On October 8, 2025, we determined to go on a household trip I used to be decidedly unexcited about. That whole week was presupposed to be my time to attend the Fairfield Challenger tennis event day-after-day with my buddy Richard. September and October are tennis paradise months within the Bay Space, with a number of tournaments and best climate. This 12 months 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 youngsters actually wished to go to San Diego to see Legoland and SeaWorld for the primary time.
I, alternatively, was completely comfortable to remain house, save ~$5,000, and luxuriate in watching skilled tennis, one in all 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 very best seats in the home – proper on the court docket!
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 mum or dad, I might not justify that type of indulgence.
My Nice Dislike Of Flying
I dislike flying because of the strains, the delays, the prices, seat hogs, and generally unruly passengers. After taking round 200 work flights over 13 years, I’ve skilled each type of journey distress possible. And if I’m being trustworthy, I nonetheless take into consideration dying 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 high of the North Tower earlier that 12 months.
If I’m going to fly, I’d somewhat or not it’s to go to my mother and father in Honolulu, to not stand in limitless 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 seem like they’re having the time of their lives! Life actually is healthier when you’ve got extra pursuits.
So right here I’m – the reluctant, barely grumpy dad – sharing my ideas earlier than takeoff on why it’s best to take as many holidays as you’ll be able to when you’re nonetheless working. Holidays will not be solely extra pleasurable when you’re nonetheless within the grind, however they’re additionally therapeutic, serving to you recharge and lengthen your profession longevity.
Over the long run, the extra holidays you are taking, the extra money you very effectively make!
Why Holidays Aren’t As Nice As soon as You Retire Early
In a earlier submit, I mentioned how being really FIRE is horrible for entrepreneurship. Now listed here are three explanation why holidays lose their magic after early retirement.
1) You Take Your Freedom for Granted
The “downside” with FIRE is having limitless 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 offered, deciding what to do together with your time can really feel oddly heavy.
Each weekday after dropping my children off at college, I’ve complete discretion over my day. I can play tennis, write, nap, go on a hike, or do completely nothing. There’s no one to inform me what to do or do it. But, when day-after-day can really feel like a trip, the novelty finally wears off.
After 13+ years of freedom, I don’t get up excited by the concept of with the ability to do no matter I need. Autonomy has turn into 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’ve got, the much less you discover it.
To counteract this complacency, I’ve discovered it’s important to keep up 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 goal 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 Onerous to Spend Cash on Enjoyable When You’re Already Pleased
FIRE could make you reluctant to spend cash on leisure. It’s like paying additional for faucet water, you have already got entry to what you want.
Since retiring from a standard day job in 2012, I’ve found loads of cheap actions that convey me pleasure: enjoying tennis, enjoying pickleball, writing, 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 lease 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 spite of everything that effort, to then spend greater than half of 1 month’s lease on a visit felt uncomfortable.
When you’re the particular person liable for your family funds, you’ll be able to’t assist take into consideration cost-benefit evaluation. However it’s necessary to consider the opposite members in your loved ones and what they wish to do. Since I turned 45 in 2022, I’ve being attempting my finest to spend extra money.
3) Your Trip Property Possible Received’t Be as Good as Your Residence
One other post-FIRE downer: the holiday property normally isn’t as good as your main residence. This pertains to most employees who trip too.
You could possibly spend a small fortune renting a luxurious spot, however you in all probability received’t as a result of that’s not how most FIRE practitioners assume. We spent years saving aggressively and avoiding extra. The thought of dropping 1000’s to lease a home for every week, not to mention a day, goes in opposition to that conditioning.
As an alternative, you’ll probably accept a modest Airbnb or resort room, cramming everybody in. Solely the really rich, the highest 0.1%, would lease a trip house as good as their very own. If you’ve bought a number of energetic revenue coming in, it is a lot simpler to spend.
When you’ve just lately purchased a home you like, you’ll even be extra reluctant to go away it. I really like our house – the Toto Washlets, the view, the area in and out. Every single day already seems like residing in an opulent trip property. So paying cash to downgrade feels off whereas our current house sits empty whereas we’re away.
Bear in mind, the true value of your trip is the price of your trip plus the day by day value of sustaining your current house. This is my trip spending information that can assist you spend extra responsibly whereas away. It is rather simple to go nuts whereas in trip mode.
When Holidays Are Higher Put up-Early Retirement
Holidays are most enjoyable post-FIRE should you’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 can be a greater place if extra folks traveled and shared meals with these from utterly completely different backgrounds.
It’s laborious to hate somebody when you’ve damaged bread with them.
Holidays are additionally higher should you retire nearer to the normal age of 60-65. After a lifetime of buying and selling time for cash, you’ll admire your freedom and the time you’ve got left greater than the early retiree.
Sadly, the joys of journey has pale for me as a result of I grew up residing overseas for 13 years. As a overseas service officer’s child, I lived in six international locations, studied overseas my junior 12 months, 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.
Certain, I might nonetheless love to go to Cairo and Petra, however they will wait till our youngsters become old.
The Greatest Holidays Are When You’re Nonetheless Working
When you’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 go away. What fantastic work advantages that shouldn’t be taken with no consideration.
So take all of your trip days. Don’t hoard them out of worry you’ll lose your job or miss a promotion. The one exception is your last 12 months earlier than FIRE. Financial institution these days since your employer has to pay them out in money while you go away.
The extra you’re micromanaged and undermined at work, the extra you’ll take pleasure in your holidays. Paid day off seems like candy revenge for all of the nonsense you place up with. However as soon as no one’s telling you what to do, holidays lose that distinction. You’re not escaping something anymore.
You’ll Nonetheless Have Enjoyable Whereas Away
Although holidays aren’t fairly as thrilling after early retirement, I nonetheless admire the liberty to journey every time I need. I’m revisiting this submit after coming back from LegoLand and SeaWorld, and you already know what? I had a blast!
However extra importantly, our youngsters had the time of their lives. They informed their mother and me, “It was the perfect time ever.” That type of suggestions is actually priceless and motivating to go on extra holidays for them.
As a FIRE mum or dad, it’s additionally good by no means having to ask for day off when your children are on break. That’s a privilege I didn’t absolutely admire till I noticed 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 children will spoil your best post-work life-style, 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 12 months, which is greater than sufficient trip time.
Do Onerous 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 laborious with the simple to raised admire the nice life.
For me, that’s been writing books as a result of writing articles is not laborious. Every e book takes about two years to finish, and once I printed Millionaire Milestones: Easy Steps to Seven Figures in Might 2025, I felt an incredible 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 printed a 12 months.
That achievement made me extra motivated to trip in Honolulu for 5 weeks as a result of I felt like I deserved it. In fact, it wasn’t a very stress-free journey. I used to be transforming my mother and father’ in-law unit, confronting troublesome childhood recollections, and attempting to show my Hawaiian roots. However this time, the holiday felt extra significant as a result of it adopted a interval of laborious, inventive work.
Don’t assume early retirement will create a life filled with thrilling holidays. You may go travel-crazy at first, however finally the novelty fades, and also you’ll begin craving productiveness and goal once more. Take pleasure in a pleasant steadiness!
Reader Questions
Fellow retirees, have you ever discovered holidays to be much less thrilling now that day-after-day can really feel like one? Did you journey lower than you initially deliberate, or burn out after going too laborious 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 house?
And what do you assume – are holidays actually that enjoyable when you not want an escape from work?
If You Need To Go On Everlasting Trip
In case your purpose is to sooner or later reside such as you’re on a everlasting trip, it is advisable to save and make investments diligently whereas maintaining shut monitor of your funds. Freedom with out monetary readability can simply flip into hidden stress.
Since 2012, I’ve used Empower’s free wealth administration instruments to watch my internet price, handle money move, and cut back funding charges. The platform has helped me keep disciplined and arranged lengthy after leaving my day job.
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