I'm not a handyman, but I am a man who happens to be handy.

I have done quite a bit of painting and caulking for a guy who's not in the profession. I despise both with a passion, though, especially caulking, and I have never once been satisfied with a single paint or caulk job I've done. I feel like I'm the embodiment of "be bad at this for a long time," although I'm objectively probably halfway decent at it.

That is to say I think Ira Glass' quote of "You've just gotta fight your way through" to get where you want to be seems especially meaningful in the context of something like painting, where most everyone _can_ do it (or writing / storytelling in Ira's case), but very few are actually good at it.

You need a silicone caulking tool, and a video. I have spent many years caulking like a fool listening to other fools who spray water and use their thumbs. Don't. Use the tool. Use the kind with a little oval tip usually (I mean, there are exceptions with harder caulks but for softer e.g bathroom caulks this is more superior.)

There's one UK guy on YouTube that convinced me of the evils of water/iso sprays and the beauty of the proper silicone caulking tool.

The little wedge shaped caulking tools btw are not enough, as you need some stick to it so you can get around certain angles/items.