Richard Logan Headley, 36, passed away unexpectedly on February 9, 2025, in Portland, Oregon.

Rick was born a naturally kind and compassionate soul, on July 20, 1988. He grew up between Hampton, Virginia, and the Northern Neck. He was a Class of 2006 graduate of Kecoughtan High School in Hampton. Rick went on to earn his bachelor's degree at Virginia Commonwealth University.

In Richmond, Rick worked for Elephant Insurance. Following his move to Portland, Oregon, he served as a Technical Specialist, Individual Annuity Operations, for The Standard.

Wherever he went, Rick worked to forge strong friendships. A soft spoken, kind-hearted man with a sharp wit and a quick laugh, there was little Rick loved more than spending time with friends. He nurtured relationships across the country, through his beautiful talent for making people feel welcomed and valued. His coworkers, friends, and family often looked to him for guidance, as he had a rare ability to see the big picture while empathizing with multiple viewpoints.

A man of many passions, Rick was also deeply connected to the world around him. He loved spending weekends snowboarding, hiking, bike riding, and exploring the beauty of nature. He was as happy sharing a favorite mushroom foraging spot with a friend as he was slinging a hammock alone in the forest to sleep beneath the stars. He thought deeply about those stars, and loved to lead a thought-provoking discussion on the universe that might wander from mathematical theorems to philosophy to pop culture references. Rick saw beauty in everything around him, and worked to share that beauty through photography, painting, sewing, and gardening. Above all, Rick lived fully, with intention, and with a determination to experience all the wild beauty that the world had to offer.

Rick will be forever loved and missed. He is remembered with much love by his mother, Elizabeth (Thomas) Cutshaw; father, Robert (Angie) Headley; siblings Megan (Christopher) Rinderknecht, Robyn (Richard) Frost, Zephyr Headley, and Emma Headley; grandmother, Mary Betty Headley; niece, Madison Rinderknecht; and nephew, Griffin Rinderknecht. He leaves behind a long list of saddened aunts, uncles, cousins, and friends.

A Celebration of Life will be held at R. Hayden Smith Funeral Home at 245 South Armistead Avenue, Hampton, Virginia, on Feb. 28, 2025 at 1:00 p.m.

In lieu of flowers please make a donation in his name to your favorite charity.