Paint the Canvas Before You Exit: How to Prepare for Life After Work

The Impostor Syndrome Files

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In this episode of The Impostor Syndrome Files, we explore a life transition that often goes unexamined: retirement. What happens when your professional identity has defined you for decades, and suddenly you’re faced with the question, “What now?” My guest this week is Sarah Friedell O’Connell, executive transition coach and founder of ChangePoint Advisors. Sarah specializes in helping high-achieving professionals prepare for the non-financial side of retirement—what it means for their identity, purpose, and daily life.
Together, we unpack the emotional and psychological aspects of leaving full-time work, how to intentionally design your next chapter and why so many of us struggle to imagine a fulfilling life outside of our careers. Whether you’re approaching retirement or simply want to live more intentionally now, this conversation is a powerful reminder that transitions don’t have to be terrifying, they can be transformational.
About My Guest
Sarah Friedell O’Connell is an Executive Transition Coach and the owner of ChangePoint Advisors, a firm dedicated to helping senior executives navigate career changes. Sarah brings both business and career management expertise to her work with senior leaders, and her background as a former communications executive at Fidelity Investments and a spokeswoman for the President of Harvard University gives her a unique perspective and deep understanding of business and leadership. Sarah made her own career pivot into executive coaching, so she understands what it takes to successfully manage major change.
Sarah has been coaching C-suite executives for over 10 years, helping hundreds of executives across a variety of industries and functions achieve success personally and professionally. Sarah is a graduate of the College of William and Mary where she received a B.A. degree, and is certified in several psychological assessment tools. She is a graduate of the Coaches Training Institute and the College of Executive Coaching and is a Certified Retirement Coach.

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Connect with Sarah:
Website: https://www.changepointadvisors.com/
LinkedIn: https://www.linkedin.com/in/sarahfriedelloconnell/

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