Getting From No Can Do to No, Can Do

On the scale ranging from cockeyed optimists to the-world-is-ending pessimists, I’ve always been firmly closer to the latter than the former. Nature? Nurture? I dunno. Prob’ly both. 

My parents were both muscle-flexing pessimists. Mom was all but a conspiracy theorist as to how people like us were destined to stay firmly under the heel of the people who so obviously rigged the system in their favor. Dear Old Dad doesn’t even know how to say the word “optimist.” This said, I think we’re all naturally wired to be more optimistic or pessimistic, and I’m more wired to be part of the latter contingent.

Pessimister

I’ve found that in the FIRE community, there’s lotsa pessimists. Many of us have been shaped by fear, which conditioned us to expect bad things to happen. And for any good times we experience not to last. 

We’re consequently cautious. In part because we’ve learned that reaching for the new shiny object is a bad wealth-building strategy. But also because we fear the sky falling. We’re so pessimistic that we game out all sorts of wildly far-fetched scenarios. And sorta disbelieve the math, even though we’ve learned it’s pretty solid. 

And we succumb to one-more-year syndrome. And then do so again. And maybe even yet again. 

And we plan to abide by the 4% (or whatever your more conservative desired number/flavor is), planning never to touch the nut spinning off income—that nut representing years of work and sacrifice—begging the question, why’d you save that money if you never planned to spend any of it?

Maybe it’s simply prudence and/or mere skepticism. But I think it goes beyond that. 

So, even once we start drinking the FIRE Kool-Aid, many of us—myself included—continue walking alongside our longtime companion, Mr./Ms. Pessimism. We think to ourselves, this FIRE stuff is really radical and it seems so simple, logical, straightforward . . . and doable. It can’t possibly work for me. Luckily, the bit of optimism most of us thankfully do have spurs us to also think to ourselves, “can it?

Always look on the bright side of life

Because for the first time in our lives we’re introduced to average-Joes/Janes using pretty conservative and easily understandable means (which, for many, also are replicable, the degree to which is subjective). A demonstration that it’s possible to reach A Goal. People who see/come to have seen a world of abundance and promise. And opportunities small and large, allowing for the option to pick and choose which they want to take advantage of. These people aren’t cockeyed optimists. They’re clear-eyed optimists. 

Sure, they’ll concede, there’s plenty that can go wrong. And setbacks may not be inevitable, but they’re likely. Because, life and human nature. But there’s plenty that can and will go right. And for those following a reasonable gameplan, the odds are stacked way in their favor. I mean, math is math and history is history. They’ll explain that you can go fast or slow. But so long as the direction is forward, you’re headed the right way. 

And you know what? They’re right.

I’d be lying if I said that I’ve become a cockeyed default optimist. But am I moving away from being a knee-jerk pessimist to becoming a kinda sorta clear-eyed optimist? To my great surprise, I am. 

Here are some milestones I’ve passed on the journey.

Revealing moments

First maybe was when I concluded that these FIRE principles are the real deal. I mean, it’s hard to argue with math. And as for the history, the lookback isn’t just 10- or 20-years, it’s far longer. There’s no recency bias. Once I bought the idea, I thought to myself, “gee, this crazy path really could work!”

Next was when our numbers started behaving as they should for those doggedly pursuing FIRE. Conceptual acceptance of FIRE became more concrete. Confidence begat yet more confidence. You might say that my confidence compounded alongside our numbers. Ahhh. see what I did there!

In time, I started bending my life’s arc in ways I’d never have dreamed of. For example, I’d long wanted to move out of the Midwest. But pessimism-–about finding a (well-paying) job, about things otherwise going right in the new location, about my own ability to finally take action, and more—always got the best of me. Once my confidence reached a critical mass tho, I not only acted pretty swiftly but (absolutely amazingly for a lifetime overthinker like me) with all but a devil-may-care attitude for the financial and job-related consequences. I was fully prepared to move whether or not I and/or The Missus had jobs lined up. And so we moved. Who was this optimistic idiot staring back at me in the mirror?

My optimism continued to grow, and a few years after moving, I set a date I planned to FIRE. At the ripe old age of 50. Less than six years from the point that I discovered FIRE. Crazy! 

How could it be that a dolt like me—someone with a hardcore scarcity mindset and driven so much by fear, and who, not long before, clung to his job as if it was a vital organ and who would’ve considered the mere thought of giving it up voluntarily (well) before traditional retirement age as pure nonsense—could make such a big, unconventional . . . dare I say, optimistic? . . . leap? Bananas! 

Transformer . . . more than meets the eye

Since FIREing more than two years ago, we not only didn’t immediately fall into a death spiral of complete and irreversible penury, we’ve avoided even the faintest whisper of such a fate. 

Now, I’ll freely admit that the investing awfulness that was 2022–my first year of FIRE—roused my pessimist soul. But never did that pessimism strangle my increasingly powerful sense of optimism and lead me to believe that all hope was lost and that I’d made a terrible and wholly avoidable mistake, as likely would’ve been the case for me not long before.

No, we kept calm and carried on, even if wincing and gritting our teeth. We took far-from-onerous steps to prevent sequence of returns risk from derailing us. Like my doing part-time, contract, and gig work. And drawing down our investments at a rate far lower than four percent. And not panicking, but rather looking unblinkingly and directly into the storm. 

I wasn’t just unruffled by the downturn (even if it and its timing greatly annoyed me), I knew that once over, we’d all but certainly recover . . . and then some. Heck, I was optimistic that all would turn out better than we could’ve thought. Far better. 

So far, we’re on track for that happy outcome. As I write this, it appears that we’re in the midst of a bull run, the length of which no one can know of course. It’s enabled us to recoup the lion’s share of our losses from 2022. Amazing!

And in the end . . . 

And there you have it. A brief history of how this one-time dyed-in-the-wool pessimist was converted by math, history, and—most importantly—experience confirmed by events, into an optimist. This said, let me reiterate that I’m an optimist of the clear-eyed, not cockeyed, ilk.