What I Wish I Knew Before My First Workaway Experience

When I signed up for my first Workaway experience, I had little idea of what I was getting into. I had just quit my job, won a free flight to the U.S., and decided to see how far I could go without burning through my savings. What I found wasn’t just a way to make travel more affordable — it was a completely different way of living.

Since then, I’ve done Workaway exchanges in three very different corners of the world: a yurt village in remote Alaska, a farm ranch in Arizona, and a family apartment in Athens, where I lived and helped out as part of their daily life. Each one taught me something new — about travel, about people, and about the kind of life I actually want to build.

Some of my Workaway experiences were unforgettable. Others turned into workaway bad experiences that tested my patience — but even those taught me something.

I’ve been exploring the world for over 12 years, and in 2024, I finally made it official: I went full-time. And if you’re here — curious, maybe a little nervous, wondering if a Workaway experience is right for you — I want to help you start with more clarity than I had.

This post is part honest reflection, part practical guide. It’s everything I wish I knew before hitting “apply” on my first listing — the kind of insight you only get from actually doing it. Whether you’re deep in planning mode or just daydreaming for now, I hope these 17 lessons give you the confidence to go for it — and the wisdom to make it meaningful.

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17 Things I Wish I Knew Before My First Workaway Experience

1. Know Why You’re Doing This in the First Place

When I first signed up for Workaway, I’ll be honest — it was mostly about the budget. I wanted to keep traveling without draining my savings, and the idea of free accommodation in exchange for a few hours of help sounded like the dream.

But it didn’t take long for that motivation to evolve into something deeper. The more I did it, the more I realized: Workaway wasn’t just helping me travel longer — it was helping me travel better. I could slow down, stay in one place for weeks at a time, and actually rest between sightseeing days.

I wasn’t just seeing the postcard version of a place. I was living in neighborhoods, picking up local routines, learning cultural quirks, and finding those little insider tips you don’t get from a guidebook.

So before you even start browsing hosts, take a moment and ask yourself: Why are you doing this? Is it purely to save money? To live like a local? To try a new lifestyle? There’s no wrong answer — but knowing your “why” makes it easier to find the right experience.

Because here’s the thing: the right host isn’t just the one with the best perks — it’s the one that aligns with what matters most to you. One traveler might prioritize a private room and quiet evenings. Another might care more about community, cultural immersion, or local tours. Your level of satisfaction will depend less on what’s offered, and more on whether the experience meets the needs you value most.

And if you’re still figuring it out? Try it once. Prep as much as you can, then go in with an open mind. Worst case? You learn it’s not for you. Best case? You learn something new about yourself — and how you want to see the world.

2. It’s Called Workaway for a Reason

Let’s get this out of the way early: Workaway is not a free vacation. It’s an exchange. You work — and in return, you get a place to stay (and sometimes meals, tours, or local experiences). That doesn’t mean it’s not amazing — but it does mean you need to show up ready to help.

During my Workaway experiences, I’ve done housekeeping in a yurt village in Alaska, brushed horses and walked dogs on a ranch in Arizona, and helped clean an apartment in Athens. The tasks were usually simple, but it was still work — sometimes tiring, sometimes repetitive, sometimes confusing, and definitely not glamorous.

That said, there were moments that made it all worth it. In Alaska, I worked from 11 a.m. to 3 p.m. cleaning cabins and toilets — and by 4 p.m., I’d be ice hiking or cruising (or helicoptering) past glaciers. It was one of the best Workaway experiences — the kind you see on Instagram reels — a half-day work in the morning and a bucket list adventure by afternoon.

But not every Workaway experience is that balanced. In Athens, the apartment had an infestation, and the work ended up being more intense than expected. I was so exhausted that even walking around the city afterward felt like too much. And in rare cases, when the work feels draining and there are no other benefits besides a free stay, it can leave you wondering if it’s really worth it.

That’s why it’s so important to go in with realistic expectations. Yes, you’ll get to explore, connect, and have unforgettable moments. But you’ll also be working — so choose hosts carefully, know your limits, and don’t be afraid to ask for clarity upfront.

If you’re still unsure about how it all works behind the scenes, I break it down in this guide on how work exchange really works.

3. Not All Hosts Are Created Equal

It’s easy to get swept up by nice-looking listings — mountain views, farm-to-table meals, photos of smiling volunteers around bonfires. But not every Workaway experience plays out exactly the way it’s described.

Most hosts genuinely offer what they say — but sometimes, it’s not 100%. Maybe they mention city tours, but you arrive during a busy season and they don’t have time. Maybe they usually cook with volunteers, but this week they’re swamped.

On the flip side, some hosts go above and beyond — I’ve had hosts bring me to concerts, treat me to restaurants, or cook steak just to share something special.

Good reviews don’t guarantee a good match — and bad ones don’t tell the whole story either. Look at recent reviews, not just the star ratings. Pay attention to patterns, tone, and gaps. Ask yourself: is the host clear about what they offer and expect? Have multiple people had positive, balanced experiences?

And sometimes, it’s not about the listing being misleading — it’s just about fit. One traveler might love rustic farm life with animals and outdoor chores. Another might feel more at home in a hostel with shared spaces, social vibes, and structure. Neither is wrong — but you’ll enjoy the experience way more when it suits your style and energy.

If you want a real-world example, I break down the different kinds of hosts I stayed with during a full year of volunteering. It’s a good peek at what a range of host styles actually looks like.

Take your time reading listings. Ask questions. And if something feels off, trust yourself — even if the pictures look amazing.

4. The Application Matters More Than You Think

I didn’t just get lucky with my first applications — I strategized and put in the work. I carefully wrote each message, tailored it to the host, and made sure it reflected who I really was.

The result? I was accepted within 24 hours and finalized my entire five-month volunteering journey in just one week. But not every traveler takes that approach — and many wonder why they’re not hearing back from hosts.

Your application is your first impression. It’s not just about getting accepted — it’s about making sure the experience is a good fit for both you and the host. The best connections feel like a conversation, not a transaction.

Here’s what works best:

• Personalize your message. Mention why you’re excited about their specific listing — not just that you’re “interested in helping.”
• Share a bit about yourself. Who are you? What are your strengths? What past experiences could be helpful in this role?
• Keep it warm, honest, and human. You’re not writing a corporate cover letter — let your real voice come through.
• Ask thoughtful questions. It shows you’re already thinking of this as a shared experience, not just a free place to crash.
• Don’t overpromise. Be clear about what you can offer — and then actually show up and deliver.

A solid application doesn’t just help you get picked — it helps you get picked for the right reasons.

🤩 Ready to find your first Workaway? Get an extra month of Workaway when sign up with this link!

5. You Need to Ask Way More Questions Than You Think

One of the most important lessons I’ve learned with my Workaway experiences is this: you’re not just visiting — you’re living there.

So before you confirm anything, picture yourself waking up there, working there, eating, resting, and sleeping in that space for a week or even a month. Then go back to the listing. Does it actually tell you everything you’d want to know to feel ready?

Often, it doesn’t. That’s why you need to ask way more questions than you think.
Ask while you’re applying. Ask during the interview. Ask again if something pops up afterward — even after you’ve already confirmed.

Some things might seem minor at first, but trust me: small gaps in communication can lead to big surprises. If something crosses your mind — ask. Even if it feels silly. Even if you’re worried about seeming high-maintenance.

• What are the exact working hours and days off?
• Where will you sleep? With how many people?
• Are meals included? Can you use the kitchen?
• What are the house rules? Quiet hours? Wi-Fi limits?

The more you know, the better you’ll be able to prepare — and the more likely you’ll walk into a setup that actually supports you, not surprises you.

You’re not being difficult. You’re being responsible.
This is your time and energy too — treat it like it matters.

I have the complete list of Questions to Ask Your Host Before Confirming in this article — feel free to use it as a checklist before saying yes to any host.

7. Tasks Might Be Different Than You Expected

Even if the listing sounds clear, real life is rarely that tidy. Tasks shift. Hosts get busy. Priorities change. What you thought you’d be doing might not be exactly what you end up doing.

At one of my Workaway experiences, the tasks were listed as “child care, social media, and light housekeeping.” But because of an unexpected infestation, I ended up vacuuming almost every day — far more cleaning than I anticipated.

In another, I signed up to take care of horses and dogs. While I did that everyday, I also found myself cutting down mesquite — those thorny desert plants — and helping drill rock-hard soil to build a paddock where the horses could roam.

None of that was bad — it was actually kind of satisfying in its own way. But it reminded me how important it is to stay flexible. Hosts really value volunteers who can adapt and pitch in where help is genuinely needed.

That said, there’s a line between being flexible and being taken advantage of. If your Workaway experience starts to feel off, unbalanced, or way beyond what was originally agreed on — speak up. Good hosts will understand.

8. Living Conditions Can Be… Let’s Say “Character-Building”

You don’t need luxury to be happy while volunteering — but you do need a basic level of comfort, hygiene, and personal space. That’s something I learned the hard way.

In Jordan, I stayed in a traditional house in the desert with a local Bedouin family. They did have a guest room — but they warned me it gets extremely hot during the day. So I ended up sleeping in the living room instead.

My host was a tour guide, which meant he’d wake up at 6 a.m. to prep for clients, and come home around midnight. Since the front door opened right into the living room, I was the first person he saw every morning… and usually the one getting woken up several times a night. I adapted, but to be honest — I wouldn’t want to go through that again unless I really had no other choice.

Ask about the sleeping setup. Ask about bathrooms, privacy, heating or AC, kitchen access, and whether you’ll have your own space. Because in any Workaway experience, once you’re there, it’s much harder to change — and the small stuff? It adds up. It affects your energy, your rest, and your ability to actually enjoy the experience.

Volunteering can be beautiful, humbling, and deeply meaningful. But don’t romanticize it. If the living conditions don’t work for you, that doesn’t make you picky — it makes you human. You deserve to feel safe, rested, and respected where you stay.

9. Work-Life Boundaries Can Get Blurry

When your home, job, and host are all in the same space, the lines between “helping out” and “being available 24/7” can fade fast. And if you’re not careful, you might find yourself working during your time off or feeling guilty for taking space.

This happened to me more than once — especially in smaller family-run places where the vibe was more casual. I’d finish my shift, but since I was around, I’d get asked for “quick help” or get pulled into extra tasks. Sometimes I didn’t mind. But other times, I ended the day feeling drained, even on my “day off.”

Here’s what helps:

• Stick to the hours you agreed on. Be generous, but don’t feel guilty about your boundaries.
• Plan your personal time. Go out for a walk, read, or explore — even if no one else is.
• Communicate clearly. If things start to shift, talk about it kindly and early.

Workaway is an exchange, not a sacrifice.
Protecting your time doesn’t make you selfish — it keeps the experience sustainable.

10. You’ll Learn as Much About Yourself as the Place

One thing I didn’t expect from volunteering abroad? How much it would teach me about myself.

Yes, you’ll learn about different cultures and ways of living. But you’ll also learn what you value. What you can tolerate. What energizes you — and what drains you. You’ll see how you respond to discomfort, unpredictability, and awkwardness. You’ll learn when to speak up, when to go with the flow, and when it’s time to walk away.

Volunteering strips away a lot of the distractions of traditional travel. You’re not just sightseeing — you’re participating in someone’s day-to-day life. And in that space, growth happens fast.

It’s not always pretty. But it’s often powerful.

11. Not All Platforms Are Created Equal

I started my volunteering journey on Workaway. But the more I traveled and talked to other volunteers, the more I realized that each platform has its own personality, strengths, and level of support.

Workaway has a huge variety of hosts, but it takes a very hands-off approach. Once you connect with a host, you’re mostly on your own. That can work well if you’re confident, flexible, and have some travel experience — but for beginners or solo travelers, it can feel a bit overwhelming.

Later on, I tried Worldpackers — and I noticed a big difference. The platform has a cleaner interface, doesn’t filter out negative reviews, and even offers support if something goes wrong with your host. It felt more transparent, beginner-friendly, and safer overall.

If you’re still deciding which platform to use — or you’re curious about other options beyond Workaway — I’ve compared the 19 Workaway alternatives in this guide.

12. The Best Workaway Experiences Come From Clear Expectations

The most fulfilling Workaway experiences I’ve had weren’t the just ones with the fanciest perks or the dreamiest locations — they were the ones where everyone knew exactly what to expect.

Clear communication from both sides makes everything smoother:

• You know what time to start and finish.
• The host knows what kind of help you’re excited to offer.
• The perks you expect to receive
• There’s no weird guessing game about boundaries, chores, or downtime.

In Alaska, my host clearly outlined our schedule from day one: cleaning from 11 a.m. to 3 p.m., then free time afterward. That structure gave me space to plan hikes, take glacier tours, and even rest when I needed to — no guilt, no confusion.

Compare that to a vague listing that just says “help around the house,” and you can imagine the difference.

Ask. Clarify. Confirm. Clear expectations are what turn good exchanges into great ones.

14. It’s More Than Just a Free Stay — It’s a Lifestyle Shift

I started Workaway because I wanted to travel longer without going broke. But the longer I did it, the more I realized this isn’t just a clever way to save money — it’s an entirely different way of moving through the world.

Volunteering forced me to slow down. To stay longer in places, get to know locals, take rest days between big adventures, and actually live in a place instead of just passing through. It also taught me to value things differently: time over money, community over convenience, experiences over itineraries.

It’s not always easy, and it’s definitely not glamorous — but if you’re craving a more intentional, grounded, and sustainable way to travel, this lifestyle just might change you.

15. Not Every Day Will Be Magical — and That’s Okay

Some days are slow. Some are exhausting. Some feel flat-out weird.

I’ve cried in a comfortable queen-size bed. Felt homesick while eating alone in a shared kitchen. Been too tired from vacuuming floors for the fourth day in a row to go on a hike I was genuinely excited about. That’s real. And that’s okay.

You don’t need every day to be incredible for the overall experience to be worth it.
Volunteering, like life, is made up of moments — not all of them are photo-worthy. But over time, the quiet ones, the tough ones, and even the awkward ones blend into something real.

Let go of the pressure to make it all perfect.
You’re not failing if you’re not smiling all the time. You’re just living.

16. You Might Not Want to Travel Any Other Way Again

After a while, the idea of paying $80 a night for a hotel or rushing through cities with a packed itinerary just… didn’t appeal anymore. Once you’ve lived with locals, learned their stories, and shared morning tea before starting your day — it’s hard to go back to being just a tourist.

This kind of travel is richer, slower, and often way more meaningful. You trade luxury for connection, and convenience for character. And honestly? You probably won’t miss the hotel breakfast buffet.

If this way of travel speaks to you, I’ve shared some of my favorite slow travel destinations that will change you forever.

17. You’ll Leave With Stories You Can’t Make Up

Whale watching after scrubbing toilets. Deep sea fishing in the morning, then somehow ending up in a helicopter flying over glaciers by the afternoon.

Preparing sandwiches and trail mix for people you met three days ago — and somehow trusting them with your life on a 22km hike. Crying in Arizona over roommate drama… and laughing about it months later over wine and grape juice on a completely different continent.

These are the souvenirs that don’t fit in your backpack — but they’re the ones that stay with you the longest.

So… Is Workaway Worth It?

Absolutely — if you’re open, curious, and willing to show up.

It’s not always easy. It’s definitely not always comfortable. But if you’re craving something deeper than sightseeing — something real, raw, and wildly human — this way of travel might just change everything.

You’ll work. You’ll grow. You’ll cry a little. You’ll laugh a lot.
And you’ll come home with stories, friendships, and a version of yourself you didn’t know existed.

Ready to Start Your Own Workaway Experience?

I’ve put together some resources to help you get started with confidence (and avoid the mistakes I made):

• Want to compare platforms? Check out 19 Workaway Alternatives — including the ones I personally trust.
• Need help choosing a host? I break it all down in Is Worldpackers Safe?, including red flags, safety tips, and the exact questions to ask before confirming.
• Ready to sign up? Get an extra month of Workaway by signing up here, or enjoy $10 off Worldpackers (my go-to volunteering platform) with the discount code: HAPPINESSONTHEWAY.

And if you’re still unsure? Try one experience. Just one.
Because the first step is the hardest — but it might just lead you to the most unexpected version of freedom you’ve ever felt.