Speaking – Caryn M Sullivan – Choosing Better 2017-01-29T22:38:39+00:00

I wanted to let you know how grateful I was to hear you speak last night. Not only is your life story so remarkable, but even more so your courage and strength in facing it all and remaining such a bright light for your family and others. Your message really touched me. Thank you for sharing so much of yourself. “

Lauri Badar

Convent of the Visitation School

Life struggles are universal. 

What defines us – distinguishes us – is how we respond to them.

Caryn Sullivan is no stranger to challenges. Starting at an early age she powered through family crises and health challenges with a stoic resolve. When her son was diagnosed with autism she left her law career to be his advocate. When she was diagnosed with breast cancer she declared, “I’m not going to die from this.”

But when her husband’s heart failed, Caryn’s resilience was put to the test. Would she bend or break?

The answer came unexpectedly from a priest she met at a social function. His response to questions such as “Why me?” and “Why my family?” offered her a lifeline.

“We can’t control what happens to us. But when adversity strikes, we have a choice. We can be bitter. Or we can be better.”

Caryn chose better. She garnered strength and wisdom from people who confronted adversity with grace and courage, many of them subjects of her newspaper columns. She stumbled upon a new purpose: to illuminate the choice for others. Drawing upon stories in her award-winning memoir, Bitter or Better, Caryn offers audiences a roadmap to resilience.

“Caryn told her inspirational story of courage with warmth and humor, and won the hearts of the audience in seconds. She crafted her message of “the only certainty in life is life’s uncertainties” to underscore the importance of financial planning. I highly recommend Caryn.”

Christopher Bentley
CFP, Ameriprise Advisors

Hire Caryn to Speak

Caryn's Speeches Focus On Three Main Ideas


Three Steps to Better

Being “better” is another way of broadcasting I’m a fighter. I’m resilient. It’s a response to the question Will you bend under the weight of life’s challenges or will you break? People often ask Caryn how she has survived so many life challenges. It’s simple, though not easy. Caryn offers three action steps to being better: look up; reach out; and step forward.

Living in the Moment, Preparing for the Inevitable

Despite serial health challenges, Caryn was unprepared to become a widow and single mother. Like many, she had lived in disregard, denial - perhaps defiance - of the one thing that is certain to happen in life! Wiser now, Caryn explains how grappling with end-of-life questions brings us peace in our lifetime; and how engaging in uncomfortable discussions and making difficult decisions helps our loved ones to avoid conflict when we’re gone. With her trademark “Box of Love” and her planning checklist, Caryn empowers audiences to prepare for the inevitable so they can more joyfully live in the moment.

ARRM Conference

Gifts, Gratitude and Gumption

Everyone has gifts. People do. Organizations do. Yet we’re often reluctant to acknowledge them. Caryn offers examples of how successful people use their gifts to push back against adversity. She explains how an organization can thrive by using the synergy that flows from the combined gifts of many. Drawing upon both research and anecdotes she offers insight into how using gifts, expressing gratitude and fostering gumption leads to resilience.


"Caryn gave a wonderful and heartfelt presentation to our Rotary Club of Edina. Her inspirational thoughts were very well-received by our membership, both young and old. I highly recommend other organizations have her share her history and recommendations on what people need to do in planning for their future - one of the most important transactions in a lifetime for all families." 

Bradley J. Hepp, CPCU, ARM, Hepp Risk Consultants

Caryn has spoken at the following venues: