That's what the actor asked himself before signing on to star in Dallas Buyers Club, a role that would require him to lose 47 lbs. – and, ultimately, gain a Best Actor trophy.
But it's also the approach McConaughey applies to much of his life, including his first-ever Oscar nomination.
"I'm having a ball right now," says the 44-year-old star, who delivered an exuberant, emotional acceptance speech that touched on everything from his late father ("He's got a cold can of Miller Lite, and he's dancing right now") to his faith in God to his love for his wife, Camila, and their three children, "the four people in my life that I want to make the most proud of me."
Celebrating at a party hosted by Madonna later that night, the star was "stuck like glue" to Camila and on "cloud 10," says a fellow guest.
And why not? "I try to give a lot to my life and the people in it," he tells PEOPLE, "and I know they sure give back. I have a lot to be thankful for."