All about Ray Wood


“What do you mean I can’t work here and I can only stay for six months?”

The Immigration officer at Toronto’s Pearson Airport was very matter of fact. He wasn’t smiling and he was wearing a black bullet proof vest and a pistol on his hip.

It was 2008 and I had just landed on a one-way ticket because I wanted to be with my kids.

My wife and I split after 19 years living in Melbourne because the magic had gone and we wanted to do our own thing. Life happens.

After we separated and sold our home, she wanted to spend “a year or two” back in her native Ontario with the kids.

“So you’re coming back right? I don’t need to ask you to sign anything do I?”

My teenage son Sam gave me this card for my birthday a few weeks before they left for Canada.

Three years came and went.

She’d found a great job with the bank, bought a nice home and the kids were settling into a new school with new friends and new lives. Lives without me!

So at the age of 48, I sold up everything, packed up my treasures and headed for Canada.

I wasn’t pissed or angry. What’s the point. I wasn’t that guy.

I’d been making regular trips but if you’ve ever traveled from Melbourne to Toronto, you’ll know that you need to allow a full 24 hours for flights and layovers. It’s quite the trek.

But I missed my kids so much and wanted back in their lives. I missed being a dad too much. The two week stays were just too short and the goodbyes were brutal.

So here I was in Canada with a 6 month Visitor’s Visa, no job and no legal permission to get one.

I’d saved a little from the sale of my home and car but I didn’t have money to burn.

The Canadian banks wouldn’t lend me money to buy a home because I had no local income record.

I couldn’t even get any health cover, but I didn’t care. Nothing was going to stop me from being with my kids. However, I needed cash and I needed it fast.

So how does a guy approaching 50 start again almost from scratch. There were many sleepless night when I wrestled with this but the thought of being back in my children’s lives over rode everything. I stayed focused on that single objective.

Long story short, I put my real estate skills together and built a membership site called Bestagents. Then I started to hustle like my life depended on it.

My Australian and New Zealand clients didn’t care that I was on the other side of the world. I learned new skills and leveraged some incredible technology to build an exceptional business that provides a regular recurring monthly income.

Fast forward to today and I have a life I never dreamed possible.

Bestagents continues to thrive and we’ve just launched our branded office concept.

I’m a partner in a software start up out of Sydney called LockedOn (freakin awesome real estate software)

And I assembled all my very best real estate tools online and offered them as digital downloads at Rays Greatest Hits

My consulting and coaching business is on fire and I speak regularly about Working From Roam and helping others do the same.

I’m writing this on January 26 which, as all Aussies know is Australia Day and it’s really the one day of the year that really makes me more homesick than ever.

But Canada is not a bad consolation prize.

Did you know there are more than a million lakes in Canada?

A few years back I found a very special one about 2 hours from Toronto and I thought how awesome it would be to own a cottage on that lake.

And on that very same lake I met a special woman and fell in love.

Christine and I got married and built a ski chalet just north of Toronto.

Then we realized our dream and bought a cute little cottage on the lake we both love so much.

I made a quick video about the lake and the cottage and posted it below.

So what have I learned from all this?

  • I’ve learned that almost anything is possible if you commit to a plan of action
  • I’ve learned that giving energy to grudges and regret is pointless and will eat away at your soul (and probably give you cancer)
  • I’ve learned that following your intuition pays huge returns in business and in life
  • I’ve learned that being in love is without doubt the greatest thing on earth
  • I’ve learned to ask for help when I need it
  • I’ve learned that we make our own luck and nothing happens by accident
  • I’ve learned that we only get one life and I’m spending mine doing exactly what I want.
  • I’ve learned that great experiences are worth 1000 times the money they cost
  • And I try to make everyone I meet feel great because great things happen when you do that.

So, it’s the Cottage in the Summer months, the Chalet in the winter and we also have a cool apartment in Toronto right on lake Ontario that looks due East towards downtown and the CN tower.

Looking east from our place towards Toronto, a very special city. Some afternoons, the reflected sunset is spectacular on downtown

In the summer we ski and fish and make awesome feasts with friends.

In the winter we ski and snowmobile and make awesome feasts with friends.

I’m into mountain biking, playing guitar, snowmobiling (epic fun) coffee, discovering cool live music venues and tucked away restaurants in and around cities like Melbourne, Toronto, San Francisco and NYC.

I get to travel a lot each year, usually with Christine and love the Caribbean, especially Cuba which has some of the best beaches in the world and is a brilliant place to hang out and dive with the turtles. (Cubans are the Filipinos of the Caribbean. Magic people)

We love Skiing in Quebec and Whistler, Amsterdam and exploring Australia.

We try to stay at Airbnb homes and apartments whenever we can and have been hosts for a year now. It’s such a cool and responsive app!

Here’s The Chalet listing on airbnb.

Ray Wood

A Message from Ray

Hello and welcome to Working From Roam.

I’m the first to acknowledge that this life is not for everyone.

In fact, to most people, it’s such a departure from a regular job and lifestyle that it boggles their mind.

But I’m living, breathing proof that it’s possible and I want to tell you it’s more doable than you might think.

Every day, people of all ages are discovering the Working From Roam life.

They walk to the beat of their own drum and live a life they didn’t believe was possible just a few years before.

Yes, there is hard work involved and something of a steep learning curve to acquire the skills needed to build a passive income. But isn’t something so awesome worth a little hard work?

I think it all comes down to your self-concept and how you see your life unfolding from this day forward.

There are a million adventures and experiences waiting to be discovered and if you buy in and commit to this idea of a remote lifestyle, it’s amazing what can happen in a very short space of time.

When you’re young, you have this concept of your whole life stretching out endlessly before you.

But as you get older, you realize this deal is finite and nobody is getting out alive.
You start to think about your bucket list and things you have promised yourself you want to experience.

Your ‘life’ clock is ticking.

I’m into adventure and cool experiences so a few years back, I made the decision to start working on my list.

I’ve sailed a 40 foot yacht around Queensland’s Whitsunday Islands.

I’ve dived coral reefs in The Caribbean and Indonesia.

I’ve ridden my mountain bike through rattle snake infested valleys in Utah (Yikes! Both feet off the pedals!)

And I’ve explored the canals of Amsterdam skippering my own boat.

I’m not really interested in back-packing around India for 6 months but I could if I wanted.

I’d rather find a deserted beach on a remote Cuban island and catch fish.

These are my choices. What are yours?

All I’m suggesting is you start thinking ‘what if?’

If every journey starts with a single step, my Tools & Resources Guide is designed to help you start the conversation with yourself.

Let it be your first step on a real life journey of lifetime starring you.

You can get my Working From Roam Tools & Resource Guide here.

I wish you safe travels and a life stuffed with awesome experiences.

Dream Big!

Ray Wood

PS: I LOVE hearing stories from roamers and how they made it happen. Why not pay it forward and use this link to share your story so others might learn from your personal journey. (Thanks in advance for sharing)