I took this picture while waiting to check in to return from Hong Kong. As I stood in line, I found myself reflecting on some of the coaching conversations I had during my time in the city. A couple of them centred around tough transitions into new roles: smart, seasoned professionals grappling with what it means to start over, again.
Whether you’re stepping into a new role, returning from a sabbatical, or switching industries altogether, every career transition is a kind of journey. And like any journey, we pack a bag.
But not everything we bring with us helps us travel well. The past roles. The labels. The patterns. The grudges. The imposter feelings. The stories we keep telling ourselves about what we can or can’t do.
In transitions, we often obsess over what we should bring with us: skills, networks, experiences. But the harder, more transformative question is: What should we leave behind?
Here’s a short “departure checklist” to reflect on:
Old titles and identities
You were a Director, a Specialist, a Top Performer. But your next chapter may require a different posture: learner, builder, listener, novice. Can you let go of who you were, to become who you need to be?Outdated definitions of success
What got you here may not get you there. Are you still chasing someone else’s version of success or are you ready to define your own?Past disappointments
That team that didn’t appreciate you. That boss who undermined you. That promotion you didn’t get. Carrying those moments too tightly can weigh you down. You can learn from them without dragging them forward.Fear of starting over
“Will I have to prove myself again?” Possibly. But fresh starts also mean fresh possibilities. Every expert was once a beginner again.Perfectionism and people-pleasing
A new chapter is an opportunity to set boundaries, work differently, and ask for what you need. Why not leave behind the habits that left you depleted?
Next time you step into a new role, imagine checking your mental and emotional baggage at the gate.
What do you need for the road ahead? And what can be left on the carousel of your past?
Travel light. Walk free.