43 questions to check if you can be a lifestyle entrepreneur or digital nomad

See that photo up there? It’s BS by the way. Tried and tested, and it only got my eyes freaking tired, with sand into laptop while my ass heats up to cook my balls.

When people know about our travels (Debbie and I try to do 90 days of travel a year, minimum 60), they always envy our lifestyle, and ask us how we did it.

Frankly, the how-we-did-it question is not even close to the real question they should be asking, which is:

What are you getting into?

And truth be told, there’s nothing much to envy about, which is why we hardly share our check-ins and travels on social media. Unless it’s something too stupidly funny. 🙂

Inspired by a post by Marcus Teoh, Debbie and I decided to compile a list of questions that should help you decide if being a lifestyle entrepreneur or digital nomad is something you really should strive for.

#1. Can all your belongings pass the 7kg rule of AirAsia?

Thanks to some crazy passengers who couldn’t even lift their carry-ons to fit in the overhead cabin and went on social media to trash the air stewards (which frankly, is not really their job to begin with), the max carry-on weight has been enforced for a while.

Weigh your current laptop bag now, and you’ll realise that as much as Apple advertises it’s ultra light MacBooks, you have only 5kg of carryon weight left. I can’t attest for Debbie (God knows how she fit her stuff in), but I’m used to bringing 4 black tees which doubles as PJs, 2 quick dry shorts, a couple of underwear (don’t ask me how many) for a 30-day trips. As efficient as we are in packing, our personal best was 6.5kg.

Oh yeah, for girls with long or thick hair, you have to bring along a hair dryer too.

Workaround you have to be ok with:

  1. Buying your toiletries when you’ve arrived.
  2. Washing your cloths at night and hoping it will dry in the morning.
  3. Wearing a sweat-fill, mud-spat, tar-burned shirt for a day or two.

#2. Can you live like the locals?

Every country have a certain routine around them, and when in Rome, you can’t do what the Malaysian do. This includes living conditions, endless battles with local bugs, weird food (see below), having no clean water or electricity, no consistent internet, or having your favourite social media sites blocked (invest in a VPN, Debs says)

#3. Are you ok with street food?

Unless you can afford eating at restaurants and bars everyday, you gotta eat what the locals eat. Picky eaters, you just gotta be rich or pray hard, and sometimes you gotta do both. Some local food can be extreme in one sense, and I’m not even talking about being gassy or getting food poisoning.

And food court is NOT street food. It’s literally those beside the street/highway, where every zoom-by of a vehicle adds grounded spices into your noodles.

Workaround you have to be ok with:

  1. Eating micro-waved or toasted pre-cooked food at 7-11
  2. Spending more than when you’re in Malaysia on food

#4. Have you ever lived at a foreign place for more than 7 days?

One of the places I personally love is Krabi, Thailand, where I can stay over 2 weeks at a time. Upon hearing that, most people would go like, “but there’s nothing to do after 3 days!” That shows 1) that they are still thinking like a tourist, and 2) they are not thinking about living there.

An experiment of experience:

  1. Try living in Penang/Ipoh/KK/Cameron for 7 days, but not with existing friends or relatives.
  2. Those few cities are easiest to begin with, and if you can’t do that, gotta rethink about continuing with this post.

#5. Are you ok with spotty internet?

Not everywhere you go will have solid internet, and a dash of rain or a hint of devil-worship may leave you disconnected from the WWW. Do you know how to get the tether to work on your phone, or spotting places with decent internet connection?

An experiment of experience:

Walk around town this weekend with your mobile internet disabled. You can only use public or private wifi spots.

#6. Are you ok living in a dorm?

Again, unless you’re rich, chances are sometimes you’ll end up in a mixed dorm, with anywhere from 4-in-a-room (super luxurious) to 20-in-a-room.

Dorms are a great place to make quick new friends, and to chat people up. Of course, you will have to sleep through snores, insensitive loud speakers (both human and device) and 4am drunk talk. I guess you’ll also have to be ok not sleeping in an Instagrammable pose.

#7. Have you ever slept in an airport?

Late night, super early or just weird layovers. If you ever go to KLIA for a 6am flight, you’ll see many people sleeping all over the airport. Being a digital nomad means you’ll be one of those people quite often.

#8. Can you work alone?

If you need to have colleagues to work together-gether with you, eat together, make coffee in the pantry together, seriously, stop reading now.

#9. Can you focus for 90 minutes of work?

Sure, you may clock in at 9am and out at 5pm, but honestly, you should know you can’t always get to concentrate on your work. Bosses will drop in for a meeting, your next-cubicle buddy just asked what you want have for lunch, the tea lady decided to tell you about her new room mate, you check your inbox, in-tray and fax-tray every 5 minutes… the distraction are endless.

To be an effective lifestyle entrepreneur, you have to be able to tune off all distractions, switch off all disturbance and identify your best work time, and commit to finish your work within a set time.

An experiment of experience:

Go to a cafe this weekend and try to work for a solid 90 minutes on your project or finish that long-overdued Udemy course.

#10. Have you ever been in a 6 hour van ride with a broken A/C, 4 pax passed capability and luggages squeeze to every inch of your life?

Unless you can afford private planes, some places will require you to go through a commuting experience of being smuggled.


  1. Take motion sickness pills that are not herbal-based, because those hardly do shit on hard turns. Those that can knock you out and leave you drowsy still after 3 hours are your best friends.
  2. When in a van, always sit as front as possible. You don’t want to test the suspensions of the back wheels.
  3. Get a scarf. I’ll explain why further down.

#11. Can you walk for long distance with a 7kg load?

Sometimes there just aren’t Ubers, Grabs or cabs around. Other times, the drivers are just too lost and decided it’s better to just dump you by the road side.

Regardless, you have to be comfortable walking for hours at a time under the hot sun or heavy rain, which both circumstances will leave your underwear soaking wet.

#12. Are you ok with no night-entertainment?

Some towns literally sleeps at 8pm at night. Sure, there will be a couple of bars, but they often leave you wanting to go home and stare at a wall more than being there for another 30 minutes.

#13. Can you make friends easily at a networking event?

Even as an introvert, you gotta know how to make friends with your dorm mates, co-working space mates, 3-hour van trip mate etc. It’s not about trying to be friendly or getting used to loneliness (it’s not the same as a 15 day silent retreat). Making friends on the go can literally save your life. Shit can happen at every corner, and you gotta know how to ask for help.

So if you’re still used to calling mommy, daddy, hubby, wifey or doggie whenever you’re in trouble, stop reading now.

#14. Have you ever left your laptop behind at a cafe while you take a dump?

Unless you have an augmented bladder or bowel movements that responds to the snap of your fingers, there’s a chance you will have to leave your laptop behind for a few minutes while you rush to the toilet (if there is one nearby to begin with).

An experiment of experience:

Leave your laptop for 15 minutes the next time you’re at a crowded cafe alone.

Dumbass tip:

Take your phone, wallet and passport with you. Seriously, though everything can be replaced, without those three, you’ll have a crazy tough time.

#15. Can/do you self-medicate?

Do you know the ingredients of your usual meds? Because sometimes, the only options are fakes and you gotta take them no matter what.

#16. Do you have a bankable skill that is remote friendly?

This is an entire blog post on it’s own, but if you want to be a freelancer that’s working remotely, the usual bankable skills are web-design, web development, app development, writing, graphic design, social media management etc.

Other less common skills are online trading, e-commerce, online coaching, online training, blogging while getting paid, vlogging while getting paid, yoga and all the similar new age stuff etc. Though prostitution and escort services are not recommended, I guess it’s ok for a desperate guy to earn some quick bucks at this weekend’s bachelorette’s party.

#17. Are you ok with your friends and family members complaining that you didn’t buy souvenirs for them?

Unless you’re ok lugging around extra weight and probably checking in a bag on the way back, you just gotta manage their expectations before you leave.

#18. Do you OT to get your work done?

It basically means you have bad time and relationship management, something you will have a big challenge when you’re on the road. If you can’t manage your time and resources well, or be able to buy more time from your team or clients, then stop reading now.

#19. Do you need more than 3 bottles of liquids in your toiletries?

Er, yeah, if your answer is “but…but…but…”, then stop reading now.

#20. Are you ok with any brand of bath/shampoo/toothpaste?

Same as before.

#21. Can you sleep easily on different beds/pillows/surfaces?

See that special childhood pillow you gotta hug and sniff in order for you to get a good sleep? That has got to go.

An experiment to experience:

Dump said pillow.

#22. If you’re currently employed, do you know how many MC and AL days left?

If you can answer in less than 3 seconds, stop reading.

Cause when you’re on your own, there are no such things. Even when you’re bed-ridden, you may still need to get the project done because your clients are expecting by the end of the day, which may be 4am your time.

#23. Can you take a Skype call at anytime of the day?

If you’re complaining that your bosses are calling you at odd hours, this is something at another level altogether. Because while it’s an odd hour for you, it could be 9 to 5 for your oversea’s clients.

#24. Are you resourceful?

If your answer to usual questions is “don’t know”, then stop reading now.

#25. Are you tech-savvy?

If you don’t know the how to power-off your hung Mac/PC without calling IT, then stop reading now.

#26. Are you ok with a very blurred line between work and play?

If you’re the kind that don’t talk about work when with family (which I would ask then what do you talk about, seriously?), have to separate work from life, then you may want to rethink being a digital nomad too. Work and life is usually very blended, and your clients may call you during your dinner time, rushing you to finish a last minute thing.

You know how people say that you gotta love what you do? It’s real when you’re a digital nomad or lifestyle entrepreneur.

#27. Are you always on Malaysia time?

If you can’t be punctual and is always on-the-way, then stop reading now.

#28. Do you know this thing called Google Translate?

Google it the moment you stop reading, which is now.

#29. Do you go for regular salon visits, manicure, pedicure?

Ok, I’m a bald guy, so I can’t say much, but seriously, if you have those on your calendar and can’t miss your usual hairdresser, then either go bald or stop reading now. If not, get a dry shampoo like what Debs did.

#30. Are you okay hanging with stinky people?

This may be a personal thing, but we have hung out with some travellers and backpackers, who don’t take baths or have a change of cloths every other day. Or week. And this is in a climate that’s hot as hell, where you can lick off the salt off your the top of your shoulders.

This explains the scarf I mention in point #10.

#31. Can you get urgent work done under a hot sun and a bus stop?

No excuses, no complaining. I’ve worked on a 6-inch stool before just because the job is time sensitive and last minute.

#32. Is your shoe waterproof, stinkproof, hike, run, walk-friendly?

Yes, I’m talking about one shoe that does all that, and Debbie and my favourite is Keen. It’s not the prettiest shoe you’ll ever wear, but seriously, no other shoe brand comes so durable and practical as Keen. Heck, you can even throw it into the washing machine to wash it, and it doesn’t get those wet stenches.

Keen has to be your primary shoe, and your back up is a pair of disposable flip-flops.

#33. Can you take cold showers at 4.50am in the morning?

If you need a water heater to survive, stop reading now.

#34. Are you ok with your water tasting not Malaysian?

Some places you go will have the water tasting a little saltier, a little bitter, or just plain weird. It’s clean water, no doubt, just with some non-Malaysian flavours. Either drink coconut water all the time, or risk dehydration. Your choice.

#35. Can you stand caucasians asking why you still live under a scandalous ruler(s)?

Ok lar, with I am not gonna say so much about it, but a couple of times, Debbie and I felt kinda stupid when we’re asked why do we still succumb to the treatment in our country.

A good mindset trick I learn: even when you’re in Malaysia, live like a tourist. Ever felt that you’re less sensitive to the local political scene when you’re travelling? Same concept.

#36. Can you live without high heels?

As much as you can say stilettos can be a weapon when you’re attacked, I would say being able to run fast trumps that.

#37. Are you ok throwing away stuff you just used twice?

Some stuff are not airplane friendly, while other times just a one time occasion that you need it. If you’re constantly thinking like a hoarder and maybe-I-will-need-it-someday, then stop reading now.

#38. Will you pay more for accessories that are more practical?

Need I say more?

#39. Do you have an overseas medical card?

Shit can happen when you’re overseas, sometimes leading to you being hospitalised (spoken from experience). Get a good travel insurance at ~RM300/year, because seriously, medical bills can cost you more than you think. I can recommend my agent which I trust with my life, cause literally, she manages everything for me. PM me if you want her number. It’s easy because her husband is my school mate, and I kinda know where his mom stays. #leverage

#40. Are you okay living with a bunch of party goers who comes back at 3am in the morning?

Two words: Ear plugs.
Three words: Live with it.
Four words: Or stop reading now.

#41. Are you okay with the overseas withdrawal fees?

If you don’t know that most of your local ATM cards can be used at foreign ATMS, then booyah, you learned something new today. Just activate it at your nearest branch of ATM.

But if you are stingy with the withdrawal fees and the conversion losses, then please be ok carries tons of cash around everywhere you go.

#42. Do you know how to fix your broken laptop?

If you’re using a Mac, with Apple Care, you’re in luck. Make sure your non-Mac laptops have international warranties.

#43. Do you know how to avoid a bribe?

You will be extorted by the local authorities sometimes. Hey, they gotta eat too, right?

Unless you wanna pay something exorbitant or risk wasting hours at the police station for no reason, here’s what I suggest. Have only a couple of notes in your wallet, and shop said wallet to the person. Keep the rest of your money in your shoe, socks, or like how your mom/grandma would advice, in your underwear.

So WOW?! You got this far?! The next time Debbie and I are out for a 30-day trip, join us.

But if you answer to that is, “huh, so long ah?”, then seriously, for the last time, stop reading.


Co-Founder of KICKSTART by night, Talent Development Consultant, organising workshops and conferences by day, and full-time single dad in between, Maverick is pretty much a renegade. An ex-monk who's always first to ask "why not?", Mav enjoys hacking the way things are done, and pretty much happy with the success rate of 50% (coz sometimes mom is right after all...). When it comes to business, give him a million bucks and he'll most probably get a new set of gadgets, drive home an Audi R8 and reload his Starbucks card. But give him little to nothing, and see how he starts switching on the little brain-matter between his ears. Challenge ACCEPTED!

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