Oct. 14, 2026

Should I Stay or Should I Go?

Should I Stay or Should I Go?
Should I Stay or Should I Go?
Transformative Leadership Conversations with Winnie da Silva
Should I Stay or Should I Go?

Should I stay or should I go? How long is too long to wait for that next promotion, bigger opportunity, or the recognition I've been working toward?

It's a question I'm hearing more and more from my clients, especially as the job market gets tougher and the decision to leave a company isn't so straightforward. In this episode, I'm digging into the growing issue of mid-career stagnation, sharing what I'm seeing with clients who are weighing loyalty against new opportunities, why staying isn't necessarily a bad move, and why leaving isn't always the answer either.

Resources

Burning Glass Institute - "Sidetracked: The Hidden Crisis in Mid-Career Mobility"

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - winnie@winnifred.org