How to be Great at Worrying

How to be Great at Worrying

From Startup Therapy by Startups.com

May 25, 2026 · 36 min · Episode 333

About this episode

The episode discusses how founders can manage their worries and anxiety to make productive decisions instead of spiraling into stress.

Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant vigilance can turn into fear dressed up as responsibility—endless rumination that produces stress, not decisions. Will shares decades of 3:00 AM worry cycles, the superstition that anxiety prevents disaster, and how even vacations get hijacked by disaster simulations (including getting hacked on the way to Comic-Con). They draw a line between real thinking that creates options and looping that creates suffering, then discuss practical replacements: box breathing to fall back asleep, gratitude to reset perspective, and self-talk that puts the “experienced founder” back in charge. The goal isn’t to stop worrying, but to channel that energy into small, solvable actions instead of spirals. What to listen for: 00:41 Learning to Worry 01:21 Walk the Lot Mindset 03:28 Fear as Responsibility 05:07 Paranoia and 3AM Ceilings 06:25 Anxiety Superstition Loop 08:18 Vacation Disaster Mode 10:21 Thinking vs Rumination 13:10 Breathwork Replacement 14:14 Milestones Won't Fix It 15:53 Experience Adds Knives 18:47 Fear Makes It Worse 19:39 Worry As…

People in this episode

Guest: Will

Topics covered

  • worry
  • founders
  • anxiety
  • stress management
  • decision making
  • self-talk

Keywords

  • worrying
  • startup
  • anxiety
  • breathwork
  • rumination
  • self-talk
  • stress

Mentioned in this episode

Organizations: Startups.com

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