Plucky Circles (Fall 2025)

Plucky Circles

There are certain seasons of your career when you need direct coaching around actions, specific skills and networking. And then there are others when, well, you just don’t know what you need. Today, I’m launching Plucky Circles, supportive groups designed for folks in this headspace.

Plucky Circles are a way to connect with others, specifically by sharing stories and practicing deep listening. In each of 5 sessions, Jen will facilitate using an inquiry-style framework. Here are a few examples of the kinds of questions Jen may ask:

  • I wonder about a time when you took something very challenging across a finish line.
  • I wonder about a time when you felt unsure about your work.
  • I wonder about a time when someone really helped you land on your feet.

In these groups, folks are invited to share (or not!) and – here’s the nuance of Circles – after sharing, the room returns to silence. No one will jump in to correct your story, connect your story to their own, or offer advice. We return to silence until the next person wants to share. In this way, we hold space for you to explore your own narrative.

At the end of each session, Jen will step in to teach a short, relevant lesson regarding that week’s topic. In that part of the call, conversation flows like normal and folks can respond at-will.

It’s my hope that Plucky Circles will help group members to find their ways during nebulous times.

There will be two pilot Circles this fall, both capped at 8 attendees:

Government Workers
You are a federal worker/contractor and may be laid off, furloughed or still working.

Price: free

Dates: 12-1pm ET on Wednesdays (10/29, 11/5, 11/12, 11/19, 12/3)

Career Regrounders
You’re established in a tech career and finding yourself unclear about the next stretch of your career. This could be due to developments in AI, lay-offs or mid/late-career angst.

Price: $249.

Dates: 12-1:15pm ET on Mondays (11/3, 11/10, 11/24, 12/1, 12/8)

Reserve your seat now; they will go fast!