Week 1 Learnings in Lisbon!

I’m actually here!! 

This entire month I am living and working in Lisbon, Portugal. If I’m honest, though, I have to admit that the fact I’ve launched on my year abroad hasn’t fully set in yet. For those who don’t know, I just launched on a 12-month global digital nomad journey called Remote Year. For a detailed itinerary and description, click here. Short version: I’ll be part of a remote working community of 40 nomads living and working in 12 cities across 11 countries throughout 4 continents within 1 year (1 city per month).

…but why?

There are frankly a ton of reasons why I was drawn to this program at this moment. Primarily though, I guess I’d say that I recognized that if I truly want to change the world, I need to go out into it and learn about it. So, every week I will be putting out posts about my various experiences and what I've been learning from each one. I hope that these lessons can help you as well, no matter where you are in the world. Here are my reflections from week one in Lisbon!

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Sunday: TRAVEL DAY(S) 😒 

What Happened: 

Okay, so let's back up. My journey actually began on Saturday morning at 4:30am. After burning the midnight oil to finish packing and departure prep, I squeezed in a 10-minute nap before showering, dressing, and heading to the airport for what would be the first of five flights that I'd take over the next 48 hours. Flights #1-4 went relatively smoothly (sans the sleep I expected to get on the transatlantic flight from NYC to London. Apparently there is no configuration in a plane seat that will allow me to sleep). Now, flight #4 landed me in Madrid, Spain, where I was scheduled to have a multi-hour layover, so I had planned to have a nice, leisurely meal before boarding my last leg to Lisbon. I kept my eye on the flight info and since my flight from Heathrow didn’t even start boarding until 50 minutes before departure, I made sure to get to my gate 45 minutes before our scheduled departure. 

I arrived to an empty gate with no attendee. 

I was very confused. I looked at the marquee sign nearest me and it listed the flight status as “CLOSED” (mind you, the Madrid airport the only thing they seem to use their PA system for is to tell you that they don't announce anything relating to departures or gate changes over the PA system  😑👍). I asked the attendant at the next gate over what happened and she said, “Oh yeah, they already boarded. Gate’s closed. Were you on a connecting flight?” I nodded. “Well, you’ll have to go to customer service to see if they can get you on the next flight out.” She gestured toward the Iberia customer service desk, which had a line already stretching roughly 30 people deep. I looked longingly out the window at my plane with my business-class legroom pulling away from the gate. Shit

I waited in line for 75 minutes before a woman from Iberia walked by asking, “Is anyone over here in business class?” I raised my hand and she directed me over to a Business Class customer service queue (Pro-Tip: If you can, absolutely get business class tickets for international travel. It’s not just about the awesome seats and perks on the plane. In my experience, it also gets you airline lounge access, upgraded/faster customer service, and even sometimes your own boarding gate. Worth it on long or multi-stopover flights). I waited in that line for about twenty more minutes before getting called by the only customer service agent I did not want to get. I'm not exaggerating when I say that during my time in line three different people broke down crying and all of them had worked with this guy. So, I had low expectations when I walked up...and he went even lower. Essentially, this guy spent the next twenty minutes telling me how this was all my fault because I had plenty of time to get to the flight. I told him there were no posted boarding times. He said that you’re supposed to go to your gate as soon as the flight time is posted. I said that’s not communicated anywhere. He said it wasn’t their job to babysit people. I said that 45 minutes early is a pretty standard pre-gate arrival. He said I assumed wrong. And no matter how many times I apologized and even agreed with him that this was indeed my own fault for not getting to the gate earlier, he just continued to tell me I shouldn’t be wasting his time since this wasn’t their fault. He finally handed me off to another agent who advised me that the best they could offer me was standby for the next night at midnight. Nope. I asked for my luggage and I booked a seat on the last flight out to Lisbon on another airline—which, in a fun twist of fate, was delayed by over an hour. My original 4:30pm arrival time had become 12:15am. Yaaaaaayyyyy......

When I finally arrived in Lisbon, Remote Year had an amazing local driver waiting for me and he gave me a huge download of the city as we drove through it. When we arrived at my apartment around 12:45am, Gonçalo (our main city lead) helped me unload my luggage, carry it up the 145 stairs to our apartment (I have since counted), and give me a quick tour of the apartment. After unpacking and brushing my teeth, I finally hit the sheets around 1:15am. 

What I Learned: 

The incident in Madrid was the first time in all of my airline customer service interactions that I truly felt like I had an enemy across from me. Having worked in CS for many years in many industries, I always try to meet the person where they’re at. I know their job isn’t fun. That’s why I try to be the bright spot in their day even if I’m there because there is currently a cloud over mine. This time, however, there was no breaking through. I truly was in a new territory and was therefore given the opportunity to have a growth moment.

This experience reminded me that despite your best intentions and efforts there will be people you'll encounter throughout life who just want to stay in their zone—no matter how negative that zone is, and if you allow it to, experiences with people like these can tempt you to become negative and cynical yourself. But allowing one negative experience to change the way you interact with an overwhelmingly positive world is like changing your entire website because one user didn’t like it. You’d never do that, especially if they weren’t a target consumer (and this customer service rep certainly wasn't someone I'd consider to be my target customer). Too often we change our way of thinking or acting because of the attitude/actions of someone to whom we wouldn’t normally lend any credence. Stop that! Keep giving people the benefit of the doubt 🙂 Kindness costs nothing but yields much, which reminded me of a sticker I have on my laptop for just such occasions: 

be kind anyway.jpg

Monday: Program Launch and Birthday #1

What Happened: 

At 10am Monday morning was our city welcome, in which Gonçalo and Ligia—our city leads for Lisbon—gave us a quick overview of our month, the city’s history, as well as some current political topics to be aware of. For some of us, this was the first time seeing our community of forty Remotes (Remote = person on a Remote Year itinerary). To get us mingling our Program Lead Erica split us into randomized groups of about 5 for a game of “Lunch Roulette.” Each group was given a list of restaurants within walking distance, and off we went! During lunch we tossed out questions to each other, like, “What made you sign up?” and “What’s something in your bag that you absolutely will not part with during this year?” Starting off with this type of questioning helped us learn a ton about what mattered to each other in a relatively short period of time. During lunch, I also discovered that one of our group members name Sean and I had more in common than being tall (he’s 6’7”!). This will come into play on Thursday 😁

In Gonçalo and Ligia’s presentation, they told us about some of the historical buildings in the city, one of which was a church whose roof had been fallen in during an earthquake killing the entire congregation, and out of superstition, the roof was never replaced (Lisbon Fun Fact #1- They have a crazy history with many of their ancient churches there! Seriously. Google the histories of the churches on this list and you’ll see some insane stories). This piqued the group’s interest enough that we decided to seek it out after lunch. Along the way, we ran into another Remote group who wanted to grab beers to celebrate one of our group member's birthday. Clearly, we joined in. Arriving at a rooftop bar, our group of about fifteen took over a long set of connected picnic-style tables and the conversations began.

Those who know me well know that I’m not a "big group" type of guy. I like small, intimate settings where you can have a real conversation with someone, so I was once again out of my comfort zone. Because of this—regardless of the great conversations I was having and the cool people I was meeting—it only took me about 15 minutes to start concocting my exit strategy. Unfortunately, due to what I have come to know as “Portuguese-style Customer Service” (read: slow and infrequent service from servers), it was a solid hour before I was able to receive my drink, consume it, and pay for it. Once that happened, I advised the group I needed to head back to the co-working space to get some work done (which I actually did), and I hit the road. Upon returning to the workspace, I found a handful of dedicated workers cranking away on their laptops and taking calls. I felt at home 🙂 

What I Learned: 

This year will be full of opportunities for exciting and fun things to do. There will literally be a party or access to one every night, especially this month. There will always be someone to get to know better. Something new to learn or experience. There will always be something other than work to do and not enough hours to do it. I may see it in an amplified form right now, but that’s honestly just life.

All of us have choices to make every day about how we spend our time. We often have the choice between three broad buckets of how we can spend our time- 1: What is most important, 2: What is most urgent, or 3: What is most fun. There are certainly subcategories and variations of each bucket, but these categories are pretty much how we analyze our options. Is something time-sensitive? Is it something that’s going to move us forward in a meaningful way? Is it something that comes to me easily/something that I’m going to enjoy doing? So much of life is trying to figure out what really matters and what’s worth our time. The buffet of options I had this day reminded me that I need to keep a long-term perspective. Knowing that there will be more parties makes me feel more comfortable missing the current one. Being left out of a group lunch is okay with me, because I will have a year’s worth of lunch opportunities. Keeping a long-term perspective hedges against FOMO and helps you feel more satisfied with the choices you make when prioritizing Important stuff over Urgent and Fun stuff. 

 The view from the rooftop bar 🤩

The view from the rooftop bar 🤩


Tuesday: Jetlag and Sunsets

What Happened: 

Tuesday’s schedule included a one-hour language and history course at 10am and a group trip to observe one of the best sunset views in the city around 8pm. So, my plan was to wake up around 9am, get over to the language and history class, head to the workspace after it ended around 11am, and pretty much work all day until we left for our sunset outing. Unfortunately, I conveniently forgot that jet lag even affects those of us who travel for a living. My alarm at 9am was met with dismissive laughter and a roll the other direction. When I actually woke up around 2pm, I felt well-rested and very hungry. Along the 10-minute walk to the workspace, I stumbled upon a restaurant called, “Hamburgueria Portuguesa.” As a person that pretty much exclusively enjoys land-dwelling creature meat, I was intrigued and excited by the thought of a Portuguese Hamburger. I stepped inside.

After ordering the Portuguese Burger—H. de vaca with Portuguese sauce of garlic and bay leaves, starry egg, ham, and French fries—I was surprised to receive a bunless ground beef patty nestled into a mass of fries and covered in a fried egg and a thin slice of ham. It was delicious, but certainly not what I’d expected. After wrapping up my lengthy lunch (Lisbon Fun Fact #2- You cannot physically have a sit-down meal in a Lisbon restaurant for under 90 minutes. Between ordering, getting your food, and getting the check, it's a very slow process), I headed to the workspace where I was heads-down for the next several hours. 

At 8pm our group assembled at the workspace and Set off on a 15-minute walk to the top of a nearby hill. Atop the hill was a lookout spot with a bustling scene filled with locals enjoying lively conversations and the sprawling view, even though the sunset was blocked by light cloud cover. The air was a vibrant mix of loud voices, music, beer breath, and grilling food. It was amazing to be in a place with so much positive energy around. Everyone was there simply enjoying life. What a way to end the night 😊

What I Learned: 

Things will go wrong. You will underestimate what your body & mind requires to function and you’ll need to unexpectedly take some personal health time. Your burger will come out wildly different than you expect. Your meal will take way longer than you anticipated and you will subsequently have about half the amount of time to work that you expected. Your sunset views will be covered by clouds, blocking that “perfect insta pic.” Life is unpredictable. However, life is 10% what you plan and 90% how you react. The people hanging out at the top of the hill were unphased by the cloud cover. They were just glad to be together with friends, having good food and good conversation. It's important to have an attitude that allows you to roll with the changes and adapt so that you can maximize the time within your control so that you can be fully present in the moments you share with others. Those are moments you cannot savor once they’re gone. 

 Even with the clouds, it was still a stellar view.

Even with the clouds, it was still a stellar view.

Wednesday: The Walking Tour and Catching Up

What Happened: 

Determined to not have a repeat of my previous morning, I made sure to wake up in plenty of time for my 10:30am walking tour of Lisbon. After some navigational errors, I met up with my group and our leader Katrina from Sightseeing Lisbon, a local sustainable tourism company. Katrina took our group of eight through various neighborhoods, describing the fascinating, and often barbaric history of Lisbon. Some of the big takeaways from this tour for me were that 1- Pretty much every historic building in the city has survived either a fire, an earthquake, a massacre, or some combination of the three, and 2- Tourism is actually hurting the local economy of Lisbon more than it’s helping (If you’re interested in learning more about the reasons for that, check out this amazing article from another Remote, Rebecca Stone). 

After returning from our three-hour tour and two-hour lunch/dessert (which included a stop for some of the city’s best pastel de nata at Pastéis de Belém, one of the oldest sweets-making shoppes in Lisbon), I set back to the workspace and worked from around 3pm until about midnight. It sounds like an intense heads-down work session—which it kinda was—but there’s something soul-cleansing to me with getting caught up on work. When things are hanging over my head, people are waiting on responses, or I have incomplete work, it feels like a massive weight on my shoulders and I carry it with me throughout the day. Being able to get to even a manageable level of work that I knew I could wrap up the next day was exactly what I needed. 

What I Learned: 

The tour and article I shared really got me thinking about things in a different light. Normally, we make a blanket assumption that if we are coming into a place and spending our money at local shops and paying local salaries that we’re making a positive impact. The logic seems pretty simple. However, when you dive into the specifics relating to individual economies—and especially those of rebounding areas—you being to realize that over-tourism has the potential to do way more harm than good. Considering the fact that in Lisbon tourists outnumber locals 9-to-1, you can imagine that there’s an unhealthy policy and spending tilt toward tourism-focused industries. Much like the strain that people living in NYC, SF, and Denver are feeling around overcrowded cities and the resulting cost-of-living hikes, locals in Lisbon are feeling the pinch, and even in a bigger way than many in big US cities. For perspective, rent may be $2,500/month for a low-end studio/1-bedroom apartment in NYC, but in general, wages are typically higher there than in many other markets to help offset that inflation. In Lisbon, a low-end studio/1-bedroom apartment has jumped to around €1,200-€1,500 while the typical wage of a city worker has stayed around €5.50/hr in a primarily no-tipping economy. These rent prices have jumped largely due to the rise of Airbnb and other short-term rental properties popping up, displacing many of the people who have lived in these neighborhoods for generations.

Many of you are already familiar with gentrification’s impact so I’ll let you read Rebecca's article for more details, but it really brought into focus for me that we are not always the "good guys" in the story, even if we think we’re doing right by people. It’s super important to stay aware of how your actions truly impact the people around you, not just how you hope that they do. 

 Graffiti like this can be found throughout the city

Graffiti like this can be found throughout the city

Thursday: Inspiring Lunches and Mixology

What Happened: 

On Monday, I mentioned a guy I met during lunch roulette named Sean. Sean wasn’t actually on the Denali itinerary with us, but he was actually from an itinerary that had launched a couple of years prior and has been living and working in Lisbon ever since. Well, unbeknownst to both of us, we had been in contact with each other two years ago.

Around the time that Sean was getting ready to launch on his program, he took Start With Why's online Why Discovery Course and was so inspired that he reached out to his Program Lead about having the SWW team come out to lead their entire group through a Why Discovery Workshop. At that time, I was pretty much the only igniter in our lineup that fit their needs & price point and had the flexibility to hop on a plane on short notice to do it, so I was looped into an email chain with him and his Program Lead to discuss how we could make it work. It didn’t end up panning out at that point, but nonetheless, when we realized who each other was during lunch roulette, we immediately set up a follow-up lunch for Thursday to talk about everything Start With Why. When we got to the taco shop, we spent an entire hour and a half talking about his WHY, mentoring others along their WHY journey, and ways to hone and refine your own WHY and HOWs. It was a rejuvenating conversation and I was thrilled to have met such an inspiring leader (plus, we had amazing tacos. So that helped). 

That evening was a definite highlight of my week- We got to attend a mixology class! A group of eight of us joined a local couple that runs 4 Caravelas for an amazing night of learning, games, and of course, drinking delicious drinks. While the drinks were amazing, to me, the night was made most special by the way that our teachers conducted themselves. Through the entire course of the evening, the joy for what they do and the joy they take in their relationship shone through, and that joy was truly contagious. 

What I Learned: 

Lunch reminded me that the world is simultaneously enormous and tiny. Think about the insane odds of 1) Sean writing that email 2 years ago, 2) Me working at Start With Why when that happened, 3) Me being the igniter that was matched with the event, 4) Me deciding two years later to go on Remote Year, 5) Sean wrapping up his RY itinerary and deciding to move to Lisbon full-time, 6) Me ending up on an itinerary that took me through Lisbon, 7) Sean deciding to work at the RY co-working space and not somewhere else, 8) Sean being there during lunch roulette and deciding to hop into a random group, 9) Sean getting randomly assigned into our group, 10) Our group asking the right questions to spark that memory in Sean’s head, and the list goes on and on… It’s crazy to fathom that if even one of those things had changed, our encounter would've never happened. The world is vast and there is so much out there to explore and experience, absolutely; but the universe has a habit of bringing a little bit of home to you when you leave it behind—for better or worse. It’s nice to know that in this massive corner of the universe, this is the most connected our world has ever been, and it’s just going to get more connected. 

 I totally won, you guys. Just FYI...

I totally won, you guys. Just FYI...

Friday: Clutch Zooming and Pecha Kucha

What Happened: 

After a week of new experiences and new faces, it was nice to see a familiar one on Friday. My friend Tim set up an hour on my calendar to catch up via Zoom. While everyone I've met here so far has been great, having a conversation with a friend from home was a welcomed change of pace. Our conversation centered me for the rest of the day and reminded me that keeping in touch with folks back home needs to be part of my routine while abroad. 

Friday evening was a RY tradition for week one, called "Pecha Kucha Night.” It’s based on the Japanese Pecha Kucha format of presenting, which can be summed up as, “20 images in 20 seconds.” It’s designed to be a concise and inspiring presentation format, and RY has taken that essence and made its own version of the practice. On Pecha Kucha Night, the entire group gathers and each member has thirty seconds to present one slide that describes who they are. You pick the content and information, but everyone abides by that same format. It was great to get a bite-sized vibe of everyone's different personalities and priorities through these presentations. And it also helped me to put lots of faces to names, which I typically struggle with 😉  

What I Learned: 

I can get lost easily in what’s in front of me. I have a very strong tendency to slip into an “out of sight, out of mind” mentality throughout tons of areas in my life. Unfortunately, I think a lot of us can fall into that trap. Making time for people back home needs to be a focus for me because I need that anchoring in my life. 

Additionally, Pecha Kucha reminded me of two things- 1) Summing yourself up in 30 seconds is insanely difficult yet interesting, and 2) I still prefer 1-on-1s to get to know people 🙂 

 Pecha Kucha night!

Pecha Kucha night!


Saturday: Orientation and Festival Mode

What Happened: 

Saturday was our full-community orientation where we spent around 5-6 hours going over program details, what to expect, code of conduct, the RY team, and everything in between. This was a good mental check for our crew that we weren’t just a bunch of people that happened to be traveling together; we are a community. Much of the day was focused on this community aspect—both with our internal community as well as the local communities we’ll be joining—which was a refreshing reminder of why many of us signed up in the first place. 

In Monday’s learnings, I mentioned that this month is a crazy party month in Lisbon and, lucky me, I got nested right in the center of it all 😬 During our City Welcome and Orientation the RY team reminded us several times that the alleyways throughout the city—and specifically those around our apartment—will be packed with locals enjoying the abundance of food stands, booze carts, and lively music. As Saturday night was the first weekend of June, we got our first true experience of it, and the only way I can really describe it in today's terms is to say that it was the physical manifestation of 🔥 (lit, not fire). People were shoulder-to-shoulder throughout every side street around our apartment, music blared in every direction vibrating each wall, and food was being grilled up and sold at each corner. It was simultaneously awesome and dread-inspiring. 

What I Learned: 

Both of Saturday's events reminded me that one big commitment I made to myself this year was to be invested in my RY community. I’ve been a digital nomad working in a physical bubble for over two and a half years now, and community is the biggest thing I’ve been missing during that time. I have a great team at Start With Why, and they truly are who I consider “my people,” but there is something amazing about being able to physically walk over to someone and have an impromptu conversation that video conferencing will likely never be able to solve for. I have been craving a physical community for a long time now and I saw RY playing a huge role in filling that void. This, however, needs to include the people of the communities in which I’ll be living and working. Even if they are unaware of it, they are providing me an immeasurably valuable service. As such, I want to respect and support them—and not just when it's most convenient. I need to push myself into the “growth zone,” which for me includes not being a hermit like I naturally do. I need to fully experience and participate in different cultures to be able to show up and contribute fully. So, I am committing to trying new things that normally I would shy away (or even run away) from—things like seafood, big group activities, exploring a place that is not convenient to my commute, talking to a stranger, and much more. 

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In conclusion…

This is going to be a wild year. I’m excited for it, but I also know that it’s going to be an uncomfortable year. If I want to grow like I need to this year I will be spending a TON of time outside of my comfort bubble. That terrifies me. But as you've probably experienced in your own life, the most rewarding experiences come from leaping into your personally unexplored territory. Knowing that, I’m moving forward with a sense of nervous excitement for the journey and I’m looking forward to having you all join me for the ride.