Some very interesting points made here so far. I wasn't expecting much of a response to be honest but I'm glad to be wrong. I do agree that at this stage, encouragement generally needs to be directed at businesses. I would say that supermarkets might be a great place to start with that, considering what franky1 said.
In terms of explaining it to people, I have a few ideas on that. One of them is to give people paper wallets with $5-$20 worth on them. Then sit with them and walk them through several processes like making a purchase with bitcoin and how to transfer btc between accounts. Also explaining to them how everything works as they themselves are actually doing it. People like to have their hand held through new experiences. This method also takes away the risk people would see with using their own money, at least to start with.
Another way to educate people is to sit down with them and walk them through ways of acquiring bitcoin. Starting with faucets, which may be obvious to many, but most likely not newcomers. Then move on to other possibilities such as local trading (with advice on security of course) or buying through sites. I have a few in mind but don't want to name them for multiple reasons.
My idea of pitching it big is basically the fact that I, or someone else, would personally sit down with a person and take them through the various processes. The hands-on aspect is what makes it work.
As a side note, I, or someone else, could also walk them through how to tip with bitcoin. A learning experience that benefits both parties. Not a necessary part, but a possibility.
just giving someone $5-$10.. thats too much. make it $1 so they can buy a pepsi at the 7eleven (once you sort out retailer adoption first). also think about how you can make it easy for noobs to start using bitcoin without hand holding them for an hour, step by step..
after all 99% of apple users dont need hand holding to set up applepay
as for showing people how to earn it.. forget faucets.. thats like 5% of minimum wage.. plus telling the world about faucet giveaways actually ruins the perception of bitcoin.
imagine it.. you want to advertise dollars to europeans.. so you throw out a few american pennies on the roadside you see someone pick one up and then you tell them every 10 minutes you will throw another penny down, hoping they come back.. most will just walk on by others will pick it up, but not suddenly want to buy $400, or hang around 24/7 to make $1 mainly because they cant use the $ bank notes in european supermarkets, so its not worth their time.
instead look at all the businesses using bitcoin, everything from coinbase to overstock, etc.. look into the jobs those places are offering and get people real jobs earning bitcoin. along with helping new businesses accept bitcoin
otherwise you are just spending an hour of your own time handing out $10, to someone that will ultimately feel its like facebook credits that can be used on limited things.