The Secret to Staying Optimistic (That Nobody Talks About)

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Ever caught yourself saying “everything happens for a reason” when things get tough? Or pushed away negative feelings because “optimistic people stay positive?”

Here’s what Simon suggests instead: let yourself feel bad sometimes.

“I just said, can you stop with all of this, please, and just tell me how you feel?” Simon recalls telling a friend who was forcing positivity during a difficult time. It turns out, true optimism isn’t about forcing a smile—it’s about something much more powerful.

“Optimism is not naive, nor is it blind,” he says. “It is the undying belief that the future is bright.” But here’s the crucial part: that belief can coexist with current struggles, doubts, and difficulties.

The Problem with “Toxic Positivity”

When we try to force ourselves or others to “stay positive,” we’re actually creating more stress. Why? Because we’re not just dealing with the original challenge—we’re also battling the guilt of not feeling positive enough about it.

“A healthy person has all the emotions,” Simon reminds us. “If you get stuck in sadness, that’s a clinical problem. If you get stuck in happiness, that’s not healthy either.”

How to Practice Real Optimism

  1. Make Space for All Emotions: Instead of pushing away negative feelings, acknowledge them. This doesn’t mean wallowing—it means accepting that every emotion has its place in a healthy life.
  2. Double Down on Relationships: “You double down on relationships, double down on friendships,” says Simon. Real optimism isn’t something we achieve alone—it’s something we build together.
  3. Separate Current Reality from Future Possibility: “What I’m talking about is not the absence of stress,” says Simon. “It’s just clarity as you go through that stress.” You can acknowledge today’s challenges while maintaining faith in tomorrow’s possibilities.

Putting It Into Practice

Next time you’re facing a challenge (or supporting someone who is):

Start with Honesty: Allow yourself or others to express genuine feelings without rushing to “fix” them.

Build Connection: Rather than offering solutions, focus on strengthening relationships. Sometimes just being present is more powerful than being positive.

Maintain Perspective: Remember that acknowledging current difficulties doesn’t mean giving up hope for the future. As Simon says, “We can sit in the hell and darkness and struggle now,” while still believing in a brighter tomorrow.

The Power of Real Optimism

This approach might feel counterintuitive at first. After all, we’re often taught that being optimistic means always looking on the bright side. But true optimism is more resilient than that—it’s the ability to face reality while maintaining hope, to acknowledge struggle while believing in possibility.

“Relationships will always outlast everything else,” Simon reminds us. “There’s nothing certain about anything at work, but the strength of those relationships will carry you through.”

By making space for all emotions and focusing on genuine connections, we build an optimism that’s authentic, sustainable, and contagious. It’s not about forcing smiles or finding silver linings—it’s about creating a foundation strong enough to support both our struggles and our hopes.

Because real optimism isn’t about pretending everything is fine. It’s about knowing that even when things aren’t fine, we have the strength, the support, and the capacity to move through it together.

For more insights on building stronger relationships, explore The Optimism Library today. 

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The Optimism Library

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By the end of the program, you’ll be able to:

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You’ll also develop essential human skills you can use every day:

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How You’ll Learn

The program includes four structured units combining independent learning, live training, and practice:

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  • Hone the human skills to guide someone through a WHY Discovery:
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    • Asking effective questions
    • Engaging in active listening

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  • Learn notetaking strategies that will help you facilitate a WHY Discovery session
  • Develop the analytic and collaborative skills you need to help someone identify and articulate their WHY and HOWs

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  • Apply everything you’ve learned to facilitate a full WHY Discovery
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Program Details

Format: 4 live classes + independent learning + group practice

Duration: ~ 8-10  hours per unit (including independent learning and live classes) plus ~5 hours to complete the final exam

Certification Requirements:

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  • Attend and participate in all live sessions 
  • Pass a final exam and performance assessment

Your Support Team

  • Regular updates and reminders
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Program and Participation Terms and Conditions

Our mission is to create a supportive learning environment where we grow together to help others. By joining, you agree to show up in service to one another.

Professional Expectations

  • Attend and participate in ALL live classes in their entirety.
  • Complete ALL assigned online coursework.
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  • Approach the WHY Discovery journey with empathy, integrity, and care for those you serve.

Participant Cancellation and Transfer Policy

  • Cancel up to 10 days before your cohort start date: Full refund.
  • Cancel less than 10 days before: We’re unable to offer a refund at this stage.
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Recording and Photography

  • Participants may not record or screenshot sessions.
  • The Company will record sessions and make them available internally for 30 days.
  • By joining, you understand you may appear on screen and agree that recordings and photos may be used by the Company for program or marketing purposes.

If you prefer not to be included, please contact the team before the first session at [email protected].

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Purchase: $999

The Art of Creating Fiercely Loyal Customers

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Curiosity is essential
                for progress.
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We fully agree, so we like to reward curiosity.
Use code GETCURIOUS for 20% off your next purchase.

A spark is something quite small and, by itself, not very powerful. But a spark has the ability to ignite. An idea is like a spark; alone it is just a set of words, but it too can ignite. A great idea can inspire others to dream bigger. Let us all work together to ignite something greater than ourselves.

Let us all be a Spark of Optimism.