Life Chapters: Reflections on Learning and Earning
This essay is autogenerated from my x.com threads.
Looking backward in life is like reading a book you’ve already finished—you know the outcome, so everything seems obvious. Looking forward is a different game entirely. The choices we have yet to make, the paths not yet taken—these are the questions we should be wrestling with now, before the final chapters are written.
Think in Chapters
Our lives are not one continuous grind. It helps to break them into big, distinct chapters. Just like in a startup, you might define “milestones” or “phases” for your personal journey. Creating those segments gives clarity about where you’ve been and where you’d like to go. Much like setting quarterly OKRs in a company, you’re setting personal life goals and marking your own progress.
Local Maxima vs. Global Maxima
Sometimes we grab the first seemingly good opportunity that falls in our lap—maybe it pays better, maybe it feels “safe.” But what if it’s only a local maximum? A short-term high can lock you out of bigger, better gains later on. In early-stage startups, founders often learn this lesson: don’t get dazzled by an easy acquihire if it keeps you from building the more ambitious product. Likewise in life, allow a bit of time and reflection before committing to major changes. This is a core theme in “decision-making under uncertainty,” a principle shared by many founders.
Learning vs. Earning
Let’s be honest—there are seasons in life when we’re leaning into deep learning, picking up new skills, and finding direction. Then there are times when the paycheck takes over. But you can get stuck with neither if you aim blindly. Companies scale effectively when they track both personal development (innovative projects, training) and the balance sheet (new revenue, expansion). It’s the same for us: be honest about what you’re optimizing for, and don’t drift aimlessly.
The Secretary Problem
Choosing a path—like picking that next job or city—can feel like a puzzle. Mathematicians call this “the secretary problem,” where you try to guess how long to keep interviewing candidates before settling on the best one. If you jump too soon, you may miss out. If you wait too long, you lose all earlier chances. This perfectly captures the dilemma of finding your right “chapter” in life.
Action Steps
Write Out Your Chapters: Take a blank sheet. Label your past major chapters, then pencil in what you’d like future ones to be.
Beware Quick Fixes: Before hopping into a role or move, ask yourself if it’s a small, safe victory or a bigger, bolder step.
Own Both Learning and Earning: Don’t let either side dominate your entire journey.
Use a Light Framework: Just like a founder sets objectives, do the same with your personal priorities—whether it’s health, relationships, or new skills.
Looking forward is harder than looking back, but that’s where the real game is played. If this reflection resonated with you, odds are it’ll help someone else, too. Share it with your friends and colleagues, and start a conversation about what your next chapter might hold.