Playing the "when do I move to a way more conservative investment because there will be a correction coming" balance is going to be tricky. Sooner or later, that bear market is coming. Question is how hard? And will there be a massive one session crash that will be the start of it? I remember my dad losing close to 40%(almost a half million)of his 401k back in 1990 in that crash. He never really recovered that money as he retired like 4 years later. For that reason I have mostly invested conservatively over the years. I would be hurt by a big crash if it happens but probably not nearly as bad as most.
This, doesn't seem right.
Stock market was at it's all time high in May '90. Bottomed out in Oct '90, and by Feb '91 it was already setting record highs again. Even if your dad held everything in cash his whole life, finally decided to invest at the peak in May '90, he would have been up after 9-10 months. Retiring sometime in '94 or '95, he'd be up 25%-70%, had he only invested everything at the peak and held on till retirement.
Of course this is going off the S&P 500 returns, and assuming he held. Probably more common back then to be less diversified (having everything in only your company's stock, a poorly run fund, or a few blue chips). Also may have sold at the bottom during the recession, and missed out on the gains from the recovery and been too jaded to get back in.
But for anybody far away from retirement, buy and hold, can't time the market, yada, yada, yada.