Photo by Ravi Raman.
Me, hiking 230 miles through the Sierra’s, along the John Muir Trail.

“Live, travel, adventure, bless, and don’t be sorry.”

— Jack Kerouac

What sounds like kittens and rainbows, will be buttressed by the glorious stories of others who followed the same path. I’m guilty of perpetuating the one-sided story of the merits of extended travel myself.

Imagine walking into your office, meeting with your boss and telling him that you have had a good ride, but it’s time to go. You are leaving a perfectly good job on your own terms, as I did a few years ago, to live intentionally and like a vagabond.

I even went so far as to give a talk last year, to about 400 people, about why you should quit your job to travel the world. My experience is based on spending well over a year traveling through 8 countries with my wife, living out of backpacks and in truly nomadic style. Our travels ended just over a year ago, but the memories are fresh.

This post is designed to be different. It’s way more enticing to tell people to “take the leap,” but few talk about the perils of doing so.

Let’s set the record straight

If you think quitting your job to travel the world is all goodness, this post might have you thinking twice.

For those of you who are aware of the challenges and decide to do it anyway, you’ll be more likely to come away from the experience a bigger person (…and I don’t mean that literally, you will probably be more physically fit!). Overcoming resistance makes you stronger, and dealing with and surmounting the downsides of quitting your job can do the same. Knowing the potential obstacles increases the likelihood of your success.

Photo by Ravi Raman.
Evening “puja” along the banks of the River Ganga near Rishikesh in northern India.

First, let me reiterate some of the obvious benefits of prolonged travel. No bosses. Constant variety. Meeting new people. Seeing the wonders of the world. Free time to do whatever you want whenever you want. If you travel in an unplanned fashion, not thinking much more than a few days or weeks ahead of time, you have a greater chance to enjoy all kind of serendipitous experiences.

Photo by Ravi Raman.
Tramping around New Zealand with Alison (my lovely and talented wife).

Your health will probably improve, unless you spend the entire time sampling cheese and wine in the south of France. Like me, you might even rediscover your fitness (I lost 40 pounds in 18 months of travel without dieting or “working out”).

This is one side of the balance sheet. Next, let’s face some of the harsh realities of quitting your job to travel the world.

1. It isn’t cheap

I’m not sure how much it cost my wife and I to travel during the entire year of 2014 (six months internationally and then another six months throughout the USA). However, I would estimate that it was around $60K. I traveled a bit during 2013 and 2015 as well, but that estimate is just for the year 2014.

You might think it absurd to spend this much money on a year of travel for two people. No doubt we could have traveled for less, but we were pursuing a once-in-a-lifetime opportunity to do something great, and optimizing for the experience (instead of cost) was the priority.

There were several stretches of travel where we lived like kings on $20 a day (Thailand) and others where we were price gouged (island hopping the Fijian Mamanuka and Yasawa islands, staying at the overpriced resorts along the way).

Photo by Ravi Raman.
Partaking in a “Kava” ceremony in Fiji.

We also roughed it for over 80 days during our trip, making our camp-van tour of New Zealand more affordable and “freedom camping” in Southern Utah practically a free experience (and quite enjoyable, as long as you are OK pooping in a hole in the ground). Airline tickets were another significant factor in driving up our cost.

Photo by Ravi Raman.
Volunteering at a street dog and elephant rescue sanctuary in Thailand.

Some may say that you could “travel hack” your way to low-cost travel, but this mindset was anathema to our personal values. We didn’t want to game credit cards just for points. We also weren’t spending a lot using our credit cards, so accumulating miles that way wouldn’t work for us. Besides, I’ve never seen a genuinely wealthy and happy person “travel hack” their way to bliss, so we didn’t pursue that strategy. Even without airline tickets, the rest of the travel costs would have remained and been sizable.

Then there were other significant expenses, like boarding our dogs while abroad (we found an epic doggy retreat and caretaker to watch Duke and Spike for six months), joining a two-week guided tour of Rajasthan in northern India and preparing our house as a rental while we were traveling (a bunch of unplanned repairs were needed).

If you want to travel the world on your terms, be ready for a major hit to your wallet unless you plan to spend most of the time living in a hostel and eating beans and rice in a developing country.

Lesson: Save up more money than you think you will need to travel. Also, budget time and money to re-enter society when you are done. The last thing you want is the stress of money issues to ruin your travel experience!

2. You will freak out

Recently I met with a friend, a successful corporate executive at a leading tech company, who is contemplating a break from his high-pressure career. He was in the midst of a week-long staycation (spending a vacation at home) to rest and recharge. He mentioned how much more relaxed he felt with a week off work.

Photo by Ravi Raman.
We visited “The Shire” while touring around New Zeland in a camper-van. Bilbo wasn’t home.

I then shared my own stark reality. It took me eight months to completely disconnect and “unwind” from 14 years of intense work. Why so much time?

I have no idea.

During the first few weeks after quitting my job, I felt super relaxed, but also had the nagging feeling of regret at having perhaps made the wrong decision. I left behind a ton of money in stock when I quit (enough to pay cash for a luxury home anywhere in the country). I also had my peers (and family), to deal with. The people who knew me best could not understand my preference and at times blatantly questioned my decision.

A familiar refrain when I spoke with my family was, “Do you think Microsoft will take you back?” This was the last thing I needed to hear after finally building up the courage to leave.

While I thought I was relaxed, my brain was still constantly questioning my decision to leave a perfectly great job. It was a subtle sort of nagging, always there in the background like an itch I couldn’t scratch.

It wasn’t until we were wrapping up our international travel and on our way back to the USA for some extended road-tripping that I shifted into a whole new mindset. I was finally at peace with my decision and able to actually enjoy my experience of unplanned travel.

You might be different from me, but be prepared to have a freak-out moment (or a series of them!) if you quit a job. I surmise that the level of freak-out will be proportional to your tenure and level of stress in your previous job. Having people around that understand and support your decision can also help.

Lesson: Travel with an open mind. Don’t be rigid with your expectations for what you will do when you are done. Think and journal regularly, and allow the right “next step” for your life to emerge over time!


3. Everyone else will be busy

When you quit your job and start traveling, you will notice that everyone else is stuck in whatever work situation they are in.

Photo by Ravi Raman.
Road-tripping the USA with our dogs. Here we were in the Salt Flats in northern Utah.

If you parachute into town and expect friends and family to be ready and willing to “hang out,” think again. They have their individual lives to deal with. It’s not their fault. In today’s world, the traveler is an oddball.

Perhaps, like me, you will be able to rendezvous serendipitously with friends and family in various travel spots (as we did in New Zealand, Tasmania, India, Singapore and throughout the USA). However, most of the time you will need to make new friends or just enjoy doing things yourself.

The rest of the world operates on a different schedule than that of a professional traveler.

Lesson: Be comfortable spending time with yourself. Enjoy the peace and quiet, and use your independent adventures as a chance to recharge, learn and enjoy a break from your normal routine.


4. Good friends will be hard to find

You will meet a lot of people when you travel, particularly if you travel solo. However, unless you decide to plant yourself for three to six months in specific places, the chances of making lifelong friends is unlikely.

Photo by Ravi Raman.
Paddle-boarding off the coast of an island in Fiji. We sailed to Fiji from New Zealand with friends. However, most of our 18 months of travel was done independently.

In most cases, we moved spots every few days while traveling abroad except for the handful of times when we spent one to two weeks in particular places. It’s impossible to build high quality and lasting friendships in that span of time.

I consider myself a very content person and am perfectly happy just being with myself. However, at some point, you will crave connection to friends. Someone to share your adventures with. Someone to join you on trips and expeditions. Someone else to talk to aside from your partner or dogs!

We met dozens of people during our travels, but none turned into lasting friendships, even though we always traded contact info and had the intention to keep in touch.

Lesson: Get used to approaching people and saying hello. Everyone has a story to share. Be interested in what other people are up to and you’ll be more likely to make friends and feel connected to others despite being far from home.


5. Travel will become a job

Do you consider relaxing on a beach without any work for weeks on end a dream lifestyle?

Photo by Ravi Raman.
This parrot greeted us as the top of a mountain in New Zealand, called “Avalanche Peak”.

It is.

However, not all dreams last forever. Sand, the sun and the waves get old if that is all you are exposed to.

The tiny things extended travel require also wear on you over time. Figuring out how to get from here to there. Sorting out lodging reservations with spotty wi-fi and no cell phone coverage. Booking flights on crappy internet cafe computers with sticky keys. Regularly packing and unpacking your backpacks, camper and/or car. Dealing with no hot water, A/C or heat for months on end and in variable weather conditions (especially hard if you are camping long-term). Planning your day to ensure you have a chance to charge your electronics. Needing to say no to family and friend related obligations where traveling (“Sorry, I can’t make so-and-so’s wedding! Hope we can still be friends…”).

I could go on and on….

At some point, even travel can become a job. It’s great fun at times, but there is also something great about having a consistent place to call home, running water and heat!

Not to mention… sand gets everywhere.

Lesson: Spend more time in fewer places. Instead of traveling every few days, spend weeks (or months) at a time in each location to get to know the locals and immerse yourself in the regional culture.


Was it worth it?

Despite the downsides, was it worth it to quit our jobs to travel the world?

Heck yes, it was worth it.

Photo by Ravi Raman.
Saying hello to this fellow in “camel country”, in Pushkar, Rajasthan in Northern India.

It was worth every little frustration to travel the world with my wife for almost a year and a half in total. I highly recommend it for anyone who feels the travel bug pulling them, and also comes to grip with the realities of the challenges that will come up as they set out on their journey.

If you are like me, you will find that extended travel, like life, is full of its highs and lows. I find this variety of experience rewarding and more conducive to personal growth than sitting still. It’s not all sunshine and rainbows, but to me, that’s the point.

Perhaps, most importantly, you will find that extended travel will help you notice the “bubbles” you might be living in, gain the power of an outsider’s perspective on your life and give you the courage press the “reboot button” to see if things run better as a result.

My wife and I did just that, and things are working out fine now that we are settled back down in the USA (though we chose to live in a new place when we returned home).

For those of you who have traveled extensively, I would love to hear your comments on what was challenging about it, and the net effect of your experience. By sharing the good, bad and ugly, I hope we can inspire others to take the leap, knowing that challenges which are ever-present are worth encountering and overcoming if the payoff is big enough.

For others, the result I hope is different. If you are wishing to quit your job on a whim, I hope this article will be a warning to not do so without giving it some serious thought, the grass may not be greener on the other side.


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