<\/p>\n
On October 8, 2025, our family embarked on a family vacation<\/a> 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.<\/p>\n 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.<\/p>\n Meanwhile, I was content to stay home, save around $5,000, and enjoy watching professional tennis\u2014one of my favorite pastimes\u2014for $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\u2014right on the court!<\/p>\n 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.<\/p>\n 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\u2019ve faced every travel misery imaginable. If I\u2019m 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.<\/p>\n If I must fly, I\u2019d prefer it be to visit my parents in Honolulu<\/a>, not to stand in endless amusement park lines. Yet, I understand these trips aren\u2019t really for me; they\u2019re for the kids. So off we went, with me feeling reluctant but trying to appear enthusiastic.<\/p>\n 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.<\/p>\n So here I am\u2014the reluctant, slightly grumpy dad\u2014sharing my thoughts before takeoff on why you should take as many vacations as you can while you\u2019re still working.<\/em><\/p>\n In a previous post, I discussed how being truly FIRE is detrimental to entrepreneurship<\/a>. Here are three reasons why vacations lose their magic after early retirement.<\/p>\n The \u201cproblem\u201d with FIRE<\/a> is having endless freedom and choices. While it sounds incredible\u2014no boss, no meetings, no deadlines\u2014too much freedom can feel burdensome. When every option is available, deciding how to spend your time can become oddly heavy.<\/p>\n 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<\/em>.<\/p>\n 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.<\/p>\n To counteract this complacency, I\u2019ve found it essential to maintain a sense of structure and challenge. That\u2019s why I\u2019ve kept a consistent writing schedule of 3\u20134 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.<\/p>\n 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.<\/p>\n After more than 13 years of financial freedom, I\u2019ve discovered plenty of inexpensive activities that bring me joy: playing tennis, pickleball, writing, hiking, and watching tennis.<\/p>\n So spending ~$5,000 on a trip I\u2019m not excited about doesn\u2019t feel great. I\u2019d rather use the kids\u2019 school holidays for tennis and soccer lessons (free) and a pool day at my underutilized sports club (which costs $180\/month). Daddy day camp<\/a> to the max!<\/p>\n Additionally, I recently spent three weeks dealing with tenant turnover<\/a>, which is always unpleasant. After all that effort, spending more than half of one month’s rent on a trip felt uncomfortable.<\/p>\n If you\u2019re responsible for household finances, you can\u2019t help but think about cost-benefit analysis. But it\u2019s crucial to consider what the other family members want to do. Since I turned 45 in 2022, I\u2019ve been trying my best to spend more money.<\/p>\n Another post-FIRE downer: vacation properties usually aren\u2019t as nice as your primary residence. This applies to most workers who vacation too.<\/p>\n You could spend a small fortune renting a luxury spot<\/a>, but most FIRE practitioners won\u2019t do that. After years of saving aggressively and avoiding excess, the idea of spending thousands to rent a house for a week feels counterintuitive.<\/p>\n Instead, you\u2019ll likely settle for a modest Airbnb or hotel room, cramming everyone in. Only the truly wealthy, the top 0.1%<\/a>, would rent a vacation home as nice as their own. When you have substantial active income, spending becomes easier.<\/p>\n If you\u2019ve recently purchased a house you love<\/a>, you\u2019ll be more reluctant to leave it. I adore our home\u2014the 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.<\/p>\n Remember, the true cost of your vacation includes the cost of the trip plus the daily expenses of maintaining your existing home. Here\u2019s my vacation spending guide<\/a> to help you spend more responsibly while away. It\u2019s easy to overspend in vacation mode.<\/p>\n Vacations are most exciting post-FIRE if you\u2019ve never traveled before<\/em><\/strong>. If your parents never took you anywhere, your job never sent you on trips, and you never studied abroad, then travel! You\u2019ll finally have the freedom and means to explore.<\/p>\n Hopefully, you\u2019ll 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.<\/p>\n It\u2019s hard to dislike someone once you\u2019ve shared a meal with them.<\/p>\n Sadly, the thrill of travel has faded for me because I grew up living abroad for 13 years. As a foreign service officer\u2019s 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.<\/p>\n Sure, I\u2019d still love to visit Cairo and Petra, but they can wait until our kids are older.<\/p>\n If you\u2019re still working toward financial independence, enjoy the incredible privilege of getting paid while on vacation. It\u2019s akin to receiving paid parental leave\u2014wonderful work benefits that shouldn\u2019t be taken for granted.<\/p>\n So take all your vacation days. Don\u2019t 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.<\/p>\n The more you\u2019re micromanaged and undermined at work<\/a>, the more you\u2019ll appreciate your vacations. Paid time off feels like sweet revenge for all the nonsense you endure. But once you\u2019re no longer escaping anything, vacations lose that contrast.<\/p>\n Even though vacations aren\u2019t as thrilling after early retirement, I still appreciate the freedom to travel whenever I want. I\u2019m revisiting this post after returning from LegoLand and SeaWorld, and you know what? I had a blast!<\/p>\n More importantly, our kids had the time of their lives. They told us, \u201cIt was the best time ever.\u201d<\/em> That kind of feedback is truly priceless.<\/p>\n As a FIRE parent<\/a>, it\u2019s wonderful never having to ask for time off when my kids are on break. That\u2019s a privilege I didn\u2019t fully appreciate until I realized how many working parents scramble for childcare during random school in-service days.<\/p>\n If you aspire to retire early but worry that kids will spoil your ideal post-work lifestyle<\/a>, don\u2019t fret! Kids today have so many days off from school\u2014between local holidays, federal holidays, and in-service days\u2014that you\u2019ll have plenty of opportunities to travel. We\u2019re talking 3.5 to 4.5 months off a year, which is more than enough vacation time.<\/p>\n 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.<\/p>\n For me, that\u2019s 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<\/a><\/strong><\/em> in May 2025, I felt a tremendous sense of relief and accomplishment. It even made the USA TODAY<\/strong> national bestseller list\u2014a tough feat given that over 300,000 books are published each year.<\/p>\n This achievement motivated me to vacation in Honolulu for five weeks because I felt I deserved<\/em> it. Of course, it wasn\u2019t entirely relaxing; I was remodeling my parents\u2019 in-law unit<\/a> and confronting difficult childhood memories<\/a>. But this time, the vacation felt more meaningful because it followed a period of hard, creative work.<\/p>\n Don\u2019t 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\u2019ll start craving productivity and purpose again. Enjoy a balanced life!<\/p>\n 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\u2019ve found plenty of inexpensive ways to enjoy life at home?<\/em><\/p>\n And what do you think\u2014are vacations really that fun once you no longer need an escape from work?<\/em><\/p>\n If your goal is to live like you\u2019re 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.<\/p>\n Since 2012, I\u2019ve used Empower\u2019s free wealth management tools<\/a><\/strong> 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.<\/p>\n If you have over $100,000 in investable assets\u2014whether in savings, taxable accounts, 401(k)s, or IRAs\u2014you can get a free financial check-up<\/strong> from an Empower financial advisor by signing up here<\/a><\/strong>. It\u2019s a simple, no-obligation way to have an experienced professional review your finances and provide objective feedback.<\/p>\n 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\u2019ve worked so hard to earn.<\/p>\nMy Great Dislike Of Flying<\/strong><\/h2>\n
Why Vacations Aren\u2019t As Great Once You Retire Early<\/h2>\n
1) You Take Your Freedom for Granted<\/h3>\n
2) It\u2019s Hard to Spend Money on Fun When You\u2019re Already Happy<\/h3>\n
3) Your Vacation Property Likely Won\u2019t Be as Nice as Your Home<\/h3>\n
When Vacations Are<\/em> Better Post-Early Retirement<\/h2>\n
The Best Vacations Are When You\u2019re Still Working<\/h2>\n
You\u2019ll Still Have Fun While Away<\/h2>\n
Do Hard Things in Retirement To Better Appreciate Vacations<\/h2>\n
Reader Questions<\/h2>\n
If You Want To Have A Permanent Vacation<\/h2>\n