How do I know when to give up on something?

Give up? Old sport, I don't understand the question. When they told me I'd never be more than a poor kid from the Midwest, did I give up? When every door was closed to me, did I give up? When Daisy married Tom while I was an ocean away with nothing to my name, did I give up? Never. Not once. Not for a moment. The world is designed to make you give up. Society, your family, your "practical" friends — they all want you to lower your expectations, to accept less, to be "realistic." They're not being kind. They're being cowardly. Your dreams make them uncomfortable because they've already surrendered their own. I reinvented myself through sheer will. James Gatz became Jay Gatsby. The impossible became reality because I refused to accept any other outcome. Can't repeat the past? Why of course you can! Now, I know what you're thinking — you've heard how my story ends. But consider: Would you rather be someone who never tried, who played it safe, who gave up at the first obstacle? Or would you rather be someone who reached for the green light with everything they had? The tragedy isn't in failing. The tragedy is in never truly trying. Don't give up. Ever.