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Just wanted to pop in and say that I think Sean is absolutely right here. I've tried the ultra-cynical view at workplaces, and would have had better results with some "idealism", which he rightly notes in his form is just a more effectively action atop a base of clear-eyed cynicism.

However, I think we've got some tactical disagreements on how to actually make society a better place. Namely, I think Sean is right if you have to remain an employee, but many people just don't have to do that, so it feels a bit like a great guide on how to win soccer while hopping on one leg. Just use two legs!

My own experience, especially over the last year, has been telling me that being positioned as an employee at most companies means you're largely irrelevant, i.e, you should adopt new positioning (e.g, become a third-party consultant like me) or find a place that's already running nearly perfectly. I can't imagine going back to a full-time job unless I was given a CTO/CEO or board role, where I could again operate with some autonomy... and I suspect at many of the worst places, even these roles can't do much.

Also Sean, if you're reading this, we'll get coffee together before March or die trying.





> I've tried the ultra-cynical view at workplaces, and would have had better results with some "idealism", which he rightly notes in his form is just a more effectively action atop a base of clear-eyed cynicism.

Cynics feel smart but optimists win.

You have to be at least a little optimistic, sometimes even naive, to achieve unlikely outcomes. Otherwise you’ll never put in enough oomph to get lucky.


> Cynics feel smart but optimists win.

That's not been my experience. Optimists also tend to assume the best motivations behind the actions of others, and that will nearly always bite you in the ass in any sizeable organization.

I've been the ultra-cynic before, and agree that doesn't work either. People don't like working with you, and don't trust you.

I think we need to be realistic on order to be successful, and neither ultra-cynicism nor optimism fits the bill.

I would suggest that a healthy, reasonable amount of cynicism is a part of being realistic about how the world works.


Blind optimism is silly. But time and again we’ve shown that tit-for-tat is the best strategy in repeated games.

Start optimistic. Stop if it doesn’t work. In the long-term you don’t need to win every iteration, just enough for a positive expected value. And make sure you don’t get wiped out in any single iteration.

The weeks are short but the decades are long and the industry is smaller than you’d think :)


Optimists proclaim we live in the best of all possible worlds. Pessimists fear that is true.

Yea, agree with the cynics/optimists point.

Feels like cynics are right and optimists get rich.

I definitely lean more to cynic, my very good friend is def more optimist. He’s worth more than 10x me.


Are you certain about which way the arrow of causality points there? Your friend might have more reason to be optimistic because he is financially secure.

It's pretty obvious how an insufficiently cynical person could end up badly off - they could send all that money to that deposed prince in Nigeria, or whatever.

But the right optimism in the right situation can really pay off. Imagine you're pitching your non-technical carmaker CEO on a proposal to make a new pickup truck, and the CEO asks if you can make the entire thing with 0.1mm accuracy.

If you say "Yes sir, in fact many parts will be even more accurate than that" your project gets funded.

If you say "No, thermal expansion alone makes that impossible, it's also unnecessary" you're gambling on him respecting your straight-talking and technical chops.


Cynical take - if you know you're lying, that's not optimism, that's cynical manipulation.

A lot of people missing that cynicism isn't the same as sneering grumpiness.

You can be perfectly pleasant and charming while being utterly cynical about how you approach professional relationships.

This is a problem with at least two axes. The cynicism part relies on accurately calibrating the distance between official narratives and reality.

If you're a pessimist, you overshoot. An optimist undershoots. A realist gets it more or less right.

But if the distance is huge, that automatically makes the realist a cynic, because the reality is a lie, and in most orgs failing to take false narratives at face value is considered dissidence.

The strategic part depends on how you handle that. You can be sneering and negative, you can play the game with a fake smile and an eye for opportunity, or you can aim for neutrality and a certain amount of distance.

Sneering negativity is usually the least effective option, even when it's the most honest.

A realist in a functional organisation won't be cynical at all.


> Cynics feel smart but optimists win.

survivorship bias.


100% agree. Cynics can be always be right about the past, but optimists are often right about the future, because they are the ones actually building it.

The negative replies to this comment are ironic.


> but optimists win.

Win.. what?

> enough oomph to get lucky.

The underpaid cargo cult mentality is alive in well in corporate America.


Underpaid as in 200k p/a undrrpaid?

Have you logged into LinkedIn lately?

Nothing but pseudo "grindset" cargo cultists as far as the eye can see writing worthless technical platitude posts.

It feels like a parody site of itself these days.


That's all fake. LinkedIn is for sales and recruiting. If you see something there - a post, anything - it's meant to sell something. It's all as fake as the contents of an ad break.

It's important to note that many of those people aren't winning. What you're witnessing is the marketing equivalent of what random government software engineers produce. A good number of the people on HN would be trivially outearning those nerds

> > but optimists win. > Win.. what?

Depends what you want to win?

You won’t have happy kids and a good family life, if you don’t think it’s possible. Same as you won’t make a cool open-source library, if you aren’t optimistic (or naive) enough to go work on that.

And if you keep saying everything is impossible a huge drag extremely worthless and why even bother trying, you won’t get the fun projects at work.




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