One thing I did that really, really didn't work is buying a lot of bond funds. Just buying a lot of individual bonds seemed too complicated, so I did that and apparently bond funds don't behave like bonds and just go down on sentiment... It's my biggest ever loss investing anything so far, and unlike stocks I suspect it won't go up very fast. Painful lesson, I now buy some bonds but only individually - i.e. treasuries or Goldman Sachs/Bank of America bonds on dips. Dunno much about bonds though, so I don't buy much.
Another thing that didn't work out so well although on a much smaller scale are international funds. What's up with international funds, I don't know. Seems like whatever international things they are investing in have been going nowhere for the last 5 years, luckily I only have very little. I wish there was ELI5 somewhere about this.
One of the things that worked surprisingly well in a sideways/down market is selling a cash-covered put ladder on SPY. I try to get $650-850 for a 3mo put, resulting in rather implausible strike prices. Unlike stock puts, where you can automatically catch a falling knife, I am not actually sure what the catch is with SPY, other than if it's the money you might need soon (i.e. you don't want to have to sell when you get assigned). I feel like, in the absolute worst case, you get assigned a lot and SPY tanks for a long time a-la Japan; that would be bad but most other investments you could have conceivably made, including just buying SPY, would do just as bad or worse. If OTOH we say buying SPY low is good, you basically only get assigned at big drops - it's automatic market timing (that also takes care of "oh noes it's going to hell I cannot buy now" mental block - I wish I this going during the COVID drop!). I got assigned once last year, I think around the dip in June, so it's still barely in the red, even after the horror show last month, compared to my buy-and-hold SPY purchases since then. OTOH if you don't get assigned you make 7-10% interest on cash used to cover, effectively (e.g. selling a 3mo SPY 335 put for $650). I also sell implausible 3mo calls on that SPY I got assigned, mostly because I have lots of index funds already via buying and holding so I don't care if it misses a huge market rally.
Another thing that didn't work out so well although on a much smaller scale are international funds. What's up with international funds, I don't know. Seems like whatever international things they are investing in have been going nowhere for the last 5 years, luckily I only have very little. I wish there was ELI5 somewhere about this.
One of the things that worked surprisingly well in a sideways/down market is selling a cash-covered put ladder on SPY. I try to get $650-850 for a 3mo put, resulting in rather implausible strike prices. Unlike stock puts, where you can automatically catch a falling knife, I am not actually sure what the catch is with SPY, other than if it's the money you might need soon (i.e. you don't want to have to sell when you get assigned). I feel like, in the absolute worst case, you get assigned a lot and SPY tanks for a long time a-la Japan; that would be bad but most other investments you could have conceivably made, including just buying SPY, would do just as bad or worse. If OTOH we say buying SPY low is good, you basically only get assigned at big drops - it's automatic market timing (that also takes care of "oh noes it's going to hell I cannot buy now" mental block - I wish I this going during the COVID drop!). I got assigned once last year, I think around the dip in June, so it's still barely in the red, even after the horror show last month, compared to my buy-and-hold SPY purchases since then. OTOH if you don't get assigned you make 7-10% interest on cash used to cover, effectively (e.g. selling a 3mo SPY 335 put for $650). I also sell implausible 3mo calls on that SPY I got assigned, mostly because I have lots of index funds already via buying and holding so I don't care if it misses a huge market rally.