What to Expect From Early Retirement
I’m sorry to say that early retirement will cause you to have feelings. A lot of them. Many of the feelings are good—freedom, joy, contentment, gratitude, excitement—but you don’t need help navigating those. Let’s talk about the tougher things you can expect to encounter.
Expect the Transition to Take Time
“Midway upon the journey of our life I found myself within a forest dark For the straightforward pathway had been lost.” – Dante Alighieri, Divine Comedy
First off, finding your footing takes longer than you’d think. I’m only now starting to feel like I’ve got my shit together, and that’s after more than three years of wandering (and wondering). This is consistent with what Bruce Feiler says in Life Is in the Transitions, whose research found that “lifequakes”—massive reorientations in one’s adult life—take an average of five years to recover from. So yeah, buckle up. Early retirement isn’t a “straightforward pathway”; it’s more of a “forest dark,” a journey with plenty of false starts, lots of aimless wandering and circling back.
Retirement more like a skill to get good at rather than a phase of life.
Expect Boredom
I’ve been bored a lot as I’ve transitioned into retirement. I’ve been restless and frustrated, lacking in purpose, unable to fill my day with any sense of challenge or meaning. And a bored Trent is an unhappy Trent.
To make matters worse, a bored Trent also has a greater risk of a heart attack. According to the Upside of Stress, “middle-aged men who reported higher levels of boredom were more than twice as likely to die of a heart attack over the next twenty years.” Terrific. Unhappy and dead.
But I’ve been thinking, boredom is clearly bad for our health in the long term, but maybe it is good for us in the short term. As John Naisbitt pointed out, “When there’s no silence, there’s no room for thought.” And I fill every silence—listening to audiobooks while doing the dishes, watching YouTube on the bike in the gym, driving with music blaring—rather than taking time to think and experience the world around me. Maybe I should appreciate the whitespace that retirement affords me, and give my brain some breathing room. Sit with the boredom. Get used to it. Use boredom as a catalyst for creativity and self-reflection.
It’s not natural for me, but hey, work in progress.
Expect to Be Hesitant of Commitment
Ironically, despite being bored, I still have a high bar for anything that reduces my freedom, anything that might take time away from the kids, or the chance to go adventuring for three weeks on the West Coast of the South Island, or join my friends in walking across Corsica. So, despite the boredom, I still say “no” a lot. I’m hesitant to commit to anything long-term, I’m afraid of of getting tied up, of reducing my options.
Expect a Lack of Motivation
You’ve heard the saying, “If you want something done, give it to a busy person”? Well, the opposite is just as true. Boredom has its own inertia, making it tough to find the motivation to break out of it. I stop doing things, then I stop wanting to do things, and before I know it, the inactivity spirals into an even deeper, depressive kind of boredom.
What’s worse is that being retired and financially independent means I hardly ever have to do things I don’t want to (aside from family and life admin, someone has to empty the dishwasher). It sounds like the ultimate freedom, but it can actually backfire when it comes to motivation. Sometimes I struggle to find the drive and focus for the harder things—things that need discipline, planning, and hard work. You know, the things that ultimately make life enjoyable.
As Anthony Bourdain memorably put it, “I understand there’s a guy inside me who wants to lay in bed, smoke weed all day, and watch cartoons and old movies..My whole life is a series of stratagems to avoid, and outwit, that guy.”
(Here’s one stratagem when you’re feeling unmotivated: Get one workout a day and even if that’s the only thing you do that day, you’ll feel like you did something good.)
Expect “Problem Creep”
If you’re not careful, you’ll fill your post-retirement days with meaningless tasks so that you can get a small hit of satisfaction when you cross something off your list. Damn you, dopamine!
There’s no avoiding the day-to-day minutiae of life—washing clothes, cleaning the bathroom, buying groceries, watering plants, vacuuming. And since you’ll likely be spending more time at home, it makes sense to fix the stuff around the house that annoys you. So sure, move pot plants, paint rooms, extend the back shed, restore the leather chair with the kitten scratches, buy art and lamps, and stain the deck.
But I found I had to be careful not to let the household responsibilities become my day. It’s tempting because the tasks are easy, benefit me and the family, and make me feel like I’ve done something with my day. Of course, many people enjoy the important work of homemaking, but I personally need more. I need to feel like I’m moving forward.
“But I had to clean my room yesterday!” – Ada, aged 6
What’s worse is that if you don’t have much on for the day, then the small things (I call them “mosquito tasks”) can take on irrational importance. Years ago, I remember my ex mother-in-law being completely frazzled because she needed to get to the Post Office by 5pm. She wasn’t sending anything urgent, but she was convinced that it had to be done that day: “Quick! I have to get to the Post Office before it closes!
There’s actually a term for this, “prevalence-induced concept change.” Essentially “problem creep”. From The Comfort Crisis by Michael Easter:
“As we experience fewer problems, we don’t become more satisfied. We just lower our threshold for what we consider a problem. We end up with the same number of troubles. Except our new problems are progressively more hollow….many people can find an issue in nearly any situation, no matter how good we can have it relative to the grand sweep of humanity. We are always moving the goalpost. There is, quite literally, a scientific basis for first-world problems.”
So, yeah, beware of problem creep.
Expect Solitude
As an early retiree, you’re going to be alone more. Not many people are going to share your circumstances, and most will be too tied up with work to join you for midweek adventures.
So, embrace it. I have spent a lot of joyful time hiking on my own, learning solo board gaming, and going to gigs by myself when I couldn’t convince others to join me.
“I love to be alone. I never found a companion that was so companionable as solitude.” ― Henry David Thoreau
Expect to Feel Guilty
Finally, and this is a big one, expect to feel guilty.
Growing up on a farm, I was taught the value of a strong work ethic early on. That drive stuck with me throughout my career—I’m ambitious, I set goals, I’m a striver. That work ethic is what got me to early retirement. But now that I’m here, it’s also what makes me feel guilty.
That guilt manifests in three ways.
I feel guilty when I’m not being productive. It’s hard to undo twenty years of producing. That’s why I feel guilty and frustrated that I haven’t “produced” anything much in my years of semi-retirement. Why haven’t I learnt te reo Māori? Or gotten a degree in psychology? Or gotten good at DJing? Ugh, has my time in the “forest dark” been frittered away? I haven’t produced anything concrete with my time—there was no output—have I wasted three years?
I love getting shit done
I feel guilty when I practise hobbies on a weekday. We’re conditioned during our prime working years to see hobbies as frivolous, unproductive distractions from “meaningful” pursuits. As the philosopher Alan Watt says, “Everything that is done playfully, without ulterior motive and second thought, makes us feel guilty.”
It’s true—I feel guilty when I’m learning to DJ, playing a solo board game, or clocking Diablo IV. It feels particularly indulgent and selfish if it’s during the traditional workday.
But if there’s an ulterior “productive” motive, like getting healthier or learning something new, then I have no problem—exercising or reading non-fiction feels perfectly justifiable. (And Sam, you’ve told me you feel guilty about reading during the day. Don’t. Even billionaire Charlie Munger said, “As long as I have a book in my hand, I don’t feel like I’m wasting time.”)
But maybe the guilt is misplaced. Maybe these moments of “unproductivity” are exactly what this phase of life is for. In the words of Oliver Burkeman, just maybe “some things are worth doing for themselves alone, despite offering no pay-offs in terms of productivity or profit.”
I feel guilty when I think about the things I ought to be doing. I also feel guilty about things I think I ought to be doing—a long list of self-imposed expectations. It’s not unique to early retirement, many of us struggle with the “ought to’s.” As a way to clear my head, I decided to write mine down in February 2022 and disinfect them with daylight:
I ought to be busy
I ought to be starting a new business
I ought to be on more boards
I ought to be doing more for society
I ought to be doing more for and with my kids
I ought to be helping more
I ought to be talking to my father
I ought to be connecting with my goddaughter
Seeing them on paper made me stop and ask myself: Are these things I really want to be doing, or just things I think others expect of me? Is this driven by genuine desire, or a sense of duty? The questions helped me realise that maybe I needed to let go of the guilt and cut myself some slack.
Mark the Transition – Managing the Early Days
The early days of retirement can feel exhilarating and disorienting. You’ve got all this freedom, but it can be hard to know what to do with it. Like many of life’s biggest changes, you can’t fully prepare for retirement until you’re going through it. But I wish I’d been a bit more deliberate about having something to retire to. Heading into it with no plan at all was a mistake.
I have five ideas to help you find your footing in the early days.
First up, you should mark the transition.
In the words of psychologist Jeltje Gordon-Lennox, rituals act as life’s punctuation marks. They give meaning. They can take lots of shapes:
Ordering from McDonald’s drive thru on the day I got my driver’s license, and being forced to drive around while eating a cheeseburger to ensure I could pass the eat-and-drive test
Greg, Travis, Phil and I burning our school notes after the final day of high school
Taking a babymoon in Kaikoura to mark the last time that we would be a family of three before baby Stan arrived
Buying a piece of art when I got divorced
So, one thing I didn’t do, but wish I had, was to perform a ritual to celebrate and mark the transition into retirement. Something tangible, like buying art, throwing a party, or even growing a beard, would have helped me feel like I’d crossed a finish line.
In conclusion…
When I’m giving advice and I start to feel advised by my own advice
The human brain is a funny thing—you can trick it, even when it knows it’s being tricked.
Take the Pomodoro Technique, for example. It’s a trick to beat procrastination: you set a timer for 25 minutes, promise yourself you are going to work solidly that whole time because you’ll get 5 minutes ‘free time’ once the timer goes off, and get going. It’s a trick to get you started, because starting is the hardest part. It doesn’t matter that you know it’s a trick, it still works.
Similarly, when you’re stuck on a decision, a good trick is to ask, “What would I tell my best friend to do?” It’s amazing how much clarity that question brings. Somehow, the choice becomes clearer when we think about our friends than when we think about ourselves. Distance brings perspective.
Which is to say, the whole time I’ve been writing this, I’ve been tricking me and I’ve been tricking you. You see, when I told you I was writing this advice for Sam—and for you—I was actually writing it for myself. It’s the purest form of self-help—disguised as helping a friend—but my brain didn’t seem to mind. Distance brings perspective.
But I’m sorry to say that we are nearing the end, I just don’t have much more to say about early retirement.
In fact, I think my next step is to un-retire. Four years ago I chose to step back from work and focus on the kids, and I wouldn’t trade that for anything. But now they need me for fewer hours in the day, and it’s time for me to stretch my legs. I’m not sure what flavour that’s going to take (hire me!) but with my innate ambition I know that early retirement isn’t for me. Not yet.
As for you, I have no idea why you are here, reading this advice I wrote for myself. Maybe you find yourself in a similar position as me, early retired and with an unexpected malaise, with the Four Horsemen breathing down your neck. More likely you’ve landed here because you’re interested in one of the topics I’ve covered to do with wellbeing, or giving, or money, or friendship. Well, I hope one or two things were useful or interesting. And if not, at least you know that you aren’t alone in thinking about these topics.
To send you on your way, here’s one final piece of advice on retiring early, from my 14-year-old:
“Have lots of money.
Figure out what you want to do when you’re at home all day.
Get a cat.
Develop a secret language with the cat.” – Ada
Reflect On Your Interests and Values
What are you going to do with all your newfound spare time? Well, I recommend that you start early retirement by reflecting on what truly matters to you. What activities energise you? What skills do you want to develop? What intrigues you? What causes do you care about? How do you want to impact the world around you? What’s important to you?
It’s important to capture these interests and values in writing, as crisp as you can. Writing is an excellent way of thinking.
Some answers will be on the tip of your tongue, but others won’t reveal themselves to you until you’ve put in some deep work. “Reflect” is a deliberate verb in the header here—writing down your interests and values once won’t be enough. You need to revisit, refine, and adjust them. The work is worth it. A well-considered list will guide your priorities, screen your decisions, and shape how you spend your post-retirement days.
Maybe try this guided, step-by-step process to help uncover your personal principles if you’re not sure where to start. Otherwise, there are lots of lists online to help you consider your most important values. Or you could even engage ChatGPT in an interactive dance:
I’m reflecting on what truly matters to me as I enter early retirement, and I’d like your help. Can you guide me through a series of questions to help clarify my values, interests, and priorities? Please help me think through the following areas, one by one:
What activities have energised or brought me joy in the past, and how might I incorporate more of them into my life?
What skills or talents do I want to develop or refine in this next phase?
What topics, causes, or ideas naturally intrigue me, and why do they hold my interest?
What causes or issues do I deeply care about, and how can I contribute to them?
What kind of impact do I want to have on the world, my community, or the people around me?
Feel free to expand on my answers and ask follow-up questions as we go.
Here are my values, which I drafted in 2012 and keep tweaking:
Love PEOPLE and be part of a COMMUNITY:
I want to share my life with a small group of family, friends and workmates who I care deeply about.
I want to connect people to one another.
I always want to be able to make conversation with people, regardless of their position or background.
I will do my best to think the best of everyone. I will expect the best from people, and believe in them.
I will strive to be a decent human: honest, loyal, kind, willing to admit mistakes.
I will be the best Dad I can be.
Actually, maybe I want to be the Okayest Dad I can be…
Learn And Grow:
I want to keep learning about things that are interesting and important.
I want to experience other cultures and other countries.
I want to mentor and be mentored.
I want to cultivate varied interests and have the time to pursue them.
I want to be really good at what I chose to do. More than competent.
I want to be better today than I was yesterday.
Make A Difference, and do something important and worthwhile:
I want to live life on purpose.
I want to be part of something that’s bigger than myself, part of a team that is making a difference.
I want to change things for the better.
I want to inspire and encourage others. I want my kids to be proud of me.
I want to labour to do good rather than be rich.
Get Stuff Done:
I want to build stuff and solve problems.
I want to be passionate about whatever it is that I’m doing.
I don’t want to waste my life force in meaningless meetings, political arguments, commuting or with negative people who suck up my energy.