On October 8, 2025, our family embarked on a family vacation that I was less than thrilled about. That week was meant for me to attend the Fairfield Challenger tennis tournament daily with my buddy Richard. September and October are tennis paradise months in the Bay Area, boasting multiple tournaments and perfect weather. This year was particularly exciting with the Laver Cup in town.
However, October 9 and 10 were school holidays for my kids, followed by Columbus Day on October 13. My wife and children were eager to visit San Diego to experience Legoland and SeaWorld for the first time.
Meanwhile, I was content to stay home, save around $5,000, and enjoy watching professional tennis—one of my favorite pastimes—for $45 or less per ticket. As frugal tennis enthusiasts, we even volunteer as ball boys to gain free entry and lunch. The best part? We get the absolute best seats—right on the court!
Before becoming a parent, I would fly to New York City to visit my sister and watch the US Open in Flushing, spending entire days immersed in the sport. But after having kids, that kind of indulgence became hard to justify.
My Great Dislike Of Flying
Flying has never been my favorite activity. The lines, delays, costs, and sometimes unruly passengers make it a hassle. After approximately 200 work flights over 13 years, I’ve faced every travel misery imaginable. If I’m honest, I still think about death every time I board a plane, a trauma from 9/11 that lingers. I lived just a couple of blocks away and had attended a conference at the top of the North Tower earlier that year.
If I must fly, I’d prefer it be to visit my parents in Honolulu, not to stand in endless amusement park lines. Yet, I understand these trips aren’t really for me; they’re for the kids. So off we went, with me feeling reluctant but trying to appear enthusiastic.
Oh, how I envy those parents who genuinely love Legos, roller coasters, and Disney characters. They seem to be having the time of their lives! Life is undoubtedly more enjoyable when you have diverse 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.
Why Vacations Aren’t As Great Once You Retire Early
In a previous post, I discussed how being truly FIRE is detrimental to entrepreneurship. 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. While it sounds incredible—no boss, no meetings, no deadlines—too much freedom can feel burdensome. When every option is available, deciding how to spend your time can become oddly heavy.
Every weekday after dropping my kids off at school, I have total discretion over my day. I can play tennis, write, nap, hike, or do absolutely nothing. Yet, when every day feels like a vacation, the novelty eventually wears off.
After over 13 years of freedom, I no longer wake up excited by the prospect of doing whatever I want. Autonomy has become my default setting, not a luxury. The paradox of early retirement is that the more freedom you have, the less you notice it.
To counteract this complacency, I’ve found it essential to maintain a sense of structure and challenge. That’s why I’ve kept a consistent writing schedule of 3–4 times per week since July 2009, even after leaving my job in 2012. Writing provides a sense of purpose and accountability that pure leisure cannot.
2) It’s Hard to Spend Money on Fun When You’re Already Happy
FIRE can make you hesitant to spend money on leisure. It feels like paying extra for tap water when 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, 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 use the kids’ school holidays for tennis and soccer lessons (free) and a pool day at my underutilized sports club (which costs $180/month). Daddy day camp to the max!
Additionally, I recently spent three weeks dealing with tenant turnover, which is always unpleasant. After all that effort, spending more than half of one month’s rent on a trip felt uncomfortable.
If you’re responsible for household finances, you can’t help but think about cost-benefit analysis. But it’s crucial to consider what the other family members want to do. Since I turned 45 in 2022, I’ve been trying my best to spend more money.
3) Your Vacation Property Likely Won’t Be as Nice as Your Home
Another post-FIRE downer: vacation properties usually aren’t as nice as your primary residence. This applies to most workers who vacation too.
You could spend a small fortune renting a luxury spot, but most FIRE practitioners won’t do that. After years of saving aggressively and avoiding excess, the idea of spending thousands to rent a house for a week feels counterintuitive.
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 have substantial active income, spending becomes easier.
If you’ve recently purchased a house you love, you’ll be more reluctant to leave it. I adore our home—the Toto Washlets, the view, the space inside and out. Every day feels like living in a luxurious vacation property. So paying money to downgrade feels off while our existing home sits empty during our absence.
Remember, the true cost of your vacation includes the cost of the trip plus the daily expenses of maintaining your existing home. Here’s my vacation spending guide to help you spend more responsibly while away. It’s easy to overspend 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, then 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 different backgrounds.
It’s hard to dislike someone once you’ve shared a meal 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 child, I lived in six countries, studied abroad during my junior year, and traveled throughout Asia and the U.S. for work, checking off bucket-list sites like Angkor Wat, the Taj Mahal, and the Colosseum.
Sure, I’d still love to visit Cairo and Petra, but they can wait until our kids are 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 akin to receiving paid parental leave—wonderful work benefits that shouldn’t be taken for granted.
So take all your vacation days. Don’t hoard them out of fear of losing your job or missing a promotion. The only exception is your final year before FIRE; bank those days since your employer must pay them out in cash when you leave.
The more you’re micromanaged and undermined at work, the more you’ll appreciate your vacations. Paid time off feels like sweet revenge for all the nonsense you endure. But once you’re no longer escaping anything, vacations lose that contrast.
You’ll Still Have Fun While Away
Even though vacations aren’t 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!
More importantly, our kids had the time of their lives. They told us, “It was the best time ever.” That kind of feedback is truly priceless.
As a FIRE parent, it’s wonderful never having to ask for time off when my kids are on break. That’s a privilege I didn’t fully appreciate until I realized how many working parents scramble for childcare during random school in-service days.
If you aspire to retire early but worry that kids will spoil your ideal post-work lifestyle, don’t fret! Kids today have so many days off from school—between local holidays, federal holidays, and in-service days—that you’ll have plenty of opportunities to travel. We’re talking 3.5 to 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 rekindle your excitement for vacations in retirement, consider taking on challenging projects. Juxtaposing the hard with the easy can enhance your appreciation for the good life.
For me, that’s been writing books. Writing articles has become less challenging, but each book takes about two years to complete. 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—a tough feat given that over 300,000 books are published each year.
This achievement motivated me to vacation in Honolulu for five weeks because I felt I deserved it. Of course, it wasn’t entirely relaxing; I was remodeling my parents’ in-law unit and confronting difficult childhood memories. But this time, the vacation felt more meaningful because it followed a period of hard, creative work.
Don’t assume early retirement will lead to a life filled with 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 balanced life!
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 live like you’re on a permanent vacation, you need to save and invest diligently while keeping a close eye on your finances. Freedom without financial clarity can easily lead to 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. This platform has helped me stay disciplined and organized long after leaving my day job.
If you have over $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 perspective 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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