9 Biggest Challenges Of Working Online + How To Conquer Them

To work online from a remote place is the millennials dream! You don’t need to speak to anyone in person, you don’t even need to get out of your pyjamas.

It’s alluring for us introverts… Working online promises us the freedom to perform on our own terms, with plenty of time to have a cup of tea and do our laundry in between.

But it isn’t all rainbows… There are still challenges involved in working online which might make you think twice about starting.

For example: Isolation, digital eye strain, productivity, mental health and time management are some of the most common challenges of remote working.

Finding work life balance is a challenge in itself.

We’ll go through the 9 biggest challenges that remote workers face, along with the most effective strategies to conquer them. We have been working remotely for over 5 years so we have needed to work on these challenges multiple times!

Whether you’re a seasoned remote professional, online business owner or totally new to the world of online work, buckle up as we dive into the 9 challenges and solutions for a successful online work journey:

Key takeaways

  • To truly thrive while working online, you must have a strong “why” that goes beyond.
  • Improve your work environment to stay focussed in the face of distractions.
  • Put your goals at the forefront, get your tasks done and then SWITCH off and relax
  • Work on skills like productivity and time management to stay on top of your tasks without encroaching on your personal life.
  • Be proactive with your communication to avoid misunderstandings and help with your career growth.
  • Don’t forget to take care of your mental and physical health – the lack of face-to-face contact and movement can greatly affect your well-being.
  • Have a hobby! Travel often and rest your eyes multiple times a day.

We fund our travels by building and renovating websites! This course taught us EXACTLY how to do that: The Digital Investors Program.

1) Isolation and loneliness

In most regular office settings, you have co-workers around you, opportunities to chat during breaks, and team gatherings that give a sense of community. These foundations provide emotional support, promoting overall well-being and connection.

This is challenging to recreate when working remotely. Unless you are part of a coworking space or some communities online, you will find yourself feel an empty feeling on occasion, that sinking feeling of loneliness.

The physical distance and time zone differences make it difficult to connect with online team members on a personal level, which can lead to feelings of isolation and disconnection.

It’s so important you make an effort to make friends on the road.

Moreover, the lack of face-to-face interactions can hinder effective communication, leading to misunderstandings and a sense of detachment from the team.

This isolation can take a toll on your mental well-being and sense of community, potentially affecting motivation and overall job satisfaction.

How to overcome isolation and loneliness:

  • Stay connected with your team and colleagues through video calls, instant messaging, virtual meetings, etc.
  • Don’t totally hermit, just because you work online you can still have community at the coffee shop, fitness centre or park.
  • If you travel full time like us in Australia get an Anytime Fitness gym membership it’s a game changer!
  • Celebrate birthdays and milestones together through messaging and gifts.
  • Make a plan to meet your online co-workers in person on your next holiday
  • Consider having online meetups where you have a drink and catch up rather than only chatting work
  • Consider joining an online community or professional network related to your field.
  • If you crave the energy of a shared workspace, consider joining co-working spaces, even just go for a day
  • Keep in regular contact with your friends/family and get on calls with them once a week
  • Make future plans to connect for upcoming events, networking and catch ups

Travelling and working full-time can get quite lonely. You have to make an effort to reach out and meet new people and friends. Instagram is great for this. We have connected with so many like-minded people.

S&C Travel Tip

2) Establish a productive work environment

Working from home can be a double-edged sword when it comes to productivity. You have the freedom to design your workspace, but distractions lurk around every corner.

Traditional work environments have the advantage of a predetermined layout – you go to the same office every day, which establishes a routine. Plus with your manager breathing down your neck it’s easy for your brain to get into “work mode.”

This can be challenging to achieve at home. You can find yourself working all the time or not wanting to work at all, not knowing how to set boundaries between your job and rest.

You can easily get distracted by family responsibilities, chores, or even the temptation of the TV next room, leaving your work tasks to the last minute.

Two people standing at the top of Frenchman Peak in Esperance, Western Australia
Balance is the key, have clear boundaries between work and play and stick with them

How to improve your productivity as a remote worker:

  • Create a dedicated workspace that is free from distractions, preferably a separate room or a quiet corner in your home. This creates a psychological distinction between work and leisure areas.
  • Establish a routine similar to a typical workday, including designated work hours and breaks.
  • Set clear boundaries between work and leisure time and stick to them
  • If you can, introduce screen free weekends. This will have excellent results in improving your mental and physical health.
  • On work days, it’s important to stop in the afternoon and switch to relaxation mode! Take regular breaks throughout the work day to rest your eyes and move your body.

3) Health issues

Working online means a lot of sitting down and staring at a screen. An important aspect of good health is to regularly move your body.

This can become a problem if you do not manage it.

Sitting for long hours at a desk that might not be set up properly (cafes, caravan chairs etc) can cause problems like back pain, neck strain, eye strain, and mental challenges.

Plus, with the fridge nearby and uber eats sending you notifications, it’s tempting to grab anything and everything, instead of the usual meal planning that often comes in a traditional office setting.

  • Clean your space and get prepared on the weekend just like a usual job. You don’t want to wake up on Monday to a messy house and no plan.
  • Plan your week. Have select days and times for working (we do Monday – Thursday)
  • Make sure you know where you will work the day before if you are travelling. Plan ahead.
  • Take short and regular breaks throughout your workday. Stand up, stretch, and move around to give your body a break from sitting.
  • Incorporate physical activity into your daily routine. Take a walk, do some stretches, or follow an online workout routine.
  • Plan healthy and nourishing meals and snacks ahead for when hunger strikes.
  • Drink plenty of water throughout the day. Proper hydration also helps you stay focused and alert.
  • Ensure you get enough quality sleep each night.

4) Time management

Online work allows you to choose when and where you work, which can be both a blessing and a curse.

The lack of set working hours and the comfort of home can lead to distractions and procrastination. Without a clear schedule and routine, it becomes easy to lose track of time and productivity.

Moreover, the blurring lines between work and personal life can lead to overworking or not dedicating enough time to essential tasks.

Poor time management can result in missed deadlines, decreased productivity, and increased stress, negatively impacting your overall work performance.

How to improve your time management skills:

  • Prioritise tasks. Focus on completing high-priority items first to ensure critical work is done on time.
  • Use time management techniques, like the Pomodoro Technique.
  • Identify potential distractions in your remote work environment and minimise them, e.g. turn off social media notifications, or let your housemates know when you need uninterrupted work time.
  • Set achievable goals for each day or week. Breaking larger tasks into smaller, manageable chunks can make them less overwhelming and easier to complete.
  • Use productivity tools and apps to help manage your time effectively, like task organizers, project management software, and time-tracking apps.

5) Working while travelling

A perk of working online is the ability to travel and work! But juggling work tasks with sightseeing or dealing with travel logistics can be a challenge.

You need to adjust to new surroundings, different time zones, languages, unpredictable internet connections, plus all of this while maintaining productivity.

Also, travelling is very exciting, and it’s easy to get distracted by the attractions and activities around you. Staying focused on work when there’s so much to explore requires a great deal of self-discipline.

Not to mention finding a suitable work environment while on the move. Coffee shops and public spaces might not always offer the ideal conditions for focused work.

We use satellite internet (Starlink) to be able to work even in the most remote places

How to make “work and travel” work:

  • Plan your travel itinerary and work schedule in advance (we try to work Monday – Wednesday on the laptop no matter what).
  • Identify reliable internet hotspots, reserve quiet workspaces when possible, and schedule work hours that align with your travel plans.
  • We often will still do a tour mid week so that it isn’t as busy, if we do this we will often trade a day and wokr on the weekend or after hours to catch up
  • Designate specific times for work, but also allow yourself to fully immerse in the culture and enjoy your travels after.
  • Be realistic about your work expectations during your travels.
  • Set achievable goals for each day.
  • Communicate with your team about your availability and potential delays.

6) Lacking a clear “why”

The idea of remote work is appealing, but it isn’t all pros and zero cons – online work has disadvantages, too.

Having a strong “why” that goes beyond the allure of working from home is crucial. You can only show up so many times until you start wondering WHYYY am I doing this?

Figure out what drives you in your work. Understand your WHY it will provide you:

  • A reason to work hard. When building a business there will be times you want to quit.
  • Your WHY will keep you going.
  • Getting clear on your passions and talents will guide you on what niche/topics to focus on
  • Specific goals to work towards. These will be your guide.
  • An easier way to overcome every challenge mentioned below.

A way to do this is by finding what intrinsically motivates you. This sounds like a fancy term, but it means finding the deep-down reason(s) that makes you want to work online.

Perhaps you want to help people by sharing your skills on YouTube, maybe you want to retire your parents or inspire people to create music.

Our intrinsic motivation was to make travel our lifestyle. Working and travelling full-time.

How to find your why and your intrinsic motivation:

Take some time to introspect and identify what drives you. Ask yourself questions like:

  • What are my long-term goals?
  • How can working online help me achieve them?
  • How will remote work contribute to my personal and professional growth?
  • What aspects of building an online business excite me the most?
  • And what aspects excite me the least?
  • What do I read about in my spare time?
  • What do I enjoy doing in my free time?
  • What kind of work tasks make me feel excited?
  • What skills do I have that I’d love to use more often?

Taking the time to answer these questions will help you find a remote setup that connects with your inner self. It will also make it easier for you to overcome the challenges of working online. You’ll see them as bumps on the road towards your end goals.

Having a clear WHY is the single most important thing when working online. This will keep you motivated to sit down and work. When travelling full time you can easily get distracted by all the activities around you.

S&C Travel Tip

7) Communication hurdles

This is one of the biggest challenges when managing remote teams. It’s just not the same communicating online than in person! You’re relying on technology and internet to communicate through emails, video calls, and messages.

Most of the time, communication happens asynchronously. The lack of real-time, face-to-face interaction is prone to misinterpretation, which can lead to confusion or misunderstandings.

Too many times my brain wants to take offence to something innocent, and I need to remind myself of tone. I find myself coming across blunt sometimes! A smiley face goes a long way. 😉

How to improve remote work communication:

  • Be proactive with your updates, any delays that may come up, the next steps you plan to take and so on.
  • Try to be kind, patient and curious rather than allowing your knee jerk reactions to drive you
  • When possible, use video conferencing tools to discuss complex topics, intricate projects, or sensitive matters.
  • Send emails after communications to cement what was discussed so you have a running log of conversation
  • Be clear and concise when sending messages or emails.
  • Schedule regular check-ins with your team.
  • If you’re unsure about something or don’t understand a message, ask for clarification. It’s best to ask and be clear than to make assumptions and get things wrong.
Catching up with friends on the road who also work online full-time.

8) Career advancement opportunities

In a traditional office setting, you have daily face-to-face interactions with colleagues and supervisors, making it easier to showcase your skills and contributions.

However, remote work can limit your visibility within the organisation. You may need to work harder to ensure your accomplishments are recognized, which can give you more opportunities to grow.

You’ll also have to be more proactive regarding your career growth. That means actively seeking networking, mentorship opportunities, etc.

How to ensure your career growth while working remotely:

  • Have regular conversations with your manager about your career goals and performance.
  • Request feedback on your work to identify areas for improvement and growth.
  • Attend virtual conferences and webinars to expand your knowledge and network with professionals from your field.
  • Showcase your achievements through remote work and highlight your adaptability and self-motivation to potential employers.
  • Be open to occasional visits to the office or attending in-person events if possible.

9) Technology glitches

When you work remotely, your computer and internet connection become your lifeline to the outside world. You need them to communicate with your team, attend virtual meetings, and get your work done.

But internet outages or slow connections can disrupt your work and cause delays. Software or app malfunctions might freeze your computer or prevent you from accessing important documents.

How to avoid inevitable technical challenges:

  • Have backup plans in place, such as mobile hotspot devices or alternate internet connections.
  • Keep your software and devices updated to reduce the chances of technical glitches.
  • Learn some basic troubleshooting tricks. Restarting your computer, resetting your router, or clearing your browser cache can often solve common technology issues.

And when the inevitable technology glitch happens, stay calm and be patient. It is an annoying but unavoidable part of remote work.


What are the pros and cons of working remotely?

The pros of working remotely include:

– Flexibility and freedom to set your schedule and work from any location.
– Better work-life balance.
– Save money on transportation and work attire.
– Higher productivity levels (for some remote workers).
– Access to more opportunities worldwide.

The cons of working remotely include:

– Potential isolation, loneliness and disconnection from your coworkers.
– Communication challenges due to asynchronous communication.
– Lower productivity levels, as working from home can be distracting.
– Limited career advancement.
– Technology glitches.

Are people happier working remotely?

Yes, people tend to be happier working remotely (according to a study). However, the level of happiness experienced while working remotely depends on the person.

Some are happier with remote work because of the flexibility, reduced commute, and improved work-life balance.

But it’s the opposite for others, as the feelings of isolation and lack of camaraderie affect their mental health. It can be challenging for them to balance work with leisure time due to the lack of structure.

Ultimately, it’s up to the person. If you haven’t tried it yet and are curious, don’t let the potential challenges of remote work stop you – try it out and see how it feels!

Why is remote work stressful?

Remote work can be stressful due to various factors, including:

– The feeling of isolation is caused by the lack of face-to-face interactions and social support from colleagues.
– Communication challenges, such as misinterpretations and delays.
– The flexibility can blur the lines between work and personal life, leading to difficulties in setting boundaries and avoiding burnout.
– Pressure to prove their productivity.
– Distractions in the home environment.
– Technology glitches.
– Limited career advancement opportunities.

Addressing these challenges through better communication, setting clear boundaries, and creating a productive work environment can lead to a better experience with reduced stress levels.

The bottom line

While remote work offers dozens of benefits and opportunities, it comes with its fair share of challenges. But these shouldn’t deter you from starting your journey!

Understand these challenges and implement the practical solutions mentioned above. That way, you’ll be able to successfully navigate the world of remote work and make the most out of this flexible and rewarding lifestyle.

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