If you where to fail, would any of these people saying you're successful help you succeed?
Yes, you have a safety net and support net.
No, there opinions are meaningless gestures, just being cordial.
YOU are the only one in control of your life and you have to set a long term goal ... you sound really goal focused and thus far you've only had short term goals. The short stuff is only going to give a short sense of personal accomplishment. To keep you busy for a while you need something long term to work to.
And yes you do need a few failures to humble you and bring you back into reality. You do have one so far, quitting med school.
It could also be that the things you have become good at where chosen because you knew you could do well. Maybe pick something you do poor at and challenge yourself more.
And speaking from the poor, never take a job/career that you can't leave at work. There needs to be a clear separation of work and personal life. If you're bringing work home, you're not really home.
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