Not a dumb question at all. We all struggle with this until someone shows us how to do it.
All good advice given so far. To reiterate what's already been said - the most important thing is that you shouldn't aim to be "lifting" the bike, I've hurt myself trying to do that on various bikes before I worked that out - the key is to roll the bike and use its momentum to get it onto the stand whilst anchoring the stand with your foot - it's a bit of a dance but you get the hang of it.
I've got better at it, but I still don't enjoy putting the bike on the centre stand. I understand your fear of dropping it. With the sidestand down it's not doing to fall that side - if you do it with a wall on the other side and something to protect the bar end on that side whilst you're practicing, it's not going to fall far that side and damage anything if you do drop it.
Lots of how to videos on YouTube of not particularly big or strong people putting bigger bikes that these on centre stands.
