A Strategic Guide to Deciding When to Leave Your 9–5

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Introduction: The Decision Before the Leap

For professionals, creators, and entrepreneurs, few decisions feel bigger than leaving a secure paycheck to pursue your own thing full-time. But the truth is: the decision isn’t made on the day you quit. It’s made in the months and years leading up to it, in how you track your progress, measure your risk, and prepare your foundation.

This playbook is designed to help you:

• Define the terms and metrics that matter when considering an exit.
• Audit your current situation with clarity, not emotion.
• Build the logic and evidence behind your decision.
• Create a roadmap that protects you against regret.

This is not a “quit your job tomorrow” manual.

It’s a strategic planning tool.

Use it as a workbook. Answer the questions honestly. Share it with a trusted peer.

The point isn’t speed … it’s clarity.

Key Terms to Know

Before mapping your exit strategy, get familiar with these foundational concepts: