While I don't think the change is really a negative - while spiking in esoteric complexity for a while there, I think video games have become much more accessible in recent years, so much so that I think nearly everyone I know plays some sort of game here and there - I do miss the sort of experience he mentions in the beginning of that column.
I don't think you can perfectly replicate the exact feeling with tabletop games. In fact, it's undesirable. While I think it can be very entertaining in a video game to wander about and try out things in an experimental fashion, doing so in a big group of friends while referencing a rule book constantly would likely just be frustrating and awful. RPG rules, first and foremost, should be clear in mechanics and purpose.
That said, a similar sense of exploration can be had in a pen and paper system. While the rules should be clear, their application should be intuitive enough that they can be applied in situations that could surprise GM and Player. All but the most narrative constrained sessions have a sense of non-linearity to them; a "final boss" can be waylaid by a clever player sabotaging them with an otherwise innocuous ability early on or an insignificant NPC could become vital when an oddball feature of theirs comes into play thanks to some unforeseen catastrophe.
This is what I'm attempting with Break!!, mainly by keeping the rules as "common sense" based as I possibly can while retaining the...er..."integrity" of the game's tone. I want the players to be able to foil the Emperor of Sol because lard isn't technically a weapon, or free a sealed sword from it's stone prison by using an alchemist's solvent to dissolve the rock around it as opposed to actually being the chosen one. The final outcome of a session should be able to be a surprise for everyone.
...Of course, if you want, you should be able to win by proper application of sword, magic or skill as well. Part of the freedom to act out of the box is that you need to be able to act within it, too.
Oh yeah, happy new year and stuff.