The 7 Things You Need To Know About Successfully Working Remotely

Mar 20, 2020
Rebecca Testrake

Alright, so you’re working from home for the first time ever or the first time in a long time. As if a world filled with COVID-19 and a lack of toilet paper wasn’t hectic enough, now you are navigating a new way of working. Maybe this is something you’ve been dreaming of for years, maybe this is your worst nightmare come true. Regardless of how you feel about working from home, though, the question remains: How do you do it?

Working remotely offers up some wonderful benefits: a lack of commute, the ability to work from the comfort of one’s own home, no dress code, and more. “If you’re doing creative work, you can create your own environment to feed your inspiration. Creativity is not something that can be forced. It has to be nurtured,” shares Junior Designer Liam Ramsey. That’s not to say that working remotely is the golden ticket for solving all work challenges, though. Greater freedom can mean lack of immediate accountability. Many wonder how they will maintain productivity or focus without the external structures provided by an in-person office setting.

As an entirely remote company, we at Cantilever realized we have valuable insight to share. I interviewed a handful of team members about what they would suggest to a person new to the working-from-home world, synthesized their responses, and then came up with the following seven tips:

Tip 1. Find Your Ritual: Do whatever it is that you need to do in order to get into the work mindset

Find, develop, and stick to whatever routine you need in order to get yourself into the mindset of being ready for work. This may mean that you get ready for the day by doing things that you don’t strictly need to do because you’re working remotely. Know what works for you and what doesn’t.

  • Do you need a routine?
  • Do you need to get ‘dressed’ for work?
  • Is there a certain location that signifies “I have gone to work now”?

Our Designer and Front-end Developer, JT Fridsma, suggests: “When working from home, try to maintain your normal routine as much as possible. Keep your routine for going to work. It’s tempting to get off track.”

That being said, there is no one-size-fits-all for transitioning into work mode. There are days when my morning commute literally consists of waking up, rolling over, and grabbing my computer from wherever I’ve set it next to the bed. However, I do not have kids to take care of and my schedule is generally more fluid than most. Nikki Munson, our Operations Director also shared with me her secret: “For me, working in sweatpants is ideal. It doesn't bother me to not get fully dressed each morning and makes no impression on my mental state during the work day.” She says of her husband, Parker: “He doesn’t think he’d be able to be productive if he didn’t get up in the morning and get dressed [for work] and have his routine. It all just wraps into knowing yourself. Know what works for you and what doesn’t. A lot of the time, that comes with trial and error. When I first started at Cantilever, it was like, ‘Okay, I’m up and I’m getting ready,’ and then half way through the day I’m switching back into sweatpants because I’m sitting on the couch or something [to work]. So, now I know if I get up in the morning and do my bathroom routine of: wash my face, and do my hair, I don’t feel unproductive wearing sweatpants.”

Conversely, Andrew Heins, our Head of Support has been working remotely for 8 years and offered up his newest tactic: wearing a tie. For Andrew, wearing a tie signifies more than just “being in the office.” With two young children at home, wearing a tie also means “Dad is working.” Once the tie comes off, Dad is ‘home’ from work. This flows nicely into our next tip.

Tip 2. Develop Boundaries: Create and maintain a separation between work and non-work time

Work will no longer be something you can literally leave at the office because the proverbial office will likely be located in your home. Developer Adrienne Travis warns: “If you don’t have boundaries, it’s easy for work to eat the rest of your life.” In order to protect the distinction between your work-life and the rest of your life, it is important that you create and uphold boundaries of where-and-when consists of work activities versus where-and-when you live out the rest of your non-working life.

Additionally, unless you live alone, that interrupting coworker at work will likely be replaced by a partner, kids, roommates, or anyone else who you share your space with. If you have a spot in your home that you can turn into an ‘office,’ that’s ideal. However, many do not have that. That’s okay, too. Suggestions from Cantilever team members include:

  • Find a quiet place to work or have an arrangement with the family of when is work/quiet time and when is play time.
  • Make some kind of ritual or boundary for designating between work-time and space from the rest of your life.
  • If you have a separate computer, designate one as use for work and one for personal use.
  • If you only have one computer, other distinctions between work-mode and life-mode might include:    
  • Use a virtual desktop simulator to create two distinct spaces at the level of your machine.      
  • Set up different user accounts on your computer
  • Use different web browsers when working and not working (IE: Chrome for work and Vivaldi for browsing) 

Work will expand to fill whatever time you give it. So, make sure you don’t feed it more than you actually intend to.

Tip 3. Take Breaks: Go outside sometimes

“Once you do start working from home, it can be isolating. Some people are born for this, but you still need to go outside every once in a while,” states Andrew. Knowing when to stop working will be crucial for your emotional, mental, relational, and physical health. This means that you will need to listen to your body while you are working.

Remember to give yourself breaks because nobody will be there to tell you to do it. Adrienne advises, “Take advantage of the flexibility of remote work. Most people can’t be productive 8 hours in a row — it’s just not possible. So, build breaks (big breaks!) and leisure time into your day. Go outside! Give your brain the space to refresh and reset.” (We talk more about the importance of taking breaks in relation to increasing productivity in our article “Vacation Mode.”)

“When the work day is over, make sure to spend time with those people around you. We are practicing social isolation right now, but it doesn’t hurt to take a walk, spend time with a pet, spend time with family, etc. Make attempts to be social outside of work time because you won’t be social during the time you’re working while you’re working from home,” continues Andrew. Fridsma adds: “When you don’t have a social, face-to-face aspect to your work environment, you need to have a strong social environment on your own time. Otherwise, you can suffer socially and mentally.” Attending to your body’s needs will allow you to better focus on getting that work done.

Tip 4. Communication is Key: Pursue proactive and process-oriented communication

Working from home means that you will no longer be able to poke your head into a coworker’s work space when you have a question (urgent or otherwise). While physical isolation can come in handy for locking into a mindset that allows for deep work, this lack of immediate connectivity presents a need for a new level of intentional communication. That means different things for different companies.

Many (even non-remote) companies already rely on Slack for their back-and-forth communication. This tool can be great for getting immediate responses, but can get overwhelming because it does not filter messages according to importance. At Cantilever, we are an entirely remote company and have an asynchronous setup which has required us to develop different modes of communication and expected response times related to degrees of importance. The general summary of our communication is that we expect a 24 hour response time to direct questions within emails or our cyber office within Basecamp, and immediate responses to texts or phone calls — the latter category which should be reserved for emergencies only. (Our public handbook has an entry on Communication Guidelines that you’re free to read if you’d like to see the specifics of how we break this down).

We also have systems and documentation for communication so that if a person has a question, they can find what they are looking for quickly and easily on their own. Nikki summarizes: “Be extra process-oriented and proactive about communicating. Be mindful and proactive about setting up systems and processes.” JT adds: “These [systems, processes, and communication] need to be clear so that you can have clearly set stages, expectations, and stages for work.”

Finding the new normal regarding communication will likely be one of the biggest adjustments and challenges that you will face. Project Manager Raul Rovira shares this trick that will help you manage your boss during this bumpy time: “Your boss will likely feel like they are losing control over the organization so you’ll need to develop a communication mechanism to say what you’ve done and what you’ve accomplished.” Raul suggests providing a daily highlight. Want to really stand out? Offer a summary of what you’ve accomplished that day and what you anticipate still needing to do. Remember that ritual we mentioned earlier to signify the end of your work day? This is a good way to do it. Taking the extra 5-10 minutes to write up a little report can have a huge payoff in terms of the unnecessary stress that it alleviates.

Tip 5. Time Management & Task Prioritization: Become your own supervisor

Find a schedule and a system that works for you for getting things done. Likely, your job will want to have you maintain a similarity of the hours you worked in the office. However, with the removal of the external accountability that comes with working in an office, you will still need a daily plan, structure, or schedule to motivate yourself. This is even more true if you work asynchronously. Managing your own schedule is a perk of working remotely, but it also requires discipline.

You could say that Raul is an expert on time and task management (well, because he is). While cautioning that “time management is going to be even more of a challenge,” Raul also has some suggestions for helping to manage it:

  • Have a plan for what you will accomplish and when.
  • Your calendar will be helpful here.
  • Keep spaces of time in between scheduled events to allow for coffee or bathroom breaks.

For both time management and project prioritization, you will become more of your own supervisor, determining what to do and when. Create a plan for addressing tasks. This will require that you find a balance between listing the steps of what you need to do in order to accomplish something versus getting caught up in listing the minutia. Having and using the proper tools is crucial for helping you be successful here.

Tip 6. Find Your Tools: Don’t worry — we have some suggestions

Your tools will matter a whole lot more when working remotely than when you are in an office working off the cues of other people. When we say “tools” of course, there are two categories of apps or items that we have in mind:

  • Those that help you as an individual be more productive with a remote focus
  • Collaboration tools (good for remote workers working at remote companies)

You will come to rely on these to keep you on task and in the loop more than you normally would in an in-person office setting. This is because when you are in a remote environment that is removed from other people, you have to rely more on the tools that you have on a day-to-day basis. That coworker who can no longer poke their head into your office to ask you a distracing question? Yeah, they can’t remind you of the meeting that is happening in 3 minutes either.

Your tools are now more important because the other structural work environments are gone, yes. However, Andrew reminds me during our conversation: “The actual tool is less important than keeping on top of what you do.” So, how do you find these all-important tools? Well, here are 3 guidelines we suggest:

  • Don’t be afraid to invest
  • Don’t be afraid to experiment
  • You will likely not find the right one right away. There is no one-size fits all.

Adrienne expounds: “Find tools that work for you, that you can work with. If you don’t get along with the tools, you won’t use them. Even if those aren’t the tools that the rest of your company is using, you’ll still be more productive in taking the time to translate between the one you are using and the one they’re using than working with one that doesn’t work for you.” That being said, we’ve compiled a little list of tools that we like to use either as a company or as individuals. Many of these offer more than just the simple category that they’re listed under, but this is a pretty good starting point at least for getting you familiar with them if this is all new to you:



  • Slack      
  • Zoom
  • Basecamp (We also use this for project management and as our cyber office.)

Time Management:

  • Calendar Apps      
  • Reminder Apps

Task Management:



Tip 7. Expect a Learning Curve: You won’t get this overnight

Keep in mind that the transition to working remotely will not be seamless and your development will be individual to you. During our chat, Adrienne shared with me that she has been working remotely for 20 years and is still “figuring it out.” Andrew compared transitioning to working remotely as being similar to when we graduated from high school (where everything is very structured) into whatever comes next (college, work, etc) where whatever you’re doing is generally less structured. He adds: “You will find that you have more freedom and you will need to navigate that.

“Expect to struggle and be okay with that. Nobody who works from home just gets it immediately. There will be stumbling blocks along the way. It’ll be harder at first and then it’ll get easier as you adjust to the new normal. Don’t expect perfection from yourself or those around you.”

Reflecting on the learning curve, Liam concludes: “The beauty of it is that once you get a hang of it, you can build it to function in a way that works for you.” So, give yourself (and others) grace. This will not be easy at first, but it will get better, and we think it is pretty great.

If you need any tips, feel free to reach out. We at Cantilever are always happy to share with you what we know because we believe in a world where we get better together.

Welcome to remote working!

Header Image by Daria Nepriakhina on Unsplash

Mar 20, 2020
Rebecca Testrake
Edited by
Ty Fujimura

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