Maybe I Can: embracing challenge with Debbie Weiss

It was the second and last day of a Zoom workshop for authors who were hoping to get published, and Debbie Weiss dreaded the moment the publicist would call her name. She was the last on the list. After two days of nine-hour sessions, Debbie, who has a background in accounting and never wanted to be a writer, wondered what was on her mind when she decided to share her draft. She seriously considered clicking “leave now.”

Last year, after being an accountant and caregiver for most of her adult life, Debbie, at 60, became an author and podcast host and, just before the year ended, shared her journey as a caregiver on NBC’s The Kelly Clarkson Show.

Her memoir “On Second Thought... Maybe I Can” brings personal anecdotes of her life caring for her father, son and husband. In the “Maybe I Can” podcast, informed by her past struggles with self-doubt, she encourages listeners to explore challenging paths and make brave choices. Debbie, a certified Success Principles trainer with Jack Canfield, also owns the online store “Sprinkle of Heart.” Her next book, “The Sprinkle Effect,” will bring practical tips on overcoming self-doubt, and it’s scheduled for release in November.

Before Debbie could decide whether or not to leave that Zoom meeting, the author facilitating the event called her name. To Debbie’s surprise, her book was one of their favorites. She told them she had always been a “numbers girl” and never wanted to write. “You will never say that again,” the author told her. “You are a numbers AND a words girl.”

Debbie decided to start sharing her experience as a caregiver when she was 50 years old. “If not now, when?” she thought. Like host Amy Boyle, who at the same age asked herself questions like, “Who am I?” she was eager to find meaning in the past to inform her future and impact other people’s lives.

“I’ve been giving my life to everyone else, as I think many women do,” she told Amy during this episode. “And not that there’s anything wrong with that. But we also need to prioritize our own needs.”

For Debbie, that meant overcoming self-doubt and doing things that, at the first moment, seemed unreasonable. Writing a book and starting a podcast were among them. With simplicity and the eyes fixed on the higher purpose of helping the audience, she gave it a try. “If you just take a pause and a breath and give it a second thought and say, well, wait a second, why can’t I do that?” she asked herself. “That’s when your life actually changes.”

Debbie teaches us that it’s never too late to “get out of our little bubble.” And if we decide to stay there, “just know that’s what you’re going to get out of life,” Debbie reminds us. “And is that all there is?”

Tell us: What was the last time you dared to do something challenging but fulfilling? Was it worth it?

Carolina Baldin is a freelance journalist from Brazil. Having worked in law, policy and regulation, she is passionate about everyday stories that illustrate larger issues. She graduated from a master's program at Northwestern University in 2023 and became a guest blogger on the "Speaking of Phenomenal" podcast blog in March 2024.