How Do I Convince My Employer To Let Me Work Remotely?

Remote work relies very heavily on trust and communication. I’ve just returned to a remote-first culture, so while there was never a need to sell the idea, there is still the ongoing need to ensure that I maintain the trust and open communication. Remember that, even in a job setting, you are in community with others.

If you’ve demonstrated the ability to deliver without issue, you will probably have an easier time convincing an employer. If they still are resisting the idea, perhaps working into it slowly could help ease any fears about the change in your physical presence.

Do a trial run domestically, if you haven’t already, to understand the impact to everyone in the organization. This could just be working from home, although I’d suggest trying a few different locations to understand where you work best. A sample progression may look like this:

  • Phase 1: Working remotely within your current city
  • Phase 2: Working remotely from another city within your state (or neighboring state)
  • Phase 3: Working remotely from a different timezone within your home country
  • Phase 4: Working remotely from a neighboring country

Remember, that it’s not just about your bosses. There might be some unforeseen leaks in communication with your colleagues as well. Review periodically, address any that you find and proceed, extending the distance.

A progressive move also gives you an opportunity to workout logistical issues, from internet connections to what you pack. If you are attempting a trip, take note of:

  • the things you forgot,
  • things that you could easily pick up in the new destination and,
  • things that you couldn’t easily find. These will most likely be must pack travel items when you’re abroad.

I’m a huge fan of Mexico as the first destination for North Americans in Phase 4. The change isn’t as disruptive as say moving to Southeast Asia. If too many variables change (language, culture, time zone, disruption of your daily routine), it can really affect your performance at work

In terms of working from another country, you’ll definitely want to make sure that tax and employment law issues are not an obstacle. They impact both you and your employer, so it’s best to know what those issues are upfront.

Photo by Surface on Unsplash

How I’m Using the 10% Rule of Side Income

The 10% Rule is a 10 year path to replacing your full-time income, starting from scratch. I came across the rule in an article by Ben LeFort , on Making of A Millionaire (Medium)

You can read the entire article here:

From the article:

If every year you can replace an additional 10% of your current income doing work you love, you can achieve financial freedom in no more than 10 years.

My return to full-time work combined with my side projects provides an opportunity to put this plan into action. As with any technique that I implement, I will be putting on spin on it. In this case, I’m going to apply the rule to multiple side projects to provide diversification and acceleration.

Why Diversification?

As we’ve learned in the past two years, life is unpredictable and events can have a severe impact on our lives and our finances. Much like an investment portfolio, I’m looking to protect myself against catastrophic changes by having multiple income streams. Even a full time job isn’t immune to economic downturns, despite the best laid plans. My previous side ventures have also experienced ups and downs. In my experience, they don’t all tend to happen at the same time.

Why Acceleration?

In many ways, I’m playing catch-up financially. I’ve made some investments with both my money and time that didn’t work out the way that I’d hoped. My career approach was very similar to the Atlanta Braves of the 90s, a team that relied on string pitching and home runs for their success. For me, the strong pitching meant maintaining very low living expenses (much like a low ERA) while depending on the long ball meant starting or working on ventures that could have huge financial upside. Like the Braves, that approach resulted in much less success than I expected (1 World Series title was a huge disappointment)

I’ve taken a step back to course correct and make some changes to my financial action plan. I’m no longer a 20-something with years ahead to keep taking big swings for the fences. So my new strategy is to employ a small ball strategy, one in which I get my runners on base and advance them in deliberate, methodical manner. It’s the approach that worked for many of the Braves’ opponents. So like a manager that manufactures runs, I’m focused on manufacturing income.

My 10% Rule Approach

I’m using the 10% Rule as defined as the basis for my strategy:

  • My current living expenses are about $2800 per month, up significantly from last year’s $1850. While I don’t expect it to remain this high, I wanted to use a figure that represented the high end of my expenses.
  • My full-time job pays enough to cover those expenses, plus some cushion.
  • My goal in the first year is to replace 10% of my living expenses, which means $280 per month from a side income stream.
  • In the second year, my goal is to increase that to 20%, which means $560 per month.
  • Each year, I’ll strive to increase the income by an additional 10%, until I reach 100% of my living expenses.

And here is where my strategy diverges:

  • I’m adding additional side income streams (extra base runners), each following the same 10% Rule strategy but staggered behind the primary side income stream. They may be staggered by an entire year or just a few months, depending on how much time it takes to launch.
  • If a particular stream outperforms the yearly goal of 10% (for example, I earn 30% in year 1), the following year’s goal remains at an additional 10%.
  • I’ve detailed my income streams on my YouTube channel.


  • I get the diversification of income streams and if I miss my targets for one of the streams (or it goes away completely), I can still maintain some progress and not get discouraged.
  • If things go well, I get the advantage of acceleration and can reach the goal in fewer than 10 years.


  • Trying to maintain multiple income streams can be draining. I’m working to make sure much of my work on these streams is closely aligned and that I’m outsourcing for help to accomplish tasks where I lack expertise.

Is It Best To Have Income Before Moving Abroad?

A question was recently posed in one of the travel groups I’m in:

1st month of my journey!!
Uruguay Jan 2016

As far as living abroad, is it best to already have a stream of income to live on? And how valuable is the American dollar?

Ideally, you’ll want to protect yourself against surprises. If you can, you want to have one or more streams of income, whether active or passive plus savings.

It’s a good idea to have an amount of money (sometimes called “runway”) that will allow you to sustain yourself without stress so you can enjoy your journey.

Financial pressures will strongly influence when/where you choose to live and for how long. Give yourself the opportunity to make the best choice in choosing your new home.

The amount you need will vary depending on your risk tolerance and your ability to generate income via:

  • Finding new clients for your business
  • Finding a new job that allows location independence
  • Launching a product/service that can generate sufficient income

In January 2016, I started my journey with a full-time job, a retainer client and, savings to cover a year of living expenses. In March of that year, I left the job and the client dropped the retainer contract in June.

Needless to say, without the savings, I would’ve been in trouble!!

Of course, I didn’t panic because I knew I could generate more income. That was largely due to the high demand in my field.

If your field has more competition, fewer opportunities, and/or lower pay, you’ll want to plan accordingly.

Need More Help?

If you’d like to talk about your journey and how I may be able to help,

Schedule A Discovery Call 

If you have a specific problem with remote work or travel and would like to strategize a solution,

Book A Consultation

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A Ritual for Letting Go

I’ve been having trouble letting go of my thoughts and feelings about a relationship that ended. After what I thought was a reasonable amount to time to process and move on, they were still occupying space in my heart and mind. It got to the point that my most recent dreams were about them.

As meaningful and impactful as this person was, holding on in the way that I was was torture, a self-inflicted kind that I needed to stop. It was obvious that they were still occupying mindshare and heartshare and I needed to reclaim that space. 

In an attempt to finally let go and reclaim my space, I returned to a ritual that provided release for me at the end of last year. The sea is accessible for me as I’m currently living on the coast of Mexico, so  I’m “taking it to the sea”.  

If I weren’t, I’d modify the ritual to resemble the Yi Peng Lantern Festival in Chiang Mai, letting the items go into the air (return it to the sky). Of course, you could even bury something (return it to the earth) or even burn it. The method is less important than the act itself.

I don’t depend on a particular date (New Year) or condition (Full Moon). I’m simply driven by the need to release something.

Much like the Loi Krathong and Iemanjá Day celebrations that I’ve experienced., I create or bring something that symbolizes what I need to let go of.  

As part of the “ceremony”, I verbally acknowledge the goodness that this person brought into my life.

And with that said, I let the items go, symbolizing the “letting go” of that relationship. Doing so is cathartic and allows me to mourn the loss and close that chapter of my life.

Do you have practice/ritual for letting go of things?

But Why Are We DOING It?

In the movie, Avengers: Infinity War, the Guardians of The Galaxy are introduced at the beginning of a new adventure. Rocket, the “real captain” of the group asks why they’ve chosen to take on this particular mission. Gamora states that they heard a distress signal and that someone could be in real danger.  In true Rocket fashion, he responds, “I get that, but why are we DOING it?”

It’s a funny bit of dialogue and further highlights Rocket’s sardonic sensibilities. But on a deeper level, the question “but why are we DOING it” provides an opportunity to dive deeper into the motivations behind the actions we take. Note that Rocket’s emphasis was on the word DOING. This is important because he’s acknowledging the generally accepted benefits of the mission while seeking to unpack the specific reasons for the group’s involvement.

Anyone can answer the distress call and take on the risks involved. Understanding why they are taking action instead of doing something else drives home the fact that we our decision making is driven by more deep-seated desires. Understanding and acknowledging them can be critical in pushing through the dips, the times when things get tough and we’re tempted to quit.

Let’s think about something as simple as eating healthier. We are surely aware of the benefits of eating better:

  • Weight control.
  • Better mood.
  • Reduced chance of disease 

But when it comes to taking the daily action of eating healthy, there is something deeper at play. That comes to the surface when, in the moment we succumb to temptation and opt for the 10 piece hot wing/fries combo instead of the salad. 

Why are we DOING that?

Rocket was looking for the driving force of the mission, the deeper “Why”. The thing that they are so connected to that will stay on mission, even when things go sideways (spoiler alert: they do).

If you are struggling with taking action on the things that you are important to you, take Rocket’s approach and dive deeper than the surface level reasoning.  

Ask “Why am I DOING it?”

What Mobile Payment Apps Do Digital Nomads Use?

Over the course of your travels, you will need to pay for goods and services. You will also need to receive payment, whether it’s from clients or friends when going out to dinner.

Why Use So Many Apps?

Not all payment systems are available everywhere so you’ll need flexibility if you want to pay/receive funds without the hassle of constantly using cash, which is often impractical. For example paying my rent in cash can require multiple trips to the ATM which have long lines, withdrawal limits and are often out of money (looking at you, PDC). 


While are some very strong opinions about PayPal, mostly about their practice of freezing accounts, there is no denying there huge presence in this space.. It is a convenient method of receiving payment and I use it when clients aren’t able/willing to pay using Wise or Venmo. However, I never keep more then a few hundred dollars in the account and primarily use it for online shopping and auto-paying a few charities that I support.


A subsidiary of PayPal, Venmo is my primary tool of choice when paying my US-based friends. Getting a check split can be difficult, if not impossible at many restaurants and it’s often easier to simple have one person pay for the tab on a credit card. 

The app is easy to download and setup. Like WhatsApp, you can now simply scan another person’s info to add them to your payment contacts

Referral link for Venmo


While living in Latin America, Xoom is my de facto bill pay tool. Also owned by PayPal, I use it to pay for my rent, Spanish lessons and reload my mobile data plan. The transfers for mobile are almost immediate and the other payments are usually available within a day. 

One piece of advice: I tried paying my rent with a bank-to-bank transfer and the verification process was a headache. Opt instead for pick-up service, in which the recipient can go to a store (ex:, 7/11, OXXO, or Walmart) to pick up the funds. It’s faster and will save you a ton of headache.


Wise (formerly Transferwise) is my default app for paying and getting paid  from people based in Europe. It is supported in approximately 60 countries.  I’ve been using it since 2017, when I signed up to pay for a co-working space in Estonia, incidentally where Wise was founded. Since then, I’ve used it to pay my European roommates and receive payment from my UK-based clients. Transfer fees are typically between 0 – 4%, depending on the amount of the transfer. Most of my transfers have been available within 24 hours and I’ve never waited longer than 2 days.

Referral Link for Wise

XE – Currency Converter

This simple and easy to use currency converter is one I use frequently when I’m shopping. If it costs more than a few tacos, I like to know how much I’m spending in my home currency.  You can monitor up to 10 currencies of your choice (which I find is more than sufficient for my current country rotation). While I only use it as reference tool, it does offer the ability to transfer funds (bank-to-bank only) and monitor currency fluctuations, complete with notifications.

iOS App | Android


CashApp is a popular app for paying people in the United States. I’ve used it in the past and it works great but my current frustration is that it won’t allow me to use my passport to validate my identification. My driver’s license is old and doesn’t scan using the tool provided.

Referral Link for CashApp

Cozumel Excursion Recap

My friends and I decided to spend a day in Cozumel, as none of us had visited the island. We were looking to close out the weekend with a fun day that would leave us refreshed and prepared for returning to work and getting the new year off to a great start.

For the ferry, there are currently 2 companies (WinJet/UltraMar) running on alternate days. The cost of a roundtrip ticket is $500 MXN (600 MXN for first class). First class provides more comfortable  seats on the inside of the ship and outdoor seating at the very front. It’s not a long ride so we opted for the regular tickets. As there were hourly departures, we opted for 9:00 AM ferry.

Once we arrived in town, we headed over to Mahi Mahi to pick up our scooters. Victor and his son were great in getting us setup and on our way. For the daily rental, we paid $500 MXN plus and additional $200 MXN for insurance. You aren’t required to take the insurance but our had several 1st time riders so purchasing provided an extra layer of comfort.

We set out on the Middle Island Road as it was less crowded and provided an opportunity for the newbies to get comfortable riding. The road, as the name implies, goes through the middle, heading to the eastern side of the island. It was a leisurely ride with no problems and we stopped at the cost to take pics before heading to our first (and ultimately final stop), Punta Morena.

Just hanging out at the beach

Once at Punta Morena, we simply relaxed and enjoyed the beautiful ocean breeze and refreshing water. Since we were a  group, we decided to simply order a few items to share, including an amazing seafood platter. In addition, there were quite a few cocktails and tequila. I highly recommend the Piña Colada and Tamarind Margarita, as they were huge hits within the group.

Additional Points of Interest

  • El Mirador
  • El Pescador – Playa Chen Rio
  • Playa Chen Rio
  • Bob Marley’s Place
  • 25th Hour Bar (Best Mojitos!!)
  • Palancar Beach Club
  • Alberto’s (

What’s In Your Bag?

Note: This post was originally written in 2017, when I ended my Remote Year journey.

“Bag lady, you gon’ hurt your back, draggin’ all them bags like that. I guess nobody ever told you all must hold on to is you.”
Erykah Badu

Remote Year ended for me in mid-March. Though the program was officially over in January, I continued to travel with my fellow Battutas, keeping the dream alive (and the cult together) for as long as we could. As I packed my bags to depart from Bali, it was apparent that I couldn’t continue to tote this much weight. My last two trips required me to remove items from my checked baggage to avoid fees. In assessing what should remain, I realized the excess baggage was as much mental as it was physical.

So after 14 months, what did I end up putting down?

  • Two cars, a house full of possessions, and the very idea of “home”
  • A ridiculous Russian nesting doll of bags starting with a 120L duffel used to carry a 90L duffel, 35L duffel, a wet bag and a tote bag.
  • Ideas about who I was and my place in the world. Some were inherited, others were freely accepted over time but all were occupying the space needed to forge a new direction.
  • Past hopes, mistakes, disappointments and missed opportunities. Continually beating myself up over these things was a waste of mental energy.
  • Relationships that didn’t work or weren’t healthy. Some of these were hard to let go of but essential to moving forward.
  • Fears about changing at this point in life.

It’s important to periodically take stock and make sure that what you’re carrying is essential for your journey.

Excess baggage is costly.

So pack light (oooh, oooh)

CNPodcast: Retrospective #26

In the latest retrospective, I share some advice on dealing with praise and criticism, explore how poor communication can ruin good relationships and take on a new challenge (that’s really an old challenge).

Lessons Learned:

Praise and critique can both move you from your path and become distractions.

  • Don’t let emotions interfere with opportunity
  • Don’t be afraid to walk away
  • Stay centered – accept, process, integrate what’s needed and move forward

You can listen to the Cocoa Nomad Podcast on the following services:

I’d love to hear from you. Reach out with comments, feedback or show ideas on Twitter or Instagram