Welcome to the nexus. It's probably the best place on the whole internet to ask these questions. You're in the right place  But on the other hand no one can tell you what to do. At the end it's up to you.

I always tell people to start with mushrooms before they go for a full DMT blast. Maybe it's because I had a lot of experience with shrooms before I did DMT and I would not have wanted to DMT as a first psychedelic.

I don't find DMT a good thing to work with. Shrooms are more of a medicine for me. But I've yet to try DMT in Ayahuasca.

But I think you should ask yourself one question: Do you want to be yourself or are you going to try to always be someone that fits into your family or what ever group you're in at any given moment.

I'd do the psychedelics in your steps. I have a very positive experience with psychedelics. I've had some extremely difficult trips in my life but they can be very beneficial. I've felt very disconnected after some trips but it can just take some time to ground yourself after a trip. There are tricks for that. Like physical exercise and sweat. Sweating is my way of grounding myself. It can take time but it's worth it.

So my advice would be to go for it but start with a low/medium dose of shrooms.

Good luck