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037 - Alexander Hamilton - I Am Not Throwing Away My Shot
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037 - Alexander Hamilton - I Am Not Throwing Away My Shot

A seventeen-year-old clerk wrote his way off a Caribbean island, then spent decades making sure the people deciding his future already had the evidence they needed

Somewhere in your organization, a group of leaders sits down once or twice a year and talks about people. Who’s strong. Who’s stuck. Who could step into a bigger role. You’re not in that room, and your name almost certainly comes up. Alexander Hamilton understood that dynamic better than almost anyone in American history, and he refused to leave it to chance. In this episode we follow him from a hurricane letter in St. Croix to the Treasury Department, and look at what it means to feed the conversation about your future instead of waiting for it to happen to you.

What we cover:

  • The hurricane letter of 1772: how a seventeen-year-old orphan with no connections produced something so undeniable that an entire community pooled their money to send him to the colonies

  • King’s College and the pamphlets: why Hamilton didn’t wait to be invited into the political conversation and what he did instead to make the people already in it want him there

  • Robert Greene’s Mastery and the idea that the apprenticeship phase is about positioning yourself to be seen, while producing work that makes advancement feel inevitable

  • The aide-de-camp years: how Hamilton served Washington brilliantly while repeatedly and explicitly telling him he wanted a field command, and why saying what you want out loud to someone with a vote matters

  • The Katherine Johnson connection: two people, two centuries, the same discipline of producing next-level evidence before the next level is offered

  • On the plan, labeled, or developed: the three different ways your name can sit in a talent conversation, and why only one of them moves your career

  • The Federalist Papers: fifty-one essays under a pseudonym, and how Hamilton made himself the obvious choice for a Treasury that didn’t yet exist

  • Treasury Secretary at thirty-four: why Hamilton defined the role instead of waiting to be told what it was

The question to bring to your next one-on-one:

How do you see my path here? Are you thinking about me for bigger roles, and if so, what would you need to see from me to feel confident? Then stop talking. If the answer is vague, follow with: what’s the one thing that would most change your read on my readiness?

Referenced in this episode:

  • “My Shot,” Lin-Manuel Miranda, from the original Broadway cast recording of Hamilton (2015)

  • Hamilton: An American Musical, Lin-Manuel Miranda

  • Mastery, Robert Greene

  • The Ready Set episode (019) on Katherine Johnson


This episode is inspired by and aligned with the latest Ready Set article published on Substack: Are You On the Plan? Find it at thereadyset.c2advising.com.


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