Spending money is an American pastime. With a national saving rate hovering around 5%, it's clear we collectively love to spend. And honestly, being able to enjoy our wealth is a beautiful thing. It’s something more personal finance enthusiasts like me—and readers of Financial Samurai—could probably do more of.
But like with most things, moderation is key. Overspending can trap us in the rat race forever. It can increase our anxiety about job security or unexpected health issues as we live paycheck to paycheck. And if you have kids, excessive spending might even put them at a long-term disadvantage, creating a cycle of financial stress.
In this post, I want to share a personal experience that helped me understand just how emotionally difficult it can be to stop spending, even when we know we should.
That Sinking Feeling of Being Judged
After dropping our kids off at parkour class, my wife and I took a stroll to Haight-Ashbury for some ice cream at Ben & Jerry’s. It's a nostalgic spot I first visited back circa 1993 on free cone day with a line several blocks long. Jerry Garcia from the Grateful Dead was still alive, and he was performing that day.
On our walk over, we passed funky odors and colorfully dressed folks who had just finished the Bay to Breakers race. When we finally reached the store, I asked the attendant if they had any unique flavors unavailable in grocery stores. She pointed to a sorbet, but we wanted ice cream.
Then came the sticker shock: $8.75 for one scoop, $13 for two. A waffle cone? Another $3.75. My frugal brain screamed, “This is insane! You can get a whole pint on sale for $5!” But I felt too embarrassed to back out in front of my wife. So I caved: one scoop in a waffle cone, $14 total.
We enjoyed it—triple caramel chunk—but I felt like a fool. On the walk home, I turned to my wife and said, “I’m never buying Ben & Jerry’s waffle cone ice cream again.”
The Shame of Not Spending
I didn’t stick to my frugal instincts because I didn’t want to look cheap. Even after years of being together, I still didn’t want to disappoint my wife.
This wasn’t just about ice cream. I had told her for several months that I was open to renting a house in Hawaii for our upcoming five week summer trip. When the stock market tanked in early April 2025, I figured, why not spend the money instead of losing it all in the stock market? At one point, we were down around $1 million, a gut-wrenching amount for dual unemployed parents. She agreed. YOLO and decumulate, right?
But the cheapest rental I found that we both liked was $24,000 a month after taxes, utilities, and fees. Yikes! That’s a lot when we could just stay at my parents’ house for free. Sure, it’s not ideal for privacy and puts a lot of pressure on my mother as a host, but it’s great for family bonding. And $24,000 invested in our kids’ custodial accounts today could more than double to $50,000 in 11 years at a 7% return. That could help pay for college or help them buy a home.
My wife was disappointed, and I don’t blame her. Living with in-laws isn’t easy. And she knows that hosting is especially hard on my mom, who needs her space—something that’s tough to maintain with six people under one roof, especially when two of them are particularly loud and rambunctious. My wife is also the planner for all of our travel logistics, so my indecision was starting to frustrate her.
But I just couldn’t get myself to pull the trigger, even if it is within my vacation spending guide. I felt bad for letting my wife down. If you're curious, below is the picture of the $24,000/month rental. Cute, right? But not for $24,000/month.
Tried to Spend Again After Several Big Wins
After about 35 days of painting, de-weeding, staging, and prepping our old house post-tenants, we finally sold it for a solid profit. Selling a home is often a stressful process, but we accepted a preemptive offer after a couple rounds of countering and ultimately hit my target price.
I used about 70% of the proceeds to buy the stock market dip over a 50-day stretch. First we were losing, which felt horrible given the home was such a stable investment. Eventually, the S&P 500 clawed back its full 20% loss, and I locked in gains on half our position. Our allocation for this important portfolio shifted from 100% stocks to a more balanced 60/40, as the S&P 500 returned to trading at 22X forward earnings—an expensive level in my book.
To top it all off, Millionaire Milestones made the USA TODAY bestseller list—a distinction earned by only ~0.04% of authors. I spent 2.5 months grinding away on marketing through guest posts on CNBC and MarketWatch, publishing related content on Financial Samurai, running consulting promotions, and giving interviews.
Surely, this triple win deserves a little celebration, right? I was exhausted after working so hard and taking so much risk. So I floated the idea of renting a house for a month again. YOLO, baby!
So Hard to Find Value When Booking a Vacation
My wife was cautiously optimistic. But as I searched more, I still couldn’t justify spending $24,000 for that house we looked at earlier because I really wanted a pool if we were going to shell out big bucks. Unfortunately, homes we considered with pools and views were going for $50,000 to $85,000 a month. A ridiculous sum of money. No thanks.
My wife could have cared less about a pool. She just wanted somewhere clean with two bathrooms, AC, a kitchen, and laundry that we could have to ourselves. Then we could have planned meals and family time with my parents at their convenience.
The thought of spending $24,000 on rent for just one month stung deeply, especially since I haven’t been a renter since 2002, when I was 25 years old. On top of that, it was emotionally draining to buy the dip and watch losses pile up for three to four weeks straight. Parting with that hard-earned cash felt too psychologically and financially painful.
I even asked my dad for advice since there are a lot of vacation rental scams out there too. During the stock market crash, he said, “Stay with us.” After the recovery, I showed him new options, and he still said, “Stay with us.” So I listened, as any good son would.
As a result, we will save $24,000 on rent and now have $800/day to spend on food, activities, and more. That feels amazing! All we can eat poké here we come! But I could tell my wife wasn’t as thrilled. Ah, the feeling of disappointing her again despite the wins we had.
Ice Cream as Emotional Compensation
So when the Ben & Jerry’s attendant asked, “How many scoops?” I flashed back to all of this. I felt ashamed that I couldn’t follow through on the vacation rental. I'm the provider, gosh darn it. I didn’t want to let my wife down again. So I said yes to the overpriced cone at least.
But afterward, I still felt stupid. I knew I could get a more delicious matcha soft ice cream in a waffle cone at the mall for $6.90, or half the price.
Spending $14 on ice cream was my emotional Band-Aid for not spending $24,000 on the vacation rental. But it didn’t fully patch the wound. I still feel like I need to do more.
As someone who grew up middle class with frugal parents, there's simply no way I can justify spending that much on a temporary living arrangement with no equity. I've spent too much of my life focused on building wealth, not spending it.
Besides, at least 70% of the joy of being in Hawaii comes from just being there, enjoying the weather and outdoors. I don't plan on staying inside for most of the day.
Fear Of Being Judged Is Why We Overspend
This experience helped me realize something important: We often spend money not because we want or need to—but because we don’t want to be judged, especially by loved ones. Even after 26 years together, I still didn’t want to disappoint my wife.
Unlike some personal finance or FIRE enthusiasts, I don't take being called or viewed as cheap as a badge of honor. Instead, I take offense to it because I'm fully spending my money according to my values. And we don't all value the same things, so who is anybody to judge?
This need to appear generous, carefree, or successful may push us to spend more than we should. Our insecurities lead us to waste money on things we don't value. We’re not always spending for joy, we’re spending to protect our image.
I don’t care what others think, only what my wife and children think. As men, we often work tirelessly to provide for our families, yet there are still moments when we feel like it’s not enough.
Related: Feeling Like A Burden Is A Terrible, Terrible Thing
The Solution to Overspending
The next time you feel pressure to spend, pause and revisit your core values and financial goals. If you don’t know what they are, figure them out—fast. Ask yourself: Does this expense align with who I am and what I want for my future? If the answer is no, then don't spend. Love yourself enough to follow your values.
And if you’re in a relationship, talk it through. Being on the same page financially is important for a successful, long-term partnership. The last thing your partner wants is for you to be grouchy or regretful after spending. At the same time, you don't want to let your partner down and feel constrained, especially if you have the funds. Resentment will only build.
In our case, the compromise I came up with is to spend weekends at my aunt’s beach house on the other side of the island to give everyone some breathing room, assuming she's okay with that. The only problem is my aunt hasn’t said yes, yet! She's traveling.
Another solution is to spend one or two nights at a beachfront resort in Waikiki or Kahala. I’m open to booking a Saturday night so we can make the most of the facilities on both Saturday and Sunday. Maybe we should do Friday night as well, but the kids get out from summer school at 3:30 pm on Friday, so is it really worth it? Perhaps I’m being too frugal again, but at least I’m offering up solutions. That’s progress!
Readers, do you think we mainly overspend because we are not secure with ourselves? Why do you think it's so hard to stop spending despite knowing we should be saving and investing more? Is it silly to let other people judge us for how we spend our own money?
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To put the shoe on the other foot, would your wife spend $24,000 of her own money on a month rental? Money feels different when it is your money.
Money does feel different when it’s coming from your own pocket versus the shared pot. That’s where things get interesting in relationships. If my wife personally earned and managed her own $24,000, I’d be curious to see if she’d drop it on a month-long rental too. But when it’s shared money, those lines blur and the justification changes.
It’s a good reminder that even in a partnership, maintaining a sense of financial autonomy can help keep spending decisions more grounded. When both people have skin in the game, the calculus shifts.
The $24,000 after tax would take up a majority of the money she earned from editing Millionaire Milestones. Probably spent a year doing all the edits and back and forth.
But the reality is, all the money is shared. We just have to make joint decisions.
What would you do?
Related: Financial Dependence Is The Worst: Why It’s Good To Have Separate And Joint Accounts
Spending is a skill just like saving
You may just need to practice more I like the idea of the weekends at the hotel.
Our net worth is 3mil and we just bought flights to Japan from east cost for 8k I have not problem spending on vacations keep practicing
If you don’t spend it your kids will so why not spend it together making memories
True. I’m not very skillful at spending. But I do try either my houses, automobiles, and children’s education.
$8,000 ain’t too bad depending on how many people and which class. I thought first class round trip to Japan is closer to $10,000 -$13,500 per person? If so, you got yourself a steal! Or, it may time to spend up.
I can’t seem to find value when I look at travel. It’s hard to get excited about leaving our nice home and cars to stay in a hotel room with 3 kids. Bigger accommodations are costly, and often nothing special. Maybe I’m getting paranoid, but safety and healthcare are also big considerations.
My husband flew this week for business and came home saying he doesn’t miss it at all. The cake topper was a bag inspection notice in his checked suitcase.
Isn’t there a proper economic term for too much and nothing to buy? Haha
Hear you on the ice cream cone till surprise. $14 is too damn much!
I can’t see it either! And that’s one of the problems of buying a nicer house. To have something comparable on vacation will cost a fortune. At the same time, you don’t want to pay a smaller fortune for an inferior property.
Time for your husband to take it easier!
Gah I understand the complexity of feelings both you and your wife have been going through. Hawaii? Beautiful place (that gets away with charging out the wazoo). Still worth going and spending some dough? Absolutely. But as for how much and on what is going to be different for you than for me and anyone else reading this post. Going as a vacation vs going to spend time seeing parents is also very much not the same thing.
I love my parents, but I don’t really enjoy spending time with them beyond a few days. They’re not going to read this, so I can speak my truth. Sleeping on an air mattress sucks after the first night. Would I like to spend more time with them? Yes, sure, but for me I need it in small doses or it makes me crazy and them too because they start incessantly nagging about the dumbest stuff.
Does that make me sound like a bad person? Maybe. But frankly familial relationships are incredibly complicated. And anyone who doesn’t agree either has the rarity of angel parents, is in denial, or is too embarrassed to fess up about their family’s issues. My biology strongly pushed me out of my parents’ house as quickly as I could once I hit 18. I fled with glee. It’s like we have opposing magnetic forces – it’s really hard for me to go back because I feel pushed away.
Anyway, before I ramble any more, I wish you the best on your trip and hope you can find a good balance for everyone. I sure as heck couldn’t live with my parents or my inlaws for more than five days so I can’t believe you’re going for five weeks! Wow. If things don’t work how you hoped, try your best to figure out some things to pivot. Maybe eat separately or send your parents out by themselves in an Uber to the movies or something.
Thanks for sharing your thoughts, Casey! I just got an email from your mom asking me to delete your comment and call her ASAP! Just kidding :P
The secret to coexisting peacefully with parents and in-laws? A mega-mansion with separate wings for each family! Too bad my parents and grandparents didn’t scoop up an acre in Waikiki back in the 1920s–1970s when it was affordable.
Yes, five weeks is a long time. But after missing out on precious moments during the 2020–2021 pandemic, I just want to be with my parents. I still regret not buying that property I’d been eyeing for years at the end of 2019—it would’ve been perfect. But with our daughter arriving, I chose stability.
I often ask myself: Will I regret spending five weeks with my parents once they’re gone? Never. It’s the small, everyday interactions—saying “What’s up, Dad?” or “How’s it going, Mom?”—that matter most. Just a few minutes here and there are priceless. And then we can retreat to our rooms or go outside.
If we make it through five weeks living together under one roof, that’ll be a cool milestone in itself.
And one day, when I’m a grandparent, I hope my kids will come visit me. I’ll welcome them with open arms and make them feel as loved and appreciated as possible.
Sam, I love you/your writing, but I disagree. :) You should have shelled out the $24k and enjoyed it. What’s the point of having money if you don’t spend it? I just do not think you would be overspending. Same thing with the ice cream. If you were going to buy the $14 ice cream every day — that would not be right. But you can (and should) afford it once in a while. If you were to spend $200k on a rental — that would not be right. But $24k — this is OK for 1 month only. I just don’t think this qualifies as overspending, unlike $14 ice cream _every day_ or $200k vacation rental.
Thanks for sharing your thoughts Yury! I hear you, and you make a great point — money is meant to be enjoyed, not just saved and invested forever. The challenge for me is psychological: I’ve been wired for so long to seek value and avoid lifestyle creep that spending $24K in one go—even just once—triggers that internal tug-of-war.
You’re right, it’s not the same as blowing $14 on ice cream every day or renting a place for $200K. But after grinding so hard to buy the dip and feeling the sting of short-term losses, the cash just felt extra hard-earned, you know?
I felt stupid paying 414 for an ice cream AND ingesting more calories than I needed. I’m working on the mankini beach body, not the other way around!
I’ve only ever been to Hawaii for vacation, ie not working and not to visit relatives, so I didn’t need much space at the time and was able to bask in the sun and utilize all the amenities at my hotel. Speaking of which, hotel prices are very expensive there during peak season because they know they have plenty of demand willing to pay for it. It is what it is during high season. I try to travel off peak when I can but that doesn’t often work anymore with my schedule. Whatever you end up doing, I hope you have a good time all around. It’s a beautiful place.
I agree that 70 to 80% of the joy of being in Hawaii is just being there. Doesn’t matter how nice of a place you stay at is because you want to be outside at the beach or hiking or play golf or horseback riding. I don’t want a nice place keeping me inside. I’d rather have a mediocre place, forcing me to go outside!