But feels odd not to consider this all time high.
I was starting to think we were going to get through October without this assertion. Is it at an all time high? I haven't been looking at the stock market this month due to a personal challenge, but I'll make an exception for updating my list. Uhhhh, we're definitely not at the all-time high (which was 3025.86 on July 26). Stock market needs to go up another 1.33% for that. And even then that would only be a 5.3% increase over January 2018.
Going to emphasize the bold part and expand a little more. If you look at the major domestic indices:
S&P: Only up slightly since January 2018, nearly flat since August 2018
DJIA: Essentially flat since January 2018
NASDAQ: Flat since August 2018
Relatively speaking, stocks are probably "cheaper" now than they were 14-21 months ago when considering metrics such as P/E ratios, cash returned to shareholders(dividend payout on VTI), and the fact that stock prices were flat while the domestic economy grew during that time period. That's not to say that stocks are currently "cheap" by historical standards, but it's not like the alternative options are particularly cheap either.
That's not to say that a recession/market downturn won't happen - it's just that, statistically speaking, letting your money sit(high probability of incremental losses over time) will probably hurt you more than investing it right now(smaller probability of larger loss).
Still, investing success can be as much a behavioral game as a mathematical one. If one is anxious about risk, getting into the market gradually is still better than not getting in at all.