First of all, can I quote myself here? From the intro page of my poet website (see below for link):

"Life is full of people with great ideas, who sit on their butts and do nothing. Then they die."

Which brings me to answer your question about the gutsiest thing I've done --

BECOME THE POET LAUREATE.
Which involved pitching (and doing mega reasearch for) an idea which largely produced the reaction: "Huh??"

Which involved pitching this idea to a City Council which had no idea what a Poet Laureate was or did, and a Library which not only had never done anything remotely like this, but had absolutely no money to do it (and for that matter, NO library in the United States had ever independently appointed its own Poet Laureate)

and presenting this to umpteen committees with umpteen+ questions, when I'd never spoken in front of a committee before

in a conservative suburban town not known for innovation

in a conservative Orange County which was not known for promoting poetry, and which had never had a poet laureate AT ALL. For that matter, neither has neighboring Los Angeles or San Diego. (Tujunga, 60+ miles NW of here and part of LA County, does. But none in LA proper)

even though I had been barely published

even though the prevailing "poetry cliques" of Orange County were either indifferent or outwardly hostile to my efforts (and many still are)

even though my closest friends including other poets were highly doubtful that I could pull this off, and told me "Don't get your hopes up"

I knew I could do this.

And I knew I'd never forgive myself if I didn't try.

And I did it.