Career Confusion & Non-Linear Paths

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A session for anyone whose life doesn’t look like "the plan." Somewhere along the way, we were told our careers would make sense. Pick a path. Work hard. Move up. Feel stable. But real life rarely works like that.Maybe you’ve changed directions. Burned out. Started over. Taken jobs just to survive.
Outgrown something you worked years for. Or realized you don’t actually want the thing you thought you were supposed to want.
Career confusion can feel isolating — especially when everyone else seems certain, successful, or “on track.”

This session is a space to talk honestly about the messy middle: the doubt, pivots, gaps, detours, and reinventions that don’t fit neatly on a resume.

We’ll reflect on:

• Pressure to have a dream job
• Comparison and “falling behind”
• Identity tied to work
• Grief for paths we didn’t take
• What it means to define success on your own terms

This isn’t networking. It’s not productivity coaching. It’s not “how to optimize your LinkedIn.” It’s a conversation for people who are figuring it out in real time.
If your path feels nonlinear, uncertain, or under construction, you’re exactly where you’re meant to be for this space.

Who Am I?
Hi, I’m Jesse, a communications and advocacy professional passionate about building a safer, more just world. Originally from Austin and now living in Italy, I believe life is measured by the quality of our connections, and I’m excited to use this space to help people build community through openness and shared stories.

How Does it Work?
This is an open, guided discussion led by your Keeper, Jesse. Each participant will have the opportunity to listen to and share experiences on anxiety, well-being, emotions, and whatever else comes up during the session.

When and How Do We Meet?
We meet digitally to make participation easy for those with demanding schedules. Cameras are optional, and you’re welcome to join from wherever you are, even between shifts. We only ask that you find a private place to join or use headphones to help maintain the security of everyone present.