What I learned working as a Program Leader at Remote Year
Customer support lessons after a year on the world’s best job
Between October 2017 and September 2018, I’ve led a group of around 40 digital nomads on a work and travel program around the world with Remote Year.
Together with my co-pilot Jolanda, we’ve handled all sorts of customer support issues, organized community events and cultural immersion activities across Split, Prague, Lisbon, Kyoto, Chiang Mai, Kuala Lumpur, Buenos Aires, Córdoba, Lima, Medellín, Bogotá, and Mexico City.
It was, in many aspects, a dream job. The dream job. We got paid to travel to all these incredible countries, together with a group of incredibly inspiring people from all walks of life, and supported by an incredibly caring, kick-ass, funny, and hands-down impressive team.
It was also a complex job. There’s something to be said about a job where your customers are also your travel mates and your friends, you feel on 24/7, and you need to hit the ground running in a brand new city every month, navigating through new languages and cultures and teammates. Despite and because of these challenges, I deeply loved this job and wouldn’t have traded this opportunity for anything. I’m coming out of it feeling like a new person altogether, a better person.
🙅 Don’t try to be right
I’m proud of having lived this year the way I did. Taking this job was an incredible opportunity to see the world and learn new things, as well as an incredible leap of faith. A nice job and an apartment I adored, in a country that felt like home, that I knew I probably wouldn’t return to — I threw it all out of the window for a great unknown. In many ways, I was scared. I thought long and hard before taking this job, a thousand fears dancing before my eyes.
None of those fears, it turns out, materialized. Anything that seemed like a challenge the months before I took this job quickly became second nature.
The end of the year did, however, come with some regrets. Things big and small that, looking back, I would have done differently.
But the only thing I truly, deeply regret is each one of the moments when I tried to be right.
The few moments when I allowed myself to give in to stress, or jet-lag, or anger from a less polite request, and gave a hot-headed or curt response. I was wrong. I was so wrong. My job wasn’t to be right. My job wasn’t to respond to my own feelings. My job was to support my customers’ lifestyle during a year that was intense and demanding for them.
I deeply regret each moment when I was anything less than calm and polite.
At the same time, I’m incredibly grateful that for each of these occasions, I was able to take a step back and make amends. It was the most difficult and most important lesson to learn.
I can’t control what happens. I can only control my reaction to it.
✉️ Write an angry letter and never send it
I’m an emotional person. I’ve long learned to not pretend otherwise, and use it to my advantage.
Whenever I felt angry or frustrated during this year, I took to venting by writing email replies I’d never send, where I would give free reign to my upset, passive-aggressive, and shade-throwing self.
This gave me an outlet for my emotions, and allowed to put the situation in perspective. No matter how outrageous my letter was, I’d finish it seeing the person on the other end not as a target to put down but as the person I cared about who had a problem I could help with.
After writing the angry letter, I could then write an acceptable letter and, ultimately, solve the problem.
Recently, I found out that Lincoln himself was given to a similar habit, which he called “hot letters”.
🙏 Kill them with kindness
Every time I wrote an angry email, it also allowed me to think about what would happen if I would actually send it.
Sending a passive-aggressive reply would perhaps make me temporarily feel avenged, but it would also spark a war of words while likely damaging my relationship with that person.
“Kill them with kindness”, my colleagues often reminded each other. Or, in the poignant voice of Billy Corgan, “Disarm you with a smile”.
Relentless politeness defuses tension. At worst, it allows us to stay in control of the situation. At best, it gives the person on the other side an opportunity to acknowledge that they might have spoken a bit too strong and backtrack on their harsher words.
I’ll go with kindness any day.
😖 People crack under stress; don’t take it personally
I had the privilege to travel with some of the best people I’ve ever met. After a year on the job, I’m proud to say that the respect, admiration, and friendship I feel for my customers only grew.
That isn’t to say that it was all smooth sailing. Working in customer support means working where things break, where customers aren’t happy and are inconvenienced enough to ask questions or complain.
As a lifestyle business, at Remote Year this is multiplied by ten — we answer for many key aspects of our customers’ lives, including their apartments, their ability to connect to the internet, many of the events they attend, much of their travel, and even the countries where they live.
Add this to culture shock, jet lag, personal and professional issues, homesickness, and travel fatigue. These can wear anyone down, and as a lifestyle provider, we often were the target of this stress.
Even after learning to let a greater deal of things slide off my back, someone lashing out at me will always come with a bit of a sting. But going through this intense lifestyle together with my customers gave me the gift of not sliding into an ‘us vs. them’ mentality. It allowed me the clarity to see that everyone needs an outlet under stress. Being on the wrong side of that stress doesn’t mean we’re incompetent, or that the other person is horrible.
🚑 Act where it hurts
At some point, I had to make a decision that would either inconvenience the whole group, or only a handful of people. Because I didn’t want the situation to blow out of proportion and the entire group chattering about it, I determined that the best course of action would be to make the decision that would rather inconvenience the smallest number of people.
I miscalculated this step.
I’d tried to minimize the discomfort for the whole group, when in reality that handful of people’s pain point was much more pressing. By only regarding the number of people inconvenienced, I didn’t act where it hurt the most.
Unfortunately, sometimes there are no perfect solutions. Times when we need to give news that people don’t want to hear. But when faced with a seemingly lose-lose situation, considering the most pressing pain points first, rather than just numbers, is a good rule of thumb.
👯 Invest time in your relationship with your team
I’ve mentioned already that the Remote Year team is one of the most incredibly caring, kick-ass, funny, and hands-down impressive teams I’ve ever had the privilege to work with.
But this year also brought about a relationship unlike any other. In its original conception, every Remote Year community had two staff members who traveled with the group throughout the year.
When I was initially hired, this made me apprehensive. Accepting this job meant accepting living and working with a then-undisclosed partner for an entire year, day in and day out.
Then I met Jolanda, about a month before starting our training. We clicked immediately — as introverts, we both felt comfortable and not drained in each others’ presence, which we guessed would be a major advantage throughout the year. We weren’t wrong.
It’s was a powerful bond. We were each others’ closest co-worker, more often than not we lived together, and we were the only person who completely understood the others’ context throughout the year. When Jolanda’s sister and brother-in-law came for a visit, one of their observations was: “You actually call each other ‘Wife’??”
This relationship is one of the best aspects to come out of this year. It was also an excellent reminder that mindfulness goes a long way in starting and nurturing good relationships, whether personal or work-wise.
Keeping it real: The Blueprint of We
We started our relationship by getting together to draw our ‘Blueprint of We’. This was an extremely useful methodology to get to know each other and quickly start collaborating together. Not only it gave us very specific answers about our temperaments and work styles, but it also allowed us to share some backstories — important since at that point we had known each other for about 2 weeks. It also led to a few self-discovery moments, to insights we had never externalized before.
The Blueprint of We has 5 main components:
1. The Story of Us: Share what draws you to these people and this situation.
2. Interaction Styles and Warning Signs: The “blueprint of me,” how I work best, what I look like on a good day/bad day, and what I might need that I couldn’t ask for in the moment.
3. Expectations: Core values and non-negotiables, the structure you need to create and sustain this relationship.
4. Questions to Return to Peace: A tool to return to peace if the need arises, makes the difficult times shorter and easier.
5. Short and Long-Term Agreements: How long you’re willing to go before you make peace. An agreement of no outright harm, a willingness to keep an open window if the unimaginable happens.
We spent a full, uninterrupted morning doing this, first reading through the entire document and then following the steps.
For the first two steps (intra-personal), we first took the time to think of the answers on our own, and then discussed them together. For the following steps (inter-personal), we discussed them first, and then noted them down.
We used post-its (which we saved), but I’d advise people to use whatever tools they want/have available, as long as the end result is a document that they can go back and refer to at any point.
Keeping it weird
Jolanda and I stayed real this year. We cried in each other’s shoulders over personal and professional woes, had long talks, kept each other accountable.
But, living and working so closely for so long, it was also key for us to give each other the safety to be as weird as we get. That was an escape from stress and brought us closer together. Weirdness factors included:
- A shared burger ranking around the world: in each city, we ate at least one burger which we evaluated in a world-rank.
- Petting stray animals.
- Heated debates on all things coffee over tea, optimal cooking point for eggs, the aesthetics of naked cats, and so much more.
And the list goes on. Being weird with your colleagues is not just nice, it’s life-changing. In the days where all things seemed to be going wrong, it made all the difference to be able to bounce ideas with someone who both understood what I was going through and also dramatically told me “I was dead to her” because I forgot to drink my tea.
💆 Relentlessly take care for yourself
Between calls with my fully distributed team (which meant anything from 7 AM calls in Mexico City to 1 AM calls in Kyoto), periods of a higher volume of work, socializing, and all sorts of unexpected situations, keeping a routine was hard in the best days.
It’s easy to let work creep in. To skip workouts, cooking, meditation, writing, catching up with friends, for the sake of being “too busy”.
As Debbie Millman would say,
Busy is a decision
We’re rarely ever too busy to do anything. Most times, we’d simply rather do something else. It’s a cop-out for a ‘no’. I’ve been guilty of this, time and time again.
Over time, the health debt creeps in. I’ve experienced weight gain, acne, and burnout. All things that could have been avoided if I hadn’t used being too busy as an excuse to take care of myself, to workout, to eat well, to catch up with my old friends back at home.
For me, working hard is important. However, being mindful about where the hours in the day go, prioritizing, allowing time for the important non-work things, has proved to be better in the long run. After all, we can only do our best work if we are feeling our best.
If you read this far, thank you for your time! To sum up, these are the key things I learned this year:
- Don’t try to be right
- Write angry letters (and don’t send them)
- Be kind at all times
- People crack under stress, don’t take it personally
- Focus on the biggest pain points
- Be intentional with the relationship with your team
- Relentlessly take care for yourself.
If you have any questions, thoughts, or feedback, I’d love to hear from you!
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