What I Wish I’d Known Before Transitioning to Remote Work

Updated: September 2, 2020

By Tyler Enfinger
Activation Associate, Chegg


The other day, during an interview with an employer (yay!), I nervously asked, “Do you feel like this is a role that can be completed remotely?” I was anticipating some pushback or hesitation. Instead, the hiring manager laughed at my question and answered, “Right now, every role can be completed remotely.” 

I quickly remembered that they were right; pretty much everyone is a remote employee right now. But that certainly has not always been the case. Before the craziness of 2020 began, working remotely was a privilege, only given to the most trustworthy of employees. It was also sometimes offered as a benefit, meant to attract better talent to a company. Pretty crazy how fast things have changed, huh? 

Well, right now working remotely is a requirement at most companies—and with that, the ability to work productively while remote is a skill in huge demand.

I made the transition to remote work earlier than most, in fall 2019, and I found that it was more of a challenge than I was expecting. I’m planning on documenting some of my struggles and successes in this multi-article series to try to help you deal with some of the problems that I’ve already dealt with!


Lack of hands-on IT support

Unfortunately, when working remotely, there is no IT desk to walk over to and ask for help. As someone who is extremely familiar and comfortable with tech, I never expected this to be an issue for me. However, over the past year, there were a few occasions where a tech issue was simply above my pay grade, and I could not figure it out for the life of me. And as we all know, describing tech issues in an email or over the phone can be extremely difficult and, at times, frustrating! 

To overcome this, I recommend being very comfortable with Google and standard troubleshooting processes (e.g., turn the device off and on again). You are rarely the only (or first) person to experience a certain problem, so it is normally possible to find the solution to your problem online. When that isn’t possible, some generic tech troubleshooting is always a healthy attempt, and that’s probably what your IT person is going to recommend at first. If you can tell them confidently that you’ve already gone through some basic steps, like restarting your device and disconnecting and reconnecting to the internet, and the problem still persists, it will save both of you some precious time. 

If you’ve given it your best shot, and you aren’t able to solve your own problem (and that’s OK; it happens!), it is time to turn it over to the experts. And it’s important to remember that’s what you’re doing: turning it over to the experts. I’ve learned that while we often don’t exactly understand what the IT person is doing or how they’re doing it, we should do our best to follow instructions because they definitely know more about it than we do. 

When communicating with IT, be clear and concise and try to be as descriptive as possible. “My system will not open this program” helps them a lot more than “It doesn’t work!” Finally, I recommend employing patience. When we have technical difficulties, it often feels like our world is on fire, but IT departments are normally employing some form of triage to identify which problems actually need instant attention.


Attention span problems

This is pretty generic, but it would be misleading to talk about the struggles behind remote work without addressing employers’/managers’ largest concern with allowing employees to work remotely: staying focused. I personally knew that this was going to be a problem for me because I quickly jump from task to task and am heavily connected with my tech (so that I don’t miss notifications). I went into remote work knowing this about myself and have since developed a few strategies that I use to remain focused while working. 

First, I start each day with a list. Personally, I don’t actually write out the list by hand, but I know that writing it down helps a lot of people, so maybe try that. But either way, the list helps me understand exactly what I need to accomplish each day. While sitting in your living room in front of your T.V. with your phone buzzing, it can be easy to forget what you were hoping to accomplish. By having a list, you can always go through it and make sure you’re on track to finish by the end of your day. If you’re a little behind, you know that you have to pick it up. If you’re ahead of schedule, then you know that you can be a little less strict on yourself. 


Keep it real

That brings me to my next point: be realistic. Even in an office, nobody is sitting in one spot, being super productive, for eight hours straight (normally, it is more like 2.5–3 hours of productivity). There are also plenty of studies showing that breaks are beneficial to productivity. What this means to you (and what it meant to me) is that you shouldn’t expect yourself to be sitting in front of your laptop, working nonstop, for eight hours. It can be really easy to get down on yourself and, as a result, overwork yourself, because you don’t think you’re being as productive as you would be in an office, but that’s simply not the case.

To stay focused, I found that my workspace was really important for a few reasons. When I started working remotely, I assigned myself a corner of my house, and I now consider that my workspace. It has been really good for me because I can “go to work” each day. That may sound funny, but your brain truly associates locations with activities like that. Just by sitting in my designated “workspace” (spoiler: it’s a corner of a random couch in my house), I can enter a more focused mindset that makes it easier for me to complete my work. 


Put down the phone

Okay, it’s time to talk about the Voldemort of being productive at home: cell phones. These puppies have gotten so powerful at demanding attention that we can’t live without them. (I really don’t think that I could, but I don’t want to either, so …) I mean, I can barely watch Netflix anymore because I’m so interested in Tik Tok, where content is only 15 seconds long. Let me repeat that: My attention span is so messed up that I cannot focus on a movie or show because my brain thinks it’s supposed to be receiving new, different, and exciting stimuli every 10–15 seconds.

I know; it’s bad. So let me be the first to admit that “put your phone in another room” and “turn your phone off” was absolutely NOT going to be the solution for me. If you’re like me, I’ve found a couple of more advanced strategies to help deal with handling your cell phone as a remote employee. 

I subscribe to the “turn the phone over while working” school of thought because I get a lot of notifications, and if I see them, I will want to explore them/clear them. That being said, I get really anxious when I receive texts and don’t read them because I think to myself, “What if it’s a medical emergency?” or “What if someone is asking me a question and needs a short response?” or something along those lines. I definitely care about those messages, but I am less concerned about Raid: Shadow Legends telling me that my energy is fully restocked. 

My biggest breakthrough involved ringtone/vibration customization. This can take a little time to set up but was monumentally helpful in my journey. We all have a circle of people that we expect texts/calls from frequently. I know who mine are, and you know who yours are. So, I set up very distinct identifiers so that I could easily distinguish if someone/something important was trying to contact me while the phone was turned over. I took it to the next level and made individual ringtones and vibrations for each important contact, but you can simplify it by just making one singular “important” ringtone/vibration and assigning that to anyone who you’d be willing to interrupt your workflow for. 

By employing this strategy, I have severely cut down on any anxiety associated with not checking my phone because I know instantly who is attempting to contact me and whether I need to check my phone right now. This is my single greatest lifehack that I recommend you take the time to implement! 


I spent a lot of time talking about a few things that I wish I had known before transitioning to remote work in this article, but I have quite a few more that I am really excited to share with you in an upcoming article. I also hope to share a few of my successes as a remote employee using some anecdotes from my work. Until then, I hope that you are able to use some of the tips from this article to your advantage. Good luck!