories you call in with… If you want slow travel, if you want a different relationship with money, that’s what this show is for.”

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Summary prepared to capture the nuance, practical advice, and humanity at the heart of this episode, complete with actionable insights and emotional resonance.

Transcript

[A]

Joe, 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 all the time? How did you address that?

[B]

We. Well, why don't we get into that later?

[A]

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.

[B]

Sounds like an adventure.

[C]

It is.

[A]

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 acronym 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 Salsihai. What's up, Joe?

[B]

You know, I was out buying groceries this morning and I realized that my wallet is just like an onion, Paula.

[A]

It has many layers.

[B]

Every time I open it, it makes me cry.

[C]

Oh,

[A]

well, with that, we're going to go to our first question, which comes from Caitlyn.

[D]

Hi Paula and Jo. This is Kaitlyn calling from Portland, Oregon. My question in a nutshell is what to do with how to think about the extra income I bring in through my side hustle. My husband and I Both have stable W2 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? 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. 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 to nine. 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.

[B]

Caitlin. Twins.

[A]

Twins.

[B]

I have twins. I'll foreshadow the future. Caitlin, 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.

[A]

No more childcare.

[B]

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?

[A]

Like a. I don't know, laughing gas.

[B]

A cantaloupe, A honey crisp apple. I like those a lot.

[A]

Okay, so like a piece of fruit that sparks joy.

[B]

Yes.

[A]

As opposed to a vegetable that makes you cry.

[B]

Yes, exactly. This is an interesting problem, Paula, because really, you know, the way I see it, there's three ways she can handle this.

[A]

Interesting. Okay, I. Actually, Nicho, 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.

[B]

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.

[A]

Timelining, model it all up.

[B]

Yep. Timeline it all. 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. 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? Because the first way you can do things is just like filling in potholes. You know, take the pothole fill, find out where the potholes are, fill those in. That's option number one.

[A]

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? For example, maybe you might be buying, 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.

[B]

And that for me was option number two. Which is, 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,

[A]

Is it the other end of the line?

[B]

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. 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 a gamification and also the $500 a month.

[A]

600amonth.

[B]

The 600amonth. I almost shortchanged her. The 600amonth goes further because the return on that money, if we put it toward long term goals, means it's, it's easier to backfill that. Of the three things, I would model it out no matter what and see where she's at with each stage of the timeline. Is she ahead or is she behind on all those goals? Just use a calculator, work with an hourly financial planner, do it, or whatever she's going to do. Figure out where she's at with those. But my bias is secure.

[A]

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. You know, we, we talk on this podcast about the concept of coastfi, which I guess everybody has their own semantic difference in what that means. But I define coastfi as the point at which your retirement accounts are well funded enough that you don't have to save for retirement anymore. So 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. That is what coastfi 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.

[B]

Yeah. 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, 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, 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, like, it's going to get really rosy very quickly.

[A]

Right? Joe, your twins are 31 now.

[B]

30.

[A]

30.

[B]

Almost 31. Oh my goodness. They'll be 31 in the next couple of weeks.

[A]

Ah, congratulations.

[B]

How can they be 31 when I'm only 35? 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.

[A]

Oh, beautiful.

[B]

I can never say the name of it. And everybody in the Portland area will be screaming at their device. Multnomah Falls, I think Multnomah, maybe. Whatever I say it, my friends from Portland always correct me. So it's a beautiful waterfall. Have you been here before, Paula?

[A]

No, I've been to the Portland area, but I've never been to that particular waterfall.

[B]

Beautiful. All the waterfalls along the Columbia river gorge are just gorgeous. Great place to spend a lot of time.

[A]

The gorgeous, gorgeous, gorgeous, gorgeous.

[B]

As is wine country. Let's just go to Portland. Forget it, Caitlin. We're coming to visit.

[A]

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. And 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.

[B]

You heard it here first. Everyone but you will never be younger than you are today.

[A]

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.

[B]

Oh, yeah, right. Exact. Exactly.

[A]

And so I want to make the point that, yes, you still are. Young is a relative term.

[B]

Yes.

[A]

And so an older version of you is going to look back on the U of 2026 and think, wow, I was so young back then.

[B]

Every day you wait is a mistake.

[A]

Right, Exactly. See, there's a method.

[B]

It was better than the first blush. I was like, wow, that should go on a book cover. That's deep.

[A]

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. There's always something you want to get better at. For me, it's writing. It's a lifelong quest to become a better writer. So I went to masterclass and I found a class taught by R.L. stein. Do you remember him? He wrote the Goosebumps series. And even though that's totally different than the type of writing that I do, there are lessons that carry over. In fact, I think having taken his class, my writing is now richer, more vivid, more engaging. He talks about using cliffhangers, using simple sentences. These are takeaways that I use when I'm. I'm writing about economics, I'm writing about managing money. But I'm doing so with the benefit of having learned from great writers like him. Masterclass puts you in the room with the people who defined their fields. Not just experts, but the best in the world. They've got more than 200 classes across 13 categories. Business, writing, cooking, creativity, wellness and more. Plans start at just $10 a month billed annually, and every new membership comes with a 30 day money back guarantee. And I like putting on Masterclass in the background while I'm unloading the dishwasher, while I'm folding laundry. So it's something that you can incorporate into your life. You don't have to schedule time for it. It fits into real life with short lessons on your phone or on your tv. Masterclass keeps adding new classes, so there's never been a better time to get in. Right now, as a listener of this show, you get at least 15% off any annual [e-mail] afford. That's 15% [e-mail] afford. Head to masterclass.com afford to see the latest offer. You may have some amazing plans for the summer. Maybe you're going to the beach, you're going to the mountains. Maybe you're visiting family or taking a long road trip. Maybe while you enjoy your summer days, policygenius does the hard work of searching for the insurance that will protect your family in the event that the worst were to happen. So the thing about life insurance is that it's not something you buy for yourself, it's something that you buy for the people who rely on you in the event of the worst case scenario. And policygenius makes finding that a lot more straightforward. So they're an online insurance marketplace that helps you compare quotes from some of America's top insurers to side by side for free. Their licensed team helps you get what you need fast, so they'll walk you through coverage, amounts, prices, terms. They have thousands of five star reviews on Google and Trustpilot. With Policygenius, you can see if you can find 20 year life insurance policies starting at just $276 a year for $1 million in coverage. Head to policygenius.com to compare life insurance quotes from top companies and see how much you could save. The that's policygenius.com 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. That's why reliability is at the core of USPS Ground Advantage. From the moment your package is first scanned in, it moves through a secure nationwide network, aiding in a timely and accurate delivery. You get near real time tracking so you can keep up with your shipments and with affordable upfront pricing. There are no hidden fees or surprise surcharges to throw off your cost sheets. It all adds up to predictable deliveries you can depend on, because knowing your logistics are handled lets you focus on everything else your customers, your team, and the future you're building. Visit USPS.com ground advantage to start shipping with confidence. USPS ground advantage we Mean business. Welcome back. Our next question comes from Anonymous.

[E]

Hi Paula and Joe, 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. 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. You know, I 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. And I have recently deleted my apps temporarily, so I'm not checking them constantly, 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.

[A]

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. 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 and then let's talk through a few tactics that might help address it.

[B]

Oh, we've got more important things to do than that.

[A]

Are we going to give her a name?

[B]

We need to. She wants 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, like, 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 haven't read it, but it's well worth reading.

[A]

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

[B]

Well, if you haven't read King lear,

[A]

you've had 400 years.

[B]

It's on you. I should probably say that about Jane Eyre as well. You know, we probably had enough time. But anyway, I thought we could call her Jane.

[A]

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. But there is a world of difference between a voluntary and a mandatory one. To 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 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. You 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.

[B]

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.

[A]

Sorry I stole your punchline, but it is, Paula.

[B]

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. I did this a long time ago with a therapist. It was. 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, but 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. 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. Like 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 through because of this childhood memory.

[A]

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.

[B]

Exactly. Fast food does not equal love.

[A]

Right. That.

[B]

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.

[A]

Oh, wait, is that the place that we, you and I went?

[B]

That's the iconic place that you and I went.

[A]

Oh, that place is great.

[B]

Yeah, yeah. You know those travel guys. Jason.

[A]

Yeah, yeah, yeah.

[B]

Yes, yes. He came to Texarkana and went to tlc and it was incredible. But anyway, that's. Anyway, that's neither here nor there.

[A]

I still looking for a fast food recommendation in Texarkana, Texas. Yes, you just got one.

[B]

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.

[A]

Oh, so I disagree with you here, Joe, but please go on.

[B]

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. There were a couple 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. 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 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.

[A]

I like where you're going with that. Although we also don't want Jane to get into a habit of constantly tweaking and updating the policy statement.

[B]

But I don't think you do. I don't think that's the outcome. I've never had that be the outcome.

[A]

Okay, but to your earlier point, Joe, about how you think that, where I disagree with you is, 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. All three of these influence one another. So you imagine a triangle, and the triangle is thought, feeling, and action. And these three things as the three points of a triangle, these all influence one another. Your 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, and instead of when she needs to make new contributions, do it on a. 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. That's what apps do. So use behavioral modification. 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.

[B]

Maybe. I feel like that's still a leaf versus the root of the tree.

[A]

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.

[B]

Yeah.

[A]

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. 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 hang ups 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. You 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 how the reason why the nascent field of financial therapy, specifically financial therapy, people who are trained in that. 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 compliment.

[B]

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. 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.

[A]

And 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 over checking 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. And so those cover the three points of the triangle.

[B]

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.

[A]

Yeah. Yeah. Thank you for asking.

[B]

Yeah. The fact that you did was pretty kickass.

[A]

Yeah. Because so much of our relationship with money, it is a deeply emotional relationship.

[B]

I went from being an okay financial planner to, I think a really good financial planner. Sounds like I'm talking. I'm patting 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. We started focusing on time, lining 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. You know, the value that we place are. 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, 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.

[A]

Yeah. 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.

[B]

Oh, I see what you did there.

[A]

Yeah, 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, 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. So 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. That means you've probably got all kinds of plans for the warm weather. Maybe you want to go on vac, go to the pool, go to the beach. And you want to make sure that you aren't worried about money when you do this. You know you've planned ahead. You know that you can pay for whatever summer fun you want to have. You can do that with Monarch. Monarch is the personal finance app that tracks everything accounts, investments, savings goals and spending. Get your first year of Monarch Core for half off just $50 with promo code Afford Monarch is basically like having a financial advisor in your pocket. It gives you clarity on things like your savings rate, cash flow, visualizations that show you where your income goes. It helps you figure out whether or not you're hitting specific savings goals or if you're on track to hit a net worth milestone. The thing is, most apps only tell you what you've already spent. Most apps are backward looking. Monarch helps set goals and map out big purchases. It's forwards looking. You can ask Monarch's AI assistant anything about your finances and get a heads up on what's happening with your money with the AI. Weekly recap use code affordonarch.com to get your first year of Monarch Core half off at just $50. That's 50% off your first year at monarch.com with code afford a F F O R D 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. I don't have outdoor space. I live in a Manhattan apartment. I have indoor space and my space has a bunch of pieces from Wayfair so I have a daybed. It's super functional because it doubles as a guest bed and a bookshelf and then there are drawers underneath so it's great for storage in a small apartment. I've got a bunch of shelves from them. Personally, as an apartment dweller I would recommend anyone who's looking for space saving and highly efficient options. There's a ton of selection at Wayfair. I would recommend recommend that you check them out. If you haven't tried Wayfair yet. The main thing that I hope you understand is how much selection they have. Anything you're looking for outdoor seating, grills, major appliances, patio lighting, rugs, decor, Big things, small things, any style, any budget. With over 20 million five star reviews, you can hear from real customers before you buy and you can shop with Wayfair Verified. It's a shortcut to the good stuff. So their team of product specialists vets everything by hand using a 10 point inspection. So they test things like quality of materials, functionality, features. The major thing I cannot emphasize enough is how big of a selection they have. Whatever you're looking for, any style, any budget, they've got it. Patio season is here and these deals won't last. Head to Wayfair.com right now to get your outdoor space ready for way less. That's W a Y F A I R.com Wayfair Every style, every Home Hiring isn't just about finding someone willing to take the job. I need the right person with the right background who can move our business forward. If I wanted candidates who match what I'm looking for, I'd trust Indeed Sponsored Jobs. In fact, I did. I used Indeed Sponsored Jobs to make two hires. One was for an executive assistant and the other was for a customer support important operations assistant. For both positions we had the job posting up for less than 48 hours and within that time we got so many applications we got what we needed. So if you're hiring Indeed is all you need. Give your job the best chance to be seen with Indeed Sponsored Jobs. Sponsored Jobs boosts your post for quality candidates and that makes a big difference. Sponsor Jobs posted on indeed are 90% more likely to report a higher than non sponsored jobs at more than 1.6 million million companies sponsor their jobs with Indeed. So our two hires have both been working for us for several months now. They're great, wonderful part of the team and we found them through Indeed Sponsored Jobs. Spend more time interviewing candidates who check all your boxes. Less stress, less time, more results. Now with Indeed Sponsored Jobs and listeners of this show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com Paula just go to Indeed.com Paula right now and support our show by saying you heard about Indeed on this podcast. Indeed.com Paula Terms and conditions apply. Hiring do it the Right Way with Indeed. Welcome back. Our final question today comes from Charlotte.

[C]

Hi Paula and Jo. 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 we're looking to grow our portfolio to three or four. We ended up purchasing STR2 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 reevaluated. 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 eight 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 and we ended up losing about $80,000. 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. 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.

[A]

Amazing. Congratulations. I love this.

[C]

Wow.

[A]

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.

[B]

You know what that means. They need to come to Texarkana they have to.

[A]

Yeah, that's right. There's. What is it called? Tlc. That fast food place in Texarkana. Yeah.

[B]

Yes. I'm always up for a hamburger. 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, you know, 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? Like, of 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 gonna 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.

[A]

So, yeah, flipping is a full time job for sure.

[B]

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.

[A]

Charlotte, 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 a, 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. As 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 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.

[B]

I get people first get into short term rentals. You, 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, it 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. And when you get the bad reviews, that's a death knell to your short term rental.

[A]

Well, and now there are also major companies that are in the short term rental business and they have economies of scale.

[B]

At scale.

[A]

Yeah, exactly. So it's nothing like what it was, medium term rentals. That's a. I won't go down that rabbit hole right now. But that is, 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. You 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. That 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.

[B]

I know that you and 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 trait 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, the risk of two houses in the same community, that there is a risk. They're not 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?

[A]

Yeah.

[B]

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. Oh, and I received 10 minutes ago, Redfin 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. 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, 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. 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.

[A]

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 7 expensive rental property Mistakes to Avoid. It's free. It'[e-mail] mistakes. That's affordanything.com mistakes. And it's all the ways. Well, it's not all the ways. It's seven ways, but 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.

[B]

It sounds so fun.

[A]

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. The beauty of having time, having the wealth of time, is that you get to travel slowly and it creates 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 the show is for. Joe, we did it.

[B]

Yeah. And what a wide range of discussions today. 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?

[A]

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 voicemail is where you can call in if you have a question. That's affordanything.com voicemail. So again, I won't drive to too many things. I'll just say if you all want to download 7 expensive mistakes that new rental property investors make, it's affordanything.com mistakes and if you want to call in with a question, it's affordanything.com 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

[B]

at the fast food drive thru, any

[A]

parent of twins, 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 fi r e thank you again for being part of this community. I'm Paula Pant.

[B]

I'm Joe Salcey.

[A]

And we'll meet you in the next episode.