Build Your Own Boat

After more than two decades leading global technology teams at Oracle and serving as VP of Services at an AI-driven consulting firm, Kristen Harris was laid off at 55 — a moment that felt devastating even though she already knew the role wasn't right for her. In this episode, Harris explains why perfectionism isn't a flaw to "recover from" but a trait that high achievers can sharpen into a strategic advantage, and how surviving breast cancer while working full-time reshaped her relationship to risk, corporate health benefits, and what she was willing to sacrifice for stability. She shares the exact framework she now teaches leaders — from millennial managers to midlife career-changers — for identifying their "unfair advantage," building an informal personal board of directors, and taking the leap into entrepreneurship without having to build the perfect business before selling it.

Kristen Harris spent more than 20 years leading global technology and consulting teams, including roles as a director at Oracle — where her team delivered web platforms across nine languages for the entire company — and VP of Service Delivery at a software engineering and consulting firm, where she managed project delivery, resourcing, profitability, and quality at the leadership table. At 55, following a corporate layoff, she launched Kristen Harris Coaching, where she works with leaders and teams on leadership development, resilience, and what she calls "the perfectionist edge" — helping high-achieving, perfectionist-minded professionals turn that trait into a strength rather than something to apologize for. Harris is also a breast cancer survivor who continued working through treatment, an experience that reshaped her views on risk, stability, and building professional presence. She now serves as a cancer mentor through Imerman Angels, a Chicago-based nonprofit that connects cancer patients and caregivers with survivor mentors for one-on-one peer support.

Not according to Kristen Harris. She argues perfectionism only becomes a problem when it's unexamined. Roughly 85% of high achievers identify with some form of perfectionism, and rather than treating it as something to "recover from," Harris teaches leaders to identify their specific perfectionist type and channel it into strengths like precision, resilience, and high standards.

Health insurance and financial stability are among the biggest reasons women delay leaving corporate roles to start a business. Harris recommends treating this as a knowledge gap rather than a fixed barrier — talking to insurance brokers, researching healthcare exchanges, and understanding real options before assuming a corporate job is the only path to coverage.

Harris recommends building an informal "personal board of directors" made up of trusted advisors, former colleagues, coaches, family members, and even new connections made through networking. The goal is to avoid isolation and get honest, varied perspectives rather than relying only on close friends who tend to agree with everything you say.

It's one of several perfectionist types described by psychologist Katherine Morgan Schafler in her book The Perfectionist's Guide to Losing Control. A Parisian perfectionist appears polished and put-together on the outside while struggling internally — for Harris, this showed up as difficulty delegating and giving others growth opportunities because everything felt like it had to be done a certain way.

Harris suggests starting with the dream itself — can you clearly picture what you want and yourself doing it? From there, assess your financial and relational stability, and your resilience to handle early rejection. If your foundation is solid and you can bounce back from setbacks, that's a strong signal you're ready to take the leap.

Build Your Own Boat is a podcast series hosted by Janine Vanderburg — award-winning three-time entrepreneur and anti-ageism advocate — featuring women who have launched new entrepreneurial ventures in midlife and beyond. The series is part of a larger storytelling project that includes a Substack publication and a forthcoming book, all built around one goal: changing the narrative about who entrepreneurs are and making women in midlife and beyond visible as builders of wealth, freedom, and possibility.