Recently, I went off the deep end—living like a degenerate gambler and party animal—and I wanted to reflect on it. Perhaps to nobody’s surprise, I don’t think having extreme amounts of fun is good for your financial future. It’s probably also not good for your health.
In our personal finance world bubble, where we go to bed by 11:30 PM, wake up by 5:30 AM to grind for a couple hours on our X Factor before work or childcare, and always pay ourselves first before spending any money, it was eye-opening to realize that many people don’t live this way and actually party it up frequently, even with kids!
The Sacrifices We Make To Achieve Financial Independence
As a FIRE proponent since 2009, one of the common questions I get is what sacrifices I made to break free from the corporate grind at 34—and whether it was worth it. My answer: 60+-hour workweeks for 13 years, skipping out on most barhopping and clubbing, and enduring enough stress to develop chronic back pain and other physical ailments.
Was it worth it? Absolutely. Hard work and stress were all I knew after college. In high school, I was flipping burgers at McDonald’s and working temp jobs for minimum wage. So when I had the chance to get paid significantly more to suffer, I made the most of it until I burned out. Thankfully, the chronic pain also went away once I left work.
Now, after 13 years of semi-retirement, the sacrifices feel even more worthwhile. Looking back, I would have pushed myself even harder. The window of opportunity to earn and grow doesn’t stay open forever. You will get older. You will get tired. And luck won’t always be on your side.
The sacrifices you make today will be worth it in the future. Too bad many people don’t realize this fact until they’re too old.
Partying Like a 27-Year-Old Degenerate
But I must admit—I sometimes wonder what it would’ve been like to party it up in my entire 20s like some of my classmates and colleagues did. So, to scratch that itch, I decided to do just that on a recent weekend.
On Friday, January 31, 2025, I had lunch downtown with a friend who played in the NBA. He was speaking at my friend’s company so we all decided to get together since he flew in. After lunch, I rushed home to then drive to play tennis at an indoor club with several other buddies because it was raining. Then I went to pick up my kids from school.
After dinner and tucking the kiddos to bed, at 9 PM, I went to my softball buddy’s place for a game of Texas Hold’em. He’s 27 and had a group of late-20s friends and a mid-30s friend over, plus me, the senior citizen at 47.
We played poker, drank Red Bulls and vodkas, ate homemade chocolate chip cookies, talked story, and had a blast until 2:45 AM! It was a good group of guys from various financial backgrounds.
Here’s one of our hands with three players going all-in with Ace (H)/Jack (C), Pocket 2s, and Ace King Suited. The guy with pocket deuces first went all in, then the guy with Ace Jack pushed all in for even more, and finally, the guy with Ace King suited called.
Went To A Concert The Very Next Night
I crawled into bed at 3:30 AM and, inexplicably, woke up at 7 AM. Wrecked. But the day didn’t stop. I took my daughter to ballet, went paint shopping with my son, painted the interior of our old house, then took the family to my son’s classmate’s birthday party.
At 4:40 PM, I left for a USTA tennis match at 5 PM, which I lost in a brutal three-set tiebreak. Then, without missing a beat, I rushed home at 7:30 PM to shower, get dressed, and go out again at 8:30 PM—this time to the Sultan + Shepard concert at The Warfield with my wife. The tickets cost $165 each and the Bacardi and Cokes were $18 each! YOLO baby!
We danced and vibed until 1 AM before going to bed at 2 AM. For the first time in over 10 years, I slept in until 9 AM, seven hours straight! It was glorious.
Not Very Productive the Next Day
Usually, I write my Sunday newsletter Friday night or sometime Saturday. But this time, I told myself I’d do it Sunday morning because I was feeling lazy. Problem was, I didn’t expect to wake up so late. I ended up publishing at 11:30 AM—seven hours later than usual. Oops!
If I had a boss, they’d be pissed. If I charged for my newsletter, subscribers might ask for refunds. Luckily, I answer to no one, and everything I write is free. Ah, the glory of doing your own thing and being your own boss!
Which got me thinking—how do people party hard and still get things done? I could never have been productive while gambling and partying until early in the morning in my 20s and 30s, let alone in my late 40s. My lack of productivity would have then hit my saving and investing. Ultimately, I would have had to have worked for many more years to achieve financial freedom all for the sake of more partying. That doesn’t seem worth it at all!
Given the rainy weather, my family and I spent the rest of Sunday grabbing lunch, doing more painting at our old house, and checking out open houses for research and interior design inspiration.
Now that I think of it, one reason I felt confident going all out that weekend was because I could rest and recover on Monday after I dropped my kids off at school. If you have kids in school, and you don’t have a day job, the time to party is during the weeknights!
Don’t Go Off the Deep End Before You Have Enough Money
Of course, you should have fun. You don’t want to sacrifice every ounce of enjoyment on your way to financial independence. Enjoy the journey!
But, like everything, moderation is key.
The people I know who partied hard in their 20s and 30s and spent freely are, unsurprisingly, far behind financially. Some have family money to fall back on, but most will need to work for decades. It is their choice.
If you want to party hard, quiet quit, work from home to play pickleball during the day, or take long gap years, it’s your prerogative. However, at least try to reach your Minimum Investment Threshold Amount (MIT) first. Once your investments can potentially generate more than your day job income ~70% of the time, you’ll have a much better safety net in case of layoffs or underperformance.
Competition is only getting fiercer due to globalization and artificial intelligence. The best balance may be to party in moderation until you reach MIT, party a little harder afterward, and go on a bender only once you have enough passive income to cover all your expenses. This is the smarter way.
You Won’t Dramatically Change Who You Are After You Achieve FIRE
Once you reach financial independence, you may realize that excessive partying was never as fun as it seemed. You might think you’ll finally have time for all the wild adventures you put off, but in reality, you’ll probably just continue living life much as before—just with a little more joy and ease.
Going on a bender once a quarter or even once a month can be a good time, but every week? That gets old fast. Seeing 20 countries in Europe over a three-month time period? That also starts getting old because once you’ve seen one gothic church, you’ve seen them all.
It’s funny how we often chase what we don’t have, only to take it for granted once it’s within reach. If you retire early in a big city, you might actually feel more overwhelmed than bored—there’s too much you could do, and that paradox of choice can be exhausting.
For me, one wild weekend every quarter is more than enough. These days, I’d much rather enjoy a great meal, watch an engaging show, or get lost in a good book at home.
Wow, I really do sound like an old fart now. So… where’s the next party at?!
Did you party hard in your 20s and 30s? If so, did it impact your work productivity and personal finances? Do you still party like a degenerate now? If so, how do you maintain the energy and joy to keep the good times rolling without burning out?
Pick Up A Copy Of Millionaire Milestones
If you want to be able to party like a degenerate without having to worry about your financial future, grab a copy of my new book, Millionaire Milestones: Simple Steps to Seven Figures. With over 30 years of experience working in, studying, and writing about finance, I’ve distilled everything I know into this practical guide to help you achieve financial success.
Millionaire Milestones is your roadmap to building the wealth you need to live the life you want. Order your copy today and take the first step toward the financial future you deserve!
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