Strategic Pessimism, or: Don't be afraid to care

What if it doesn’t work out?

This question, on the surface, seems like a very reasonable inquiry. To shelter you from whatever lies on the other side of uncertainty, considering failure ahead of time feels like a smart move, a wise discernment. And to get in the caveat right away: I’m not saying that “What if it doesn’t work out?” is the devil in question form and should be forcefully removed from everyone’s mind forever.

When applied consciously (for example by conducting a Pre-Mortem), it can spark some phenomenal insight and help learn from your mistakes before you make them. Great stuff. But you know, the mind is tricky - and sometimes it loves to dress up folly as wisdom. Or in this case, dress up fearful avoidance as wise discernment. When it goes from a question to a way of life, you start living life with the handbrake on.

This is the story of how I discovered Strategic Pessimism. How what I thought to be an action-oriented tool revealed itself to be a maladaptive emotion regulation strategy, or in other words: It left me living at a comfortable distance from reality, never making contact so I don’t run the risk of feeling something. So, let’s get into it:

Falling

There’s a reason why it’s called falling in love - and not descending into love at a reasonable pace with adequate safety equipment. Getting to know someone who turns your world on its head is rarely a controlled effort - more like a continuous stumble into the unknown. But what happens when you try to take control of that stumbling, continuously reminding yourself that you might very well stumble straight onto your face? Well, I’m just gonna be a bit cheeky and open my journal to the page I first recognised this:

For the first time in a while, I get to see this tendency of mine crystal-clear: To avoid disappointment, let me caveat a good thing. “It might not work out.” Yeah, but what if it does?

I’m entirely aware that the outcome of this is uncertain - but that’s what makes it so beautiful. So what’s the point behind this down-playing? It’s merely a mechanism to protect my fragile little ego from a potential hit. If I just adjust to the fact that it might not work out today, I won't be hit as hard when it inevitably doesn't. Great idea - but at what price?

In a sense, it is the epitome of this cherry-picking idea I wrote about the other week. By trying to avoid experiencing the low, one flattens the whole wave. Makes life more dull, less vivid. Prevents oneself from experiencing the full beauty that life has to offer.

So, wait? There’s a price to this? I’m not just reaping the glorious rewards of my wisdom? That’s a bit disappointing - but okay, what could that price be then? Well, aren’t I lucky that I did all the writing for this last year. From the same journal entry:

The price, I believe, is twofold. One facet is action-oriented, one relates to perception.

Perception first: The way you experience reality is dictated by your questions. Completely unrelated to what things might “really” be, all you ever get to see of it is what you allow yourself to see. So this point remains independent of whatever trajectory this may take: If I repeatedly tell myself that this might not work, I’ll never get to feel the authentic, genuine nature of what this could be. That incredible state you were in when you met [😏] for the first time. It might’ve been naive, but the fact that you genuinely believed there might be something beautiful there was incredibly conducive to what it became.

This leads perfectly into the second point: Action. Not only are you robbing yourself of the experience but you’re also sabotaging the chances of the journey taking its trajectory. The way you think changes the way you act. So if you’re too reserved, to fearful to truly engage - who knows where it’ll go. Worse - who knows where it could’ve gone if you didn’t pull the handbrake? It might not work out. But what if it does?

Living with a Handbrake on

It might not work out. Or in this case, it didn’t work out. But guess what: It sucked for a little bit and then inevitably passed (Hello, Impact Bias) - and here I sit today, alive and well. I’d be willing to take the fall 100 times over a life of wondering “What if I wasn’t so avoidant?”. But in the moment, the prospect of “being realistic” and avoiding this apparently irrecoverable hit by somehow just suffering it in advance (the logic really sounds backwards when put like this) seemed oddly alluring. It’s choosing the devil you know (which is gradual dullness) over the potential of a devil you don’t, completely underestimating

1. your ability to cope with that unknown devil and
2. the potential upside of a life without the perpetual handbrake on.

And this is the thing: Strategic Pessimism isn’t limited to avoidant attachment. After I recognised it here, it started popping up everywhere:

In my work, I found myself in the uncertain vacuum of being able to take the company wherever I could imagine it. But instead of committing to the 100% solution and risking the dread of falling short, I found myself caught in mediocre expectations. Once again from the journal:

In a sense, I can see the same defence mechanism of Strategic Pessimism here - just dressed up as “comfort”. Yeah, this might not work. But what if it does? Genuinely, what if you allow yourself to dream even for a minute the way John does?

You’re absolutely gonna be able to stomach the fall. But are you gonna be able to stomach the regret of not giving it your all? I’d rather not find out.

A few months later, I sat there wondering why the place I’d chosen didn’t really feel like home, and I found a familiar perpetrator:

I walk down Alex Pde, observing the whales breach from the vast ocean while sunlight kisses the palm trees no more than 200m from my flat - yet I walk through this scenery like someone passing through, in transit, foreign to it. But isn’t this home? Isn’t this exact scenery what made me stay in the first place? Don’t I feel like I belong here? So why am I not allowing myself to truly connect with it, become absorbed in it?

What’s keeping you then from engaging in a real connection with the place, no matter for how long? The fear that you might miss it when you’re gone? Well, that mechanism you know all to well, don’t you?

To feel at home here, you must allow yourself to feel at home. This is simply a matter of conscious, deliberate perspective.

I feel like this is the mechanism that’s made us a generation of aloofness. If you don’t care, you can’t be affected. But what lies on the other side of caring? Isn’t caring worth it sometimes? Yeah, when a loved one passes away you have to go through grief - but is that a reason to never love? Is the answer to preemptively keep yourself from caring? I don’t think so. So, in the words of Pink Floyd: