Hey Lil,
Great question and I'm so glad you wrote it as a thread!
My personal view is that different things work for different people and that we are all built to think in somewhat unique ways. God put it in Solomon's heart to build a massive temple, the likes of which no one in the world had ever seen, or probably even thought about. And yet, our same God put it in the heart of a widow to share a little oil and flour every day with a prophet before she made a meal for herself and her son.
I used to have huge dreams. I wanted a doctorate in psychology. I wanted to interview Charles Manson. And I wanted to be able to make sure people who committed the most extreme violent crimes weren't given lesser sentences if they wrongfully claimed to be "insane".
I also wanted to be married around age 20 and have 4 kids by 25... 30 at the latest. I also wanted to travel the world and fill up my entire passport with places I'd been. I definitely used to dream big. But life gave me a few speed bumps along the way.
So instead, I've learned to be extremely grateful for a much simpler life. I've discovered that I work much better as a helper than as the primary leader (every Moses needs a Joshua!) And, God did bless me with a few travels I am so thankful for. I may not be able to make every trip I dream of but through the magic of YouTube, I'm able to see so many things I otherwise couldn't (the Pyramids of Egypt, Neuschwanstein castle, the Taj Mahal, some of the works of Frank Lloyd Wright...) and I am content with that for now. But God willing, I hope to see many more things for myself someday.
I do think the "Go Big" mentality is responsible for a lot of innovative success stories. However, it must also be kept in mind that the bigger the dream, the higher the cost (as Zero pointed out.)
I'm definitely NOT saying this is Willie's situation at all, but I've seen many people who have been immensely successful... and I can't think of a single one that didn't have to sacrifice vital amounts of family life in order to achieve it. They missed their child's birth, or first steps, or first words. They were never able to go to ball games, recitals, or important events in their children's lives because of work.
Of course, there can be big payoffs later on. Maybe enough money was made to pay for cars and college and trips. I think most people who go this route know they're missing out on seeing their children grow up but figure the money, provisions, and success will make up for it later.
However... I know many people who feel bitter, disconnected, and forgotten because someone important in their life was "going big" after a dream, and, in they believe their parents, etc. left the most important people (and priorities) behind.