career-transitions
This skill helps users navigate career transitions by applying frameworks from 76 product leaders who successfully changed roles, industries, or career stages. Use it when someone is considering a new position, exploring function changes, evaluating sabbaticals, assessing job offers, or feeling stuck in their current role. The skill guides users through identifying transition types, uncovering motivations, evaluating readiness, and designing low-risk experiments to test career hypotheses before committing to major changes.
git clone --depth 1 https://github.com/RefoundAI/lenny-skills /tmp/career-transitions && cp -r /tmp/career-transitions/skills/career-transitions ~/.claude/skills/career-transitionsSKILL.md
# Career Transitions Help the user navigate career changes using frameworks from 76 product leaders who have successfully pivoted roles, industries, and career stages. ## How to Help When the user asks for help with a career transition: 1. **Identify the type of move** - Determine if they're seeking a new role, new function, new stage, or entirely new path 2. **Understand motivations** - Uncover the "pushes" (frustrations) and "pulls" (attractions) driving the change 3. **Assess readiness signals** - Help them evaluate if now is the right time or if preparation is needed 4. **Design experiments** - Suggest low-risk ways to test hypotheses before committing fully ## Core Principles ### Progress matters more than pay Bob Moesta: "Over 50% of the people who got new jobs didn't get more money. It's a lie. It's about progress. It's about what do they want to learn? What skills do they want to get?" Identify your "metric of progress" - what growth looks like for you specifically. ### Use the Genie Framework Graham Weaver: "What if you had one wish... whatever you throw yourself into, it's going to turn out great." Remove fear of failure from the equation to identify what you actually want. Work backwards from a successful 10-year outcome. ### Build serendipity through relationships Gokul Rajaram: "Great careers are built by knowing a lot of people doing great work so they know and want you on their teams, and just waiting for serendipity and then seizing it." Prioritize building relationships with smart people over linear promotion paths. ### Follow intuition over spreadsheets Ami Vora: "The thing that has consistently served me is to do the thing that feels right, go to the place that feels like home, work with the people who feel like my friends." Choose roles where you feel "lucky" to be there. ### Three months is attainable Paul Millerd: "A three month sabbatical is much more attainable than people think... if you're assuming you're going to work continuously in adulthood, that's about 500 months." Frame sabbaticals as a tiny fraction of your total career to make them feel possible. ### Treat your career like a product Gibson Biddle: "It's just a lot like building a product. You have theories and hypotheses, you find ways to experiment with them." Run small experiments to test career hypotheses before making big commitments. ### Internal moves are easier Anneka Gupta: "Doing it within the same company is a lot easier than trying to switch companies and switch jobs at the same time because you've already built credibility." Leverage existing relationships and domain knowledge for role transitions. ### Balance learning and impact Deb Liu: "You can have the most impact in the job you know the best, but then you stop learning... How do you keep going back and forth so that you're not going straight up?" Alternate between mastery roles and "newbie" roles to avoid stagnation. ### Join winning teams Matt MacInnis: "As an early career product manager... you should join a winning team. I want to hear what they learned from being part of a winning team." High-growth companies provide more learning than struggling ones. ## Questions to Help Users - "If success were guaranteed, what would you pursue?" - "What are you running away from versus running toward?" - "When did you last feel truly energized by your work?" - "What would you do if you didn't have to make money?" - "Who are the three people whose careers you most admire?" - "What's the smallest experiment you could run to test this path?" ## Common Mistakes to Flag - **Optimizing for compensation early** - Early career earnings are negligible compared to back-loaded executive compensation - **Staying due to inertia** - Monitor if your environment still provides learning or if you're the "boiling frog" - **Title chasing** - A senior role at a losing company often beats a junior role at a market leader - **Skipping the sabbatical buffer** - Moving between intense roles without recalibration leads to carrying old culture baggage - **Ignoring the "habitat" fit** - Failing in one environment doesn't mean you lack skills; it may mean wrong environment ## Deep Dive For all 111 insights from 76 guests, see `references/guest-insights.md` ## Related Skills - Building a Promotion Case - Negotiating Offers - Finding Mentors & Sponsors - Managing Imposter Syndrome
Help users create and run AI evaluations. Use when someone is building evals for LLM products, measuring model quality, creating test cases, designing rubrics, or trying to systematically measure AI output quality.
Help users define AI product strategy. Use when someone is building an AI product, deciding where to apply AI in their product, planning an AI roadmap, evaluating build vs buy for AI capabilities, or figuring out how to integrate AI into existing products.
Help users synthesize and act on customer feedback. Use when someone is analyzing NPS responses, processing support tickets, reviewing user research, synthesizing feedback from multiple channels, or trying to identify patterns in customer input.
Help users apply behavioral science to product design. Use when someone is designing for habit formation, reducing friction, applying psychology to UX, increasing retention through behavioral principles, or using nudges to influence user behavior.
Help users craft compelling brand narratives. Use when someone is defining brand strategy, writing company positioning, creating pitch narratives, developing messaging frameworks, or trying to make their company story more memorable.
Help users get promoted at work. Use when someone is preparing for a promotion conversation, building their case for advancement, trying to understand what's blocking their promotion, or figuring out how to get to the next level in their career.
Help users build and scale their sales organization. Use when someone is hiring their first salespeople, deciding when to bring on sales leadership, structuring sales compensation, or transitioning from founder-led sales.
Help users build and maintain strong team culture. Use when someone is defining team values, creating psychological safety, onboarding to a new team, navigating cultural change, or building distributed team norms.