I haven't actually set this up yet, but it is the only system I've thought of that I'd be prepared to trust. atm, I'm trusting my longevity and paper chaos that no-one else is likely to find their way through. I've not wanted to write anything clearly for fear a thief would break in and access it (and everything). It's all very much like a will.
-Dormouse
You can also implement a system like this the old-fashioned way: let your attorney handle it for you.
You could instruct your attorney to hold and deliver sealed envelopes to whomever you designated under whatever conditions you wanted. If the information is in an encrypted digital format, you could even give each future recipient the decryption key in advance. They wouldn't be able to use it until they got the disk you prepared for them. And it would only work on their disk.
You might even want to have a little fun with this. Imagine quietly pulling a friend or relative aside at a party. Put on your best Peter Lori expression and, in a hushed voice, say:
If anything should ever happen to me, somebody will get in touch with you. He'll give you an envelope which will explain everything. But no matter what happens...please!...you must remember this code word...
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Using an attorney has some ramifications however.
If you are in the United States, handing your attorny those sealed envelopes would give you the advantage making them
privileged client-attorney communications, which are not subject to disclosure under normal circumstances. This would protect them from virtually any attempts to get access to them.
Unfortunately, if this information would only be released upon your demise, the situation changes significantly. Because all your assets become part of your estate when you die, any post-demise communications or instructions your
executor receives are subject to probate review for possible tax consequences. Uncle Sam doesn't care if you love him and leave him so long as you leave him enough, to paraphrase Mae West.
So you might as well forget about quietly slipping that waitress (who was always so nice to you) the access codes to your secret Cayman Island bank account. You can still leave it to her - but she'll have to pay taxes. And needless to say, anything in your estate that's illegal (like maybe those bank accounts) would be subject to seizure by the courts.
And don't forget that the courts are increasingly ordering people to decrypt data files. There is no longer such a thing as absolute
legal privacy. If your recipient has the key to whatever you sent them, a judge may order them to unlock it for review by a court.
So if you're really trying to hide something of a dubious nature, forget about using an attorney. They're allowed to represent and counsel you in complete privacy. But they're not allowed to help you break the law.