Working Remotely from Italy
Ciao, ragazzi 👋🏽 I’m writing to you from beautiful Italy. After getting fully vaccinated a few weeks ago, my husband and I simply couldn’t pass on the opportunity to safely re-visit one of our favourite countries. I mean, a summer in Italy with little to no crowds?! Where do I sign?!
I’ve spent six glorious weeks in Italy - not on vacation, although there are many moments that feel and look like I am. Instead, I’ve been working remotely. Because, despite the collective crisis we’ve all faced over the last year and a half, there are tangible and transformational opportunities that can be found, cultivated, and leveraged in the aftermath of this pandemic. Remote work is one of those opportunities.
Remote work has been around for a while
Despite its recent widespread adoption, remote work isn’t new. With the emergence of social media, digital communication and creative tools, as well as sourcing platforms like UpWork, freelancers all over the world have been cashing in on this flexible way of working for years. Since it’s founding in 2011, Zapier has been a fully remote, “digital by default” tech company, hiring staff from 28 different countries and varying time zones, without ever having anyone set foot in an office, ever. And, of course there’s the entire fleets of sales forces at enterprise-level corporations. Though not entirely remote, they were the first in most Fortune 500 companies to take their work on the road, so to speak.
Previously framed as a rare exception for outlier cases, few people in traditional 9 to 5 jobs could enjoy the freedom and flexibility of being able to work from home, or work from anywhere. I recall often feeling like I was asking for some exclusive, or forbidden perk whenever I’d ask a potential employer, “what’s your work from home policy?” Almost always, they’d answer with, “We prefer people to come into the office, as it’s better for collaboration”. Or worse, “We’re flexible! If you’re sick you can work from home”. I once worked at a tech company that had “Work from Home Wednesdays”. Evidently, a perk only the engineering and development teams ever seemed to take advantage of. The one Wednesday I worked from home, I logged into Google Meet, turned on my camera, and saw that I was the only one from my team that wasn’t physically present in the conference room.
Seeing the past with rose-colored glasses
Before a global pandemic, there was no precedent for companies to have an entirely, or mostly remote workforce. We’d become stalled in an antiquated industrial complex where productivity and output is measured by how early you punched in, how late you punched out, and how long you stayed fixed at your station. Why are copywriters, graphic designers, accountants, and project managers still being held to the same work standards and practices applied to workers at car manufacturing plants, garment factories, and coal mines?
Granted, remote work isn’t without its challenges. But, as we’ve been battling with this “new normal”, are we forgetting the hurdles that came with the way things were? Numerous studies have found that “negative details about past events drift out of our memory over time while the positive aspects of our past experiences remain.” This mental and emotional phenomenon is nicknamed the “rosy retrospection” cognitive bias.
Are we forgetting about having to cram into tiny, windowless, over-air conditioned conference rooms to “collaborate” on something that could have been an email or a Slack message?
Are we forgetting cold, bagged lunches, or having to spend $15 on a basic salad from an office park deli?
Are we forgetting subway delays?
Bumper to bumper evening gridlock?
$400 monthly commuter train passes?
Only seeing your kids for an hour before bedtime?
Need I continue?
Office mandates are an executive power play
As a people person, I enjoyed connecting with my colleagues, eating the occasional lunch together, and going on afternoon coffee walks. But, all of that was under the mandatory circumstances of being forced to come into an office, I was making the most of something I had little say in.
In the same vein, when I started my own company and hired a team, I often wished to have an office. But, honestly, it was because I wanted an office - plain and simple. I wanted a physical space that reflected our brand. It was less about being better able to connect, collaborate, or about our contributing to our culture. Clearly, we had already built great rapport from working remotely. So, what good was it going to do to spend valuable revenue on a physical space and then force people to commute to it? Instead, I used that money to re-invest in hiring more people, paying competitive wages, and allowing my team to have the flexibility they needed to live rich, holistic lives that didn’t revolve around work. You know, stuff employees actually care about.
Collaboration doesn’t require being under one roof?
The notion that collaboration requires people being physically present in an office is laughable. It’s a power play by execs and managers who relish the optics of seeing “asses in seats”. It’s how they measure productivity, output, and success. Myself and two colleagues at a tech startup were once reprimanded for leaving work at 5pm every day. Apparently us leaving at the allotted end of our work day made it seem like we didn’t want to be there. New flash: we didn’t. We couldn’t care less about “hanging out” and having a beer with the Sales bros. I was a newlywed, whose only priority was getting home to have a nice dinner and evening with my husband.
With cloud-based tools like Google Suite, Slack, Zoom, Asana, Figma...you name it, there’s literally no reason why creativity, coordination, and collaboration aren’t possible remotely. I recently had a recruiter reach out to me about a contract job. When I asked about their remote work policy, they said they would require employees to come into the office 50% of the time because “they collaborate better when in a room together”. I responded with, “were they not able to collaborate over the last year and half being fully remote?” I’m not trying to be facetious, but genuinely trying to understand what grounds these arguments and conclusions are coming from?
Look, I get it. There’s something special about sitting across a table from someone. It sparks a different kind of connection and excitement. But, why does that mean having to commute into an office every day? Why not meet intentionally at quarterly or semi-annual retreats? Why not facilitate casual work or collab sessions at co-working spaces or coffee shops? Or, how about letting employees decide the best ways that they want to collaborate with one another? Last I checked, grown adults are capable of making decisions for themselves.
Bouncing ideas or just making small talk?
Lastly, the idea that people were “bouncing ideas off each other in the hallways” is also a complete farce. Rosy retrospection cognitive bias strikes again! In reality, these interactions were most often useless chit chat and small talk, asking “how was your weekend?”, on Mondays, “got any plans for the weekend?”, every Fridays, or “did you get that email I sent you?”, every other day of the week.
Because of office dynamics (read: politics), most meaningful connections were happening at a peer-to-peer level - executives with other executives, managers with managers, and so on. Serendipitous aha! moments don’t happen just because you threw down a bunch of bean bag chairs and a beer cart in the common area.
Upward momentum and connection is still possible in a remote setting, but it’s up to management to intentionally carve out those opportunities for people. Perhaps that means setting up regular one-on-ones with people? Creating mentorship programs? And again, having meaningful and thoughtful in-person retreats, meetings, or events that might facilitate connections outside of the monotony of day-to-day work.
The opportunities of remote work
I recognize that remote work isn’t going to be for every company, and certainly not for every person. But, I’d venture to guess that as restrictions loosen and lift, remote work is the better option for most people.
For employees, remote work means lunch hours where you can squeeze in a nap to feel refreshed for your afternoon. It means ditching that hour-long morning commute to get in a great workout without having to haul a heavy gym bag to and from an office. Or, it can mean starting your day by visiting the Uffizi Gallery and seeing Botticelli’s The Birth of Venus, and bring that creative inspiration and energy to your work. Had to throw in my own personal experience in there, of course 😜.
For employers, it means saving hundreds of thousands, if not millions of dollars on pricey leasehold agreements, office equipment, and maintenance. Those funds can be reinvested into hiring, improving employee benefits and programs, developing new product or service lines, or expanding into new markets. There’s also an opportunity to recruit the best talent from different cities and global markets, and becoming an attractive option for those actively seeking flexible, remote work.
Admittedly, this blog post has taken me weeks to write. I started it while at a cafe in Rome, continued it on the train to Napoli, and later in my hotel room in Bologna. Now, as I complete this post from my a cafe in Milan, I can’t help but feel anything but gratitude and humility that this is how I get to live and work. I recognize the social, physical, and financial privilege that affords me these kinds of opportunities. But, it also requires courage to firmly decide what you want out of life, intentionality to make it happen, and tenacity to hold on to that vision when inevitable challenges arise.
Comment below and let me know whether you prefer working in an office, having work from home flexibility, or working completely remote? Also, if you could work from anywhere, where would that be and why?
Until next time, friends...Ciao e Grazie Mille!
Octavia
My Recos
If you’re planning on traveling to Italy soon, here’s my list of the best restaurants and cafes to try:
Rome
Ivo à Trastevere - best affordable spaghetti carbonara. Located in the eclectic, picturesque neighborhood of Trastevere.
Barnum - best coffee as well as delicious, healthy lunch and brunch options. Their chicken veggie stir fry with rice was amazing, and a nice break from constantly having Italian food. They have very friendly and welcoming staff (ask for the barista, Kevin…yes, an Italian man named Kevin). It’s also a great place to meet other international travelers and strike up some great chats. We met a journalist from Ireland, a student from Germany, and a Stripe employee from San Francisco.
Osteria Santa Lucia - incredible, unique take on Italian cuisine. They have a beautiful, lush, romantic patio. Be sure to try their ricotta-stuffed puff pastry with fried onions drizzled with traditionally aged balsamic vinegar.
Amalfi Coast
Stella Maris Restaurant and Beach Club - I had their linguine frutti di mare for lunch and dinner on the same day - it was that good! The owner was also our Airbnb host; she hooked us up with a great spot on the beach with an umbrella, towels, and two chairs.
Florence
Osteria Santo Spiritu - Hands down the best gnocchi ever! In fact, they are famous for it. But, their simple spaghetti aglio, olio e pepperoncini dish was mouthwatering. I had it for dinner twice.
Ditto Artigianale - best artisanal coffee and brunch. They have three convenient locations in the city, and are a great place to work, grab lunch, and even stay into the evening for a drink.
Chili Casa - yummy Asian fusion restaurant when you need a break from pasta and pizza.
Bologna
Cremeria Cavour - creamiest gelato with unique flavors. There was always a line up outside.
Modena
Parmesan cheese (general) - Not a specific place, but the Parmesan cheese in this region is unlike any other in the world - so fresh and creamy! Be sure to grab a mixed cheese and meat board if you’re ever in the Emilia-Bologna area (Parma, Modena, Bologna)
Aceto Balsamico - DOP (general) - We did an amazing Airbnb experience all about authentic, traditional balsamic vinegar. Our host, Guido, took us to his family home, showed us his barrel room, and allowed us to taste his personal 40+ year old yield of vinegar atop Parmesan cheese, over dark chocolate, and my favorite, drizzled over vanilla ice cream. It was one of the highlights of our trip.
Milan
Loste Cafe - for delicious artisanal coffee and a beautiful space to get some work done.
Costa Azul - authentic Salvadoran food in the heart of Milan? Believe it! Their pupusas were fresh and delicious, almost good as my Mother-in-law’s. 😜
