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What I Wish I Knew Before Working From Home: Confessions of a Digital Nomad (2024)

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Wondering what I wish I knew before working from home? You’ve come to the right place because I’m ready to share it all with you!

We’ve all fantasized about it – waking up without an alarm, rolling out of bed, and working from the comfort of your couch or a scenic outdoor cafe.

Getting paid while traveling the world, experiencing different cultures, and having complete flexibility over your schedule. Sounds too good to be true, right?

Well as a digital nomad since 2019, I’m here to share all the juicy details – the good, the bad, and the realities you should know before leaping into remote work. Let’s go!

David sitting at a wood table working in Bali. This was taken before I started to wonder What I wish I knew before working from home
David and our son working from our villa in Bali

Productivity’s Ultimate Test

Let’s start with the elephant in the room – without coworkers physically around you and a manager checking if you’re at your desk, how do you actually get anything done?

The lack of structure and accountability is by far the biggest challenge of working from home.

David Cole, Remote Worker since 2008

Gone are those natural prompts and rhythms of an office environment that keep you focused – no more morning meetings, colleagues around you working diligently, set times for lunch breaks, or a manager visibly seeing your attendance and participation.

Instead, it’s just you attempting to create a routine from scratch and sticking to it through sheer discipline and dedication.

What I wish I knew before working from home? You have to be incredibly proactive about scheduling your day, setting deadlines, and holding yourself accountable to make progress.

It’s far too easy to sleep in a bit too long, constantly get sidetracked by household tasks, errands, and noise. I know more than a few remote workers who work at inconsistent and unproductive times because they have no set schedule.

Without self-control, it’s easy to let important projects and deadlines fall through the cracks because no one is explicitly checking in.

Little Man working on his laptop on our balcony in Panama.

Productivity’s Other Nemesis – Temptation

And if self-accountability and creating structure wasn’t tough enough, get ready to stare temptation directly in the face.

I’m not just talking about a fridge full of snacks taunting you around the clock, but really any possible distraction and bad habit your environment enables. That big screen TV silently judging you for not watching it.

Those persistent neighborhood puppers outside, or in my case pets at a house sit, that obviously need pettings and playtime stat. That pile of laundry that definitely can’t sit there any longer.

Maybe you’ll finally rearrange and redecorate that one room like you’ve been meaning to for months. What I wish I knew before working from home? The possibilities for distractions there are truly endless.

Me sitting on a couch at a house sit with two dogs and a cat laying next to or on me.

Self-Motivation is Essential

Being productive when working remotely takes an incredibly strong sense of self-motivation, commitment to deep work sessions, the discipline to stick to a routine, and the skills to create an environment that’s optimized for focus and productivity.

You have to be proactive about planning your days, weeks and months. Setting calendar reminders for projects and deadlines is vital.

Finding ways to reduce distractions by setting boundaries, turning off notifications, or even working somewhere outside your house or apartment.

What I wish I knew before working from home? It’s a constant personal challenge to maintain motivation and avoid the temptations of home.

The Isolation and Loneliness

Another remote work obstacle that often goes unmentioned is isolation and loneliness. While it may not seem like a big deal at first, going days or even weeks without in-person interaction or collaborative working sessions can take a mental toll.

You miss out on those casual conversations, social moments, and team-building experiences that offices organically provide. Core work can certainly get done solo, but group ideation and creativity tend to suffer.

To combat this, I’ve found it’s critical to build in regular social occasions and outings, even if it’s something as simple as working from a coworking space or cafe to be around others.

Connecting with other digital nomads or remote workers in your area can help create a sense of community as well. But these take extra effort – whereas an office has built-in human interaction.

Having my family at home with me is really helpful, too. Usually. My husband is also a remote worker, and even my son homeschools online. So we have a built-in social system, but even we crave connection with other humans besides each other.

Us on a food tour with some digital nomad friends in Mexico.
My family with some friends in Playa del Carmen, Mexico

But…Those Little Joys of Freedom

Okay, enough with the productivity and social doomsday talk. Despite the challenges, working remotely comes with the most incredible perks that make it all worthwhile.

Like needing to take a quick mental break and just going for a walk whenever you darn well please without a million approval steps.

Or having to wrestle and haul something large and bulky like a new appliance or piece of furniture inside – just tackle that bad boy midday without a second thought.

Or squeezing in a workout or mundane household chore like laundry during standard business hours because you have zero commute and can make time for it.

It’s those simple joys and conveniences that make the remote lifestyle pure bliss. Especially when my family is housesitting in a tropical location with a pool. And we can spend our lunch break swimming together!

David doing pool yoga on a remote work lunch break in Mexico
David doing pool yoga on a remote work lunch break in Mexico

A Workspace for the World

And beyond those daily conveniences, the true magic happens when you can take your “office” and work from just about anywhere on Earth.

Some of my family’s personal highlights include logging hours from a serene villa in Bali, a cozy ski cabin during wintertime in Argentina, and boutique hotels across Asia. Getting paid while experiencing the world firsthand – that’s the digital nomad dream!

Be prepared. Taking your work on the road requires careful planning and preparation.

Brodi Cole, Digital Nomad since 2019

You have to map out destinations with reliable high-speed internet and digital nomad-friendly cafes, accommodations, or coworking spaces to base yourself.

Factoring in time differences and aligning schedules with teammates back home takes coordination. Packing up your mobile office and living out of a suitcase for weeks or months at a time is not without its headaches.

It’s a lifestyle of constant transitions – but an amazing one if you crave the novelty and freshness of new surroundings.

Our family skiing in Cerro Cathedral in Argentina
Our family skiing in Cerro Cathedral in Argentina

Final Thoughts on What I Wish I Knew Before Working From Home

At the end of the day, working remotely as a digital nomad comes with its inevitable challenges, but the benefits and unparalleled freedom more than make up for it.

With a little self-discipline, smart planning, commitment to creating productive habits and an optimized work environment, and savvy organizational skills, you too can ditch the corporate grind and embrace the remote work lifestyle.

No more wasteful commutes through rush hour traffic, dealing with office politics and distractions, or being chained to the same desk for 8+ hours a day.

Just you, a laptop, strong wifi, and the opportunity to experience the world while working from wherever your heart (and career) desires most.

So what are you waiting for? If you crave independence, lack of a commute, getting to set your own schedule, and being able to work from a Hawaiian beach one month and a European capital the next, the nomadic lifestyle could be the ultimate dream.

Just be prepared for the struggles of self-discipline, isolation, and constant transitions. But those who conquer the remote work challenges? They get rewarded with a life of unparalleled freedom and adventure. For me, it’s worth the trade-off.

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