February 4, 2021 / #digitalnomads

A Year as a Digital Nomad: The Things I Miss & Do Not Miss Working in an Office

A Year as a Digital Nomad: The Things I Miss & Do Not Miss Working in an Office

It's been over a year since I started my digital nomad journey. It took me years to decide and finally submitted that resignation paper.

For over 10 years, I worked in an office. It was a difficult decision to leave as it was my sense of identity and my stability.

But the dream of traveling the world without worrying about limited vacation time was stronger.

Excitement and spontaneity finally became more compelling than predictability.

It's been a year so I have reflected on what I miss... and also the things that I do NOT miss. 

This might help you see the reality of being a digital nomad after leaving a corporate career. 

Let me start with the things that I do miss.

The Things That I Miss

1. Stable Internet

Working in an office gives you everything you need so you can get work done and that includes fast and reliable internet.

Internet connectivity is essential in an office so I never had such problems related to connection.

As a digital nomad, you can stay in areas with good internet but not all places can offer you this. There will be times we wanted to stay in a remote place so we can't work during this period.

There are countries like Thailand where internet connection is very reliable almost anywhere! However, countries like the Philippines and Laos would not have strong internet except for a few areas.

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Above: One month in Laos with no stable internet. Not much work done during this time but we were able to travel more!

2. Power Dressing

Some people don't like dressing up and they actually like the idea of being a digital nomad and just wear their summer clothes while working by the beach.

(a typical digital nomad picture but I realized it's difficult to get work done near the beach!)

As for me, I really loved power dressing. I believe dressing up like you mean business actually sets your mind to think that way.

I do not buy expensive clothes but I like having different sets of dresses where I'd look professional.

As a nomad, I can no longer carry as much clothes. I repeat wearing the same clothes until they're worn out. 

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Above: I have one cardigan to look a tiny bit formal if I needed to talk about business. But speaking in front of other nomads doesn't need much formality. I was even barefoot in the above video!

3. Having Friends Nearby

I'm an introvert and made a few friends throughout 10 years of my career.

But those few friends are those I consider true friends.

When I'm having a bad day, it's easy to reach out to a confidant who's just stationed at another desk.

And when I'm having some wins in life, I can share it to them and I know they'll be happy about it.

As a digital nomad, I'm lucky to be traveling with my partner but it can be sad sometimes connecting with people along the way and having to let them go soon.

Knowing you will never see them again.

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Above: I have more dog and cat friends. They're fluffy and won't judge you.

4. Free Trainings & Certifications

Some of the perks you can get working with a company is that they take care of your professional development, and even soft skills.

Some certifications can be costly which some companies pay for if it would be helpful in your job.

As a self-employed nomad, I have to pay for my own trainings. But don't fret, there are several free platforms and paid ones that are affordable. 

For free platforms, I have used Google Digital Garage and LinkedIn Learning and they even provide certificates. I also utilized the free version of Codecademy for the basics of programming. 

Currently, I'm undergoing a paid course to learn email copywriting with Email Underground Intensive and it's sooo worth it!

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Above: The kind of training I get now. My choice. This was a conference about blockchain technology and social media.

5. Not Worrying about Tax Filing & Gov't Contributions

This is something I appreciate being an employee.

You just show up and do your job. You get paid and statutory deductions are automatically applied. Best of all, you just have to sign your tax documents by year end.

Personal tax filing and government contributions can be a headache for freelancers. You have to register yourself and track your variable earnings. Some big freelancers even hire an accountant for this job. 

Photo by Leon Dewiwje on Unsplash

6. Company Benefits

To be honest, I miss the perks I got from my previous employers such as company outings, free food Fridays, after office movie nights...to name a few.

These benefits are low cost but these can keep employee morale, up to some extent.

Most importantly, Health Insurance provided by the employer saved me a lot of pesos and gave me peace of mind.

As a self-employed nomad, I now have to pay for my own travel medical insurance. As I am always moving, a travel insurance is necessary. 

I have written a in-depth review of SafetyWing which is the insurance I chose after extensive research.

Travel Medical Insurance is something you have to pay for yourself as a self-employed nomad so I chose an insurance that is reasonably priced at $40 per 28 days
Travel Medical Insurance is something you have to pay for yourself as a self-employed nomad so I chose an insurance that is reasonably priced at $40 per 28 days

The Things that I DO NOT Miss

1. Dreaded Monday Mornings

A typical 9 to 5 job gives you a weekend break and Sunday always feels the saddest. I always wish I could extend the weekend or hope for public holidays to fall on a Monday.

And as Monday arrives, I wish it was already Friday so I can finally enjoy.

I realized that life shouldn't be this way.

If you also feel this way, then why are you even in that job? Being a digital nomad is not the only answer. It can also be a change in career or employer, a short break... among various interventions. And this is something only you can answer.

As for me, I no longer dread Mondays. In fact, I don't even realize when we've started the weekend. 

2. Setting an Alarm Clock

Working in a 9 to 5 job means you have to follow a schedule. Whether you're working in the morning or at night, you have to wake up at a certain time.

You also need to set a time to prepare so you're even waking up earlier than you're office open hours.

Freelancing as a digital nomad gave me more freedom to work whenever I am more productive.

I love it because I don't feel like I'm forcing anything and this leads to increased efficiency (since I'm not as stressed) and creativity.

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Above: My schedule is now dependent on breakfast time. But a brunch is always an option :)

3. Commute to Work

I was lucky to live near the office in the last few years of my 9 to 5 job. I had to pay a premium for renting in the business district though.

Prior that, I wasted several hours of my life in traffic.

I had colleagues who had it worse and commute at least 3 hours... per way! So that's 6 hours lost time in a day.

They could have worked and earned on a part time job or business with those lost hours. 

As a digital nomad, your work is wherever you are for as long as there's stable internet.

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Above: Sleeper buses - my new kind of commuting.

4. Office Drama

Consider yourself lucky if you haven't encountered office drama.

Working in an office requires teamwork and especially in a very social country like the Philippines where I'm from - "pakikisama" (camaraderie) is extremely important.

If you're an introvert like me, then you're more likely to have a problem with colleagues.

I did my best to work and treat my colleagues right. But just because I'm not like them, or I don't join them in after-office hang outs, then I'm considered an outsider which is fine.

I'm fine being an outsider since I'm an introvert, however, I have often been misunderstood. 

(not all of course, please... if you're my former colleague reading this, it's not about you...I don' like pagpaparinig)

One of the worse thing that I have encountered was "pagpaparinig". I'm not really sure how to translate this. It's when someone gives a remark about you and they make sure you hear it. 

It's a subtle form of bullying.

It's a toxic Filipino behavior, people don't like confrontations so they'd rather do this which even got me depressed (among a lot of other factors in my life).

I had a teammate who always say I'm "maarte" (choosy, picky in a negative way, or just maarte in the way I speak).

Now, I can be maarte and I don't have to go through this BS.


Other forms of toxic culture I have seen are: office gossips, not respecting people's choice to be alone (this maybe common in a Philippine office set up because Filipinos value "pakikisama"), crab mentality and so on.

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No to crab mentality!

5. Office Politics

I never understood promotions. This is coming from someone like me who has worked in the Human Resources and handled Talent Management.

No matter how objective you set the process, promotions aren't always fair. The boss, who are by the way humans, have a strong say on who to promote.

There are fair managers, of course, but I have seen some questionable promotions.

Deny it or not, there is some politics involved. You have to know how to navigate personal and business relationships too.

As a self-employed nomad, I no longer have to stress myself on this process. Waiting year after year just to get disappointed. To feel that I was never enough despite giving it my all.

I'm not bitter because if not for these failures, I wouldn't decide on embarking on this digital nomad journey. I owe it to the managers who never saw my potential.

Not to mention that an employee's salary increase can only go as high.

As a freelancer, your salary (and promotion) depends on how much effort or value you give. You set your salary, not your employer.

6. Limited Vacation Time

My travel time in the past was limited by the amount of time off I can get from my employer. I recall that the longest holiday I got was around 3 weeks.

A typical trip only lasted for 5 days, and I'm lucky if I get to file a leave before my colleagues do on a long weekend.

There was competition on when to file a leave too since there should always be enough headcount in the team daily.

I am now enjoying slow travel. I can stay in a country and get to really immerse myself in their culture.

The only limitation is the visa. 

Final Thoughts

These are my personal opinion and experiences. I am not saying that office life sucks. It does for me to some extent but this is not true for everyone.

I know people who thrive in their 9 to 5 job.

I also want to show the reality of living this digital nomad lifestyle.

There are things I had to give up but these are nothing compared to living the life I dreamt of (personally).

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