Welcome Mitchell! Sounds like you are doing very well. Buy and hold works as long as stocks remain near all-time highs, but the closer you get to retirement, the more you are at the mercy of the market, which we have seen, can be volatile. The 40% haircut that the S&P 500 took in 2008-2009 is manageable when we're young since there is time to recover, but it can be very difficult when we're older since we may not want to be taking as much risk.
Timing the market is not easy. Making big bucks is not always possible. But the key as we get older is to avoid the big losses when possible and "taking shots" when opportunities present themselves, and that can only be done by playing the timing game. There are a lot of different approaches to do that and that's something you may be looking to figure out going forward.
Good luck!
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