5 Hard-Earned Tips for Hawaii Work-Trade (WWOOFing) that ensure Success

During my adventures on these Hawaiian Islands, I have witnessed some remarkably unconventional and intriguing ways of living—ways that aren’t nearly as common on Mainland USA.

The single most profound difference I’ve encountered on these islands is the social agreement known as Work-Trade. Before I came here, I’d never work-traded anywhere. Heck, I don’t think I’d even heard of it before, but it turned out to be the best way for me to live cheaply on the Big Island while I wrote my 2nd book. No joke.

If you’re not familiar, work-trade is a type of living situation where a person (i.e., a work-trader) does a certain type of work in exchange for lodging. This is especially common on Hawaii, where jobs can be scarce. But even beyond that, many people choose work trade for the community benefits it offers. Nowhere else in the world have I seen so many intentional communities thriving than on Hawaii, and many of my friends here believe that community living is the future (not to mention the past, too).

Before I came to Hawaii in April 2013, I thought work-trade would be a fantastic way to save money. After all, helping people with their technology in exchange for free rent, laundry, and internet service sounded like a stellar idea.

What I didn’t know at the time was how much of a growth catalyst this would be for me. I’d never lived in community before, and I was in for a bit of an adjustment. I’ve managed condense what I’ve learned into the five tips below, that, when applied, can highly improve your experience.

Five Wise Tips

  1. Be Totally Crystal Clear what your agreement is before you begin. If the agreement is 24 hours per week, please be sure of which days that entails, and exactly what that work will be. Some managers are more free-spirited than others and just want someone there to hold space, while others will micro-manage you. It’s up to you to clarify what is expected of you before you begin.
  2. Realize that agreements are up for negotiation as long as you keep an open ear and behave honorably. Some places will charge you a security deposit (or give it some other name), and I was able to cut the deposit of my first place in half by doing some extra work in exchange. Normally, this wouldn’t be a big deal, but in a place where jobs and clients can be tricky to find, saving a little extra cash is helpful.
  3. Run the Work Environment through your gut. Do you feel good about living on the same property with the person who will also be your boss? Having your manager also be your landlord is perhaps the largest mental shift associated with work-trade. Working with someone who you get along with is great in a job situation, but it’s just about mandatory when it comes to work trade. You will see that person most every day, so test for resonance before you agree to anything. If you get into an agreement with someone who simply doesn’t get you, anguish will result. However, if your manager understands what you have to offer, and you both do your part, a beautiful, highly-supportive relationship can result.
  4. Be sure you want to be part of that Community before you arrive. If the community is relatively transient, obviously you’d better be equanimous with unexpected personalities coming and going every few weeks. Do you resonate with the culture of the place? Do you enjoy the people there now? Have you noticed new people arriving that you also feel good about—or don’t? In a place with a high turnover rate, like a hostel, this is can be a double-edged sword. Know yourself.
  5. Be prepared to share Utilities like kitchen, laundry machine, and bathroom. If you haven’t had to do this before, it can be a bit of an adjustment, but usually the least of concerns, which is why I’ve placed it here at the end. If you are the kind of person who is interested in community in the first place, you will most likely adapt to this quickly.


Overwhelmingly Positive

Double Rainbow over Hana Bay, Maui

Overall, living in a various work-trade situations has been overwhelmingly positive for me. Once I adjusted, I found the work-trade situations on the Big Island to be intriguing and of a relatively low time commitment (usually less time than a part-time job).

If you’re able to land a place that really resonates with you, it can be the best decision you’ll ever make if you want to really delve deep into a place while travelling, especially in Hawaii. You’ll expose yourself to new growth experiences, many of which you can’t anticipate. Living in a community, no matter how small, has the effect of exposing elements of yourself that you can improve on, as well as revealing your greatest strengths.

A Final Word of Warning: Once you start doing this, it may be difficult to stop! When I started house-sitting in mid-2014 after living in community for over a year, I found the adjustment to living alone rather pleasant at first, but then I came to miss living in community. The social support to be found in community is powerful, even if it’s just one or two other people.

Even now as I write this, I am on the eastern side of Maui, typing inside one of the most terrific living rooms ever: a fully-enclosed geodesic dome, complete with couches and a guitars along the edge. My friend’s farm here in Hana is a wonderfully eclectic mix of sacred architecture, abundant fruit trees, and creative souls — not to mention a wonderful home base for my brief time here on Maui.

Seems I just can’t get away from community, can I? 😉

Why I take the Slow-Burn Approach to Friendships (& even Dating!)

Sometimes, emotions are swept up, you’re in the middle of a grand adventure…

And then you meet someone.

Perhaps this person is unlike anyone you ever met before. Or perhaps you’re just being swept up into the adventure of it all. How can you tell?

Time. Time is the only way, of course.

Time and again I’ve been surprised how my perception of someone can shift over days and months. Occasionally, I’ll meet someone who does a surprising 180°, sometimes for ill and sometimes for the better. In the disappointing cases, my intuition will send me a warning signal. Often the signal comes in through the pit of my stomach or as a buzz in the back of my head. But I always know what it means.

So I manage my expectations. I limit how much their choices might affect me or my journey. And I continue to give them the “benefit of the doubt.” Sometimes that feeling in the pit of my stomach turns out to be less serious than I thought, and people have been known to give uncharacteristic first impressions.

The opposite can be true, too. Have you ever met someone who seemed uninteresting or just plain strange at first, only to grow closer to them later? People judge people by their covers just as they judge books, but there are often chapters that change the entire story.

The Slow Burn

All of this is why I like to get to know someone slowly, like a fire growing over time, before I make any assumptions about if and how they will fit into my life. When travelling, I often tell people that I don’t feel like I know much of anything about someone new after just one day, even if we hang out all day. To form a baseline model for someone’s personality, I need multiple data points. I need to see them in different environments on different days.

I read once that people are like fruit. I really don’t get to see what’s inside until they’re squeezed by circumstance. It’s a fun metaphor, and I think it’s not far from the truth. What I’ve learned about friends in times of strife is usually enlightening, sometimes encouraging, and often vindicating. Certain circumstances reveal totally new chapters within the story. I’m not saying you need to wait for these to happen, but they can be exceedingly valuable in understanding a person on a deeper level.

Tips for Travellers & Stationary People Alike

If you want to establish strong, honest relationships with people, take time before you make assumptions about a person. I’ve often been surprised at how good a friendship can get, or how I can pick up certain friendships right where we left off, as if no time had passed at all. I used to think that a long gap in communication was a sign that we’d grown apart, but now I see it as another element in the ever-complex process of growth that we are all taking part in.

You’ve probably heard the phrase “It’s a marathon not a sprint” and connecting with people is no different. So run the marathon with wisdom and trust your inner guide. Watch the scene unfold as a slow burn. You’ll be glad you did.