Welcome to Challenge The Work, where we unravel the complex dynamics of modern work culture.
We believe work should be more than just tolerable: it should be meaningful and fulfilling.
In each episode we challenge conventional wisdom and take on the status quo, diving into the root causes of workplace discontent and offering practical actions to help you reshape the way you work.
Join hosts Jules Fedele, venture builder and founder of the Portfolio Career Club, and John Rizzo, organisation architect and founder of Joyous Work. Let’s challenge the work!
In this episode, we confront the shocking reality that 67% of workers have experienced a toxic boss, and unpack why even good people engage in destructive behaviors when the system demands it. We explore how organizational structures create toxicity, share radical approaches like "no dickheads" policies that actually work, and offer powerful post-it note strategies to protect your energy and transform leadership dynamics.
Check out our Substack (https://challengethework.substack.com/p/ep-6-are-office-dckheads-inevitable) where we unpack each post-it note in detail.
Let's challenge the Work!
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
19 Nov 2025
On Job Loss & Grief: The Phenomenal Power Of Identity
In this episode, we unpack why losing your job can trigger genuine grief - and what that reveals about how dangerously we bind our identities to job titles instead of our crafts. We explore how companies like IBM and Unilever are pioneering skills-based approaches that make people recession-proof, and share powerful post-it note strategies to reclaim ownership of your professional identity before it's too late.
Check out our Substack (https://challengethework.substack.com/p/ep-5-on-job-loss-and-grief) where we unpack each post-it note in detail.
Let's challenge the Work!
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
5 Nov 2025
AI Supported Work: Sorting the Gifts from the Grifts
In this episode, we reveal why 86% of workers using AI tools might actually be drowning in more work, not less. We expose how AI productivity can amplify the "work-about-work" epidemic and explore radical approaches from Basecamp's calendar rebellion to creating protected "mission time" for your team. Plus, practical post-it note strategies to harness AI's power without losing your craft or sanity.
Check out our Substack (https://challengethework.substack.com/p/ep-4-ai-supported-work) where we unpack each post-it note in detail
Let's challenge the Work!
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
23 Oct 2025
The Epic Laziness of Forced Return to the Office
In this episode, we expose the massive disconnect between CEOs forcing people back to offices and the 94% of workers who want flexibility - and why this battle is destroying employee satisfaction everywhere. We spotlight innovative approaches from Spotify and LinkedIn that prioritise trust over surveillance, and deliver practical post-it note strategies to transform office time from soul-crushing obligation into craft-deepening opportunity.
Check out our Substack (https://challengethework.substack.com/ep-3-the-epic-laziness-of-forced) where we unpack each post-it note in detail.
Let's challenge the Work!
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
5 Oct 2025
Happy Circle Back Day
In this episode, we expose how "circling back" has become workplace kryptonite - killing momentum and stealing joy from our work. We unpack why this phrase signals deeper organisational dysfunction, share Amazon's six-page memo approach, and offer three powerful post-it note strategies to eliminate endless loops and create real coherence in your team.
Check out our Substack (https://challengethework.substack.com/p/ep-2-happy-circle-back-day) where we unpack each post-it note in detail.
Let's challenge the Work!
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
19 Sept 2025
Dream Jobs
In our debut episode, we explore why people’s dream jobs are all about craft - using skills to create meaningful outcomes - and why modern workplaces make that so hard. We unpack the hidden tax of “work-about-work” and share simple, practical shifts you can try tomorrow to reclaim joy and focus in your work.
Let’s challenge the Work!
- Jules & John
See omnystudio.com/listener (https://omnystudio.com/listener) for privacy information.
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