Skimming over these comments, I didn't see any answer that seemed like it would be helpful.
As someone who dropped out of college (gave up a full-ride) to startup a business (without a plan, customers, or much code) and 4 months runway in my bank account this is what I did:
-anchor myself to something much more extreme than my daily fears. My daily fears were running out of money and building a product that everyone would laugh at. So I would write down in my journal each day something even more extreme: "I am willing to die broke, alone, and hated in pursuit of {{YOUR_GOAL}}".
-Reframe the concept of risk via death, via sort of nihilistic perspective (e.g. in the grand scheme of the universe what you are doing whether you succeed or fail really won't matter). I would tell myself "There is no risk. One day I'll be dead". I think about death a lot and every time I see someone famous in the news I write their name down in a list as a reminder that we are all ticking time bombs.
-anchor myself to fearless people and ideas. Books I read: 50th Law by Robert Green, Moral Courage by Rushworth Kidder. People I like thinking about: MLK JR, Ghandi
-Be skeptical of your skepticism. doubt is in proportion to # of and magnitude of questions you ask about something. Become brutally skeptical of the safe thing you know deep down you should avoid. Will doing X really make me happy? Is X really the right thing to do? Perhaps everyone doing X is crazy. Would {{INSERT ROLE MODEL}} do X? Why does everyone actually do X? For more on this see Awaken The Giant Within by Anthony Robbins
-Brainwash yourself via repetition. Cf. the familiarity bias. Your brain mistakes familiarity and ease of retrieval for truth. This is how cults make people feel that something is true by simply saying it 1000 times. Develop extreme faith and confidence in yourself by pure repetition. One tip is writing down a goal or affirmation 15 times a day. "I am a very attractive person" or "I am the most attractive person in my city. Everyone". Remember your brain perceives ease of retrieval as truth, and repetition improves ease of retrieval. Maybe combine this with some extreme-anchoring: "I could be the ugliest person in the world, and I could still win this opportunity through charm and persuasion". Or turn it into a positive: "This person WANTS to interact with me because they'll feel so attractive being around me".
- Anchor to other people who had the same issue that you think you do. Abe Lincoln considered himself to be ugly (and so did many other people in his time) (and he had a high pitched voice too) and he still went on to be president, and not only president, but one of the best presidents ever.
-Burn any bridges. When your back is against a corner, evolutionary instinct will kick in and give you a natural fire. For me this was dropping out of college.
-Ensure that the 5 people closest to you are risk takers and confident.
-Have a super intense goal that pretty much everyone in the world would think is impossible. "I will be the richest person in the world". "I will fix {{INDUSTRY_NAME}} by 2030". etc.
> "I feel people judge me more often than not"
IMO when you think about death alot and have a burning passion for your goal thoughts like these never even cross your mind.
For what it's worth I used to be very risk averse too. Would jump through any and all hoops society/school would set. Only invested in Total Market ETFs. Didn't want to start a company until I had 1.3m in the bank and was age 31 etc. Becoming courage was a very deliberate and continuous process I had to (and still) go through.