In this deeply personal and full-circle episode of ClockingOut Jolly Jack-O (aka Will Craig) returns exactly one year after his first appearance this time with no mask more wisdom and a whole lot to share.

We dive into everything from grief and growth to creativity and community. Jolly opens up about the loss of his brother, struggles with ADHD, raising his son as a single dad and the emotional weight of chasing a dream while juggling teaching, coaching and content creation. He shares how the VeeFriends community helped him find purpose, confidence and lifelong friendships.

This episode is about real life. No fluff. Just raw honest storytelling from someone who's lived it and is still living it.

If you're feeling stuck, alone or like no one understands the path you’re on... this one is for you.

0:00:00 – Intro — Full circle moment: Jolly returns one year later

0:02:00 – How Jolly Jack-O got started in the community wearing a mask

0:07:00 – Mental shifts, personal growth, and finding his vision

0:10:00 – Balancing teaching, content, parenting, and creative projects

0:13:00 – Opening up: grief, loss, and healing through creativity

0:24:00 – Navigating co-parenting and staying positive in the storm

0:33:00 – All the hats Jolly wears: creator, coach, teacher, dad

0:36:00 – Scuba Steve asks: Are you doing too much at once?

0:40:00 – Adult ADHD, medication, and finding better self-balance

0:42:00 – Why Jolly creates even when it’s hard — doing it for his son

0:50:00 – Do your friends understand your hustle? Does it matter?

0:54:00 – What “Always Stay Jolly” means now vs. when it began

1:00:00 – Final messages: Jump. Do it. Don’t live with regret

1:05:00 – Scuba asks: If your life were a movie, what would we yell?

1:10:00 – The National, community meetups, and legacy conversations

1:15:00 – Closing words, POAP reminders, and future collabs

Follow Will AKA ( JollyJack-O🎃)

Instagram- @jolly_jacko

X - @jolly_jackoVF

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