What to Expect From Early Retirement

Uh oh. Feelings.

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.

Up next, I’m going to go off script a little and give you a special Christmas bonus - My 2024 Reading List.