The Truth About Boredom During Early Retirement (and How to Avoid It)
I retired at 42. One of the biggest challenges of early retirement is figuring out what to do with your time.
Free time is only fun when you know what to do with it. Once the novelty wears off, the calendar starts looking like a blank wall.
Here’s what early retirement boredom really looks like, how I avoid it, and how you can do the same.
If you’re on the FIRE path, this is one of the major things you need to figure out. Having time is great, if you do something with it. Otherwise it is a curse.
Keep reading, this might save you years of boredom and regret.
Table of Contents
The Reality Of Boredom in Early Retirement
Many people who plan to retire early overlook the magnitude of boredom. They think they know what they will do with their time, but those ideas are only a few hours here and there.
Then you have the people who are “work optional“. Afraid to quit for fear of retirement boredom.
Another group consists of people who retired early and then returned to work because they felt bored.
I want to be harsh and clear here. If you need a job to keep you from being bored, then it is you that is boring.
This article will try to help plan boredom aversion during early retirement.
The Question That Reframes Everything
You can hit all your financial goals and still feel lost if your days don’t have direction.
For me, everything comes down to one question. I ask myself this. I encourage anyone that will listen to think about this question.
What Would I Do If No One Paid Me?
I asked myself that question well before I left my career in finance. No deadlines, no bosses, no meetings, no clients, just time. What would I do with my time?
The answer came fast: I wanted to be present. Not stuck on my phone or buried in a spreadsheet, but actually there with my kids and my wife.
She became a stay-at-home mom when our twins were born, and I wanted to join her. Not just weekends. Not just after 6 p.m.
Four years into retirement, I’ve been there through every stage. I’ve watched our son grow from a preschooler into an eight-year-old. I’ve watched our twins go from diapers to loud six-year-olds.
That time isn’t something you can get back later.
Related: I Retired Early: Work Optional Is Not Financial Independence
Being There Isn’t the Same as Being Fulfilled
But here’s what caught me off guard, being there didn’t fill the whole calendar. Parenting was a big part of my day, but it didn’t use every hour.
After the school drop-offs, after the lunches, there were still gaps. And those gaps got louder.
To stay grounded, I kept up my monthly streak of running at least one 20-mile long run each month. It started in 2019 and recently ended at 70 months.
I also write on DadisFIRE.com, sharing what I’ve learned as a CFA who left finance to become a full-time dad.
Those two habits gave my days some rhythm. But even then, there were still hours left wide open.
When the Routine Disappears
Most people underestimate how much structure a job gives you. When it’s gone, the hours stretch. And if you don’t prepare for that blank space, it can swallow your day, and your mood.
Video: The Negative Side of Early Retirement: 18 Hard Truths No One Talks About
Kindergarten is Coming
Our twins recently started full-day kindergarten, which means I suddenly have five full weekdays wide open. Before, I only had a few hours here and there. Now it’s 9 a.m. to 3 p.m. every day with nothing scheduled.
It is exciting. I had planned every dollar before I retired. I knew my investments, my spending, my tax strategy. But I hadn’t mapped out my time.
That’s where most early retirees get stuck. They think the hardest part is the money. It’s not.
I’ve seen others hit early retirement and spiral: boredom in retirement, second-guessing, even depression. They don’t miss the job, they miss the structure.
So I came up with a real system for how to use my time, not just enjoy it.
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Mapping Out “Things to Do When I Get Bored”
I don’t want to coast through retirement just reacting to whatever pops up. So I started building a personal playbook. Not a side hustle. Not another income stream.
Just a simple plan for how to stay curious, active, and engaged.
Capture Every “Someday” Thought
Whenever I catch myself saying, “I’d love to do that if I had time,” I write it down. If something lights a spark, it goes on the list.
I made a rule: whenever I have unstructured time, I just pick something off my “Things to Do When I Get Bored” list and just do it.
Climb an indoor rock wall. Build a small bookshelf in the garage. Rent a paddleboard and hit a quiet lake. I might even get my pilot’s license, a nod to a family tradition I never had time to explore during my working years.
Video: I Retired at 42: How I Think Differently Than People Still Working
Why Earning More Isn’t the Answer
Even with all this time, making money doesn’t cross my mind. Not because I don’t get offers, because I certainly do. Often.
But because retirement isn’t just about financial independence.
It’s about deciding where your time goes.
Turning Down Five-Figure Book Deals
Since retiring, I’ve been pitched everything from publishing deals to business partnerships.
A few times I’ve been offered five figures to my FIRE story into bestselling books. I passed. I’m not looking to jump into hustle culture under a different name.
I didn’t retire at 42 to keep grinding. I didn’t trade my time for freedom just to turn around and sell it again. If I write a book someday, it’ll be for fun, not profit.
No deadlines, no promotions. Just words on paper because I feel like it. That’s what freedom means to me now.
I also think it is incredibly hypocritical to write books, sell course, sell coaching, etc. saying you are retired early. If you are hustling to make money you are not retired.
Raising Kids With Purpose Too
This way of thinking isn’t just for grownups. I’ve started helping my son build his own “boredom list,” and it’s become one of the most rewarding parts of this next chapter.
My Son’s “Boredom List”
He’s eight now, and I’m teaching him that time is just as valuable as money. When he’s unsure what to do, we brainstorm.
He also has his own list of things to do when he is bored. My five year old twins don’t have lists. They are never bored.
Draw a comic. Build a robot from a kit. Write a silly story about our dog.
Instead of screen time by default, he’s learning how to direct his own free time. And he’s learning to do it early, long before adulthood turns free hours into mindless scrolling.
Related: How I Teach My Kids About Money Using a Lemonade Stand
Teaching Time Value Before Money Value
Most kids are taught to save their allowance and budget for toys. That’s fine. But no one teaches them how to spend time on things that matter. That’s what I’m working on with him now.
The goal isn’t to avoid boredom, it’s to build habits that make boredom irrelevant.
Related: Teaching My 5-Year-Old Twins About Money: Opening Their First Bank Accounts
My Streak Mindset Keeps Me Moving
Consistency beats ambition. That’s something I’ve learned again and again, not just in investing, but in how I use my time.
One 20-Mile Run a Month Since 2019
I’ve done a 20-mile run every single month since November 2019. That streak recently ended at 70 months. I’m not a marathon junkie. I don’t chase medals. I just run to keep my mind and body sharp.
The same idea applies to everything else I do now. My “Things to Do When I Get Bored” list isn’t something I plan to finish, it’s something I keep updating.
Try, repeat, refine. That’s how you build a life that keeps working long after the paycheck stops.
Related: What Does a Crazy Running Streak Have To Do With Retiring Early?
Before You Quit, Know What You’re Quitting For
Early retirement sounds like a dream until you’re actually living it. That’s when you realize freedom alone isn’t enough.
You need a plan, not for your money, but for your hours.
The Most Important Question in Retirement
If no one ever paid you again, what would you do with your time? That question shaped everything for me.
I didn’t need to find the perfect answer, I just needed an honest one. Then I wrote it down and followed it.
Build Your List Before the Paychecks Stop
Don’t wait until day one of retirement to figure this out. Start now. Write down your interests, your what-ifs, your “I’d like to try” ideas. It doesn’t have to be big or impressive. It just has to be real.
Because time is like money: if you don’t give it purpose, it disappears.
Related: Preparing for Retirement? This Checklist Helps You Avoid Costly Mistakes
The Boredom Problem Most Early Retirees Don’t Expect
Early retirement gives you time, but it won’t tell you what to do with it. That’s your job now. If you don’t make one, boredom will.
Avoiding boredom in retirement means replacing the structure work once gave you with something you actually care about. It could be a project, a habit, or even a small challenge that gives your day direction.
The smartest move isn’t just to retire early, it’s to retire with purpose.
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