Top 5 Ways To Overcome the Challenges of Working From Home

By: Michael Youngblood, Unsettled Co-founder

Working remotely (aka distributed work, distributed teams, working from home, etc.) has been all of the talk, and for good reason — it’s truly reshaping how we live, work, and travel the world today. It’s built on a foundation of the last 30 years of technology and globalization that’s creating a more distributed world. The hype is real, and there is plenty of it.

And like anything that is hyped up, it’s easy to see the big, transformational perspective of how it’s reshaping the world. At Unsettled, we try to see things with a grain of salt and transparency, even if it’s something we truly believe is radically reshaping how we live and work across our lives today.

We know both the macro and micro level views on working remotely. As a company, we are reshaping how people can make opportunity out of working from home and as a team and a community, we work remotely — from home — wherever that may be from one week to the next. As a leader at the company, the best piece of advice that I give myself around our remote team is that I need to make an effort to connect meaningfully with every team member every other day. Those meaningful connections come out more easily in an in-person setting with lunches, coffee breaks, celebrations, and just making eye contact when someone is having a bad day.

Yes, while there is hype abound about the opportunities in remote work, it doesn’t do anyone any good to not understand the hidden challenges behind it. As distributed work spreads, more of us will be required to overcome the challenges that working from home demands.

As a complete remote team since our founding, Unsettled HQ has learned a thing or two about calling where you work your home, and vice versa. Here are our top 5 challenges and solutions to working from home:

  1. Managing Expectations When Working from Home

If you don’t live alone, there will no doubt be family members, friends, partners, roommates, etc. coming in and out of your workspace during your normal business hours. Frankly, it can be a pain in the ass for two people to share a space designated for home living and working. That person who isn’t working won’t have the same pressure, demands, or needs as you do on a busy day. Do you really have time to work from home, make lunch and clean the dishes afterwards? Or is your housemate going to get annoyed when there’s dirty dishes day after day?  

Solution: The key, like much of life, is to better manage your expectations and those in your home space. Sit down and talk about a schedule and plan together. Make a calendar. When will you have time to do the dishes or clean up? Agree on a policy about when your office door is closed, it’s because you need to focus. Better yet, next time you are staying at a hotel, grab one of those “do not disturb” signs off the doorknob (or DIY!). Or if you don’t have a doorknob (or even if you do) honesty is the best policy. Talk to your cohabitators and initiate “quiet hours”. They probably want you to be as productive when you need to as you do.

  1. Staying Motivated: The Key to Getting Shit Done from Home

Without your productive colleagues surrounding you, it is exponentially easier to sleep in, sneak in a nap, goof off, or hide behind the fact that your boss isn’t around the corner and ready to step into your office any second. We know it far too well.

Solution: Start your day with an appointment. Whether it is at the gym, a bike ride, a work meeting, a breakfast meeting, walking the dog, etc. making an appointment in the morning  forces you to get out of bed, get out of your pyjamas and get your day started.

  1. How to Stay Social (not the media type) When Working from Home

Staring at a computer screen for hours on end in the confines of your home office can get boring and monotonous. There is no physical water cooler to convene around with your coworkers when you need to stretch those legs and rub those eyelids. And this may actually be the most hidden, yet key challenge we face when we work from home.

What we need, in both a work environment and in our lives, is someone to simply spitball with, shoot the shit, or as Unsettled Experience Manager puts it, “in the military, we used to call this ‘war gaming something through.’” Like in life, when we go through our work day, we need to be heard and seen to feel connection, meaning, and satisfaction in our careers. It’s not about being social for the fun of it — it makes us better at what we do and better at who we are.

Solution: Working from a local coffee shop won’t do it. It’s a bandaid fix that makes you feel like by changing environments, you are activating the solution, but you need a peer group to spitball, shoot the shit, or war game things through. Step 1: Cut down on the messaging. Yes, Slack, WhatsApp, and other messaging tools might make it feel like we’re being more efficient in the short run, but when we really need to be heard, seen, and have a voice, it’s better to pick up the phone and shoot the shit. Step 2: In order to shoot the shit, one must have permission to take breaks that are social in nature. Hard to do when you work from home as all of your breaks seem to be…by yourself. Make virtual water coolers! At Unsettled, we’ve held virtual happy hours, virtual lunches, live cooking shows led by our team, and just turning on the camera while working to hangout via camera as we work. Step 3: Get a local peer group outside of your work. You can’t always rely on your friends or family, but if you can build a local group of 5-10 remote workers to spend an afternoon with, you will marvel in joy over how good it feels to turn around and share you ideas, vent, or just laugh during a rough moment.  

  1. Eliminate Distractions Around You

Should I clean the kitchen instead of typing up this proposal? Have the news run in the background to stay informed? Maybe I should check Facebook again while I wait to join this conference call? It’s amazing how easily we can distract ourselves, especially when we are in our physical comfort zones.

Solution: As great of a machine the modern computer is (and these 11 inch machines do allow us to work from home after all), they have as many distractions as benefits. Just as you wouldn’t want the TV running during a worksession, would you want to have a remote right there at your side? Remove the whole distraction, and today that might mean putting limitations and blockers on certain websites that are really nothing but great distractions.

Don’t forget, the whole point of working hard, is to get out of the office so you can play hard! And the play will be so much sweeter because you truly earned it.

  1. Boundaries with Work

When you work from home, it’s more common for the days to bleed into nights, and this isn’t just a problem for you, but it affects those who are now off work and want to be in a sacred space called home. It seems our jobs these days expect us to always be online, but is it because we give them unrestricted access?

Solution: First a warning, to reset boundaries may require that you’ve earned them. Make sure you have worked hard enough and have the political capital to reset boundaries. Also make sure that you didn’t accept a job that requires you to work certain hours. If you took a job that allows you to work from home, but you know the company’s HQ is four time zones to your east, you better expect to have early mornings for the duration of that job because that is on you.

But if you find work just bleeding into all parts of your life for no other reason than the nature of technology or how you have things setup, then there are tools and strategies to help you. Reset expectations by explaining to your team that you will silence communications after a certain hour and on weekends (but consider offering an emergency way to get in touch). Or ask the company to pay for a second phone line (it’ll probably cost them  $25/month) and download all of your work apps to a different phone. Yes, this was popular a decade ago, but that phone can be turned off while you might keep your personal phone on after hours and on weekends.

Whatever you do, there’s a tool and a trick out there for it. Just make sure that you’ve earned the right to make the change before you do it.

And our most favorite solution to all of the above: We are not biased in the slightest… Unsettled your life…we now offer, one month, two week, and one week retreats in more than a dozen locations! You can probably convince yourself, your boss, your cohabitators (or all of the above), to do one of the three! Reach out to us at to learn more about shaking up your routine with us.  


Unsettled is a global community for those who value meaningful human connection. 

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