Bear markets are usually good times to buy stocks because they are beaten up and bargain priced. Of course, the exact bottom can’t be timed. It may be next month or next year before a new bull market starts. So if you do buy when stocks are in a bear market, you need a lot of patience and fortitude to watch your purchases slide for a while. If you are lucky, it’s just a short wait. More likely, it’s a long wait and this is where the market will test you: your stocks tumble more, then rally some, dive again, and suddenly shoot up only to crater before the sustained turnaround kicks in.
Or, you can buy in stages at regular intervals, to average in your position over time. But that requires patience and fortitude too because it’s hard to keep up regular purchases with your emotions getting yanked around by all the plunges and rallies. Sometimes it will feel like throwing money into a meat grinder. But it could be easier than buying a big whack all at once and watching much bigger loses accumulate on the downturns.