Founder Update 08.10.2025

Soon the supermarkets will replace jack-o-lanterns paraphernalia with advent calendars. 

This is one way to say, “WTF, how is it October?!” and a way for a 37-year-old who still FROTHS an advent calendar, to say bring on 1st of Nov.

I want those frustrating, yet rewarding choccy windows ASAP.

Just a heads up, you’ll start to get regular updates from me (I’ve said it out loud now, so it’s real) about ICTC, mental health tips and relevant shower thoughts.

If you hate my voice or the way I type, DW the unsubscribe button is at the bottom of this email.

My own mental health

Why not start here? I encourage and expect people to speak and be honest about their mental health, and in the spirit of practising what I preach, here’s the latest from over here.

It’s been ~2.5 years since I was made redundant (for the second time) and pushed the chips in to go full time on ICTC to try and make it work. 

Call me naive, but I had no idea how hard it would be to a) start a business and b) make money.

I’m not talking new car, fancy dinners and sourdough from the bakery money. 

I’m just talking about paying bills, quit my second part time job and stop having toasties for dinner type money. 

For the first time since I was 16 there’s no steady income. And that’s taking its toll. 

This is NOT a “poor bugger me, please buy sh#t loads of merch now” email. This is just the reality right now. 

I catch myself comparing to people around me who are buying cars, doing reno’s, going out for brekkie (#1 cause of inflation – heard it here first) and slam the brakes before spiralling into “WTF am I doing?” mode.

Because while it is a grind and there is a lot of unknowns, I love it. I love running It’s Cool To Cry.  

This mental health caper, she’s a big wheel to turn, but thanks to Cool Criers like you, we’ll make this happen! 

Corporate workshops

With October being mental health month, I’ve been able to get some good looks at running workshops for corporate clients.

Check out this screen I got to use!

My hot mental health tip for this week is to stop comparing.

If you use the excuse “someone has it worse” you will NEVER help yourself.

Because someone will always have it worse.

More info on the workshops are available here.

Merch

I just got a call from the ICTC warehouse manager* reminding me of a spicy deal we’re running. 

If people spend $110 they can get FREE shipping and any other piece of ICTC merch for FREE, just by using code JACKSSHOUT at checkout. 

*The warehouse manager is just me with a clip board and the warehouse is my garage. 

Shop the entire ICTC range of merch here.

Upcoming events

Apologies to anyone outside of Melbourne and to anyone that’s not part of the Pickleball cult (yet).

This section might not concern you.

I’m running the very first It’s Cool To Cry Cup – A pickleball tournament that’s making a difference.

Quick deets: 
•    $59 includes: tournament entry, connection and conversation workshop plus heaps more. 
•    29th October, 6:30pm – 9:30pm
•    The Jar Pickleball Club, South Melbourne
•    No experience = no worries, this is for everyone!

Buy your tickets here, this will be an awesome night. Everything has been designed so you leave the night feeling great.

In the pipeline

I’m starting to write a crash course on mental health confidence and conversations. Call it mental health 101, or a mental health transformation.

It’s designed to shift attitudes towards how to think about our own mental health and provide practical tools to improve it.

Why? Because our attitude towards mental health is going from good to great. But our attitude towards our own mental health is stagnant.

If this is something you’re interested in hearing more about, please reply to this email. I’d love to chat. 

In other irrelevant news

It’s “Watering Wednesday” at my house, so I take the indoor plants that I haven’t killed, outside for a shower. Boy they were thirsty this week!

Cheers, thanks for reading and let's make mental health cool.

Jack – Cool Crier and Founder