I find investing frustrating. Very frustrating.

I think this is normal, especially when you are young and there is so much uncertainty in your life. This is compounded by the diversity and volume of opinions when it comes to investing. I often find myself pulling my hear out (I have none left now) and changing my strategy every few years or so...

I boiled it down to my biggest 3 frustrations:

Life gets in the way. Having to liquidate your position because of Xyz f*cks up your strategy/returns.

Data is misleading. Statistics can be manipulated, correlation =/= causation, historic returns =/= future returns, etc.

Details matter but the bigger picture matters more! Things like taxes, charges, etc. matter a lot. But they don't matter unless you have the right overall strategy!

These are the ones I came up with. I'm sure they will change as I continue my investment journey but these are my biggest pain-points at the moment...

What are yours?

Edit - Nope no links / self promotion here.

trying to control greed, entitlement and impatience, not looking at stocks with a gambling mindset, as someone who just started investing for retirement about a year ago and a previous gambling problem.

Yeah, not falling into psychological traps is huge for sure!

Uber low “risk free” interest rates. A 10 year treasury yielding 0.66% gives you an income of $6600 per year on $1,000,000. In order to live off the income from your portfolio you are probably going to have to take on some risk if you could get by with a 3% yield. Therefore you have to spend some time analyzing and planning investment strategy that you may not want to spend time on.

True risk-free rates can be dangerous if used long-term and thought about properly...

Being right on a thesis but wrong on timing.

Yep, timing is important (but very hard/impossible). Also, think it becomes less important the longer your time horizon is.

"looking backwards" bias and similarly "anchoring to the past"... and again same lines, but "fear of regret" (oil will shoot up in the next year right AFTER i sell it)

you bought something at 40. it's at 20...... "maybe it'll go back to 40".."it should go back to 40"

It's like you try to do your DD and pick "good" stocks, but it seems no matter what you pick it will just go up with the snp 500 index or down with it, even if the stock is not a part of the snp 500. It feels like being a master chess player that is playing against a computer set to a moderate level. On your own you know you beat this program, but your moves are only averaged into an aggregate pool that comprises the move decisions of all other humans on Earth so you end up being crushed by the program because most people don't even know how the chess pieces are supposed to move.

Yep! Psychology, or the mental game, is one of the most frustrating parts- if not THE most frustrating part...

That's a fascinating way of putting it.

Do you think that the market is always "right"? Seems like you don't haha.

That's definitely true in the short-term but, if you do your DD correctly, I guess you just have to have faith that your stocks will out-perform in the long-term.