Back on June 30, I published Summer YOLO Fund: Permission To Spend, giving myself explicit written permission to blow through $40,000 in Honolulu this summer.
The $40,000 was originally earmarked for investments in private startups after attending YC demo day. However, I wasn’t able to invest in companies I wanted, whether due to valuations or the round already being full.
So instead of investing the money in public stocks or venture capital immediately, I decided to see if I could actually spend more money than I’m used to.
As someone who has saved aggressively since 1999, when I realized I couldn’t keep getting in at 5:30am and leaving after 7pm my entire career, spending excessively is hard. I’ve averaged over a 50% savings rate for 28 years, first out of a desire for freedom, then out of the need to take care of my family.
I tracked every dollar for 30 days, which was more cumbersome than I thought. I logged the good decisions, and the bad ones.
Final tally: $6,486. That’s 16% of the budget.
I tried my best to spend like a typical American consumer with a 3% saving rate who is OK with working forever for the man. However, I failed, because I didn’t have a legitimate outlet for the other $33,514.
Let me show you exactly where the money went, and more importantly, why it couldn’t go anywhere else. The results also have real implications for those of you saving and investing for retirement today. You simply might not need as much as you think you do to be happy.
How I’m Defining The Two Spending Buckets
Before the numbers, the definitions.
Fundamental spending is anything I’d have paid regardless of the experiment. Basic food, groceries, gas, pharmacy runs, basic transportation. This is simply the cost of feeding and moving a family of four around Honolulu for a month. It has nothing to do with permission. It’s just life.
True YOLO spending is anything frugal-me would have hesitated on or skipped entirely if I weren’t deliberately trying to loosen up. Season passes, splurge meals, gear that was more want than need, the treats that exist purely because I told myself I was allowed.
Flights and three weeks of Iolani and Punahou summer school sit outside both buckets, given we’d have spent on some form of summer camp regardless. But to be thorough, I’ll still include their cost in the total spend for the month further down.
The 30-Day Numbers
$5,266 fundamental. $1,220 true YOLO. $33,514 untouched.
Look at how flat that spending line sits against the budget line. That gap is the entire story of this post.
What Was Actually In The True YOLO Bucket
Here’s every dollar of the $1,220 that counts as a genuine splurge:
Wet ‘n’ Wild season passes for the four of us: $300. We ended up going three times, so that was great value. We’ll go again at least once during the winter.
A brunch at Koko Head Café that was crazy expensive for mediocre food, but I took my parents, who had never been: $196. The congee and skillet dishes ran about $28 each. The only genuinely great thing on the menu was the French toast.
Hanauma Bay entry plus snorkel gear rental: $300. This included bus service and tickets. I was hyped up to go, remembering all the fish I saw as a kid. Sadly, there weren’t nearly as many this time.
Pokémon GO gear and GO Fest event tickets, including a $75 auto-catcher device I already owned one of and left in San Francisco: $145. This turned out to be the most fun splurge of the month. GO Fest is only once a year.
A birthday lunch for my wife at The Kahala’s Plumeria Beach House: $142. We ordered the Kahala Bento Box, butterfish, and French onion soup. So good. Lovely view of the ocean.
Shave ice and gelato, spread across the month: $47. I think I’m missing an entry or two here, but maybe not. Ululani’s and Hawaiian Shave Ice Co. are our favorites.
Aloha shirts and family clothing: $63. I never shop for clothes, but there’s a great Goodwill in Kaimuki, and I needed some nicer Aloha shirts for school tours at Mid-Pac, ‘Iolani, and Maryknoll. Paying $120 for a new Aloha shirt at the mall seemed outrageous next to $9 or less at Goodwill.
Dried plums, a genuinely bad kava drink, and other “why not” island snacks: $27.
What Was In The Fundamental Bucket
The other $5,266 broke down like this:
- Everyday meals, mostly poké from Tamura’s and Fresh Catch, plate lunches, and family dinners: ~$3,400
- Groceries and farmers market produce, heavy on mangoes and lychee: ~$700
- Household and pharmacy runs, including my wife’s Target and Long’s trips: ~$937
- Gas: $176
- One airport rideshare: $53, plus roughly $48 more my dad spent picking us up and dropping us off, which I never formally logged
The Real Culprit To Not Spending As Much: Free Housing
The single biggest reason I couldn’t spend the money is that my housing cost was zero.
We stayed in my parents’ two-bedroom in-law unit, the same one I spent five weeks renovating last summer and another week on this year. A comparable two-bedroom condo in the same Kahala-adjacent neighborhood averages $410 a night. Multiply that out over 30 days and a market-rate version of our stay would have run roughly $12,300, more than double everything I actually spent combined.
Housing is usually the largest line item in anyone’s budget. Once that number goes to zero, everything else becomes small by comparison. A $196 brunch feels reckless in isolation. Against a $12,300 housing expense that’s free, it’s a rounding error.
Hence, the secret to living a comfortable life is fixing your housing costs. That means buying your primary residence as soon as you know where you want to live long term. Once your housing cost is fixed, let alone paid off, life becomes relatively inexpensive.
Why We Skipped The Catamaran And The Fancy Restaurants
We have a 6-year-old and a 9-year-old. That single fact vetoed an entire category of classic YOLO spending before it could even get considered.
No sunset catamaran cruise. No tasting menus. No late dinners at the restaurants that make Honolulu’s food scene exciting. Kids that age don’t want a three-hour dinner with wine pairings. They want poke, shave ice, a pool, and love.
The activities that did work were free. Beach days. Hikes up Koko Head crater and Tantalus. Pickleball. None of it made the spending log because none of it cost anything.
In retrospect, I should have asked my parents to watch the kids for at least one night so my wife and I could go on an evening date. I just didn’t want to burden them, since they always have their favorite shows on between 7 and 9pm. We did manage a couple of lunch dates instead.
The Splurges That Did Happen
We went to The Kahala Resort twice, once for $28 cheeseburgers early in the trip and once for my wife’s birthday lunch. Both were expensive relative to the rest of the log, but neither felt excessive. You even get free parking at the resort if you spend at least $50.
An oceanfront lunch at a five-star resort for $142, birthday included, is the kind of number that makes traditional resort pricing look absurd. You don’t have to sleep there to enjoy it. A two-bedroom suite at The Kahala over 4th of July weekend was going for over $5,000 a night. We even got to wade at the beach near Maya Rudolph and Paul Thomas Anderson, who were vacationing nearby.
Wet ‘n’ Wild and Hanauma Bay were the two purchases I expected to sting and didn’t. $300 for four season passes, used three times, turned into some of the best value of the entire trip. Hanauma Bay ran $300 once gear rental was included, steeper than I expected, but it was a nice bucket-list experience, even if the kids only lasted 25 minutes in the water before getting cold.
Food Was The Only Lever I Could Consistently Pull
Strip out the free activities and the housing, and food is really the only category where spending more was always an option. Better restaurants. More fruit. A second dinner because I forgot we already had poke waiting in the fridge.
Even that had a ceiling. You can only eat so much in a day, and I put on a couple pounds of fat this month proving it. There’s a natural limit to how much money you can convert into calories before the exercise stops being fun and starts being a problem.
The One Splurge I Was Considering
Midway through the trip, during Pokémon GO Fest, I walked into the Panerai store at Ala Moana. I tried on $10,000 to $20,000 watches that looked pretty cool. I used to be really into collecting watches back when I worked in finance, 15 to 20 years ago.
Then I left without buying anything.
It just felt dumb to spend $10,000-plus on a watch to fulfill my Summer YOLO Fund quota when I already had an iPhone that tells time perfectly well. A phone truly is one of the best values money can buy on a material item.
My Two Proudest Expenses
The two purchases I’m proudest of this summer weren’t purchases at all in the traditional sense.
After three years, I finally found the activation energy to fix my dad’s car AC, which wouldn’t blow cool air during the day. I found a mobile mechanic online, he came by the next day, and added a pound of Freon for $80. The alternative was replacing the leaking condenser for $600, which seemed unnecessary for a 28-year-old car. No more unnecessary suffering and potentially passing out while driving. Hooray!
Even more satisfying than not melting, I hired someone to deep clean my parents’ carpets for $425, the first professional cleaning in nine years. It was wonderful to get decades-old stains out of the stairwell and upstairs. My parents paid $385 the last time it was done, so the new price was roughly in line with inflation. My mom also insisted she pay, so there was no cost to me.
Neither of those counts as YOLO spending. Both felt better than anything on the True YOLO list.
Do Flights Count As Fundamental?
I’d argue yes, in the sense that they’re a necessary cost of the trip. But I’ve kept them outside the daily spending log entirely, since they were booked and paid for before the $40,000 authorization existed. You can’t YOLO your way into a trip you were always taking.
For the record: round-trip economy tickets from San Francisco to Honolulu for four came to $2,600, or $650 per person. Add three weeks of summer school at Iolani and Punahou for the kids, $3,890, and the full cost of the month, flights and tuition included, comes to roughly $12,976. Still less than what the housing alone would have cost at market rate.
To be thorough, here’s the total spending for the month once flights and summer school are included.
Even counting every flight and every tuition payment, I still only spent 32% of the $40,000. Free housing did that much heavy lifting.
Lesson #1: Be Happy With What You Have
Spending money on purpose is hard when you’re content.
We didn’t need a bigger place to stay, because we had a simple place for free. The kids were happy with poké and pizza most of the time, and there’s only so much anyone can eat. We didn’t need the catamaran, the tasting menu, or the watch, because none of it would have made the month better than beach days, pickleball, and a one-hour chess game with my dad that ended in a stalemate.
I gave myself permission to spend $40,000. It turns out permission was never the constraint. Desire was, and apparently, desire is very hard to manufacture when you have simple wants and needs.
It’s true that minimalism and early retirement go hand in hand. If you have the capacity to live well below your means for decades, enjoying life after work is relatively easy.
Lesson #2: The Best Life Moments Are With Family
I’ve never beaten my father in chess before, and I still haven’t. But after our second game, I got him to a stalemate, unable to move my king. To me, spending that time with him is priceless. So was watching my kids play with him.
So where did the other $33,514 go, or $27,074 once flights and summer school are counted? It didn’t sit in cash for long. That’s a story for a separate post.
Readers, how much would you be comfortable spending in a single month if someone gave you explicit permission? What’s stopped you from splurging even when you could technically afford to? Do you have a hard time spending like the typical American?
Track Your Own Numbers Before You Try This
Logging every purchase by hand for 30 days taught me something I should have already known: manual tracking is exhausting, even for someone who writes about money for a living. If you want to run your own version of this experiment, or just want a clearer picture of where you stand, let software do the counting instead of your notes app.
I’ve used Empower’s free financial dashboard for years to track net worth and spending across accounts in one place, without any manual logging.
For the bigger question this whole experiment raises, how much do you actually need to feel financially free, ProjectionLab is the tool I’d point you to. It lets you model different net worth, spending, and retirement scenarios so you can see for yourself whether your number is realistic or padded with fear.
If your own retirement number needs a gut check, pick up a copy of my USA Today bestseller, Millionaire Milestones: Simple Steps To Seven Figures. It walks through what to prioritize at every stage of building wealth, so you can figure out your real number instead of just assuming more is always better.
