It's sad to admit but the market has kicked my butt over the last few years. I'm down 30% since 2020 speculating when I should've just been putting the money into index funds. At what point do I cut my losses and start over? (This is purely in regards to the stock market).

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At the very least start harvesting your losses.

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I was going to say something similar… they must have invested in some winners… harvest those bad boys…

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It depends… do you still believe that what you invested in will outperform long term? Did you make calculated risks or did you just throw money at the wall to see what stuck?

If you still believe in your thesis, hold… or maybe even add to the positions you have high conviction in… but you never really ‘lose money’ in the market until you book the loss…

So if it’s easier for you to just book the loss and rotate into an index fund, that’s perfectly fine and a decision that’s personal… but also keep context in mind, you’d be booking a loss to buy into an elevated market that has reached ATHs 7 times in October and has been hanging around at those levels…

So the question you’d need to ask yourself, do you believe that your speculative investments have not participated in the same rally we’ve recently seen in AI? Have they held steady? Would there be increased utility for those investments in a go forward environment? If there was a broader market contraction, do you believe that your current investments will fall in kind, and to the same degree? Do you believe that these investments could be considered ‘value’ and could be rotated into?

All things to consider before just pulling the trigger blindly…

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It sounds like what you've been doing is gambling, not investing. I'd suggest reallocating, but be careful about the timing. There's nothing wrong with selling off bad investments and going to cash and then taking time to get back into index funds or more reliable ETFs. The reason I say that about taking time is because there could be a pullback coming, and you might as well do some dollar cost averaging over the next year or two. If you want to speculate for the love of the game, keep a small portion of your portfolio for that, if you sink it into a cannabis ETF that sinks like the Titanic you'll only lose part of your pile.

I would not beat yourself up about something you couldn't have predicted. If we could accurately predict investing, nobody would ever lose anything. I would just talk to an advisor and see what they recommend based on your specific situation.

Back in 2020, I gave a small portion of my portfolio to speculation investing. I lost 80%, but it wasn’t a huuuuge deal since it was just a couple grand. I recently just cut my losses and sold it to put the hundred dollars remaining in indexes.

I’m not sure how much money you’re working with, but I’d say just accept the losses, sell, and reallocate to indexes over time. Don’t beat yourself up about it either, speculation in the market is such an easy trap to fall into. You make one slightly good investment and then ride that high right into the ground.

If it was speculative and a small part, why not just ride it out? Or put a couple hundred bucks in to halve your cost basis? Just curious, not saying that exiting was right or wrong…

Those are the joys of speculating… high volatility, in exchange for above average expected returns over a 10+ year time horizon…

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Now

Best time to start is now! In the future, I’d give yourself something like 10% of your portfolio to play around with and the rest should be in index funds.

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