On October 8, 2025, we determined to go on a family vacation I used to be decidedly unexcited about. That complete week was purported to be my time to attend the Fairfield Challenger tennis match day by day with my buddy Richard. September and October are tennis paradise months within the Bay Space, with a number of tournaments and supreme climate. This yr was particularly thrilling with the Laver Cup on the town.
Nonetheless, October 9 and 10 occurred to be college holidays for my children, adopted by Columbus Day on October 13. My spouse and kids actually needed to go to San Diego to see Legoland and SeaWorld for the primary time.
I, then again, was completely glad to remain dwelling, save ~$5,000, and luxuriate in watching skilled tennis, certainly one of my absolute favourite actions, for $45 or much less per ticket. However as frugal tennis fanatics, we really volunteer as ball boys to get in free and get free lunch. Nonetheless, the most important pleasure is having the best possible seats in the home – proper on the courtroom!
Earlier than having children, I used to fly to New York Metropolis to go to my sister and watch the US Open in Flushing. I might go from 10 a.m. to 10 p.m. with out lacking a beat. However after changing into a father or mother, I might now not justify that form of indulgence.
My Nice Dislike Of Flying
I dislike flying as a result of strains, the delays, the prices, and typically unruly passengers. After taking round 200 work flights over 13 years, I’ve skilled each form of journey distress possible. And if I’m being sincere, I nonetheless take into consideration demise each time I board. The trauma from 9/11 by no means absolutely fades. I lived only a couple blocks away and had attended a convention on the prime of the North Tower earlier that yr.
If I’m going to fly, I’d somewhat it’s to visit my parents in Honolulu, to not stand in infinite amusement park strains. However I additionally know these journeys aren’t actually for me, they’re for the youngsters. So off we went, me internally reluctant however outwardly enthusiastic.
Oh, how I envy these mother and father who genuinely love Legos, curler coasters, and Disney characters. They appear like they’re having the time of their lives! Life actually is healthier when you might have extra pursuits.
So right here I’m – the reluctant, barely grumpy dad – sharing my ideas earlier than takeoff on why you need to take as many holidays as you possibly can when you’re nonetheless working.
Why Holidays Aren’t As Nice As soon as You Retire Early
In a earlier put up, I mentioned how being truly FIRE is terrible for entrepreneurship. Now listed below are three the reason why holidays lose their magic after early retirement.
1) You Take Your Freedom for Granted
The “drawback” with FIRE is having infinite freedom and selections. On paper, that sounds unbelievable with no boss, no conferences, no deadlines. However in actuality, an excessive amount of freedom can begin to really feel like a burden. When each possibility is on the market, deciding what to do together with your time can really feel oddly heavy.
Each weekday after dropping my children off at college, I’ve whole discretion over my day. I can play tennis, write, nap, go on a hike, or do completely nothing. There’s no person to inform me what to do or how you can do it. But, when day by day can really feel like a trip, the novelty ultimately wears off.
After 13+ years of freedom, I don’t get up excited by the thought of having the ability to do no matter I would like. Autonomy has grow to be my default setting, not a luxurious. What as soon as felt liberating now merely is. That’s the paradox of early retirement: the extra freedom you might have, the much less you discover it.
To counteract this complacency, I’ve discovered it’s important to take care of a way of construction and problem. That’s one motive why I’ve saved up a constant 3–4X per week writing schedule since July 2009, even after leaving my job in 2012. Writing offers me a way of objective and accountability that pure leisure can’t present.
With out some type of productive wrestle, the times can blur collectively, and even paradise begins to lose its shine.
2) It’s Laborious to Spend Cash on Enjoyable When You’re Already Completely happy
FIRE could make you reluctant to spend cash on leisure. It’s like paying further for faucet water, you have already got entry to what you want.
After greater than 13 years of monetary freedom, I’ve found loads of cheap actions that convey me pleasure: enjoying tennis, enjoying pickleball, writing, mountain climbing, and watching tennis.
So spending ~$5,000 on a visit I’m not enthusiastic about doesn’t really feel nice. I’d somewhat have used the youngsters’ college holidays for giving them tennis and soccer classes (free), adopted by a pool day with a giant swirly slide (using my underutilized sports activities membership membership that prices $180/month). Daddy day camp to the max!
As well as, I had just lately spent three weeks coping with tenant turnover, which is at all times disagreeable. I needed to record the property for hire once more, clear up what I might for showings, consider potential tenants, draft a brand new lease, assist with onboarding, and coordinate with the departing tenants on their move-out and cleanup. In any case that effort, to then spend greater than half of 1 month’s hire on a visit felt uncomfortable.
For those who’re the particular person chargeable for your family funds, you possibly can’t assist take into consideration cost-benefit evaluation. However it’s necessary to consider the opposite members in your loved ones and what they need to do. Since I turned 45 in 2022, I’ve being attempting my greatest to spend extra money.
3) Your Trip Property Seemingly Gained’t Be as Good as Your House
One other post-FIRE downer: the holiday property normally isn’t as good as your major residence. This pertains to most staff who trip too.
You possibly can spend a small fortune renting a luxury spot, however you in all probability received’t as a result of that’s not how most FIRE practitioners suppose. We spent years saving aggressively and avoiding extra. The thought of dropping 1000’s to hire a home for per week, not to mention a day, goes in opposition to that conditioning.
As an alternative, you’ll possible accept a modest Airbnb or resort room, cramming everybody in. Solely the really rich, the top 0.1%, would hire a trip dwelling as good as their very own. Whenever you’ve bought a number of energetic earnings coming in, it is a lot simpler to spend.
For those who’ve just lately bought a house you love, you’ll even be extra reluctant to go away it. I really like our dwelling – the Toto Washlets, the view, the house in and out. Every single day already seems like dwelling in an expensive trip property. So paying cash to downgrade feels off whereas our present dwelling sits empty whereas we’re away.
Keep in mind, the true value of your trip is the price of your trip plus the each day value of sustaining your present dwelling. Here is my vacation spending guide that can assist you spend extra responsibly whereas away. It is vitally simple to go nuts whereas in trip mode.
When Holidays Are Higher Submit-Early Retirement
Holidays are most fun post-FIRE for those who’ve by no means traveled earlier than. In case your mother and father by no means took you wherever, your job by no means despatched you on journeys, and also you by no means studied overseas, by all means journey! You’ll lastly have the liberty and means to discover.
Hopefully, you’ll go to a number of continents, immerse your self in new cultures, and notice how lucky we’re within the U.S. The world could be a greater place if extra individuals traveled and shared meals with these from utterly completely different backgrounds.
It’s arduous to hate somebody when you’ve damaged bread with them.
Sadly, the joys of journey has pale for me as a result of I grew up dwelling overseas for 13 years. As a international service officer’s child, I lived in six international locations, studied overseas my junior yr, traveled all through Asia and the U.S. for work for 13 years, and checked off bucket-list websites like Angkor Wat, the Taj Mahal, the Blue Mosque, the Colosseum, and the Winter Palace.
Positive, I would nonetheless love to go to Cairo and Petra, however they will wait till our children become old.
The Finest Holidays Are When You’re Nonetheless Working
For those who’re nonetheless working towards monetary independence, benefit from the unbelievable privilege of getting paid whereas on trip. It’s the identical pleasure as receiving paid parental depart. What fantastic work advantages that shouldn’t be taken as a right.
So take all of your trip days. Don’t hoard them out of concern you’ll lose your job or miss a promotion. The one exception is your ultimate yr earlier than FIRE. Financial institution these days since your employer has to pay them out in money whenever you depart.
The extra you’re micromanaged and undermined at work, the extra you’ll take pleasure in your holidays. Paid break day seems like candy revenge for all of the nonsense you place up with. However as soon as no person’s telling you what to do, holidays lose that distinction. You’re not escaping something anymore.
You’ll Nonetheless Have Enjoyable Whereas Away
Though holidays aren’t fairly as thrilling after early retirement, I nonetheless respect the liberty to journey every time I would like. I’m revisiting this put up after coming back from LegoLand and SeaWorld, and you already know what? I had a blast!
However extra importantly, our children had the time of their lives. They instructed their mother and me, “It was the very best time ever.” That form of suggestions is actually priceless.
As a FIRE parent, it’s good by no means having to ask for break day when your children are on break. That’s a privilege I didn’t absolutely respect till I spotted what number of working mother and father scramble to search out childcare throughout random college in-service days.
If you wish to retire early, however are afraid kids will spoil your ideal post-work lifestyle, don’t be concerned! Children these days have so many days off from college, between native holidays, federal holidays, and in-service days, that you will have loads of days off to journey. We’re speaking 3.5 – 4.5 months off a yr, which is greater than sufficient trip time.
Do Laborious Issues in Retirement To Higher Recognize Holidays
If you wish to get enthusiastic about holidays once more in retirement, do one thing difficult in retirement. It is useful to juxtapose the arduous with the simple to higher respect the nice life.
For me, that’s been writing books as a result of writing articles is now not arduous. Every e book takes about two years to finish, and once I revealed Millionaire Milestones: Simple Steps to Seven Figures in Might 2025, I felt an amazing sense of reduction and accomplishment. It even made the USA TODAY nationwide bestseller record. Not simple when there are solely 100 spots throughout all genres whereas greater than 300,000 books are historically revealed a yr.
That achievement made me extra motivated to trip in Honolulu for 5 weeks as a result of I felt like I deserved it. After all, it wasn’t a very enjoyable journey. I used to be remodeling my parents’ in-law unit, confronting troublesome childhood memories, and attempting to prove my Hawaiian roots. However this time, the holiday felt extra significant as a result of it adopted a interval of arduous, artistic work.
Don’t assume early retirement will create a life stuffed with thrilling holidays. You would possibly go travel-crazy at first, however ultimately the novelty fades, and also you’ll begin craving productiveness and objective once more. Get pleasure from a pleasant steadiness!
Reader Questions
Fellow retirees, have you ever discovered holidays to be much less thrilling now that day by day can really feel like one? Did you journey lower than you initially deliberate, or burn out after going too arduous early on? Do you wrestle to spend cash on new adventures when you’ve discovered loads of cheap methods to take pleasure in life at dwelling?
And what do you suppose – are holidays actually that enjoyable when you now not want an escape from work?
If You Need To Have A Everlasting Trip
In case your purpose is to sooner or later dwell such as you’re on a everlasting trip, it’s essential to save and make investments diligently whereas maintaining shut observe of your funds. Freedom with out monetary readability can simply flip into hidden stress.
Since 2012, I’ve used Empower’s free wealth management tools to observe my web value, handle money stream, and scale back funding charges. The platform has helped me keep disciplined and arranged lengthy after leaving my day job.
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