We can't allow fear to stall us, we can't allow obstacles to hold us.
In my team, during big hype around the product development we did, there were times that I had to take decisions on which path to go, where no one went there before. That's startup life all the time, because if some went there before, most probably you are not that unique :)
As product manager, I think you will encounter it all the time - which feature is more important? to kill or not to kill the module? will it work? pivot? - many aspects to it and this is just small example.
Risk assessment can be managed in a very analytical way from one hand, but actually it is far beyond that, it is more of a philosophical question, and your approach.
You need to come into the understanding of the risk taking spectrum, from 'you snooze you lose' to hesitate endlessly.
Strategic risk taking is when you should look on things from a very rational position, rather than being driven by emotions (==the fear of rainy day scenario being happen).
My advise to you is:
1. Look on the challenge and break it into pieces
It is easier to manage and get decisions on smaller chunks. Also when you iterate, overtime, you probably will get wiser, collect more data, have more feedback, and be able to get to the next decision point about risk taking on that subject with much more facts.
2. PONR
Point of No Return.
Try to look what is the PONR on the path you are going. Most probably it is not the first step. So you should progress, and "buy time" - which means, get more information so that when you will get to the PONR, you will be able to get wiser decision.
3. Voices
We are stuck sometimes in an echo-chamber. We consult with people that share the same background (either from same team, share same manager or any other aspect). We are missing different view to the same issue. It is very important!
Take wise decisions, but remember - who dares wins. Happy to assist!
Dror