Why retiring early is a dumb idea and what I learned from my mistake

Post by Why retiring early is a dumb idea and what I learned from my mistake

Have you ever noticed that there are two places where you can always find grumpy old men? The clubhouse and condo association meetings. 

They may have been grumpy old bastards their whole lives, maybe even from the very start, but I think that’s unlikely. I don’t run into many grumpy middle-aged men, but I have known far more grumpy old men than I’d care to admit. And I have a hunch as to why? 

They don’t Matter. 

Now before you get your underbritches all twisted in a bunch and start thinking I’m an ageist, or  that I have something against grumpy old men, I want to tell you, I don’t. I’m just making a general observation that if you meet someone grumpy, they're very likely to be an old man at the clubhouse or at a meaningless condo association meeting. 

These are the last citadels of Mattering for our unfortunate old friends. 

The real villain in this debacle is the western institution of retirement. You see, retirement robs us of a key ingredient for a great life. 

So why the hell would you want to retire early? 

I suspect retirement is a risk factor for Clinically Diagnosed Grumpiness, and so it follows naturally that early retirement carries the risk of Early Onset Grumpiness.

With hard work, careful planning, and good luck, I quit my job at 36 without any plans of returning to a job. I’m in the high risk bucket for Early Onset Grumpiness and not Mattering. 

I thought early retirement was fairy-tale-happily-ever-after stuff. Sadly, it’s much more middle-of-the-road. 

The spectrum of human well-being and retirement

According to Adam Grant, an organizational psychologist, we humans live our emotional lives on a spectrum from flourishing to depression. Adam has made a key contribution to the flourishing-depression-spectrum over the last year: he named the middle part. He calls it languishing. 

Languishing is a sense of stagnation or emptiness. You might feel a bit aimless, or a bit joyless. You might struggle to focus, or your motivation might be dampened. Adam thinks languishing might be the dominant emotion of our time. 

I think it’s always been there. 

I remember the movie Grumpy Old Men from the early 1990s. And Walker Percy’s The Moviegoer –1960’s Book of the Year – is the greatest work of art that describes languishing, although Percy called it “everydayness” and “despair.”

Percy opens his novel with a quote from Soren Kierkegaard: “The specific character of despair is precisely this: it is unaware of being despair.”

That description of despair is almost a mirror image of Adam Grant’s description of languishing: 

“Part of the danger is that when you’re languishing, you might not notice the dulling of delight or the dwindling of drive. You don’t catch yourself slipping slowly into solitude; you’re indifferent to your indifference. When you can’t see your own suffering, you don’t seek help or even do much to help yourself.”

No matter if it’s Everydayness, Despair, or Languishing. It sucks and it is a natural result of the promised land called retirement.

The languishing antidote

Adam Grant has a three part antidote to languishing: Mastery, Mindfulness, and Mattering. 

And once you understand these three concepts, you’ll understand that retirement, to a degree, and early retirement almost certainly, is a terrible mistake. 

Mastery is a sense of progress and is critical to our happiness. 

Mindfulness is the ability to focus on one task at a time.

Mattering is knowing that what you do is important to other people. 

Let’s get back to our grumpy old men at the clubhouse. Anyone who has ever played golf will know that it is a frustrating sport and can make the happiest of people grumpy for a bit. But let’s assume that golf actually brings some happiness into the old men’s lives. It makes sense. Golf is a game of precision and all games of precision lend itself to the pursuit of Mastery. Golf also requires your undivided attention, or that pearly white little sphere gets lost at the bottom of a dark, dark pond. 

It would appear at first glance that golf is a great pastime to help our older friends find happiness, or in Adam Grant’s terminology, flourishing. 

But what about Mattering? 

Is golf a legitimate avenue to Mattering? Perhaps. Grandfather’s teach grandchildren how to play golf. And that Matters. But I suspect that that is the exception. Not all grandchildren live in Florida over the winter, and we all know that all golfing grandfathers live in Florida in the winter. 

So I suspect that grumpiness is tied to languishing and that the sense of languishing is due to idleness and a lack of Mastery, Mindfulness, or Mattering. Hence, old grumpy old men don’t Matter. 

So why in the hell would you want to retire early and get grumpy early? 

A case study in early retirement languishing 

I quit my job at 36 without any plans of returning to a job. 18 months later, I’m here to report back that it’s not all ice cream and rootbeer floats. 

There’s a fair bit of languishing. 

Don’t get me wrong, there is pride and contentment in being able to choose what you do all day. But the promise of early retirement is way bigger than a sliver of pride and the mere satisfaction of designing my day to my little heart’s content. 

Now you might be thinking that I just sat around or didn’t know what to do with myself. I can assure you that I’m a prime candidate to be very good at early retirement. I have a lot of hobbies that I really like. 

The first one I really threw myself into was golf. I grew up playing golf and after a decade hiatus, I had two memberships, one to a course and one to a driving range, and played everyday for months. It was short lived. 

What’s the difference between a 9 handicap and a 5 handicap? Four strokes, I hear you say! Yeah, but it doesn’t Matter. 

Next up, I went surfing. I live next to one of the best beaches in the world and have always wanted to be a surfer. My father was a lifeguard on Santa Monica Beach – the Baywatch beach – and from a young age I thought being a surfer was the epitome of cool. So I dove in, and by dove, I mean I got pummeled by a thousand-and-one waves. 

I took courses. I got lessons. I improved.

Sense of progress? Yup. One step closer to flourishing. 

You also can’t take your iphone with you out into the surf. So I was filled with Mindfulness watching the waves come in. Searching the horizon for the next wave that would pummel me into the sand bar. There’s nothing that focuses your attention like the non-zero probability of drowning under the “Wave of the Day.” 

Big waves = Mindfulness. Another step closer to flourishing.

But it didn’t Matter. I’m not headed to Oahu’s north shore and Pipeline. I’m not Kelly Slater.

I never found a personal storyline that made golf or surfing Matter. But that’s not to say that I couldn’t have. I could have volunteered with the golf club’s youth groups or joined up with the mental health organizations that go surfing every Friday morning.

But I didn’t. 

The problem with early retirement is that your energy seeks meaningful outputs. It seeks a challenge worthy of your energy. Early retirement could be called energetic retirement. “Early” means you have ample energy for more. And you have so much extra energy that it will eat at you from within until it finds a worthy adversary. A 5-handicap didn’t meet my bar. Neither did volunteering.

So I beg you to reconsider writing in stone that early retirement is one of your life goals. 

The early retirement makeover plan

Instead of considering an early retirement, I have two suggestions for you:

  1. Mini-retirements
  2. Doing the hard work

Mini-retirements were made famous to me by Stefan Sagmeister’s Ted Talk. The main point of the talk is to not wait until you’re 65 to retire, but instead to take one year off every 7 years and work a few years longer at the end of your life. (Assuming you make it that far.) 

This one year off is used to refuel your creative bucket and inspect your life’s path. This was my intended path, but I’ve missed the one year deadline. It wasn’t my best decision. 

The hard work is the introspective probing to find what it is that you want to do, what will Matter. Because the truth is that Mastery and Mindfulness are easier to obtain than Mattering. Mastery is a sense of improvement and Mindfulness is focus. Those parts of your life may ebb and flow, or even wain, but with a little effort you can course correct. 

But Mattering is different. We change. Golf once Mattered. I was on the high school golf team and that Mattered. 

But in my mid-thirties, golf was joyous, and it didn’t Matter. 

The big mistake we make when we glorify retirement, at any age, is that we turn it into a core desire, which is to say that we postpone our happiness until it’s obtained. All of this is done without thinking about what we really want. We substitute the hard work of continuously triangulating what Matters to us for the allure of the lighthouse beacon: we mistakenly believe the bright light is everlasting happiness instead of a waypoint on our long journey. Happiness isn’t a destination. 

I’m anti-retirement for two reasons. First, it doesn’t Matter. Second, I’m not too excited to attend condo association meetings. I don’t want to be a grumpy old man. A far better path is to intersperse mini-retirements throughout life while working hard to always pursue what Matters. 

It’s hard work, but you won’t languish.

Share this article on social media


Dave Shepherd

Welcome! This is my online home, 'get started' to get a bit about me and what interests me.
Start Here