I see this conversation a lot, and have increasingly been asked it ..this is the way I think about it:
Over the 15y price history of Bitcoin, 4 years after buying on any day has resulted in a minimum fiat price increase of 113%. Now, if that continued forward, the rough rule of thumb is that your worst case scenario is the fiat value of your bitcoin doubles every 4 years.
That's the framework I then use to start thinking about spending some bitcoin.
So for me, what it comes back to is not "how much of my stack" should I spend (or not), but what is worth spending some bitcoin on to make my life, or the lives of those close to me, better. A home for your family, long sought travel, comfort for aging parents .. to my mind those are some of the things worth spending bitcoin on.
Following that through, by patiently hodling, bitcoin will enable many to ditch current jobs and focus on helping Bitcoin flourish .. whether that's your local meetup, helping at conferences, learning new technical skills, contributing to bitcoin-aligned open source projects, or bringing new products or services to market that are currently missing.
It comes back to that simple question of: Well, I could do it now but if I wait another cycle it will be half the bitcoin or less to do that thing.. ..except for time. Time is the actual finite resource, so no-one can wait forever, and dying miserable and alone with a phat stack is not "winning".
Bitcoin offers options. <3
I NEVER SELL my BTC for fiat. I only USE my BTC to buy things. NEVER EVER FUCKING GO BACK TO FIAT!
Bitcoin is NOT for the weak! Only for brave! https://www.youtube.com/watch?v=vMU804-bjQA
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Use your money! Make sure you earn/buy more then you spend and you'll gonna be fine. If we not use our bitcoin, whats the cause?
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The question is NOT "When" but "why not now" ?! FOR FUCK SAKE USE YOUR BTC AS MONEY! It is the ONLY way to FUCK THE GOVS AND BANKS!
When people will fucking understand this?
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Don't take advice from the maxi's that think Bitcoin will be bigger than gold and the people that tell you it will be implemented globally just like using a debit or credit card. They will lose you a lot of money. I'm not telling you when to sell or when not to, I'm just saying don't take their advice because they will tell you to never spend no matter what and that's really shitty advice.
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