Project: Avoid Getting a Real Job
The Story
After leaving Airbnb in 2019, Lenny didn’t rush into his next venture. He used a 6-month exploration period with one guiding philosophy: “do more of what gave me energy, and do less of what sapped me of energy” (Source 1).
He created a two-week sprint system: set 3 work goals and 3 personal goals, email them to 3 friends, then report back at the end of the sprint (Source 1). He called the entire exploration phase “Project: Avoid getting a real job” (Source 1).
He never planned to write full-time. The newsletter was an unplanned outcome (Source 1). Rather than immediately starting a company, he discovered he preferred three activities: writing, angel investing, and advising. He allocated roughly one-third of his time to each (Source 2).
He explicitly avoided becoming a full-time VC, writing a book, or creating a PM training course, despite others suggesting those paths (Source 2). He views the three activities as interconnected, creating beneficial momentum (Source 2).
His financial approach during this period: he read “The Bogleheads’ Guide to Investing” in high school, and his primary investment strategy has always been index funds (Source 1). He recently hired a professional financial advisor, admitting confusion about advanced financial optimization (Source 1).
Lesson for Creators
Most people leaving a high-status job feel pressure to immediately announce their next thing. Lenny resisted. He gave himself permission to explore, built in accountability through friends rather than public announcements, and let the answer emerge over months. The two-week sprint system is a practical tool: short enough to experiment, structured enough to make progress, social enough to maintain momentum. The newsletter wasn’t a strategic bet. It was whatever survived the energy filter.
Related
- The Sabbatical That Killed His Airbnb Career — the clarity that preceded this exploration
- The Medium Post That Launched Everything — the accidental outcome of the exploration