Getting Out of Your Head
AND Into Action
March 2026 - November 2026
Registration for this session is now closed...Stay tuned for upcoming opportunities!
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Registration for this session is now closed...Stay tuned for upcoming opportunities! *
Are you feeling stuck, restless, or unfulfilled in your professional life?
Wondering if there is something more meaningful out there but unsure
how to take the first step?
You are not alone.
Studies show that over half of professionals are considering a career change, yet most never make the leap. Why? Because traditional advice tells us to “figure it out” before we act. But what if that’s backward?
It’s time to flip the script.
This dynamic, cohort-based workshop is designed for mid- to senior-level professionals who are ready to explore new possibilities and take real steps toward a more fulfilling work life. Inspired by Herminia Ibarra’s groundbreaking book, Working Identity, we embrace a bold new approach:
Action leads to clarity.
This workshop is for you if you:
✓ Are contemplating a career shift – big or small
✓ Crave a fresh, action-oriented approach to
career change
✓ Thrive with structure, accountability, and peer support
✓ Want to make meaningful progress toward your
“what’s next”
What’s included?
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Join coach-facilitated synchronous sessions that fit your busy schedule. Together with your cohort, you will more deeply explore “Working Identity” content and concepts, benefit from other perspectives and experiences, and safely experiment and receive feedback.
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Get two one-on-one sessions with a certified career coach. These sessions provide you with a personalized experience. You choose the topics that are most important to you and will bring you the greatest value on your journey.
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Test your new career directions in real life. Career experiments are small, low-risk actions—like shadowing someone, taking on a new project or assignment, volunteering, or taking a course—that help you test new directions and gather real-world feedback.
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Get support from a cohort community. Your cohort is your support system—a group of peers who share insights, ideas, challenges, and encouragement throughout the journey.
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Enhance your learning path with short lectures, self-reflection, group discussions, and more.
Session Schedule
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Session 0: Meet and Greet | March 9, 2026/6:00 PM CDT
Getting to know your cohort and sharing expectations.
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Session 1: Who and Where am I Right Now? | March 12, 2026/6:00 PM CDT
Sharing career narratives, values, and visions for the future
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Session 2: Discovering and Exploring Possible Selves | April 9, 2026/6:00 PM CDT
Letting go of the ‘one true self’ idea and exploring the many possible selves already inside you.
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Session 3: Experimenting, Part 1: Overview | May 14, 2026/6:00 PM CDT
Why and how to get out there and do! Small-step no-one-right-way experimenting with new activities, new relationships, and new narratives.
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Session 4: Experimenting, Part 2: Deeper Dive | June 11, 2026/6:00 PM CDT
Productively reflecting on your experimental data; expecting and dealing with liminal confusion, turmoil, and temptation; taking breaks; winnowing possible selves.
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Session 5: Deep Change: Group Coaching | August 13, 2026/6:00 PM CDT
Sharing the deeper realizations uncovered by experimenting – who am I becoming?
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Session 6: Sharing Experiments, Part 1 | September 10, 2026/6:00 PM CDT
Now is when your cohort shines its brightest as a safe place to share your progress, detours, frustrations, successes, and challenges, and to brainstorm together on moving forward.
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Session 7: Sharing Experiments, Part 2 | October 8, 2026/6:00 PM CDT
Another opportunity to share with and support your cohort as you each discover your unique path around the working identity wheel.
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Session 8: Moving Forward | November 12, 2026/6:00 PM CDT
Wherever you are in your journey by this point, we will together acknowledge and celebrate where you have been, where you are, and the places you have yet to go.
By the End,
You Will:
Discover new career possibilities through real-world experimentation
Gain clarity and confidence about your next steps
Build a supportive network of fellow professionals
Walk away with direction for your professional future
Meet Your Instructors
Kathy Romaine
Kathy’s interest in career reinvention is not simply professional curiosity. She’s done it – twice.
Coach | Consultant | Change Navigator
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She’s lived the uncertainty, the pivot points, and has come to appreciate the power of experimentation. Her first major transition came in 2014, when years of overwork and misalignment left her feeling lost and barely recognizing herself. She stepped away from a successful role in science and engineering consulting and followed the typical “know” then “do” approach, taking time to reflect and looking inward to figure it out. Her recalibration led to a slight pivot, staying in the same field with a new focus: building business and leading people.
But it was her second transition, beginning in 2020, that truly embodied the “doing leads to knowing” approach. Kathy first began exploring coaching as a tool to deepen leadership skills. As she tested, practiced, and refined her coaching skills within her existing role she also sought additional training, which both broadened her network and opened her up to new possible selves. Eventually this doing led to knowing – coaching was not just a tool, it was the best part of her day. So she made it the whole of her day by launching her own coaching and consulting practice, where she helps others navigate change with clarity and confidence.
Kathy brings over 25 years of cross-sector experience and holds coaching certifications from Northwestern University and the University of Wisconsin. She is a credentialed coach (ACC) through the International Coaching Federation, holds a Project Management Professional certification from the Project Management Institute, and a Master’s in Environmental Management from Duke University. Kathy’s deep understanding of the unique challenges involved in realizing and implementing change powers her passion about helping others achieve their desired outcomes with fewer obstacles and in less time. Her approach is grounded, empathetic, and action-oriented – because she knows firsthand that clarity comes through movement.
Coach | Legal Professional | Creative Educator
Roy Underhill
Roy’s career path is a masterclass in reinvention.
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As a young lawyer he spent 2 years each as clerk for a federal district judge, associate at a large law firm, and teaching at a law school. While all three are perfectly ordinary roles for a lawyer, each required a different mindset, workflow and style of colleague collaboration. Roy had no time for reflecting; he just jumped in and figured it out as he went.
But by far his most transformative transition came when he moved to Wisconsin and became a full-time, stay-at-home homeschooling father. In this new role, Roy embraced unpredictability, creativity, and continuous adaptation. Every day was a new experiment. With no set curriculum and two ever-evolving “clients,” he leaned even more into his background in philosophy and the creative arts to foster a learning environment both rigorous and joyful. He also shared his insights through numerous presentations on myriad topics at the annual statewide homeschooling conference, showing others how to let go, have fun, and truly learn.
On outsourcing this role to college, Roy reinvented himself once again – this time as a part-time legal guardian ad litem while simultaneously overseeing a full-scale farmhouse renovation. Along the way, he discovered coaching as a natural extension of his lifelong commitment to growth, transformation, and outside-the-box thinking.
Roy holds a coaching certification from the University of Wisconsin, a law degree from the University of Chicago, and a dual-major Bachelor of Arts/Bachelor of Music from Lawrence University. His coaching is informed by a rich tapestry of life experience, intellectual curiosity, and a deep belief in the power of experimentation to reveal what’s next.
FAQs
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This workshop is a guided, action-oriented experience for professionals ready to explore new career possibilities and new working selves. Instead of waiting for clarity before making a move, we help you gain clarity through action – testing ideas, reflecting, and learning as you go.
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It is ideal for mid- to senior-level professionals who are feeling stuck, restless, or unfulfilled and want to explore “what’s next” in a structured, supportive environment. Recognizing that it takes time to make a career transition, this workshop works best for those giving themselves at least several months (if not a year or more) to do so.
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We do not start with resumes or job boards. Inspired by Herminia Ibarra’s “Working Identity,” we focus on real-world experimentation and reflection. You will learn by doing – not just thinking. And you will not be alone! You will have the power of your cohort’s shared experiences – other individuals going through career transitions of their own.
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The workshop cost is $950. The fee includes all live sessions, two individual coaching sessions, workshop materials, and access to your coaches (through office hours) and cohort community. Workshop participants will be responsible for purchasing their own copy of Herminia Ibarra’s “Working Identity” in electronic or paper format.
Yes! We offer a $150 discount if we receive your registration and full payment on or before February 15, 2026. We also offer limited scholarships and will work with you on an alternate payment schedule (if needed). Please contact us for additional details.
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We understand life happens. Should you need to withdraw from the workshop for any reason, we will provide a 100% refund if we receive your cancellation request on or before February 15, 2026. We will provide a 50% refund if we receive your cancellation request at least 2 weeks prior to our first virtual session.
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“Working Identity” challenges the idea that we must “figure it out” before we act. Instead, it encourages trying new roles and identities to discover our true possibilities. This philosophy is at the heart of our workshop.
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Topics include envisioning new working identities, experimenting with different possibilities, moving through periods of transition and uncertainty, making new and different network connections, updating personal narratives, and using a strategy of small wins to bring about your desired change.
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The workshop runs from March 2026 to November 2026 (excluding July), with monthly live sessions designed to fit your schedule. We anticipate meeting on the second Thursday of the month [March 12, 2026, April 9, 2026, May 14, 2026, June 11, 2026, August 13, 2026, September 10, 2026, October 8, 2026, and November 12, 2026] at 6:00 PM Central Time. Live sessions will be 90 minutes in length. A Meet and Greet session will be scheduled prior to the March 12, 2026 session.
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Expect about 2 to 4 hours each month for live sessions, coaching, and self-study (e.g., book reading, exercises). Additionally, participants will self-direct their own experimentation and the time required for that will be up to each participant
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All sessions are held virtually, making it possible to participate from anywhere.
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Yes! Recordings of live sessions will be available so you can catch up if you need to miss one. Please note, however, that recordings will not be available for breakout/small group discussions. Participants are encouraged to attend the live sessions for maximum engagement and the best experience.
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We keep cohorts intentionally small to foster connection, trust, and personalized support. You can expect your cohort to be between 10 and 20 people.
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Most importantly, a desire to explore your new career possibilities and new working selves, your curiosity and a willingness to put things into action, to experiment! You will be required to purchase your own copy – paper or electronic – of Hermenia Ibarra’s “Working Identity” (Updated Edition). You will also need internet access and a computer or other device – or access to one – that meets the minimum system requirements for installing and running Zoom and is equipped with microphone and camera.
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Virtual sessions provide an opportunity to more deeply explore “Working Identity” content and concepts, benefit from other perspectives and experiences, and safely experiment and receive feedback. Coaching sessions are 1:1 and provide you with a personalized experience. You choose the topics that are most important to you and will bring you the greatest value on your journey.
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We acknowledge that the topics of career reinvention and working identities are sensitive. We create a safe, respectful space where confidentiality is expected and upheld by all participants. Information exchanged by workshop participants will not be shared outside of the workshop.
