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All the time. I feel like crippling anxiety, insecurity, mental anguish and deep self loathing is par for the course in this career. When it gets to the point where I literally hate myself for being alive, I start to consider dropping everything attached to a circuitboard and cleaning floors for a living instead. This happens about 2-3 times a week.
When it comes to software development and adding features, adapt an investor mindset. Ask yourself what is the return on investment (ROI) of implementing that feature? What are the risks? How can you hedge your bets? etc.
I remember reading a book "software by the numbers" which I think covered that. https://books.google.ca/books?id=tW14FDkNYv4C&dq=software+by...
The last thing you should do though is "push blindly" and not "overthink". Analysis prior to acting is a good thing and the anxiety you feel is because you're uncertain about your the future. You cannot predict the future because you don't have any research.
It doesn't mean you should wait for certainty. Nothing is deterministic. But you should always operate on your best guess; after having done your homework to investigate all known unknowns and minimize risks.