If you don’t have moments in your life that make you go “Man! That was stupid!”, you’ll never have ones that make you go “Wow! That worked out”
Be it scientists trying to unravel the mysteries of the universe or a person trying to discover their own personality, you don’t find anything new unless you do little experiments.
For it is mostly in hindsight that one can fully say if something was crazy or brilliant, till then you don’t know and neither does anyone else.
Whether it is your startup, your life or your job, looking back at what other people did (or are doing) can only inform you broadly; data, reports, trends, books and the like aren’t going to walk up to you and say “Go ahead, it’s the right time to quit your job!” or
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Just do it .. in little steps