Work is Weird Now

S2E9: What should you know before you quit? With Mark Heywood


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Guest: Mark Heywood – podcaster, writer, former investment banking MD, and co-founder of Don’t Quit

This week on Work Is Weird Now, we speak with Mark Heywood about the realities of leaving corporate life and reinventing your career on your own terms.

From his early days in tech at RBS to a screenwriting course in LA and launching his own business, Mark’s story is anything but linear. In this deeply honest conversation, he shares how he engineered his transition out of banking, the mindset shifts that made it possible, and why failure is a necessary companion in freelance life.

We unpack the emotional and practical prep required to go solo, the myths around quitting, and how Don’t Quit is helping others leave with their eyes wide open.

Key Topics:

  • Freelancing is a lifestyle shift, not just a job change
  • Job titles don’t define your value — skills do
  • Most of us don’t quit too soon — we stay too long
  • Failure isn’t fatal. It’s essential
  • Why schools aren’t teaching the skills we actually need for the future of work
  • You don’t need all the answers before you leave — just the right questions

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.)

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Work is Weird NowBy Danielle Emery