58. Following Your Own Path with Entrepreneur and Leadership Coach Jen Dary

On today’s episode, I’m talking to Jen Dary, a leadership coach and career coach for new managers. She is an entrepreneur and the founder of Plucky, a leadership coaching and consulting firm. 

Jen has a BA in English, French, and Writing from Muhlenberg College and a MA in French from Middlebury College.

You are correct if you’ve started to notice that Jen isn’t the typical guest on the Madam Athlete podcast! In fact, she was my RA at Muhlenberg College when I was a freshman (hi there, it’s Giselle – I’m the host and founder of this whole Madam Athlete thing… nice to meet you!). So I’ve known for a long time that Jen has amazing advice. And she’s had such an incredible career journey, including time in professional development for tech companies, and now starting her own business as a career and leadership coach, I knew she’d have useful information even if she’s not in the world of sports or athletics.

(I get into all of that at the beginning of the episode, and it is a great episode, so stick with it!)

Jen began her career working with the French-American School of New York. When an opportunity presented itself to move into the world of tech, Jen chose to honor the part of herself that sought new challenges and became the Managing Director of Employee Development with Arc90. After years of working on what she calls the human side of technology, she took a huge risk to start her own firm, Plucky, to reach people on a broader scale. Jen talks about starting a business in the year after giving birth to her first child and her experience with postpartum depression. She also wrote about Plucky’s first year in her article, People are Your Future . With Plucky, Jen has worked with Google, Facebook, The New York Times, Slack, Code for America, and many others. 

Jen describes how each step in her career allowed her to develop different skills that she can pull from now as a leadership coach. She currently runs a program called So Now You’re a Manager and will teach her twentieth cohort this fall. As Jen celebrates Plucky’s eighth anniversary, she’s also preparing for the upcoming launch of Manager Weeklies, a weekly planning system designed by drawing from the best practices of successful managers.

We talk about:

  • Transitioning careers to find fulfilling work
  • The cancer diagnosis that deepened her appreciation for people doing their best work
  • Setting up each week for success
  • Managing by listening

For more information about Jen Dary, you can find her on social:

And as I mentioned in the episode, my free LIVE masterclass on how to Crush Your Imposter Syndrome has officially returned! Sign up now to save your seat and get started on building your career confidence and being done with this whole imposter syndrome cr*p.

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