Never As Good/Bad As You Think

Stay even-keeled because extreme emotions distort judgment and stress your team

Brian Tolkin
Lessons from scaling Uber and Opendoor

Never As Good/Bad As You Think

"When you reflect the stress onto your teams, everybody tenses up and tightens up. And so it counterintuitively doesn't produce better outcomes... You're never as good as you think you are. You're never as bad as you think you are." - Brian Tolkin

What It Is

Never As Good/Bad As You Think is a mantra for maintaining emotional equilibrium during the highs and lows of building products and companies. The core insight is twofold:

  1. Emotional extremes distort judgment - When you're riding high, you underestimate risks. When you're in crisis, you overestimate doom. Neither state produces good decisions.

  2. Leader emotions cascade to teams - When leaders reflect stress onto their teams, everyone tenses up. Counterintuitively, this produces worse outcomes, not better. Calm leaders enable calm teams who can think clearly.

The framework serves as both a personal regulation tool and a leadership principle. Use it to manage your own emotional swings and to model the even-keeled demeanor that enables your team to perform at their best.

How It Works

The Emotional Distortion Pattern:

High Points:

  • Success feels bigger than it is
  • Risks seem smaller
  • Overconfidence creeps in
  • You think you've "figured it out"

Low Points:

  • Failures feel catastrophic
  • Everything seems broken
  • Panic sets in
  • You think it's all over

Reality:

  • Always somewhere in between
  • Cycles pass
  • Both success and failure compound
  • Emotional reactions are rarely proportionate

The Team Cascade Effect:

When leaders show stress:

  • Team members tense up
  • Psychological safety decreases
  • Creative thinking shuts down
  • Defensive behavior increases
  • Decision quality decreases

When leaders stay calm:

  • Team members can think clearly
  • Problems get solved rationally
  • People take appropriate risks
  • Better decisions get made
  • Crises resolve faster

How to Apply It

  1. Develop awareness mantras - Repeat during emotional extremes:

    • "I'm never as good as I think I am"
    • "I'm never as bad as I think I am"
    • "This feeling will pass"
    • "I've been here before"

  2. Create physical space - Before reacting:

    • Take a breath
    • Walk around the block
    • Sleep on it if possible
    • Talk to a trusted peer

  3. Study other journeys - Build perspective through:

    • Biographies of entrepreneurs
    • Podcasts like Founders Podcast
    • Conversations with experienced leaders
    • Your own past experiences

  4. Watch your transmission - Monitor how you:

    • Share news with your team
    • React in public meetings
    • Communicate during crises
    • Celebrate during wins

  5. Practice in low stakes - Build the muscle:

    • Small frustrations are training
    • Minor wins are training
    • Build habits before crises hit
    • Reflect after emotional moments

When to Use It

  • During product launches (especially stressful ones)
  • When competitors make moves
  • After big wins or losses
  • During organizational crises
  • When metrics spike or crash
  • Before communicating to your team

Examples

Brian Tolkin - uberPOOL China Launch:

  • 30 minutes of sleep before go-live
  • System not working at 5:00 PM day before
  • Stayed calm, worked the problem
  • Got everything working at 5:30 AM
  • Launched successfully
  • Best pancakes he ever had afterward

Brian Tolkin - Opendoor COVID:

  • Core business stopped (can't enter homes)
  • Real estate data from China looked catastrophic
  • Could have panicked
  • Instead: paused, virtualized the process
  • Came out the other side stronger
  • Now a fond memory of a stressful time

How to Build This Skill

Experience-based:

  • Go through stressful situations
  • Reflect afterward on what helped
  • Build confidence that cycles pass
  • Develop pattern recognition

Story-based:

  • Read biographies of entrepreneurs
  • Listen to Founders Podcast
  • Learn from others' journeys
  • See that nonlinear paths are normal

Practice-based:

  • Start with small situations
  • Notice your emotional reactions
  • Practice the pause
  • Build new habits

Source

  • Guest: Brian Tolkin
  • Episode: "Lessons from scaling Uber and Opendoor"
  • Key Discussion: (00:53:18) - Staying calm under pressure
  • YouTube: Watch on YouTube

Related Frameworks

Back to Leadership