How hiring an assistant can help freelancers travel more

We could all probably use an assistant. But when you’re a freelancer running your own business, hiring an assistant can often be a practical way to increase both your revenue and quality of life (including your ability to travel more).

Let’s use a hypothetical freelancer, “Sally,” to illustrate this point. Sally is a freelance consultant who charges $80/hour for her services. She just started her business last year and spends roughly 10-15 hours per week on administrative tasks, like data entry, qualifying leads, and scheduling calls.

If Sally were able to take the 10-15 hours per week that she was spending on these non-revenue earning tasks and focus the time on working with clients and growing her business, she could increase her revenue by around $800-$1,200 per week. Assuming Sally pays $15/hour for an assistant (because Sally knows that everyone deserves a living wage), Sally would still be earning an additional $650-$975 per week.

Additionally (and, for purposes of this blog post, more importantly), hiring an assistant can help freelancers travel more. In addition to being able to take the increased revenue and use it for trips (both for business and fun), hiring an assistant makes it easier to work outside of your “home” base.

The reason for this is that even though the world is becoming increasingly digital, there are still reasons that freelancers may be tied to a specific location. In my own freelance business, a pain point I’ve faced is that I will sometimes need to get mail or mail documents out (yes, snail mail!), which can make it hard to plan trips that last more than a week or so. But by delegating these tasks, where possible, I’m able to extend my trips and worry less.

It’s often the case that if you’ve just started your freelance business, the last thing you want to think about is bringing on an assistant. Likely, you’re still trying to figure out if it’s a sustainable business and you want to keep every last penny of revenue that comes in (which is something I can totally relate to). Also, hiring an assistant sounds like something more “successful” people do.

But once you’ve established your business, and particularly if a goal of yours is to use your freelance business as a catalyst to travel more, it’s a step that’s definitely worth considering.

When you’re at the point where you’re ready to hire an assistant, there is great recruiting technology available to help make the process seamless.

Are you a freelancer who has used an assistant to help your travel more? Let me know in the comments!

Digital nomads: What to do if your parent is facing a terminal illness

I started this travel blog, in part, to counter the sad and depressing stories that were overwhelming my news feed. Because of that, I’ve been hesitant to write about some pretty intense stuff that I’ve been dealing with over the last year – mainly, my father being diagnosed with a terminal, aggressive form of cancer.

It’s, of course, never easy when a parent receives a diagnosis like this. And while a lot of your energy may go to helping your parent and other family members out, it’s also completely normal to be concerned about how a diagnosis like this could affect your work.

For digital nomads, there are unique concerns. For example, some digital nomads only plan on living that lifestyle temporarily before having a family and settling down, so even taking a year or two away from that could change their career trajectory and life experiences entirely.

Below is a list, based on my experience, of some tips that I hope will help fellow digital nomads who have a parent that is facing a terminal illness diagnosis:

1) Talk openly about it with your parents and family members

Because you are able to work from anywhere in the world, you may decide that it’s best to move back home to help take care of your parent. Alternatively, the freedom to work wherever you want may make you feel even more guilty about not returning home.

For those who want to continue traveling, the truth is that it’s unlikely that your parent would want you to stop living your life because of a diagnosis like this. It’s worthwhile to have an open, honest conversation with your parent about your plans, get their thoughts, and also discuss it with other family members who may be helping provide care for your parent. It’s also important to think about if you’d regret not spending the limited time with your parent.

Based on the conversations you have, and your own personal reflections, you can update your travel schedule accordingly.

2) Make the city your parent is based a travel hub

My father lived in Philadelphia, which is where I grew up and went to law school. Before my dad was diagnosed with cancer, my plan was to never visit Philly again. But with the diagnosis and my dad’s limited ability to travel, that plan went out the window.

One positive that came from flying to Philly often was being able to use it as a travel hub, particularly as it’s a big American hub and I had a significant number of miles to spend. As I’m based in San Francisco, traveling to Philly made Europe much more accessible, and there was even a direct flight to Budapest from there.

Despite all the bad stuff that was going on, I was able to go on some adventures that I otherwise would have missed thanks to using the city as a travel hub.

3) Set clear limits on when you’ll be working when you go back to visit

Some people assume that being a digital nomad is the same thing as being on a permanent vacation. But the reality is that digital nomads, particularly those with a side hustle, are often always working.

This presumption that digital nomads don’t really work can make visiting a parent more difficult. If you are freelancing, it’s important to explain to your parent that you don’t have paid time off, and that you need to ensure you’ll maintain a steady income. If you are an employee with PTO, it’s still okay to let your parent know that while you’re in town, there are days that you will be working and times that you won’t be available.

4) Book refundable tickets and hotel rooms

If the prognosis is bad, you may need the ability to change your travel plans on a whim. As a result, when looking into airfare and lodging, you may want to prioritize reservations that are fully refundable, or that can be changed for a small fee.

With the airfare, because refundable tickets can be quite expensive, the best thing to do is to book travel using miles, which can usually be redeposited into your account for a fee (ranging from $50-$200+).

For lodging, there are tons of hotels and Airbnb’s that have very reasonable cancellation policies.

5) Use points for business class flights to visit 

I hate, hate, hate spending points on domestic travel. For most airlines, the redemption value on domestic flights is very low, particularly compared to international awards. So, it goes without saying that I especially hate using my hard-earned points to book domestic business class flights.

That said, traveling home to visit a dying relative is very stressful on its own, so if you have enough points, it’s definitely worth considering using them to book business class flights home, to make the journey a bit less stressful.

8 places I would visit if I had paid time off

I realize that I am very lucky — getting to work remotely while traveling the world is, in my ways, a dream come true for me. But, as I frequently write about, this type of travel means that the destinations I visit need to have reliable WiFi and be in time zones which are conducive to working with American clients.

Because of this, I sometimes catch myself dreaming of the day that I can go completely off-the-grid on a trip. Below are some of the top destinations I’d like to visit if I ever got some paid time off.

Montenegro

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Located just south of Croatia is Montenegro, a gorgeous country bordering the Adriatic Sea.

I first decided that I needed to go to Montenegro while traveling down the Dalmatian Coast, from Split to Dubrovnik. As I kept heading further and further south, I could not believe that the landscape kept getting more and more beautiful. I took out a map (because maps were a thing back then), and saw that if I kept going south, I’d hit Montenegro, and set my goals on visiting the country.

While it is stunningly beautiful, WiFi is not yet reliable in the places I’d like to visit in Montenegro, which is why this trip has been put on hold. But hey, I’m told delayed gratification can be a good thing… right?

Patagonia

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It’s my own fault that I haven’t visited Patagonia yet — I’ve actually had 2 trips planned there that I’ve canceled at the last minute (the first time, I went to Mendoza, Argentina instead and the second time, after checking the forecast in Patagonia, I decided to instead visit the Atacama Desert in Chile).

I am still aching to go, however, particularly to Bariloche and Ushuaia in Argentina.

While WiFi in those destinations is actually decent, the types of activities that I want to do (hiking, camping, and some adventure sports) would be difficult while working remotely.

Guatemala 

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Guatemala, particularly Antigua, is increasingly being a hub for remote workers. Known for its stunning landscape, Mayan history, and low cost of living (for Americans), this Central American country has been a top dream destination of mine for years now.

Although there are spots where you can find reliable WiFi, I want to stay on Lake Atitlán, which was formed in a massive volcano crater and is supposed to be one of the most beautiful lakes in the world. WiFi is spotty in this area of the country, though, so my visit will have to wait!

Mongolia

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I love taking the road-less-traveled and there are few places that are more “remote” than Mongolia.

While the capital, Ulaanbaatar, has reliable infrastructure, my dream isn’t to stay in the city – it’s to go to the windswept plains and Gobi Desert and to get completely off-the-grid.

As a remote worker, this isn’t possible (at least not yet), meaning I’ll have to keep Mongolia on my bucket list for now.

Greenland

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There’s an old saying amongst seasoned travelers: “When you’ve seen the world, there’s always Greenland.”

Located at the tip of the world, I first decided I needed to travel here after taking in an amazing view of the country on a flight from Norway to California. Since then, I’ve used Instagram to follow a few individuals who live in Greenland and have been captivated by their pictures.

While WiFi is reliable in towns and certain villages, I would love to be out on a boat and on hikes, neither of which are conducive to remote work.

Maldives

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It’s not hard to see why this is a dream destination of mine – with crystal clear water, idyllic beaches, and some of the most luxurious accommodations in the world, the Maldives is one of the most aesthetically pleasing places on the planet.

The tourist infrastructure is set up for honeymooners rather than remote workers, though, and while many hotels have decent WiFi, it’s often in the public areas and the time zone can be difficult to work from with American clients.

With global warming and the chance that the islands will soon be under the sea, I’m definitely in a rush to visit (and hope that I can disconnect when I do).

Namibia 

Namibia

With the Atlantic Ocean to the west, Rwanda to the east, and the Namid desert in between, Namibia offers a mix of stunning landscape and incredible nature/wildlife.

While the country is starting to attract more and more visitors, WiFi is still fairly unreliable and the time zones are difficult to work from with American-based clients.

Bhutan 

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Nestled between India and China is Bhutan, a Buddhist kingdom on the Himalayas’ eastern edge.

Featuring jaw-dropping landscapes, temples built on the sides of mountains, and in a region known for its incredible food, Bhutan is a dream destination of mine. As an American, it can be difficult (and costly) to obtain a visa to travel here and the time zones/WiFi aren’t ideal for a remote worker.

Let me know what you think of this list in the comments below!

5 steps to take before visiting a new country

Whether you’re new to travel or a regular globetrotter, visiting a new country is always exciting. It can also be a bit nerve-wracking, particularly for solo travelers, as you may be worried about safety, maximizing your time while visiting, and making sure you have a good time.

Below are some tips for steps to take after you’ve booked your adventure but before you step foot in a new country:

no one deals like we do!

1. Learn basic phrases in the local language

Aside from my love of unlimited soda refills, probably the most American thing about me is that I am terrible at learning foreign language. After taking almost 8 years of Spanish and spending 4 years living less than 100 miles away from the Mexican border, my Spanish language skills are still very basic (though get better with alcohol consumption).

That said, before traveling to a new country, I always make sure that I learn how to say the basics, which include:

  • Hello
  • Thank you
  • Sorry/excuse me
  • Goodbye

While it would be great to know more (and see tip #4 here for help with that), I’ve found that knowing these words in a local language, a smile, and some body language are often all that I need to traverse a new, foreign destination.

2. Figure out currency conversion rates

One great way to save money when you travel is to use local ATM’s rather than currency exchanges to get your money, as the rate your bank charges is often lower. To do this, you should have an idea of how much money you need to get out by the time you land.

A trick that I like to use is looking up typical currency denominations and their corresponding value in USD, and writing down what it amounts to. For instance, in Colombia, here’s a list of the bills they have and current value in USD:

  • 5,000 Pesos = $1.75 USD
  • 10,000 Pesos = $3.50 USD
  • 20,000 Pesos = $7.00 USD
  • 50,000 Pesos = $17.50 USD

Knowing the exact worth, in USD, of these bills helps me avoid math (or really, getting the currency conversions wrong) when I’m out and about and possibly with no internet/cell service.

3. Learn about the local public transit system

If you’ve ever been to a new country and tried to hop on a local, non-tourist focused train/bus, you’ve probably experienced some anxiety related to it. Are you going the right way? Do you have enough money to cover the fair? Will there be signs for where you need to get off?

Even with proper research, a new city’s public transit system can be intimidating. I was in Tokyo a few months back for the annual cherry blossom festival, and Shinjuku station was hectic and confusing enough that, even with a plan, I almost had an anxiety attack.

But if you plan on using public transportation at all (and you should!), you should download a copy of the city’s local transit map and look into things like day passes, cost of public transit tickets, and hours of operation. Sometimes, you’ll find that private options (such as cabs or Uber) offer better value for your time and provide a way of saving time for you to explore.

4. Download “Google Translate” and “Google Trips” apps

Recently, I wrote an article about how Google Trips is my new favorite travel tool. I’ve linked to the article itself but, basically, it provides amazing day trip itineraries based on your interests.

Although Google Trips is my new favorite travel tool, Google Translate has been a favorite travel tool of mine for years. You can use Google Translate in a few ways, including entering a phrase you’d like to say in English and having the app tell you how to pronounce it in a local language to placing your phone over a menu (or anything in a foreign language) and having it auto-convert into English or another selected language.

5. Look into visa requirements

A few years ago, I was flying from Lima, Peru to Buenos Aires, Argentina when, at the Lima airport, I overheard 2 Americans talking. Apparently, they hadn’t realized that travel to Argentina required a visa for Americans, and because the system to apply for a new visa was down, they were stuck in Lima until they could get the visa approved.

Now, admittedly, I’m not the best at this — I’ve got a trip to Georgia planned in 7 weeks and I haven’t looked into the visa… yet. But you can save yourself a big headache by having the visa situation figured out a few weeks before your trip (or potentially a few months out for places that are known to have a difficult visa process, such as China).

Are there steps you take when you traveling to a new country? Let me know in the comments!

5 amazing places to work remotely from this fall

Call me old-fashioned, but I love a good shoulder season. Often, I’ll avoid international travel during the summer — and the high prices and temperatures associated with it — instead opting for amazing trips in the fall.

Since I’m working while on these trips, I’m concerned not just with the weather and cost, but also WiFi, safety, livability, and infrastructure.

If you can work remotely and are looking for some great destinations for the fall, be sure to consider these places:

Tbilisi, Georgia

Tbilisi

Tbilisi has almost everything you’d want in a remote work destination – it’s safe, cheap, has solid infrastructure/WiFi, and it gets major bonus points for being off-the-beaten-path (though Western tourism to Georgia is starting to pick up).

In September, Tbilisi experiences an average of 4 days of rain with an average high of  80°F/27°C and an average low of 59°F/15°C.

I’ll be spending the latter part of September here and can’t wait to report on it.

Seminyak, Bali

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There is never a bad time to go to Bali. Seminyak, located just north of party-central Kuta, boasts amazing beaches, a strong and growing remote work community, and is an easy drive to some of Bali’s most amazing attractions.

It’s cheap, too – if you do your research, you can rent out a private villa with your own pool that is only steps away from the beach for roughly $80/night (with even more affordable options if you’re willing to forgo a stunning villa).

In September, Seminyak experiences an average of 4 days of rain with an average temperature of 80°F/27°C.

Marrakesh, Morocco 

Marrakesh

Morocco is one of the most beautiful countries in the world and Marrakesh, nestled at the foot of the Atlas mountains, is no exception.

With amazing food, beautiful views, and incredible markets, fall is the perfect time to visit as the weather starts cooling down.

In September, Marrakesh experiences an average of 1 day of rain with an average high of 90°F/32°C and low of 66°F/19°C.

Santiago, Chile

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Anyone who reads my travel blog knows that I am obsessed with Santiago. It is, in my opinion, one of the safest, most beautiful, and livable cities on the planet.

Although it’s technically spring in the southern hemisphere, it’s still the perfect time to visit, with an average high of 67°F/19°C and 2 days of rain in September.

Budapest, Hungary

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Recently voted the second most beautiful city in the world, you seemingly can’t go wrong with Budapest — it’s cheap, photogenic, and has reliable WiFi with a good infrastructure. There have been some alarming political developments in Hungary over the past few months, but it’s still safe to visit and a haven for remote workers.

I’ll be spending a week here in September before heading to Tbilisi and, similarly, can’t wait to report on the trip.

In September, Budapest experiences an average of 5 days of rain with an average high of 73°F/23°C and low of 51°F/11°C.

Are you planning any fun remote work adventures this fall? Let me know in the comments!

8 reasons why Tulum is the perfect destination for remote workers

Beautiful beaches, reliable infrastructure, and a community of digital nomads — read on to discover why Tulum may be the perfect destination for remote workers.

1. Easy to get to

Tulum is located about 90-minutes away (by car, bus, or shared shuttle service) from Cancún International Airport. Flights to Cancún are easy to get, with direct service from most major American cities.

2. It’s safe

Mexico is going through a crime wave right now, and even typical tourist hot spots like Cabo, Mazatlan, and Puerto Vallarta have had incidents occur over the last few months and in recent weeks.

But the Yucatán Peninsula, including Tulum, Merida, and Cancún have largely been insulated from this wave of crime and violence.

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Having traveled to Mexico many, many, many times, I have never once felt unsafe in the country. That said, there is nowhere that I’ve felt more safe in Mexico than in Tulum.

3. Easy to get by on English

If remote workers needed to know the language of every country they traveled to, for many, their world would be quite small. While I encourage anyone traveling abroad to a country that speaks another language to learn basic greetings and words, it’s always nice to know if you can get by on your native tongue.

In Tulum, speaking only English isn’t an issue, with taxi drivers, hotels, and restaurants all accommodating Americans and English-speaking travelers from all over the world.

4. Reliable WiFi (unless you’re right on the beach)

I spent a week working remotely from Tulum and had no connectivity issues, except while I was sunbathing on the beach itself (and it probably was better to take a full-on break at that point).

The closer to “town” you get (which is about 2 miles west from the beach), the better the WiFi gets. To ensure you’ll have service while you work, I would recommend staying closer to central Tulum and taking a taxi to the beach, which costs about $5 per trip.

5. Simply stunning beaches

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Turquoise water, soft, white sand, and warm tropical sunshine help make Tulum’s beaches some of the best in the world.

While there, be sure to get a massage on the beach, where you can listen to the waves crash while your worries float away — and cheap-ish by American standards (~$40 for 60-minutes).

6. Community of remote workers/digital nomads/freelancers

Tulum is almost synonymous with digital nomads and remote workers. If you go to a coffee shop in Tulum in the morning or afternoon, you’ll see laptops and iPhones galore, with people typing away, (presumably) working.

If you want to get away from the beach or need to be in an office, Tulum even has a dedicated coworking space, Coworking Karma Tulum.

7. Cenotes

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One of the main attractions of staying in Tulum is visiting some of the nearby cenotes.

“Cenotes are natural swimming holes formed by the collapse of porous limestone bedrock, which has revealed a secret subterranean world of groundwater pools,” according to Lonely Planet.

“Most cave cenotes have fresh water that has been meticulously filtered by the earth, making them so clear and pure that you can see straight through to small fish frolicking in the plant life below.”

A number of cenotes surround Tulum, including Gran Cenote and Cenote Dos Ojas. You can snorkel, dive, or just check out the beautiful scenery away from the warm, Mexican sun.

8. Ruins (with a view)

I’ve saved the best for last — the famous Tulum Ruins.

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Tulum’s history goes back to at least the late in the thirteenth century, during what is known as the Mayan post-classic period. Tulum was built with a wall surrounding it, and while the reasons are still largely unknown (and may have been lost with the decline of the Mayan world), it’s thought that priests and nobility were hosted within these walls.

For the best experience, you should arrive shortly after opening before the crowds come. Once you experience the ruins themselves, be sure to head to the beach for a swim in the crystal-clear blue water, surrounded by history.

Setting up a yearly travel routine: A guide for remote workers

Whether you’re a freelancer or have a job that allows you to work remotely, depending on certain circumstances in your life (finances, family, health, etc.), you may be able to travel much more than your friends who work more “traditional” jobs.

I began working remotely in 2015, first for a company and then as a full-time freelancer. Though I am still constantly learning from my travels, I have found that I enjoy being based in a city and booking ~monthly travel, rather than being a full-time digital nomad. Having a base helps me establish better personal and business relationships and it allows me to focus more on my physical and mental health.

Regardless of if you’re a remote worker like me who prefers having a travel base or if you’re a digital nomad constantly on the run, you may benefit by establishing a yearly travel routine.

What is a yearly travel routine for remote workers?

Both to keep my finances in check and for business/health purposes, I try to limit my travel to around one trip each month (and yes, I know I am ridiculously lucky to have this ability). Assuming I’m able to accomplish this goal each year, this means I’m generally taking at least 12 trips each year.

Of those roughly dozen yearly trips, there are certain destinations that I will (almost for sure) visit. For me, they are:

  • Puerto Vallarta, Mexico
  • Medellín, Colombia
  • Scottsdale, Arizona
  • Los Angeles, California
  • Hawaii
  • New York City

I consider these destinations to be part of my “yearly travel routine,” which is basically a set of locations that I try to visit once each year.

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Puerto Vallarta, Mexico: one of my yearly travel destinations.

Why have a yearly travel routine?

Having a yearly travel routine is not right for everyone. If your singular goal is to see as much of the world as you can while you can, having a yearly travel routine could stifle your ambition.

But for many remote workers, setting up a yearly travel routine has a lot of benefits. Advantages to having a yearly travel routine include:

  • Having a base of friends/clients in the places you’re traveling to. As a remote worker who’s traveling, your days may often be spent on your computer, on calls, and away from society. After you get done working, you may be itching for human interaction, but may not want to put forth the effort to meet someone new. By traveling to the same locations each year, you’ll slowly get to know people, and can have built-in post-work and weekend plans.
  • Assurance that you’ll have working infrastructure. Before each trip I book, I do everything I can to make sure I’ll have the necessary tools (mostly, reliable WiFi) to work. But I’ve been unpleasantly surprised before, arriving at a location where the internet was subpar (or lacking completely). Two qualities my yearly travel destinations all have in common are great infrastructure and settings which are conducive to my remote practice.
  • Knowing how to navigate these locations. Something I love about travel is having new experiences. That said, there is something great about arriving in a city and already knowing where to find the things you need and like, like grocery stores and restaurants, and having a feel for the city’s public transportation system. This can reduce time spent trying to learn a city, can lower overall costs (like knowing where the cheapest place for a great, quick lunch is), and can reduce travel anxiety.
  • Knowing where to stay. One of my favorite parts of my yearly travel routine is that for each of these locations, I already have either set neighborhoods or locations that I like to stay in. Almost uniformly, I pick these places because I’ve stayed before, have had good experiences, they are conducive to remote work, and they reasonably priced. Trying to find lodging, especially for a remote work trip, can be stressful, so having set places to stay makes planning travel a lot easier.

How to choose your yearly travel routine destinations

Choosing your yearly travel routine destinations can be difficult. Below is a brief description of how I chose my destinations:

  • Puerto Vallarta, Mexico – Since I live in San Francisco, Puerto Vallarta is an easy (and often fairly inexpensive) flight away. My friends like to go once a year, and I’ve added myself onto their annual trip, usually around March/April. The weather is perfect around that time of the year and I can save costs by splitting my room/remote office with a friend who also works remotely.
  • Medellín, Colombia – Thanks to Copa’s direct-flight service from SFO to Panama City, South and Central America have become much easier to access from San Francisco. Medellín is a surprisingly easy flight, and it’s relatively inexpensive (for around ~$50/night, you can rent an apartment in one of the best parts of the city with an amazing view in a luxury building, and for ~$20-$30/night, you can still find some amazing deals). It’s also stunningly beautiful with a great freelance community.
  • Scottsdale, Arizona – Having gone to college in Arizona, I like heading back to Arizona at least once a year to see friends, and also to enjoy the weather and lying by the pool.
  • Los Angeles, California – Since I have many friends and clients located in the Los Angeles area, I usually need to go at least once a year for business or social purposes. But even if I didn’t need to go, I still would, as I love the weather, the hikes, and (for the most part) the people.
  • Hawaii – I don’t know if I’ll live in San Francisco or California my entire life, so I want to take as much advantage of being a 4-5 hour flight from Hawaii as I can. Also, having lived on Guam, I have a lot of friends that relocated to the islands, so I can often see them whenever visiting.
  • New York City – Growing up in New Jersey and having gone to law school in Philly, I have a lot of friends in New York City. In fact, my sister lives there and I also have clients in the region. While I am not generally a fan of the northeast, the people here make it worth a yearly visit.

As you can see, one of the main factors behind the locations I’ve selected is people. In making your list, you may want to base your yearly travel routine on seeing friends, clients, and family (especially those located in amazing places).

Scottsdale
Sunset from Scottsdale, Arizona

Another factor is reliable WiFi – every location listed above has an infrastructure that fully supports remote work. Similarly, each location above is located in a time zone that is conducive to my schedule. While I often take a few trips each year to time zones that are “difficult” to work from for me (such as Asia and Europe), my yearly travel routine is focused on destinations that I can work seamlessly from.

Something that’s also important in establishing your yearly travel routine is easy flights. Whenever possible, I like to fly direct, and with the exception of Medellín, I can get to each of these destinations directly from San Francisco.

Final tips for establishing your yearly travel routine

If you are a remote worker who is interested in establishing a yearly travel routine, I would recommend leaving room so that about half of your trips are to new (or rarely traveled to) destinations. Part of the fun of being a remote worker who can travel the world is seeing and experiencing new places. By visiting new destinations each year, you’ll be sure to expand your mind, you’ll likely have more interesting stories to tell, and you may even find new places to add to your yearly travel routine.

Are there places you try to visit every year? Let me know in the comments!