Without reading this first!

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

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.

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.

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 good, 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 as 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.

First, let me reiterate some of the apparent 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 kinds of serendipitous experiences.

Your health will probably improve unless you spend the entire time sampling cheese and wine in southern 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.

It isn’t cheap

I’m not sure how much it cost my wife and me to travel during the entire year 2014 (6 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).

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 costs.

Some may say that you could “travel hack” your way to low-cost travel, but this mindset was anathema to our 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 sizeable.

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.

You will freak out

Last week 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 on 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.

I then shared my reality. It took me eight months to completely disconnect and “unwind” from 14 years of intense work.

Why so long?

I have no idea!

During the first few weeks after quitting my job, I felt super relaxed, but I 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 sometimes 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 constantly questioned 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 returning 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 the level of stress and engagement you faced in your previous job. Having people around that understand and support your decision can also help.

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.

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 can 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 must 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.

Good friends are hard to find

You will meet many people when you travel, particularly if you travel solo. However, unless you decide to plant yourself for 3–6 months in specific places, the chances of making lifelong friends are unlikely.

In most cases, we moved spots every few days while traveling abroad except for the handful of times when we spent 1–2 weeks in particular places. It’s impossible to build high-quality and lasting friendships in that period.

I consider myself a very content person and am perfectly happy just being with myself. However, at some point, you will crave a 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 intended to keep in touch.

Travel can become a job

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

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. Setting up and breaking down “camp” (if you spent time road-tripping and camping). 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 but there is also something fabulous about having a consistent place to call home, running water and heat!

Not to mention…..sand gets into everything.

“Working” on a beach all day doesn’t really work so well!

Was it worth it?

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

Heck yes, it was worth it.

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 grips 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 experiences 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 to 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 leap, knowing that ever-present challenges are worth encountering and overcoming if the payoff is big enough.

For others who wish to quit their job on a whim, I hope this article will be a warning to not leave a good situation without giving it some serious thought. The grass may not be greener on the other side.