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Give Your Team the Skills They Actually Need

The Optimism Library

Simon's proven leadership and communication methods, insights, and frameworks. All in one platform, for one price.

  • Help your managers lead with real confidence (not the fake-it-till-you-make-it kind)
  • Equip your people with the skills to handle difficult conversations instead of avoiding them
  • Build the kind of psychological safety where people actually speak up and work together
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4.9/5 rating

Give Your Team the Skills They Actually Need

The Optimism Library

Simon's proven leadership and communication methods, insights, and frameworks.

All in one place, for one price.

Buy Now
Invoice Now
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4.9/5 rating

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The office politics here are absolutely toxic

I’m drowning in back-to-back meetings that accomplish nothing

My direct reports don’t respect me and it shows

I got passed over for the promotion again and nobody will tell me why

Jake keeps taking credit for my work in front of our boss

I have no idea what my boss actually wants from me

People are gossiping about me behind my back

My manager micromanages every single decision I make

Everyone’s quiet in team meetings and I have no idea what they’re thinking

This team has zero trust and everyone’s covering their backs

The priorities here change every week and I look incompetent

My coworker sabotages me and HR won’t do anything

I’m completely burned out but can’t say anything or I’ll look weak

People say yes to my face then do whatever they want

My boss throws me under the bus in front of clients

I can’t give honest feedback without someone having a meltdown

People quit without giving real reasons and I feel like a failure

My boss plays favorites and I’m clearly not one of them

Every decision I make gets second-guessed by someone

Nobody collaborates—everyone protects their turf

I’m supposed to lead but I have zero authority

I dread coming to work and it’s affecting my health

My boss is avoiding me

Does this sound like your office?

Does this sound like your office?

We might have something for that

These are just some of the skills your team will learn with Optimism Library access.

Relationship Building

  • Handling conflict before it explodes
  • Navigating office drama without getting sucked in
  • How to build psychological safety
  • Building trust when everyone's been burned

Personal Resilience

  • Finding meaning in your job
  • Speaking up when you usually stay quiet
  • What to say when you're overwhelmed
  • Staying sane during chaos

Communication Mastery

  • How to present ideas that inspire action
  • How to weave thoughts into stories
  • Really listening instead of waiting to talk
  • Giving feedback that won't crush souls

Leadership Development

  • Getting people excited about work
  • Making decisions when nothing's clear
  • How run meetings people don't hate
  • Leading when everything's falling apart
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How your teams will actually use this

Kill Time Productively

It’s like Netflix, but for work! 

Solve Workplace Problems As Soon As They Pop Up

Your people can instantly search for practical solutions like "Your Coworker Stole Your Idea? Here's Simon's 3-Step Response" or "The Words that Kill Trust (and What to Say Instead)."

Continuous Learning for Those More Complex Subjects

Use ready-made playlists for common challenges: Difficult Conversations, Trust & Psychological Safety, Leading Through Change, and Conflict Resolution, to name a few.

Make Training Stick

Discussion guides help teams process what they've learned together, while live Q&As with Simon let them ask about their specific situations.

Here's what your team actually gets

Simon's Complete Course Library

  • The Art of Presenting
  • How to Be a Leader People Actually Trust (and Maybe Even Love)
  • A Navy SEAL's Guide to High Performance at Work

250+ Bite-Sized Solutions for Real Workplace Challenges

  • Practical communication tools and strategies
  • Battle-tested leadership advice
  • Personal resilience techniques that actually work

Direct Access to Simon + World-Class Expert Sessions

  • Quarterly live Zoom Q&As with Simon himself
  • Monthly workshops led by top experts like Will Guidara, author of Unreasonable Hospitality
  • Deep dives into innovation, workplace connections, change management, and more

Team-Building Programs Your People Will Actually Enjoy

  • Unleash Your Infinite Mindset (led by Simon)
  • The Art of Presenting (led by Simon)
  • The Art of Building Fiercely Loyal Customers (led by Will Guidara)

Daily Fuel to Sustain Long-Term Growth

  • Personal pep talks from Simon
  • Quick-hit reads and actionable workbooks
  • Curated learning playlists across dozens of topics

Pricing

Starting at $167 per person per year 

Bigger teams, bigger savings

Table header
1-25 people:$299/person
26-50 people:$224/person (25% off)
51-100 people:$167/person (44% off)
101+ people:Contact us for enterprise pricing

Pay with Credit Card

Simply click here, choose your seats, and add your team's information within the dashboard after purchase.

Pay with Credit Card

Invoice Now 

Fill out our short form and we’ll send you an invoice. Once paid, we’ll email everything you need to get started.

Invoice Now

Contact Sales

Reach out to chat with a member of our team.

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$249 per person per year 

(That’s like 5 phone chargers!)

Pay How You Want

Pay with Credit Card
Invoice Now
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Optimism Library Reviews

Denise B.
Verified Buyer
It is wonderful to have a successful professional freely share information to help others grow—for their sakes to be a better leader. Not primarily to make a buck. Making a difference in s
....
Read full review
Nuria R.
Verified Buyer
I loved it. Lots of little tidbits that can be applied holistically or individually.
Benjamin K.
Verified Buyer
Great deal for money and moreover great talent delivering the content.
Andrea B.
Verified Buyer
I love having the resource to browse and use as needed as well as to help as I coach my staff through situations they find themselves in.
Kathleen C.
Verified Buyer
I love attending the online video classes. I’ve learned many different new aspects of leadership. I enjoy hearing people’s points of view on the books and I can stop and come back when m
Heidi Y.
Verified Buyer
Well worth it, I am trying to work through as many lessons as I can, but will need another month at least.
James M.
Verified Buyer
I’m inspired!!!!
Sarah S.
Verified Buyer
I’ve gone through several courses over the past two weeks and I already am seeing a difference within our team! I’ve loved how my outlook has shifted and I’ve really been able to step
....
Read full review
Sabine G.
Verified Buyer
So far, I am very amazed by the content of the library. As I am working in the field of HR for 25 years, I am trying to figure out how applicable the content is and I have just started to ge
....
Read full review
Tina K.
Verified Buyer
Absolutely fantastic. Delivery was excellent. Docs provided are very useful tools for communicating feedback for any instance at any level. Highly recommend!!!
Herman P.
Verified Buyer
Love the content. Although I expected to see Simon on a few more of the videos 🙏…
Some are like webinars and could be arranged better. Remove non-essential info and questions fro
Steven B.
Verified Buyer
I absolutely love it. Amazing. It feels like it’s too cheap to be honest, because the amount of value around all of the things that are foundational to my life, my business, my relationshi
....
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Jodi R.
Verified Buyer
I like the video content in the optimism library but it would be incredibly helpful to be able to also access the slide deck and handouts mentioned in each recorded webinar. The downloadable
....
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FAQs

Pretty great actually—thanks so much for asking! We hope you’re having a great day as well.

Don’t worry, we’ve got you!

1. Head here to reset your password
2. Enter your email address (the one you used at checkout)
3. Check your email inbox for further instructions

It’s as easy as 1, 2, 3:
1. Sign in to your account
2. Click on My Learning Dashboard
3. Scroll down to the “My Optimism Library” section and select a video!

You’ll have access as long as you’re subscribed. 

If you decide The Optimism Library isn’t right for you, you can get a full refund within 14 days of purchase. Simply contact us here—no questions asked.

You can cancel your subscription at any time to prevent automatic renewal for the following year. Cancellation can be done through your account settings.

You bet! Find Simon’s wisdom nuggets in the “Learn with Simon” section of the Library and you can access all of his bestselling courses, including The Art of Presenting.

But that’s not all—your subscription now includes those exciting new quarterly live Q&A sessions where you can interact with Simon directly! And when Simon’s catching his breath, our world-leading experts and Optimist Instructors step in to deliver those monthly live sessions and other fantastic content. It’s like having the whole optimism dream team in your corner!

Most of the content in The Optimism Library consists of on-demand recordings that you can access anytime. However, your subscription now includes new quarterly live Q&A sessions with Simon and monthly sessions with leadership experts over Zoom. We’ll notify you about upcoming dates for these live events, and you can always find the schedule in your dashboard.

For additional live experiences with your team or company, reach out to our B2B experiences team at https://business.simonsinek.com/contact-us/.

Great news! We’ve gone all in! Your subscription now includes Simon’s complete course collection. That means everything from The Art of Presenting to Find Your WHY is now at your fingertips—no separate purchases needed. Plus, we’re still adding fresh content every month to our library of 125+ existing lessons. Consider this your all-access pass to the world of optimistic leadership!

Yes! We recommend only doing so over Wi-Fi, unless you have an unlimited data plan.

You can buy up to 50 subscriptions through our website, or you can request a bulk order by writing us at [email protected]. 

You can use the Optimism Library Contact Form and we’ll get back to you as soon as we can!

Once you’re logged into your dashboard, you’ll find the schedule for upcoming live sessions, including Simon’s quarterly Q&As. We’ll also send email notifications before each session with the Zoom link and details so that you can RSVP. Can’t make a live session? Don’t worry! Recordings will be available in your library afterward.

Absolutely! That’s what makes these sessions special. You can submit questions in advance or ask them live during the Q&A portion. It’s your chance to get Simon’s perspective on the problems you’re trying to solve and the dreams you wish to achieve. 

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Unwavering customer support
Best-in-class training content
Trusted globally
Unwavering customer support
Best-in-class training content
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