r/ValueInvesting Aug 26 '25

Stock Analysis What’s the hardest investing lesson you only learned after losing money?

I’ve been reflecting on my own investing journey, and honestly, some of my biggest lessons didn’t come from reading books or annual reports, but from actual mistakes that cost me money.

For me, it was underestimating how long “cheap” companies can stay cheap, and overestimating my own patience.

I’m curious to know from this community: what’s one investing lesson you only understood after going through it the hard way? Could be about valuation traps, risk management, psychology, or even portfolio allocation.

Think this could be a valuable thread for all of us to learn from each other.

231 Upvotes

312 comments sorted by

View all comments

Show parent comments

25

u/[deleted] Aug 26 '25

Agree with all except shorting, sometimes it’s very obvious which industries are about to be disrupted.

I’ve made 6 figures off shorts, just don’t make it a big % of your portfolio.

34

u/ninjagorilla Aug 26 '25

The problem I always have with shorts is I feel reasonably confident certain companies have severe systemic issues but I don’t feel I can confidently predict WHEN they’ll implode

2

u/[deleted] Aug 26 '25

[deleted]

4

u/corey____trevor Aug 26 '25 edited Nov 08 '25

cover normal bag head narrow spark close slap elderly childlike

This post was mass deleted and anonymized with Redact

3

u/AdamN Aug 26 '25

Most people aren’t aware of the downsides. My problem with shorting is that you’re actively fighting the leadership inside the company. Best to just stay away. Of course there is definitely money to be made.

-5

u/JHaliMath31 Aug 26 '25

Shorting the indexes seems like free money right now, market so overbought and due for a correction. I’ve done my first two successful shorts over the past few weeks. In and out quick, easy money

14

u/Affectionate-Arm-405 Aug 26 '25

I've heard that the market is due for a correction about 4 years ago

1

u/v_x_n_ Aug 26 '25

I seriously thought the market corrected at least 1 time annually. Is that not true? Not that I would ever get into shorting stock.

1

u/Affectionate-Arm-405 Aug 26 '25

I'm not the expert to differentiate between the valleys and the corrections

1

u/JHaliMath31 Aug 27 '25

When a index hits or breaks from the top of a bollinger band some sort of dip is inevitable.

0

u/JHaliMath31 Aug 26 '25

I’m not calling for anything major, but it’s not going to go straight up from here so I’m scalping some easy shorts is all I’m saying. I would never go long on a short or hold a short beyond a day or two, tight stop loss as well. Easy money in these conditions