Preparing to Take a Career Break: Round the World Planning Timeline

Ok admit it, everyone considered dropping everything and hopping on a plane to travel around the world.  Even if you said you hadn’t, no one would believe you.  But that is the easy part.  I mean, it really wouldn’t be very tough if you didn’t own anything, didn’t have a home, car, bills, pets, and retirement goals.  Oh yea, or a job.  As long as you have none of that stuff, dropping your life to trek around the globe would be a walk in the park.  That is until you had to plan the trip, figure out vaccinations and visa requirements, learn how to pack for a year in a carry on sized backpack…  Alright, point taken.  This isn’t a “plan it over a few beers one weekend” kind of trip.  This takes lots of prep work and a timeline to make sure you don’t miss any of the dozens of things that you need to remember.  We weren’t able to find many resources or travel blogs with a decent lists of things to remember and timelines, so we have built one based on our experience.

In this post, we are going to make our own timeline with our list of essential details for you to use.  I know, there is no way that everyone’s list will be identical.  If you need to find a sitter for your garden gnome collection, that won’t be on this list.  Gotta get a replacement for your moonlight job as a speed chess announcer?  You’re gonna need to remember that one on your own.  I’m talking about the things that will be on most people’s list but a fairly (very) detailed rundown, starting with the furthest out.  Also, this post got pretty lengthy so we have also added it in list format at the bottom.

BIG Picture

T-1 or more years 

New Zealand Doubtful Sound Round the World Travel
That early time when everything looks so smooth

This is the time to really buckle down on budgeting.  This is two fold.  First, you need to figure out what you need to have available for the trip of a lifetime.  Are you planning on sleeping in the kitchen of the cheapest bed bug hostel in Kuala Lumpur?  Well that website which said you can travel the world for $5 a day might be right up your alley.  For the rest of us who aren’t looking to compromise safety and only compromise comfort to a degree, be serious about what you may need, and give a cushion.  You really don’t want to have to fly home halfway through the trip because you forgot to factor in the cost of food or flights.  Second, you need to think hard about what is really important to have in your current life.  Now I’m not talking about switching your dog to a grass fed diet to save a few bucks, despite what your free spirited neighbor said.  I am, however, saying that you need to decide if that deluxe cable package and high maintenance imported sports car are really necessities.  We went through all of our stuff and sold what wasn’t really important, and stopped going out to eat altogether.  I’m not lying, I’ve eaten more peanut butter sandwiches this year than all of your children put together.

Go through all of your junk and see what you can downsize.  You’ll be surprised at how much you can get rid of and not even notice.  This will take a while so start early.  You’ll be able to sell some stuff for money on Craigslist, and can drop the rest off at Goodwill or some other non-profit.  Your favorite collection of porcelain clowns?  Gone.  Grandma’s hand knit neck warmer, which you said you would cherish forever?  It’s time to let go.  Just think about the joy that will bring someone when it is purchased for next years dirty Santa exchange.  We watched the Minimalism documentary on Netflix for additional inspiration, which really helped us part with anything that wasn’t necessary or useful.  Getting rid of your excess baggage will free you up and save money on a storage unit and movers.

Go through your filing cabinet and see if you still need all that paperwork you’ve been saving.  We were able to rid ourselves of stacks of old paperwork that was no longer relevant.  This can also include clean out of emails and electronic picture albums.

What are you going to do in the long run with your job? Check out the possibility of taking an extended leave if that option is available.  This isn’t common in the US, but it is possible sometimes and with some companies.  Neither of our jobs had that option, but we did our best to leave the door open for rehire upon our return.

New Zealand avalanche backpacking round the world
Make sure to check the weather!

Start determining when you want to leave for your career break and where you want to go around the world in the time you will have.  This is tougher than it sounds since there are literally either 194 or 195 countries in the world, depending on how you count.  We spent a lot more time on this part than we ever would have thought.  We had to narrow down our master list to something that would be feasible without us being in a huge rush for a year straight.  More importantly, every country has high times to go (which will be expensive) and low seasons (cheaper) for travel.  These can be due to holiday times, but also things like typhoon seasons and dangerous heat.  This can get tricky when you need to link countries back to back without doing a ton of backtracking.  We must have rebuilt our final list at least five times based on seasonality or just difficulty with flight options.

Get your estate in order.  Make sure you have all of your documents in place such as wills, trusts, powers of attorney, etc.  Get an appointment set up with your estate attorney to update all of these items if you already have them in place.  Ensure that you have an appropriate PoA in place which doesn’t require incapacitation for the duration of your trip.

Talk to your financial advisor.  This is essential as they will likely have specific insights in to your particular situation which you should consider.   They can also help project the impact of different career break lengths and levels of spending over the long-term.  Make sure to consider if you need to front weight your retirement contributions to get them in before you leave.  Plus, if you plan on using your lower income bracket while on your break to do 401k rollovers and Roth conversions, make sure that you have your paperwork from these institutions in hand and notarized so they can be submitted soon after your last paycheck.

Look at your corporate benefits to see if your retirement plan has a vesting schedule, and make sure you don’t leave money on the table by a mistimed exit.

Things Are Getting Real

T-6 months or so

Get a passport!  Or if yours is getting older, get it renewed.  This can take several months so make sure this is done pronto.  Order the passport with extra pages (52) for no additional cost.  Some African and Asian countries require several blank pages for entry requirements.  Also ensure your emergency contact information is filled out.  I had about two years left on mine and went ahead and renewed it early just in case.  Most countries require that you have at least 6 months left on your passport in order to enter the country, so your passport really expires 6 months earlier than you thought.  You really don’t want to get turned away at the Bangkok airport after spending all day on a plane and a year planning your trip.  Also, this would be a good time to get extra passport photos.  We found that many countries require that you submit 2 loose photos with your visa application, so we got around 20 each to bring along just in case.  You can get these made and shipped online for dirt cheap (MyPassortPhotos or ePassportPhoto).  This will save a bundle over showing up at the drug store and mortgaging your house to afford a couple of pictures.

Start working on your vaccinations.  Use an accurate itinerary to cross reference what vaccines you may need on the CDC website.  Have a good idea about which vaccines you might need so you can have this discussion with the medical provider.  Set up an appointment at the local travel clinic, health department, or military hospital, and bring your vaccination records.  Some vaccines need a series of shots a month apart so you’ll need to plan accordingly.  Prices of vaccines can vary greatly so shop around and  research online.  Also, make sure you look into whether you will be in malaria zones during your trip!  We have found that most travel blogs didn’t mention this so it could easily slip your mind.  There isn’t a vaccine for malaria, so you will need to get a prescription to take with you.  We looked on the CDC website and it looks like almost everywhere you go has a malaria risk, but we found more helpful sub-region specific maps on FitForTravel.  Make sure to ask the travel clinic about other prescription travel medications you may need.

Keep working to fine tune your round the world itinerary.  Start checking flight costs and availability, and cross-reference the seasons and weather patterns.  We made a map of our high level route but left the details for land crossings loose until we were closer to our arrival dates.

Build your packing list with the level of stuff you want/need to bring with you.  Make sure you consider that you will be lugging this stuff everywhere for a long time.  Favor light weight items with multiple purposes, quick dry, etc.  Foreign airlines often charge extra for larger or heavier bags.  Don’t forget your medicines, birth control, prescriptions, vision correction, and your yellow vaccination card…  We will do a subsequent post on our packing lists.  Consider sending clothing items and sleeping bag liners to InsectShield to get sprayed with insect repellent.  This helps with mosquitos for tropical or malaria zones, along with other pests.

This is a good time to start telling your close friends and family about your plan to take a break from your career to adventure around the world!  This is when it gets real because you are verbally committing yourself to the trip.  This is when it changes from a really cool discussion to a goal you are working towards.  It is also motivating when the people you know confess that they regret not having done something like this themselves and support your decision.  Be careful about making it too public though depending on how this could affect your current job.  You don’t want them to hear your news from anyone other than you.

Camping backpacking s'mores
The differing expressions of those with and without s’mores

Figure out what to do with your pets, if you have them.  This can be really easy or very difficult depending on the pet.  That mute lab which brings you beers on command may have a waiting list of foster parents, but your Amazonian python which requires hand feeding may take a little searching.  Don’t forget that pets can also add expenses outside of your travel costs, both from sitting and for stocking their supplies for the trip length.  We found that it is very convenient to auto ship directly to your pets foster parent through various sites.

It is almost time to make a decision on your residence.  If you have a house and are going to sell, you should start getting it ready for the market and determining when to list.  If you are renting, find out how much notice you need to give to vacate and try to match the start of your career break with the end of your lease term.  If you are going to rent your home out, figure out these arrangements.  You could also find a friend to house sit as an alternative.  Your python will be a good roommate.  We decided that selling our house made the most sense and kept us from having to worry about something else back at home.  This also allows more career location flexibility upon return.

Do research on accounts which are good for travelers.  This includes credit card(s) and bank accounts with debit card(s).  You want to get these set up to allow easy access to your finances without charging ATM withdrawal and foreign exchange fees abroad.  Also, be on the lookout for accounts which have secure access beyond the normal name and password.  We found several recommendations for accounts and debit cards with Charles Schwab which have these features.  Their accounts can also be set up to have security token access for added safety.  Some credit cards also have trip protections/travel services.

Get your last-minute dentist and doctor appointments scheduled.  We set a dentist appointment for the month before we left but had health exams beforehand to ensure a cushion if we uncovered anything unexpected.  Make sure to get prescriptions that will last your entire trip.

T-3 months or so

Start researching travel insurance.  This is essential as it will be the only thing that can help you get back home or taken care of in the event of an emergency.  Keep in mind that you will likely be losing your health coverage through work, but most US policies won’t cover you overseas anyways.  We strongly recommend reading the fine print on each policy you find as there are some significant differences which aren’t apparent on the main bullet points.  This was a time-consuming and frustrating process, but we believe that we ended up making a wiser choice than what was recommended by many travel blogs.  Watch for hidden limits and exclusions for natural disaster and political evacuations.  We ended up choosing Seven Corners after narrowing it down between that, World Nomads, and IMG.  And don’t forget, you will need to have coverage when you return, so keep an eye out for one that allows a month or two overlap when you get home or get a subsequent policy beforehand.  You can also see our full comparison of these insurances including an explanation of the fine print.

Decide what big-ticket items you will be bringing, if any, and get these set up.  I’m talking about a laptop to use for research and storage, cameras, etc.  This will give you time to shop around for a deal or wait for a sale.  You can see what’s in our camera bag.

Backpacking Patagonia Round the World Travel
Definitely match your backpack to your jacket

Decide on your travel packs.  You can find countless resources online to help with this, but it comes down to what feels best and balances features and size.  If you can’t give up that paperback book collection for your trip, you might need to look into a larger pack.  Keep in mind that having to check baggage puts you at significant risk if it is lost since you will have your whole life in that bag.  We purchased, tried, and returned numerous backpacks before we found what we wanted.  Everything was too uncomfortable, too big or small, or just didn’t pack right.  We ended up with Osprey Kestrel 38 (male) and Osprey Kyte 46 (female) backpacks.  Light, easy access, and can fit a surprising amount of stuff.  The standard for carry-on acceptance is 46 liters but this can vary by carrier, bag dimensions and weight.  We have found that packing cubes are an easy way to organize and compartmentalize your bag if using a backpack.

Start doing serious research on visa requirements on sites such as the US State Department.   These can vary widely from country to country with some allowing tourist visas upon entry to others requiring applications beforehand.  In general, many countries also require that the visa be used within 3 months from approval so you are limited to how far in advance these can be done.  This can be more difficult for long term travelers since they will need to be issued throughout your trip and cannot be done in bulk beforehand.  You may have to obtain your visas in person at an embassy or consulate along the way (e.g. China, Russia).

This is also a good time to decide what you will be doing about your vehicles.  Leased cars could be returned depending on the contract.  Some leases can be extended beyond the original expiration on a month to month basis.  We decided to keep only one of our two cars so we had one upon return.  Make sure you know how long you will need to dispose of and market accordingly.

If you have any rental homes, ensure that they will be under proper management.  Make sure you discuss extending lease terms with renters and make needed repairs before your travels.

Make sure that all items necessary under the estate process are completed and notarized, such as powers of attorney.

Make sure that your resumé is up to date for use when you return, if necessary.  Be sure to think about how you will explain this gap in your employment.

Ensure that all investment accounts are properly set up and structured.

Apply for an international drivers permit.  We went through AAA.

This is about the time when we alerted our jobs of our plans to take a break from our careers to travel around the world.  It is a good idea to not wait until the last minute or required notification period to stay in good standing with your company.  Make sure to tell your manager in person.  We were honest and upfront regarding the reason for our choice.  No legitimate company can fault you for taking a break from your career for once in a lifetime experiences and adventures.  Both of our companies were very supportive of our travel plans.Plane New Zealand Round the World Travel

Buy your first plane tickets and book your first accommodations.  This could also be in other time frames depending on your situation.  We decided to wait to book anything until we had the due diligence results and negotiations done on our house sale so there were no surprises.  We also don’t plan to book anything more than a few months ahead throughout the trip to allow us flexibility.

Look into SIM card options for your unlocked cell phone in countries on your itinerary.

Where the Heck Did the Time Go?!

T-1 month from liftoff

Don’t forget to call all of your financial institutions and alert them to your plans.  They are likely to block foreign transactions as fraud if not.

Download all the books you will need over the first few months or entire trip.  They don’t weigh anything and this keeps you from having to set up your e-reader to potentially spotty wifi on the road.

Book your travel insurance.  Make sure they overlap your domestic health insurance dates.  We set all available vacation at the end of our employment to give us plenty of time to leave the country with cushion so there was not a gap in coverage.

Rent a storage unit, if you are moving out of your residence.  Start packing and moving things.  Set up insurance on your storage unit contents.

Book your house movers if this is applicable to move your possessions into your storage unit or elsewhere.  Keep items for which you will need quick access handy for when you return.

Set up dates to have your insurances cancel.  These would include home, cars you are disposing, etc.  We kept base limit insurance on the car we are keeping but removed collision.  Talk to your insurance provider on the liability coverage limits (e.g. vehicle, home) required to keep any umbrella policy in effect.

Hand in your resignation letter with your final dates, if you have not done this previously.  Make sure it is professionally written and cites the reasons for your departure.  Don’t forget to write thank you notes to all of the people in your company who have helped you along the way…leave a good impression!  Get recommendation letter from your employer if possible.

Make sure that every account you have in your life is set up on paperless statements so you can keep up with everything through email.

Ensure that every one of the bills that you will still have are set up on auto draft.  This could include insurances, mortgages, etc.

Make electronic copies of your important documents and upload these to the cloud.  This would include estate documents, passports, drivers licenses, travelers insurance, birth and marriage certificates, etc.

Set up a tax folder in the cloud where you can store everything for easy transfer to a CPA or for use with online software.  File your taxes before you leave if possible and alert your CPA to the potential of an extension for the upcoming year.

Confirm that your contacts are all saved to the cloud.  I say this because I noticed that a portion of my contacts were on the company Outlook account and not on my phone and cloud account.  I switched their housing so as not to lose them when I am disconnected from corporate email.  Also confirm that you save all important contact information for people who you do not already have on your phone.

Learn how to build a website and start your travel blog.  We ended up using WordPress, but there are a lot of options out there with various features and options for scalability.  Depending on your technical knowhow, this could take a little time.  It generally takes 4-6 weeks for a new site to show up through Google, if that is your intention.

Don’t Forget Your Underwear!

T-last minute

Send in a change of address form to forward all mail to its appropriate place if you are vacating your home.

Patagonia Round the World backpacking travelChange all of your account addresses to your forwarding address.  This is exhausting and there are way more out there than it seems.  This could include life and disability insurances, utilities and cell plan (for where to send final bills), attorneys, CPA, brokerage, all banks, mortgage companies, pest services, retirement accounts, general insurance companies, pension, identity protection, doctors and dentists, associations or credentialing agencies…

Get your cell phone unlocked so it can be used in other countries.

Designate a power of attorney for specific tasks which you may need help with while you are gone (e.g. closing on your house or turning in a leased vehicle).

Make sure you have gotten all items on your packing list.  Pack your bag again and make sure everything fits with a little extra room incase you need additional or different items along the road.

Get some cash to bring.  Several countries require crisp, new US Dollars upon arrival for Visa issuance.  You will also find some tours require cash (US) for local payments to guides, etc.  Africa comes to mind.

Cancel everything you will no longer need such as utilities, cell plans, cable, Netflix, your paper subscription to Model Airplane News…

Pack.  Photograph all of your gear for insurance purposes.

So now that we’ve convinced you to prioritize travel, get out and live and not merely exist.  Make sure you don’t burn bridges and turn in your proper resignation letter.  And while your preparing, learn how to pack for your world trip without lugging around a stupid roller bag.  And we highly recommend checking out posts from these other countries for a little inspiration:

Grand Canyon cliff view before career break travel
You’ve reached the cliffs edge

As promised, here is a condensed version of our round the world travel planner in list format:

  • One year before departure
    1. Start preparing budget and live accordingly
    2. Start going through your house and getting rid of the things you don’t need
    3. Purge your filing cabinet
    4. Research the option for a Leave of Absence with your work
    5. Start preparing your itinerary
    6. Get your estate and documents in order
    7. Set up a meeting with your financial advisor
    8. Research benefit and vesting dates with your company
  • Six months prior to departure
    1. Get or update your passport and update emergency contact info
    2. Set up your vaccination/travel clinic appointment
    3. Fine tune your itinerary
    4. Work on packing list
    5. Tell friends and family about your career break plans
    6. Determine what to do with your pets while you are away
    7. Consider sale or rental of your home or lease end dates
    8. Set up traveler friendly accounts, debit and credit cards
    9. Set up your final doctor and dentist appointments
  • Three months prior to departure
    1. Research travel insurance
    2. Purchase big-ticket items (camera / laptop)
    3. Get your travel pack / backpack
    4. Research visa requirements and apply for the first ones needed
    5. Decide on what to do with your vehicles
    6. Get your rental homes under proper management
    7. Finalize estate documents with notarizations
    8. Update your resumé
    9. Allocate investment accounts
    10. Apply for an international drivers license
    11. Alert your job
    12. Purchase initial plane tickets
  • One month prior to departure
    1. Alert your financial institutions with location plans
    2. Download e-books
    3. Purchase travel insurance
    4. Rent a storage unit
    5. Book your movers
    6. Set cancelation dates with insurance providers
    7. Hand in resignation letter
    8. Set all accounts on e-billing and statement
    9. Set all accounts on auto draft and deposit
    10. Upload all important documents to the cloud
    11. Confirm phone contacts are save properly
    12. Start a tax folder in the cloud
    13. Start your blog
  • Last few days or weeks before departure
    1. Change your addresses on all accounts
    2. Send in change of address to post office
    3. Unlock phone for international use
    4. Get cash
    5. Confirm that all items on packing list are in hand
    6. Cancel utilities, etc.
    7. Pack
  • Day of trip
    1. Set alarm
    2. Don’t forget to bring your stuff
    3. Pinch yourself, you are about to have an awesome adventure
Sailing BVI round the world backpacking travel
Smooth sailing

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