What are the calculated risk you have taken in your life and how has it helped you?

I am going through a dilemma where I got to choose a different job or masters abroad. Different job is a shody quick fix but masters is something i always wanted to do.

The risk with masters is high coz the loan I have to take and too many unknowns. I want someone to say 'it will be alright' but don't got many to say that. They keep scaring me saying that I will be jobless and with lot of loan. That I don't deserve any better etc etc. As a overthinker this is horrible since I think of all the possibilities of how I will fail (working on it)

So here I am asking reddit folks.

Thanks for any comments coz my replies don't go through.

Adding more details; 1. Want to do Masters in CS in US. Reason is job opportunities and more money 2. Job now is working as Software developer in a startup where there is no growth for me.

Edit: thanks mcfuckityfuck94