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You get to set your own hours, choose your own office space, give yourself a raise and even choose your clients. Freelancing sounds like the dream, right?

Well, it can be, but there are a few things about working for yourself which can make you feel sentimental about your old office cubicle.

If you’ve been freelancing long enough, then this feeling is all too familiar. If not, allow me to present its ugly side along with some practical solutions to help you navigate what can still be a fulfilling career.

Goodbye, Structure; Hello, Chaos

You decide when to wake up, take breaks (if any), the length of your breaks and the intensity of your workday.

All this freedom can be absolutely nerve-wracking for someone used to a specific concrete structure laid out by someone else.

Despite the glaring challenge of readjusting, this remote worker proves it’s possible:

“I was out of a job for a couple of months last year and structured my “work” day as if I was still clocking in. I’d wake up with the rest of the house (working wife and kids in school), get them out the door, go for a run, eat, clean up, then report to work – which was job search activities. I’d stop at noon to eat lunch and play with the dog, then start dinner at 4:30. Unless a hot lead came up late, I’d stay away from the computer in the evening. If I ever get the chance to work from home, I’m definitely using a similar schedule.”


  • Plan for and start your day right. Morning routines alert your brain that it’s time to work and allow you to gather your thoughts before you plunge into the day’s tasks. You can accomplish this by getting dressed as though you were going to the office, set aside time to meditate or make a journal entry and then walk around the block.
  • Chunk your working hours. We are generally wired to focus on any given task for about an hour to an hour and a half. Afterward, we need a 15 to 20-minute break so we can recharge enough to perform highly in the next task. Split your day into four or five 90-minute windows. That way, you will have efficiently carried out four tasks in one workday.

Where Does the Task List End?

The common assumption is that working from home entails plenty of free time for employees to binge-watch their favorite shows while gorging on unlimited snacks.

However, demarcating the workday can prove to be cumbersome. There are always more tasks to be completed and emails to send and/or respond to.

The threshold of productivity also increases significantly due to the preconceived notion that working from home is riddled with laziness. The temptation to keep looking at notifications often fosters feelings of guilt and worry when not attended to.

“Work is infinite. There is always something to be solved – and when you have an office routine, it’s easier to leave what you do at the workplace. When you work from home, your office is where you live. So I’m constantly closing small pending tasks late at night before I go to bed or early in the morning when I really wanted to be reading the news.
“Conrado Lamas, CMO at Carts Guru


  • Set boundaries. With most jobs, there will always be something that needs to get done. This requires you to be disciplined about setting a boundary between your work and personal life. If you intend to work from home for a long time, you have to make it a sustainable lifestyle. That means you’ll need time away from the computer and the stress of work.
  • Take scheduled breaks to recharge. While your calendar may be full of tasks, calls, meetings, and deadlines, it should also include scheduled break periods. Set a time for lunch and other shorter break times. Otherwise, you’ll hinder productivity. Be specific about how you will recharge: a meal, a snack, or a quick walk. Remember, the best recovery is active recovery.

You Don’t Have a Real Job

From the outside looking in, it appears as though you have time for longer lunch breaks as well as impromptu babysitting appointments when in fact the workload could very well be the same.

Although signals such as locked doors, “do not disturb” signs and putting on a pair of headphones could give your family a hint, some family members are unbearably persistent.

This is especially true when kids are involved. As Chris Brantner of “Mr. Cable Cutter” says:

“I have two children, one of whom is 7 and is in elementary school, and one is 17 in high school. I have a home office I work out of but when they are home, they love to randomly come in and say hi or ask for things. I love seeing them (one of the reasons working from home is great is because I get to spend more time with my family). However, it can be difficult to keep enough separation so that I get things done. I’ve had to have talks with them about ‘work time’ and make sure they understand when it’s okay to come knocking on the door and when it’s not.”


  • Create a personalized work schedule. This allows you to complete tasks effectively without the need to cut into your personal or family time and stick to it. This will help you stay on track and means you’re less likely to let both worlds collide. Keeping consistent hours every day will prompt the entire household to fall in step with your routine. 
  • Bring your family into your world. Take some time to educate your family members on both the demanding and fulfilling aspects of your work so they, too, can possibly develop a vested interest in your success or at least understand when you have to work longer.
  • Change location. Intentionally work from a library or a coffee shop once or twice a week so the nature of the importance of your work is cemented within your family members’ minds.

No 10 A.M. Coffee with the Guys in Your Department

“Face-to-face interaction is generally lost, and there’s no substitute for this during some activities that are more collaborative in nature. Video conferencing can sometimes offset this, but it’s not a perfect replacement. Feeling like a cohesive team is more difficult, and some people can never get past that. (Manifesting both with those in the office feeling like remote workers aren’t being part of the team, and remote workers feeling like they aren’t treated like they are real teammates.)” (Source)

Despite the immediate access to your loved ones, a family cannot replace the kind of relationships built between employees working on the same project towards similar goals.

There are office jokes to be cooked up, life experiences to be shared and promotions to be celebrated. Over time, colleagues essentially become your family away from home.

With no one to share frustrations over a work detail with, working from home can easily start to feel like solitary confinement.


  • Try out a shared workspace. They closely mirror a typical office set-up, but the people surrounding you are all working on different projects and you’re not required to talk. However, little chats here and there over time allows you to build work relationships that make up for the colleagues you’re missing out on.
  • Interact with your fellow online colleagues. Chime in on the conversations that take place in the official online meeting place. Sites like Basecamp allow administrators to create group chats for different departments within the organization. Therefore, employees can familiarize themselves with each other throughout the day, interacting from both an official and social perspective.
  • Attend bi-weekly conference calls. Schedule regular conference calls with remote workers from different departments to get an insight into their progress as well as reinforce their knowledge of the company’s mission and objectives. Additionally, an annual retreat for the entire team could be the boost of motivation remote workers require to feel included and stay productive.

Online jobs require a certain level of personal discipline to still meet the same targets one would at a quintessential office job. Tasting success means putting up with a lot of disconcerting scenarios and figuring things out as you go along. However, over time, the benefits outweigh the struggles.

Photo by tirachardz / CC BY

Katrina McKinnon

I'm Katrina McKinnon, founder of McKinnon Group and Small Revolution. I'm using my 20 years' experience in building and operating online businesses to create engaging educational materials that helps others become successful online workers. Find me on LinkedIn and Twitter.

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