82 Lessons from 15 Years of Travel and Entrepreneurship

1. Things go wrong when travelling (and in business!)

It’s not all sunshine and rainbows if you’re travelling the world for any real length of time you will encounter challenges. Missed connections, pesky policemen, biting insects, diarrhoea, swallowed bank cards, frustrating visas, crashed motorbikes and challenging people are just a few of the things I’ve come across on the road. Travelers make mistakes – problems do arise and things DO go wrong.

Likewise, starting an online business is fraught with plenty of opportunities to make mistakes. The important thing is learning from your mistakes and remaining positive, after all…

2. It’s your attitude that counts

When things do go wrong, it’s an opportunity to develop confidence and problem-solving skills. A positive attitude and a sense of humour can help you overcome most problems. Remember, it’s never as bad as it seems. The more scrapes you get yourself into, and out of, the more capable you will become.

3. Getting off the beaten path alone can teach you a lot

Traveling solo gave me some of my most cherished travel memories and when I was solo and truly off the beaten path, that’s when the magic happens…

4. But you don’t have to be alone

Even if you are travelling in places with no other backpackers, it’s usually pretty easy to meet other like-minded people. On the road, you never have to be alone – unless you want to.

5. It’s always worth learning a bit of the local language

Just knowing how to say ‘hello’ and ‘thanks’ will make people smile, it shows you are making an effort.

6. But language skills aren’t essential

In Pakistan, I spent four days in a log cabin with my French friend and two police officers assigned to keep an eye on us. Neither of them spoke a word of English but we had long conversations all the same. They were quick to teach me ‘pass the joint’ in Urdu.

7. The world is mostly safe

I’ve been to lots of countries that worry my mum, and I’ve been told by others that by going to places like Venezuela and Pakistan, I’m risking my life. Whilst I have had quite a few near-death experiences, these have mostly been my own fault on account of seeing myself as invincible. (I have now learned from this and included it in The Broke Backpacker Manifesto.)

I’ve rarely felt threatened by others and the only external danger I’ve regularly faced is crazy traffic. In general, some of the most ‘dangerous’ countries are the most friendly – as the locals are aware the media has portrayed them poorly and want to welcome foreigners.

8. Trust those who have been (and ignore the haters)

Before I went backpacking in Venezuela, a lot of people told me I was going to be kidnapped. Before hitchhiking across Iran, I was warned I would be robbed. Before Pakistan, some very misinformed people told me I would be beheaded.

These guys all had one thing in common: none of them had been to the country they were so terrified of. Weak minds are influenced by propaganda the media – don’t let people pass their own insecurities and doubts off onto you. Ignore those motherfuckers and trust people who have actually been.

9. Iranians are the most hospitable people I’ve ever met

Iran is the easiest country in the world to go hitchhiking in. I never had to wait more than a few minutes to get picked up!

I was invited in for tea, offered a place to stay on numerous occasions, and fed until I was about ready to pop… Iranians are amazing people.

10. Monkeys are bastards

Picture the scene. After a brutal one-hour hike, you finally make it to a magnificent and abandoned Indian fort with an incredible view over the valley below. You sit, enjoying a joint, soaking in the majesty that surrounds you, feeling a bit like Indiana Jones.

Before you know it these feelings are dashed as a horde of territorial, angry monkeys, the size of big ass dogs, surround you and try to get at your shit. Valiantly, you fight your way out of the fort and vow never to trust monkeys again. I’ve been burned by monkeys a couple of times, fuck those guys.

11. Rickshaws are slow

Originally, I planned to drive my multicoloured rickshaw nearly 4000 kilometres traveling across India. Little did I know that the maximum speed was 37 kilometres an hour and that it would break down a dozen times a day.

12. True challenges are the ultimate bonding experience

Driving a rickshaw across India with my brother Alex was probably the most stressful and exhausting thing I’ve ever done. A few people drive rickshaws on adventures like this but I’m telling you – none of them have done it in the piece of shit, truly ancient, rickshaw that we had. This was much much harder than we anticipated. 

So many things went wrong on this adventure and luckily our default reaction was to laugh at the ridiculousness of it all, swig some red bull, roll another joint, and keep pushing on. We came out the other side with a much stronger relationship having gone through the eye of the storm together.

13. You can always find a place to sleep

I’ve slept rough quite a few times on my adventures but really, this is very rarely necessary. A kind soul will normally rock up out of nowhere to offer you a place to stay. Personally, I love camping… Camping out in a cave in Cappadocia was one of my favourite travel experiences of all time. Camping on the Deosai Plateau in Pakistan was a close second, except four bears rocked up to my tent and were chased off by flaming stick-wielding soldiers, it was a weird night.

14. You can have a good time on $10 a day (and it’s possible to survive on less than that)

I traveled the world for many years on a budget of $10, or less, a day. It’s possible to have a pretty good time on that if you’re frugal and by being out of your comfort zone, you have more local interactions and learn more …and in many countries, a budget of $10 a day leaves plenty of room for beer!

15. Traveling on a tight budget will help you appreciate the little things

Like hot showers, fresh cookies, a seat with some space, and all of the many acts of kindness that will come your way on the road. The gratitude you develop from trying budget travel is a WHY everybody should try it once.

16. Being short is great when travelling

I am five foot six, a less-than-ideal height when it comes to reaching a pull-up bar but the perfect height for long bus rides and fitting into tight spots. I always secretly chuckle when I see some six-foot giant scrunched up in the back of a bus.

17. A good pair of shoes is vital if you’re going adventuring

I learned this the hard way when my trainers fell apart whilst trekking the Annapurna Circuit in Nepal. I duct-taped them back together and used plastic bags to keep the water and snow out of my socks, it was an uncomfortable two-week trek (but totally worth it).

18. The best mountain scenery in the world is in Pakistan

Thirty of the world’s highest one hundred peaks are in Pakistan and the best bit, you’ll have them all to yourselves. Pakistan is the adventure capital of the world… Go check it out.

19. You will fall in love

In every country around the world, there are attractive people who are looking for the same things – a good connection, good times and good sex. It’s easy to fall in love on the road. I have had some beautiful connections around the world which I will treasure forever.

20. And love on the road moves fast!

Sometimes, you’ll feel like you’ve been dating somebody forever when you actually met just a week ago. This is because you have so many amazing shared experiences whilst travelling that emotions can move fast.

21. Heartbreak happens, and that’s OK…

People are usually heading in different directions and flings end just as quickly as they begin. Fear not, noble Cupid, the next romantic conquest is just around the corner. Enjoy the times you have with your current beloved and don’t worry about the future too much.

22. Sometimes, you need to pursue it, no matter how crazy it seems

But sometimes, you will meet somebody who will blow you away. Somebody who will be on your mind long after you have left them. Somebody who you feel like you are meant to be with, the kind of person who simply gets you and is your ideal partner in crime.

Often, by the time you realise this person means as much to you as they do, you’ll be far apart. But maybe an event will hurl you back together… Maybe one day your beloved sends you a raunchy nude whilst you are halfway up a mountain.

Powered by lust and frostbite, certain now that this mountain ain’t worth the hassle, you turn around, brave a blizzard, hitchhike five hundred kilometres in the wrong direction, convert to Islam, get married, and live happily ever after (until you get divorced a couple of years later).

Hey, it can happen. That literally did happen to me.

23. Plans change all the time

Go with the flow. #Flexible

24. You’ll meet some of your best friends on the road

Travelling is kind of like speed dating except with friends and it’s a good opportunity to find people who have similar values.

25. Traveling makes you think about your values

Your values are the lamp you hold to illuminate the murky roads of life. They keep you steady and on the right path even when it seems like the whole thing might just crumble away from beneath your feet. Developing these values all comes down to discipline and an ability to ask yourself hard questions.

What really matters to you?

• Where are you going, and where are you coming from?
• What traits do you want to nurture and grow within yourself?
• What weaknesses do you struggle with…?

Exploring these challenging topics will help you grow as a person and as an entrepreneur and there’s no better battleground than real raw adventure travel to figure out what matters to you and who you want to be.

Self-development is not just about hammering out push-ups and meditating for four hours a day. These things might be exactly what you need, but it’s the intentions that drive the process that really define self-development.

26. Traveling broke is the ultimate personal development experience

I am a passionate believer that growth begins at the end of your comfort zone. The first time I slept rough in an Indian train station, scary. The first time I stuck out my thumb on the road, also scary. Traveling without any financial cushion and relying on meticulous planning, flexibility, and luck to make it all happen, really scary.

Hitting the road broke will stretch you out of your comfort zone and make you a more confident, more capable human.

27. You can find marijuana in almost every country

Eventually, I’ll have smoked a joint in every country in the world. #lifegoals

28. Visiting Bhutan is like stepping back in time

Bhutan is fucking epic… This is a truly amazing place, utterly unique, where time stands still.

29. There is nothing like waking up to an amazing view from your tent

I love camping… The feeling of being totally isolated from nature is hard to beat. I’ve camped out in more countries than I can remember. Travelling with a trusty tent is smart, especially if you are on a budget, as it means you can find a place to sleep pretty much anywhere.

30. Digital detoxes are good for the soul

I spent a solid six months this year hustling hard on my online ventures and I fucking loved it. It feels great to be building something, however, it’s important to get away from screens and I encourage everybody to try a ten-day digital detox once a year. Most recently, I did this while at a transformative ayahuasca retreat deep in the Peruvian jungle. The medicine was life-changing, and the break from my screens was essential.

31. Phones detract from your travel experience

When I first hit the road, at the tender age of 19, I didn’t have a phone. It was goddamn glorious.

Most travelers back then didn’t have phones and we all talked to each other. It was great.

These days, that’s changed a lot and a lot of travellers seem to spend more time documenting their travels than actually experiencing them. Hell, as a travel blogger, I’ve been guilty of this and that’s the reason I quit Snapchat.

I hated how my phone affected my travels and my mental health.

32. It’s good to get out of your comfort zone

I first hit the road because pretty much everything made me uncomfortable. I was shy and unsure of myself. Pushing myself out of my comfort zone helped me to face my demons and evolve into a more confident person.

33. Taxi drivers are the worst

I very rarely take taxis, preferring to hitch, drive myself, or when necessary, take an Uber. One time when I took a taxi I had a screwdriver pulled on me when I refused to hand over fifty euros for a twenty-minute journey. In fact, I would say more than HALF of the arguments and altercations I have had in my last fifteen years of travel have been with taxi drivers.

34. No pain, no gain.

To get to Jomalhari, the mother of all mountains in Bhutan, I had to trek for five days through almost constant hailstorms. Worth it? You bet your ass it was.

35. Spend money on food

When I was traveling on $10 a day, I used to spend almost all of that on food. It’s important to eat well on the road to keep your health up, especially if you’re roughing it.

36. Time is warped in some places

In Pakistan, “twenty minutes” could mean anything from two hours to two days.

37. Always be friendly

Enthusiasm and politeness can take you a long way in life. This guy’s got the right idea – check out that grin! 🙂

38. Beware foreign road rules

In Iran, they have speed cameras. I know this because I got caught by, not one, but TWO whilst tearing around Tehran at one hundred miles an hour.

39. Traveling teaches you how to problem solve

If you’re on a budget, you can’t buy your way out of problems. To be broke and on the road will teach you how to solve a real massive variety of problems.

40. You’ll learn how to assert yourself

On the road, you will learn how to stand up for yourself against touts and pushy salesmen.

41. You’ll improve your social skills

You meet so many people on the road that you can have never-ending ‘do-overs’. You can experiment with the kind of person you want to be and how you want to interact with people.

42. You’ll discover the power of networking

As you meet folks on your travels, and connect with people through social media, you’ll find your tribe of other travelers and aspiring entrepreneurs. Building connections can lead to new opportunities… Reach out to like-minded individuals, attend events (such as the Chiang Mai SEO Conference), and remember that everybody has something to teach…

43. You’ll learn how to haggle

Negotiating is a valuable skill and one that you can hone on the road.

44. Traveling can improve your job prospects

Employers are looking for people who can think on their feet and problem-solve. Crucially, employers are looking for people with life experience – travelling the world will give you a ton of that!

45. It’s important to use your free time wisely when travelling

I have three go-to outlets for free time: Push-ups (minimum of 100 a day), reading, and writing blog posts. If you don’t use your free time, you’ll end up bored (and probably a pothead). It’s smart to have a plan to use your free time to learn a skill, build an income or focus on your fitness or personal development (journal amigos!).

46. Embrace failure as a stepping stone

Traveling taught me that things don’t always work out how they should. This is a great lesson that you can apply to your side hustle… In the world of entrepreneurship, failure is inevitable.

47. There are many ways to support a life of travel long term

The internet provides you with TONS of ways to educate yourself and to earn an online income. Use your free time on the road to look into what interests you. If you want to travel forever, start working on a passive income stream. Setting up my travel blog has completely changed my life and allows me to travel full-time.

48. But it can be tough to work

It’s difficult to get a lot done in hostels, so if you really want to hustle you are going to need a base. Work hard and work efficiently and you can achieve anything.

49. Keeping a travel journal is the best way to record your trip

For me it’s partly this blog, I tend to write about whatever I want which is refreshing. I keep my most personal thoughts in my beautiful travel journal though and have a case full of them which (after my dogs) is the first thing I would grab in a fire.

50. Not every day on the road is amazing

Here’s the thing – travel has been glamorised to hell by influencers and it’s easy to be fooled into thinking that every day, every moment, is amazing.

It isn’t….

Diarrhoea lurks around every corner. (Pack electrolytes, they save the day.)

For reals though, although that is real advice, traveling the world, especially broke, is filled with epic highs and epic lows. Some moments suck.

51. Sometimes, you need to take a chill day

Things go wrong. Sometimes you need to take time to recenter yourself and rejuvenate from being on the move or working your butt off. I recommend hanging out in a hammock…

52. Always try to be kind

If everybody is kind, the world will be a better place.

53. There’s nothing like arriving somewhere new

I get a real buzz, an almost electrifying enthusiasm, about rocking up somewhere totally new. Who knows what’s gonna happen, who I’m gonna meet, what I’m gonna see, what I’m gonna eat? I love the uncertainties of a new adventure.

54. A routine is crucial to success…

Whether you are backpacking the world, starting a business or starting a business whilst on the road, morning routines are where it’s at! If the first act of the day is jumping right out of bed at the first alarm and getting on with something that makes you feel good and helps you grow (eg. exercise and a journaling sesh), then you’re already having a good day.

It doesn’t have to be mornings, but building habits – meaning you do it every day – cultivate a healthy mind and a productive flow. Cultivating the DISCIPLINE to stick to a routine is an incredibly important skill and one I learned whilst traveling.

55. Get more out of your adventures: do some research!

I love history. Before I rock up anywhere near, I always do a bit of digging to find out the history of the place I am travelling to. I also strongly recommend reading books about the countries you are travelling through; you’ll learn a ton and have a more meaningful experience.

56. Be grateful for what you have

Honestly, if you are reading this that means you have easy access to the internet and are probably American, European, Canadian, or Australian. We are so goddamn lucky, we have access to so many opportunities. Don’t moan about not being able to afford to travel because the truth is you can travel.

You just might not be as comfortable as you would like but do it anyway. Hit the road as a broke backpacker and learn how to make it work. It’s an awesome experience.

57. It’s tough to stay fit on the road

Personally, this is my least favourite part of travelling – struggling to keep my fitness in good condition! I always travel with a skipping rope and I do 100 pushups daily, but ultimately my fitness slips over time when I can’t regularly get into a Crossfit box.

58. You can have whatever you want… if you put in the work

The law of attraction is a powerful thing, visualise what you want, visualise who you want to be, and then work your butt off till you get there. With a smart strategy, consistent effort, and a little luck… anything is possible.

My dream was to open a kickass hostel for aspiring entrepreneurs and digital nomads, and in 2022 Tribal Bali finally opened its doors to our first guests…

59. Don’t be fooled by the ‘Instagram lifestyle’

I could write a whole post about this. There’s a huge amount of misinformation floating around the web about long-term travel. The truth is that many travel bloggers portray a style of travel that isn’t financially sustainable to most (they’re scoring all that fancy accommodation for free you know, not paying for it).

Use your gut when doing your research and remember – it’s all about the actual travel, the cultural immersion, and meeting cool people, not staying in glitzy resorts.

60. Beware FOMO

Fear of missing out is a bitch, don’t let it get to you.

61. Locals often know best (and Couchsurfing rocks!)

Some of the best experiences I’ve had whilst travelling have only been possible through local intel. I am a huge fan of Couchsurfing and have Couchsurfed all over the world; it’s an awesome way to meet local people and have amazing adventures.

In Jordan, I cavesurfed with a Rastafarian Bedouin for a few nights. These days, the Couchsurfing platform isn’t in good condition BUT it’s totally possible to find couches by posting on Instagram, Facebook groups, or asking friends (of friends) – especially if you’re visiting more ‘out there’ countries that are excited to get backpackers.

62. Thank fuck for buffs!

I never travel without a buff scarf. It can be used as a makeshift eye mask, as a filter to keep dust and pollution out of your mouth, as a cover to keep tattoos out of the sun, as a bandage and, in extreme situations, a makeshift condom (just kidding).

63. This planet is massive

The scale of this world, this galaxy, this universe and all of the unknown mysteries constantly boggles and excites me. Our world is an amazing place.

64. But it’s not invincible

Don’t contribute to the plastic problem. Please don’t trash this amazing world. Take your shit away with you when you’re finished camping, hiking or romping in the woods.

65. If you’re lost, stay calm

Retrace your steps, find a logical place to pause and collect your thoughts. Usually, somebody will come along after a while who can help you out. If you’re out in the middle of nowhere, know which direction you need to walk in and carry a compass or use the app on your phone.

66. Always try street food

It’s cheap, it’s fast, and it’s an authentic taste of the local culture.

67. You can form real connections with people from different countries

I have an adopted family in Pakistan, and I feel no weirdness using that term, I love these guys and think about them most days. I’ve visited them six times now and every time, I’ve grown closer, they are a remarkable group of people. It’s fair to say that mountain people, no matter the nation they hail from, are usually pretty amazing people – tough, kind, resilient and humorous.

68. It’s better to be decisive even if you make the wrong decision

Dithering rarely helps anything. Make a decision and roll with it, evolve your plans as you need but be decisive.

69. But in business, do stop to pause when making big decisions.

Get second opinions, apply some guide-rails, and be careful with BIG decisions. On my entrepreneurial journey, I’ve made some pretty serious fuck-ups, including effectively giving away a business I founded on my own and spent 6 years working on to somebody who I knew was dishonest.

When triggered, it’s real easy to make mistakes, so try to collect your thoughts first. Building a business, especially if you are successful, will pose unique challenges that require you to really stop and evaluate. If you DO just smash through decisions too fast, which is my style, it can bite you in the ass.

70. You’ll meet amazing people on the road with the craziest stories

I’ve shared beers and more with professional poker players, a stripper, a drug smuggler, a washed-up rock star, a Cryptocurrency founder, a Russian tycoon, a poet, an inventor, a Bollywood actress, a Kurdish freedom fighter, one of the internet’s founding fathers and many more amazing people.

Ask questions, find out the stories of those you are with, and learn.

71. Most people want the same things out of life

On the surface, it can seem like people from different cultures have nothing in common but in my experience, I have found that everybody has the same hopes, dreams and aspirations. People all around the world want to feel safe, want to feel loved and want to be noticed. People want to laugh, to build a good future for their children, and to work on their passion projects.

72. Always pack a good book

Stay off your phone and instead read a book – enjoy some good travel reads. 

73. I’m still scared of heights

No matter how many times I conquer this fear, I still get dizzy at heights. This bridge in Pakistan scares the shit out of me, but I’ve crossed it.

74. Find beauty in the little things

Every day, there will be at least one thing that is beautiful. Keep an eye out for it.

75. Try to avoid judging

Look, it’s a natural human tendency to judge both others and ourselves. Ultimately, this is often a waste of energy and the world would be a kinder, safer place for all if we did this less. Try to be kind, friends, and understand that everybody, and every culture, has swirling, complicated histories that make up their very being.

76. Create a healthy work-life-travel balance

Finding the balance between travel, self-care and working on your projects can be tough but it’s crucial you make the effort to maintain a balance… Take one step every day for all three of these; doing something to look after your mind, to grow your project and to get the most out of your travels.

Journal, brainstorm topic ideas for your next blog post, go for a walk and enjoy a sunset. Balance is key.

77. My favourite hostel hack

While I’m a fan of camping and Couchsurfing, every now and then a hostel is a better option. When booking a hostel, you can get a cheaper price by booking in advance (as many hostels use dynamic pricing AIs that puts prices up closer to the date of travel). This little hack saves thousands of dollars over the years, especially in more expensive regions of the world.

78. It’s the journey, not the destination (this is cliche as fuck, but it’s true)

This really sank in for me when I attempted my big overlanding journey to Papua New Guinea… My destination was the original purpose of the trip and it motivated me. It was on the horizon, it was something tangible.

I just had to keep going East.

Along the way, so much happened. I realised it was within the journey that the magic was happening.

79. Stay true to your passion and purpose

Remember the reasons why you started this journey; be clear on your values and what you want to achieve in the next year, three years, ten years. The road is filled with many distractions, frequently check in with yourself to ensure you are living into your values and using them as a guiding force when making decisions and setting goals.

80. Foster a growth mindset

Never stop learning and seeking new knowledge. Explore new cultures with an open mind, take the road less traveled, visit lesser-known places. Attend workshops, read books, listen to podcasts, and constantly challenge yourself to improve, learn and expand.

This is never easier than when you are on the road since…

81. Traveling long-term is the ultimate learning experience

It’s true. Get out there, be brave, get off your phone, journal, plot big goals, and take consistent steps to reach them.

82. Traveling long-term won’t solve all your problems, but it may help

Personally, traveling has saved my life more than once. Traveling the world has allowed me to put some deep-seated insecurities to rest, accept myself for who I am and to work through a lot of shit. There is a huge amount to be gained from exploring the world and yourself and being on the road gives you so many incredible opportunities to experiment, learn and evolve.

Peace out maaaaaan.

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