Overly Pessimistic / Think Everything is A Short

you need more reps. had similar my first few years, not helped by having worked on some large frauds to begin. with more experience you develop more discretion, you know what the market will and will not care about. get the reps. 

Permashort strikes again

Honestly I think it’s hard once bit by the bug. 
 

I have a thought which may help though. Psychologically we don’t like inflation. (look at how the world is reacting to higher prices across the board)

same applies to asset pricing.
 

Things are “too high” but relative to a mean which you are comfortable with pre-inflation.   
 

now don’t get me wrong - there arguments to be made risk assets are overvalued; but the fact is they have been for a long while and there’s no physical law that drives a return to the mean when this gets out of whack on a multi-year basis (it’s instead driven by geopolitics and complexity no one can really accurately predict). 
 

but if your problem is things always look expensive, it’s because you’ve anchored to a regime where they weren’t. You’re in a different regime now and unless you want to start speculating on regime changes (which is different to individual asset prices), then make peace with it.

One of our short guys has the same traits. He labels every other mgmt team as scumbags and every other business as fishy. I take what he says with a ton of salt, but I don't want to mess with his head as he's good at finding shorts. Well... his hit rate is poor but his slug is great and he makes money as he keeps pressing his shorts which more then makes up for his many LSD losers. 

Not sure if you invest absolute or relative but regardless, it could be helpful to have a framework and bias checklist that helps mitigate anchoring as setarcos wrote. 

Perhaps it could be helpful to ask yourself:

• Am I dismissing consensus purely because it's consensus?
• Am I overweighting low-probability negative scenarios?
• Is my contrarian view based on unique insight or just contrarianism?

I personally find it helpful to break down my analyses in to steps where I can sense check each step before spending more time (go / no go). Sequential growth drivers - decompose recent growth, what can be re-underwritten again, what's deemed cyclical / one-offs / declining and why? What evidence do I have to prove that it's a) it's cyclical / inflated and b) not priced in already (e.g. what's in the revisions, assuming it's hasn't been purely re-rating).

If the return profile is ERP-esque (~10%) on 1 yr forward, discounted back to NPV, then the market is usually pricing in the fundamentals to the markets perception of fair value "i.e. no relative upside / downside" vs. the SPX. Then it's all about probability weighting and moving away from binary decision making. Dynamic sizing over your holding period within certain "levels" should help. 

who cares, this is supposed to be quantitative industry. Set performance, hit rate, alpha targets etc for yourself and with your senior people, manage to that, try to make it better. Really tired of being told I’m supposed to play some performative song and dance of humility everytime some C-tier sell side notes comes out w/ boiler play spin form shit-co management. Is this supposed pessimism a problem evident in your decision making and alpha production relative to teammates? I’m short focused. I’m generally a happy guy but pessimistic. Most people are pretty dumb, even more (esp at mgmt level) have the perceptions totally muddled by a big dangling equity carrot and live in a bubble of their industry peers. And also plenty are liars. A lot are super smart, brilliant great and capable operators - I don’t make those short positions.