50 Ways to Prepare for a Remote Year

ChecklistI’ve been working remotely for years, if you consider my home office remote.  Though I do get to travel quite a bit, the majority of time I spend working is isolated from the rest of the world. Next to family and friends, travel is THE most important to me.

So when I learned about Remote Year in mid-April, it piqued my interest immediately. Being the spontaneous person I am, I applied on a whim 2 days after finding out about it. A week later I was interviewed. Within a month I was signed up to start the yearlong adventure in less than 10 weeks. It would turn my world upside down. It meant packing up my life and moving out of my home of 23 years.

The first thing I needed was a list. Where does one start? How about by replacing all the floors in that house. Now this may not be everyone’s first thought but I do tend to be a tad over-ambitious. And what a great way to empty out your house… fast! Just book those busy contractors and watch your belongings fly out of the door!

Even if you decided to avoid the notion of a home renovation at a time like this, there are plenty of other lists to get done. Like a creeping rhizome, my initial list, grew sub-lists, secondary lists and associated lists. All things that needed to get done before I left for a year.

I summarized my last few weeks of madness into 50 Ways to Prepare for a Remote Year


If you are fortunate enough to leave someone behind in your house, then you don’t need to worry about this section. Though getting rid of stuff is a great way to start letting go of the weightiness of our physical existence. Besides, you’ll feel so much lighter when you get back.

1.     Research and book your storage. You will have stuff that needs to be put away for a year. Rule #1 – Once those closets are emptied out, you will definitely have WAY more stuff than you think.

2.     Start downsizing your stuff. Identify the stuff you really, really really want to or need to keep. Then separate it from the nice to haves or not to haves. There will be several stages of letting go – the stuff that you don’t want to get rid of will eventually go. But be gentle with yourself through the process. It takes time to process loss. Like a loss of a loved one, you need to grief the letting go of your stuff. Some stuff will definitely be easier than others stuff. Don’t underestimate the emotional power of our attachments.

3.     Have a yard sale. This may be a personal preference, however I recommend you do it because it will give you a perspective on the value of your stuff. Things that you think are valuable, will lay abandoned at the end of the day. A harsh perspective that you can’t get any other way. Yard sales are a reality check of current marketing conditions for your crap. Listen to what the market is trying to tell you.

4.     Donate books to your local library. – Unless you have a serious attachment to your books, let someone else enjoy them. Go through your library, book-by-book, and create ‘keep’, ‘maybe’ and ‘give away’ piles. Put all give away books in a box and drop them off at your local library… along with all the maybe books (honestly, if you have to think about it, you don’t need them.)

5.     Other ways to get rid of stuff –

  • Local charity – pick up/drop off.  Do this often to eliminate clutter. The more you pass along, the more clarity you will get – the end is in sight.
  • Create friend packages – careful select meaningful items that you want to leave for your friends, family or neighbours to remember you by when you are travelling.


If you’ve never done this, it can be a little intimidating. Just make sure you have all the appropriate documents ready when that perfect tenant comes along.

6.     Download a rental application with a space for references and lease agreement template.

7.     If you are renting your house, make sure to get the right rental insurance for your home early in the game. I left it to the last minute and I’m still working on the forms. Fingers-crossed I get the policy in place soon! Make sure your tenants have their own content insurance.

8.     Arrange for a property manager or someone that can inspect the home on a monthly basis and can make financial decisions in the case of emergency repairs. The insurance company needs this for the rental coverage.

9.     Prepare your house for rental – do whatever it takes to make your house look like something out of house and garden. The better it looks, the more you can get for rental. Research competitive homes in your area to determine what the market value of your rental property will be.

10. Powerwash the outdoor decks, repair any issues that will make the house look shabby. Shabby house attracts shabby tenants. Upgrades will provide great rental ROI.

11. Trim, weed and get your garden into the best shape possible. Curb appeal. Guaranteed your renters will not garden to your standards.

12. *Extreme measures only for the strong of heart*
Replace all hardware flooring – this may seem like an insane thing to do but this dramatic choice of preparation actually has quantum benefits.

  • Forces you to clean out your entire house prior to actually packing.
  • You have a great place to come back to.
  • You get a higher caliber of renters interested in your place.
  • You can charge more for the rental.

13. Have your heating vents cleaned.

14. Get your furnace maintenance done.

15. Have them check your air conditioning while they’re at it.

16. Do a preventive check plumbing and drains – clear any slsow drains or leaky faucet.

17. Check exterior for any potential problem areas that can be fixed before you go. Nobody wants to get a call about a leak or worse when you are on the other side of the world.

18. Create an appealing rental description of your house – review competitive ads in your area and borrow some of the wording to enhance your listing. Stage your property and individual rooms to great the most appealing photos for your ads.

19. Place ads – I used kijiji.com and viewit.ca. Then got results within 24 hours and rented the place out in a less than one week. Results may vary.

20. Consider short-term rental so you can move back in at the end of your trip. Renting furnished let’s you keep lots of your stuff in the house and saves on storage. Go with a reputable service that finds executives relocations, film people or insurance claims relocation. They pay the most. I’m told visiting professors at universities pay the least. Even less then the freshly divorced men with children and hefty support payments.

21. Make sure you get a credit check, letter of employment, call references and diligently investigate your potential tenant. This is not a popularity contest. They don’t have to like you but you have to trust them.

22. Provide written ‘instructions’ for the home. Let them know about the little idiosyncrasies of the house. If they are aware, they may take a little more care.


23. Wondering if you should sell your car? Do a keep search to see how much the market might pay for it. That will give you a dose of reality. Is it worth storing? Or could you use the money more? If you really like your car and it’s worth more to you than what you’ll get on the market, keep it.

24. Find parking for you car – City dwellers, I recommend that ask friends that live in apartment or condo buildings near you. There is surely an empty spot that someone would like to rent to you for the year for a reasonable price.

25. Have car detailed so you don’t store your dirt along with the car for a year. Hmmm… didn’t get a chance to check this one off my list.

26. Call your car insurance company way in advance to schedule the reduced coverage to fire and theft only. It takes these guys a bit of time to sort that out.


27. Find a person you trust to receive your forwarded mail.
Then do them a favour…

28. Call all mail marketers to be removed from promotional mailing lists. – For months in advance of your departure date, rather than recycling the unwanted addressed mail, call or email each of the senders with your request to end mailings.

29. Arrange for mail forwarding through the post office. In Canada, it’s cheaper to say you are moving permanently ($90 for one year of mail forwarding), than it is to do a temporary change of address ($250 for the same year.) So you changed your mind in a year and moved back in. At least you don’t have to pay for the mail forwarding when you return ‘cause you’ll be there.


30. Get your annual general physical done and get any prescriptions.

31. Book dentist and teeth cleaning appointment – get any dental or gum surgery done at home by a qualified professional if needed… you don’t know what you going to get abroad. It may safe your trip.

32. If you have local government healthcare coverage, then check out the rules around leaving for extended periods. In Ontario, OHIP will grant you up to a one year extended absence without having to reapply. Up to 5 separate years for business and 2 separate years for vacation. Just get your employer to write a letter saying you are required out of the country for new business development. If you are self employed that will be easy!

33. Travel insurance. Know this… not all travel insurance is created equal. Look for coverage that is not like your typical week vacation coverage. Where if something happens, the insurance company just wants to get you home so that your local insurance covers the rest of the treatment. ProtExpat insurance covers you for any and all medical conditions (pre-existing my require some underwriting) for the entire duration of your trip. So you can see a doctor on route and make claims without being forced to fly home prematurely .

34. Get a mani-pedi…. if you can squeeze it in.


35. Schedule all your changes for a few days before you actually leave the country so you can be assured that the changes are made before you leave. You know what telcom companies can be like. Rogers, I’m talking to you.

36. Mobile phone – if you are taking it with you, then get it unlocked so you can use local SIM cards along the way. (Rogers charges $50, it could go up from there.)

37. Schedule cancellation date for home phone. You don’t really need it any more anyway. I had my home number ported to my mobile. So when I come back there will only be one number. My one and only that I love so much.

38. Schedule cancellation date for cable TV.

39. Schedule cancellation date for internet.

40. Call the telcom company (Rogers or other disappointing service provider) back on or after the scheduled change date to get them to do it right this time. Uurgh!

41. Return all rental equipment for internet, cable and phone to telecom company.


This is not a packing list. There are plenty of places to find suggested things to bring on your trip and that will vary depending on destinations, climate and personal preference. These are some suggestions about the process of packing. I’ve also included random things that I wish I had. Though in the months to come I’m sure that will change too.

42. Do your final load of laundry the few days before you leave. That will give it time to dry and not wrinkle so much in the suitcase.

43. Only pack items that you regularly use at home. If you’ve never used those face cream sample that you found under the bathroom sink, you are not likely to use them while you are away. The same goes for clothes.

44. Start with your favourites for all seasons. Then plan for at least 3 rounds of editing.

  • Edit #1 – remove any unnecessary duplicates, separate out the seasons. If you can, ship some of your clothes ahead to accommodate weather and refreshing your wardrobe. Be prepared to ship some stuff home or donate it to charity in the countries where you are going.
  • Edit #2 – remove things you have not used in the past 3 months. Take pictures of things if you can replace items with photos.
  • Edit #3 – Pack your suitcase and weigh it to stay within flight weight restrictions. Some airlines allow for 23kg check bags but others are only 20kg. Remove more stuff.

45. Random things that I wish I had – tea towels.

46. Electronics – bring a power bar with a surge protector, then bring one plug adaptor. That way you can plug the bar into the wall using the foreign adapter and you still have several regular plugs available for charging multiple devices at the same time. The surge protection will save you from blowing up appliances like blenders, hair dryers and other motor-driven or heating devices. Brilliant.

47. Water bottle with loop for carabiner.


48. Check that your passport has not expired. Sure you’re a seasoned traveler and have travelled all over the world and more. Even more reason to check your expiry date. Travel confidence and sometime edge on arrogance. And that can kick you in the butt when you least expect it. It happened to me a few years ago.

49. Give yourself plenty of time to get to the airport. The stress of preparing will be compounded by the stress of travel. Cut yourself some slack and don’t mess with  the departure time. Plenty of time at the airport will give you time to wind down before boarding the plane.

50. Treat yourself to a Priority Pass airport lounge for a couple of hours preflight. You deserve it!

It’s hard to believe that all I’ve done in the past 2 months can fit into a list of 50 things. Within each one of these 50 things, there were another 5 to 10 tasks. So in fact, this could have been 500 Ways to Prepare for a Year of Remote Work. But then nobody would have read this. Or never mind, actually do it!

So congrats for making it through. I hope it inspires you to pursue your year of travel.

Finally, it’s all done. As I sit on the plane heading to my first destination, Lisbon, I can feel the stress starting to melt away. With a stopover in London, the lists quickly fade into a distant memory. All there is to do now is arrive and embark on this wonderful journey of a lifetime.