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Stewart Butterfield: When You Run Out of Ideas, You're Done

By Stewart Butterfield · Leadership · 2 min read

Slack's founder woke up one morning and knew his previous company was dead. The whiteboard of ideas was empty.

Key Points

Good entrepreneurs are told to be resilient — dig in when everyone says quit
But there's a morning when you wake up and know it's over
The signal: you've exhausted all your ideas for fixing the problem
When the whiteboard goes from full to three bad ideas — it's time

I tell people to give up when they're out of ideas about how to make it work.

The Resilience Trap

Stewart Butterfield was stuck. His game, Glitch, had engaged users but a leaky bucket. New users wouldn't stick. He was caught between two narratives.

On one hand: good entrepreneurs are resilient. When everyone says quit, dig in. Prove them wrong. On the other hand: he woke up one morning and couldn't do it anymore. He was the CEO and the chairman. He was certain it wasn't going to work.

"On one hand, good entrepreneurs are resilient. On the other hand, there's a morning when you wake up and say — I can't do this anymore."

The Empty Whiteboard

At first, the team had whiteboards full of ideas. Post-it notes everywhere. They argued about which ones to try first. Months passed. A year. Eighteen months.

One by one, ideas got eliminated. The board went from overflowing to sparse. Eventually three ideas were left — and they were the ones nobody believed in from the start. That's when Butterfield knew.

"At first you can fill up whiteboards with ideas. Then one by one you eliminate them. A year goes by. And you're left with the three ideas you thought were the worst ones to begin with."

The Rule

Butterfield's rule is simple. Give up when you're out of ideas about how to fix the problem. Not when it's hard. Not when people doubt you. When YOU have nothing left to try.

He shut down Glitch. The internal communication tool his team had built to coordinate the game became Slack. The biggest pivot in enterprise software history started with an empty whiteboard.

"That's always when I tell people to give up — when you're out of ideas about how to make it work."