Career

Structure your first 90 days around listening, aligning, then executing

Every career has a highlight reel (A-side) and a struggle story (B-side)—both are essential for resilience and perspective

Reframe failures and setbacks as learning opportunities with this memorable acronym

Young people who grow up with AI tools have a generational competitive advantage

In the AI era, management skills become universal as everyone becomes a model manager

10 years from now, what will you regret if you don't learn it or do it now?

Break out of unconscious daily routines to live intentionally

Start with simple businesses to build entrepreneurial muscle before tackling harder ones

Take agency to shape your career and outcomes rather than waiting for opportunities

Focus on creating the one thing that wouldn't exist without your unique insight and expertise

Monitor sleep, relationships, health, and emotional stability—when these break down, something must change

Maximize career options rather than optimizing for specific titles or linear progression

Life is suffering, so figure out something worth suffering for

Sustained effort matters more than immediate achievements—don't give up, keep working at it

Find your topic by identifying what makes everyone at the dinner table lean in when you talk about it

A heuristic for recognizing when gradual deterioration means it's time to leave

Build skills through repeated exposure, not natural affinity—10-12 tries before you know if you like something

Focus on industries where 10x productivity creates 10x more demand, not 10x fewer jobs

Schedule your time around your energy levels, not just availability

A growth mindset framework for navigating early career through intentional experimentation

Work adjacent to the CEO's top priority, not directly under it

Write regularly for two years and you'll become known in your field

Don't let your professional identity limit what you can become

Double down on what gets unexpected traction rather than sticking to your original plan

A process for fundamental life change: Suffering → Seeking Truth → Self-Compassion → Compassion for Others

Own outcomes end-to-end, not just features—think like a full-stack influencer

What would you do if you knew you wouldn't fail?

Ten criteria for identifying companies with real momentum before joining

Maximize career impact by optimizing environment variables and skills

Use imposter syndrome as a signal to level up rather than a reason to hold back

Focus on passion and mission, not every possible downside

A four-step cycle for accelerating PM skill development through execution, generalization, communication, and scaling

Ladder between periods of high learning and high impact throughout your career

Be willing to look dumb and ask dumb questions repeatedly—it's how you actually learn

Don't move into management until technical skills feel like second nature

Build a portfolio of 3-4 mentors you meet monthly, not a single mentor relationship

Mentors can be anyone—investors, employees, people you mentor, even interns—stay ready to learn

Master three levels of the game simultaneously to stay ahead as a founder

Join 300-500 person companies that have product-market-channel fit and are becoming platforms

Midlife is not crisis—it's the transformational cocoon between caterpillar and butterfly

Be both wise and curious—a mentor who is also an intern

Two paradigms for life: relentlessly achieving goals vs. surrendering to where life's current takes you

Design nine alternative lives you'd be excited to live

Early career, prioritize learning velocity over titles—compound interest kicks in later

Prioritize things that compound (health, relationships, skills) over minimizing regret

Competitive advantage comes from the painful learning journey others avoid

Four distinct routes to transition into product management from other functions

Build a community of peers and mentors who help you see around corners in your career

Keep your personal learning rate ahead of your company's growth rate

Three essential traits for PM success: intelligence, grit, and influence

Product management skills directly translate to AI tool proficiency—PMs are best positioned to thrive in the AI era

PMs range from crazy innovators to pure executors—the sweet spot is strategic executors in the middle

Apply product management rigor to your career—specs, milestones, metrics, and roadmaps

A framework for evaluating job opportunities using three criteria: People, Mission, and Financials

Choose opportunities based on the problem you're solving and who you're solving it for, not the product domain

Free up headspace for thinking by externalizing everything

The difficult gap between senior IC and product leader that many PMs fail to cross

Evaluate job decisions by emotionally embodying the role, not spreadsheet analysis

The trait of insatiably seeking to understand things without fear of appearing ignorant

The ability to persist through 70-80% experiment failure rates without thinking too small

Accept that painful trial and error is essential to truly learning product management

Great careers are built by knowing people doing great work, being curious, and seizing unexpected opportunities

In interviews, demonstrate how your work made a difference—not just what you did

Find people willing to bet their capital on your success, not just give advice

Career breakthroughs come from sponsors who trust you with big opportunities, not mentors who give advice

The most successful people transform failures and setbacks into career accelerants

Discover your unique strengths by mining peak experiences from your past

Recognize how intelligence creates learning blocks and overcome them

A five-step career advancement framework that creates mutual benefit between you and your manager

Distributed risk across many customers feels safer than concentration with one employer

Spend one week solving a real problem with AI to join the top 1%

Deliberately rotate through different functions to build executive readiness

Your eyes, ears, and intellect have intrinsic value—believe in your own judgment

Major life transitions involve leaving one identity mountain, crossing a difficult valley, and ascending a new one

Understand two levels above and below your role, plus what's happening to your left and right

Life satisfaction bottoms out around 45-50, then rises through your 50s, 60s, and beyond

A structured process to identify and stack-rank your personal values for better decisions

When changing companies, hold onto values but recalibrate behaviors to fit the new culture

The skills that earned your current position are different from the skills needed for the next level

Being a mid-level IC at a category winner beats being a senior leader at a tier-two player

Write to crystallize your thinking—reading makes you wise, writing makes you think

Personal growth requires finding your own way, not following someone else's established path

A company that won't die but you can't leave is worse than failure—know when to let it go.

Operate in the space where you're exceptional and derive tremendous joy