Serendipity and Curiosity

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

Gokul Rajaram
Picking where to work, hiring, investing, and product development

Serendipity and Curiosity

"A lesson for me I realized is that it's very important to do a core job really well at any company, but it's equally important to have curiosity and be open to serendipity... Many opportunities don't come linearly just working in your job and making sure you get promoted. That's not how great careers are built." - Gokul Rajaram

What It Is

Serendipity and Curiosity is a career philosophy: the biggest opportunities come not from linear career progression but from being curious about what's happening around you, building relationships across your company, and being ready to seize unexpected opportunities when they appear.

Gokul discovered this when he accidentally found the team that became Google AdSense by walking around the office at 6pm and asking people what they were working on. That single act of curiosity - becoming a part-time PM for a project that wasn't his job - shaped his entire career.

How It Works

The Google AdSense Story

At Google in 2003, Gokul was working on syndication:

  1. He stayed late and walked around - At 6pm when others went home
  2. He asked what people were working on - Found engineers building a new ads product
  3. He offered to help - "Can I be your PM?" They said yes
  4. He worked nights and weekends - Kept his day job, added the new project
  5. Within 3 months - The project grew enough that his boss moved him over full-time
  6. Result - That project became Google AdSense

The Square Story

Gokul informally advised a company that was later acquired by Square:

  • He helped them with no equity or formal agreement
  • The founder mentioned him to Jack Dorsey as one of the best product people he knew
  • Square reached out as a result
  • This serendipitous connection led to his next role

Key Principles

1. Do Your Core Job Well:

  • Serendipity doesn't replace excellence in your current role
  • You need credibility to have people trust you with new opportunities

2. Be Curious About What Others Are Doing:

  • Walk around (or Zoom equivalent)
  • Ask people about their projects
  • Build relationships across the company

3. Be Ready to Jump:

  • When you see something interesting, offer to help
  • Don't wait for permission or formal assignments
  • Add value before asking for anything

4. Pay It Forward:

  • Help people without expecting immediate return
  • Build a reservoir of goodwill
  • Your help will come back in unexpected ways

How to Apply It

  1. Schedule exploration time - Block time to learn what's happening across your company

  2. Be genuinely curious - Ask questions because you want to learn, not to network

  3. Offer to help - When you find interesting projects, ask how you can contribute

  4. Don't over-optimize - Some of the best opportunities come from things you can't predict

  5. Build broad relationships - Know people doing great work so they'll want you on their teams

  6. Take inbounds from smart people - When interesting people reach out, respond

When to Use It

  • Throughout your career, not just during job searches
  • When feeling stuck in your current role
  • When your company is growing and has new initiatives
  • When approached by people working on interesting problems

Remote Work Adaptation

Gokul acknowledges that Zoom makes this harder, but the principle remains:

  • Join optional Slack channels
  • Attend company-wide meetings and ask questions
  • Have coffee chats with people outside your team
  • Be active in internal forums and discussions

The Compound Effect

These small acts of curiosity and relationship-building compound:

"You build up a reservoir of goodwill that comes back to help you in different ways."

Paying it forward, helping others, and staying curious creates options you can't predict but that consistently pay off over time.

Source

  • Guest: Gokul Rajaram
  • Episode: "Picking where to work, hiring, investing, and product development"
  • Key Discussion: (00:05:09) - How curiosity led to Google AdSense and career philosophy
  • YouTube: Watch on YouTube

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