On October 8, 2025, we decided to take a family vacation, but I wasn’t excited about it. All week long I was supposed to be attending the Fairfield Challenger Tennis Tournament with my good friend Richard. September and October are Bay Area tennis havens, with multiple tournaments and ideal weather. This year’s Laver Cup is particularly exciting.
However, October 9th and 10th happen to be my children’s school holidays, followed by Columbus Day on October 13th. My wife and kids really wanted to go to San Diego and visit Legoland and SeaWorld for the first time.
I, on the other hand, would be more than happy to stay home, save about $5,000, and enjoy watching professional tennis, one of my absolute favorite activities, for only $45 or less per ticket. But being the frugal tennis fanatics we are, we actually volunteered to be caddies, get in for free and get a free lunch. However, the greatest pleasure is having the absolute best seats in the stadium!
Before having kids, I used to fly to New York to visit my sister and watch the U.S. Open in Flushing. I can go from 10am to 10pm and not miss a beat. But after becoming a parent, I could no longer justify this indulgence.
I don’t like flying very much
I don’t like flying because of the queues, delays, high fees, and sometimes unruly passengers. I’ve taken about 200 work flights over 13 years and experienced every kind of travel pain imaginable. Honestly, I still think about death every time I get on a plane. The trauma of 9/11 will never fully go away. I lived a few blocks away and had attended a meeting at the top of the North Tower earlier that year.
If I were to fly, I’d rather go to Honolulu to visit my parents than wait in long lines at an amusement park. But I also knew these trips weren’t really for me, but for the kids. So off we went, me reluctant but outwardly enthusiastic.
Oh, how I envy those parents who really love Legos, roller coasters, and Disney characters. They look like they are having the time of their lives! Life really is better when you have more interests.
So here I am – a reluctant, slightly grumpy dad – sharing my thoughts before take off on why you should take as many vacations as possible While you’re still working.
Why the holidays aren’t so great after early retirement
In my last post, I discussed how literally “fire” can be scary for a startup. Here are three reasons why the holidays lose their magic after early retirement.
1) You take freedom for granted
The “problem” with FIRE is having unlimited freedom and choice. On the surface, no boss, no meetings, no deadlines sounds incredible. But in reality, too much freedom can feel like a burden. Deciding what to do with your time can feel incredibly heavy when every option is available.
Every weekday, after sending the kids to school, I have complete freedom to spend my day. I could play tennis, write, nap, go hiking, or do nothing. No one told me what to do or how to do it. However, when every day feels like a vacation, The novelty will eventually wear off.
After 13+ years of freedom, I didn’t wake up excited about being able to do anything I wanted. Autonomy has become my default, not a luxury. What once felt like freedom is now just yes. That’s the paradox of early retirement: The more freedom you have, the less you notice it.
To combat this complacency, I find it crucial to maintain a sense of structure and challenge. This is one of the reasons why since July 2009, even after leaving my job in 2012, I have maintained a writing schedule of 3-4 times a week. Writing gives me a sense of purpose and responsibility that pure leisure cannot provide.
Without some form of productive struggle, the days become a blur and even heaven begins to lose its luster.
2) It’s hard to spend money on entertainment when you’re already happy
Fire will make you reluctant to spend money on leisure. It’s like paying extra for tap water, you already get the water you need.
After more than 13 years of financial freedom, I’ve discovered many inexpensive activities that bring me joy: playing tennis, pickleball, writing, hiking, and watching tennis.
So spending $5,000 on a trip that I’m not interested in doesn’t feel good. I’d rather use my kids’ school holidays to give them tennis and soccer lessons (for free) and then play on a giant whirlpool slide in the pool (taking advantage of my underutilized sports club membership, which costs $180 a month). Dad Day Camp to the Max!
Additionally, I recently spent three weeks dealing with tenant turnover, which is always unpleasant. I had to list the property for rent again, clean up what I could show, evaluate potential tenants, draft new leases, help with onboarding, and coordinate move-out and cleanup with the departing tenants. I felt uncomfortable after spending so much effort and spending more than half a month’s rent on one trip.
If you’re the one in charge of your family’s finances, you can’t help but think about a cost-benefit analysis. But it’s important to consider other members of the family and what they want to do. Since I turn 45 in 2022, I’ve been trying to spend more money.
3) Your vacation property may not be as nice as your home
Another frustrating issue after a fire: Vacation properties are often not as nice as your primary residence. This also applies to most furloughed workers.
You could spend a fortune renting a fancy place, but you probably won’t because that’s not what most FIRE practitioners think about. We spent several years saving aggressively and avoiding oversaving. The idea of paying thousands of dollars to rent a home for a week, let alone a day, goes against that condition.
Instead, you might choose a shabby Airbnb or hotel room for everyone to stay in. Only the truly wealthy, the top 0.1%, would rent a vacation home as good as their own. Spending money is much easier when you have a lot of active income coming in.
If you recently bought a home that you love, you’ll also be less willing to leave it. I love our home – the Toto washlet, the views, the spaces inside and out. Every day feels like staying in a luxurious vacation home. So when we left, our current home was empty and it didn’t feel comfortable to spend the money to downgrade.
Remember, the true cost of a vacation is the cost of the vacation plus the ongoing costs of maintaining your existing home. Here’s my holiday spending guide to help you spend more responsibly while out and about. It’s easy to go crazy in vacation mode.
when is the holiday yes Better to retire early
The holidays after the fire are the most exciting If you have never traveled before. If your parents never took you anywhere, your job never allowed you to travel, and you never studied abroad, then by all means travel! You will finally have the freedom and means to explore.
Hopefully you’ll be able to visit multiple continents, immerse yourself in new cultures, and realize how lucky we are in the United States. The world would be a better place if more people traveled and shared good food with people from completely different backgrounds.
Once you’ve broken bread with someone, it’s hard to hate them.
Sadly, since I have lived abroad for 13 years, the joy of traveling has disappeared for me. As the child of a diplomat, I lived in six countries, studied abroad my junior year, worked in Asia and the United States for 13 years, and checked off sights like Angkor Wat, the Taj Mahal, the Blue Mosque, the Colosseum, and the Hermitage on my bucket list.
Of course, I would still love to visit Cairo and Petra, but they can wait until our kids are older.
The best vacation is when you’re still working
If you’re still working towards financial independence, enjoy the incredible privilege of getting paid while on vacation. It’s the same joy as having paid parental leave. What a wonderful job that comes with benefits that shouldn’t be taken for granted.
So, take advantage of all your vacation time. Don’t hoard them because you’re worried about losing your job or missing out on a promotion. The only exception is the last year before FIRE. Save these days because when you leave, your employer will have to pay you in cash.
The more you are micromanaged and disrupted at work, the more you will enjoy your vacation. Paid time off feels like sweet revenge for all the crap you put up with. But once no one tells you what to do, the holidays lose that contrast. You don’t run from anything anymore.
You’ll still have a great time while out
Even though vacations are less exciting after early retirement, I still enjoy the freedom to travel whenever and wherever I want. I revisited this article after returning from Legoland and SeaWorld, and you know what? I had so much fun!
But more importantly, our children had the best time of their lives. They told their mom and me, “This is the best time ever.” This feedback is truly priceless.
As a FIRE parent, it’s great to not have to take time off from school when your kids have the day off. I didn’t fully appreciate how much of a privilege this was until I realized how many working parents were scrambling to find child care while working at random schools.
If you want to retire early but are concerned that kids will disrupt your ideal after-get off work lifestyle, don’t worry! Kids these days have many days off from school, and between local holidays, federal holidays, and service days, you’ll have plenty of time off to travel. We are talking about 3.5 – 4.5 months of vacation a year, which is more than enough.
Do the hard things in retirement to better enjoy your vacation
If you want to get excited about vacations again in retirement, do something challenging in retirement. Juxtaposing the hard with the easy helps to better appreciate the good life.
For me, it’s writing a book because writing an article is no longer difficult. Each book takes about two years to complete, and by the time I publish Millionaire Milestones: Easily Reach Seven Figures In May 2025, I felt extremely relaxed and accomplished. It even makes USA Today National bestseller list. This won’t be easy, as there are only 100 spots for all genres, while more than 300,000 books are traditionally published each year.
This achievement made me even more motivated to go on vacation to Honolulu for five weeks because I felt like I Well deserved it. Of course, it wasn’t a completely relaxing trip. I was transforming my parents’ in-law unit, confronting difficult childhood memories, and trying to prove my Hawaiian heritage. But this time, the vacation feels more meaningful because it comes after a period of hard, creative work.
Don’t think that retiring early will lead to a life full of exciting vacations. You might be traveling like crazy at first, but eventually the novelty will wear off and you’ll start craving productivity and purpose again. Enjoy good balance!
Reader questions
Fellow retirees, are you finding that the holidays are less exciting because every day feels like a vacation? Are you taking less of your trip than you originally planned, or are you exhausted because it was too hard in the first place? Once you’ve discovered the many cheap ways to enjoy life at home, will you spend money on new adventures?
Do you think vacations are really that much fun once you no longer have to escape work?
If you want to have a permanent vacation
If your goal is to one day live like you’re on a permanent vacation, you need to save and invest diligently while keeping track of your finances closely. Freedom without financial transparency can easily turn into hidden stress.
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