Remote Work Realities: A Deep Dive into the Freedom, Flexibility, and Hidden Challenges

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Written by: Annmarie Borosic

Working remotely is great! You get a lot of freedom, flexibility, and greater opportunity to create the type of work-life balance you enjoy. I can tell you with certainty, there is no other way I will ever work again.

I’ve now been working remotely since around 2015 from the day I left my corporate job and decided to branch out on my own as an Event Planner. The reality then is different from what it is today. Then, my entire living room was a working office. During the busy wedding season, I would spend eight hours in my car driving from site to site and eating on the go. I would work out of restaurants, cafes, hotels, or whatever I was in the mood for that day. I grew accustomed to the chaos and freedom. Today, I have a laptop that I work off of usually on my lap in my living room, or a cafe when I get stir crazy that gets me 20 meters from the Adriatic Sea. I’ve sold my car so I walk everywhere, I take coffee breaks where I can sit at a cafe to sip coffee or grab a quick dinner with friends.

In 2020 when the rest of the world was forced into the remote work life, some people thrived, while others wished to be back around more people in the office and to have more structure. Corporations and companies adapted. It became significantly easier to find jobs in different countries, opportunities we likely wouldn’t have been on our radar had the global shutdown not happened.

Now, things are slowly going back to what it was. I don’t think it will ever be quite as it was in the traditional on-site, in-office work, but companies are trying and many are mandating back-to-office.

The thing I love most about the remote work life is I found more and more people either branched out on their own to do exactly what they wanted or started quitting jobs that no longer aligned with their needs. I love that for all of us!

I find the usual consistent questions come up from those who are hoping to dive into remote work for the first time. With rose-coloured glasses on, going remote seems like the perfect choice. And it is. For some. Here is what I think you need to really understand when diving into your job hunt so you are aware of what you’re truly getting yourself into so that you can decide for yourself what is truly important to you and which path to take.

1. Define Your Career Path

Ask yourself: What skills do I have? What do I love to do? What are my hobbies? How can these crossover skills lead to a new position? Knowing this will prevent wasted time and frustration in your job hunt.

2. Decide on Your Ideal Remote Setup

Are you looking to work locally, within your country, or internationally? Some remote roles are location-specific, while others offer more freedom.

3. Know Company Policies

Check if the company allows remote work only within your city or country or if they support work-from-anywhere options. This can make or break your decision.

4. Ask About Work-From-Anywhere Options

If you’re interested in working from a new country periodically or permanently, find out what the employer will allow. In my experience, many full-time, remote roles allow work-from-anywhere possibilities for one to four months abroad with prior written approval.  

5. Consider the Trade-Offs of a Nomadic Lifestyle

Working from anywhere might mean lower pay, contract work without benefits, and managing your own taxes. Decide what’s worth sacrificing for a flexible lifestyle.

6. Prepare for Instability

Remote work can be unstable, especially as a contractor or freelancer. Many remote roles are with startups or involve self-sourced clients, which may lack the security of traditional employment.

7. Embrace the Freedom

Once you’ve weighed the pros and cons, remote work can bring unmatched freedom and confidence.

8. Set Boundaries for Success

Managing your schedule, life, and work isn’t easy and takes discipline. I’m always fine-tuning my own approach to stay productive.

9. Enjoy the Flexibility and Time Savings

Remote work means saving time on commutes and money on daily expenses. You’ll get hours back in your day to live fully.

I will always advocate for remote work-from-anywhere because the opportunities and life experiences are endless, however, it isn’t for everyone. Can you have the best of both worlds? The money and freedom? You just need to get creative, take a shot on yourself and go for it. It will not be easy in any way, but it is worth it!