Career Growth Roadmap - De-risking Your Career By Understanding Your Vulnerabilities
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Jan 20, 2026
Discover how to transform your career by identifying hidden vulnerabilities. Learn to list the people and situations influencing your choices. Understand how debt can hold your career hostage and explore the dynamic of healthy versus unhealthy vulnerability. Jonathan shares a unique 'pre-mortem' exercise that helps you prepare for potential failures. By eliminating financial burdens, you can reclaim your autonomy and make principled career decisions. Gain insights to differentiate imagined risks from real ones and trade control for greater freedom.
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volunteer_activism ADVICE
Map Your Decision Levers
List the people, situations, and physical things that drive your decision-making today.
Then identify what changes could shift those decisions so you can plan to reduce harmful leverage.
insights INSIGHT
Values Can Become Hostages
Some powerful values align with you, while others can hold you hostage and push choices you wouldn't otherwise make.
Recognize which influences are protective values and which are coercive vulnerabilities.
question_answer ANECDOTE
Debt Versus Relationship Vulnerability
Jonathan contrasts relational vulnerabilities like family with coercive ones like large debt.
He notes health, relationships, and debt differently influence career choices and agency.
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In this episode, we explore how to de-risk your career roadmap by identifying the hidden vulnerabilities that hold your decision-making hostage.
🎧 Episode Notes: De-risking Your Career By Understanding Your Vulnerabilities
True career growth requires gaining autonomy over your choices. This episode provides a framework for performing a "pre-mortem" of career failure by identifying the sources of power that currently influence your life and limiting their leverage over your future.
Identify Your Sources of Power: Perform an exercise to list the people, situations, and physical things (like money or debt) that drive your current decision-making and could shift your behavior if they changed.
Conduct a Career "Pre-mortem": Use this diagnostic approach to recognize what has the power to change your decisions, helping you prepare for potential failures before they occur.
Understand the "Hostage" Dynamic: Realize that while some leverage is aligned with your values, other factors—like large amounts of debt—can hold your career hostage, forcing you to make decisions you otherwise wouldn't.
Balance Vulnerability and Autonomy: Distinguish between healthy vulnerability (such as in relationships with family) and unhealthy vulnerability (such as with creditors), and work to de-risk the latter to reclaim your agency.
The Link Between Debt and Career Risk: Learn how eliminating financial vulnerabilities, like credit card debt, increases your autonomy, potentially allowing you to take "principled" career risks you previously couldn't afford.
Re-evaluate Your Non-Negotiables: Use introspection to determine which parts of your job are truly essential and which "imagined" risks are preventing you from seeking better alignment with your personal purpose.
Shift Your Control Systems: Understand that growth often requires giving up control in one area (like spending habits) to gain control and autonomy in your professional path.
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