How does one train themself to be ok losing their bitcoin stack?

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Pretty sure the Dalai Lama can help.

By having faith/trust in yourself.

Yes, and we do end up losing everything so one must not be afraid.

Feel comfortable that you have done everything you can to minimise the risk. Split across multiple wallets, secure backups of seed phrases etc. And understand that at one point you started from nothing so you already know what needs to be done to build it up again in the worst case scenario.