“Don't simply retire from something; have something to retire to.” Harry Emerson Fosdick

Welcome. I'm Roberta Gregoire.

I help people work through the parts of retirement that don’t show up on a spreadsheet.

You can be financially prepared and still feel unsure. That’s normal. Retirement changes more than your schedule.

When Work Ends, Something Else Has to Begin

For decades, work shaped your days. It gave you structure, people to talk to, problems to solve, and a clear answer to “what do you do?”

Then it stops. Even if you chose it. Even if you were ready.

The questions shift. Who am I without the role? What gets me out of bed on an ordinary Tuesday? Where do I want to spend my time and energy now?

Most people plan carefully for the money. Fewer plan for the identity shift. Research bears this out — more than half of pre-retirees expect a smooth transition, yet far fewer describe it that way.

That’s where I come in.

Who I Work With

I work with people in their late 50s, 60s, and early 70s who have had meaningful careers, are financially ready or close, but feel unsettled about what comes next. Some are still working and unsure about when to step away, and others are newly retired and more restless than they expected.

Many are also navigating aging parents, shifting health, or changes in family roles while trying to think clearly about their own future.

I’m in this, too. I’m still working full-time and planning for my own retirement while helping my parents as they age. I understand the pull in both directions.

Retirement gives you back your time. The question becomes: what do you want to do with it?

If you want to think this through deliberately, one conversation is a good place to start.

A Bit About Me

I’ve spent decades in financial services, raised a daughter with a complex medical condition, gone through divorce, and lived with autoimmune illness. Each chapter forced me to reconsider who I was and what mattered.

Eventually, I trained and became a certified life coach and went on to complete specialized training in navigating transitions. In 2023, I was awarded an Impact Grant from the Cystic Fibrosis Foundation to help adults with CF navigate the life changes that came from breakthrough treatments.

People who know me well describe me as curious, caring, and practical. I bring both lived experience and professional skills to every conversation.

Outside of work, you’ll find me digging in the garden, playing with my Beagles, Jolly and Reggie, experimenting in the kitchen, or exploring hiking trails across New England. I care deeply about native plants, the ecosystems we share, and creating a life that feels both joyful and sustainable.

A well-placed question or comment are often all it takes to nudge me in the right direction. - Rich M., MA

“Over the past year, I have been working through multiple transitions in my life. Roberta has been my coach all along the way. Our sessions have become the highlight of my very busy schedule. I know that each time we meet, she will guide me, show me what I am not seeing and help me inch forward toward my goals and dreams. She listens deeply, and creates a space that makes me feel safe and allows me to open up. I'm grateful to have her as my coach as I work through my life transitions.” -Bahija H., CA