Episode 80: Living Your Great Life Right Now with Monica 'Moss' Aguilar

What happens when you build your life around the things that make you come alive - not someday, but right now?

Monica Aguilar, known on trail as “Moss,” is an artist, long-distance hiker, and everyday explorer who has intentionally built a flexible life around creativity and adventure. After graduating from UMass Amherst, she spent a season working in Alaska before thru-hiking the Appalachian Trail in 2018. Since then, she’s continued exploring on foot and by bike, including the Pacific Crest Trail and more than 3,000 miles on the Continental Divide Trail.

In this conversation, Monica and I talk about what keeps drawing her back to long trails - the community, the challenge, the highest highs and lowest lows, and the chance to experience a place slowly rather than simply passing through it. We also get into fear and risk, including difficult snow travel on the PCT and the decision to change course in Colorado’s San Juans when challenge began moving beyond her comfort zone.

But Monica’s story is also about designing a life around what matters. She’s built enough flexibility into her work, spending, and art business to disappear onto a trail for months at a time while still saving for what she calls “future Moss.” That philosophy overlaps beautifully with something I talk about often: living your great life right now without ignoring the future.

We also explore the connection between adventure and Monica’s art. Through Chasing Trails Art, she creates murals, window paintings, and nature-inspired work influenced by the places she encounters along the way. Even there, she finds another version of doing hard things - the uncertainty and struggle of creating something that didn’t exist before.

Episode Highlights

• 00:00 — Meet Monica Aguilar: artist, thru-hiker, and unconventional career builder

• 08:30 — Working in Alaska and discovering space for creativity

• 14:00 — Taking on the Appalachian Trail as a relatively new backpacker

• 15:00 — Trail community, rainy days, and learning to embrace uncomfortable conditions

• 18:00 — Solo female hiking, trusting your instincts, and uncomfortable encounters

• 24:00 — Why Monica keeps choosing long-distance trails and hard things

• 25:30 — How “Moss” became her trail name—and why you should apparently pet the moss

• 29:00 — The PCT, CDT, and squeezing every last drop out of an adventure

• 33:00 — Snow travel, fear, and knowing the difference between growth and too much risk

• 39:00 — How Monica financially makes months-long adventures possible

• 42:00 — Saving for “future Moss” while still living for “now Moss”

• 44:00 — Turning nature and travel into Chasing Trails Art

• 50:00 — Why making art can sometimes feel harder than hiking thousands of miles

• 58:00 — Dreaming about a traveling mural tour and combining work with adventure

• 59:00 — Living your great life right now

About Monica Aguilar

Monica Aguilar is a Massachusetts-based artist, thru-hiker, and adventurer whose travels inspire much of her creative work. She has thru-hiked the Appalachian Trail and Pacific Crest Trail and completed more than 3,000 miles on the Continental Divide Trail. Through Chasing Trails Art, Monica creates murals, seasonal window paintings, and nature-inspired artwork drawn from the landscapes and experiences she encounters along the way.

Connect with Monica Aguilar

• Chasing Trails Art

• Instagram

• Facebook

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Hosted by Josh Self, financial advisor and everyday explorer.

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