A book & video interview series
Knowing When is a series of honest conversations with accomplished people about the pivotal moments in their careers and lives — and how they knew it was time to coast, stretch, or leap.
Interviews publish on YouTube. Selected stories appear in the forthcoming book.
Choosing a good-enough season on purpose. Protecting what matters. Staying — not from fear, but from clarity.
Taking the assignment you are not quite ready for. Asking for what you have earned. Becoming a beginner again.
Leaving while you are still succeeding. Creating the role that does not exist. Choosing purpose over prestige.
About the series
Most advice tells you what to decide. Almost none of it tells you how people knew it was time.
Knowing When explores the pivotal moments that shape careers and lives — not only the decisions people made, but the signals they read, the trade-offs they weighed, and the quiet preparation that came before the visible change.
We talk with accomplished people across generations, because every generation approaches ambition, loyalty, balance, and success differently. We may not make the same choices — but we can stay willing to understand and learn from one another.
Full conversations are published on YouTube. Selected stories are being developed for the forthcoming Knowing When book, and clips and insights are shared through social and educational channels.
Mentorship should not end with formal programs or private conversations. It continues through the stories and experiences we pass forward. Varsha Waishampayan & Joe Kennedy
Anyone standing at a crossroads — early in a career, mid-climb, or deciding what a next chapter should look like — and anyone who mentors, coaches, or leads people who are.
The eight themes
It may be a quiet but important decision to grow, wait, prepare, change direction, or choose something that mattered more.
Advocating for the opportunity you deserved. Taking an unconventional assignment. Distinguishing growth from burnout.
Pursuing a postponed dream. Becoming a beginner again. Growing beyond an identity others still associate with you.
The person who saw it first. The advice that landed. Learning to ask, and learning to sponsor someone else.
Reconsidering a promotion or letting ambition wait. Staying intentionally rather than remaining from fear.
When life needs more of you than work does. Supporting a partner's opportunity. Preparing quietly for what comes next.
Trust, boundaries, loyalty. Knowing when to repair a relationship — and when you have outgrown it.
Leaving while still successful. Creating the role you cannot find. Using experience to launch a new chapter.
Redefining a life that no longer fits. Empty nesting, retirement, or an unexpected future. A leap that may not make sense to others.
Don't see yours? Tell us about your own Knowing When moment — any decision that showed the grace to coast, the wisdom to stretch, or the courage to leap.
How it works
No preparation, no script, and nothing published without your approval. Here is the whole process.
A short, informal call to understand your story and find the direction that means the most to you. Roughly 20–30 minutes.
A guided interview over Zoom — video and audio — typically 45–60 minutes. You will receive the guiding questions in advance. In-person recording is possible when schedules and location permit, and is entirely optional.
The interview is edited for length and clarity while preserving the meaning and integrity of your story, then published as a video episode. The audio may also be released separately.
An excerpt or a fuller version of your story may be considered for the Knowing When book. Any written version is shared with you for review and approval before publication.
You do not need written answers. These are simply here to help you reflect before we talk.
The hosts
Founder & CEO, WINGS for Growth · Founder, Global Mentorship Institute · Co-Founder, Knowing When
Varsha Waishampayan is a seasoned executive, social entrepreneur, and leadership advocate with nearly four decades of experience spanning academia, Wall Street, corporate leadership, and nonprofit governance. Her distinguished career includes working with global institutions such as Goldman Sachs, PwC, Citigroup, and Bank of America.
Beginning her professional journey as a professor of Chemistry, Varsha developed an early passion for education, mentorship, and unlocking human potential. Inspired by her late father, a lifelong educator, she later made the bold decision to leave a successful corporate career to pursue a greater purpose: helping others realize their leadership potential.
She founded WINGS for Growth, a nonprofit organization dedicated to advancing leadership through structured mentorship and executive development. Under her leadership, WINGS has empowered hundreds of professionals and built a global network of senior executives, mentors, and emerging leaders. The organization collaborates with leading companies, including Capital One, Citi, JLL, and PwC, to strengthen leadership pipelines and cultivate mentorship-driven cultures.
Expanding this mission, Varsha established the Global Mentorship Institute (GMI) to advance mentorship through executive development, mentor training, organizational strategies, and AI-enabled innovation—driven by her vision of making mentorship accessible to anyone, anywhere, anytime.
She also co-founded Knowing When, an initiative focused on helping individuals navigate pivotal career and life transitions through its guiding philosophy: “The Grace to Coast, The Wisdom to Stretch, and The Courage to Leap.”
Known for her authenticity, strategic insight, and commitment to developing others, Varsha believes that true leadership is measured not only by personal achievement but by the opportunities we create for others.
Technology Executive & Entrepreneur · Author, The New Bottleneck · Co-Founder, Knowing When
Joe Kennedy is a technology executive, entrepreneur, author, and mentor with more than three decades of experience spanning financial services, consulting, and enterprise transformation. He currently serves as CIO of Global Operations at a top-five U.S. bank, bringing a builder’s perspective to leadership, organizational change, and complex technology delivery.
As a Principal at PricewaterhouseCoopers (PwC), Joe led Financial Services Advisory Technology capabilities, advising executives at more than 225 clients, predominantly Fortune 500 companies. His work connected business strategy with technology design and execution, helping leaders navigate complex platforms, enterprise architecture, and large-scale transformation. He worked across banking, asset management, and private equity, translating difficult business challenges into practical technology decisions and delivery approaches.
Previously, Joe led Data Warehousing and Information Delivery Architecture at State Street. At PAREXEL International, he built and led the internet technology organization, connecting 27 global locations through network, security, and application infrastructure.
As Founder of Kennedy Innovations, Joe brought technology services to 110 companies, with a deliberate focus on nonprofits, startups, and underfunded organizations.
Across his executive, advisory, and entrepreneurial career, he has influenced more than 600 organizations, from small businesses to global institutions, helping them address the technical and organizational obstacles that stand between ambition and results.
Joe is the author of The New Bottleneck: The New Delivery Model for the AI-Enabled Age, exploring how AI shifts the challenge of software delivery from execution to clarity of intent. He serves as an advisor and mentor with WINGS for Growth, supporting women pursuing leadership opportunities. He previously served for years as a board member of the Massachusetts Multiple Sclerosis Society.
He co-created Knowing When with Varsha Waishampayan, bringing together a book and video interview series about pivotal career and life transitions. Through honest conversations across generations, they help people learn from the choices of others.
Coming soon
Questions
A 20–30 minute introductory call, then a 45–60 minute recorded conversation. That is the whole commitment. There is no homework and no script to learn.
No. We share the topic and guiding questions in advance so nothing catches you off guard, but written answers are never expected. No professional equipment is required either — we provide simple technical guidance and run a short sound and camera check before recording.
The conversation is recorded in video and audio. The video may be published as an episode on YouTube; the audio may be released separately. Selected clips, quotations, photographs, and insights may be shared through social media and other promotional channels for the series and the book.
The interview is edited for length, clarity, and presentation while preserving the meaning and integrity of your story. You can raise concerns about factual inaccuracies or anything sensitive that was unintentionally disclosed. Any written version considered for the book is shared with you for content review and approval before publication.
Tell us before we record. Guests may identify sensitive, confidential, or off-limits subjects, and you will never be expected to disclose anything that compromises your privacy, your professional obligations, or the confidentiality of others.
Your preferred name, title, and organization; a short biography and a headshot; any website or social links you would like included; the correct pronunciation of your name; and any topics or organizations you cannot discuss publicly.
Yes. You can share your story with us in writing instead, and it can still be considered for the book.