24 Things I Learned from Taking a Two Month Global Sabbatical

By Sean Ogle •  Updated: 11/09/17 •  19 min read

Well, I’m back.

After 2 months, 6 countries, 10 flights, 22 beds, 26 cocktail bars, and over 4,000 km driven – last week I returned from an epic two month trip around the world with my wife.24 Things I Learned from Taking a Two Month Global Sabbatical

She was in the fortunate position of being able to take an extended sabbatical to celebrate 10 years at her company, so what’d we do?

We took a bucket list trip and started doing so many of the things we always talked about.

To be honest I wasn’t sure exactly what to expect before we left.

We didn’t have much more than a rough outline of a plan, and I fully intended to work more or less full time during the trip.

It didn’t take long to realize the way I thought this trip was going to go, simply wasn’t a reality and I’d have to adjust my thinking.

In this post, I’m going to share with you everything I learned from our two month trip. This includes things about specific locations, long term travel, running a business, and relationships.

My hope is regardless of whether you’re planning a trip soon, you’ll find this interesting, get a few ideas, and maybe learn something about yourself as well.

And if not? Well, then at least enjoy some pretty photos.

Travel and Destinations

1) Slovenia is poised to become the next must-see travel destination. Go soon.

Slovenia was the biggest surprise of the trip. Our three days in Ljubliana were highlighted by excellent food, the best gin and tonics of the trip, spelunking in massive caves, and experiencing what felt like a beautiful European city minus the tourists you usually see.

Lake Bled in Northern Slovenia

Lake Bled in Northern Slovenia

Lake Bled was even more spectacular. The 3.5 mile walk around the lake was gorgeous, and we stumbled into a random restaurant that was the very best meal of the trip.

This truffle soup? $6!

And the award for best meal of 2017 goes to? Sova in Bled, Slovenia. This was my starter soup with truffle, prosciutto, and Parmesan and it was hands down the best soup I’ve ever had. Not to mention it was only 6 bucks. The risotto main? Equally as impressive. Must visit if in the area. Hat tip to @almost_grownups on the choice!

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While we didn’t get to spend as much time there as we would have liked, I’ll follow the lead of so many friends who convinced me to go, and simply say: go to Slovenia. You won’t regret it.

2) Venice is horrible – until you get out of the touristy section.

I’d been to Venice once before, about 10 years ago. And it wasn’t nearly the romantic, relaxing destination that the world has portrayed it. Or perhaps I just wasn’t rich enough to experience it the way it was meant to be seen (talk about expensive!).

So I was eager to go back.

And unfortunately, for the most part, it was much like I remember it.

The Rialto Bridge is hands down the most chaotic tourist destination I’ve ever been to. It was insane, frustrating, and claustrophobic.

St. Marks Square wasn’t a whole lot better.

St. Marks Square in Venice, Italy

Tate in St. Marks Square.

Luckily our opinions of Venice were spared as we got lost winding through narrow streets in search of a cocktail bar. During that walk, we experienced a different side of Venice that was less chaotic, much more charming, and quite simply made every corner you turned an intriguing adventure.

Sabbatical 12

An alleyway in Venice.

Sabbatical 13

Il Mercantile, a fantastic cocktail bar in Venice.

3) New York is my favorite city in the world

After spending two weeks in NYC, I can safely say it’s my favorite city in the world. There’s almost nothing you can’t do there. It’s home to some of the best food and drinks on the planet.

New York at Night

New York at Night

It’s the very best golf city in the United States.

There’s history, culture, sports – no matter what your hobby or interest is, New York has something for you.

It’s just expensive. Really expensive.

Grand Banks

Grand Banks is an old schooner turned into a bar and restaurant.

4) Hong Kong isn’t far behind it

This sabbatical started out with an argument between Tate and me over which city is better. NYC or Hong Kong. I said the former, she said the latter.

So our original plan was to spend a month in both places and get a sense of what they’d be like to live there.

Then we realized a month isn’t quite enough time to get that experience, and it would simply turn into a much more expensive location.

My point in telling you this?

I won’t say she was right, but Hong Kong truly is a world class city. Similar to NYC, it has something for everyone, and every time I’m there I’m reminded of how much I enjoy it.

Also if you ever go? Do the Twin Peaks hike to Stanley Market. It’ll kick your ass, but treat you to some spectacular views. Here are some more fantastic Hong Kong hikes if you’re ever in the area.

Looking back at Central Hong Kong from the start of Twin Peaks hike.

Looking back at Central Hong Kong from the start of Twin Peaks hike.

5) You should go to Oktoberfest – but once will probably be enough

Oktoberfest in Munich has been on my bucket list since the day this site went live. It just seemed like one of those things you have to do once in your life.

And you know what?

I’d agree.

You have to do it once in your life.

The dirndls and lederhosen. The giant pint sized beer. The whole chickens. The rides. The tents. The chaos. The tourists.

Oktoberfest Munich

One of the many tents at Oktoberfest in Munich.

It’s all a site to be seen and I had a blast during the two days we attended it.

If I find myself nearby again, I’ll most certainly go – but there are plenty of other fun places to drink beer in giant crowds across the world that are worth exploring.

6) Skip the cities, tour the mountains and lakes of Italy

We enjoyed our time in both Florence and Milan, but by far the more interesting aspects of our time in Italy were the lakeside towns, mountain retreats, and Tuscan Vineyards.

The Dolomites are unlike any mountain range I’ve seen. They’re jagged, dramatic, and full of opportunities to explore.

The view of the Dolomites in Sexten, Italy

The view from our room in Sexten, Italy. Bet you’ve never even heard of it have you?

Rather than driving all the way to Lake Como, we toured Lago di Garda, which I’ve been told provides a very similar experience. Sirmione was one of the biggest surprises of the trip, and I’d recommend anyone go visit.

Sirmione: The coolest Italian town you've never heard of.

Sirmione: The coolest Italian town you’ve never heard of.

And the random explorations through vineyards and medieval towns in Tuscany was a last minute decision and one we’re totally glad we made.

Sunset from our B&B outside Buonconvento, Italy

Sunset from our B&B outside Buonconvento, Italy

Don’t get me wrong the big cities in Italy are great, but if you want to do something a little more unique – get out of town.

General Lessons on Travel

7) Not all tours are bad

For some reason, I’ve always had this thought in my head that tours are for old people or people who aren’t adventurous.

While you probably won’t find me on a Rick Steeves bus tour any time soon – there were a few instances on this trip when taking day tours completely enhanced our enjoyment of a location.

Most notably, we took an UnTour Food Tour in Shanghai. It allowed us to experience a number of local spots we never would have found otherwise, and experience some of the best Chinese food I’d ever had.

Same goes for our experience hiring a tour guide to take us to the Wolong Panda Reserve 3 hours outside Chengdu.

I mean, it led to this:

Tate at the Wolong Panda Reserve outide Chendu, China

Tate at the Wolong Panda Reserve outside Chendu, China

So it couldn’t be all bad, right?

8) It’s the highs and the lows that create stories – not the middle ground

I’ve learned that when most people travel, they search for the middle ground. The Holiday Inn Express, the $75/night hotel that is clean, comfortable, but at the end of the day – entirely forgettable.

It’s on either end of that where you have the stories.

We slept in dorm beds in a hut on a mountain in the Dolomites:

We also slept in a mold ridden hotel in Wolong China with no heat or hot water.

I wouldn’t describe either of those experiences as plush, or even comfortable – but both resulted in an incredible story.

Alternatively, for our last stop we stepped it up with stays at The Banyan Tree on the Bund in Shanghai:

Banyan Tree Shanghai

And this wasn’t even the good view from our room at the Banyan Tree.

And the St. Regis:

St Regis Bathroom Shanghai

The view from our bathroom at the St. Regis. Doesn’t suck, does it?

Two of the nicest hotels I’ve ever stayed in, they resulted in a few fantastic stories of their own.

Go high and pay for it by going low as well – both will be more memorable than that Holiday Inn.

9) If you live in the US, and have good credit, there’s no reason not to travel hack

Here’s the good news. The high ends stuff I just mentioned? You don’t have to pay for it.

If you live in the US and have good credit, there is zero reason not to travel hack.

We took first class flights, stayed in five star hotels, and also supplemented some of the other random expensive nights on the trip solely using Chase Ultimate Rewards.

I haven’t spent anything I would have otherwise. I’ve just made sure I get rewarded for the money I do spend – and doing that at the very least eased the burden of our travel expenses, and at best gave us some world class experiences.

I mean, remember this? You don’t really think I paid for it, do you??

10) Renting a car may be a better option than trains in Europe

If you haven’t spent much time traveling in Europe, let me let you in on a little secret.

Trains are expensive. 

Sure they’re incredibly convenient and usually quite comfortable if you’re touring cities – but as soon as you want to venture out to someplace a bit more remote – things get more difficult.

We rented a Ford Kuga for 3 weeks for a grand total of $411.


Our Ford Kuga!

The car had every feature we could have wanted, the drive on the right side of the road, and the added flexibility took us to places we never would have made it to otherwise.

11) When you travel? Have a “thing”

If I had to give one piece of travel advice, this would be it: Have a thing.

It’s great to show up in a city and see all of the main tourist attractions, but if you want to see another side of a city, have a consistent thread.

For me, it’s cocktail bars and golf courses.

For this trip, we focused more on the former. I’ve now been to 31 of the Top 100 bars in the world.

Speak Low Shanghai

Speak Low (#10 in the World) is one of my new all time favorites. This drink was called the Flirtibird and was just as elaborate as it looks.

With each city we went to, we ended up neighborhoods we otherwise wouldn’t have, experienced flavors you won’t experience anywhere else, and had a frame of reference we could draw comparisons to.

It made the trip and cities more fulfilling and gives us something we can do in any city we travel to in the future.

12) The more diversity, the better

While having common threads will help improve your overall experience, it’s also important to have diversity. If all you did was cocktail bars, museums, or say golf courses – you’re missing out on a lot of the joys of this kind of travel.

We spent time in giant cities. We traveled to some incredibly remote places in Italy and China. We did big hikes and spent time at the spa. We ate world class meals and had indulged in fantastic street food. We saw world famous sites, and other places no one has ever heard of.

More often than not, it’s not the famous tourist attractions that will be the highlight of your trip. So make an effort to add a little diversity, and experience things most people wouldn’t make the effort to do.

Want to take a sabbatical of your own? Check our 6 part course on starting a lifestyle business

13) Being uncomfortable makes you appreciate the comfortable

We had at least a handful of nights that were downright uncomfortable. We saw a different way of life at times that not many people in the US get to experience.

Experiencing that from time to time is an important reminder of just how comfortable our lives are. If you’re reading this, you most likely have privileges many other people don’t in life.

We all have struggles and tough times, but traveling to places off the tourist map can be a great reminder to keep you from taking what you do have for granted.

14) “It isn’t about how much you see, it’s about the quality of the experiences you do have”

We had just checked into our B&B in Tuscany and were talking to the owner about where we could go that afternoon, before returning to her villa to watch the sunset.

She laid out three wonderful towns that she highly recommended. But when we said we were going to try and do that and then make it back for sunset, she said “oh, then you won’t have enough time to do that without rushing it. Go to this other small town instead. “Remember it isn’t about how much you see, it’s about the experiences you have in the places you do see.”

I thought that was a really important lesson. All too often when we travel we try to tick off as many boxes as possible. Don’t get me wrong I obviously have a thing for lists, but it’s almost always better to truly enjoy fewer places, than rush through more.

15) Understand where you fall on the line of “Planning” vs. “Adventure”

Most of our friends thought we were crazy.

When we left we had none of our other flights booked. No other hotels booked. We hadn’t even sorted out our Chinese visa yet.

The idea of an adventure where we had the freedom to go wherever we wanted at any time, sounded so freeing.

And to a point, it was.

We ended up in some places we never would have gone to otherwise:


Working in the Italian mountain town of Canazei

But about 3 weeks into the trip, that began to take its toll. The stress of figuring out where to go tomorrow started getting in the way of what we were doing today.

If I were doing it over, I’d plan more. At the very least, I’d have a few more key hotels booked along the way, to ease the stress of trying to find the perfect spot at the last minute.

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Lessons About Working from the Road

16) Wifi connectivity hasn’t come as far as I thought it had

I was shocked at just how difficult it was to find reliable wifi on this trip.

All through Europe (and obviously in China) wifi was a constant struggle. Hotels would advertise it, and there’d be no connectivity. Restaurants wouldn’t have it all together. It’d work, but be slow as molasses.

Internet was far more of a challenge than I ever expected and is something that could have been mitigated with a little more planning on my end.

17) Also, T-Mobile’s global plan is a blessing and a curse

In the US, you can get an unlimited data plan on T-Mobile, that includes unlimited global roaming almost anywhere in the world.

So for under $100 a month, I could use my phone anywhere on the trip.

This was great, in theory. What I found was the speeds were so slow throughout the trip, that it caused more frustration than convenience. It could have been my older iPhone 6 not pulling its weight, but it was slow enough it made my hope of constant Instagram stories more difficult.

18) Chances are, if you take extended time away as a solopreneur, your business will regress

As I mentioned, the goal was never for this trip to turn into a sabbatical for me. 

But it kind of did.

Having Liz around to help with our content calendar, email support, and numerous other things was a godsend.

But the fact remains, without the daily attention that I usually put into the business I noticed things shift. Traffic was down. Opt-ins were down. Sales were a little down as well.

That’s ok. The reason I have this type of business is so I can have these types of experiences. But if you’re ever planning to take time away, be prepared to see a little bit of a hit until you’re back in the saddle.

19) If you truly want to grow a business, focus on just ONE

There’s a common thread among all of my most successful friends:

They have one brand. One business. 100% focus on it.

While I love being able to do Location Rebel, Breaking Eighty and a few other marketing consulting gigs in the golf world – it isn’t without sacrifices.

When you’re not devoting 100% of your time and focus on one thing it’s hard to see that live up to it’s potential.

This was amplified on this trip when I was working on a poorly timed launch for one of my golf clients. It kept me from spending my free time working on my business – and was definitely a bit of an eye opener.

While the way I’ve gone about things certainly has plenty of benefits, I’d encourage someone just starting out to focus on that one thing for as long as possible before you throw anything else in the mix.

20) A “lifestyle business” really is part of the lifestyle

A lot of people think a lifestyle business is just about making passive income so you can go do whatever else you want in life.

This trip reaffirmed the fact that this isn’t the case.

I truly love working on Location Rebel and Breaking Eighty. They are engrained in my lifestyle in a big way, and while I was on sabbatical I truly missed working on them.

Absence makes the heart grow fonder.

Lessons on Relationships

21) Travel is different for everyone. 

When you travel everyone has different goals, priorities, and ideas of what a trip should be.

Ryan wanted to hike. Tate wanted to go to museums and shop. I wanted to work more.

Everyone I was on the road with had slightly different ideas of what their time on the road should be.

This is totally ok, but when you’re traveling with someone else remember this is the case. Compromise is almost always the best approach – even if it means spending time doing something you might not have otherwise.

22) Be humble

It’s never easy to get constructive criticism about yourself and your personality. But while on this trip I had someone I trust and respect tell me they thought I’d started acting like “my way was the best way,” and that I wasn’t doing a good job of recognizing that other people choose to live their lives differently.

Man, this was tough to hear, but totally right.

While I’m very privileged to do what I do, and I think a lifestyle business can be a great fit for a lot of people – it isn’t right for everyone. I’ve always prided myself on believing that anyone can do anything they want as long as they’re happy.

Apparently, this hasn’t always come through and I’d gotten a little too preachy about this type of lifestyle.

It’s a good reminder that embracing humility and being humble will get you much farther in life than preaching and ego driven talk.

23) Most people don’t want you to work

I mentioned it just a minute ago, everyone has different goals when they travel – and for most normal people, this does not include work.

Learn how to embrace that for both your own sanity and that of your travel companions.

How to Get Work Done While Traveling (When No One Else Is)

24) The people make it worth it

Places are great. Experiences are great. So are attractions.

But almost always, it’s the people you’re with that make the experience so memorable. So whether it was the amazing time I got to spend with Tate or the friends we saw in different cities all over the world – punctuate your travel with people rather more than places, and good things will almost always come from it.

In the End…

Taking this trip and sabbatical is one of the best things I could have done at this stage in my life.

It reaffirmed my devotion and excitement for my businesses…

It allowed me to create memories that will last a lifetime with my wife…

It gave me perspective in seeing many different walks of life…

And given the opportunity, it’s something I’d do over again at the drop of a hat.

Have you ever considered taking an extended trip or sabbatical? What would it look like for you? All work? All play? I’d love to hear different ideas for how others have considered approaching this. Because after all, there’s no one size fits all to long term travel.

Want a sabbatical of your own? Let me help.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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6 comments on "24 Things I Learned from Taking a Two Month Global Sabbatical"

  1. Garin Etch says:

    Thanks for sharing! Love the pics, and I love the idea of having “your thing.” The McMenamins passport has made me fall in love with McMenamins. Maybe I need a global version!

  2. Renee says:

    I couldn’t stop laughing during your video, especially at the end when you were sad. The pouting was hilarious 😆 . 🙂
    It is so true about the highs and lows of a trip often being some of the best parts and the most memorable. I often tell people that those things give you the best story/comedy material even when it was a nightmare. (Read: cockroaches in your Airbnb etc.) Ahh.. the memories! You’ll talk about those experiences for many years to come.

  3. Jub says:

    Awesome write up Sean, reconfirmed a few things for me.

    1. I think you’d not have enjoyed Slovenia if you were there a couple months ago…plenty if people said it’s ‘too touristy’, you guys chose the best time for Europe. I couldn’t believe the dropoff in people as soon as mid-September came about!

    4. Will have to believe you. didn’t realise NY was so golf friendly! Will visit one day.

    11. ‘Have a thing’…love this idea. My thing is anything sports related in a city. I’ll skip the museum, but happily head to a random game of footy. EVen came to Antalya to volunteer at the Turkish Airlines Open last week.

    23. Most people don’t want you to work. Yessss, this is so awkward. I’ve sacrificed so much ‘work’ time, especially the first few months of this year to travel with someone special..that meant no income for a while, totally worth it. She was ‘ok’ with me working, but only did so when she was sleeping.

  4. Rob Deemer says:

    Hi Sean,

    Welcome back to the US!

    Great post! You talk about many places that my wife and I have in our bucket list, too. Thanks for the tips.

    Over the course of 5 summers, from 2009 – 2014, the travel goal for my family of 6 (wife, 4 boys, me) was to drive to see the continental US by car. I broke the trip down into 2 week vacations each summer to visit one region of the country at a time. Awesome experience. Our last state turned out to be Colorado, where we truly did experience a Rocky Mountain High (John Denver’s marijuana)!

    When planning the trips, we did much like you said that you and your wife did, taking the highs and the lows, but savoring the experience. Mine were much more structured than yours, but like you said in your post, ‘too each his own’. We saw all of the states, deeply experienced 24 National Parks, had great food, had awful food, saw much of the best and some of the worst that America has to offer.

    My boys, who are now in high school and college, have great memories of those trips, and an appetite for travel and adventure… good travel goals for their families later down the line.

    I did try to work, but that was limited, as WiFi is non-existant in most Nat’l Parks. The time away was worth it, though, and looking back would not change a thing!

  5. Rich says:

    Great post.
    Somewhat related… My wife and I are 6 months into a mini-retirement. We sold off virtually all our possessions, packed what remained in our car and vacated our rental in Auckland. We are now travelling around New Zealand’s South Island one house sit at a time. Partly to explore and partly to decide where to settle next (originally from the UK, we emigrated to NZ 6 years ago and now want to move out of Auckland). I’m a freelance web developer, whilst my wife is deciding what to focus on next (ex NICU nurse). To date we have traveled thousands of kilometers, house sit for 8 different couples, stayed in some amazing places and learnt some new skills. We don’t plan to stop for at least another 6 months.

    A few things we have learnt so far;

    1) have a list of things you want to do when you retire, don’t just stop. My list is never ending and I had strong ideas about how I would spend my time; but my wife’s was very vague and she has struggled at times without having a focus.

    2) You will still have days where you are blue; particularly if you already have your own black dog lurking somewhere. Just because you are “retired” and “living the dream” does not mean you are immune.

    3) If you want to get stuff done it can help to keep to a routine. This can be as a simple as getting up at the same time most days

    4) It’s possible to feel lonely at times. We spend weeks at a time looking after a house in an area where we know nobody. The handover aside, it’s easy to not interact with anyone meaningfully. Make the effort to find events and meet people. The human contact helps.

  6. Great stuff here Sean.

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