It's obvious from the question that it is a reflection on my current predicament. I'm at a place where the company is doing okay, but not great. Part of me wants to move on, but the other part - fuelled by legendary startup stories where things took off or turned around at the last minute - wants to keep going till it's officially dead. Before posting my question, I was debating whether asking the question itself served as a signal for my company's demise, but I am glad that didn't stop me. I feel like the point where I am too afraid to even consider the possibility - perhaps because then I truly know the answer - would be worse than just seeking more knowledge/wisdom.
It's very useful to have a community where I can learn from very experienced people such as yourself and use that information to augment my knowledge.
Thanks again for your thoughts.