4 Reasons Why Remote Work Works for Me

Danny Page
8 min readDec 25, 2018

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Our jobs are supposed to play an important role in defining our lives. Instead of having a job that dictates how I live, working remotely allows me to define my life and work in synergistic way. This is an intro to my story.

It’s a warm Wednesday morning in early spring in Southern California. My alarm sounds at 8am, but I hit the snooze a couple times. Around 830, I’m finally out of bed.

I put on a pot of coffee, and after flipping on the TV and catching up on the morning’s sports news on ESPN, make my way over the my computer. Clad in my pajamas and bathrobe, it’s time to start the work day.

This is the life of the remote worker. Or really, not at all.

I’ve worked exclusively remotely for three years — and partially for nearly a decade — and I’ve rarely started my day in this way. In fact, very few remote workers do.

This is often the external view of the life of a remote worker, according to those that are office-based.

That vision includes lazing around all day in your pajamas, getting around to work when you can, then making an afternoon trip to the gym, before hitting happy hour with your poor friends that actually have to work in an office.

Speaking to local startup leaders about StudySoup — Barcelona, Spain — June 2016

Fortunately, the lifestyle and structure of a remote worker is far different, and must be far more disciplined.

The start of my day — and my life as a remote worker — is basically completely the opposite, as I’ve built a life filled with a level of independent identity and purpose that personally I never could have created while commuting and working in an office.

I work remotely as Senior Head of Operations for StudySoup, an ed-tech startup founded in San Francisco that has no office. Our team of 50+ employees and hundreds more contractors are distributed around the US and around the world.

StudySoup’s remote model and ownership-centric organizational culture have been a natural fit for me, as I’ve grown professionally and personally more than I ever could have imagined in a three-year period.

I’ve leveraged this lifestyle to spend the last few years as a digital nomad, working from more than 20 countries across four continents, and helping drive my company forward while building my professional skillset and advancing my career.

As I talk to friends and colleagues around the world, I try to constantly dissect the negatives and positives of working remotely, and help advise both individual confidantes and entire companies on how to optimize around this evolving organizational model.

Before ever being able to advise another person or organization on a specific strategy or tactic, you must deeply understand yourself and how you relate to it. My relationship with remote work is constantly changing and evolving, as I try to evaluate why remote work works for me.

This journey to understanding what makes remote work effective in any situation is one that will never end in my life, but here are four simple reasons why remote work works for me:

  1. Flexibility (Specifically related to work)

You might classify me as Captain Obvious on point number one, but it’s important to discuss how flexibility positively affects quality of work, as opposed to the flexibility remote work provides to exercise, travel, and take care of personal responsibilities, for example.

While most companies in the United States work 9–6 — or some variation thereof — there is no true edict that only great work can be accomplished between the hours of 9am and 6pm.

In fact, many of the most important products we use on a daily basis were built outside of the traditional work day. Limiting the time at which knowledge workers can think about solving challenging problems to a pre-scripted time and place is counterintuitive to the way the human mind works.

Because of the flexibility provided by working remotely, I am able to put myself in the best possible mental and emotional headspace to solve the challenging issues my organization faces. Unlike the example above, I normally attack the most challenging problems from 6am to 9am when I’m in California and 10am to 1pm when based in my main home in Barcelona.

I find my mind is sharpest at the start of the day, and I always like to get started on solving complex issues about an hour after my day begins.

A snapshot of the structure I use for daily planning and execution.

Frequently, I’ll put in a shorter phase of the day focused on critical thinking after I go to the gym in the late afternoon/early evening. Exercise gives me a level of clarity that I really don’t achieve any time except in the early morning so this “Third wind” is really crucial.

2. Productivity

Needless to say, I am someone that is really easily distracted. For years in my life, and whenever I worked in an office, I felt like the proverbial goldfish, constantly looking out at the shiny things that come into view and tailoring my focus to that.

Whether or not you’re a goldfish like me, offices today — whether traditional or open floor plan — have become bastions of distraction. Whether through interruptive communications, constant noise and visuals, or unexpected meetings, offices are very difficult places to focus.

Why is this such an issue? Because knowledge workers are required to think as critically as they’ve ever been asked to, and solving complex problems takes long periods of deep focus.

Increasing volumes of work on the science of productivity is demonstrating how distractions derail our deep focus, which takes nearly 25 minutes to regain. This has been a constant issue for me and my goldfish attention span.

Working remotely gives you the opportunity to establish complete control over your environment, and build a working and production environment completely devoid of distraction. Creating this distraction-free environment is remarkably liberating when focusing on deep tasks and projects. I put my phone on silent, minimize Slack and the dock on my Macbook, fill up my water bottle and get to work. By putting myself in an environment that I control, I am able to accomplish massive volumes of work in a short period, specifically because I am able to work distraction-free.

I lead a team of more than 50 people in a scrappy ed-tech startup, and without working remotely, I would significantly struggle to be a strong creator, while also being a good manager.

Open offices are visually stimulating and quite trendy, but also can be wildly distracting.

3. Trust

Similar to the experience of many, I have resented multiple bosses I’ve had in the past. They micromanaged, helicoptered, and basically did anything possible to make me feel like they didn’t have faith in the work I would do on my own.

I’ll be the first to admit that I’m my own man. I’m an independent, outgoing, opinionated guy, and I can probably be pretty difficult to manage. I seek constant positive reinforcement and like to work with people that I have a strong camaraderie with. But the most important foundation that I appreciate in a manager is someone that shows they trust me.

In a remote organizational model, managers have to hire people that they can trust, and give them the space to show what they can do without micromanagement. Because company leadership can’t simply pop by someone’s desk twice daily, and check-in on their progress on a specific project, managers have to trust them to complete what has been assigned.

In many ways, this supports not just improved employee satisfaction but also employee output. For too long, managers have focused on optics, looking at a direct report and thinking “they look like they are working hard, so they must be!” The fact is that this is an incredibly elementary way of evaluating daily performance.

Meeting with leadership of the StudySoup support team in Cebu, Philippines.

My performance and output grows exponentially when working for managers that believe in me and trust me, which nearly all managers of remote teams must do. Managers must maintain faith that the people you hired will deliver exceptional results, and if that manager hired the right person, in most cases they will.

This furthermore establishes an interdependent relationship where trust is a key action that facilitates the delivery of exceptional results, only strengthening the relationship between the manager, the employee, and the company as a whole.

4. Travel

This final quality speaks for itself, and is something I’ll discuss at-length in the future. Over the past two and a half years, I’ve worked from more than 20 countries on four continents, and have built professional and personal relationships that will last a lifetime.

The ability to have this freedom is absolutely priceless, and not only allows me to see the world and build global relationships, but it also allows me to do my best work. Despite the chaos that travel can entail, I find an exceptional level of motivation and drive when I arrive in a new environment.

I’ve worked from offices, cowork spaces, cafes, bars, beaches, planes, trains, and even a hospital waiting room (We’ll save that story for another day).

Barcelona has been my central hub abroad over the years, befriending many ascending entrepreneurs in this budding tech hub from my preferred cowork space, BCNewt in Poblenou.

Sunset in Hvar, Croatia — September 2018

ve spent many months in Split, Croatia during these years, working at a cowork space owned by remote work travel operator Remote Year. While this type of structured, group-oriented travel is not my cup of tea, it has been fascinating to meet hundreds of fellow travelers, hear their stories, and understand their motivations for doing what they do.

I’ve built lasting personal and business relationships in Japan, England, Belgium, Poland, and the Ukraine that have shaped me into a more aware and well-rounded individual with a true global perspective.

Currently, I’m splitting my time each year between Barcelona, and my original home in Southern California, living the mediterranean lifestyle I’ve grown accustomed to 8–9 months per year, and spending the “winters” in Santa Barbara area with my family and friends.

I’m incredibly appreciative that I’m able to work for an organization that allows me to choose the life I want to lead, and build my work around that life.

It’s been nearly a decade working remotely, and for these four reasons and plenty more, I’m looking forward to many decades more of productive, location independent work!

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Danny Page
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Entrepreneur and digital nomad committed to an unordinary existence.