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? 😉

How to Get Paid to Drive 1,000 miles (Craigslist Rideshare Step-by-Step Guide)

If you want to become more confident, more flexible, and live a more inspired life, travel is one of the very best uses of your time.

I’ve found this to be especially true last year when I traversed over 6,000 miles exploring around the western United States. Along the way, I realized people’s limiting beliefs tend to highly limit to what they think they can do.

I realized that people usually perceive travel as being a luxury, something prohibitively expensive and best experienced in short one or two-week bursts.

To that I say: Dingo’s Kidneys!

The reality is that there are lots of ways to travel to the destination of your dreams without spending nearly as much money as you think. So today I’m going to explain my method for dramatically reducing the cost of travelling from Point A to Point B, as well as how you might even make some money from doing it, like I did.

6,000 Miles of Success

Last year, I utilized Craigslist with great success. In fact, about 90% of those 6,000 miles mentioned above were traversed through Craigslist rides. If you’re not familiar with Craigslist, it’s a website that allows you to post classified advertisements to easily get a lot of eyeballs on what you have to say, usually a request or an offer of some sort. With the exception of a few select categories like real estate for the most populous cities, Craigslist ads are completely free to post.

You may already be familiar with areas on Craigslist that help you find housing or sell your car, but increasingly people are using it to find carpool and rideshare partners. By using the Craigslist rideshare page, I was able to travel thousands of miles around the western half of the USA without having to worry about bringing a car along (and all the maintenance, parking, and security concerns that arise from that). And I plan on doing this again in the future.

Does the thought of using Craigslist to share rides seem strange to you?

Why should it? Many many people around the world do this exact thing every day and benefit greatly from it. I’ve used it for about two years and have never had a negative experience using it. I originally found out about this section of Craigslist via word of mouth, and judging from how it’s grown over the past year, people are recommending this service to their friends more and more. Perhaps it’s because the people I’ve met through Craigslist are very kind and more open than the average person you’d meet. They have families and friends just like you, and they’re just trying to save some gas money as they go from Point A to Point B. That’s why the system works. So now that you know why, let’s talk about how.

How Craigslist Rideshare Works:

  1. Go to www.Craigslist.org
  2. Watch the site automatically redirect you to the Craigslist page for the city nearest you. Or you can choose a specific city from the: Craigslist Sites List
  3. Click “rideshare” under “community”, which is on the top left. (Alternatively, you can just add “/rid/” to the end of the URL.)
  4. Browse the listings and find a ride going where you want. (You may also want to use your browser’s “Find” function to search for all instances that your destination’s name appears on the page.)
  5. Click the email link above the entry and email the driver that you’re interested in sharing a ride with.
  6. Repeat Steps 5 & 6 a few times to increase your chances for a quick response.
  7. Wait.

Sometimes people who post rideshare ads won’t get back to you for a few days, so if they provide any other contact info besides the anonymous email address that Craigslist provides, try contacting them via that method first. I’ve found that people are more responsive to telephone than email.

In addition, you can also post an ad of your own, free of charge, on Craigslist to request or offer a ride. Just be sure to post in the Craigslist site for the city you’re departing from. And if you’re really in a hurry, I recommend you do both: post an ad requesting a ride as well as email anyone offering a ride to your destination. Doing both will dramatically raise your chances of leaving sooner.

Once you’ve contacted someone via email or exchanged phone numbers, plan a time to meet up before your carpool. This isn’t always possible, but it’s recommended for journeys longer than a couple hours. Usually fuel expense is split evenly between all people who will be riding, but occasionally a generous driver will offer a ride free of charge. (Some people just want conversation during a long ride.)

So how could you actually make money from this?

The way I made money using this amazing service was initially accidental. I had been checking Craigslist for a few days, trying to find a ride out of Denver to the Chicago area. Sometimes, around holidays especially, finding a ride to a distant city can take a week and occasionally longer. That’s why it’s important to have a backup plan (or be more flexible), however I’ve found that timing tends to work out for the best in the end.

This case was no exception. I found a posting on Craigslist by a woman who was moving from Denver to Chicago, but she didn’t enjoy driving on the freeways. “What a great circumstance,” I thought. “I’m completely happy to drive on freeways, and I’m headed exactly that way.” After exchanging a few emails, I called her up and planned a time to meet up with her.

I had been using Craigslist for years before this, and this was the first time I had the opportunity to be the driver. Unless you’re using your own car, being the driver is quite rare, and about 99% of all ride offers do not require you to drive, or even have a drivers license.

Run Craigslist riders past your Intuition

Just as with any new person in your life, it’s important to run prospective passengers and drivers past your intuition (what some people think of as their “gut feeling”). Although some people tend to judge on appearance, I’ve found that even more important than appearance is the feeling a new person gives you. How do you feel after you’re done talking with them? Tired? Neutral? Confused? Energized?

A phone call is a great way to start, so when I called her up, I paid close attention to how her presence made me feel. What does my intuition say about this person? Do I feel he/she is trustworthy? Is this the kind of person I’d feel comfortable sharing a car ride with for the duration of my trip?

After running it past my intuition, I got a green light. I felt good and scheduled a time to meet up. By meeting up in person, my intuition would have a lot more data to go on, and I’d be able to examine the car I’d be driving. When I met her in person, my intuition gave me another green light, her little car started up right away, and I had a good feeling all around. After asking her some questions about the vehicle’s condition, I concluded that it was ready for the 1,000 mile journey ahead of us. (It’s worth noting that, if you’re the driver, it’s a good idea to make sure your vehicle is up to the task BEFORE you embark.)

How I Got Paid to Travel using Craigslist Rideshare

Here was the deal: In exchange for driving us all the way to Chicago, she would pay for all of the fuel and also offered to pay me a bit of money (a delightful $50) for my time. I was surprised. I’d never been a paid chauffeur before, and because I didn’t see the work as being that challenging, I didn’t see it as something that provided that much value. This mental association with non-challenging work not providing much value was false, of course. I realized that since she didn’t feel at all comfortable or capable of driving on high-speed highways, I was providing a good deal of value, but I told her she could pay me whatever she felt was fair.

To be honest, at that point I was still so pleasantly surprised at how things were working out — still rather amazed at that the universe brought me an opportunity to go 1,000 miles for free — that anything beyond that was metaphorical icing on my metaphorical travel-cake.

North America Map showing Route from Denver to Chicago

And So I Drove All 1,000 Miles… in One Day

We were both lucky to have found each other, and without Craigslist this never would have happened. If she hadn’t found me, she said she would have had to pay for another driver’s plane ticket back to Denver. Lucky for her, I was heading back home; and lucky for me, she was heading my way.

We set out as early as possible, and I drove the entire 1,000 miles in about 17 hours. It would have been faster, but she had a dog, and dogs have needs. (Note to self: Intend that no future rides involve pets that have to stop for “bathroom” breaks every few hours…)

But all things considered, it worked out incredibly well.

Expand your Comfort Zone

Doing something like using Craiglist rideshare to find a carpool partner may be beyond your comfort zone right now, but that doesn’t mean it’s a bad idea. You have a lot more freedom that you realize; and in my experience, the worldview you’re used to seeing on TV is not an accurate representation of what America (or the rest of the world for that matter) is actually like.

Just turn off your TV and see the world is nicer than you thought.
~ Elijah Wald

As I said at the beginning of this article, many many people do this around the world every day, and every Craigslist experience I’ve ever had was positive. These are people with families and friends, just like you. These are people who are trying to get from Point A to Point B, just like you. That being said, if you’re going on an especially long trip like I did, it would be wise to meet up with the person beforehand to make sure you’d be comfortable being in the car with them for most of the day.

But remember, that they would use Craigslist to find a ride says something about them as a person. It says something about their beliefs about the common goodwill between people and the confidence that they have in themselves. The amount of people using this service who are really fearful or untrusting is very low, and that’s something I like about it.

And although I can’t comment (yet) on how effective Craigslist is outside of the USA, I’ve heard that it’s useful in Europe, as well. As I said before, the people I’ve met through Craigslist are usually very kind and more open than the average person you’d meet. Obviously, we all use Craigslist at our own risk, and not everyone who uses it is going to be a kind person, but my experience with it has been very positive. In fact, every Craigslist ride I’ve ever had has felt safer than being on a city bus, and how many people ride the bus every day without even thinking about it? I guess that explains why people who have used Craigslist rideshare once tend to use it again and again: because they have positive experiences with it!

Who knows, perhaps someday we’ll live in a world where no one has to utter the word “Greyhound” ever again. What a world that would be…

Step Into the Freedom that was Always There

Why not open yourself up to travelling via Craigslist instead of driving next time you have to travel between large cities? Or even smaller ones? You’ll be saving a lot of fuel (which is environmentally responsible) and you’ll be stretching yourself a bit. Who knows, a new friendship might even arise from it!

Have you ever noticed that crossing beyond your comfort zone gives you a rush, sometimes lasting a few days afterward? You get this feeling because a part of you knows expanding your comfort zone is for your higher good (and one of the best uses of your time).

You have a lot more freedom than you exercise. So start stepping into that untapped freedom today, while you still have the chance.

The whole world calls out to you.