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What Seasonal Travel in Alaska Taught Me: Build Skills and Take Them With Me As An Income Stream
I spent my whole summer doing seasonal work aways in Alaska. Working while you travel enmeshes you into the cutlure around you so that you can experience life in your destination to the fullest, but: Everyone seemed to have one common obstacle: How Do I Make Money In Order To Travel? The biggest survival skill I learned in Alaska is to be willing to serve and have a skill that can help you build an income stream, and a great community. In many seasonal travel destinations, having the hands-on skills of woodworking can earn you free housing trades, a way to make income making and selling items in booths or…
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It’s Okay to Miss Things: Learning to Rest Inside the Journey
“I’m not missing anything meant for me.”That thought slipped in quietly as I looked back on my first night in Alaska — the night I didn’t explore, didn’t wander, didn’t savor a single mountain view. The night I, quite literally, collapsed behind blackout curtains like a fainting goat with frequent flyer miles. At first, I judged myself for it.Who flies across the continent, drags 100 pounds of luggage uphill like a sherpa with emotional issues, and then… sleeps through their grand arrival? Apparently, someone human.Someone tired.Someone in a process. And that, as it turns out, is perfectly okay. The Myth of Missing Out There’s this quiet cultural lie humming underneath…
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Stories from the Road: A Workaway’s Diary
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How 100 Pounds of Luggage Taught Me to Travel Lighter in Life
There are moments in life when you pack for a trip… and then there are moments when you pack for the end of the world as we know it. I, apparently, chose the latter when I prepared for Alaska. In my defense, I had never been to Alaska, and I don’t like being cold. Also, there was a volcano warning at the time, so I tucked a chemical filtration mask into my suitcase like it was my birthright. As one does. But the truth beneath all that weight—both literal and symbolic—is that I was scared.Scared to leave home.Scared to be alone.Scared to step into a version of myself I didn’t…
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Empty Nest To Seasonal Work Traveler- Navigating Life Transitions
What does a mother bird feel when she has spent a season preparing a fledgling to fly, only to watch it spread its wings and soar away, leaving behind an empty nest? Do birds feel that mix of pride and aching emptiness that human mothers do? An Empty Nest After years of single motherhood—endless adventures, soggy kisses, muddy handprints on my clothes, homeschooling, cheerleading practice and all the magical chaos that makes motherhood both challenging and rewarding—my little Duck (my name for my only child) finally left the nest. I knew this day would come, and I was excited to see her conquer life on her own terms. Yet after…
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The Joys and Struggles of Work-Travel Lifestyles
Travel can be a tool for personal transformation. It invites us into new landscapes and new versions of ourselves. When you combine travel with work, you get a lifestyle that is equal parts adventure, challenge and self‑discovery. I first dipped my toes into seasonal work‑travel when my daughter “flew the nest.” I needed to rediscover who I was outside of motherhood, and work‑travel offered both a means of income and a path back to myself. Over the past year I’ve discovered breathtaking vistas and new communities, but I’ve also learned how hard it is to live out of a suitcase while supporting myself far from home. Below are the joys…
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Stories from the Road: A Workaway’s Diary
Looking Forward at the journey to come and reflecting back on the experience once it ends are good, but the pages that fill each day of our journey are written each day. Sometimes, the simplest moments hold the deepest wisdom, but we tend sometimes to overlook those simple times. This diary is a peek into the daily life and activities and authentic, raw thoughts of a day in the life of a seasonal travel-worker. Looking ahead to new adventures and reflecting on what you’ve experienced are both valuable, but the magic of a travel‑work journey unfolds in the everyday pages you fill. When you write daily, you capture the little…
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It’s Okay to Miss Things: Learning to Rest Inside the Journey
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How Temporary Jobs Can Fund Your Next Journey
Travelers often dream about seeing the world but wonder how to pay for it.When I first stepped into the work–travel lifestyle, I felt much like you might feel now—excited to chase new horizons yet unsure how to fund the adventure.I soon discovered that temporary jobs can act as a passport to endless journeys.By taking on flexible gigs, travelers earn money, gain skills and immerse themselves in places they’d never visit as tourists. Teaching remains one of the most reliable ways to earn while living abroad.Nomadic travel expert Matt Kepnes notes that teaching jobs are incredibly abundant and often pay well, especially in Southeast Asia (nomadicmatt.com.)Many schools reimburse flights and offer…
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Overcoming Challenges While Working and Traveling
Travel-work life looks magical from a distance—sunrise coffees in new cities, new friends from new worlds, and the thrill of stepping into the unknown. But every seasoned traveler knows that the road also tests you. It stretches you. And—like any pilgrimage worth taking—it transforms you. As Bill Bryson reminds us, “To my mind, the greatest reward and luxury of travel is to be able to experience everyday things as if for the first time.” But that daily beauty only emerges when we also learn how to navigate the challenges that naturally come with working on the move. Below are the five greatest work-travel challenges people face—and the most empowering solutions…
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The Best Countries for Seasonal Work Opportunities
Stepping into a new country alone is equal parts thrilling and nerve-tingling—like the moment right before a roller coaster drops, except you actually chose this one. For solo female travelers, the world is becoming increasingly accessible, with many countries offering safe, structured, and exciting seasonal work opportunities. Whether you want to pour coffee in a mountain lodge, teach English beside the sea, or work the harvest on a gorgeous hillside, the right destination can make all the difference. As travel writer Freya Stark once said, “To awaken quite alone in a strange town is one of the pleasantest sensations in the world.”Especially when that strange town comes with a paycheck,…
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10 Lessons You May Learn From Working Across Continents
Because finding yourself abroad sometimes means losing your socks, your sense of direction, and occasionally your dignity — but always gaining wisdom. Working across continents sounds glamorous in theory: sipping coffee in a new city, sending emails on mountaintops, casually sprinkling foreign words into sentences. But as any seasoned traveler will tell you, the real learning happens in the messy, hilarious, humbling moments no glossy travel blog warns you about. As Pico Iyer famously said, “Travel is not really about leaving our homes, but leaving our habits.”And oh, does working abroad break some habits. Here are the 10 best lessons you’ll learn while working across continents — whether you signed…
Insights Into Worldwide Seasonal Work
