The question of when to leave a job hits differently when you’re stuck in the grind of 12–15 hour days, watching other creatives seemingly thrive with better work-life balance. It’s one of those career crossroads that can feel both urgent and paralysing — especially when you’re weighing financial stability against your wellbeing and wondering if the grass really is greener elsewhere.

This question was answered by Andy Wright – Host, CEO Streamtime and Founder of Never Not Creative, who brings a depth of experience building healthier workplace cultures; Simon Lee – Chief Creative Officer and joint owner of The Hallway, who took a pay cut 16 years ago to leave a well-paid job for a startup agency, giving him firsthand perspective on making the leap; and Aimee Davies – mental health educator and counsellor specialising in creative professionals, whose therapeutic insight helps navigate the emotional side of major career decisions.

Be Wary of Instagram’s Highlight Reel

Simon offers a reality check on those inspiring small studios online: "Be wary of the Shiny Happy People on Instagram... it’s a risk, and there’s no guarantee it will work out." Having made the leap himself, he knows the freedom comes with relentless hard work and some luck — something social media rarely shows.

Know Your Personal Values

The clearest sign it’s time to leave is when a job runs counter to your core values. Simon explains: "The time to leave is when the job that you’re in is actually running counter to those values... then my advice would be to move on." Reflect on the decisions you’ve made before — what influenced them? That’s your values in action.

The Reality of Long Hours

Simon gives an honest perspective on long hours: running your own studio can mean working just as much, especially early on. "You have to be so passionate and so driven to make it work that you just do the hours... it can be 10 years before you’re able to take the foot off the accelerator."

Industry Culture is Changing

Andy shares hope that the culture is shifting. "Things are changing... I’d say cultures have improved. There are laws now — excessive workloads are increasingly seen as a psychosocial hazard." He encourages people to consider finding a better workplace culture before making an extreme leap.

Control vs. Choice

The key distinction Andy makes is about control: "If you feel you’re able to be in control of your work, that’s your choice. But if you’re not in control and that’s not a choice, that might go against your values and your health." Simon echoes this, describing how The Hallway now rarely requires late nights, a big change from earlier years.

Knowing when to leave a job ultimately comes down to your values and whether your role aligns with them. Social media doesn’t show the risks and grind behind the highlight reel. The good news? Agency cultures are evolving, and legal protections are growing stronger. Whether you find a better-fit studio or take the leap to start your own, focus on ensuring you have control and choice. If your current role is consistently undermining your wellbeing and core values, trust your instincts — it may be time to move on.

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