About - Rising Sails

Smiling woman with long brown hair typing on a laptop at a wooden desk in a cozy home office.

Hi, I'm Sherri Webster, LCSW, C-SWHC

I'm based in Dover, Delaware and work with clients across six states. I specialize in helping adults navigate grief — whether that's a devastating diagnosis, a profound loss, or the weight of caring for someone you love — when the fear, uncertainty, and heartache feel impossible to carry alone.

Grief is my life's work — in all the forms it takes.

The loss that stops you in your tracks. The diagnosis that reorders everything. The slow grief of watching someone you love change. The grief of a future that looks nothing like you planned. The grief you're carrying quietly, because life didn't stop to make room for it.

Most of the people I work with are still functioning on the outside. They're going to work, taking care of family, making decisions, answering messages, and doing what needs to be done. But internally, they're carrying a constant background of fear, grief, and uncertainty that doesn't fully shut off.

That often shows up as:

persistent "what if" thinking that won't quiet down
anticipatory grief about outcomes that haven't happened yet
emotional exhaustion from staying composed for other people
fear that feels difficult to explain without overwhelming others
a sense of being alone inside something that feels too big to name

If any of that sounds familiar — you're in the right place.

I have deep specialty in anticipatory grief, chronic illness grief, and caregiver grief. And I welcome anyone who is grieving, in whatever form that takes.

Over the past decade, I've worked extensively with adults navigating grief in all its forms — serious medical diagnoses, chronic illness, caregiver stress, anticipatory grief, and loss. My clinical approach is informed by both long-term experience in healthcare settings and specialized certification as a Certified Specialist in Health Care Social Work (C-SWHC), which focuses on the intersection of physical health crises and emotional impact.

What I’ve seen again and again is that people who are grieving are often expected to “stay strong” while internally feeling overwhelmed, frightened, or emotionally flooded—but without a place where that experience is fully understood without judgment or minimization.

In our work together, the goal is not to rush past what you’re feeling or force a positive frame onto something painful.

It’s to create a place where you don’t have to manage how you feel, translate it for others, or carry it alone.

A place where the fear, grief, and uncertainty can finally be spoken honestly—so you’re not holding all of it by yourself anymore.

You don’t have to wait until things feel unmanageable to get support.
And you don’t have to navigate this kind of emotional weight alone.

I'm based in Dover, Delaware, with deep roots along the East Coast — from the Jersey Shore to the Delmarva Peninsula to the Florida coast. Water has always been part of my story. I grew up walking to a lighthouse, breathing in salty, marshy air, and feeling the particular kind of calm that only comes from being near the bay. My family's connection to the water runs deep — and that feeling, that sense of steadiness and expansiveness you get when you're standing at the edge of something bigger than yourself, is exactly what I hope people find here.

Rising Sails isn't just a name. It's a feeling. The moment when the wind catches and something shifts — when forward finally feels possible again.

If you are interested in scheduling a consult, you can schedule here.

Are you a therapist looking for Clinical Supervision? I offer that too. Let's connect!