I came across this interesting question on a personal finance forum and couldn't resist formulating my thoughts on this issue. Would be interested to read about your personalised crypto exit strategy too. 

Financial literacy 101 recommends that we assign a purpose to every dollar so that we can rest assured that our hard-earned money is working hard on our behalf. I reckon this applies to cryptocurrency too. So in the first place, I am clear about why I am HODL-ing my Bitcoin and Ethereum for and what I am going to use these digital assets for should I choose to cash them out.  

Specifically, I have decided to make Voluntary Housing Refund contributions for my Central Provident Fund (CPF) account. CPF is a nationwide annuity scheme in Singapore. It is a bit similar to the 401k scheme advocated in America, except that Singaporeans may choose to pay off their housing mortgage with their CPF funds. But because these CPF funds are meant for my retirement purpose, I try to make Voluntary Housing Refund contributions as often as I can so that I don't drain off those funds that are meant for my old age. Anyway, I think making VHR contributions yields me utility and sparks joy because the profits I accure from BTC and ETH are considered "happy money" in my mental accounting of my finances. So what better way to use such "bonuses" on something that I would feel pained to do with my salary?  

As to when I HODL and when I cash out, I have this idiosyncratic strategy that I employ for my Gemini portfolio. Sometimes, I am lucky enough to attain $10 worth of BTC as referral credit because my friends make use of my referral link. I will alternate between transferring $10 to the Gemini Earn program and cashing it out. So far, I have five referees, so for the 6th referee, I will boldly cash out this $10 worth of BTC. And yes, no regrets because this $10 will go straight towards paying for my Voluntary Housing Refund.  

So this is my highly personalised crypto exit strategy. What's yours?