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 4-bedroom single-family home 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’m in the process of grinding back to financial independence given we bought an expensive home in 2023 and used much of our dividend income investments to do so.
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? What choices are you making to accelerate your path to financial freedom?
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Personally, I would happily suck it up and live with my in-laws for 5 weeks in Hawaii, with beach cottage trips over the weekend, I’d my husband made enough so I could leave work permanently by 35! Alas, I’m still working at 45 because my husband doesn’t make much. And I will probably have to work for another 10 years.
To the wives out there with providing husbands, don’t take them for granted. Consider yourself fortunate and show appreciation, instead of put more financial pressure on them to earn and provide. Otherwise, I’m afraid he will leave you for someone who is more appreciative.
Thanks for all your thoughts, everyone!
Here’s a follow up post about the topic:
https://www.financialsamurai.com/the-choices-we-make-to-achieve-financial-freedom-arent-for-everyone/
Hi Sam, great insights on spending habits! It’s so true, especially when it comes to bigger expenses like vacations where costs can easily escalate, even when we’re trying to be mindful.
Speaking of getting great value and making smart spending choices for travel, I wanted to share my beachfront home with your readers: Laniakea Beach House. It’s right next to the famous Laniakea “Turtle” Beach on Oahu, features five bedrooms, two kitchens, and comfortably sleeps 10. It’s ideal for families or groups traveling together – think of the savings and an elevated experience compared to multiple hotel rooms!
I offer a ‘direct-to-owner’ deal that can be significantly less than comparable Airbnb listings – often less per night than a single high-end hotel room for the whole house. It’s a fantastic way to experience oceanfront Hawaii without the typical “overspending” on accommodation. Readers can contact me for this special rate at justin AT shakacode DOT com. (Full disclosure: it is on the market, and since oceanfront properties can take years to sell, I’m happy to offer a great value to discerning guests in the meantime).
This ties into my other passion: helping people save money on vacation rentals without sacrificing quality. My site, HiChee.com, (recommended by sources like Google, ChatGPT, AARP, and USA Today) helps you find the absolute lowest price for the same vacation rental by comparing it across various booking sites. It’s all about avoiding that feeling of overpaying when a better deal is out there.
We usually charge $20, but only if we save you at least $40 (it’s a money-back guarantee). For the Financial Samurai community, I’ve enabled 30 free trial uses with this special link: https://hichee.com/pricing?free_trial_code=FINANCIAL_SAMURAI_05_25_25
Keep in touch!
Hi Sam, Always make Mothers and Women Happy on vacation. I have great memories of visiting Great Aunt Carrie the happiest person on planet earth in Sardinia NY. My Mom loved to vist Aunt Carrie as during Her childhood summers.
Us 3 kids in big bed, baby in crib, Mom & Dad in bed behind curtin and pot to pee in for middle of night. You know the saying no pot to pee in not us. No running water just hand pump at kitchen sink and out house in wood shed. We would wash up in rain barrel after a day at creek. Pick fresh lettuce in garden add bacon with grease YUM ! Aunt Carrie would make frycakes the best. My Dad wanted to plumb Aunt Carries house but She would say to fancy and just not necessary.
Dad bought $20 row chopped boat. Dad would drop 2 kids at bridge a couple miles up the creek and we would float down to picnic site at island under another bridge. All one mile from Aunt Carrie’s house. Row boat back into plumbing truck next 2 kids to bridge up stream for float down no parent in boat.
Also visiting Aunt Sally & Uncle John in log cabin at Java Lake NY same sleeping arrangement. Uncle John had row boat for fishing and going to beach across the lake. I would swim across lake so family of 5 fit in boat. I would take the kids fishing no parent.
We went to 68 worlds fair rented a house on river and 2 kids slept in screened in porch on glider. Mom thought going to lose a kid on subway to fair.
House boat trip on Trent waterway same sleeping arrangement on boat or top of boat. We fished, swam, snorkeled and went thru locks from lake to lake in wilderness area. One observation about my family NOTHING bothers any of US. PS all 4 paid our own way thru college We all just laugh and SMILE when together ! I remember family vactions at outerbanks NC. The NY folks enjoyed the ocean. My Sister said please help me swim in the waves.
Indeed. Nowhere in your comment do you mention money. A simple life is great
Hi Sam, Always make Mothers and Women Happy on vacation.
We are at Waikoloa beach in 2 bedroom, 2 bathroom condos for 7 months at $6000/month.
Scuba is excellent , 1000 steps to beach or shops, ocean 80F, pool at condo complex epic.
Keep Smiling
Sounds good! Too bad there’s more than two of us for a 2 bedroom.
Enjoy!
There are so many options in Honolulu besides spending $24,000 a month or staying with family! For example, I messaged you several months ago about our Honolulu condo that had availability for the summer. It has everything your wife wants. Two bedrooms, air conditioning, a recently remodeled kitchen, and washer/dryer. There’s also a very large salt water pool, a separate kiddie pool, a tennis court, a pickleball court, and hot tub. It’s walking distance to the Punahou campus. All for $3500/month.
This post isn’t actually about spending money; instead, it’s about the psychology of what we feel we “deserve” or what is “good enough” for us and our family once we achieve a certain level of wealth. And, the feelings that come up when we *could* afford the really nice thing but instead choose the cheaper option. Is it shame? Embarrassment?
I see this mindset in the wealthy a lot. “It’s either $24,000 a month or nothing!”
Just to be clear, no hard feelings! I love your blog, am reading your first book right now, and find everything you write about thoughtful and interesting. But, it didn’t surprise me that you never expressed interest in our condo. I suspected it was far below what you pictured as “appropriate” for your family for 5 weeks, given your level of wealth and success.
I sincerely hope that you have a wonderful visit in Honolulu and create many cherished memories. Aloha!
Hi Aly! Did I not respond? If not, apologies as I get so many emails and I was in the thick of selling my old house and recording and marketing my new book. But I think I did respond and will check my archives.
Pls resend if you don’t mind.
2 bedrooms is tight for our family of 4, for 5 weeks, as our alternative is 3 bedrooms at my parents house. Plus, they have a 2-bedroom ADU I want to work on cleaning up to make habitable again. But if your place is still open, I’ll talk to my wife.
Our daughter is a poor sleeper, and will wake up whoever is in the room with her.
To me, “nothing” is actually a nice alternative of staying with my parents’ with three free bedrooms. I would gladly pay $5,000-$8,000 for a 3-4 bedroom house for a month, but I can’t find it. If you see anything, please let me know.
Thx
What’s interesting is that you are damned if you choose to live with your parents, and now you are damned if you don’t take a two bedroom option that you don’t think would work for your family. If you said you are going to rent for $24,000 a month, there will be people who say that’s a waste and you are out of touch with reality.
This is why I never share my plans because people can’t help but judge. So kudos to you for doing so!
If I live in a 5-bedroom house, for example, I’m not going to rent a 2-bedroom place for 5 weeks. Maybe 1 week, but not 5.
True. But being judged for your decisions and how you spend money is pretty fun too, if you’re secure either way your own values. There are always blind spots to discover.
I do believe in the benefit of building and operating in silence. But from time to time, it’s fun to share some dilemmas.
Or, at the very least, the responses from others makes some juicy blog meat for a follow-up posting!
Indeed! Here’s the follow up post: https://www.financialsamurai.com/the-choices-we-make-to-achieve-financial-freedom-arent-for-everyone/
No worries. Maybe you did respond, and I missed it. Either way, the condo is no longer available. I hope you didn’t take offense or misinterpret what I meant by “nothing”. I was only referring to the lodging options. The time with your parents is priceless, and the six of you will create many lifetime memories while living together for 5 weeks!
Our extended family is in a similar boat with being “split” between Honolulu and CA, and we’re constantly juggling how to spend as much time together as possible but not drive each other nuts. Do we stay together during visits or rent a separate place, etc? That’s why I find your writing and decision-making on this topic particularly interesting.
Take care!
Hi!
I read your article and I think there are a few points I have observed after living so long in this country.
1. Words like cheap and thrifty have a very negative connotation. Which is sad because it makes people spend beyond their means so those words aren’t attached to them.
2. People want what others have. This country is based on climbing up and looking good. And the way to that is follow the people who have it.
3. This country is about consumption, greed, materialism and capitalism. Hence, what counts is not morals, ethics or values but what you have, where you live and who you know.
Sorry to be so pessimistic but it’s what I have observed. I love it here but I yearn for Asia at times. And by the way, I myself have gotten caught up in all the above at times.
Thank you for your newsletter- look forward to it every Sunday!
Happy Memorial Day,
K
Like you, I’ve shelled out some big(ish) bucks on a vacation rental for 2 months a year. The motivation? So sick of the extra long New England winter, just gotta get outta there and sit on a beach! And like you, I also use Empower/Persona Capital’s site that aggregates all of my assets and costs. Highly useful is the retirement planner that allows me to input a sizable yearly vacation cost. Ultimately, even with the vacation cost, we’re still tracking only a 1-1.5% retirement drawdown and a 99% chance of having money if I make it to 99. We’ve looked at the option of buying vaca home, but that has some major costs. But maybe someday.
As someone here said, why not spend the money if you have it?
At 64 my wife and I stopped renting for summer vacation and went back to camping like we did when our four children were young. Yes camping. In a tent trailer. But it has all the amenities even thought we dry camp and we couldn’t be happier. We did this not so much because of the cost savings over time. But for personal satisfaction, familiarity and the ability to pretty much vacation anywhere New England. Not in winter of course.
We like to go to the ocean in summer and often spend most of the day right on an uncrowded beach that that would have cost more than a thousand a night to have the privilege of staying in a house on. I suppose it would be nice to wake up and walk out to the beach, not having to drive a short distance from where we camp for $35 a night. But to stay in a foreign place (our tent camper is a home one wheels) and try to relax on vacation knowing I poured thousands down the drain doesn’t sound appealing.
This is a very typical male approach to be largely focused on cost. It’s great to be mindful of cost, absolutely. And good to spend time with family, yes absolutely.
What this lacks is BALANCE. Five weeks with anyone’s parents, especially in laws in your wife’s case, is asking a LOT. If you can’t see that, please, please take a step back and think about what the two most important matriarchs in the family do every day both seen and unseen. Chances are there will be hundreds of things that don’t even come to mind because they make it all happen when you’re doing something else. And that doesn’t even cover the amount of work involved with preparing for four people to come stay in your home nor the amount of planning it takes to essentially move and relocate a family with kids.
Women are way more attuned to the reality of cohabitation challenges than men. At the very least, I strongly suggest you find somewhere else to stay for less money for at least 1/2-2/3 of that five weeks. Otherwise, you will wind up with a very unhappy wife and a very unhappy mother by the second week. They may both grin and bear it in front of you as they try and keep up appearances, but inside they will feel you didn’t take their feelings and needs into full consideration. I would wager that the 2 men here are likely not doing any of the work preparing for this trip but the 2 women sure as heck are. You have two incredible women in your family who likely don’t ask for much. Balance will go a loooong way.
Thanks for the suggestion.
“ This is a very typical male approach to be largely focused on cost.” Do you think this is correlated with a person who earns trying to be more frugal since they spent the time and energy?
Did you have an unpleasant experience living with the in-laws as to the reason why you feel strongly about this dilemma? I’m always curious to hear about other people’s experiences to gain better perspective and solutions.
I wonder how much of this disdain for living together is due to cultural differences. In Latin America culture, for example, living with your parents for a visit would be welcome and expected. To not live with your parents or in-laws might be an offense.
If the male is the only income earner, it’s fair for him to be concerned about cost. And if the partner cared about the household finances, she would also be concerned about costs.
I’m a wife and mom. I agree. If your wife doesn’t feel comfortable with this arrangement, it’s not fair to make her deal with it so you can- have 2.6m instead of 2.5m for your kids in ten years? I am in a similar situation every year. Instead of conditions for the whole family, I am getting just a hotel room for myself, and a kid or two can stay with me off and on. Or my husband for some date night. We are middle aged at this point, and I don’t want to be an elderly woman’s houseguest for weeks at a time. It’s not offensive to family to need your own space at this (or any) life stage. A 24k house isn’t the only option between something and nothing.
Sam – thank you for this thoughtful piece – love the intersection between personal finance and the tendencies of humans. So much of what people do is a reflection of them, their historical experiences/family/influences. The priorities and choices made are rational to them but at times, not others. Your piece reflects your own journey.
Thank you for all you bring to the table.
Split the trip: spend half the time at your parents’ house and the other half at a nice resort. A beachfront hotel room with a private master bedroom and a full kitchen will likely cost less than the expensive rental house you were considering. It’s important to think about everyone involved. Does your wife really want to spend four full weeks at her in-laws’ place? No way, let’s be honest. And your mom? She likely doesn’t want a packed house for that long either. A change of scenery also keeps the trip feeling fresh, like getting two vacations in one! Start your time at your parents’ home, and by mid-trip, everyone will be ready for something different. Then you can wrap things up at a beautiful resort, relaxed and happy. Win-win!
Indeed! And something we plan to incorporate with weekends at a beach house and maybe one weekend at a resort.
Some folks are viewing this situation as torture. But this is just staying in a comfortable, not fancy house in a location that’s as close to paradise on Earth as possible!
I don’t view it as torture. I suspect your kids will love it and always remember the time with their grandparents. My question would be, you mentioned your wife simply wanting a place where can plan and cook meals. Are $20K options the only true options, or is that because of your own taste? I’ve stayed in Honolulu and there were many many options in the $4-8K / month range that would likely suit your wife’s needs. Most include pools, albeit not private house pools. Just curious how yours and your wife’s differing tastes and standards may play into this.
I’ve looked and I cannot find any $4-8K/month options for a 3 bedroom condo or home for a month in Honolulu. I was surprised, as I also stumbled across a lot of fake listings. Maybe I’m not looking hard enough.
Please send me some listings if you can.
Or another alternative that works for my family: kids stay with grandparents, parents get a hotel. Cheaper than renting a whole house, wife gets privacy, Grandma gets less hosting responsibility/pressure but still gets quality grandkid time.
At first I thought $24k for 5 weeks was OUTRAGEOUS.
Then … I remembered our 15 day June 2024 river cruise vacation in southern France (including both pre-cruise and post-cruise extensions, and 2.5 days of independently arranged private driver guided touring) – which was at LEAST 10% more costly than your 5 week vacation rental! I’m assuming 10% minimum, since I still haven’t yet tallied up the entire cost of that trip – I think I don’t really want to know! LOL
I guess the cost didn’t feel soooo painful because I made payments over time (10 payments over the course of December 2022 through January 2024, plus 3 additional payments on the days of our independent private touring)?
We do fly premium economy cuz we are a bit large to comfortably fit into those cattle car class regular economy seats. (Tried flying business class once, but still couldn’t sleep on the plane even in the lay flat seat, so can’t justify that extra cost.) And the cruise fare was probably more expensive than necessary cuz we splurged for a veranda suite (for the larger sized shower; did I mention we are a bit large? have you ever used the tiny showers in a regular stateroom??? It was nice to have separate living and sleeping areas).
If you can’t bring yourself to rent the $24k vacation home for 5 weeks, at least spend weekends at a resort hotel that’s not too far from where your parents live (your aunt’s place seems too far away – who wants to spend all that time driving back and forth across the island?). Get a hotel suite with separate sleeping areas for the adults and children. Give Sydney a break and order room service. ;)
It’s actually $24,000 for 4 weeks. We’ll be in Honolulu for 5 weeks. So even more expensive!
My aunt’s beach house is about 50-60 minutes away, not bad. We’d pick up the kiddos from summer school and drive another 35-45 minutes there.
I think we can do it! And if we can’t, we can always rent a place last minute.
Your river cruise sounds fun! We’ll try it in the future.
Re: Renting a place last minute
A VERY good backup plan!
Re: River Cruising
Yes, we did enjoy our first river cruise so much that we went on another one this past March (round trip from Amsterdam). The weather was quite a bit colder than I would have liked, but our schedule didn’t have much leeway regarding dates.
The shore excursions were a bit brutal for us mostly sedentary, out of shape old fogies, but we did have a good time. Exhausted, but good time.
I would set a percentage of net worth that you are willing to spend each year and stick to that. If you don’t spend more than 4% of net worth but have income outside of investments coming in, you are doing fine. Our spending meets this criterion – I work full time and spend less than 4% of net worth – so on net we are still building net worth.
The kids won’t remember where you stayed in 10 years – just that they got to create memories with their grandparents. Staying there creates an organic experience instead of structured visits. Treasure the time and the savings! My young kids don’t have any living grandparents on my side or my husband’s- that is what money can’t buy.
Beautifully said. You’re absolutely right — it’s the love, laughter, and time spent together that leaves the biggest impression, not the accommodations. An organic, lived-in experience with grandparents is priceless.
I’m sorry your kids don’t have living grandparents to share those moments with. But at least they have you. All the more reason to treasure every multigenerational moment we get.
Thx for commenting
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
This is a line to tread carefully my friend, especially when someone like Sam’s wife is not in a traditional 9-5pm but it likely working her — off in the background. Actually, I guarantee she is because they have two young kids. The amount of mental load most mothers carry and all the thousands of “invisible labor” things they do is worth a boat load of money that may not have a tangible dollar value but should and is absolutely vital to the survival, well-being, and functioning of a family’s household and operations. And staying five weeks is a huge undertaking in my opinion.
I believe this trip expense is something that should come out of a shared pool because it affects the whole family unit. She’s going to be more uncomfortable because it’s not her parents, it’s his. I like my in laws well enough, but I don’t feel the same level of comfort around them as I do with my own parents. I feel very out of place when we go to their house but if it’s my parents house it’s not as big of a deal because that’s literally where I grew up. That’s just how it is. So her agreeing to go for that long says a lot.
If she was asking to spend $24k to go on a different trip with her girlfriends, then that would make much more sense to come out of her own funds or for her to be more flexible with finding something a lot less expensive if it’s coming out of the shared pool and he disagreed with the cost. But it sounds to me like she was flexible on price anyway.
I understand what you’re saying about how money feels different when it’s your own money. And everyone’s family is different. I just think it’s asking a lot to live with in laws for that long. I personally couldn’t do it. I’d go for a week max and then fly home first if everyone else wanted to stay.
What’s the longest you, Sam, and anyone else would willingly go live with yours? Yeah, enough said.
The mental load is a good issue to point out for mothers. Never underestimate it. She handles pretty much all the kids logistics, signups, scheduling, doctors visits etc. and of course, she edited my book and helps update my archives to keep them fresh, as well as does the site’s finances.
I’ve tried to reduce her mental load by helping her be free from work since 2015, earn money and manage the finances to stay free, be a stay at home dad since our first was born in 2017, do all drop offs and pickups, and regularly provide food. On weekends, I like to spend max time with both children to give her 3-4-hour breaks at a time. Being a stay at home parent is hard work, but it’s also gratifying. Time is flying and I want to have the least amount of regret possible as a dad. I can’t imagine being away on business trips for extended periods of time.
At the same time, I’m sure I could do more, like clean the house and kitchen more. This is why I should probably go back to getting up a little earlier to get my writing done to free up more house work. Consistency with housework is key!
To save $24,000, I would be willing to stay with my in-laws for 5 weeks. I’d probably ask my mother-in-law all the things that need fixing in her house and do my best to fix them and hire people to fix them as a project manager. Ever since listening to my HS commencement speech, I’ve had a goal of leaving a place better than I’ve found it.
I like the weekend option away for a break. We shall see how it works out.
How about you? What’s your situation? Is $24,000 a month something you can comfortably afford? If you have a partner and children, is s/he a stay at home parent too? What do you wish they did more of to relieve your mental load? I’m hoping to connect more with stay at home dads as there still aren’t many of us. Thx
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.
You’re not a bad person. Human beings have evolved in such a way that parents tend to love their children more deeply than children love their parents. This imbalance often becomes apparent as children grow into young adults. It serves an important purpose: if children were equally attached, they might never leave home to forge their own paths and start families of their own. Some might argue that this isn’t universally true, as many cultures thrive with multigenerational households. While that’s true, these living arrangements are often shaped more by economic necessity and social structure than by emotional dynamics alone.
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!