@RegalChicken , the current uncertainty with the Market, prices etc also has me thinking more about this the last few weeks. I think it may have been yourself (could be wrong) had, or talked about a Spreadsheet they kept a few months ago with percentage sells\prices etc. I too used one that lets me see what sort of money I could take out at certain price ponts with percentages of XRP held, and it definitely is nice to dream and see it with different Prices.
I'm not thinking so much of Retirement, but more completely Debt free (with some left over of course). A life with no Mortgage, Kids University, Car, Credit Card payments etc. sounds really tempting, and as I am not Retirement age just yet think would leave me feeling pretty well off and secure. Maybe that, and enough for a year or so in the Bank to enable training to do something different would also suit.
As you mentioned, sell at 10 knowing that is not as high as it will go. It's these 'what if's' that are the thing (well, for me anyway). E.g. If you're feeling pretty damn well off and pleased with yourself when the price is at 10. You decide not to sell, hoping for 20. Go to bed one night and it's at 15. Something catastrophic happens or comes to light while you're sleeping and when you get up it's at 3 ! The reverse is also true, and you sold early. You'd probably spend quite a while kicking yourself lol.
I think it is a good idea to have a "plan". Doesn't have to be set in stone though. Momentum of the Market and more importantly Ripple\XRP will be the deciding factor for me when I decide to sell the lions share of mine, but I am starting to weigh up strategies for selling at certain prices in order to pay for different things. If Ripple continue to do as they are and XRP begins to get utilised as we hope, I will never sell 100% and will keep a percentage. It may not be a large percentage but if XRP gets to the dizzying heights as some people hope, it will only take a few hundred in 15 years time to be worth a pretty substantial amount of money.
At the end of the day, we bought XRP to make money down the line but also need to be realistic. Honestly, I have no idea how high the price can go and in what time frame. This last 6 weeks though have shown again how unpredictable it is. The May\June\July scenario bothered me a lot more than this one. Although then, it was the first time experiencing it, resulted in me losing quite a few XRP trying to time things and play the market. Needless to say, this time I just watched ! A few cent swing back then against a few Dollar swing now lol. Anyone getting caught up this time, won't be bothered with the next one !