Esther Osatuyi landed her first job out of university: managing a marketing team at a digital agency. There was just one problem: she'd never worked in marketing before. Not as a junior team member. Not even as an intern.For two years, she managed marketers who knew more than her, set timelines she couldn't defend, and sat in client meetings hoping no one would ask her to explain the strategy. When her team told her something would work, she had to trust them because she didn't have the expertise to push back.Eventually, the company started losing clients. Revenue dropped. And Esther realised they didn't need a project manager. They needed a marketing leader. Someone who actually understood the field.In this conversation, Esther reveals what really happens when you take a leadership role without transferable skills and why leaving was the best decision she ever made.What you'll learn:1. How to tell the difference between a stretch role and a breaking point2. The one skill gap that makes managing impossible (even if you're great at management)3. Why leaving a role doesn't mean you failed4. The checklist for evaluating leadership opportunities you feel unqualified for

Fresh out of university, James Praise landed his first marketing job and had absolutely no idea what he was doing. No network to call. No mentor to guide him. Just courses, self-doubt, and the constant fear that someone would realise he was faking it. But somewhere between taking obsessive notes and downloading every HubSpot template he could find, James discovered something: templates weren't just shortcuts, they were survival tools.Now, as the creator of Marketing in Action (a newsletter packed with tactical templates that thousands of marketers rely on), James has cracked the code on going from overwhelmed first-hire to confident systems thinker.In this episode, James traces his growth from relying on other people's templates to developing systems thinking and taste that lets him modify (and create) templates for his own unique use case.What you'll learn:1. Why self-doubt is actually normal (and what to do when the voices in your head won't shut up)2. The difference between templates, frameworks, and systems thinking (and why you can't template everything)3. The one question you must ask in your first 90 days to ensure you're working on what actually matters4. Why documenting your failures is just as valuable as celebrating your wins

"Welcome to the company. That's the culture here."

After Amos Feranmi's first call with his new boss, his teammates sent him that message. A former civil engineer turned marketer, Amos has worked under difficult bosses twice—and quit twice.

In this episode, he walks through the subtle signs of toxicity (diplomatic language masking aggression, zero respect for boundaries), the exact moment he decided to leave, and how "doing it afraid" built the confidence to walk away.

What you'll learn:

1. How to recognise when your manager has crossed the line

2. Why subtle verbal abuse erodes confidence faster than outright insults

3. The "confidence bank" approach: doing small scary things to build courage for big decisions

4. Practical advice for leaving when you have financial responsibilities