Good article from yachting World about briefing the main sail with only two people. The most important advice in here in my opinion is to practice and know exactly what each person is going to do before you start doing it.
But I think there are two things left out of this article that are even more important. The first is the axiomatic “Reef early and often.” Maybe they left that out because they’re talking about racing instead of cruising. But if you want to be safe when cruising, you always want to Reef before you need to because by the time you need to it’s going to be really hard to do it.
And the second thing I would add is that this is all a really good reason to have a furling main sale. I know all of the arguments against them. They can bind up. They cannot have battens so you’re main sail shape is never as good as it should be.
But, particularly if you sail single-handed like I do, your number one concern should be not getting hurt and not falling overboard. And that means when the wind is heavy which will be if you are reefing, you don’t want to leave the cockpit. Yes, theoretically there are ways to set up reefs that can all be done from the cockpit, but I have never seen anyone actually accomplish a reef without leaving the cockpit for some reason or other. My in-mast furling may not be ideal but it keeps me in the cockpit when I need to Reef and that is the safest option.
Read the article anyway, it’s worthwhile
https://www.yachtingworld.com/5-tips/5-expert-tips-shorthanded-mainsail-reefing-150527