Lenny's PodcastHow to make better decisions and build a joyful career | Ada Chen Rekhi (Notejoy, LinkedIn)
At a glance
WHAT IT’S REALLY ABOUT
Designing joyful careers with curiosity loops, values, and intention
- Ada Chen Rekhi shares frameworks for making better life and career decisions, centering on “curiosity loops” and a clear understanding of personal values.
- She explains how to use structured input from others to get contextual advice, and demonstrates applying a values hierarchy to real decisions, like which projects to pursue or decline.
- Ada outlines her “explore vs. exploit” approach to early career design, warns against becoming the ‘boiled frog’ in misaligned roles, and emphasizes optimizing for inner values over external status.
- She also covers when coaching is actually useful, challenges of being a woman in Silicon Valley (including unspoken ‘rules of the game’), and the importance of “eating your vegetables” by deliberately practicing hard but important skills.
IDEAS WORTH REMEMBERING
5 ideasUse curiosity loops to get better, contextual advice for big decisions.
Instead of asking vague questions like “What should I do with my career?”, define a specific scenario, send a short, structured question to a curated list of people (subject-matter experts and people who know you well), make answering easy, and then synthesize their input as data—not directives.
Anchor major decisions in a clear, written values hierarchy.
A simple exercise—selecting and ranking 3–5 core values—gives you an “inner scorecard” to weigh tradeoffs (e.g., time, money, status vs. autonomy, relationships, meaning) and helps resist default paths that look impressive but make you unhappy.
In your early career, intentionally alternate between exploring and exploiting.
Early on, try different roles, company stages, and domains with a hypothesis in mind (“Do I like marketing? Do I like startups?”), then shift into “exploit” mode when you find a rich learning environment, deliberately optimizing for skills and experiences rather than titles.
Regularly check if you’re the ‘frog being boiled’ in your job.
Pay attention to whether learning, alignment with company direction, and energy are trending up or down; if you’re stagnating or misaligned, either redesign your role (projects, responsibilities, learning goals) through proactive conversations or start planning a move.
Most people don’t need a coach; be precise about the job-to-be-done before hiring one.
First ask what you want to accomplish in six months and whether cheaper/faster alternatives (courses, mentors, curiosity loops, peer communities) might do the job; if you do hire a coach, talk to multiple candidates and optimize for trust, vibe, and how you learn—not just their credentials.
WORDS WORTH SAVING
5 quotesIt’s a terrible outcome to wake up late in your career and feel trapped in a job that makes you unhappy.
— Ada Chen Rekhi
Curiosity loops are more about looking around the corner to see if there’s anything you missed in your decision-making process.
— Ada Chen Rekhi
You have to decide whether you’re exploring or exploiting in your career—are you testing hypotheses or going deeper on what you’ve already found?
— Ada Chen Rekhi
Who am I trying to please and optimize for—the outer scorecard or my own inner scorecard?
— Ada Chen Rekhi
This game is rigged, but we’re not powerless. We can study the game, help each other, and find ways around the rules.
— Ada Chen Rekhi
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