The option I have difficulty preparing for is the selling part. Holding is easy.
Risto's "SSS" strategy for dealing with bitcoin is IMHO the best approach to dealing with this.
I keep this solidly in mind for my BITCOIN holdings, but unfortunately not yet having achieved even the first double-in-value on my bitcoin, I can't yet put it into practice. Maybe, some day... soon? One can hope... LOL
And actually, however, I have not even personally yet taken this strategy with my MONERO stash... just because it's still small enough (sadly) that I've felt a little more like "gambling" with the first few doublings in value. (I have taken just the small dollar-value equivalent of my starting buy-in off the table, so 100% is now "house money" for FREE, which removes a TON of the worry about *if* XMR might totally crash to zero? Easy come, easy go LOL).
Honestly I was CLOSE to taking the first "SSS" selling step, liquidating the first 10% chunk, way back - about a month ago (LOL) - when we were hitting $15... if it'd gotten to $20 I would've done it for sure, LOL but unfortunately I hesitated (probably just due to pure greed LOL) and now here we are back dancing with "only" $5 or $6 price point.
So... oh, well. Live and learn, and now just gonna HODL again 'till we get back to $15. Or $20. Or maybe $50-$100
P.S. {Edit} Should've included a link to the "SSS Plan" thread... Risto's "Sane And Simple Savings Plan"

Here it is:
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https://bitcointalk.org/index.php?topic=345065.0;all