I know one implies the thing I'm comparing actually _is_ the thing I'm
comparing it to, and the other doesn't.

Can someone suggest an easy example or trick for remembering which is which?
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particles particle-に particle-と
～にしては vs. ～としては
～にしては means "Considering X is Y, ..."

> トムはお金持ちにしては、あまりぜいたくな人生をおくらない (Considering Tom is pretty rich, he doesn't
> lead a very luxurious lifestyle

～としては mean "As a / In the capacity of X, ..."

> 弁護士であるわたしとしては、それを勧めるわけにはいかない (As a lawyer, I cannot recommend (doing) that)

~~So the latter is when the thing actually _is_ the thing you're comparing
to.~~
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Just adding to an existing answer because I typically don't think of these two
as comparisons, I look at it from a different angle than the OP.

I typically think of this as more of expectation rather than comparison for
～にしては, although comparison could be valid as well but I never think of it like
that.

So as @istrasci pointed out, ～にしては means "Considering X is Y...". There is an
expectation involved because it typically goes against what the speaker is
expecting from X.

From @istrasci's example, we have

> トムはお金持ちにしては、あまりぜいたくな人生をおくらない(Considering Tom is pretty rich, he doesn't lead
> a very luxurious lifestyle)

Normally we usually expect rich people to lead a luxurious life, but in this
case, Tom does not lead a luxurious life, therefore it goes against an
expectation. So it is used to contrast a reality (does not live a luxurious
life style) to some kind of expectation (rich people typically live in
luxurious life style)

Another example:

> スキーは初めてだと聞いていたが、それにしては、なかなかうまく滑るじゃないか。(I heard this is (your) first time
> skiing, considering this is (your) first time, you were pretty good)

This is another example of contrast between reality (you were a first time
skier and you were pretty good), to an expectation (first time skiers are not
good)

For me ～として implies and empathize some kind of position.

> 弁護士であるわたしとしては、それを勧めるわけにはいかない (As a lawyer, I cannot recommend (doing) that)

Lawyer is a position being empathized here.

> 学生として参加する (Apply/join as a student)

Student is a position being empathized here, I don't just want to apply, I
want empathize that I want to apply as a Student.
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