Today’s post is part 2 of a two-part series on boredom in early retirement. Last week we talked about the most important indicator of whether you’re ready for early retirement – go read that first if you haven’t already – and today we’re talking about what you can do to prevent that boredom in the first place.
One of the most common questions I get that I struggle to answer is, How do I find my purpose and discover things I enjoy doing if I’m already in early retirement? I struggle because I’ve always had the opposite problem: I enjoy doing way too many things, I’m always adding to that list and I see a million ways I’d like to make an impact in the world. My problem isn’t finding ways to fill my time, it’s narrowing things down. And in many ways my biggest lesson in the first year of early retirement has been that, even with all this newfound time, I’m still never going to check everything off my list. Not even close. (But I will add other things to the list which will be just as wonderful or even more so, so this is not bummer news. It’s just an expectation adjustment.)
We’re all different. Some of us have way too many things we want to do, some of us are completely consumed by one all-encompassing passion, some of us struggle to fill the time and I imagine there are some folks out there with varied interests who find exactly the right number of interests (but I have yet to hear from such a rare and special unicorn – please chime in if that’s you!). And a huge part of planning for and living a happy early retirement is knowing yourself — not just what your leanings are, but what that means for how you need to plan and structure your life in advance of pulling the ripcord.
We’ll talk all about that and more today, but first…
Revenge is mine, Carl.
Recording The Fairer Cents with Felicity from Fetching Financial Freedom, Bethany from HisAndHerFI, Jamila Souffrant from Journey to Launch and Julien and Kiersten from Rich and Regular
I’m not doing a full FinCon recap post this year, but I’m just back from Orlando where I had my favorite FinCon yet. The personal finance blogging and podcasting community is so inspiring, and I loved every second of chatting with people I’ve known for a while as well as people I met for the first time. It’s especially incredible to see the community diversifying and welcoming in people who don’t all look like white tech bros. I’ll save the bigger rundown for the e-newsletter.
And then there was the part where this happened.
I’m honestly still in shock. That is THE BIG AWARD at the Plutus Awards, the equivalent of winning Best Picture at the Oscars, and I’m so incredibly honored to win it, particularly given how many wonderful and dedicated bloggers were also finalists.
I wasn’t happy to do it, but I knew I had to scale back on writing while I was writing the book back in the spring and summer, and I also had to neglect comment responses during that period (though I’m back at it 100% now!), so in some ways it hasn’t felt like my best blogging year. But there are some posts I’m super proud of, the book deal that grew directly out of the blog and the big media reveal last year, all of which add up to something that feels massive, or at least massive for me. So a huge thank you to everyone who nominated Our Next Life, and an even bigger one to my peer bloggers who cast that vote, especially out of such a long list of heavy-hitters. What an incredible way to cap a life-changing year! I’ll just be over here walking around on a cloud…
In last week’s post on the most important (nonfinancial) indicator of whether you’re ready to retire early, we talked about using this question as a guide for yourself: What are you going to do with all your new free time?
If you have a clear picture of all the things you will or at least could do, great. If you draw a blank, then you especially need this post. But even those who have a big vision for early retirement need it, too.
Remember That Early Retirement Is Subtraction
I wrote this last week, but I will repeat it forever because it’s that important: If your life is boring now with work in it, don’t trick yourself into thinking that it will become less boring when you have less to do. Even if you have the worst job in the history of employment, it’s still true that removing work from your life will subtract something huge. And as I’ve written about before the last thing any of us want is a smaller life.
We do this to live a bigger life! And living a bigger life means not just subtracting work but adding something BIG, something that lets you use your brain and continue contributing to society in some way, even if that way looks nothing like the work you’re eager to leave behind.
It’s About More Than Boredom
It’s worth remembering, too, that subtracting work isn’t just about having new time we need to fill. It’s about all kinds of holes the absence of work or a career might create:
- A missing sense of contributing something to the world, even if you don’t especially love your work or like what you’re contributing.
- A missing sense of feeling useful.
- A missing sense of feeling good at something.
- A missing sense of workplace camaraderie.
- A missing way to define yourself or derive self-worth.
Even if you have lots of big visions of all the things you’ll do after you retire early, it’s easy to ignore all the holes you might suddenly find in your life, and you need something else to fill those, not just the empty time.
Enter Chapter Overlap, the Best Early Retirement Transition Strategy
If early retirement is, as I believe, more about transitioning from one chapter of life into another, then the best thing you can do for yourself is to find something that can serve as your primary bridge between one chapter – your working or career chapter – and the next. If you ignore this step, you’re more likely to find yourself bored or aimless or struggling with feelings of not being useful to anyone in early retirement.
That bridge is what I have inelegantly termed chapter overlap, the concept of making sure you don’t close one chapter of your life and then pivot to a new chapter without bringing anything major with you. Because it’s great to wake up in early retirement and ask yourself, “What do I want to do today?” But it’s not so great if you have to ask yourself, “What can I find to do today?”
And full disclosure: I did not anticipate this deliberately enough in my own early retirement planning, exhaustive and overthinky as it was. Instead, I lucked into it, because my chapter overlap is this blog and everything that has grown out of it. I wrote this blog while working, and I still write it now. And while I have zero plans to stop writing it, in many ways it has already served its purpose to me: It has given me a way to define myself without a career, a way to feel useful in society and a passion project that’s always here to fill my time. I suspect I would have struggled a lot more with all of those questions this year had I not had this blog to fill those holes for me.
How to Implement Chapter Overlap
Mark’s chapter overlap provides a great model for how you might think about shaping your own. The things he’s spent the most time on this year outside of just relaxing are his outdoors passions (mostly backcountry skiing, mountain biking and playing beach volleyball) and his volunteer do-gooder work. He has been involved with the local avalanche center for years, and last year took over the presidency, a volunteer position that comes with a lot of work. And so most of the time when he’s “working,” he’s really doing his volunteer nonprofit gig. But it’s work that makes him feel useful and needed, and work that’s good for the community because he’s helping spread messages about backcountry safety. The two things together – the sporty stuff and the thinky, do-gooder stuff – provide a great balance to one another, and give him a well-rounded life outside of hanging out and wondering when the real grown-ups are going to show up and shut this whole operation down.
In thinking about your own chapter overlap, all you’re really doing is seeing if there are things you’d like to do in early retirement that you can begin now, as a measure to head off aimlessness and boredom later. If you currently struggle to think of what those things are, don’t wait until retirement to ponder this question – do it now!
Some ways you might explore activities to try:
- Ask people who know you well what they see you doing.
- Sign up for community college classes in subjects that interest you and see where that takes you.
- Ask your friends what activities they’re a part of and ask if you can tag along.
- Click around on Volunteer Match or Create the Good and see if any of the volunteer opportunities listed there speak to you.
- Check out the local meetups in your area and attend some that look interesting.
- Check for free events in your local community calendar that might introduce you to a new hobby or passion, especially things like maker space open houses and volunteer fairs.
- Take a career inventory test and pay special attention to the results that seem like they could be hobbies instead of jobs.
- Read more! The more you learn, the more curious you become, and the more curious you become, the more ideas you’ll find yourself having.
Related post: Fostering a Spirit of Lifelong Curiosity // Staying Young in Retirement
The cure for boredom is curiosity. I believe that deeply. The people I know who are happiest in early retirement are curious, and they’re also the busiest. And while I don’t think that means you need to be busy to be happy, I think it reflects that those who are curious and stoked to try new things tend to dive into those new things and fill up their time with them.
If you know there are things you want to do in early retirement, don’t wait. Start a year or two before you retire, or even earlier. Not only will that make your life better today, because you aren’t deferring doing things you enjoy until some future that none of us are guaranteed, but you’ll also give yourself a solid bridge to your next chapter of life.
Give Yourself Time to Figure It Out
Whether you’re overflowing with ideas for what you’d like to do in your next phase of life or scraping the bottom of the barrel, don’t put this chapter overlap thinking off until you’ve nearly hit your magic number. Start now! Or at least start soon. Because you may not get it right on the first try. And you don’t have to get it right on the first try!
The more time you can give yourself to establish a hobby, a passion or a volunteer project that gives you purpose and a way to feel useful, relevant and connected to others, the more likely it will be that you find something that sticks, and that you enjoy enough to want to make it the thing that bridges the transition for you.
Mark often likes to tell me now that I don’t need to blog on a particular day. Like if it’s Sunday night and I say, “I have to blog,” he’ll always reply, “You don’t.” Which is true. But it’s also not true, because as soon as blogging feels optional to me, I know I’ll quit, or at least I’ll do it a whole lot less. And I don’t want that. So I don’t let it feel optional. I tell myself that I must do it, that it’s not a choice. And then I do it, and I’m always glad I did. When anyone starts blogging, no one is reading, aside from maybe a friend or two or an especially supportive parent (everyone wave hi to my dad!), and if I was just starting now, with no one reading and no one holding me to a schedule, there’s no chance I’d actually stick with it. I stick with it (mostly on schedule) now because it’s already an established habit, and there’s a reason outside of myself to stay at it. My chapter overlap has been the most important force in my life during this transition year, and I’m so grateful for the habit and for the community that keeps me going! (High five to past me who accidentally stumbled on this great idea!)
And that’s why it’s so important to start something well before you actually pull the plug on your working career. So that you get into whatever that something is deeply enough before you retire that there are people outside of you who care whether you stay at it, and keep you going.
The transition into early retirement is already complex and multifaceted, and the last thing you want to have to do while you’re already wrestling with how to define yourself and how to reshape your relationships is feel like you have nothing meaningful to fill your time.
What’s Your Take?
We’ve reached the end of the boredom series, so tell us: what do you think about all of this? Are you concerned about boredom in early retirement? Are you putting a chapter overlap plan into place? What other strategies do you have for heading off boredom? Any other thoughts? Spill ’em. :-)

