Please share so that we can reflect and learn 
My two regrets are related to not buying houses.
No other regrets.
Investments strategy is 80% global ETFs buy and hold and 20% “cash”.
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Not buying real estate in 2010 - and too high share exposure before/in the GFC.
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Starting to invest very late in life
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Suppose you had held on to an investment you bought that went on to do 10’000x.
Yeah. That one.
Being a PC gamer and knowing about BTC back in the days when it was still in the 1-10$ range. But thinking „what kind of crap idea is that?“ and moving on playing videogames instead of mining millions in todays dollar.
Then later using a 3080 and 3090 to mine ETH and double down by buying even more ETH. I‘m still holding those 5.5 ETH which could have been 0.4 BTC too.
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Here’s my top 3:
- Forced exit of home ownership due to divorce in 2009 (missing out on 400k gains so far)
- Investing in Russia and being hit by sanctions in 2022 (34k unrealized losses)
- Limping away from 2008 and exiting the market in 2012 and realizing 30k losses, then waiting until 2017 until restarting to invest
S&P500
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Biggest regrets: stock picking, not investing in gold and BTC
Proudest achievements: stock picking 
, time in the market instead of timing it
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- Starting too late
- Chickening out/not buying enough/selling (nVidia, other single stocks)
I have two main regrets:
- starting to contribute to my 3a not from the beginning of my career;
- only becoming aware of my spending around age 30, nearly ten years into my career.
I regret having had regrets.
I probably spent thousands of hours trying to optimizing things that cannot be optimized. Once it was clear to me that you simply cannot trade lows or highs except for pure luck, things started to change for better. As a typical Swiss I searched for compromise. Not highs, not lows, but nice wins and low losses.
But two examples from the 90s always come to my mind. I had two stocks with more than 100% gain. Spanish Telepizza and Priceline. Telepizza had a going private, made a few 100%. There are shops now in every corner of Spain, was exactly the right product at the right time… and the pizzas are actually good.
But the real hammer was priceline. By then you could put an offer for a plane ticket, a hotel or for renting a car. Original and worked. then they merged into booking.com and I would have made probably a few thousand times what I sold for.
The biggest mistake in investing is not buying crap. It is selling too early. One of my mottos therefore: “hold as long as possible… but not longer”.
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You keep repeating this,
But I keep not understanding.
What makes the stock “not possible to hold any longer” for you?
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Not having implemented an investment strategy as early as May 2020 when I had taken care to educate myself on the issue during April 2020, the month I learned about this forum and the importance of keeping a budget to save and invest those savings to become “rich” instead of holding cash in a 0% savings account.
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Not investing in Bitcoin in 2017 just after it crashed, even though my brother had started researching it as part of his Master’s degree. At the time, just after the crash, I also thought it was just another scam.
When I have to sell. The details depend on the strategy and all strategies do implement “hold as long as possible but not longer”.
As I said, it is pure luck to trade on highs or lows. I use a point system to decide what to sell. And I always hold at least 6 months, so I adhere to the Swiss non-professional status rules.
I trade a dividend system which always finds enough good stocks to buy. So it is a pull system, whenever a position is sold a new one is opened.
Then I trade a momentum system which hardly finds any stocks to buy. This is a push system, whenever a position is bought something else is being sold.
It is a bit more complicated because of money management with margin. But basically this is the idea. Hold as long as possible, but not longer. No need to keep a loser forever, but you can only lose 100% (which I never did), and you can make many 100% (which I do quite often).
Wanting to buy a house short term, market going down exceptionally steep just in that time frame, selling so I could still afford the house, deciding not to buy the house, stock market had recovered by then, not wanting cash laying around > reinvesting in the same stocks I sold before effectively loosing a painful amount of money
This is a regret story, although I am not sure what I should have done differently.
I guess the problem always is when you need liquidity short term. But sometimes opportunities arise that you didn’t plan for..
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The optionality value of cash is often under-estimated.
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I only have one major regret:
I invested 3’000 USD into NVDA in January 2024, just when it started to pick up heat.
It was one of my first investements, and oh boy was I happy when I sold it all a week later with an AMAZING GAIN of… 140 USD.
I remember how back then that was considered a huge gain for me.. oh how the times change.
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Investment regret consists essentially of just hindsight?
Why would there be any major lessons in reflecting and learning?
Anyway, in the spirit of sharing investment mistakes – accidental or with conviction – as this thread seems to have turned to this theme: selling my GOOG shares eventually, once I realized that holding on to vested company shares was keeping all my eggs in one basket.
Had I held on to my stock awards, I would be well into 8 figures in CHF (with GOOG dividends now, too). I did sell, to buy Goofy’s personal and custom ETF, providing Goofy with a steady and increasing income … but, well, the sequence of return risk wasn’t really much of a risk with GOOG, hindsight applied.
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For me not at all. For me it’s when I could have taken a different, better decision with the informations available at the time.
Do I regret not having bought great performing stocks on credit? No.
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I admit I feel a little stumped.
Maybe you have examples?
Not questioning you in any way, just struggling with where you are coming from?
I would have always taken a different, better decision with the information available at the time if I had been aware of it? Hence hindsight?
Maybe I just completely misunderstood.
Be well and invest well!
Well not at all!
To illustrate:
Diversifying out of company stock was the right decision with the information available at the time.
Only in hindsight can you say that with that particular company it would have been more profitable to hold.
On the other side, decisions such as starting investing earlier or buying a particular house might have been taken differently with better decision making at the time.
As such, why is everyone not saying how they should have bought Nvidia options on credit 2 years ago and sold at ath? Because yes it would have made them rich in hindsight but with the information available at the time it would have been unreasonable - so as not to say stupid.
Makes sense?
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