"...asking "why?" isn't negative, but rather a necessary question to gain more clarity and achieve better results."

Be a Skeptical Optimist by Randy Gage: "You need skepticism, because that’s the critical thinker part of it all. You must question premises and not follow the herd blindly. When people tell you that something can’t be done, you don’t accept that at face value. When people tell you that you “should” be doing something, you’ll weigh the input rationally and ponder questions like these: Is the premise correct? Do they have a conflicting agenda here? Do they have my best interests at heart? Are they unknowingly following a mind virus that isn’t in my highest good? Are they qualified to give me that advice? But you also need the optimist part. You have to go into things expecting them to work out. Nine times out of ten, the team that expects to win does. And when they both expect to win, the team that believes it more usually does. Skepticism is good, because it keeps your mind open. But never fall prey to cynicism, because that closes your mind again. To be successful, you need a default setting of optimism. And this is a good strategy, because the evidence supports it."

The Counterintuitive Trait That Will Make You Significantly More Successful | Shane Snow | LinkedIn: "...the most counter-intuitive quadrant is the one where the most breakthrough success can be found: Optimistic, but Skeptical. This is where the innovators reside, where inventors who dare to doubt the status quo ask the questions that need to be asked in order for the world to change. They need a healthy amount of optimism to believe that the world can change for the better, and that drives them to make transformative things happen...

Harriet Tubman, one of my favorite historical characters, was clearly an optimist when she had many reasons not to be. She was born a slave, lived a hard life, suffered a head injury that caused her seizures; her husband remarried another woman and declined to flee north with her. And yet, after she escaped from her captors, Tubman ventured back into slave territory to rescue people. She clearly had faith in a better future for her and them, and that's what people remember. But Tubman wasn't credulous. She was extremely careful, carried a pistol with her (and had occasion to pull it out). She was wary of circumstances and people's loyalty and intentions until proven otherwise—and that allowed her to rescue dozens of people from slavery and inspire millions more. The skeptical optimist believes things can be better, but doubts conventional wisdom. Sure, madmen also fall under this definition. But as I've written before, crazy is one of genius's main ingredients."

Think Splendid®: On Being A Skeptical Optimist: "An optimist is not the opposite of a skeptic, it is the opposite of a cynic. Cynical people operate with a doom and gloom energy, an outlook that shuts down ideas before they can even start. Skeptics are critical thinkers. They look beyond the surface and dig deeper.  Skeptical optimists believe that there's always a light at the end of the tunnel and that people can change and have the capacity to do good far beyond what we could ever imagine. They're also aware that asking "why?" isn't negative, but rather a necessary question to gain more clarity and achieve better results."

Is An Optimistic Skeptic an Oxymoron? | theyellowkite: "If I had to identify myself based on my primary outlook, I am definitely an optimist. I’m a glass half full, it will all work out, can-do kind of woman. However, I question everything I hear. Some would say that is good, it means I’m curious. I am curious! But, I’m also a skeptic, especially when it comes to the news and to gossip. I used to simply filter what I wanted to hear, checked out facts on items that piqued my interest, and let unsubstantiated gossip fall on deaf ears. However, lately I find myself becoming annoyed with people who take everything they see, hear or read at face value. When did we become a nation of spoon-fed, short-sighted, LAZY people? Yes, lazy."