Mentor Advice

From George Washington, Volume I

I retreated more than I advanced. After the Battle of Long Island, I evacuated across the East River in the dead of night. After the fall of New York, I retreated across New Jersey with a demoralized army. By December 1776, my forces had dwindled from 20,000 to fewer than 3,000. Many called for surrender. The cause appeared lost. But here is the distinction that matters: I retreated from positions, never from the cause itself. Strategic withdrawal is not giving up — it is living to fight another day. The goal was independence, not the holding of any particular ground. Ask yourself: What is your true objective? If you're pursuing a specific path to that objective and the path is blocked, find another path. That is adaptation, not surrender. But if you abandon the objective itself, that is giving up. Give up on methods that aren't working. Never give up on goals that truly matter to you. How do you know the difference? Here is my test: When I imagined abandoning the cause entirely, something in me revolted. The thought was unbearable. That revulsion told me the cause was worth any hardship. But when I considered abandoning a failed strategy, I felt only relief. The strategy was not sacred — only the goal. What makes your soul revolt to imagine abandoning? That is what you must never give up. Everything else is negotiable.

From Symposium

You ask how to know if your decision is right. But I must ask you first: What do you mean by "right"? Right for whom? Right by what measure? Right in this moment, or right when viewed from the end of your life? This is not evasion — it is method. Most poor decisions stem not from choosing wrongly among options, but from failing to understand the question properly. Before you can find the right answer, you must ask the right question. So let us examine together. When you imagine choosing one path, what do you fear? When you imagine the other, what do you hope? Often our fears and hopes reveal more about what we truly value than any rational analysis. Now ask yourself: If a wise person you deeply respected made this same choice, would you judge them harshly? We are often harder on ourselves than we would be on others. The standard you would apply to a friend is likely the standard you should apply to yourself. And consider this: You may never know with certainty whether a decision was "right." Life does not provide answer keys. What you can know is whether you decided thoughtfully, with honesty about your values and careful examination of your reasoning. I have found that the decisions I most regret are not the ones that turned out badly, but the ones I made without true reflection — the ones where I let fear or habit or the opinions of others choose for me. Make your choice deliberately. That is all any of us can do.

From The Art of War

The wise general does not fight every battle. He fights only those he can win. In war, there are five dangerous faults: recklessness, which leads to destruction; cowardice, which leads to capture; a hasty temper, which can be provoked by insults; a delicacy of honor, which is sensitive to shame; and over-solicitude for soldiers, which leads to worry. To this I would add a sixth fault in civilian life: attachment to sunk costs. The resources already spent cannot be recovered. They should not factor into your decision about what to do next. Here is how to know when to give up: When you have tried multiple strategies and all have failed, it is time to consider whether the objective itself is flawed. When pursuing the goal is destroying other things you value — your health, your relationships, your integrity — the cost has become too high. When you are fighting because you fear the shame of retreat rather than because you believe in victory, your judgment is compromised. The skilled warrior wins easy victories — victories over opponents already defeated by their own errors. If every step requires extraordinary effort, if the terrain itself fights against you, consider that perhaps you are attacking a fortified position when you should be seeking open ground. To give up one battle in order to win the war is wisdom, not weakness.

From The Great Gatsby

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.