Editor’s note: Billy Warden is a writer, marketing exec and multimedia producer based in the Research Triangle, where he co-founded the p.r. agency GBW Strategies. He is a regular contributor to WRAL TechWire.


RESEARCH TRIANGLE PARK – Marco was almost off the call with a senior vice president delighted in his world beating sales work when the dreaded question came.

It was Lockdown Times, and the VP innocently inquired as to how Marco was faring in New York City, where their company was based and where Marco had, before COVID, made his sales calls from an office bullpen alongside colleagues.

In fact, Marco was 3,200 miles away, in Dublin. He hadn’t informed the company. “I was the number one account manager at my software company,” he says now, “and with that in my pocket I decided to take a bit of a ‘forgiveness is better than permission’ approach to travel.”

Photo courtesy of Billy Warden

And what travels: Ireland, Switzerland, Puerto Rico, Costa Rica – where he scrambled to filter the chirps of exotic birds out of his work calls – Colorado, Oregon and North Carolina, where he was born and bred.

The twenty-something I’m calling Marco – after the famed explorer immortalized in the swimming pool game – took COVID and the collapse of the traditional white collar workplace as a call to adventure. An invitation not to bunker down, but to journey out.

What he and others discovered about this achingly finite resource called life is challenging ages-old perceptions about how and why we work. CEOs are vexed. Usually smooth-talking consultants are unsure. And pundits are frothing overtime about ‘balance,’ ‘motivation’ and ‘Quiet Quitting.’

Between globetrotting exploits, he dropped by GBW‘s outdoor lounge for this revealing chat about life and work and what corporate America doesn’t seem to get about each:

  • What kind of work do you do and what kind of company were you working with during your remote work wanderings? 

At the beginning of the pandemic I was working for a large tech company that sold core financials and operational systems to all sorts of “Real Economy” businesses. I was focused on convincing wholesale distributors across our customer base to invest in cloud Enterprise Resource Planning systems instead of hosting software they already owned on their own servers.

  • With millions hunkering down in fear during the pandemic, what got you thinking it was a good time to go full-on globetrotter? 

It’s hard to describe the unique crushing apocalyptic feel of New York City in March and April of 2020. Over the next 2 weeks everything goes into total shutdown and I’m stuck in my shoe-boxed sized apartment with 2 roommates. We’re hearing about morgues popping up in Central Park. We’re wiping down our groceries.

It’s also 45 days before our fiscal year ends at my company and I’m supposed to be having the quarter of my life. I have $850K in deals I’m trying to bring in and my yearly quota is around $800K, but suddenly all of these deals are in jeopardy because the economy is crashing to a halt and all the businesses stop spending money. At the same time both my roommates (one in finance and one in tech) get laid off. So I’m sitting in our living room on calls for 10 hours a day trying to rescue all of these deals, and my roommates are sitting around shell-shocked and not knowing what they are going to do.

After a few months of this if you had the chance to go somewhere to just get away for a while you took it.

  • So where have you set up temporary headquarters? 

The first place I went was Ireland. It was one of maybe 3 countries in the EU that had not totally shut its borders. I’d been dating an Irish girl in a complex long distance situation for close to 2 years. In July it looked like Ireland’s borders might close and with that who knew when we might see eacother again. So I packed a bag and bought a flight and went.

My girlfriend and I got an airbnb on the west coast near Lahinge which is the best surfing spot in Ireland. I would wake up in the morning and drive down to the sea and surf until about 12pm, then make it back to be online for work at 9am New York time. Work until about 10pm and then go to sleep pretty soon after that. On the weekends we went on long drives and hikes around The Burren and the Cliffs of Moher, and I was suddenly just in this utter peace.

There was this distinct  feeling of purifying. Like having finally fully washed your hair and maybe a little bit of your brain.

Diving on the job. (Photo courtesy of Billy Warden)

  • And that was just the start? What kind of adventures did you dive into – and how did you make it work with the daily career grind? 

I left Ireland and spent the end of the summer with friends in New York. In January 2021 I went out to a small town called Winter Park, Colorado. I asked my work for 7 days off but in half days – so I would start at 6:30 mountain time and be done by 10am mountain time. Then I spent the rest of the day skiing.

I’m following Colorado natives down the steepest tree-filled parts of the mountain at breakneck speeds, and every day I was working at my absolute peak to keep up while not dying. Skiing like that introduces you to a new level of focus and eventually self-confidence.

At the same time some friends of mine from New York who had corporate jobs with American Express and YouTube had “taken up residence” in Puerto Rico  – so on February 1st (without telling anyone from work) I went and joined them. The time zone is 1 hour ahead of eastern so we woke up every morning and went surfing. There’s a spot called La Ocho because it’s an 8 minute paddle out, and your back absolutely burns by the time you get to the line-up.

After surfing, I worked from our Airbnb taking calls in front of a white background that was calculated to look as much as possible like my New York apartment, but I was getting very tan and there was no way to justify that in New York in February. Not to mention the incessant sound of tropical birds that surrounded our Airbnb. I researched the possibility of noise canceling machine learning programs, but to no avail.

I was planning on going back to New York in March, but with COVID winter still looming the Colorado crew welcomed me back. I got a desk in the local coworking space and would work there from 6am – 2pm mountain time.

We had decided to run a 50 mile ultra-marathon in Oregon. After this I flew to the little jungle town of Nosara, Costa Rica for a break from work. I spent the days surfing in a small beach called Playa Azul where huge sea turtles would surface next to you as you paddled out.

  • How did your employer react to your travels and far away-ness? 

I was performing exceptionally well against my Sales goals at this time. I was the number one Account Manager at my company 2 fiscal years in a row, and with that in my pocket I decided to take a bit of a “Forgiveness is better than permission” approach to travel.

One day the VP two levels above my boss called me to talk about a deal and innocently asked  if I was still in New York. I wasn’t going to lie so I told him I was in Ireland.. He stuttered and said as long as I was working it didn’t matter too much.. But then my boss pinged me the next day panicked and told me to let him know when I planned on coming back.

They never found out I was in Puerto Rico despite the sunburn, and somehow on my last week there during an informational interview with the boss of the Field Account Executive team I was offered a big promotion on the spot.

  • Did you ever get the sense your employer didn’t trust you? 

I never felt specifically distrusted because of my travels, but after being 200% of quota I was still being reprimanded if I wasn’t making enough cold calls during the day and this really started affecting my job satisfaction.

  • Do you find that being away from the office, being someplace new and exciting made you more creative, inspired? That it made your work better? 

Initially when I left the office I was much more productive. I used to commute into the office to sit next to 5 or 6 guys all talking about football loudly behind me while I tried to ignore them and talk with customers. Now I did yoga in the morning, went on a run at lunch, and spent the rest of the day focused and closing deals. I brought in $2.24M in annual recurring revenue to my company in 2020.

But once I realized that this cycle was just going to intensely repeat forever, and that I didn’t care about being #1 sales guy I just lost the steam to keep doing it.

In contrast my travels were an exceptional amount of hard work towards things that I love. My friends in Colorado pushed me to a new level of fitness and grit that I had never imagined. Skiing up a steep mountain face, running uphill in the snow, boot-packing up peaks at high altitude. These things are all immensely hard, and have no reward other than the activity itself, (and mayne one gorgeous ski-run down,) but we pursued them doggedly with incredible satisfaction.

Running 50 miles in the Oregon Mountains is technically “harder” than any possible day in the office. Paddling out through big waves in Costa Rica takes more resolve and grit, digging and “end-of-your-rope” performance than any meeting or deliverable I have ever encountered, and it doesn’t pay anything.

Closing a deal or getting a commission payment has never given me any of these feelings of satisfaction or pride.

  •  When you’re in an exotic location, how many hours a day do you actually work on the stuff for which you’re being paid by your faraway employer? 

At least a full 10 hours if I am committed to the cause. As few as possible if I am not.

  • Did you ever get the sense that folks back at the office were jealous of what you were doing?

I didn’t tell them but I remember having a sense of general amazement that no one else was doing what I was doing. I would get back to my computer from a morning surfing in Ireland and my teammates would talk about how “Quarantine” was so boring in upstate New York or Long Island or St. Paul Minnesota and wondering when things would get back to normal and bars would open back up.

Those who did find out about my travels eventually either expressed amazement and excitement or incredulity, and almost a puritan aversion, like we were having too much fun and that spending Friday night drinking cocktails in old San Juan, and Saturday on a gleaming beach off of Culebra meant you couldn’t possibly be working hard during the week.

The bizarre thing is that if I’m able to spend my time outside of the office in dazzling beauty, I’ll work extraordinarily hard while I’m in the office in order to insure that.

Photo courtesy of Billy Warden

  • Malcolm Gladwell caused a stir after pronouncing that remote work is bad–for society, for companies, and for the people doing it: “It’s not in your best interest to work at home. I know it’s a hassle to come to the office. But if you’re just sitting in your pajamas in your bedroom, is that the work life you want to live? If we don’t feel like we’re part of something important, what’s the point? If it’s just a paycheck, then what have you reduced your life to?” But it sounds like you were up to much more than wearing pajamas all day and found some VERY interesting things to be part of? 

I think that Malcolm Gladwell is absolutely correct about his underlying premise and is probably right to say it. I believe that Malcolm Gladwell is smart enough to understand that his statement applies to remote work, but isn’t really about remote work.

If your work life consists of staring at a screen and working on tasks that you have little connection to then you are going to be bored and unfulfilled no matter your setting. Before Covid I sat in a large room full of people wearing a collared shirt and slacks and stared at a screen. I spent 1.5 hours a day commuting to get to the office where someone could make sure I was working.

Any reasonable person who believes that the world is a beautiful place with an ounce of life left in them should hope to minimize the amount of time that they sit in a room performing tasks without purpose, whether it’s a crusty office in Columbus or a bedroom in Bali.

People have called out Gladwell for hypocrisy since he works from coffee shops or other “non-office” locations, but they are missing the point. His statement is not about location, but about people accepting that they will not go out and engage with the world in a meaningful way because it is a “hassle.”

Some executives might lick their lips and say “See you need to get back in the office” but they have missed the incredible charge that Gladwell’s statement gives to them. They need to provide work worth coming into the office for.

You might say “Get Real, it’d be nice if we could all paint or sell ice cream or think fun thoughts for a living, but that’s just not how the world is. Stop dreaming and get back to work.” The world is tough and we work for a lot more than purpose and many people are seeking simply to have work that feeds and clothes them.

However, I have been in the corporate world long enough to know that our current situation is not “optimized”. I have seen bright, charismatic, passionate people crushed by the boringest of managers who cared about them solely performing as many repetitive tasks as possible so that they would have a high number of completed tasks to show an executive.

I have met executives whose spouses divorce them and children do not know them, as they rush from room to room passionately reciting a script whose words mean nothing to them. They do not even care if their promises are true as long as they end up with more money in their pocket.

Everyone is building and building and selling and selling, but very few of them care at all if what they are building is good.

This isn’t about coming into the office or staying at home. It’s about treating your life and the world as if they matter, and refusing to sit on the sidelines. This also isn’t just about your own life, it’s about working towards a world worth living in.

  • A lot of executives are angst-ing about how to get folks back to the office. Should they be concerned? What are they missing in the way they approach this issue? 

Making people come into the office will get you a body. Giving someone a mission worth pursuing will get you a mind and a soul.

  • What do you and your fellow out-of-the-office adventurers want out of your careers? Out of life? 

I want to be excited by my life and my work while I am in it, and proud of it when I am done with it. I want to approach work with courage, creativity, and integrity. I no longer care about the title that I achieve or how wealthy I am … Today I want to be able to explore the world and live well with people that I love. To the extent that I have financial goals. That’s where they come from.

I’m not some crazy hippy either – I do want a career, but I’d like to build things that I think are valuable and learn about things that fascinate me. After returning to New York I joined a small tech startup as their sales leader. I’ve learned a tremendous amount and worked extraordinarily hard, but I’ve also come to the conclusion that our growth strategy is focused more on “sales” than on reality, and I’ve decided that I’m not interested in a strategy like that even if it’s successful.

So my plan is to pitch a product lead growth strategy for the company that would force us to have integrity and to truly delight our customers. It’s a big shift and I think it’s likely that it will be rejected, but if it is rejected then I’ll quickly be moving on to search for work I can be proud of.

Maybe I won’t make as much money as I do here, but at least I’m not clocking it in.

I want to work with missionaries not mercenaries and I’m slowly gaining the courage to do that.

(Note: This interview has been edited for length and clarity.)