Overwhelmed, Not Bored: An Unexpected Challenge Of Retirement

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!

However, after I left work, I must have told my wife I was bored every week for a year. All of my friends were still working since 90% of them were under 40. Essentially, I had to fill my Mondays through Fridays with something productive and wait until they could come out and play on the weekend.

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.

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 my kids were out of school on Thursday and Friday, and my wife and they wanted to go to Lake Tahoe.

If it were any other week, I’d enthusiastically go because Lake Tahoe is awesome. However, by going to Lake Tahoe with my family, I would 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 night 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 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 to spend time with since most people are still working. Thankfully, as you age, there will naturally be more retirees or 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 you know more people.

The thing is, there will always be plenty of people looking to play. You just become more OPEN to playing with more people as you age. Your universe tends to wider.

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 have a conversation.

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 content on Monday, Wednesday, and Friday mornings before taking the kids to school, which adds to the morning rush.

I’m gradually 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
• Dad’s night out
• Mom’s night out
• Volunteer events
• School fundraising events
• Poker nights
• Cooking nights
• Sports trips with your kids
• Political 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 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
• Writing more books

Don’t fear boredom or loneliness in retirement. You’ll find more than enough exciting activities to fill your days.

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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