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If Not Now When….
How many times have you heard someone say:
I’ll travel when.…
- I retire..
- Someone can go with me..
- When student loans are paid off…
- I’ve got more savings…

And by the time they can retire, life happens, (or worse, it life ends), devastating health issues surface, parents’ health issues, and the Travel dream exists perpetually elusive; relentlessly out of reach.
When I say “travel” I don’t mean for a week, in an all-inclusive Resort Bubble.
Not to knock the “Resort Bubble”, it can be a lovely way to decompress for a week, but it isn’t really Traveling. Of course there are constraints to consider.
Image above generated with Chat GPT / DALL.E
Ask: yourself these questions:
- Time: Are you working? Do you have vacation time saved up? Are you between jobs or semesters? Are you retired, semi-retired? Do you already have a remote job? If you do, then the hardest obstacles, aren’t obstacles. You just need reliable internet and workspace.
- Budget: How much can you afford to spend? Is there anything of value, you don’t need, that you can sell?
- Overhead: Do you have a lease expiring soon? Is there a place, family member’s basement, storage unit, you can stash your stuff for a few months? What are your monthly expenses for food, and utilities? The savings on that alone may pay for a few more days. Can you sublet your apt / house while traveling?
- Health: What can be managed in transit? Can you bring enough meds? Locate a doctor, clinic, hospital close to where you are staying. Do you have mobility restrictions? Be realistic and see what you can work around.
You’d be surprised how far a little savings from USA / Canada can get you in developing countries especially, if you are open to renting an apartment or a room with communal spaces. Some guest houses offer communal breakfast, others; kitchen access to make your own. After pooling ingredients with your transitory housemates to make a communal omelet, and 3rd rate stale coffee, you may look around the table, feeling warmth and realize that you’ve found YOUR tribe.
When you wake up or log off, you could chose adventure, a new path outside your door rather than retreating to the couch hunting for a new series to stream. Not to knock Netflix, but too much can steal time at an alarming rate. Post Covid technology and infrastructure, has afforded many with the life altering opportunity to work Hybrid and Remote. Yet, many with the resources, are still hesitant to forge a path working from a different country or even a different location within their own country. And to those souls craving change and adventure, I ask…
If not now, when?
I’ve worked online and traveled for 10 + years, often heading out alone and dealing with multiple sclerosis drama before the “Digital Nomad” tribe even had a name.
Are you in your 20’s with a college degree? Why not teach ESL overseas? Korea, Japan, Taiwan and China tends to pay the best and you should be able to save some money to pay loans or travel. Plenty of other countries have teaching gigs that will cover your basic expenses, if there are other parts of the world you want to explore as a teacher. You usually don’t need a teaching degree and reasonable cost of living and affordable or cheap healthcare you may even end this adventure chapter with savings. After many years, this ESL website www.eslcafe.com is still a great resource for travelers that want to live overseas for a year or more Do you work for a big company? Is an intercompany transfer an option for a few years? Do you have $500, 2 weeks free coming up, and a decent credit score? Why not apply for credit cards that have points offers high enough to cover the r/t airfare?
While I wouldn’t trade my travel life for anything, traveling and working remotely does not always proceed as smoothly as the barrage of social media posts depict. Newsflash! You don’t always look fabulous and it doesn’t always feel like you are living the dream at that moment… even if you are
Quite the contrary, sometimes…
- Your stomach is in turmoil and you find yourself frantic to locate a bathroom and when you do…it is the stuff of nightmares.. and there is no TP!! And nobody wants to see that on Tik Tok… or do they?
- Naively, you believe that you are triumphant, bonding with wildlife, you’ve trekked from a far to engage, only to find your new creature friends abruptly revolt, forgetting the goodwill you purchased, via snacks they were greedily gobbling up just moments ago! Note: Salamanders and hummingbirds are wonderful mystical creatures that have never attacked me.

- When internet is not available, you may revert to charades indicating that you’d like to order fish and find yourself eating ginger snake soup … AGAIN… frantically striving to remember where the “safe” bathrooms are and how to pantomime that?
Image above generated with Chat GPT / DALL.E
With all this in mind, traveling, working remotely, living part of your retired life overseas can be a blast and there is always something to learn! For some of us, that rush feeds the life force. It is important though to do your homework especially, if you are traveling alone or if you’ve got health issues to contend with.
Don’t assume that health issues will rule out travel. You may be surprised to find high quality specialists readily available on short notice, often in English for less than the copay in your home country. Prescription medicines may be available over the counter and at a fraction of the cost at home.
Sure there are logistic factor to address with a Digital Nomad lifestyle (See link Digital Nomad Checklist) but now there are affordable workspaces and “work friendly” cafes all over the world now geared towards Digital Nomads. Nomad spaces typically have the strongest internet locally available and often affordable small conference rooms for sensitive work calls.
Don’t want to share your travel plans with your employer? Get a VPN for a few dollars per month (though not recommended for military contracts) .
Don’ t have money for airfare? Exploit the “bonus offers” on travel oriented credit cards.
This website is intended to share travel tips, hacks, and stories including the disasters, which in retrospect infuse vibrancy to the tapestry of a life well lived. Sometimes you may travel with a specific destination or goal in mind, and sometimes, you just want to drift…
