Dana Olivo Dares You to Dream
By Melissa Karen Sances | Photos by Nikki Gardner Photography
Published In Northampton Living | February 2026
Dana Olivo doesn’t know who she wants to be when she grows up – but she’s enjoying figuring it out. A certified life coach, Olivo’s niche is women who, like her, may have spent a lot of their adult lives taking care of others – and are now turning the focus on themselves.
“I love witnessing other people’s transformations,” said Olivo. “I don’t think we give ourselves enough credit in our adult lives that we still have things to learn and know.” Noting the skyrocketing popularity of self-help books and podcasts, she continued, “People crave wanting to know more about who they are and how they fit into the larger landscape of the world.” Ideally, self-knowledge begets self-compassion, which begets self-care.
Unlike a therapist, who can help someone mine the past, Olivo said that a life coach has her eyes on the future. She asks clients a lot of questions, but is clear that she doesn’t have the answers. “I don’t live their life,” she said, “but I might be able to gain insight from the things that people say and the things that aren’t being said.”
Olivo, who grew up in Maryland with family that worked in the federal government, knew she wasn’t destined to hop on the metro and commute to Washington, D.C. But after studying sociology and human development at Boston College, she tried returning home and doing exactly that, working from an office cubicle for one year. “It was just … not for me,” she said. She yearned for something more.
Returning to Massachusetts in 2005, Olivo began a career in student affairs at Wellesley College, Hampshire College, and now Smith College, where she’s worked for the past 10 years. Through mentoring students, she came to the understanding that life doesn’t follow a set path. “You shouldn’t have it all figured out when you’re 19,” she said. If a student insisted that they did, Olivo would impart the wisdom that she’d end up sharing with the next generation, too: “That’s cute, but I guarantee that you don’t and you may never, because we’re always going through transition.”
Olivo did her first coaching training in 2018 through the CaPP Institute, which stands for coaching and positive psychology. She ended up connecting with someone remotely that shared her desire to help middle-aged women find what brought them joy, and the two worked on a podcast together before their lives filled up. In the process, she realized that many women have been conditioned to ignore what might bring them simple pleasure – and to endure relationships that are soul-sucking. “I enjoy my own company a lot,” she said, “and if I’m going to be with someone, I have to enjoy them as much as I enjoy myself.” (And her dog – a lovable Husky Lab mix named Coco.)
Sometimes the scope of change can be overwhelming, so Olivo helps women reign in their desires (or fears) and set actualizable goals. “Sometimes we think so big,” she said. “You might say you want to sail to the moon, but maybe all you want to do is touch a cloud.” She often helps women explore their career, their relationships, how they parent, and skills they might like to learn.
A mother of two “magical” teenagers, Olivo can’t help but notice that her kids are often asked what they want to study in college, but that adults “are not encouraged to dream and ideate about our lives in the same way when we reach a certain point.” She has started to consider what she might like to do when they leave home. She has always wanted to live in another country.
But, for now, she’s a fan of Northampton. She loves spending time at Sub Rosa, a botanical lounge and flower shop in the city. Olivo is also a coffee lover, and is appreciative of all the options in town. In the warmer months, she enjoys Summer on Strong, the summer-long party on the popular side street. That said, she appreciates the calmness that takes hold of the city after the students have gone home for the summer.
“Something happened when I turned 40,” she said. “It’s not that I don’t care about other people, but I’m caring a little more about myself.” As she guides other women to do the same, she gives herself permission to dream.
Other Articles from this Issue
