Episode 96- Jamie Hammond '94, Founder, Digital Dirty Work, LLC
Mon Feb 02 2026
Jamie is a digital pioneer and reinvention strategist who has lived through every major wave of technological change from Y2K to generative AI. Jamie brings a refreshingly honest perspective on career transitions, leadership through uncertainty, and what it really means to reinvent yourself when the path forward isn’t clear. Jamie is also the author of What’s Next for Me?, released on January 12, a practical field guide for professionals navigating burnout, career confusion, and moments of reinvention. Just a few weeks after the book’s release, Jamie joins the podcast to unpack many of the same ideas in real time.
Our conversation centers on three powerful themes: clarity, curiosity, and the danger of confusing activity with impact. Jamie challenges listeners to slow down, ask better questions, and focus less on staying busy and more on doing meaningful work that actually moves the needle.
If you’ve ever felt burned out, stuck, or unsure whatyour “next step” should be, this episode will help you rethink how you lead, how you work, and how you move forward with intention.
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Jamie is a digital pioneer and reinvention strategist who has lived through every major wave of technological change from Y2K to generative AI. Jamie brings a refreshingly honest perspective on career transitions, leadership through uncertainty, and what it really means to reinvent yourself when the path forward isn’t clear. Jamie is also the author of What’s Next for Me?, released on January 12, a practical field guide for professionals navigating burnout, career confusion, and moments of reinvention. Just a few weeks after the book’s release, Jamie joins the podcast to unpack many of the same ideas in real time. Our conversation centers on three powerful themes: clarity, curiosity, and the danger of confusing activity with impact. Jamie challenges listeners to slow down, ask better questions, and focus less on staying busy and more on doing meaningful work that actually moves the needle. If you’ve ever felt burned out, stuck, or unsure whatyour “next step” should be, this episode will help you rethink how you lead, how you work, and how you move forward with intention.