Career Transitions

This one taps into frameworks from 76 product leaders who've actually made big career pivots. Use it when you're weighing a job offer, thinking about switching into PM, or feeling stuck. It pushes you to run small experiments before burning bridges, helps you separate what you're running from versus toward, and includes specific mental models like the Genie Framework (what would you do if failure wasn't possible?) and treating your career like a product with testable hypotheses. The advice skews toward progress over pay and relationship building over ladder climbing, which honestly feels more realistic than the usual career guidance. Good for when you need structure around a fuzzy decision.

skills.sh installs: 2.2K
GitHub stars: 1.5K
last updated: Aug 21, 2026

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Install

$ npx -y skills add refoundai/lenny-skills --skill career-transitions --agent claude-code

Installs into .claude/skills of the current project.

Files

Navigating Career Transitions

Move beyond the default path by optimizing for high-growth environments and internal energy.

Help the user with navigating career transitions using insights from 24 guests and posts across Lenny's Podcast and Newsletter.

How to Help

Audit current fit - Use data-driven frameworks to assess if your current environment supports your unique skill set.
Identify energy sources - Move away from logical checklists to find roles that generate internal excitement and heat.
Evaluate organizational quality - Look past titles to verify leadership commitment to growth and partner quality.
Plan the transition - Create intentional space between roles to shed old habits and prepare for new cultural norms.