It's Cool To Cry Workshop

97.6% left with practical tools to have mental health conversations

You're aware of mental health. Now give your team the tools to do something about it.

A practical, 60-minute workshop, in-person or online that gives your team the mindset shift and tools to speak up about their mental health early. No clinical jargon. No box-ticking. Just real conversations that stick.

Book a free 20-minute discovery call. Let's see if this is right for your team.

Impact snapshot

97.6%

Left with practical tools to use

99.2%

Would recommend the workshop

95.2%

More likely to speak up about their mental health

100%

More confident mental health is normal

Based on post-workshop participant survey (n=140, immediately post-session)

Most businesses don't know where to start.

"Mental health is on our agenda, but we're not sure where to start."
"We've had someone struggle, we want to help and I don't want to be caught off guard again."
"We want to do something real, not just tick a box."
"We're a good team. I just want people to feel like they can actually speak up."

How is this workshop different?

Others	It's Cool To Cry
"Are you OK?" and checking in on others.	"I'm not OK, can you listen?" checking in and speaking up for yourself.
Awareness only. Nothing practical to use after.	Practical tools and language from day one.
Clinical, formal, feels like a compliance exercise.	Interactive, relatable, feels like a regular chat.
Forgotten.	Talked about weeks later with tools being used at work and at home.

What clients are saying

Johns Lyng Group

"Our teams have embraced Jack’s golden nuggets which have translated into more transparent staff discussions and engagement. Within 24 hours of Jack's workshop we had already scheduled another session."
Darlene Pearson, HR Director

Boroondara Council

"Rather than just a ‘Mental Health 101', his workshop provided participants with tools they can walk away with and how to engage in meaningful conversations about their wellbeing."
Natasha Pool, Mental Health & Wellbeing Project Officer

Kat The Label

"Jack's approachable and relatable delivery made mental health conversations feel accessible and comfortable."
Kate Nixon, Founder

Ready Media Group

This workshop helps build the culture we're creating. Recommended for anyone wanting something practical, not preachy.
Will Pickering - COO

Vitality Brands

"Your casual, human touch made the team feel right at home, you nailed a conversation that can be uncomfortable for many."
Carly Toth, GM of People & Culture

Mind The Change Inc.

"The workshop opened so many doors and conversations around our work and how we operate as a team. Very practical and useful."
Althea Gordon, Artistic Director

I've also worked with

"What you'll get" / Company benefits

Stop guessing who's struggling Most workplace mental health systems require managers to mind-read. After this workshop, your team raises their hand themselves before things become a problem, and before the high performer is already out the door.
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What they'll walk away with

Participant takeaways

"Finally made my mind up about seeking help."
"It's okay to share your thoughts and feelings, no matter if they're not heavy enough. Your feelings are always relevant."
"Mental health is normal. A problem shared can mean a problem reduced."
"How important it is to actively listen, and the fact you can't solve everyone's problems — nor should you try to."

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Clinical credibility

All workshop content has been reviewed by

Dr Jake Kraska - Clinical, Educational & Developmental Psychologist

Fletcher Curnow - Community
Psychologist

Clinical testimonies

"Jack's lived experience provides an impactful foundation to help normalise difficult conversations and he has practical strategies too."
Sabina Reed, Psychologist

"A powerful, human workshop that turns awareness into action."
— Debbie Dobbie, Organisational Psychologist

Workshop Details

Duration: ~60 minutes
Format: In-person or online
Group size: 5 to 100+
Location: Australia-wide (Jack is Melbourne based)
Includes: Workshop facilitation, prep, 5 ICTC tees, post-workshop reinforcement emails

Before every workshop, Jack confirms your organisation's internal support pathways — EAP, MHFA contacts, or wellbeing leads — so participants always know where to go if the conversation brings something up. Facilitating these sessions since [YEAR], Jack is experienced at holding space for difficult moments with care and without drama. Your team is in good hands.

About Jack

I created It's Cool To Cry after losing people close to me who never felt able to speak up. My work focuses on giving everyone the confidence, language and tools to ask for help early, before things become overwhelming.

In the room

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FAQs

Jack is a trained facilitator, not a clinician or mental health professional. This workshop is not therapy or clinical intervention. It's a capability-building session that gives your team practical tools and language to have better mental health conversations. All workshop content has been reviewed by Dr Jake Kraska (Clinical, Educational & Developmental Psychologist) and Fletcher Curnow (Community Psychologist) for clinical accuracy and psychological safety. Jack's lived experience is the foundation of the work and evidence based practices and tools are the foundations of the workshop.

This is something Jack prepares for with every organisation before the session. Before delivery, your internal support pathways, EAP contacts, MHFA-trained staff, or wellbeing leads are confirmed and communicated to Jack. These are reiterated at the close of the workshop, so every participant knows exactly where to go if the conversation brings something up. Jack is experienced at holding space for difficult moments with care, without drama, and without the session derailing. While it isn’t the intention of the workshop, emotional responses can happen.

EAP is a reactive service it's there when someone is already struggling. R U OK? Day is an awareness campaign that asks people to check in on others. This workshop is different on both counts. It's proactive and skills-based, and it focuses on the harder side of the conversation teaching your team to speak up about their own mental health, not just ask about someone else's. Most people know they should reach out when they're struggling. This workshop gives them the confidence, language, and tools to actually do it before things reach crisis point.

Yes. The workshop runs just as effectively online as it does in person. Jack has delivered it virtually to distributed teams across Australia and the format is specifically designed for engagement, not a passive webinar, but an interactive session where participants contribute, reflect, and connect with each other. The only requirement is that people can see and hear each other. If your team is split across locations, we can also discuss running multiple smaller sessions to keep group sizes manageable.

Immediately after the workshop a follow up safety email is sent. This email includes resources for participants to find support if they need. Plus, every workshop includes an opt-in post-workshop reinforcement email series for participants. They’re short, practical emails that revisit the tools covered in the session and help them apply what they learned over the weeks that follow. Research shows that a single session, no matter how good, fades without reinforcement. The email series is designed to keep the conversation alive. Multi-workshop packages are also available for teams that want to go deeper, build on the foundations, or run sessions with different groups across the organisation.

When you book a discovery call, Jack will send you an impact summary or a proposal you can share with your manager, finance lead, or CEO. It covers outcomes, proof, client names, and the business case in one page.