After publishing Why We Keep Spending Even Though We Know We Shouldn’t, I realized something important: the real reason I wasn’t willing to spend on a vacation rental this summer is because we no longer have financial freedom. I didn’t think about this fact until after I got a lot of feedback from readers on how I should spend my money.
After buying our latest home, I sold a significant amount of stocks and bonds to pay for it in cash. As a result, our passive income temporarily dropped from around $380,000 to about $230,000.
Given our annual after-tax expenses were around $260,000 at the time, we suddenly had a deficit. And by my definition, financial independence means having enough passive income to cover your desired living expenses.
Justifying the Decision To Save
While writing that post, I justified not spending on a vacation rental for the following reasons:
- It didn’t feel right to spend on lodging when we already had a free place to stay consisting of 3 spare bedrooms.
- None of the rental homes felt like reasonable value, nor were there any sub-$10,000 options with 4 bedrooms.
- We could use that money to invest in our children’s custodial accounts to help them launch in the future.
- The micro-interactions of living under one roof create meaningful bonding opportunities for the grandchildren.
All of those are valid points. But the main reason I didn’t include? I’m on a mission to regain financial independence by December 31, 2027, and spending $24,000 on a rental home we don’t need doesn’t help the mission.
If there’s one thing about me, it’s that I’m relentless when it comes to achieving my goals. Whether it was committing to publish three posts a week for 10 years after launching Financial Samurai in July 2009, or vowing to be a stay-at-home dad for the first five years of both children’s lives, I don’t stop until the mission is complete.
After renting out our house for a year, selling it for a profit, saving more, and reinvesting part of the proceeds, our passive income has rebounded to about $320,000. Hooray for higher yields and interest rates, along with discipline and time!
Unfortunately, with both kids now in private language immersion school, our annual expenses are around $288,000 after tax. That’s about $360,000 gross, meaning we’re still running a ~$40,000 gross annual passive income deficit. At a 4% rate of return, that means we need to accumulate at least $1 million more in investable assets.
When the stock market was tanking in April 2025, we were closer to $2 million behind our investable asset goal.
While I could rebalance our portfolio into more income-producing assets to cover all of our expenses, I’ve long been a believer in growth stocks and private growth companies, especially now in the artificial intelligence space. I want to let those investments run.
Without a steady paycheck to cushion any financial shocks, the main lever I can pull is controlling expenses. So, I made the decision not to spend $24,000 on a four-week vacation rental. At a 4.3% risk-free return, that money could generate $1,032 a year in passive income every year. That’s another step closer to financial freedom.
Yes, having my mom and wife under the same roof for five weeks is a sacrifice. But I also see it as a chance to deepen family bonds, especially between grandparents and grandchildren. Both women are lovely people and I believe in their ability to live harmoniously.
Plus, there’s a separate two-bedroom, two-bathroom unit attached to the house that has gone unused for years. I plan to spend two weeks cleaning and restoring it to livable condition. This desire to make improvements to the property is important for the future.
What Are You Willing To Sacrifice?
When I was growing up in Malaysia, I had friends whose entire families of four lived in studio apartments with bunk beds along the walls.
By comparison, four of us sharing three bedrooms and one and a half baths is hardly a hardship. If I can successfully clean up the two-bedroom ADU, then we should have more than enough space to co-habitate for five weeks.
Let’s not forget, we’ll be in Hawaii, not Kabul, Afghanistan. To me, it’s as close to paradise on Earth as you can get. I imagine some people might even scoff at the idea that staying in Hawaii for five weeks in a free home could be considered a “sacrifice” at all. In many cultures, this is the norm.
There are plenty of people who can’t take five weeks off work. Some can’t even take two. And many who do take time off end up staying local to save money. My wife and I are both currently DUPs and fortunate to have a free place to stay. This is what my grandfather, may he rest in peace, envisioned when he built the house—for generations of our family to enjoy.
So no, there’s no room service, no pool, Toto washlet, and no 1000-thread-count sheets. Big deal. I’m willing to forgo luxuries to inch closer to our goal of being financially independent again.
Nothing will stop me because I know how amazing it felt to be completely financially free for the 11 years after I left my day job in 2012. I’m sure my wife feels the same way when she engineered her layoff in 2015.
Think of the Alternatives to Feel More Appreciative
Whenever I start feeling dissatisfied about not having the “perfect” situation, I remind myself to think about the alternatives. Doing so always helps me feel more grateful for what I have. Here are our realistic alternatives:
- Having another staycation in San Francisco, Sonoma, or Tahoe (not bad, but not Hawaii)
- Missing out on experiencing a new school that our kids might attend for high school, since their current school ends at 8th grade
- Commuting downtown to work 50+ hours a week under fluorescent lights, trying to climb the corporate ladder
- Traveling for business for weeks at a time (a temporary escape, perhaps, but at what cost?)
- Getting micromanaged by an insecure boss and berated by demanding clients
- Working until 10:30 p.m. during month end almost every month at my wife’s job
- Having to go to war to fight for our country’s freedom and then dying
- Wishing I had spent more time with my parents after they are gone because we stayed in our own place instead of with them
When I lay it all out like this, spending five weeks with family for free in Hawaii sounds pretty great. We’ll be spending the weekends at my Aunt’s beach house or at a hotel to break things up.
More Choices I Made to Achieve Financial Freedom
Choosing not to spend on a rental house in Hawaii this summer is just one decision to help re-achieve financial independence. Here are some of the choices I made the first time around:
- Lived in a studio apartment with a roommate in Manhattan for two years to keep rent down while building my career.
- Shared a bedroom with my girlfriend in a 2-bed, 1-bath condo in a noisy part of San Francisco for a year to save more aggressively.
- Saved and invested every bi-weekly paycheck for 13 years, and invested over 90% of each year-end bonus I received to maintain a 50% – 80% saving rate.
- Attended business school part-time for three years for 20 hours a week while working ~60 hours a week in finance to save time and money.
- Woke up by 5 a.m. to write on Financial Samurai for 2.5 years before heading to the office by 6:30 a.m., then wrote for another hour after 9 p.m.
- Bought a second-hand Land Rover Discovery II named Moose for $8,500 and drove it for 10 years instead of splurging on a new car like all my friends.
- Postponed having children by 3–4 years because I was too focused on my career and wanted to reach a target net worth first. This is one of my biggest regrets, waiting so long as an older parent.
- Downsized to a smaller and 40% cheaper home in 2014 to save money and boost semi-passive income by renting out our previous home.
- Skipped out on a a couple of dad’s nights out partly because I didn’t want to pay $500 for NBA tickets and dinner or be away from family for a weekend in Mexico.
Some of you may not agree with the choices I made, and that’s perfectly OK. You’re not me. Looking back, I’m grateful for most of them because they gave me the ability to negotiate a severance and break free at age 34. I just wished I focused on family planning sooner.
The value of financial freedom far outweighs any of the sacrifices I made along the way. It’s not even close.
The Joy of Saving and Investing
Here’s what many people may also not realize: for personal finance enthusiasts like me, saving and investing itself brings joy. The more I save and invest, the more satisfaction I get as a father. So, skipping the $24,000 rental or the $2,000 first-class plane tickets doesn’t feel like deprivation, it feels like progress.
Every night we stay at my parents’ house is another $800 saved. That brings me far more happiness than lounging in a luxury rental, doom scrolling why stagflation is a key risk to the president’s latest tariff policies.
In Hawaii, I’d much rather be outdoors—boogie boarding, snorkeling, hiking, playing pickleball or golf—than sitting inside. In fact, the dumpier the place, the more incentivized I am of getting out of the house!
Personal Choices for Personal Goals
The choices we make in pursuit of financial freedom are deeply personal. You can’t tell someone how to spend their money if you wouldn’t spend your own that way.
Some think I’m sacrificing too much. I think I’m receiving a gift—five weeks in Hawaii with my family, free lodging, and a chance to move closer to my financial goal. Sounds like a win to me.
And when I reach my financial freedom goal by December 31, 2027, I won’t look back with regret for not spending $24,000+ on a rental house. Instead, I’ll appreciate the time we spent together, no matter how inconvenient some moments may have been. At the end of the day, being together with family is the most important thing.
Readers, what choices are you making to achieve financial freedom sooner? If you’re already financially independent, do you view these decisions as sacrifices—or simply no big deal? And as we get older, is it natural to lose appreciation for what we have?
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Source: The Choices We Make To Achieve Financial Freedom Aren
