How to make better decisions and build a joyful career with Ada Chen Rekhi

Executive overview

Most career advice fails because it isn't contextual — it doesn't account for who you are, what you value, or what you actually want. Ada Chen Rekhi offers two practical tools to fix this: Curiosity Loops for better decision-making and a values exercise for building an internal scorecard.

Use curiosity loops to crowdsource structured input before big decisions. Use your values to filter out the "obviously smart" moves that would quietly make you miserable.

The real trap isn't making the wrong choice — it's optimising for the external scorecard so long that you wake up late-career, successful, and unhappy.

The curiosity loop framework

• Ask a specific, unbiased question that solicits rationale — not "what should I do?" but a concrete scenario with something to anchor on
• Curate two types of respondents: subject-matter experts and people who know you well
• Keep the ask lightweight so busy people can respond in a few minutes
• Target at least 3–4 responses; email 5–10 people depending on your expected response rate
• Process the responses, look for surprises and disagreements — those are the signal
• Close the loop: thank people and share what you decided; it feels good to be heard

The values exercise

• A 10–15 minute exercise: scan a list of value words, pick what resonates, filter into groups, stack rank
• Output: 3–5 sentences capturing what actually matters to you right now, personally and professionally
• Acts as an internal scorecard to evaluate decisions against — separate from status, title, or external validation
• Run it when facing a major decision; "obvious next step" careers often fail this test
• Values shift over time — revisit and update as life changes
• The ego monster and Warren Buffett's inner vs. outer scorecard are useful mental models for the same idea

Early career strategy: explore and exploit

• Explore early: test hypotheses about what you like, what fits, what you're good at — with intentionality, not randomly
• Exploit once you've found something rich: go deep, get more
• At each job, be explicit about what you're there to learn — not just what title you're chasing
• Ada's path: Microsoft (corporate too slow) → Mochi Media startup (loved marketing, small teams) → founded Connected (learned founding) → LinkedIn (deliberately learned growth and subscriptions) → SVP Marketing at SurveyMonkey at 27
• Don't be the frog: watch the temperature of your environment, not just today but the direction it's trending
• When growth stalls: have a proactive conversation with leadership, or treat the extra capacity as a gift of time to build skills independently

When to get a coach — and when not to

• Most people probably do not need a coach; explore alternatives first: curiosity loops, structured courses, building a community
• A coach is a poor substitute for a mentor (one opinion), a course (breadth of knowledge), or a tribe (long-term emotional support)
• Coaching adds most value during hypergrowth phases (founders especially) and on sensitive long-term interpersonal issues
• Talk to 2–3 coaches before committing; personal connection and psychological safety matter more than credentials
• Consider niche coaches for specific short-term goals (pitch coaching, writing) rather than one long-term relationship
• Half of people hire the first coach they talk to — don't do this

Being a woman in Silicon Valley

• The rules of the career game often go unstated, especially around physical presence and first impressions
• Feedback on appearance and perception is rarely given — because it's risky to give — leaving people to navigate blind
• Hard feedback, given from a place of care, can be transformative; withholding it is a form of selfishness
• The game may be rigged, but you're not powerless: study the rules, help each other, find workarounds
• Radical Candor framework: challenge directly while demonstrating you care deeply about the person

Eating your vegetables: deliberate practice

• Dislike something because you're new to it vs. genuinely disliking it after real exposure — these are very different
• Research suggests 10–12 exposures before developing an affinity; don't quit after one bad try
• Ada's networking rule: attend one external event per week, hand out 10 business cards, touch the back wall before leaving
• Modern equivalent: LinkedIn 30-day posting challenge; DM people you find interesting online
• Reframe LinkedIn posting: not self-promotion, but crystallising a useful thought for an audience of one

Starting a company with your partner

• Strong upside when complementary skill sets are clearly defined and decision rights are unambiguous
• The biggest risk: founders are already in an emotionally volatile state — adding romance amplifies highs and lows
• Critical success factor: ability to attack the problem, not each other — truth-seeking over personal defensiveness
• Use explicit check-ins (30/60/90 day) to ensure the business isn't damaging the relationship
• Results are bimodal: it goes really well or really badly — know which one you're likely to be before starting