I think you hit the nail on the head with 'Show Don't Tell.'

I've found it best to show people the site, my (or local friends) blogs with the post earnings, maybe my wallet...with the BIGGEST piece being able to SHOW that I've been able to spend the earnings. I frequently use @winstonwolfe as an example where he paid most of his monthly mortgage payment with earnings a few months back. But even then, they have to 'trust' that.

A couple things I'd recommend:

1. There are Bitcoin debit cards available that let you just swipe and buy, just like any other debit card. Bitpay is an example of this. Helping people believe that earnings are accessible and spendable make the gears turn a little more for people.

2. I try not to go too in depth on crypto currency itself, but rather try to explain 'Where the money comes from' questions. For this, I just say that there is a daily pool of money created each day that is distributed to authors, curators and commentors. Who get's what from that daily pool is decided by upvotes. (Again, I don't get into the intricacies of the voting structure)

3. In reality people don't really know how the US dollar works either, they just know it's spendable. Most people don't notice the fluctuations the dollar really has since all they see is the bill in front of them, not a market comparison...the closest they see if the effect on their buying power when say gas or food prices jump. While again I don't get to in depth on the crypto side (until they ask follow up questions, which does happen, and is the goal imo), I merely try to get them to be mindful of what they really don't know about their own 'paper money' system, so crypto merely being another unknown isn't seen in a negative light.

4. My biggest argument for potential content creators..it's free! (which probably wont be the case forever, btw) I can hear all the scam talk out there and really not care...I've invested no money, just time...which was spent on things I wanted to do/write anyway. I already have my takeaway...plus earnings from it. Even if everything went belly up tomorrow..I've already won! :D

(I'm hoping to have a non-crypto oriented post on 'What is crypto and why it's not scary' in the next few days that I hope helps with talks like these.) Feel free to holler if you find other 'impediments' people have and need explanations and/or arguments for. I'm trying to collect and/or produce these materials to package together for steemit ambassadors.