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6 Travel Challenges You Weren’t Expecting

Updated: 2 days ago

As a general rule, if you are travelling to various destinations (as opposed to going on holiday and staying in a hotel), the best way to prepare yourself is to embrace the unexpected. Celebrate each surprise as part of the experience.

Whether you’re a digital nomad, traveller or infrequent flyer, these ideas, all of which based on my personal experiences, can help better prepare you for any upcoming trips you’ve got on the horizon.

Inefficient systems

Depending on the country, systems will be streamlined, digital and efficient, to a greater or lesser, extent. In Australia for example, you can register and open a business online in 30 mins whereas in some countries, merely the reliability of electricity can’t always be guaranteed.

Plan ahead where possible and be open-minded enough that where the system “fails”, use it as a test of your adaptability.


In my humble experience, “work-ations” don’t work, whether I’m home, away or nomading. It’s always better to decide which you are doing; travelling or working remotely so you don’t do each one half-heartedly and then spend your time moping around feeling guilty about one or the other.

If you’re a digital nomad, it’s fundamental to organise an efficient workstyle and flow based around your work, efficiency and lifestyle. One of my favourite models has been a 5x4x3 model:

5 hours x 4 days x 3 weeks but you need to explore what works best for your work.

Hustlers vs Helpers

If you’re reading this, you’re probably already quite familiar with this common scenario:

You book a tour. A local guide chaperones you. He/She takes a sudden detour to a store or craftsman.

They hang around until you buy something or until you get fed up and insist on leaving.

Not exactly what you signed up for.

There are however locals who are genuine and will honestly take care of you. These people can make for an incredibly unique experience and show you the best places to eat, cheapest areas to shop, safest spots to socialise and unveil hidden gems off the beaten track.

How do you find them? One of the best ways I’ve found is by taking free-walking tours and asking the guide for recommendations. Either they will personally help you or suggest someone better suited. Another option is asking a person you’ve made conversation with (barmen, restaurant owner etc) if they know anyone and very often, they’ll suggest a relative, which is usually a reliably option.


Ever rented somewhere to stay and the description didn't quite match the reality? Weak wifi, lack of cooking facilities, dangerous area? There are so many uncertainties.

My suggestion is to have the purpose of your trip clear and know what your priorities are. If you are working, search for accommodation that has been verified by other digital nomads or choose somewhere near other available rentals (Airbnb can help relocate you a lot easier that way) and/or a reliable co-working space.

Co-living spaces are all the rage now, offering not only comfortable accommodation and workspaces but community-based experiences and activities to interact with others like you.

Pro Tip: Always contact the Host in advance instead of instant booking, for any particular needs you may have and check they can meet them. Otherwise, you may be severely disappointed.


On a recent business trip to the UK, it only occurred to me half way through that I hadn’t used cash for any type of purchase, not once! I used my card on every occasion.

Despite the convenience of cards, a cash backup is still useful because things can and will go wrong, even in the most advanced countries. Card machines break, wifi stops working, withdrawal limits and high conversion fees.

It’s also worth mentioning (from experience) that withdrawing cash from an ATM may require careful planning in some countries due to currency restrictions, electricity shortages or simply a lack of availability (memories of Havana and Holbox island).

Cash is your “get-out-of-trouble” card you never know when you’ll need, especially if you ever need to pay-your-way out of danger.


As a former language teacher I cannot stress this one enough: learn the most important local expressions and carry either a digital translator or a book (yes, go old school).

Not only will certain expressions be useful in times of need or urgency but it helps you integrate far better with local people when they realise you aren’t ‘just another tourist’, in your own world.

Basic interactions and short conversations go a long way. Useful people to make an effort with include: restaurant or small business owners, barmen, local officers, doctor/pharmacist, custodians and anyone you see more than once on your journey!

Which surprised you most and how would you react and resolve if you found yourself in a bad situation abroad?

Wishing you the absolute very best,



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