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So I'm going to chime in as a perpetual pessimist. I've found tremendous utility in expecting negative outcomes. I'm wording this very pedantically, because m

So I'm going to chime in as a perpetual pessimist. I've found tremendous utility in expecting negative outcomes. I'm wording this very pedantically, because my father and I used to argue past each other for hours re: "being negative vs saying something is negative." Perhaps it's just that I've been in Ops/distributed system maintenance and development, but I've found expecting a worst case/pessimistic outcome pretty much always leaves me far more prepared, and more often than not, ends up being more predictive than my optimistic peers. This has held true across time estimation, black box complexity, political outcomes, social overhead, model performance, outage frequency, pretty much every situation I can think of where I had to do long term planning in recent memory I feel well served by attacking from a "how is this going to go wrong/what are our blind spots/what do we do when this fails" angle. The primary reason I make the (socially risky) statement of this is that I very often get (no hyperbole) guilted for being a pessimist, even when taking nontrivial effort for the negativity to be actionable and focused. It took me a good few decades to learn how to wrap my words and beat around the bush, (I was told by managers early on in my career things verbatim such as "you need to toe the party line more.") but even now that I experience almost none of the social friction that I used to, I find myself frustrated by the inefficiencies and gaps in this manner of communication, and find these gaps almost immediately ameliorated when I'm on teams which have a much more pragmatic approach towards being pessimistic. Simply put, I had a very different experience than you, I've found an fixation on "being positive" to _massively_ impede Just Getting Things Done, and I've actually had much more luck bonding with coworkers over shared frustrations/issues and building lasting friendships like that than in teams where we're all wearing "let's be happy" masks. (This is a strawman, I don't expect you were arguing to this extreme, but I often find it manifests in this way in larger companies and as such want to try and argue the benefits of other angles of approach)

zestyping 8y ago
Thanks for talking about your experience in detail. There are many sides to this question and it's helpful to have a variety of well-articulated perspectives.
towelr34dy 8y ago
As a fellow pessimist, I thank you for such a well written piece. To add to this: I'm pessimistic that any of my individual efforts will succeed... I have 0% doubt that if I keep trying eventually something will work for me. I see everything else the same way. 99% of the time people are wasting their time. Though I'm not a Debbie downer, I tend to keep this opinion to myself. In general it is harder for me to cut loses than it is to join new projects. So I guess that's also why pessimism works for me. As someone once said: You've got to know when to hold 'em Know when to fold 'em Know when to walk away And know when to run You never count your money When you're sittin' at the table There'll be time enough for countin' When the dealin's done
bjelkeman-again 8y ago
My biggest successes have come from teaming up with people like you and people who are way more optimistic than me and cover both sides and balance them well.
nostrademons 8y ago
I think there's a happiness vs. success tradeoff with optimism vs. pessimism, and it works in counterintuitive ways. In my experience (both personal and with close family members), pessimists are happier but less successful than optimists. They're happier because if you already think the worst is going to happen, it doesn't take much to exceed expectations. It's the old "happiness = reality - expectations" saying: set expectations at zero and anything that happens makes you happy. There's also an aspect of taking control of risks and actively working to avoid them that you mention, which makes near term, immediate reality more likely to go their way. They're less successful because if you believe that most risks will turn out badly, you are less likely to take "leap of faith, have no idea what's going to happen" risks. Why would you, if the outcome is already known and will likely be bad? But in today's economy, many of the great successes come from taking big risks where you don't know the outcome and nobody else has the balls to try them. (This is a feature of markets: gains accrue to the people who supply what nobody else is willing to supply but which many other people demand.) So pessimists tend to make great technicians but shitty visionaries, while optimists tend to make great visionaries but shitty technicians. I've fallen on both sides in my career. I've found my biggest successes usually have come from leaps of faith that I was was willing to suspend my "This is totally gonna blow up in my face" belief for, but those opportunities come from and must be followed by periods of actually thinking about and managing all the ways that it could blow up in my face.
SZJX 8y ago
I think eventually the point is "just carry on doing what you have to do and get things done regardless of what happens". a stoic, stable and confident mentality which entails a lot of planning and calm decisionmaking helps. Either blind optimism or blind pessimism would be to the extreme and counterproductive.

zestyping 8y ago

Thanks for talking about your experience in detail. There are many sides to this question and it's helpful to have a variety of well-articulated perspectives.

towelr34dy 8y ago

As a fellow pessimist, I thank you for such a well written piece. To add to this: I'm pessimistic that any of my individual efforts will succeed... I have 0% doubt that if I keep trying eventually something will work for me. I see everything else the same way. 99% of the time people are wasting their time. Though I'm not a Debbie downer, I tend to keep this opinion to myself. In general it is harder for me to cut loses than it is to join new projects. So I guess that's also why pessimism works for me. As someone once said: You've got to know when to hold 'em Know when to fold 'em Know when to walk away And know when to run You never count your money When you're sittin' at the table There'll be time enough for countin' When the dealin's done

bjelkeman-again 8y ago

My biggest successes have come from teaming up with people like you and people who are way more optimistic than me and cover both sides and balance them well.

nostrademons 8y ago

I think there's a happiness vs. success tradeoff with optimism vs. pessimism, and it works in counterintuitive ways. In my experience (both personal and with close family members), pessimists are happier but less successful than optimists. They're happier because if you already think the worst is going to happen, it doesn't take much to exceed expectations. It's the old "happiness = reality - expectations" saying: set expectations at zero and anything that happens makes you happy. There's also an aspect of taking control of risks and actively working to avoid them that you mention, which makes near term, immediate reality more likely to go their way. They're less successful because if you believe that most risks will turn out badly, you are less likely to take "leap of faith, have no idea what's going to happen" risks. Why would you, if the outcome is already known and will likely be bad? But in today's economy, many of the great successes come from taking big risks where you don't know the outcome and nobody else has the balls to try them. (This is a feature of markets: gains accrue to the people who supply what nobody else is willing to supply but which many other people demand.) So pessimists tend to make great technicians but shitty visionaries, while optimists tend to make great visionaries but shitty technicians. I've fallen on both sides in my career. I've found my biggest successes usually have come from leaps of faith that I was was willing to suspend my "This is totally gonna blow up in my face" belief for, but those opportunities come from and must be followed by periods of actually thinking about and managing all the ways that it could blow up in my face.

SZJX 8y ago

I think eventually the point is "just carry on doing what you have to do and get things done regardless of what happens". a stoic, stable and confident mentality which entails a lot of planning and calm decisionmaking helps. Either blind optimism or blind pessimism would be to the extreme and counterproductive.