Welcome to The Optimism Library

We're so happy that you're here.

This dashboard has everything you need to Grow@Work:

  • Signature Courses and Playlists
  • Monthly LIVE Events
  • 290+ Lessons and Counting
Shape

The Art of Presenting

Learn the Basics. Inspire the Masses.

Get tips and tricks on wowing the crowd straight from Simon with our best-selling course. Now available for all members of The Optimism Library. 

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LIVE with Simon: The Plight of the Middle Manager

As a member, you are invited to join our next LIVE Q&A with Simon on October 7th at 2pm ET for a special 90 minute session. See you there!

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Grow@Work Playlists

Don't know where to start? Look no further!
Each playlist below is a customized journey through our best lessons to help you solve a specific workplace problem.

Meeting Starters
Meeting Starters
Simon's Storytelling Secrets
Simon's Storytelling Secrets
From Middle Manager to Leader
From Middle Manager to Leader
Lead Through Uncertainty & Change
Lead Through Uncertainty & Change
Relationships@Work
Relationships@Work
Build a Better Culture
Build a Better Culture
Get the Promotion
Get the Promotion
Boost Your Confidence
Boost Your Confidence
Find a Job You Love
Find a Job You Love
Coachable Moments from Simon
Coachable Moments from Simon

Conversations with Experts

Supercharge your communication and leadership skills alongside Simon and Library members as they discover new insights in conversations with experts.

a recording from a LIVE Q&A that took place on Sept 4 2025

A recording of a Live conversation that took place on August 11th

A recording of a LIVE Q&A that took place on July 8th with Simon.

A recording of a Live conversation recorded on June 17th 2025.

A recording of Sara's LIVE Q&A, which took place on May 29th, 2025.

A recording from Zach's Live Q&A on May 8, 2025.

A recording from Simon's Live Q&A on April 22nd, 2025.

Simon and Engagement Expert Juliet Funt discuss how to reset your work/life balance.

Simon and Leadership Expert Kristen Hadeed discuss how to approach the challenges of leading Gen Z.

Learn how to listen like a leader with Simon and Executive Coach Andrea Garfield.

The learning continues! Here's part 2 to Simon's conversation on Active Listening with Executive Coach Andrea Garfield.

Hear from Simon and Retired Navy SEAL Commander Rich Diviney on how to build a high-performing team with trust.

Join Simon and The Millennial Therapist Dr Sara Kuburic as they talk about effectively communicating emotions at work.

Our Signature Courses

Expand your leadership. Improve your mindset. Live your purpose.

Our Most Popular Course

Our Most Popular Course

Simon teaches everything you need to know about preparing and giving presentations — no matter how small or large the audience.
Be The Leader You Wish You Had

Be The Leader You Wish You Had

Simon and Zach Mercurio speak on how to care for your team and create a culture of trust and passion.
Play to Stay in The Game

Play to Stay in The Game

Simon based this course on his best-selling book, The Infinite Game. Learn how to be more agile, more courageous, and more successful.

Make Connecting at Work Easier

Make Connecting at Work Easier

What do all your conflicts have in common? You. Dr. Sara Kuburic is an existential psychotherapist here to improve your self-awareness, emotional control, and workplace relationships.
Be More Unreasonable

Be More Unreasonable

Will Guidara ran the #1 restaurant in the world. His best-selling book, Unreasonable Hospitality, is the foundation of this course on how to run an industry-leading business and give people experiences they'll never forget.
Build a More Trusting Team

Build a More Trusting Team

Simon and retired Navy SEAL Commander Rich Diviney explain the secrets behind high performance and building trust.
Live with Purpose, On Purpose

Live with Purpose, On Purpose

Before you can start with WHY, you need to know your WHY. Have Simon guide you through the process of discovering your WHY in this course.