Why Rachel Started Grief Trips: The Founder's Story

Why did Rachel Wong start Grief Trips? Because after losing her father in her twenties, she couldn't find a form of grief support that fit how she actually needed to grieve — something between a clinical therapy session and being expected to carry on as normal — so she built one, using the thing that had helped her most: going somewhere else, with people who understood, and having room to just be in it.

A loss that didn't fit the available options

Losing a parent in your twenties sits at an odd angle to the world around you. Most of your peers aren't dealing with this kind of loss yet, which can make grief feel like a language no one nearby speaks. Rachel Wong lost her father during this stretch of life, and in the aftermath she ran into a problem a lot of people in grief eventually run into: the support available to her didn't match the shape of what she was feeling.

There was individual therapy, useful but bounded to an hour at a time, disconnected from the rest of her days. There was the quiet expectation from the world around her that she'd be "back to normal" within some unspoken window. And there was the isolation that comes from grieving something specific and personal in a culture that's generally uncomfortable sitting with loss for very long. None of it was built for someone who needed grief to take up more space than that, without needing it to be fixed.

What she noticed was missing

Grief support in most forms tends to assume one of two shapes: clinical, one-on-one, and scheduled, or informal and left to whoever happens to be around. What was largely missing, in Rachel's experience, was something in between — a space designed specifically for people carrying loss, where grief wasn't the whole point of being there, but it also wasn't something to hide. A place where you could talk about the person you lost, or not, without either choice being read as a signal about how you were doing.

She also noticed how much isolation compounds grief. Not isolation in the literal sense of being alone, necessarily, but the isolation of being surrounded by people who love you and still feeling like you're the only one who understands what this particular loss is like. Being around other people who are also grieving, even people who lost entirely different people in entirely different ways, seemed to loosen something that individual support alone couldn't reach.

Building something with no script

That thinking became Grief Trips, part of Happy Grieving, the wider effort Rachel built around supporting people through loss. The model she landed on deliberately avoids a fixed therapeutic agenda. There's no script dictating how much anyone has to share, no itinerary for feelings, no expectation that everyone arrives at some tidy resolution by the final day. Instead, small groups of roughly eight to twelve people travel together for several days, with daily grief workshops and one-to-one support built in alongside shared meals, free time, and a destination genuinely worth being in.

Most people who join travel alone, which turns out to be one of the model's quiet strengths — strangers carrying different losses, with no history between them to manage, tend to talk to each other with a directness that's harder to find at home. Rachel reads every application herself, in part because getting the group right matters as much as getting the destination right.

Why the destinations aren't incidental

The trips run in Portugal, Morocco, and the Maldives — places chosen for being worth traveling to on their own terms, not as backdrops for a program. That distinction seems to matter to how the model works. A grief retreat that feels like a treatment plan wearing a travel itinerary isn't the same experience as a real trip, somewhere beautiful, that happens to hold space for grief alongside everything else it offers. It's a fitting choice for someone who built this out of her own loss rather than a formula: the destination isn't decoration around the grief work, it's part of why the week works at all.

A model built from what was missing, not a formula

There isn't a dramatic founding story beyond the one that's true: a woman lost her father, found that existing grief support didn't fit, and built something closer to what she'd needed. What Grief Trips has become is less a business plan than an answer to a specific gap Rachel lived through personally — support that doesn't ask you to perform recovery on a schedule, delivered somewhere worth being, alongside people who don't need your grief explained to them.

That's still the model today: small groups, honest space, no fixed script for what grief is supposed to look like along the way.