The Challenges of Remote Work — and How I Got Over Them
Most people associate remote work with laptops on the beach or hopping on Zoom meetings in their pajamas.
They’re not wrong, but that’s not the full picture, either.
The truth is, working remotely also comes with its own challenges. Since it’s not as “conventional” as traditional work settings, lots of people struggle to get over these hurdles. Beginners may even feel disenchanted about remote work and quit altogether.
Now, before you throw in the towel and give up on your journey, I have some good news: you don’t have to figure things out on your own. Let me share the biggest challenges I encountered when I first started working remotely and impart some tips on how I got over them:
Challenge #1: Distractions
When working from home or in a non-traditional workspace, there can be many distractions that can disrupt productivity, such as children, pets, or household chores. This is especially true in the Philippines as most of us live in multi-generational households or crowded neighborhoods.
I’m sure you’ve heard so many stories of remote workers having to deal with their noisy chickens or their neighbor’s non-stop karaoke!
Eliminating distractions
The best way to deal with distractions is to eliminate them. Something as simple as putting away your phone during work hours or restricting certain apps can already go a long way for your concentration.
In my case, I’ve deleted all social media apps from my phone. A couple of minutes can quickly turn into an hour when you’re just scrolling away on Twitter or Instagram, so it’s best to stay away from them completely while you’re at work.
Investing in a conducive home office space
If you have the ability to create a home office space, go for it. A proper home office can be a conducive environment for concentration. Plus, it helps you set boundaries between your work and home life.
Co-working spaces and quiet cafes can be great options, too!
Dressing up for work— even when you work from home
You might find this funny but I still dress up for work, even when I’m working from home. Instead of wearing my usual pambahay clothes, I put on a nice button-down shirt, a pair of smart pants, and even wear shoes.
This habit conditions my mind that I’m in work mode and helps me become more focused and productive.
Challenge #2: Time management
Without a set schedule, some individuals may struggle with time management. They may find themselves working too much or not enough.
Since I oversee a lot of different things at work, I need to be extra watchful of how I spend my time. Here’s how I manage it:
Using Notion
Tools like Notion have been a huge game-changer for me. In fact, my Notion dashboard acts as my second brain. All my tasks for the day — both professional and personal — are plotted there.
Here’s how I use it:
Instead of going through my Slack and email messages one by one, my assistant plots all the things that need my attention on my Notion dashboard. Then I go through the tasks and check them off. Having everything in one place reduces the cost of context switching and helps me get things done efficiently.
Cutting back on meetings
Meetings can be a huge time-suck, so I also try to minimize plotting them on my calendar. If a conversation can be carried out via email, I’ll keep it there instead of hopping on multiple video calls a day. Having a set workflow like this keeps me productive instead of busy.
Challenge #3: Lack of structure
For some individuals, the lack of structure that comes with remote work can be overwhelming, and they may struggle to create a routine that works for them.
This is why it’s so important to create structures for yourself when working remotely.
Here’s what’s worked for me:
I wake up at the same time every day, around 8am.
I spend an hour reading a book while enjoying my morning cup of joe.
Then I take a shower and dress up for work.
I go through my Notion dashboard for my daily tasks.
Being able to delegate tasks to an executive assistant (EA) has also helped me create solid habits. My EA, Katrice, prepares my Shepherd tasks like client management, team management, and other concerns in one place so that I don’t miss anything.
Related: Interested in working as an executive assistant to CEOs? Apply here.
Challenge #4: Isolation
Working remotely can be isolating for some people who miss the social interaction and collaboration of an office environment. Personally, I love connecting with people in person. I also know others who feel energized when collaborating together versus doing it through apps like Slack or Zoom.
Thankfully, we have a lot of engagement activities at Shepherd to make sure that our remote team still stays connected. Here’s how we got over this challenge:
We empowered engagement leaders in our team
First, we made sure that someone stayed on top of all engagement activities. Pammy was the best person for this job. We recognized her potential early on and gave her the opportunity to build engagement activities. Today, she leads People and Culture at Shepherd.
If you’re leading a remote team, find someone like Pammy to take charge of engagement initiatives. Or if you’re just starting out, make sure to work with a company that values team culture and genuine connections.
Have fun engagement activities throughout the week
Speaking of engagement, one of our staple activities is Fridays At Shepherd. This is where we gather at the end of the week to just chill and hang out online. We have fun games and prizes to encourage participation. In return, the team members get to know each other better and end the week on a high note.
Aside from that, we also have:
various Slack channels
weekly challenges
online clubs
automated daily reminders —
— and special events
These activities connect everyone even when they’re working from different parts of the country.
Organize in-person events
Now that the world is slowly opening up, we’ve planned a couple of in-person events for our team members as well. Once a year, we have a company-wide team-building event featuring fun games and exercises. We also have a Christmas party where we give out prizes and year-end awards for team members.
Related: How we build remote team engagement at Shepherd
Challenge #5: Shifting my mindset
One of the most unexpected challenges that I’ve encountered while working remotely is shifting my mindset from employee to entrepreneur. When you’ve been working as an employee for the longest time like me, this was a huge learning curve.
Most of my remote career involved transitioning from colleague to leader. This meant creating healthy boundaries with the people around me, learning how to communicate tactfully, and making good decisions not just for myself, but for the whole team.
Since I also represent the company, I had to learn how to be mindful of what I put out on social media and how I presented myself to the public. Perception management is tough, but what can I say? It’s par for the course and I’m happy to take on it.
Challenge #6: Working through my insecurities
This last challenge has more to do with being a first-time founder than working remotely, but I thought I should include it here anyway.
When I was starting out as a co-founder, I struggled with a lot of insecurities and imposter syndrome. Maybe it’s because a lot of the founders in my circle were doing this longer than I have — folks like Nick Huber, Shaan Puri, and even Marshall. I couldn’t help but feel like I wasn’t doing enough for the team and the company.
How to get over it
Getting the support I need from my team and co-founder has definitely helped curb the imposter syndrome. I had to realize that I had a great team behind my back who’s ready to support me and complement my skills. If I lack something, I can easily turn to them for help.
Constantly seeking ways to improve myself also helped me combat self-doubt. I enrolled in classes, read books, and most importantly — applied these learnings. There’s no better way to learn than by experience.
Lastly, it pays to look back at your wins! The Shepherd team has come a long way, and we’ve hit a lot of milestones during our journey. Acknowledging these and taking time to celebrate them definitely boosts my confidence as a leader.
There’s nothing quite like remote work
Yes, remote work is challenging. It’s not as easy as taking your laptop to Boracay and sipping cocktails while working on the beach. If you’ve never worked with a remote team before — or have never founded a remote startup, in my case — it can be daunting!
But I truly believe that the benefits of remote work greatly outweigh its costs. For one, it allows you to work from anywhere. It helps you cut back on commuting costs, and spend more time doing what you love. It levels the playing field for so many disadvantaged people. Most of all, remote work gives you an opportunity to grow in ways you never thought possible.
So, if you’re planning to work remotely, be ready to take on these challenges head-on. You’ll be in for quite an adventure!
