What if success wasn't the reward for grinding through work—but the result of actually enjoying it?

In this candid and deeply insightful episode, multi-time founder and former Airbnb leader Jason Silver joins Alice to unpack the often backwards narratives we hold about work, ambition, and rejection.

Jason shares the raw story of crashing his startup—and the surprising way that failure led to a life-changing opportunity at Airbnb. He also dives into the neuroscience behind why so many people regret changing jobs, what "hedonic adaptation" has to do with your career dissatisfaction, and how he redefined productivity after a personal tragedy.

You’ll hear:

• Why Jason believes enjoyment is a practice, not a perk

• How he almost got fired after presenting the “perfect” plan to Airbnb leadership

• A dead-simple question that helped him 9x his results

• The personal loss that transformed how he approached work and life

• Practical frameworks for finding more energy, meaning, and satisfaction in your current job

This is an episode about failure, but also about designing a working life you don’t need to escape from.

Chapters:

00:50 Intro
02:44 Why quitting your job doesn’t make you happier
06:26 Hedonic adaptation at work
09:22 The difference between fun and enjoyment
13:34 Doing the same task differently
19:45 The iPhone list exercise
28:00 The 10x Airbnb challenge
35:57 What would need to be true?
41:46 Defining rejection
43:52 Crashing a startup
52:24 The grief that changed everything
59:51 How Jason has changed
1:03:13 Advice to enjoy growing a podcast

Resources & Links:

• Jason’s website: thejasonsilver.com

• Jason’s book: Your Grass Is Greener – yourgrassisgreener.com

• Follow Jason on LinkedIn: Jason Silver