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“Keep your face always toward the sunshine and shadows will fall behind you.” — Walt Whitman
The $2.1 Million Question
March 2020. Airbnb’s bookings collapse 80%.
CEO Brian Chesky faces a choice: focus on the crisis or find the opening.
They pivoted to longer stays, local getaways, work from anywhere.
By 2021, revenue hit $6 billion — their best year ever.
The insight:
The Bright Side is more than toxic positivity or blind optimism.
It is disciplined hope.
It is the disciplined practice of finding possibility.
And it is a leader’s greatest strategic advantage.
Perspective is contagious.
When you choose the Bright Side, others don’t just follow — they innovate.
• When adversity hits, what’s my first thought — the risk or the possibility?
• How many problems did I reframe into opportunities for my team this week?
1. Optimistic leaders don’t deny reality. They mine it for potential. (Teams with hopeful framing see 42% more creativity and 25% less turnover.)
2. Your stance becomes your team’s default. Model anxiety → anxious teams. Model possibility → innovative teams.
3. While others freeze in uncertainty, Bright Side leaders accelerate.
1. Start your next meeting with: “What’s one thing that’s working better than expected?”
2. Before tackling a problem, spend 2 minutes naming what’s already working.
3. Replace “We have to” with “We get to.” Notice the energy shift.
4. Text one team member specific appreciation for their work this week.
The Bright Side is more than optimism.
It is a leadership stance.
When you model hope, your team learns to respond with courage, not fear.
And here’s the real power: the Bright Side multiplies when you share it.
Forward this to a teammate. Mention it in your next one on one. Spark a conversation.
Because in a world full of pessimistic predictions, Bright Side leaders don’t just stand out.
They shape what’s next.
Until next time, keep looking for the Bright Side.
Stay relentlessly optimistic,
Tim
Because the Bright Side is not a place you find.
It is a choice you make.
The three minute practice that separates overwhelmed leaders from clear minded ones.
It is not meditation, journaling, or exercise.
And 97% of leaders who try it report feeling more in control within their first week.
About the Newsletter
The Tim Crowly Newsletter is one of the most insightful newsletters on the web. Thousands of readers subscribe every week. Each issue brings you 3 practical ideas from Tim Crowly, 2 thought-provoking quotes from great minds, and 1 powerful question for reflection.
