Before retiring in 2012, I didn't fear boredom or loneliness. It never occurred to me that I would be bored with so much potential freedom. My main fear was whether giving up a steady paycheck was an impetuous move that could lead me to financial ruin!
After I left work, I found myself telling my wife I was bored almost every week for a year. Most of my friends were still working, as 90% of them were under 40. We agreed that my wife would continue working until she negotiated a severance package at age 35. In the meantime, I had to find productive ways to fill my weekdays and wait for the weekends when my friends were free.
When some friends told me they couldn't go out after work because they had to travel to a conference abroad, I was jealous. Ah, the days of traveling for free to drink and mingle with interesting people.
Now that I'm 47, I am almost never bored or lonely. Instead, I sometimes feel overwhelmed, which has required me to set boundaries to get back to a happy state. The paradox of choice says that the more activities and opportunities you have, the more stressful life can be!
Too Many Conflicting Interests to Be Bored and Lonely
Fall is my favorite time of year in San Francisco because it's hot, and there are a bunch of tennis tournaments I like to attend. Instead of flying five hours to New York City to watch the U.S. Open, I can just drive between 7 and 65 minutes to watch local tennis tournaments with my buddy, Richard.
Richard, 67, is a fellow retiree who left his IT job at age 52. During the pandemic, we would hunt all over the city for public courts to play on. We now watch all the tournaments together in the Bay Area like junkies. He is one of my best friends.
The Constant Need to Make Choices
There was a tennis tournament called the Kunal Patel SF Open in Golden Gate Park, which I wanted to watch. It's close to my house, and the tournament ran from Wednesday through Sunday. But school was closed on Thursday and Friday, and my wife and kids wanted to go to Lake Tahoe.
If it were any other week, I'd enthusiastically go because Lake Tahoe is awesome. However, going to Lake Tahoe with my family would mean I'd miss out on my favorite activity with my friends. Not only would we watch for a couple of hours, but we'd also then hop on an empty court and hit for a bit before watching another match. To me, this is a type of heaven.
Ultimately, my family and I made a compromise and left on Friday at noon, not on Thursday morning as planned, so I could watch more of the tournament. We had a nice time swimming, eating, and hiking up in the mountains, as usual.
However, not only did I miss out on some scintillating semi-final and final matches, but I also missed out on my regular 7 a.m. Sunday morning pickleball with 7–13 other enthusiasts. In addition, a softball buddy hosted poker night at his house Saturday evening too!
As a recovering stock market addict, playing poker with the guys is absolutely one of my favorite pastimes. At least in a home game, I won't risk losing life-changing sums of money while indulging in whiskey and pizza until 3 a.m.!
Why You Won't Be Bored and Lonely in Retirement
Whether you are an early retiree or a traditional retiree, you have reached an important milestone that took careful planning and discipline. You were intentional with your saving and investing habits. You also planned ahead to ensure that your finances would be alright after you said goodbye to work.
Given the amount of planning it takes to retire, you will also put in the work to find something you enjoy doing in retirement. You're not going to just sit there and be bored for years. Instead, any boredom you initially experience will eventually be resolved by you taking action to find something enjoyable to do.
You are a dynamic individual who will rationally take action to solve suboptimal situations.
Took Me A Year To Stop Feeling Bored
Going from 60+ hours a week to zero was jolting, like a high-speed car crash. I needed more time to adapt compared to someone who was working 40 hours a week or less before retiring.
But after a year, I found my rhythm in writing on Financial Samurai, playing tennis, working on real estate remodeling projects, playing poker, and traveling. I also found part-time consulting work at Empower for 15–20 hours a week to keep me engaged. That was cool because it combined experiencing the exciting startup life with financial technology in San Francisco.
Finally, to meet new people, I used to go to personal finance conferences before having kids. Going to a conference in New Orleans was particularly memorable. The architecture and beignets were amazing.
Personally, I've found it extremely difficult to stay retired after retiring early. As a result, I no longer say I'm retired to anybody who asks. Instead, I say I'm an author.
It Will Be Easier to Find Friends the Older You Get in Retirement
If you are a traditional retiree (60+), then there are plenty of people your age to hang out with. There are even planned communities for retirees with endless activities you can move into.
But if you retire early, it will take more work to find people your own age to spend time with since most of your peers are still working. Thankfully, as you age, there will naturally be more retirees and people with flexible work schedules due to their seniority.
Think about an umbrella getting bigger and bigger as you age. You simply have the ability to connect with more people, partly because your network keeps expanding over time.
The thing is, there will always be plenty of people looking to hang out. You just become more OPEN to spending time with more people as you age. Your universe tends to widen.
The 70-year-old is happy to hang out with people his age down to the 35-year-old early retiree if they want to hang. It's just that when you're 35, you may not be as interested in hanging out with the 70-year-old.
Combatting Ageism to Make More Friends In Retirement
To counteract ageism, you must develop a skill where the younger person would want to play with you or appreciate you. If you do, you'll never be bored.
Young people aren't maliciously discriminatory against older people, except potentially in the workplace. It's just that young people might not have much in common with much older people, which leads them not to interact.
One of the reasons why pickleball is the fastest-growing sport in the world is that people with wide age differences and skill levels can find enjoyment playing together. You'll easily see 65-year-old women with knee braces and bad backs beating inexperienced young bucks in their 20s on the court.
Just the other night, I played pickleball until 10 p.m. with a woman 20 years my junior. I had seen her around the public courts before, and she decided to join my club. Since we recognized each other, we formally introduced ourselves and ended up playing for an hour with multiple other people.
Now I've got a friend I can drill with from 8:30 p.m. to 10 p.m. after my kiddos go to bed. We'll introduce each other's friends of the same skill level, and that's how a big WhatsApp chat group forms to increase our chances of always having a hitting partner.
Stay Current with What Younger People Care About
As we get older, we get set in our ways. And when we become more inflexible in thought, our social world gets smaller. Constantly learning different perspectives is one of the reasons I love publishing on Financial Samurai.
Not only should older retirees develop a skill to be able to hang with younger people, but they should also develop an understanding of the interests of younger people. This understanding includes music, current events, popular TV shows, social issues, pain points, and more. This way, it's easier to converse.
If you're a Boomer who is stuck thinking about how it was so easy to buy a house and raise a family back in your day, you will probably turn off people in the Gen Z generation. Remember, your goal is to make positive connections. Positive relationships are the key to a happy retirement and overall happy life.
If You Retire With Grade School Kids
You won't fully appreciate the freedom you once had until you become a parent. If you retire early with grade school-aged kids, your downtime can quickly be consumed by family activities. Kids have boundless energy and will happily take up as much time and attention as you can give them. If you ever find yourself feeling bored in retirement and are open to it, having children could be the perfect remedy to add more meaning and purpose to your life.
In my first year of retirement, my internal mantra shifted from “Gosh, I'm bored today” to “Gosh, I'm so tired.” Thankfully, once your kids start attending school full-time, you'll regain a significant amount of your time. However, you'll likely fill it with other responsibilities and projects, potentially leading to a sense of being overwhelmed again.
For example, I'm in charge of the daily school drop-off and pick-up, which can be stressful due to morning traffic and the pressure to avoid tardiness—one of my biggest pet peeves. On top of that, I aim to publish new articles on Monday, Wednesday, and Friday mornings before taking the kids to school, which adds to the morning rush.
I'm learning to ease up on my self-imposed schedule to reduce stress and find a better balance. If you haven't noticed, it's more common for my posts to come out late mornings.
School Social Functions Will Keep You Busy
One of the biggest boosts in social activity for my wife and me came when our son started attending school full-time. Having school-aged kids is like a retiree rejoining the workforce. There are endless opportunities to meet other parents and participate in social activities.
Here are some examples of social events that come up regularly:
- Camping trips
- Birthday parties
- Dads' night out
- Moms' night out
- Volunteer events
- Sports practices
- School fundraising events
- Poker nights
- Cooking classes
- Sports tournament trips with your kids
- Special interest fundraisers
We attend about 90% of the events we're invited to, which likely contributes to the feeling of being overwhelmed. We find it impolite to decline an invitation if we’re able to make it. The only ones I typically skip are those that involve overnight stays. I’ll reconsider once both kids are over 10, but not before.
You Don't Need Work Colleagues to Stay Socially Active
It's natural to worry about feeling bored and aimless after retiring. When you’ve spent years with the same work colleagues, their absence may feel unusual at first. But trust me, retirement opens doors to new friendships and interests.
It might take a few months or even a year or two to find your rhythm, but you eventually will. And leaving work doesn’t mean losing the friendships you've built there. You’re simply free to explore new worlds with your newfound time!
Some of my current interests include:
- Improving my Mandarin Chinese
- Improving my pickleball skills
- Gardening and growing thick hedges to create a cozier home
- Teaching personal finance at the grade school level, partially because I miss my kids during the day
- Coaching my kids in whatever activities they want to pursue
- Cultivating a hard-to-read presence at the poker table
- Building more passive income to regain financial independence by Dec 31, 2027
- Writing more books to help more people with their personal finances while setting a good academic example
Don't fear boredom or loneliness in retirement. You’ll find more than enough exciting activities to fill your days. In fact, one of my goals for 2025 is to stop doing so much! I plan on protecting my nap time window of 1:30pm – 3 pm so I can recharge before picking up my kids.
Readers, any retirees out there who are bored? Or did you find people with common interests and are now sometimes overwhelmed with choices? Besides financial worry and boredom, what else do you worry about after retiring?
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I’ve always been curious about the popularity of senior resorts in Florida. The combination of resort-style living with community activities is genius. It’s great to see how these places promote an active and connected lifestyle for retirees
One of life’s great mystery’s that I should have an answer to, but I simply do not, is how I ever had the time to work a job. Being retired for 6 years now, I simply cannot figure out how I ever had the time to work.
I wish I could spend every afternoon with my kids. They’re both away at university and it takes every ounce of self-control I have not to buy a van, build it out, and park it in front of alternating apartment/dorm buildings so I can see them every day. Work is irrelevant compared to the joys of being a parent. Been retired a year and I’m not bored at all but being away from my kids is not easy. Enjoy them when they’re young! Even if it’s hard!
I hear you! I cut my Pickleball short 30 minutes this morning and left at 8:30 AM to take my kids to parkour class and hang out with them for the rest of the day. The weekends are now so precious now that they are in school full-time.
But I definitely plan to invest in a piece of property right next door to their dorm in college! Haha
I loved living in Williamsburg, Virginia, the College town of the College of William and Mary. So many fun parties and show shows and activities.
I’m curious how many activities your kids are in. I’m not retired and I don’t know how working parents juggle this. My kids’ friends are in swimming, soccer, robotics, karate, etc, etc. It fills up the entire weekend. When my kids were younger we did many family activities, visited grandparents/family, had playdates, but now it seems everyone is doing these activities on the weekends and we’ve kind of been sucked in. This is on top of afterschool activities (mostly because we need childcare until 6:00). My son recently joined a league where games can start at 5:00 weekdays. How do parents get their kids there?? (The ones who work from home maybe…) Also with aging parents…they seem to be even needier. Life in the sandwich generation!
I don’t think it is possible and people just do that by squeezing their time and energy because of the current society (There is a great book about that “the myth of normal” by Gabor Mate). Kids get tired after school and they and the parents need downtime (unscheduled activities). Lucky working parents have work flexibility, and their kids are cooperative, and they are super high energy themselves (may have a cost later, who knows), or have some extra help etc. Kids and your body/health don’t typically follow the social/work agenda, and that is why it is so nice to retire early (at least one parent) to free up the time to nurture the family relationships with kids (not necessarily fill them up with “activities”).
I love Gabor Mate’s talks!
Not many. They are only 4.5 and 7.5. As a stay-at-home parent since 2017, I’ve been working with them on the fundamentals, and still am. This includes running, walking, biking, swimming, and now parkour/body movement activities for balance.
We do have soccer practice for my 4.5-year-old at 4:30 pm today, which is just a fun kickaround and social event. I’ll practice dribbling and kicking with her and my son in our yard. I’m not sure why I’m not stressed or having our kids do more. Perhaps because they are still so young, what’s the rush? It’s not like they are going to turn pro athletes.
A nice book is: Take Back the Game: How Money and Mania Are Ruining Kids’ Sports–and Why It Matters, by Linda Flanagan.
How old are your children and why do you think you and other parents are getting them to do so many activities? If the kids enjoy them though, that’s wonderful.
BTW, what happened to your site? I remember last time we interacted on Twitter, you were quite angry at something I said, perhaps how expensive it is to raise a family in a big city. Was that right? If so, have you come around to this?
My kids are 8 and 11. Unlike other parents we don’t have our kids in as much activities but sometimes I wonder if I’m “depriving” them of something. My older one asked to join some sports teams and said asked why he didn’t do this earlier. So I felt a little guilty. It’s a tough balancing act! My younger isn’t as interested right now.
As for my site, it’s collecting cobwebs. I was going to let the domain expire but figured I’d keep it up thinking I might reboot it or just to keep as a journal of the past. I don’t remember interacting with you and being angry with something you said. I did probably disagree that you need $350k to enjoy a middle class life in a high cost area though. I don’t always agree with your opinions but I do enjoy reading your perspective on things.
The good thing is that at eight and 11, you still have plenty of time to do more activities and make up for anything they felt they are missing.
Is it not possible for one of you to pick up your kids before 6 PM to go to activities? That’s a pretty long day. I remember getting out of school around 2:45 PM or 3 PM, and then having tennis practice from like 3:15 PM until 4:45 PM. I was dying by then. It affected my second period the next day where I would constantly just fall asleep.
Another good book on this topic is Little Platoons by Matt Feeney. The main thrust of the book is that a lot of families put their kids in back-to-back scheduled activities not necessarily because they enjoy them, but to get a leg up in college admissions, and it basically amounts to letting the college admissions industry intrude upon our families’ free time and sanity at earlier and earlier ages. Eye opening book, although my wife and I have already resoundingly opted out of it, and if the Harvard admissions officers look down their nose at our son when he says “yeah, I just kicked a ball around with my friends at the park after school” instead of starting a charity or something, then so be it, he can be an electrician and make $200K+ per year with $0 student debt.
Good plan! I don’t expect my kids to get in anywhere or get financial aid. So I’m not that thrilled about college. I’m planning on teaching them practical skills before 18.
Boy, I look forward to playing pickleball all day when I retire. What advice would you give for semi-beginners who want to improve (3.0 ish level)? Thank you.
Just keep practicing! Specifically the dinks and drops from the baseline. 70% of your shots should be short placement shots where you patiently wait for a pop up to attack. Power is overrated in Pickleball given the cord is so small.
It’s nice to hear about your hobbies and friends!
Thanks for the post!
My wife and I retired eight years in our late 40’s and are never bored. We travel almost full time which can make friendships challenging but we have met some great people we keep in touch with and meet up with along the way.
Best advice for older people wanting to make friends with younger folks is also take an interest in what they are doing. Too many older retirees we meet just want to talk about themselves.
Although I’m not totally retired, the kids have vaccumed up my free time. School drop offs and pick ups, daughter is playing hockey 3x a week and also soccer, and middle son is learning Cantonese and playing soccer. Youngest is not 2 yet, but he’s absorbing all of the content while along for the ride. I’m so busy these days that I’m grateful work is casual. Also, I unexpectedly have made some really great friends through my kid’s sports and it’s so nice to come together and support the kids.
I used to worry about boredom, but now I worry about having enough capacity. I always try to regain perspective by remembering how it is for both parents working full time and raising children. Not easy.
It’s so true that we all find ways to fill up our free time whether it be resting, surfing the web, doing errands or chores, picking up a new hobby, volunteering, reading, shopping, etc.
I also agree with what you said about keeping up to date with current events, demographic shifts, social pressures, and what’s trending. It makes it much easier to talk to other people and build connections.
Your comment on feeling overwhelmed reminded me of a graphic I saw recently comparing parents today vs parents 30-40 years ago. In the past parenting seems like it was so much simpler: make sure your kids attend school and let them roam freely the rest of the time. Versus today parents are going crazy with so much pressure: get your kid into the best school with a huge wait list, be on 3 different sports teams simultaneously, take music lessons 1x week, hire a private tutor for math/english/SATs, shield them from environmental toxins and plastics, protect them from online predators, etc. etc. etc.
Mindfulness is more important than ever!