October 2025 Newsletter

Lately, I’ve noticed an angsty trend among Tech folks in their mid/late career seasons.

People have become reluctant to invest their whole selves in their careers. This could be because of AI or layoffs or, because once you hit a certain point in any career, you just might not want to GRIND all day, every day. 

At the same time, I’m surrounded by furloughed government employees. Our city and neighborhood is full of folks who have spent many years in civil service, only to find themselves – and their families – caught in a political storm and shit out of luck.

Both groups are asking the same questions:

“Is it worth continuing to develop skills in this field?” 
“Should I see if I can retire early?”
“Am I competitive in this saturated market? Do I even want to be?”


In both cases, I hear that these folks are not sure if they have options, direction or fulfilling seasons ahead. In both cases, I feel they could use some support.

Enter: Plucky Circles

Plucky Circles are small groups designed to connect with others, specifically by sharing stories and practicing deep listening. In each of 5 sessions this fall, I’ll facilitate using an inquiry-style framework. Here are a few examples of the kinds of questions I might 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.

I experienced this facilitation framework myself earlier this year and really appreciate how it empowers personal narratives. If there was ever a moment when folks need to believe in their own stories, it’s now.

Feeling drawn to this offering? Know someone who might need it? Please share away…


Book launch!

Looking for something to read in the new year? I got you! My memoir, I Believe in Everything will be available at all of your favorite places (book stores, bookshop.org, and even Amazon) once it launches in January but you are now officially invited to pre-order a signed copy in Plucky’s Shop today!


“This was not the plan.”

I’m hearing this all over the place, applying to career trajectories, health updates, America’s future and AWS outages. I get it, I really do… and I’d like to humbly suggest that there was never going to be one plan, anyway.

You were never on a single, straight road. In my experience, the road keeps splitting, cul-de-sac-ing, causing your car to bottom out on potholes and sometimes exposing a very scenic route. This is how life works.

I leave you with this idea, to hold onto plans as long as they serve you but know when to step back and adjust expectations. Being nimble and confident in your ability to find a new direction never hurt anyone. 

Keep going,
xo Jen


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