Getting laid off can scramble more than your finances. It can shake your identity, your confidence, and the story you’ve been told about what “success” in customer support leadership is supposed to look like. That’s why this conversation with Jenny Dempsey hit so hard: she went from a clear leadership path in customer experience to two years of uncertainty, experimenting with consulting, and rebuilding from a place that felt anything but predictable.
We talk about the moment she realized a leadership title no longer matched her values. Jenny shares what it was like to apply for individual contributor roles with 20 years of experience, get judged as “overqualified,” and wrestle with the temptation to downplay her background just to get hired. We also unpack a healthier approach: owning the choice, leading without the org-chart label, and focusing on skills that actually create impact like clear communication, customer empathy, and making work easier for the team.
Then we zoom out to the unexpected parallel that ties it all together: her furniture flipping business. The product is different, but the customer journey is the same. Setting expectations, choosing the right channel, giving progress updates, and protecting trust when timelines are long. Charlotte puts it simply: silence kills trust. If you’re navigating layoffs, a career pivot, burnout, or a non-linear support career path, you’ll leave with practical mindset shifts and a better way to tell your story.
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