Vacations are great for recharging—especially the long, 10-day-plus ones. I’m writing about this because of what I’ve seen with my parents and in-laws. If you’re planning to retire someday, you shouldn’t ignore this topic.
My in-laws seem to have retired well. About ten years ago, a few years before turning 60, they left the cold Midwest for a warm desert community designed for people 55 and older. They stay busy: golf, bridge, the fitness center, games, some travel, and part-time work keep them active. But my father-in-law, who’s been coaching part-time for the local schools, is getting tired of the underfunded program and unmotivated kids. If he quits, boredom is likely next.
Traditional retirement can be a boredom trap. You work hard for decades, juggle jobs, paychecks, and bills, and then reach a point where you want freedom. When that happens, many people hit the finish line and hear only crickets. After years of letting a job define you, losing that identity can be a shock. Friends are still working or have moved away to retirement hotspots. Sitting all day watching TV and eating poorly raises real health risks, too. Retirement works best when it includes activities, learning, hobbies, and new relationships.
Here’s my take: children get bored easily because they have few obligations, and handling that boredom helps them learn to be creative. I had lots of alone time growing up in the 70s and 80s—fewer scheduled activities meant more space to imagine. If I wasn’t watching a cartoon, I was exploring the backyard, riding bikes with friends, or building Lego only to knock it down in a fight with my Kenner Tie Fighter.
My low point came in college when I stayed in my dorm over the summer to help with maintenance. It was one of the worst decisions I’d made up to that time. With everyone gone, the empty dorm felt incredibly lonely. I didn’t sleep well, and I even made a new friend—a mouse who wanted my Wonder Bread. That “summer from hell” taught me that boredom mixed with loneliness can lead to depression. I still wonder how close I came to hitting that wall.
Boredom usually fades with steady work, relationships, and living with a partner. Having someone around—even if you’re just watching a movie with takeout—makes a big difference. Then you have kids and suddenly there’s no time for boredom. Work might be the only dull spot, and blogs or hobbies can fill it. But eventually kids grow up, leave for college or work, and you become an empty-nester. If your daily routine was tied to obligations, their absence can feel like a sudden loss.
Retirement often brings you full circle to childhood: you have freedom but you lack the structure that filled your days for decades. No wonder it’s easy to fall into the “boredom booby trap.” I suspect kids who were overscheduled might struggle more in retirement than those who had more free play. Many retirees report missing daily social interactions and feeling plain bored. The point is this: you need a new routine to replace the old one. It doesn’t mean you must find a paid job, but you do need structure. Without it, people get bored, act out, or even become depressed.
Here are some practical ideas:
1) Travel and volunteer. Combine seeing new places with meaningful work. Programs like the Peace Corps, Volunteer Forever, Global Volunteers, and Go Overseas are worth exploring. If you’d rather stay local, volunteer in ways that fit your interests. Don’t volunteer just to suffer—find roles that are mutually rewarding.
2) Garden. Growing vegetables or flowers is therapeutic. My grandparents loved their summer gardens, and I think that time in the dirt helped them live longer, healthier lives.
3) Take classes. Go to college, finish a degree, or audit classes just to learn and meet people. Living near a campus can give you access to lectures, sports, films, and other events.
4) Help with grandchildren. Many long-lived communities have grandparents who stay involved with the next generation. Pitch in part-time—looking after kids can be tiring, but also deeply rewarding.
5) Start a side hustle. There’s nothing wrong with working in retirement if it adds structure and joy. Whether dog-walking, selling crafts online, or using your professional skills part-time, a side gig can keep you engaged.
It’s no surprise many retirees struggle. Some people work into their old age, like Jiro, the sushi chef who kept going into his 90s. Others travel full-time. The common thread for a happy retirement is staying involved in something you love—gardening, writing, painting, whatever lights you up. I’m looking forward to having time to read more, exercise, and write, and I expect volunteer work will fit in nicely.
If you’re aiming to retire in your mid-50s, take a tip from my friend Fritz (The Retirement Manifesto). After 60 days of retirement, he says life is good. His advice: have a clear vision. Spend the years before retirement building interests and “bridges” to things that will last once you stop working.
As for me, I don’t plan to sling sushi or live out of an airport, but I do want a structured routine that feels more rewarding than my current one.
Post-script 8/8/19: I had coffee with a former colleague who took a retirement package a few months ago. After two months of loving “doing nothing,” he realized he missed his work and has since returned to the corporate world for a final five-year run. If you don’t plan what you’ll do in retirement, boredom might just push you back into a cubicle.