How We Do it (And Why You Shouldn’t Listen to Us)

Words by Dalene Heck / Photography by Pete Heck
If our inbox is any indication, y’all are ready to get serious about travel.Lately it absolutely overfloweth with logistical questions about our lifestyle and how to travel long term. We are so frequently asked about how we make money, what travel insurance to buy, what we pack, how we budget, how we blog, etc. – that we finally decided to put our answers all in one place.

We love hearing from our readers and try to be as helpful as possible, but we must preface this blog post the same way we do many of our responses: you’ve come to the wrong place.

Because in all honesty, even though we’ve been traveling for many years, we’re either just figured it out ourselves (the parts about making money), or we’ve just given up all hope of ever being good at it (budgeting and packing). There is a reason why we just tell stories and share pretty pictures and video on this site – we are not the most practical travelers. We have so few solid tips to give, in fact, that we’ll give you our brief suggestions but then refer you to other bloggers who actually know what they are talking about.

So, here we go.

Paradise.

how we make money

This is, without a doubt, the number one question we get. People love the idea of housesitting their way around the world, but recognize that these gigs are typically unpaid, and that revenue or a stash of cash is still required to put food on the table.

Rich Rich Rich

We are millionaires! (In Colombian Pesos, that is.)

We have both. We still have savings that we can dip into if we need to, but into our fifth year, we haven’t taken a dime.

Where is the money coming from? While the blog itself does make a wee bit of advertising money (and opens the door to some amazing travel adventures), it has mostly served as the platform for securing other opportunities, and in the last year we’ve developed many different sources of income: eBook sales, affiliate earnings, social media consulting and campaign management, freelance writing, freelance video, new blogger training, and more. We’ve tried a lot of different things to find out what we like to do and what works until we finally found our way forward. By putting our business skills and to work with our new found love of travel, we’ve found that sweet spot that can keep us traveling for years. For almost two years now we have been helping connect brands and bloggers and managing social media marketing campaigns. Recently, we’ve also published a book for the industry on how to work with travel bloggers.

Presenting in Finland

This has all been a long time in the works, and for anyone who thinks that they can start a blog and simply travel the world for free is sadly mistaken. It is not as simple as posting a few words and photos –  most of us nomadic-types work very hard at a number of different things in order to make this lifestyle sustainable – and truth be told, most of the best opportunities for income do not come from blogging alone.  We spend far more time stuck behind a laptop than we do exploring these days – the big differences compared to our previous lives being that we are working for ourselves and can do it from anywhere in the world. We like that.

Although a few people have bravely left home with few dollars and managed, we are not those people. If it wasn’t for our savings we wouldn’t have gotten this far, and if it wasn’t for our hard work to develop various revenue streams, we wouldn’t go much farther. There is no magic formula for how to make this lifestyle sustainable – the opportunities will vary as much as individual skill sets do – the key is to find something you like to do and work hard to turn it into a viable location-independent business.

how we budget

The short answer is that we don’t, out of pure laziness. We are frugal, without question (and housesitting helps us a lot with that), but we don’t keep ourselves to a strict budget nor do we track our expenses.

  • Should we? Probably. And if we did, we would use this: the “Trail Wallet” by our friends at Never Ending Voyage. Track by month, track by trip, convert currencies right there – everything you could want in an expense tracking application is there. (Or, so the many, many satisfied users say. We should probably become one of those.)
  • Wondering about what you should budget based on where you are going? Among other great tips, Legal Nomads’ World Travel Resources page rounds-up plenty of general and location-based budgeting posts from other bloggers.

Dalene-Housesitting-974x649

how we pack

Ha ha!

Ha.

Oh boy, if you could see the state of our bags, you would not ask us this question. How we manage to stuff the crap we do into the two bags we each have is beyond me. Within minutes of setting them down in a new location, they naturally explode into a giant unorganized mess.

Without embarrassing ourselves by disclosing the exact contents that we haul around the world with us (and because we are kinda scared to reach into the deep corners of our bags), we have each decided to just give one packing strategy that we actually think is quite good. Because, in reality, we each have only one good strategy.

Dalene – The essential cotton dress(es). Many nomads are sun chasers – hopping around to new destinations when they serve up their warm weather. We are not those nomads, in 2013 (for example), we bounced around relentlessly – from a Wisconsin winter to tropical Guatemala then Finland in February, and from a scorching summer in Poland to near the Arctic Circle. The only way I can make this work and keep my wardrobe to a reasonable size is with short sleeved cotton dresses – in cold weather I can layer them with leggings and a long sleeve shirt, and in warmth wear them freely. I see no other logical way.

Pete – Compressible air tight packing bags help me get the most room out of my backpack. They are great if I need to only pack a carry-on for a day trip and give me lots of space opposed to the clothes just being packed on their own. Plus they’re waterproof so when my bag sat in the rain in the London airport my clothes stayed dry.

There are so many other fantastic resources out there to advise on packing for long-term travelers, here are just a few:

  • HerPackingList.com has oodles of posts reviewing different products, packing strategies, etc. (HisPackingList.com exists too, but is not as thorough yet.)
  • Nora has been at this nomadic gig for a long time, and so her packing list is one of perfection!
  • I love these tips from our friend Gigi on how to stay fashionable while living out of a bag.
  • Erin and Simon from Never Ending Voyage are a wealth of information on their lives as nomads, and their packing list is no exception.
  • Janice, aka Solo Traveler, has some great basic advice on packing with the bare minimum in mind.

Dalene Working

how we blog

We have been getting more frequent requests for blog “coaching” from newbies who are about to set out on their world journey and others who are just bursting with stories to tell.

I can tell you definitively that our blogging journey has been one of intense trial-and-error, and yes, we have many tips to give. But rather than reinvent the wheel and develop our own resources on it to share, we are instead going to point you to the very valuable Travel Blog Success platform. Not only will you begin with a well-crafted course that starts from the ground up, but you will have access to a variety of forums (their private Facebook page alone is worth the investment as it contains many of the top bloggers in the world offering their advice), webinars, and more.

what we do for travel insurance

Being from Canada has huge perks, one of them being the health insurance. Even better is that we are from Alberta, where premiums are absolutely zero, and their policy allows us freedom to travel. As long as we check in at home every couple of years (which we do), we can have that policy run in the background with some extra travel insurance on top.

We use Travel Cuts “Bon Voyage” travel insurance. Because they only insure travelers under 50 years of age, the premiums are kept very low (we’ve never found better rates). Plus, we can buy policies that last up to eighteen months which is perfect given that we are often out of Canada for longer than one year at a time.

Mobile Office

other helpful stuff that you should read

If you are serious about wanting to make a life of travel, there are several other resources well worth your time:

  • The eBook “How to Live a Life of Travel” by Wandering Earl is the best all-encompassing resource out there. Read our review of it here.
  • Jodi from Legal Nomads has many resource pages on her site for living a life of travel, but this one in particular is useful for those who want to make their living from the road.
  • Don’t just take it from us (really), in this very informative post, fifteen travel bloggers reveal how they have made their vagabonding ways work for them.
  • The Professional Hobo offers oodles of resources on how to travel in a financially sustainable way.Start here, and be sure to sign up for her newsletter for ongoing tips.
  • Also check out this complete guide on “How To Travel The World On Any Budget“. It dismantles the money myth and gives you the tools you need to make world travel a reality – on your budget.

Anything we’re missing? (I’m sure there is, like I said, we ain’t good at this.) Please leave us your questions and/or other resource links below so we continue to update this post and make it more helpful for readers (and, errrr, us.)

Please note that some links in this post are affiliate links. While it comes at no increased cost to you, we are rewarded with a small commission on your purchase. We firmly stand by every product that we promote.

65 Comments... Read them below or add one of your own
  • October 14 2013

    Thanks for the great tips!
    I’m also an Alberta resident, and I was under the impression that you could only leave the province for periods of no more than 6 months at a time and maintain healthcare. I’d welcome additional info!
    Many thanks
    Johanna
    @TravelEater recently posted..Spring City — Vancouver

    • October 14 2013

      Hi Joanna! Here is a link to the coverage for Alberta residents (http://www.health.alberta.ca/AHCIP/outside-coverage.html). It does specify 6 months, as you said, but there are options for extended coverage (a little further in that link), where it says up to 2 years. We have had no issues in getting that each time.

      • October 14 2013

        Thanks Dalene – good to know it was an easy request. I’ll keep that in mind for future, thanks!
        Happy travels and maybe we’ll meet up one day, either on the road or “at home” 🙂
        Johanna

  • October 14 2013

    Thanks for such a great and informative post 🙂 It will definitely help me in my trip preparation!

    • Pete
      October 17 2013

      Great Catherine and good luck! Let us know if you have any questions 🙂

  • Thanks for the awesome shout-outs! You rock. And this is a GREAT resource post.
    If I might make a wee shameless plug on the packing list front, I have the ultimate packing list for full-time travel here….in the form of a fancy widget that explains why each item is in my bag….
    http://www.theprofessionalhobo.com/2013/07/the-ultimate-packing-list-for-full-time-travel/

    • Pete
      October 17 2013

      Thanks Nora! We’ll move this up into the post.

  • October 14 2013

    Thanks for a great post! It’s refreshing to hear from someone they don’t have the answers (and yet still be pointed in the right direction to find a good resource — and listen to your advice when you DO have the answers!). I appreciate your candid advice as you actually have some great tips, even if we “shouldn’t listen to you”.
    Becky recently posted..Next Stop: El Salvador or Nicaragua?

    • Pete
      October 17 2013

      Thanks Becky! We’ll always be the first to say “you shouldn’t ask us” because we seem to do things backwards. But we do have a few tricks up our sleeve 🙂

  • October 14 2013

    Ditto Nora’s comment: thanks for the shout-out! 🙂

    • Pete
      October 17 2013

      Of course Gigi!

  • October 14 2013

    Haha, you guys sound like me! I do everything “wrong” according to most people – I don’t travel long enough, I pack too much, I move too fast, I don’t keep track of my budget, I plan ahead, I don’t plan enough… You name it, and I am probably guilty of it.

    But you know what? I don’t care. These are my travels and my blog, and I’ll do what I want!
    Amanda recently posted..Venice Isn’t the Only Island in the Venetian Lagoon

    • Pete
      October 17 2013

      Yeah, damn straight Amanda!

  • October 15 2013

    Haha… glad I’m not the only one out there who thinks “uh oh” when someone emails me to ask how I do it! Also good info on Travel Cuts, I never thought of that.. I’m from SK and that happens to be the only province (well, that and Quebec) that World Nomads doesn’t cover, which seemed to be the only place I could get more than 6 months of world traveler insurance from. I will definitely check out Travel Cuts when I’m up for renewal…right now I’m paying some seriously high prices for international expat insurance from some company in the States.
    Rika | Cubicle Throwdown recently posted..Roatan Month 14 Roundup

    • Pete
      October 17 2013

      Wow, what did Saskatchewan do to World Nomads? It’s pretty crazy that we need an insurance policy on top of our insurance policy to go to the U.S., but if there is one place you need it, it’s there.

      • Martha Anastasiou
        May 26 2016

        That’s for sure Pete! I’m from the states and medical insurance as well as medical cost are out the wazoo here! Not to get political but people in the states that have never visited another country have no idea. I was fortunate to be able to live in the south of France for ten amazing years and the medical care as well as cost there is one of the reasons I was reluctant to leave and am now planning to return.

  • October 15 2013

    Just an FYI for Ontario residents…

    Ontario also has a two year leave of absence! Super easy to get! Just cruise into the local health department office and fill out some paper work.

    We were recently home and were even able to have a check up at our family doctor with NO problems whatsoever.

    Happy Travels!

    • Pete
      October 17 2013

      Thanks for the Ontario tip K.T.!

    • Ingrid
      March 29 2015

      Can you tell me if Ontario has an age restriction for this 2 year leave? I’m 63 and love travelling and dreading the 2 year mark when I turn 65 and OHIP seems to think I can only be trusted for 1 week away. Thanks and love the blog.

      • March 30 2015

        Hi Ingrid, we personally have no experience with that, but check this web page for more info. http://www.health.gov.on.ca/en/public/publications/ohip/travel.aspx

        • Ingrid
          March 30 2015

          Aah yes, dementia must be setting in — I meant my Visa travel insurance is only good for four days at 65. I will need to explore independent insurance options for anything longer. Thanks for the link. Very helpful.

  • October 15 2013

    I love that you aren’t claiming to be experts in ALL areas. That said you guys pretty much rock! I think we are a little more similar to you, in that we are still trying to figure it out too. Savings has been our funding and we will slowly unfold the rest. We have our first house sit in a couple of weeks, so baby steps.

    I think the biggest learning we have had the past year is do what works for you. You see so much that others are doing, but is that what you want. Sometimes you need to cut out your own path. 🙂 Thanks for this.

    • Pete
      October 17 2013

      Precisely Heidi, you need to find out what works best for you. We hope this post will help give people ideas to find their own path 🙂 Thanks again!

  • October 15 2013

    Helpful one! Since I have been blogging for the past 14 months, I understand that blogging is tremendous labor and no money initially. But it’s absolutely fine, because I am doing what I like!

    • Pete
      October 17 2013

      Good for you Renuka, you have to like it otherwise what’s the point, right? All the best going forward!

  • October 15 2013

    Interesting timing as I just attended TBEX and am trying to figure out next steps, monetization, and generally where to go from here, after 15 months “on the road”. My husband and I are supposed to be having a With Husband In Tow corporate retreat to work together on these things, but the darn blog and travel planning (and the dogs we are sitting, and the food in Singapore) keep getting in the way…But, thanks for all of the tips.
    Amber recently posted..Pico Iyer and Where is Home?

    • Pete
      October 17 2013

      No problem Amber and let us know if you have any questions along the way. We can try and help 🙂

      Best of luck forward!

  • October 15 2013

    Awesome article! There are so many factors to this life on the road. Thanks for your honesty, and I for one, was one of those Bloghouse attendees and really feel that it helped me get focused and know that I was on the right track, my blog just needed some tweeks here and there. Thanks so much to Pete for all his help with my website. You two are certainly pleasant to be around! cheers!
    Cacinda Maloney recently posted..La Bottega del Ligno: The Wood Shop in the Forli Region of Italy

    • Pete
      October 17 2013

      Thanks Cacinda, it was our pleasure to help out. Keep working hard it and best of luck. If you need anything, you know where to find us 🙂

  • October 15 2013

    Thanks so much for the Trail Wallet mention guys.

    You know, we’re all just figuring things out as we go along. Even though we travel with just carry-on backpacks I still feel I have too much stuff. And the income thing is a constant struggle really, it gradually gets better but I’m not sure it’s ever easy.

    • Pete
      October 17 2013

      You’re welcome Erin. We are still figuring this whole game out too and probably will be for a long time as things always seem to be changing. As far as stuff goes I wish we could go down to carry-on only, but my camera gear alone takes up almost 40L. When the fees go over $100 per check-in bag, that’s when I will reevaluate.

  • October 15 2013

    I love all of your honesty! lol

    • Pete
      October 17 2013

      Thanks Jeska, nothing but truth bombs here.

  • October 16 2013

    I am terrible at packing too. I have 65l backpack and daypack and still don’t have enough room. I have the additional challenge of having to take smart work clothes with me for my NGO contracts, so I need to try and take stuff with me that looks smart enough to wear in an office, but is not too posh and unpractical for sightseeing trips. Oh and I also like trekking, so I also need room for some trekking gear, such as boots, warm clothes etc. That takes up the most room. Sigh!
    TammyOnTheMove recently posted..Me vs. the leeches – Mountain biking in the Chi Phat jungle

    • Pete
      October 17 2013

      I hear you Tammy. From our camera gear to all the seasonal clothes we’re hauling around it gets a little tiresome. Oh well, it’s the life we love 🙂

  • Sam
    October 17 2013

    Thanks for such an honest response to these ever popular questions, and giving resources of other bloggers who you believe have better answers where you’re lacking. It’s so great to know that everyone has their own approach to these things, and I think that’s a really powerful motivator; there is no right or wrong way, just your way!
    Sam recently posted..Top 10 Art Galleries and Museums in Lima

  • Pete
    October 17 2013

    Exactly Sam, hopefully we can direct people to some ideas to make their own choices! And we may have a few answers to share as well 🙂 Thanks again!

  • Sab
    October 20 2013

    Thanks for this great post, and thanks for including me 🙂 Very informative and full of useful resources, will totally share this!!!

    Making money with a travel blog is hard, it’s not only writing a few blog posts and the money rolls in. I spend a lot of time to promote my blog (really like crazy!!) and on the other side I learned to live with very little. I need less than 500 bucks a month to be happy and buy everything I need.

    I never worked harder in my life for such a small amount of money. The money doesn’t even matter. I love my work, I love every day seeing my blog growing and encouraging people to live the same lifestyle. Best decision ever.
    Sab recently posted..PARAGLIDING IN ÖLÜDENIZ: A SPECTACULAR PLACE FROM EVERY PERSPECTIVE

  • October 20 2013

    Great post! So thorough and so very much appreciated! These topics, as you yourself point out, are often a great mystery to those who haven’t ventured into a professional nomadic lifestyle and you have detailed it all beautifully!
    Mary @ Green Global Travel recently posted..PHOTO GALLERY: Serengeti National Park Wildlife Safari

  • October 21 2013

    Great post! Thanks for being so honest and so transparent (and linking to so many other good resources).
    Kirsten recently posted..Rally School with Brite Spokes

  • Kim
    October 27 2013

    You guys did a great job talking about the biggest concerns of long-term travel in my head: money, health insurance and packing.

    I know everyone’s experiences will be different but I like that you laid it out as you’ve done it and have also shared other resources of how others did it, as well.

    The biggest takeaways for me is that it’s all a journey and that it’s okay to learn as you go.
    Kim recently posted..Tiny House Living :: From 2700 ft² to 120 :: Interview with Laura LaVoie

  • November 10 2013

    Very inspiring! This is my first visit to your blog, what a nice place you have here!

    As someone who is learning to blog and loves travel, I was definitely motivated by this post. I will be looking forward to reading more posts & I wish you all the best in your travels and business ventures!

    -Mr. Andrews

  • July 19 2014

    Hi Dalene, Thanks for sharing your experiences with us. Great post, love your honest words. All the best, Carina

  • Adam Paul
    November 27 2014

    Good experience is easy to share bcs its more than being in school.!

  • Great tips and links here. Thanks!
    Cristina ✈ (@travelingjourno) recently posted..How to Learn French (or Any Language) in Less than 3 Months

  • December 18 2014

    Love the tone of your articles and site. You provide great information all while helping people understand that while you do it, it’s your own way and may not be the best. We feel ya there. We try to provide the best info we can so people know they can do it if they change their way of thinking and are willing to change some priorities.
    Jeep Gypsies recently posted..Camp Memberships – Which Ones Do We Have

  • February 26 2015

    Great info, thank you. Really helpful!
    Sally recently posted..Five random things I will miss about the Philippines

  • March 23 2015

    Hi guys,
    Two questions:
    1. In your travels, have you come across a Canadian woman traveler who might marry an expat American, so I can get that Alberta travel insurance?

    2. What are those two (pink+white) devices hooked to your laptop?

    LOVE your blog, love your writing, love those photos!!

    • March 26 2015

      1. Haha! Haven’t come across anyone yet, but I will keep you in mind. 🙂
      2. The white device is a mifi, and the pink was the case for my iPod (it got dyed a bit from being in my red bag).

  • March 30 2015

    Thank you for the tips! I have been trying to prepare life as a digital nomad. These information helps me! 🙂
    Marina Utami recently posted..Preparing First Time Solo Travel

  • Cheryle
    April 27 2015

    A big shout out hello from Calgary!
    So what finally gave you the courage to just do it! To end the research and just go?
    I’ve traveled all over the world, but always had a nice safe job and house to come home to.
    Give me the courage! 🙂

  • cheryle
    April 27 2015

    What work is considered legal when you are on a tourist visa?

    • April 28 2015

      I don’t know the answer to your question. We are freelance, so working independently no matter what country we are in.

  • Kristy
    June 14 2015

    Just discovered your blog – AMAZING!! Any suggestions for resources for traveling with kids? We have 3 and have been trying to figure out how to even work out a plan for 1 year of travel with them in tow. I find it a bit easier looking for suggestions for 1 or 2 adults traveling, but throw kids into the mix and there’s almost nothing.

    • June 17 2015

      Hey Kristy! There are a lot of great blogs out there for traveling as a family, but the first one I would suggest is definitely ytravelblog.com. They are full of info!

  • JOELLE PA
    August 13 2015

    WOOOOW!! God bless you guys for putting all this info together and for others that shared, too!!!

    I really think there is better way for our bags/luggage to help us organize all our crap as there is a big trend of people traveling much more then ever before. And it’s interesting that people in this trend are becoming a kind of unique labor force, too. I think it’s totally possible we have a conference called World Travelers…whether they travel around locally a lot or hop skip around and in between countries, to share info and support their businesses or etc…? idk…

    Anyways, I just think it’d be cool if some of us be able to meet up somewhere in this world while traveling/wwoofing/housesitting/etc ; )

    Cheers! And thanks so much guys!!!!!

  • October 20 2015

    Wow this is the best list ever! Thank you!!!

  • Tristan
    November 17 2015

    Bonjour Dalene et Pete!

    Je suis français et j’ai 18 ans. j’ai décidé de vivre une vie sans regrets! alors j’ai tout plaqué 🙂 Je voulais savoir, comment vous faites pour les hébergements, le travail, etc…Merci de votre réponse!

  • millie
    January 20 2016

    I really like the idea about layering the dresses. This year I have a couple of long trips that span the seasons and was wondering what to do. Thanks for the tip. I’d like to see some photos of the combos!

  • March 5 2016

    Thank you Pete and Dalene for another wonderful post. My dream is for our little family to take off by the time we’re 40 – my 39th birthday is next week so we need to get cracking. I stated my natural parenting site to try to give us freedom in the future – it’s a baby at the moment but hopefully some day soon it may mean quitting the day job and taking off. We absolutely love travel and have done a lot of it – Canada is out fourth country we’ve lived in the last decade, and we just became citizens 🙂 Having our son has amplified how fast life passes us by and we feel it would be the greatest gift to show him the wonder and beauty of this amazing world we live in. And then maybe my blog will take on even more travel! Happy wandering 🙂
    Tracy recently posted..Extraordinary Things Happen When We Simplify Childhood

  • May 8 2016

    Just came across this post. Wow, lots of great gems inside. Thanks for the sharing. Definitely useful for many travelers.

  • Amanda
    November 5 2016

    Hi. Great advice! Thanks. Just one thing I am curious about is what address do you give your bank etc? Although I am paperless for bills etc, our banks still want a physical address.
    Any tips would be gratefully appreciated.

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