It’s fairly easy to be skeptical of something - in fact, like entropy, it’s kind of the default state. Entropy happens because there are more disordered states than ordered ones. Skepticism happens because there are more ways something could fail than ways it could succeed (usually). So it’s easy to find a story to be skeptical, if you want to.
But it’s not enough to just be skeptical and contrarian. If you’re an investor, you have to be contrarian and right. If you’re an entrepreneur or engineer, you don’t get a lot of credit for just saying “no” - you also have to find a solution you’re not skeptical of, and then build something useful eventually.
So it’s good to challenge our own skepticism. We can ask questions like “how could this work?”, or we can examine the problems we see and ask about potential solutions to them. When looking at new products, it’s often illustrative to look at user value, and ask “what if it works"?” rather than “why won’t it?”.
And it’s good to examine your own biases. I’ve been doing this a lot personally with crypto. I’m pretty inherently skeptical about a lot of that field, but I also recognize that my younger self would happily be playing with all the tools and looking for interesting things, so I’ve been trying to keep myself in that mindset. When I look at solutions in this space that have problems (most of them do), I try to ask “can that problem be solved? If it is solved, does this do something useful for a user that hasn’t been done before?” Mostly of the time I’m still skeptical, but some of that exploration has led me to find things that are at least more interesting to ponder further, and more than a few related ideas that are probably worth doing.
Skepticism is a very useful tool, both in life and in engineering. But it also has the potential to get in our way and to create bias in our thinking if we aren’t careful about using it. It should be one tool of many, not the only way we approach challenging ideas.