Caroline Gregory

1 Year Nomad Life: Q & A

Caroline Gregory
1 Year Nomad Life: Q & A


I have officially been backpacking for one year. My travels have brought me across Thailand, Myanmar, Laos, Cambodia, Malaysia, Indonesia, Singapore, the US and now I write this post from India. 

Last week, I opened the floor to my readers /~tribe members~  to submit questions about my travel lifestyle.  Here I feature 20 of those with my answers.  Thank you for the continuous support of my journey and my being.

I hope your lives are well.  May we all honor our happiest methods to the madness.

1. When did you first decide you wanted to travel full time?

I made the decision in early 2015 and left on a plane a year later.  I needed to do something wild.

2. How did you prepare for your trip?  Not financially, but routes, guidebooks, places to stay, etc. and how helpful was that for you once on the road?

All of my prep work was U.S. related.  I had to sell my car, move out of my house, cancel my insurances and phone, buy travel gear, give away things, set up a new bank account, etc.  I had read some backpacking blogs and learned the basics. I wasn’t completely in the dark.  But prior to traveling, my life was very structured so I was looking forward to the opposite of that.  I arrived in Bangkok with nothing booked and no plan.  The next day I thought maybe I’ll go North first and then a friend invited me to meet him in Krabi so South I flew. 

3. How much money have you spent so far?

$13,500 in one year.  9 countries.  I flew at least 15 times including a roundtrip between Bali and California.  Also, attending Burning Man is not cheap. 

Some of my passport tattoos.

4. How do you support yourself through your travels?

I have money saved and I make art. I sell 3 or 4 paintings a month which cover most of my expenses.  Read this post about how I afford to travel.

5. How do you access the money you’ve saved?

I have a Charles Schwab debit card that doesn’t charge ATM fees.  I also use my travel rewards credit card whenever possible so I can earn more miles and fly free.  If you want an invite for the rewards card, email me here.  I monitor both cards with online apps.

6. Which place that you have explored is your favorite and why?

Bali, Indonesia for its diversity. Between the nice beaches, jungle, rainforest, mountains, volcanoes and rice fields, everywhere you look is a beautiful landscape. Great food and full of things to do. I think I’ll raise my future kids there.

7. Are you traveling alone?

Yes, but I travel with other backpackers more often than I go solo. I came to India with a girl friend I met in Bali.  We linked with a cool group of guys in Goa and now I’m traveling with them. The guy to girl ratio between backpackers is like 10:1 in India so I’ll probably travel with more guys while here.  Women don’t come to this country as often, which I like because all the women I do meet lately are dope and have that ~on a mission~ vibe.

8. How do you get from place to place?

Asia has cheap airlines so I like to fly between countries.  City to city, I take buses or trains. I'm most happy on trains in India because they're cheap and very comfortable as opposed to bumpy bus rides along pot-holed roads. Also, locals come on at the stops selling chai and samosas for pennies!

One of the day trains in India. Women's cabin.

9. How do you find places to stay?

Hostelworld app.  You can search by city and see pictures, read reviews and reserve a bed.

10. Are language barriers a struggle?

Yes. Sometimes I have to be creative and play charades to find what I’m looking for. I never let it stress me out though. Unless the matter is super important, I actually appreciate the upside to not knowing all the languages.  For example, even when I don’t mean to overhear English spoken around me.. I do. The words register as something I understand and they distract me.  I like that other languages become white noise and I’m able to tune them out and be in my own moment.  How much of what you hear around you is actually worth having heard?  Also, smiling and laughing are universal.  These connections can often be better than word exchange.

11. How have other cultures been about you being covered in tattoos?

Most of the people respond kindly to me and seem fascinated.  I get a lot of “nice tattoo!” comments and questions about if they’re real or where I got them done.  Many also recognize my OM neck tattoo and get happy.  My friends love to walk a little behind me just so they can watch the reactions to my appearance.

12. Have you encountered any dangerous people, animals or areas?

Yes.  Until recently, I hadn’t been around any dangerous situations besides territorial street dogs.  The other night, my friend and I were woken up by hysterical screaming and crying outside.  A few girls I knew were having a bonfire so I rushed out there to make sure they were okay.  One of the girls had been held down by local men, hit and had some of her dreads purposely pulled out.  

13. How do you know if you’re in a safe area?

I don’t truly know, but I trust my gut.  I learn tips from locals and backpackers about where I am. I don’t explore at night by myself unless I know the area well and have determined it okay to do so. I walk confidently and don’t make myself an easy target (no headphones in, no playing on my phone) and if I see local women around, I feel better.  If someone is creepy or I don’t like where I’m staying, I make a change.  Putting up with an uncomfortable situation is not worth it.

14. Is it necessary to have a license to rent motorbikes in these countries?

By law, yes. Its not hard to rent a bike without one though.  You’ll want to have money in two separate places.  One pocket for the majority and another with the equivalent of a few dollars so if a cop wants to be paid off, you give him that.  We had three people on the motorbike the other day (not allowed) and a cop wanted 1500 indian rupee and we got him down to 100 lol. I don’t see cops often, depends on the city I guess.

Garden of the Gods, Colorado (Summer road trip across US)

15. How often do you talk to your family?  Do you miss them?

I love and miss my family of course !! They’re very supportive of me and I’m thankful for that.  We text every few days and talk on the phone 2-3 times a month.  Both of my parents look at my social media and read my blog as well.

16. How long do you plan to keep traveling?

Another 6-12 months.

17. What is a travel goal you haven’t achieved yet?

Travel across a country by horse.

18. Where do you find inspiration for your art?

Nature, high power conversations and the occasional use of hallucinogenics.  Instagram is also the portal to infinite talent / inspiration.  I try to follow only artists so my feed is full of art.

This is a mandala by @hoxxoh in Miami, USA.  I love his work!

19. How hard was it for you to break off from societal norms?  I’m an artist and I struggle daily with people telling me I’ll go nowhere with it.  

Hard maybe in the beginning, but it was gradual for me and felt natural.  At first I only had dreams and didn’t realize.. wait I could do these things.  So when I started getting tattoos, teaching myself to paint, etc., I felt really great about expressing myself.  When you stop worrying about the views of those around you, you start to become this powerful being in charge of your vibe.  Understand that what others have to say about you is a reflection on their inner state.  Let them be, let them grow into themselves further and find their passions / happiness.  If they had achieved their own already, they would have no reason to knock you or yours.  If your people see you are genuinely happy and still have negative things to say... I don’t think they are your people.  Achieve your happiness however you want.  If you love art, make art! If you love challenging social norms for how to look or dress or be, run it.  I believe in you.

20. How do I give up everything and do what you do?

Start by narrowing your focus so you can work towards a real goal.. not just the broad statement of “I want to travel.”  Where do you want to go?  For how long? Estimate the budget you’ll need to save for and factor in the cost of your gear.  Decide to leave maybe a year from now so you have time to make money and prepare your current situation for the change.  If you don’t want bills back home, make a list of what you’ll need to cancel and things you'll need to sell before leaving.  Some of these details take time or multiple calls. You have to make your travel goal a priority and choose it over temporary desires. Like new clothes, getting your nails done or eating out every night. Seeing the world looked far cooler (to me) and worth not splurging on those other things while I saved up.  Keep in mind, that the older we get, the more responsibilities pile on that make traveling difficult. This doesn't have to be the case for you.  Life on the road and living minimally are quite simple once you get started.

Honor the fire within you and buy a plane ticket into the unknown abyss. We have backpacks.

Love and light,


Perhentian Islands, Malaysia