I sincerely appreciate what Jack Bogle teaches. It is extremely helpful to consider his writings and interviews. It can be difficult to just do nothing. If one has the good fortune to experience a mid-life windfall, should they just dive right in from day 1 or spread investments over time, investment categories, etc.? At the present time, prices of every investment option just seem too high, yet our currency is being devalued by Federal Reserve action, so doing nothing seems risky. Just as indexing avoids paying too high a price for playing the game, it seems worth considering whether one is paying too high a price when getting into the market. That was my experience from investments in the period around the year 2000 where I believe market prices were simply too high to leave room to make a profit. Is there a difference between worrying about pricing vs. timing? The only mitigation I can come up with is to diversify over investment categories and spread purchases over time.