What we covered in our chat
In this episode of the Well Workplaces Podcast, I sat down with Cherie Clonan, founder and CEO of The Digital Picnic, to explore what ambition looks like when we stop measuring success purely through growth, output and achievement. As the leader of an award-winning agency recognised for its people-first approach, Cherie brings a refreshing perspective on performance, leadership and building workplaces where people can thrive without sacrificing their wellbeing.
Redefining what success looks like
One of the strongest themes throughout our conversation was the idea that many of us have inherited a very narrow definition of success. Early in her career, like many founders, Cherie was driven by enthusiasm, optimism and the desire to build something meaningful. But over time, her definition of ambition evolved.
Rather than chasing constant growth, she now measures success through things that many workplaces overlook: having time to drive her children to school, being present for life's important moments and creating sustainable ways of working. Her message was simple but powerful: if success comes at the expense of health, relationships and recovery, it may be worth reconsidering how we define it.
The performance paradox
A key discussion centred on Cherie's white paper, The Performance Paradox. Through conversations with professionals across industries, she noticed a troubling pattern: organisations celebrating strong results while employees were exhausted, overwhelmed and needing months to recover from sustained periods of pressure.
For HR, health and wellbeing, and health and safety leaders, this raises an important question: when productivity increases through automation or new technology, what do organisations do with the additional capacity? Cherie challenged leaders to think differently. Rather than filling every efficiency gain with more work, what if some of that time was reinvested into learning, flexibility, development or recovery?
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Creating inclusive workplaces
Another standout part of our conversation was Cherie's approach to neuro-inclusive workplace design. Drawing on both lived experience and professional practice, she shared how simple accommodations can create enormous benefits for employees.
From providing interview questions in advance to offering greater flexibility around working hours, she explained that many barriers faced by neurodivergent people are often created by traditional workplace systems rather than individual limitations. Importantly, these adaptations frequently benefit everyone, not just neurodivergent employees.
Nice versus kind leadership
Perhaps my biggest takeaway was Cherie's distinction between being nice and being kind. Over time, she realised that constantly rescuing people or avoiding difficult conversations wasn't helping anyone grow. Instead, effective leadership means creating psychological safety while still holding people accountable, having honest conversations and supporting development.
As Cherie described it, psychological safety is not about avoiding discomfort. It's about ensuring that discomfort doesn't become damaging.
Final thoughts
This conversation challenged many traditional ideas about ambition and performance. Cherie's perspective reminds us that sustainable success isn't about constantly asking people to do more. It's about creating environments where people can do meaningful work, continue growing and still have energy left for the rest of their lives. For leaders, that may be one of the most important measures of success we have.
Written by Tom Bosna
September 2026