what should you know before you quit?
This week on Work Is Weird Now, we’re joined by Mark Heywood — podcaster, writer, former MD in investment banking, and co-creator of Don’t Quit, a new platform helping professionals transition out of corporate life into freelance work with realism, resilience, and support.
In this powerful and personal episode, Mark shares his own unconventional career journey, the mindset shifts that made it possible, and why a bit of failure is essential if you want to live — and work — on your own terms.
Mark’s Career Story: From Banking to Screenwriting
Mark’s journey began in tech at RBS — a job he admits he wasn’t technically qualified for. Alongside his corporate career, he nurtured a creative passion for writing, which led to a book deal, a film course in LA, and eventually a full shift into freelance life.
But it wasn’t an impulsive leap. It was a carefully engineered pivot, helped by corporate support, financial planning — and, crucially, a growing sense that his identity was no longer tied to a job title.
“I don’t know if I’ve ever had a career. I’ve had a collection of roles I’ve tried to do my best in.”
Failure Is Part of the Process
Mark doesn’t fear failure — he expects it. As a writer and entrepreneur, he sees every rejection as a step forward. What matters isn’t avoiding failure, but learning to fail better every day.
He credits this attitude partly to watching his father lose a job in the late ‘80s and seeing how deeply it affected him. That moment made Mark question how much of our identity is wrapped up in our work — and commit to doing things differently.
Don’t Quit: Helping Others Make the Leap
Mark co-founded Don’t Quit with Christian Hunt, a fellow ex-banker, after realising how little people are prepared for freelance life — especially when they’re used to the prestige and support of senior corporate roles.
The idea is simple:
Don’t quit your job until you’re ready — and we’ll help you get ready.
Their program is built to offer practical advice, honest stories, and mindset coaching for those considering a career transition. It acknowledges the myths (like needing total certainty or a “perfect time”) and focuses on building the resilience and skills required for real-world freelancing.
💡 Pro tip from Mark: If you realise freelancing isn’t for you — that’s a good thing to know. Better now than later.
Identity Beyond Titles
One of the hardest parts of going solo? Losing the status and structure of a “big job.” Mark shared how he rebuilt his professional identity around his skills, not his job title.
“I’ve never considered myself a technologist or a lawyer. There are just things I can do — and that’s where I focus.”
What Should Schools Be Teaching?
The episode also dives into the systemic failure of education to prepare kids for the flexible, multi-career future of work. Mark and the hosts agreed that:
Cognitive flexibility is the most essential (but under-taught) skill.
Kids should be encouraged to explore what they’re good at, not just what boxes they fit into.
Public speaking, storytelling, personal branding, and financial literacy are sorely missing from the curriculum.
It’s OK not to know what you want to do with your life — at 16, 36, or 56.
Key Themes
The myth of job security in corporate life
Freelancing as a full-body lifestyle shift — not just a job change
Why failure is a daily and necessary feature of entrepreneurial life
How careers are becoming collections of roles and reinventions
The urgent need for education reform to teach adaptability and curiosity
Connect with Mark Heywood
LinkedIn: Mark Heywood on LinkedIn
Don’t Quit Webinar Info: Find the latest updates on Mark’s LinkedIn posts.
(You can sign up and watch the replay anonymously if you’re not ready to go public about your career pivot.)
