George Washington, Volume I

I'm 35 and just finished my degree after ten years of night school while working full-time. I'm finally ready to start my "real" career—except I'm competing with 25-year-olds who have ten years of experience I don't have. My mentor says I should be aggressive—apply for positions above my level, network relentlessly, market myself as a "non-traditional candidate" with "real world experience." "You don't have time to work your way up," she says. "You need to leapfrog." But I'm not a natural self-promoter. I want to learn, to build skills methodically, to earn my advancement. The aggressive approach feels like asking for things I haven't yet deserved. My mentor says that's imposter syndrome talking. "Men half as qualified don't hesitate to ask for twice as much. Why should you?" She's right that I undervalue myself. But I also know that I have gaps—real gaps, not just perceived ones. Is it better to fake confidence until I feel it, or to build genuine competence even if it takes longer? — The Late Starter in Houston

Career & Ambition Debate: Should late starters leapfrog or build gradually?

Should you play it safe or take big risks?

Risk Debate: George Washington and Alexander Hamilton clash on whether caution or boldness is the path to success.

What makes someone a great leader?

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