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. 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 prepare for changes in identity, structure, relationships, and daily life that retirement can bring.

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.

Retirement opens up possibilities. The question becomes: which ones matter to you?

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

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