Skyping My Team at Midnight in a Tropical Beach Resort: How Work Has Changed For Me

AKA: How Work Has Changed for Me in the Last Two Decades

AKA: You’re Not Really Working Remotely ‘Til You’re Skyping Your Team at Midnight on a Tropical Beach Resort with a Shotgun-Toting Security Guard By Your Side

It was midnight in the open-air dining hall — the only place in the beach resort that had wifi. No lights. No staff. Just the glorious sound of waves crashing on moonlit sands.

I had woken from a short sleep in order to attend the weekly team meeting via Skype. 8:00 AM Pacific meant midnight in the Philippines. But I needed internet. So I walked from the resort villa where my vacationing family slept soundly and crept like a villain to the empty dining area. Cracked open my laptop. No wifi. Uh-oh.

Behind me, someone asked, “Can I help you, sir?”

It was the friendly resort security guard, doing his patrol with a shotgun slung nonchalantly over one shoulder and holding a two-foot-long aluminum flashlight that looked like it could probably beat me senseless if I made a false move.

I said: “Is the wifi turned off at night?”

With very typical Filipino hospitality, he said: “Yes, but no problem, sir. We can turn it on.” He then switched on the hall light, as well as the computer and modem behind the cashier’s desk. Then he pulled out his phone to check Facebook.

I thanked him, connected to Skype, and said hello to my teammates in Mountain View, California and St. Petersburg, Russia and began talking about work, with the waves serving as a lovely background.


Work Like It’s 1994: The Tyranny of the Time Card

At my first corporate job in Metro Manila back in 1994, I had to punch in a time card in the morning when I came into the office and once more when I left for the day. In between, I was writing ad copy for a boutique design/advertising agency, while dressed in full business attire.

We didn’t have computers at our desks. We wrote raffle promo names, product copy, tagline studies, and much more on yellow legal pads using pens. The best ideas were then hand-typed and typically submitted to the client by the account executive, or sometimes (gasp!) faxed over to them.

But while work was being done, the informal conversation in the office inevitably revolved around what each person would do once we clocked out. Almost as if real life only began after five o’ clock.

It was cool working with some real geniuses who were creating outstanding work, but at the same time it was constricting trying to be creative in an environment that elevated clock watching to an art form.


Work Like It’s 2015: Soaking Up the Startup Culture

Contrast that with my current work as a content marketer for a California-based software startup called Wrike. In lieu of shirts and ties, people come for work dressed in the comfiest of T-shirts and jeans. I open my laptop and log in when I’m in the office but I can also work at home, in a nearby McDonalds, or from the city library — anywhere there is an internet connection. Even at distant beach resorts in tropical countries.

In February 2014, I spent 28 days back in the Philippines, attending my sister’s fairytale wedding in an 18th century church. I enjoyed the massive party reception on the beach and took my family to visit relatives all over the country via a series of masochistic airplane rides (a whole other story).

I did this while still submitting articles, completing an ebook, cranking out blog posts (written when everyone was asleep), even attending the weekly “virtual standup” meetings. Which is how I had the surreal encounter with the rifle-toting, Facebook-checking security guard.

That’s when I realized just how much work has changed for me:

  • Free from the tyranny of a punch card that tracks my hours as if it were still the Industrial Revolution, my performance is now based on my output, and on metrics that track how effective my work is in reaching new markets. It isn’t about “putting in the hours” anymore, it’s about getting results.
  • Empowered by collaborative software and Internet connectivity, I can now communicate and collaborate with co-workers wherever I am. The location doesn’t matter as much as the connection.
  • Instead of a workplace where you’re made to feel like management doesn’t trust you to do the work, I’m now employed by a company that assumes I’m a responsible, intelligent adult. Which is why I can work from home as needed. Or take Paid Time Off without jumping through hoops. This is also why I can choose the topics I write about from a pool of ideas — so no one is forced to write about something they don’t find interesting.
    The content team after a game of laser tag against our customer success team.
    The content team after a game of laser tag against our customer success team.
  • Instead of having to tread lightly around office politics and hierarchies, I’m now working in what is essentially a flat organization. This means my CEO’s door is open and accessible if I need to talk with him (typically to ask him to recommend a good science fiction novel). My manager is there to clear any roadblocks in my path.
  • I’m working with colleagues whom I can easily turn to, knowing they will support me and my work as much as I am there to support them with theirs. I work with people whom I can trust won’t steal my ideas and claim them as their own, who will call me out on concepts or verbiage that is unclear, and who will take my ugly rough drafts and edit them to a highly-polished sheen.

The difference is palpable. Because of all these changes, the way I view work and the actual way I work has changed drastically. Instead of dreading Mondays, I look forward to them. Instead of clocking out after 40 hours, utterly relieved, I find myself constantly thinking up new topics to write about. When my toddler wakes up at odd hours needing to be rocked to sleep, I take advantage of the wake up call to get some editing work done for the next day. Instead of looking for ways to skip work like I did in ’94, I’m constantly sneaking in work when I have free time — because I genuinely enjoy it.

It’s strange. It’s liberating. It’s fun.

This is how work should be.


This article was originally posted on LinkedIn Pulse


2 thoughts on “Skyping My Team at Midnight in a Tropical Beach Resort: How Work Has Changed For Me

  1. Read through some of your blog entries – interesting and informative! For some lighthearted musings on corporate life, please feel free to check out my blog at Regards.

    Liked by 1 person

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