Perhaps appreciating the beauty in my kids' smiles or holding my wife's hand is good enough.
Yes, it's good enough. It's in the simple things and quiet appreciation of what's around you that teaches you the language of silence.
I just haven't figured out how to do the whole transcendental thing. Maybe I'm overanalyzing it...
I hear you, and yes, overanalyzing it runs counter to what I'm pointing to. That's a common thing, actually, because people are so used to relying on their mind for answers, but what you call the "transcendental" has nothing to do with thoughts. Quite the conundrum, isn't it? I'd like to make a suggestion - there is a very profound book called Already on Holy Ground that may be helpful beyond what you've encountered with The Power of Now.