Our Changing Definition of Early Retirement and the Power of the Freedom to Fail

I used to be super hardline about the definition of early retirement. “No work,” I’d insist. Not quite to the retirement police level of accusing others of not actually being retired if they did some post-career work, but I only considered it retirement for us if we had no employment and no active income pursuits.

It wasn’t an unreasonable thought, actually, given that that was back when we were formulating our plan and timeline, back when we thought retiring in 2020 was a super ambitious goal (and it was, but then we got super duper ambitious). And I was looking purely at the numbers.

“Right now, our hourly rate for work is X. And if we need money in retirement, we’ll have to work, like, 10 hours to make X,” I’d reason, probably exaggerating a bit. “So why don’t we just work until we have enough to never need another cent, and be as efficient as possible with our earnings?”

Sound logic, right? Mathematically, my hardline stance made sense. Where it didn’t make sense is in the actual realities of early retirement, or at least our early retirement, something that has been slowly revealing itself to us over these past few years, especially because blogging makes us ruminate on early retirement far more than someone else might (and maybe more than anyone should). ;-)

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Today we’re exploring our changing vision for and definition of our early retirement, and talking about the power of the freedom to fail — something that we’ll enjoy in abundance in retirement, and which has made it possible to achieve early retirement in the first place.

The Early Days: Retiring From Something

Back in those initial years of our early retirement pursuit, when we hadn’t yet gotten aggro about knocking off milestones left and right, when we were still figuring out whether this questionable notion was even possible, our thoughts about early retirement reflected a common theme:

We were focused on retiring from work. 

That’s all. We knew we didn’t want to work forever. Work was stressful and all-consuming, and we wanted the opposite of that, whatever that was. (And we were tired, and early retirement seemed like it must come with more sleep.)

What the opposite of that — of work — actually was, we gave that far less thought. It vaguely included more time in the mountains, but that’s as far as our thinking went. Still, that was enough to jumpstart our research and planning, and put us on the journey we’re nearing the end of.

The Later Days: Retiring To Something

As the years have passed, though, we’ve started to see more nuance in our vision for early retirement. Especially after we left the big city and moved to a small town in the mountains, we started realizing that our choice to move here meant we’d get tons more time outside, but perhaps at the expense of some of the intellectual stimulation we’d enjoyed in the city. Not that there’s not an endless amount to learn about the geology and wildlife here, and plenty of stuff to geek out on like the various aircraft used to fight wildfire and how they all coordinate (just to use a totally non-specific example I definitely didn’t ask a US Forest Service firefighter 5000 questions about earlier today), but the culture’s different. People just want to talk more about their outdoor radness or next epic adventure, involving at least 10 hyperbolic overuses of “epic,” as they should, because look out the window.

But over time, we realized that we might miss that part of work. The constant interaction with super smart colleagues and clients. Having to stay current on the latest relevant news. Being forced to address challenges we wouldn’t otherwise choose to tackle, keeping our minds sharp. The feeling of having created something.

As this realization has slowly bubbled up, we’ve also put a lot more thought into what we want out of the rest of our lives. How we define our purpose, what that means for what we want to accomplish, all the places we want to travel and adventures we want to have for as long as we’re able, what we want an average day to look like, how long we want our trips to be.

Over time, a very crisp vision has emerged of what we’re retiring to. And that vision includes work.

Our Revised Definition of Early Retirement

What we’re envisioning in the next stage is not work as we know it now, certainly nothing substantial that would fall under the category of “employment.” But by just about any definition, it will still count as work. We’ll take on things that then become mandatory to do, though on our own time as much as possible. (There is no part of me that wants to have to show up at a specific place at a specific time, at least for a good, long detox period.) Plenty of folks have already told me that this blog counts as work, and I plan to keep going with this, and with other related projects.

Our definition of early retirement now looks something like:

Owning our own time, making decisions about work to take on based on intangible factors like how interesting something is or how much it benefits others rather than money, and no longer striving for advancement. 

Owning our own time has become the most important aspect for us, not “no work.” Not all work is bad, and we plan to keep doing some of the parts of it that we’re awesome at, but only in ways in which we can decide when to put in the time, and that we can do from anywhere with an internet connection. We feel strongly that we don’t want post-retirement work to stand in the way of our travels or adventures, or to cut into our outdoors time.

So the work we do in retirement will probably look quite a bit like the work others do in the gig economy. Projects here and there that sound interesting with a baseline of ongoing work. But there will be one difference, the importance of which is impossible to overstate:

Unlike almost everyone else on the planet, we will have the freedom to fail at whatever work we do in retirement.

If we try something and suck at it, if the economy turns south and there’s no market for what we’re offering, if what we put out there is just bad, we’ll be fine. A layoff, a recession or a skeptical market might bruise our egos, but it won’t hurt us financially.

So while our work may look like a lazy form of hustling, we will be entirely unlike virtually all others out there hustling because success for us will be counted entirely in how fun, fulfilling and worthwhile something feels, not how much it earns for us.

What an incredible privilege.

The Power of the Freedom to Fail

As we’ve reflected more on all the ways early retirement will impact our lives, we’ve realized that the power of the freedom to fail is perhaps the most powerful. Most people in the world have to make decisions through a constant cost-benefit analysis, weighing how much something might earn them, their limited time and resources, opportunity costs, the well being of their families, and dozens of other factors to make responsible decisions. (It’s always worth a quick visit to the Global Rich List to get grounded on how little most of the world has. Lower middle class in the U.S. equals super rich in the world.) But we’ll get to make decisions based almost entirely on fun.

On a basic level, you’d never take a job without knowing how much it pays, right? That’s the rational thing to do. But we’ll be in a position to “take jobs” regardless of what they pay, perhaps without even knowing! (And by “take jobs,” I really mean “pursue cool projects we want to do without worrying about whether they’ll make us money.”)

But we’ve also realized through all of this that the power of the freedom to fail won’t actually be new to us. Though we won’t have had the luxury before of not having to work for money, or of being able to do any work no matter how poorly compensated, we’ve had the freedom to fail in other ways.

When I was in college, I would often say something that I both still wholeheartedly agree with in an idealistic sense, and cringe at, knowing how much unacknowledged privilege was embedded in it: “College is for finding your passions and enriching your mind, not for getting a job.” I would not have been able to make that statement if failure wasn’t an option for me.

Obviously I didn’t want to fail and no part of me believed I might, but if I struck out at finding a job, I could always move back home and mooch off a parent. If I ran out of money, I couldn’t expect full support by any means, but I could have gotten a little help. And I had other backup options like credit cards I could charge things to, something not everyone has at their disposal. I recognize now that, even if I didn’t think consciously about that safety net, it freed me to make a very different set of choices and to view things entirely differently than if I hadn’t had it.

Most of us who are even in a position to consider early retirement have had much of this freedom to fail all along. People who grow up knowing that there is no fallback option, no one who can come to their rescue, have out of necessity a very different set of decisions in front of them. It’s far harder to justify studying some frivolous liberal arts subject (English majors, what’s up!) if it’s not clear how that course of study will lead to immediate employment after graduating. And it’s a lot more ridiculous to bemoan the indignity of having to show up for work every day if you know that job is the thing ensuring your survival. (Fair warning, I will tweetstorm at the next person I see complain about being a victim for having to work, like, you know, almost every other human being on the planet.)

All of this leads us back, as almost all of this thinking does, to gratitude. To how fortunate we are to be able to pursue early retirement, how lucky we’ve been in being able to make so many of our decisions in life up to this point, how much more fortunate we’re about to get when we pull the plug later this year. We’ve absolutely worked hard to make things happen for ourselves, but we’ve had a strong wind at our backs, something not everyone else benefits from. And we’ll never stop being grateful for that.

Let’s Discuss!

Has your definition of or vision for early retirement shifted significantly over time? How do you see work fitting (or not fitting) into your next life, or your current life if you’re already retired? What parameters would you put around future work for yourself so it still feels like you’re living on your own terms? And on the freedom to fail — what decisions have you been able to make in life that not everyone can? And anyone who’s pursuing early retirement who didn’t have any family or community safety nets? We’d love to hear from people with all kinds of perspectives, so share, share away in the comments!