LLenny's Podcast
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EntrepreneurshipLenny Rachitsky

Follow the Pull

Bet your career on the thing you enjoy, are good at, and others value — even if it's not the plan.

Difficulty
Easy
Time to result
~months to results
Steps
3
Confidence
90%

A decision heuristic for choosing what to work on: instead of executing a pre-set plan, notice where you feel an unexplained 'pull' toward an activity, check whether it sits in the rare overlap of enjoy-it / good-at-it / people-value-it, and double down there. Use it when a side project is quietly working but doesn't fit your stated career plan.

Origin

Lenny left Airbnb with a ranked plan (start a company, join a startup as first PM, join a big company as PM, advise). None of it involved writing. He kept writing on the side because 'there's a pull here,' and a conversation with VC friend Lee Jacobs crystallized it: enjoying something AND other people valuing it is a rare Venn diagram worth pursuing. Michelle later adds the missing third circle — that he also enjoyed it — echoing Ikigai.

Core principles

  • 01Follow energy over plans — the thing quietly working may not be on your list.
  • 02The signal is the overlap of three rare circles: you enjoy it, you're good at it, people value it.
  • 03Don't wait for a business model to be obvious; double down on the pull and let the path emerge.

How to run it

  1. 1

    Notice the pull

    Watch for the activity you keep drifting back to on the side even when it isn't the 'sensible' thing — the one you'd do without being told to.

    Pro tip The pull often shows up as something you defend doing despite others telling you it can't make money.

  2. 2

    Test the three-circle overlap

    Confirm the activity sits where you enjoy it, you have some talent for it, and other people visibly value it. All three matter — talent + demand without enjoyment burns out.

    Pro tip Ask a trusted outsider whether people seem to value it; you'll under-count your own signal.

    Watch out Two circles isn't enough — Lenny nearly missed 'I like doing it' as the trigger.

  3. 3

    Double down and follow it forward

    Commit to the pull, keep doing it consistently, and let the monetization/path reveal itself rather than demanding it upfront.

    Watch out The path will look illogical to people who see only your existing skills.

In the wild

Newsletter over startup

Lenny's plan A-D were all startup/PM roles. He kept writing 'things I learned and things I wanted to share' on the side despite Michelle questioning why, because he felt a pull. He followed it into the newsletter.

1.2M subscribers and a top-10 tech podcast — an outcome nobody, including him, predicted.

Michelle's children's book

Michelle set out to write 'charts for new parents' in the front of a notebook, but kept feeling pulled toward a rhyming kids' book. She flipped to the back of the notebook and followed that instead.

That pulled-toward book became Charts for Babies, the one she actually finished and published.

Common mistakes

Demanding the business model before you start

Lenny pursued the newsletter with no clear way to make money — 'maybe there's a way to make money in the future.' Insisting on a proven model first would have killed it.

Counting only talent and demand

The 'good at it + people like it' pair looks compelling but omits enjoyment, which is what sustains the weekly grind.

Is it for you?

Best for

Operators and creators with a stable career plan who have a side project that's quietly working but doesn't 'fit'.

Not ideal for

Situations needing near-term income certainty, or people who confuse novelty-chasing with a genuine sustained pull.

From the transcript

I don't know. It seems like there's a pull here, so I'm just going to keep doing this.

06:30

you seem to be enjoying it. People seem to be liking it. Which is very rare, that Venn diagram of things.

08:00

It's kind of this like little journey that I just followed pull that was starting to work.

07:30

another example of just following pull and not just doing the thing that you're doing

26:30

From the episode

How I built a 1M+ subscriber newsletter and top 10 tech podcast

Lenny Rachitsky