What George Didn’t Expect (And You Might Not Either)
George never imagined that he’d be bored in retirement, but he had to admit that he was.
Before he retired, he fantasized about how much he’d enjoy having all that free time.
He loved to play golf, but with work and home responsibilities, he never had as much time to play as he wanted. He could hardly wait to retire and play every day.
After going golfing every day for six months, he realized that he was bored. He was tired of playing golf.
Now what?
Is this all there was to retirement?
I remember asking myself the same question when I first retired. I’d spent years as an estate planning attorney, and suddenly I wasn’t that anymore.
I wasn’t helping people plan for their futures. I was just… here. With unlimited time and no idea what to do with it.
The fantasy of retirement—finally having time to do what you want—crashed into the reality of having too much time and not enough purpose.
That’s what happened to George. And it happened to me, too.
Why Does This Happen? Three Surprises About Retirement
Why would people be bored in retirement?
• Too much unstructured time. Working full-time provides you with structure in your life. Five days a week, you get ready, you commute to work, you spend all day at work, and then you commute home, deal with your home responsibilities, go to sleep, and then start all over again.
When you retire, all that structure is gone. Although you thought you never would, you can miss having some structure in your life.
• Loss of purpose and identity. People identify with what they do at work. That’s natural, since we spend most of our time at work.
Our answers to the question, “What do you do?” might be “I’m a medical tech,” “I’m a plumber,” or “I’m a manager.” But when we answer that question, we’re also typically telling the questioner who we are. We identify with our jobs.
When you quit working, that identity disappears. You also lose your sense of purpose.
I was an estate planning attorney for several years before I retired. My answer to “What do you do?” was also my answer to “Who are you?” When I retired, both questions went unanswered.
That silence was louder than I expected. I wasn’t helping people plan for incapacity and death anymore. So what gave my life meaning now? The question haunted me for months.
• Social shrinkage. We have a built-in social life at work. We spend at least 40 hours a week around people, getting to know and interacting with them regularly.
However, most work relationships don’t survive retirement. That can leave one feeling lonely due to limited human contact. That, in turn, can lead to boredom.
Four Ways to Break the Boredom Cycle
So, what can we do about this?
The good news is that boredom in retirement isn’t a life sentence. It’s a signal. It’s telling you that something is missing—structure, purpose, connection, or challenge. Once you recognize that, you can actually do something about it.
Here’s what I’ve learned—and what George eventually discovered—about breaking the cycle:
1. Reinvent Your Purpose
This is where most retirement advice falls short. Without a job, you have no built-in sense of purpose. You’ll have to go looking for it.
You will likely need some time to find a new purpose in your life. You might try working part-time, volunteering, or exploring your interests.
The key is to give yourself permission to experiment without knowing where it will lead. For me, that meant trying different volunteer roles before I found writing.
I failed at a few things first. That was okay.
2. Create Your Own Structure
When work no longer provides structure in your life, you have to create your own. Having no structure can make each day feel the same, waking up wondering, “What can I do today?”
Set times and days for things you do each week. Put them on your calendar.
For example, you could go to the gym on Tuesday and Friday mornings. Spend every Thursday morning volunteering at the public library. On Mondays, meet with a friend at a coffee shop.
3. Follow Your Curiosity
What are you curious about? Make a list of things you’re interested in, but never tried.
Set up a Tiny Experiment to try something on your curious list. Make a pact with yourself: “For X number of days/weeks, I will do Y.” See Anne-Laure Le Cunff’s How to Design a Tiny Experiment • Video Walkthrough, and her Tiny Experiments Worksheet for more details about how to do Tiny Experiments.
Don’t let the fear of looking incompetent stop you from trying something you’re interested in. When you begin something new, you are, by definition, a beginner. And it’s okay to make mistakes.
When you get to the end of your experiment, evaluate it. How did it go? Do you want to continue it, end it, or modify it? You can’t fail your experiment, because even discovering something is not a good fit for you is a positive.
4. Rebuild Your Social Life
Work will not provide the social relationships you had before.
You’re going to have to go out and make some new ones or renew old friendships.
You might want to consider joining a club with a common interest. You could also try volunteering, taking a part-time job, or taking a class. All of these activities expose you to other people and give you a chance to establish a new friendship.
Your Turn: Break the Cycle
Pick some practical actions to get started.
• Outline a light structure on your calendar.
• Set a date with someone you’ve been wanting to get together with.
• Plan a local mini-adventure. Be a tourist in your own town.
• Try a tiny experiment with something you’re curious about.
George eventually found his way through boredom by doing exactly this. He joined a local history club, volunteered at the golf course teaching juniors, and rediscovered why he loved golf in the first place—not because he played it every day, but because it connected him to people and purpose.
Your Turn: Which of these four moves feels like a good starting point for you?
AI Note: I wrote this blog post myself, using my own words and thoughts for the initial draft. I used AI only to suggest headlines, section headings, images, and text improvements.
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