Lenny's PodcastHow to make better decisions and build a joyful career | Ada Chen Rekhi (Notejoy, LinkedIn)
CHAPTERS
- 0:00 – 0:36
Avoiding the late-career trap: aligning work with meaning and values
Ada opens with a warning about drifting into a career that looks successful on paper but feels miserable in daily life. She frames the episode’s core theme: making decisions that balance achievement with meaning and values alignment.
- •The danger of lifestyle/inertia creating a feeling of being “trapped”
- •Career success vs. meaningfulness: you need both
- •Values alignment as the antidote to external expectations
- 0:36 – 3:45
Show setup: Ada’s background in startups, LinkedIn, SurveyMonkey, and coaching
Lenny introduces Ada’s career arc—from Microsoft to founding a startup acquired by LinkedIn, to SVP Marketing at SurveyMonkey, to co-founding Notejoy and coaching founders. He previews the major frameworks they’ll cover.
- •Ada’s roles: founder, growth/product marketer, SVP, coach
- •What the episode will cover: curiosity loops, values, career strategy, coaching
- •Starting a company with her husband and other personal angles
- 3:45 – 5:12
Curiosity loops: fast, structured advice-gathering for better decisions
Ada explains the “curiosity loop” she ran to pick podcast topics—getting high-quality feedback from a small group with minimal effort. The emphasis is on structure so the advice is contextual and actionable.
- •A curiosity loop as a lightweight, high-signal way to collect inputs
- •Why structure beats vague asks (“What should I do with my life?”)
- •Use it for big decisions when you feel indecisive
- 5:12 – 11:39
How to run a curiosity loop: craft the question, curate people, reduce cognitive load, close the loop
Ada breaks curiosity loops into a repeatable process: ask a strong question, pick the right mix of people, make the ask easy, then synthesize and report back. She also explains why this combats ‘bad’ (non-contextual) advice.
- •Good questions: specific, rationale-seeking, non-leading
- •Who to ask: subject-matter experts + people who know you well
- •Design for quick replies to maximize response rate
- •Process the input, then thank people and share outcomes
- 11:39 – 14:24
Curiosity loops in personal life: estate planning debate as a case study
Ada shares a personal example: resolving an estate-planning disagreement by casually polling trusted people over time. The loop surfaced surprising consensus and new research, shifting their decision-making baseline.
- •Applying curiosity loops outside work (family decisions included)
- •Using trusted conversations instead of deep solo research
- •Looking for surprises/disagreements as the most valuable signal
- •Reminder: inputs guide you—don’t blindly follow advice
- 14:24 – 16:28
Curiosity loops as “customer advisory councils” for your life
Ada connects the idea to marketing’s customer advisory councils: keeping a group of trusted “power users” to sanity-check product debates. She reframes the personal version as “user research for your life.”
- •Customer advisory councils: quick verbatims to resolve product debates
- •Translating product research habits to personal decisions
- •Use feedback to look around corners and spot blind spots
- 16:28 – 19:37
The values exercise: building an inner scorecard (live example with Lenny)
Ada introduces the values exercise she assigns coaching clients: quickly selecting and ranking values to create a personal decision scorecard. Lenny shares his values list, and they discuss how values often differ from public/status narratives.
- •10–15 minute process to identify and rank 3–5 core values
- •Values as an “internal scorecard” vs. status/money as external metrics
- •Lenny’s examples: adventure, optimism, generosity, growth, simplicity
- •Values can be updated over time as life changes
- 19:37 – 25:21
Using values to decide what to say yes/no to (and avoiding ‘obvious’ choices)
They apply Lenny’s values to real tradeoffs: adding projects (book/course/podcast) versus simplifying life for family. Ada highlights how ‘adventure’ can fade once execution becomes treadmill-like, making values a practical filter.
- •Values as a tool for prioritization and turning down ‘smart’ opportunities
- •Distinguishing novelty (adventure) from long-term operational grind
- •Making space for family/time by cutting non-essential commitments
- •Learning to say no as a core career skill
- 25:21 – 31:24
Early-career strategy: Ada’s “explore and exploit” framework
Ada shares how she rapidly progressed by intentionally switching between exploration (testing roles/industries) and exploitation (going deep once she found leverage). She narrates her path from Microsoft to startups to founding Connected.
- •Early career = explore with a hypothesis; later = exploit what works
- •Using each job as an experiment: pace, team size, function fit
- •Founding Connected as an exploration bet; acquisition as a pivot point
- •Being intentional about experiences over titles
- 31:24 – 35:34
When to leave a job: avoid ‘boiling frog’ inertia and optimize for learning
Ada offers a heuristic: watch for slow temperature increases—small misalignments that accumulate until you feel stuck. She advises using learning and growth as the key signal, then trying proactive role-shaping before quitting outright.
- •“Don’t be the frog”: monitor trends, not just the current state
- •Key diagnostic: are you still learning, stretching, and energized?
- •Try interventions first: conversations with managers, new projects
- •If stuck, use extra capacity to build skills/relationships for next steps
- 35:34 – 42:11
Logo collecting vs. values: inner vs. outer scorecards and Ada’s reevaluation trigger
They discuss the trap of optimizing for prestige (logos, titles) at the expense of joy. Ada shares how a high-profile opportunity prompted her to run a values check and realize it would fail her top priorities despite looking great on a resume.
- •Resume optimization can become a never-ending life strategy
- •Ada’s background pressures (e.g., achievement-focused upbringing)
- •Warren Buffett’s inner vs. outer scorecard framing
- •Values exercise as a guardrail against ego-driven decisions
- 42:11 – 44:59
Coaching hot take: most people don’t need a coach (and what to do instead)
Ada argues coaching is often over-prescribed: many goals are better met through curiosity loops, courses, mentors, or building community support. She encourages people to define the “six-month win” before paying for coaching.
- •Coaching is not the default answer—clarify what you want to achieve
- •Better alternatives: curiosity loops, structured learning (e.g., courses), community
- •A coach as a poor ‘mentor substitute’ if you need diverse viewpoints
- •“Anti-sell” mindset: make sure coaching is the best tool
- 44:59 – 51:35
When coaching is valuable: hypergrowth, sensitive topics, and picking the right coach
Ada explains when coaching shines: accelerated learning in chaotic roles (especially founders) and support on delicate interpersonal issues. She also shares how to select a coach—talk to multiple people and prioritize fit and psychological safety.
- •Best use cases: founders in chaos, fast scaling, high-stakes transitions
- •Coaches help with sensitive people issues and long-term development
- •Selection advice: interview 2–3 coaches; don’t just hire your friend’s coach
- •Fit matters more than credentials: vibe, safety, and being deeply understood
- •Multiple coaches can make sense for specialized, short-term goals
- 51:35 – 1:00:13
Advice for women in Silicon Valley: the ‘unwritten rules’ and getting hard feedback safely
Ada tackles why this topic feels risky to discuss, then shares a coaching story about appearance-based perception and bias—feedback many women never receive because it’s unsafe for managers to give. Her broader point: the game can be rigged, but you can still study the rules and build agency.
- •Leadership funnels are harsh; the rules are often unstated
- •Hard feedback (especially on perception/appearance) is rarely given at work
- •Coaches/peers can provide a safer channel for reality-based feedback
- •Build agency: learn the rules, help each other, and adapt intentionally
- 1:00:13 – 1:05:07
‘Eating your vegetables’: powering through early discomfort to build key skills
Ada introduces “eating your vegetables” as deliberate practice: sometimes you dislike something because you’re new/bad at it, not because it’s wrong for you. She shares how forced weekly networking reps built foundational relationships and confidence.
- •Discomfort vs. true dislike: you need repeated exposures to know
- •Deliberate reps (10–12+) as a strategy for skill acquisition
- •Networking example: weekly events, 10 business cards, ‘touch the back wall’ rule
- •Modern version: consistent outreach/DMs and structured practice
- 1:05:07 – 1:06:52
Write to crystallize knowledge (not for likes): content reps, authenticity, and audience-of-one
They discuss using writing and posting as practice rather than performance—focusing on learning, clarity, and genuine sharing. The goal is to reduce outcome obsession (likes/followers) and build a sustainable habit of thinking in public.
- •The “LinkedIn 30” as reps to get past the cringe barrier
- •Reframe: write to clarify your thinking; avoid chasing virality
- •“Write for an audience of one” to stay grounded and authentic
- •Consistency builds craft; engagement is a byproduct, not the goal
- 1:06:52 – 1:11:08
Building a company with your spouse: complementary domains, decision rights, and conflict hygiene
Ada explains why founding with a romantic partner can be uniquely volatile, yet can work exceptionally well with the right structure. She shares how she and her husband created clear ownership boundaries and practiced constructive conflict to protect both the business and the relationship.
- •Founder life is intense; adding romance increases volatility
- •Keys to making it work: complementary skills and clear decision rights
- •Use explicit check-ins (30/60/90) and prioritize relationship health
- •Constructive conflict: attack the problem, not each other; assume good intent
- 1:11:08 – 1:18:27
Lightning round: books, shows, interview question, favorite tools, and productivity tip
Ada closes with rapid recommendations across learning, entertainment, interviewing, tools, and productivity. She emphasizes persuasion principles, designing a fulfilling life, and a practical ‘five-minute start’ tactic to beat procrastination.
- •Books: Cialdini’s *Influence*; *Designing Your Life*
- •TV: *Ted Lasso*; *Star Trek: Strange New Worlds*
- •Interview question: “What’s a common misconception about you?”
- •Tools: Notejoy, Captio, Arc browser
- •Productivity: pick one priority and start with just five minutes
