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Principles for Second 10 Years at Work

· 6 min read

Early career focuses on continuous learning, gaining specialized expertise, and building foundational leadership skills, while late career shifts toward creating strategic impact, mentoring the next generation, and leaving a meaningful legacy that shapes industries, communities, or personal networks.

1. Start with the customer

  • 1.1 Surface yourself to internal and external buyers and sellers through online and offline platforms
  • 1.2 Conduct customer interviews and gather feedback regularly
  • 1.3 Empathize with customer pain points and act as a proxy for customers
  • 1.4 Predicting and producing what the customer loves is hard, but we can always invent and simplify our product to a better state
  • 1.5 Prioritize features and initiatives that provide the most customer value
  • 1.6 Measure success with customer satisfaction metrics (e.g., NPS, CSAT)

2. Sharpen your communication skills

  • 2.1 Be genuinely interested in people and actively wonder what they are doing/needing/feeling
  • 2.2 Practice and rehearse clear, concise writing and speaking until you're fully prepared for interviews
  • 2.3 Adapt your communication style to suit your audience
  • 2.4 Continuously seek feedback to refine your communication skills
  • 2.5 Leverage storytelling to make complex ideas more relatable and engaging
  • 2.6 Use examples, metaphors, and narratives to simplify and humanize technical or abstract concepts
  • 2.7 Apply communication frameworks like Thank/Reflect/Wish, PREP (Point/Reason/Example/Point), AIDA (Attention/Interest/Desire/Action), and STAR (Situation/Task/Action/Result)

3. Focus on high-leverage, prioritized activities

  • 3.1 Score and identify tasks with the most significant impact on key objectives
  • 3.2 Use frameworks like Eisenhower Matrix or OKRs to prioritize tasks
  • 3.3 Automate or delegate low-impact tasks
  • 3.4 Review priorities regularly to ensure alignment with goals
  • 3.5 Build flexibility into your schedule by leaving space for unplanned activities, and compensate for intense periods with planned downtime

4. Accelerate learning through high-value channels, execution, and accumulation

  • 4.1 Learn by doing, sharing, and documenting: Take on new projects, challenges, and record key lessons
  • 4.2 Seek feedback from peers and mentors after each task, and incorporate it into a personal knowledge base
  • 4.3 Engage in inter-person communication to uncover hidden, tacit knowledge that is often only discovered through direct interaction
  • 4.4 Embrace failure as part of the learning process, fail fast, and capture insights to avoid repeating mistakes
  • 4.5 Continuously iterate on ideas and processes, building upon past successes and failures to compound learning over time

5. Ask high-value questions

  • 5.1 Challenge assumptions and conventional wisdom with first principles
  • 5.2 Guide strategic decisions by focusing on questions that reveal hidden insights and drive long-term impact
  • 5.3 Search for who is asking what questions globally to identify the most important questions
  • 5.4 Answers are cheap in the age of LLMs. Prioritize asking the right questions

6. Strategic thinking: from small wins to big wins

  • 6.0 Understand the history, status quo, and predict the future with long-term vision
  • 6.1 Break down large goals into smaller, actionable tasks
  • 6.2 Do not shoot for a moving target – maintain focus on clear, stable goals
  • 6.3 Collect data and establish benchmarks to evaluate success
  • 6.4 Identify areas where short-term wins can unlock long-term success
  • 6.5 Celebrate quick wins while keeping an eye on long-term goals
  • 6.6 Regularly review progress and adjust strategies as needed

7. Build allies

  • 7.1 Network widely to broaden your influence
  • 7.2 Help others succeed to build trust and reciprocity
  • 7.3 Collaborate across teams to expand your impact
  • 7.4 Stay in touch and offer support consistently
  • 7.5 Build trust through personal, in-person connections
  • 7.6 Exchange value in every interaction
  • 7.7 Stay active in key professional circles
  • 7.8 Nurture relationships for long-term mutual benefit

8. Stay resilient, optimistic, and pragmatic

  • 8.1 Focus on identifying the right problem and finding effective solutions when challenges arise
  • 8.2 Maintain a positive mindset, especially during setbacks (Reframing, expressing gratitude, etc.)
  • 8.3 Balance optimism with a realistic view of the situation by synthesizing

9. Influence without authority

  • 9.1 Build credibility by demonstrating expertise and delivering results
  • 9.2 Persuade through data and clear reasoning
  • 9.3 Leverage relationships to gain support for your ideas
  • 9.4 Be collaborative, listen to others, and align their goals with yours

10. Be assertive and open-minded

  • 10.1 Speak up confidently in meetings and discussions
  • 10.2 Seek feedback and adjust your approach if needed
  • 10.3 Advocate for your ideas but be willing to change if presented with better information
  • 10.4 Actively listen to others by mirroring, mentalizing, and showing genuine care
  • 10.5 Recognize the role of emotions in interactions and continuously improve your emotional intelligence (EQ)

11. Compete with focus and advantages

  • 11.1 Build a strategy based on specific market needs or niches you can dominate
  • 11.2 Identify and leverage your unique advantages (skills, location, resources)
  • 11.3 Focus on areas where you can outperform others with specialized knowledge or capabilities
  • 11.4 Anticipate future trends and invest in building advantages ahead of time
  • 11.5 Stay focused on your strengths and avoid unnecessary distractions
  • 11.6 Realize people can be both allies and competitors at the same time

12. Mentor and grow others

  • 12.1 Share your knowledge and expertise to help others succeed
  • 12.2 Offer guidance and feedback to team members regularly
  • 12.3 Create opportunities for others to take on new challenges
  • 12.4 Foster a culture of learning and development in your teams
  • 12.5 Leverage media and public platforms to inspire and educate others at scale

13. Stay approachable and flexible

  • 13.1 Remain accessible and responsive to buyers and customers at all times
  • 13.2 Be open to feedback and discussions with colleagues, buyers, and customers at all levels
  • 13.3 Maintain a friendly, open demeanor that encourages collaboration
  • 13.4 Adapt to changing situations without becoming rigid in your approach
  • 13.5 Stay calm and open-minded when unexpected challenges arise
  • 13.6 Be proactive so that the schedule is more favorable to the initiator

14. Lean in but avoid burnout

  • 14.1 Take initiative, but know your limits and learn to manage expectations
  • 14.2 Set boundaries to protect your personal time
  • 14.3 Regularly evaluate your workload, delegate where possible, and schedule regular downtime

15. Physical and mental well-being fuel everything else

  • 15.1 Make a checklist to monitor personal status regularly
  • 15.2 Maintain a regular exercise routine for MIIT, HIIT, Strength, and Flexibility exercises
  • 15.3 Prioritize sleep and proper nutrition
  • 15.4 Practice mindfulness or meditation to manage stress
  • 15.5 Take regular breaks to recharge, both mentally and physically
  • 15.6 Foster an environment where people love to live and work
  • 15.7 Learn to navigate your brain willfully through Relaxed, Focused, and Overheated states, and avoid Overheated states

16. Be creative and stand out

  • 16.1 Seek inspiration from different fields and industries
  • 16.2 Challenge assumptions and ask "what if" questions
  • 16.3 Experiment with different methods and technologies