Good luck friend. Having a trip sitter isn't a bad idea for the obvious reasons, but I would actually recommend taking a low dose (~2 grams) alone, especially if you're prone to social anxiety. If you're feeling good about it, take another gram or two an hour or so into the trip.

The best trip of my life, and the one that had the most drastic impact on my mental health, was when I tripped alone at night. I felt the love of the universe pointed directly at me. I wept tears of joy at the enormity of it all. It was like the universe was playfully joking with me, all up in my face like, "Cmon son, you really wanna leave all this?" But also at the same time saying, "I understand if you want to leave, and I'll still love you if you do."

Complete paradigm shift. I wouldn't say the depression was cured, but it was somehow diminished and made manageable. It was like it was forced into a little corner of my brain, where I could observe it. Whereas before, it made up the entirety of my brain. Also a plus, I didn't feel the need/want to trip or do any type of mind altering substance for quite some time after. I was still able to feel the love, albeit on a more subdued level. I felt like I was given a new face. I know that sounds weird, but that's how I felt.

If you find yourself wanting answers, or just wanting to flesh out ideas, just write it down. Stream of consciousness writing always gives me peace.

But anyway, regardless of what you choose to do, I wish the best for you. I hope you can stay strong, and I hope these crazy little things can help lead you to the place you want to be. I know it's hard to believe, but you play a bigger part in this than you know.