By mid-career, Karen Kelly has reinvented herself more times than most people dare to dream.

From ad agency burnout in New York City, to scrubs and red tape as a speech pathologist, to moonlighting as a photographer, to running a seven-figure media business, to CMO and later President of a tech company, to volunteer community organizer and change-maker, to present day Co-Founder and CEO of Launch by Lunch, she has turned curiosity and resilience into her career compass.

In this conversation, Karen opens up about the roadblocks we create for ourselves, the power of listening to signals, and the surprising ways creativity and community can reshape what’s next. We dig into:

• Why “too many ideas” can be a superpower if you learn how to channel it.

• The moment she realized storytelling mattered more than the photo itself.

• Building a grassroots childcare solution in her hometown during the pandemic.

• Painkiller vs. vitamin thinking when launching new ventures.

• How to give yourself permission to pivot—and crystalize fleeting moments into something lasting.

If you’ve ever felt trapped by sunk costs, uncertain about your next season, or hesitant to put your work into the world before it feels ready, Karen’s story will give you both a framework and the encouragement to move forward.

Let’s keep making career more of a team sport.

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Connect with Karen on LinkedIn

Visit the website for her company, Launch by Lunch, to learn more about building with no-code tools and the community of leaders waiting for you to join them.

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Host: Brady Sadler

Let's connect on LinkedIn

Show Art: Kyle Mosher