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Asset prices don't always go up. The downturns have lasted much longer than 5 years. So if you want relative certainty you'll have $X at a certain date then you need to be in cash years beforehand. Otherwise you're gambling or have a backup source of cash.

Yes, 5 years. http://nerdwallet.com/article/investing/where-to-put-short-t...

If you're young and you've only seen the market go up you need to familiarize yourself with normal volatility patterns. The market can easily take a dump at any time and fail to provide a positive return for years.

> The market can easily take a dump at any time and fail to provide a positive return for years.

...or decades: "Nikkei index hits 30,000 for first time in three decades"

https://asia.nikkei.com/Business/Markets/Nikkei-index-hits-3...

Do you remember the lost decade? 2000-2009-ish... the markets went no where for almost 10 years.