On October 8, 2025, we decided to go on a family vacation I was decidedly unexcited about. That entire week was supposed to be my time to attend the Fairfield Challenger tennis tournament every day with my buddy Richard. September and October are tennis paradise months in the Bay Area, with multiple tournaments and ideal weather. This year was especially exciting with the Laver Cup in town.
However, October 9 and 10 happened to be school holidays for my kids, followed by Columbus Day on October 13. My wife and children really wanted to visit San Diego to see Legoland and SeaWorld for the first time.
I, on the other hand, was perfectly happy to stay home, save ~$5,000, and enjoy watching professional tennis, one of my absolute favorite activities, for $45 or less per ticket. But as frugal tennis fanatics, we actually volunteer as ball boys to get in free and get free lunch. However, the biggest joy is having the absolute best seats in the house – right on the court!
Before having kids, I used to fly to New York City to visit my sister and watch the US Open in Flushing. I could go from 10 a.m. to 10 p.m. without missing a beat. But after becoming a parent, I could no longer justify that kind of indulgence.
My Great Dislike Of Flying
I dislike flying due to the lines, the delays, the costs, and sometimes unruly passengers. After taking around 200 work flights over 13 years, I’ve experienced every kind of travel misery imaginable. And if I’m being honest, I still think about death every time I board. The trauma from 9/11 never fully fades. I lived just a couple blocks away and had attended a conference at the top of the North Tower earlier that year.
If I’m going to fly, I’d rather it be to visit my parents in Honolulu, not to stand in endless amusement park lines. But I also know these trips aren’t really for me, they’re for the kids. So off we went, me internally reluctant but outwardly enthusiastic.
Oh, how I envy those parents who genuinely love Legos, roller coasters, and Disney characters. They look like they’re having the time of their lives! Life really is better when you have more interests.
So here I am – the reluctant, slightly grumpy dad – sharing my thoughts before takeoff on why you should take as many vacations as you can while you’re still working.
In a previous post, I discussed how being truly FIRE is terrible for entrepreneurship. Now here are three reasons why vacations lose their magic after early retirement.
1) You Take Your Freedom for Granted
The “problem” with FIRE is having endless freedom and choices. On paper, that sounds incredible with no boss, no meetings, no deadlines. But in reality, too much freedom can start to feel like a burden. When every option is available, deciding what to do with your time can feel oddly heavy.
Every weekday after dropping my kids off at school, I have total discretion over my day. I can play tennis, write, nap, go on a hike, or do absolutely nothing. There’s nobody to tell me what to do or how to do it. Yet, when every day can feel like a vacation, the novelty eventually wears off.
After 13+ years of freedom, I don’t wake up excited by the idea of being able to do whatever I want. Autonomy has become my default setting, not a luxury. What once felt liberating now simply is. That’s the paradox of early retirement: the more freedom you have, the less you notice it.
To counteract this complacency, I’ve found it’s essential to maintain a sense of structure and challenge. That’s one reason why I’ve kept up a consistent 3–4X per week writing schedule since July 2009, even after leaving my job in 2012. Writing gives me a sense of purpose and accountability that pure leisure can’t provide.
Without some form of productive struggle, the days can blur together, and even paradise starts to lose its shine.
2) It’s Hard to Spend Money on Fun When You’re Already Happy
FIRE can make you reluctant to spend money on leisure. It’s like paying extra for tap water, you already have access to what you need.
After more than 13 years of financial freedom, I’ve discovered plenty of inexpensive activities that bring me joy: playing tennis, playing pickleball, writing, hiking, and watching tennis.
So spending ~$5,000 on a trip I’m not excited about doesn’t feel great. I’d rather have used the kids’ school holidays for giving them tennis and soccer lessons (free), followed by a pool day with a big swirly slide (utilizing my underutilized sports club membership that costs $180/month). Daddy day camp to the max!
In addition, I had 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 for showings, evaluate prospective tenants, draft a new lease, help with onboarding, and coordinate with the departing tenants on their move-out and cleanup. After all that effort, to then spend more than half of one month’s rent on a trip felt uncomfortable.
If you’re the person responsible for your household finances, you can’t help think about cost-benefit analysis. But it’s important to think about the other members in your family and what they want to do. Since I turned 45 in 2022, I’ve being trying my best to spend more money.
3) Your Vacation Property Likely Won’t Be as Nice as Your Home
Another post-FIRE downer: the vacation property usually isn’t as nice as your primary residence. This pertains to most workers who vacation too.
You could spend a small fortune renting a luxury spot, but you probably won’t because that’s not how most FIRE practitioners think. We spent years saving aggressively and avoiding excess. The idea of dropping thousands to rent a house for a week, let alone a day, goes against that conditioning.
Instead, you’ll likely settle for a modest Airbnb or hotel room, cramming everyone in. Only the truly wealthy, the top 0.1%, would rent a vacation home as nice as their own. When you’ve got lots of active income coming in, it’s much easier to spend.
If you’ve recently bought a house you love, you’ll also be more reluctant to leave it. I love our home – the Toto Washlets, the view, the space inside and out. Every day already feels like living in a luxurious vacation property. So paying money to downgrade feels off while our existing home sits empty while we’re away.
Remember, the true cost of your vacation is the cost of your vacation plus the daily cost of maintaining your existing home. Here’s my vacation spending guide to help you spend more responsibly while away. It is very easy to go nuts while in vacation mode.
When Vacations Are Better Post-Early Retirement
Vacations are most exciting post-FIRE if you’ve never traveled before. If your parents never took you anywhere, your job never sent you on trips, and you never studied abroad, by all means travel! You’ll finally have the freedom and means to explore.
Hopefully, you’ll visit multiple continents, immerse yourself in new cultures, and realize how fortunate we are in the U.S. The world would be a better place if more people traveled and shared meals with those from completely different backgrounds.
It’s hard to hate someone once you’ve broken bread with them.
Sadly, the thrill of travel has faded for me because I grew up living abroad for 13 years. As a foreign service officer’s kid, I lived in six countries, studied abroad my junior year, traveled throughout Asia and the U.S. for work for 13 years, and checked off bucket-list sites like Angkor Wat, the Taj Mahal, the Blue Mosque, the Colosseum, and the Winter Palace.
Sure, I’d still love to visit Cairo and Petra, but they can wait until our kids get older.
The Best Vacations Are When You’re Still Working
If you’re still working toward financial independence, enjoy the incredible privilege of getting paid while on vacation. It’s the same joy as receiving paid parental leave. What wonderful work benefits that should not be taken for granted.
So take all your vacation days. Don’t hoard them out of fear you’ll lose your job or miss a promotion. The only exception is your final year before FIRE. Bank those days since your employer has to pay them out in cash when you leave.
The more you’re micromanaged and undermined at work, the more you’ll enjoy your vacations. Paid time off feels like sweet revenge for all the nonsense you put up with. But once nobody’s telling you what to do, vacations lose that contrast. You’re not escaping anything anymore.
You’ll Still Have Fun While Away
Even though vacations aren’t quite as thrilling after early retirement, I still appreciate the freedom to travel whenever I want. I’m revisiting this post after returning from LegoLand and SeaWorld, and you know what? I had a blast!
But more importantly, our kids had the time of their lives. They told their mom and me, “It was the best time ever.” That kind of feedback is truly priceless.
As a FIRE parent, it’s nice never having to ask for time off when your kids are on break. That’s a privilege I didn’t fully appreciate until I realized how many working parents scramble to find childcare during random school in-service days.
If you want to retire early, but are afraid kids will spoil your ideal post-work lifestyle, don’t worry! Kids nowadays have so many days off from school, between local holidays, federal holidays, and in-service days, that you’ll have plenty of days off to travel. We’re talking 3.5 – 4.5 months off a year, which is more than enough vacation time.
Do Hard Things in Retirement To Better Appreciate Vacations
If you want to get excited about vacations again in retirement, do something challenging in retirement. It’s helpful to juxtapose the hard with the easy to better appreciate the good life.
For me, that’s been writing books because writing articles is no longer hard. Each book takes about two years to complete, and when I published Millionaire Milestones: Simple Steps to Seven Figures in May 2025, I felt a tremendous sense of relief and accomplishment. It even made the USA TODAY national bestseller list. Not easy when there are only 100 spots across all genres while more than 300,000 books are traditionally published a year.
That achievement made me more motivated to vacation in Honolulu for five weeks because I felt like I deserved it. Of course, it wasn’t a completely relaxing trip. I was remodeling my parents’ in-law unit, confronting difficult childhood memories, and trying to prove my Hawaiian roots. But this time, the vacation felt more meaningful because it followed a period of hard, creative work.
Don’t assume early retirement will create a life full of thrilling vacations. You might go travel-crazy at first, but eventually the novelty fades, and you’ll start craving productivity and purpose again. Enjoy a nice balance!
Reader Questions
Fellow retirees, have you found vacations to be less exciting now that every day can feel like one? Did you travel less than you originally planned, or burn out after going too hard early on? Do you struggle to spend money on new adventures once you’ve found plenty of inexpensive ways to enjoy life at home?
And what do you think – are vacations really that fun once you no longer need an escape from 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 close track of your finances. Freedom without financial clarity can easily turn into hidden stress.
Since 2012, I’ve used Empower’s free wealth management tools to monitor my net worth, manage cash flow, and reduce investment fees. The platform has helped me stay disciplined and organized long after leaving my day job.
If you have more than $100,000 in investable assets, whether in savings, taxable accounts, 401(k)s, or IRAs, you can get a free financial check-up from an Empower financial advisor by signing up here. It’s a simple, no-obligation way to have an experienced professional review your finances and provide objective feedback.
A fresh set of eyes can reveal hidden fees, inefficient allocations, or opportunities to optimize your plan. The clearer your financial picture, the greater your confidence in your path to financial independence. And confidence is what allows you to fully enjoy the freedom you’ve worked so hard to earn.
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