Redirecting.work

 

What She Pivoted From

Chris’s career has been a tapestry of deliberate experiments and unexpected turns. After years in research advisory and a path toward Technology Fellow at Deloitte, she surprised even herself by joining Oracle in a product strategy role. “I had always said I wouldn’t do product,” she admits. Yet Oracle’s scale and its latent natural language understanding capabilities offered a playground she couldn’t resist. Over three years she helped accelerate innovation cycles, moving from long release cadences to on-the-fly deployments. She drove vision and investment strategies on technology that she  once analyzed from the outside -- and even bought, implemented, and utilized from the inside -- but at a cost. Personal time shrank to nothing. “It was the most intense three years of my life,” she recalls. “Hard enough to manage my job, harder still to manage my life.”

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Transition Process

The layoff was a jolt, but not a derailment. “I’ve always been working back to this,” Chris says of her plan to return to independent advisory. The difference is timing. Instead of 2027, the pivot begins in late 2025. As such, she is treating this stage as an intentional transition. She is drawing on her “informal board” who are trusted colleagues and friends who provide sounding boards and reality checks. She is also leaning on a lifelong habit of learning. Conversations are her classroom: she mines each one for insight, whether it’s a market signal, a fresh question, or a new idea.

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This is not the first pivot Chris has made under imperfect circumstances. Moves prompted in support of family, unplanned opportunities, role changes, or yes, even a layoff, have taught her to stay “North Star focused” on big complex, interesting problems worth solving rather than on specific titles or industries. “I’ve role-pivoted a bunch of times,” she says. “I tend to go where the pain is highest because I like being a part of solving it.”

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Emerging Direction

Chris is reactivating and rebranding her LLC to become an independent analyst and, more importantly, a trusted advisor. She frames her prospective clients as “buyers, builders, boards, and backers” and is letting the market reveal where her mix of skills will have the most impact. She’s experimenting with two brand identities: “AI Whisperer” and “AI Alchemist,” each reflecting a slightly different promise. The Whisperer guides organizations gently into AI understanding and adoption, while the Alchemist helps turn AI’s perceived “magic” into outcomes.

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What she knows for sure: she wants to provide a safe, judgment-free space for senior leaders to ask hard questions about AI, customer outcomes, and organizational readiness. “I’m very outcome driven,” she says. “It’s not about me. It’s about what my customers are trying to accomplish.” At this stage she isn’t confining herself to startups, venture-backed firms, or enterprises. “I’ll see where the market bears,” she notes.

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Advice for Others in Transition

Chris’s advice is rooted in questions rather than answers:

• Know the “what” and the “why” you love solving. “When you’re connected to the what and the why, that’s where you contribute and make the most impact.”

• Decide who you want to serve. Buyers, builders, boards, or backers, or even leaders, colleagues, customers, partners, or suppliers if you want to be internal to an organization. Stakeholders matter as much as the problems you solve.

• List what you don’t want as well as what you do. Chris often has clients start with what they refuse to take on; clarity emerges from contrast.

• Stay a continuous learner. “Think in questions, not answers. Assume you don’t know everything. That intellectual humility keeps you open.”

• Keep a service mindset. For Chris, spirituality means faith and openness and that doing the right work with the right people will reveal the next step.
   

Above all, she encourages people to embrace the “in-between” as a productive stage rather than a void. “I can be hungry and dirt broke, but I can’t do work that has no purpose,” she says. “Stay North Star focused. The purpose will find you, or you’ll find it.”