/ Remote Insights

Not All Remote Jobs Are Equal

When I began working remotely full-time in 2015, years of occasional freelancing had skewed my expectations. I'd become convinced life would be greener if I were only freed from the shackles of the office.

I was right. Kind of.

I've long had issues with the traditional office environment. I'm a big believer that in the age of cloud storage and superfast fibre internet connections the conventional office is all but dead and buried.

Before I made the leap to go remote, I worked from a 15-inch MacBook Pro that I'd cart to and from the company HQ on a daily basis.

I was crammed into the corner of a tiny office from 8:30am 'til 5pm. At at the end of the day, I commuted home with what seemed like the entire population of Kent. By 7:30pm I was back at my laptop, catching up on the work I couldn't do because I'd been distracted by gossip and cake—always with the cake. 🍰

I'm with Jake on this. The commuting time alone makes remote work an easy, logical justification.

For all my faults, I can say I have an occasional bout of vivid self-awareness.

During one of my evening catch-up sessions, I had an epiphany and realised I was far more productive working from home. In fact, I was more productive every time I worked from home.

Proofreading and writing took a fraction of the time. As did editing videos or coding landing pages.

This, I believe, was because I could zone in and just do the work.

I meditated on this—which is to say I thought about it a few times over the course of the next few weeks but did very little about it. It niggled at me. Every time I felt slow or was distracted in the office, the knowledge that I could be a much better worker away from the office reared its enticing head.

Before long, I was itching to see if working from home was as wonderful as I thought. As luck would have it, a freelance client was also looking to scale up their content delivery, so I jumped at the chance.

In an instant—actually 30-days, after serving a required notice period—I was free.

Up to the point of being able to explore remote work, I guess that's a pretty standard story. As a traditional worker, it's easy to convince yourself that a non-traditional setup—like remote work—is far better than that of your regular office.

Things are often thought of in extremes, and the unknown is no exception. Romanticised or chastised, but rarely balanced.

It doesn't help when you see Instagram accounts of self-proclaimed digital nomads brimming with perfect panoramas and inspiring life-quotes.

This was more than simple pining or wanderlust, though. While I admire those who do, I didn't have a hankering to go backpacking around South-East Asia with only my laptop and a rucksack. This was simple, unabashed disenchantment with the traditional office, a desire to make a change, and the support to make it happen.

In August 2015 I took the plunge and began fumbling my way through remote work as a full-time freelancer. It didn't take long for me to realise that not all remote work is the same.

Freelance vs. Self-employment vs. Employed Remote

In hindsight, my first mistake was rushing into full-time freelancing without considering what that entailed, or what my client was looking for.

I saw the opportunity to go remote and I charged in. Go big or go home, right?

Between the work they were promising and the 2 much smaller clients I had on the side, I could just about scrape together a decent living each month. It worked, at least for a few months.

In other posts I've spoken about expectation management. In this case, I'd failed to define my own expectations or consider what I wanted beyond "work from home".

As I see it, there are 3 main categories of employment that lend themselves to remote work well. I'm sure there are more, and there are no doubt variations and specifics within each, but this is my party, and I’ll write what I want to. 🎉


The 3 types of remote employment

Traditional freelancing

Freelancing isn't a new way to work. People have been freelancing for decades.

For me, working remotely as a freelancer felt about the farthest I could get from the traditional work paradigm.

You work for multiple clients, usually on an ad-hoc or fixed-term basis. There is a quick turn-around between clients. Sometimes you're asked to work from an office, but you can make a good living from 100% remote freelancing.

A good example is in journalism. Many journalists are not restricted to a single publication but can pitch whoever they want.

The main downside is limited job security. There's no guarantee of work, and freelancer agreements are flimsy. Should a client wish to drop you, they can and often do so pretty quickly.

Self-Employed Retainer

Being self-employed isn't new either. In the context of remote work, though, self-employment is a popular solution for remote employers. Particularly startups, who employ a global workforce.

While there's a lot of crossover between freelancing and self-employment—if you freelance you're self-employed, after all—what I mean by self-employment in this context is working on a contract for a single company.

These contracts are closer to permanent employment contracts, but the employer's responsibilities are lessened (unless they're expressed within the contract).

The benefit is that work is guaranteed so long as the agreement is upheld. The main downside is contracts are still very flimsy and not easy to support. There are no necessary protections for an employee, despite the full-time commitment.

That's not even counting the legal ramifications for the employer.

Permanent Remote Employee

This is the holy grail of remote work opportunities, in my opinion.

One of the main benefits of remote working for employers is access to a global workforce. However, due to the variation in employment laws across the world, permanent employment opportunities as a remote worker are rare to find.

Typically these are traditional "work-from-home" sales-type roles that require some form of travel and a commission-based salary. That said, more and more startups and forward-thinking companies are navigating their way through this structure, which is reassuring.

The downside—if you can call it that—is you are beholden to a boss once more. So while you might have the freedom to work from wherever you want, there are still often strict policies in place regarding things like working hours.

There is also often confusion around stuff like office essentials, such as stationery and equipment which would usually be supplied by the company, but is difficult to manage in a remote scenario.


I'd intended to foray into a freelance arrangement. I wanted to experience the ultimate freedom that freelancing brings. I wanted to be my own boss, manage my own workload, and take whatever time off I wanted.

Alas, my now somewhat demanding clients had other ideas.

My biggest client began to request more of me. More than I'd expected or anticipated—though really no more than we'd agreed.

As the workload increased at a steady pace, I found myself struggling. It got to the point where I was treating my biggest client as a full-time employer. It was becoming a self-employed retained role.

If I'm honest, I panicked. Anyone in their right mind would have felt lucky to have a client willing to give them regular work at a decent wage.

But I didn't know what I was doing.

I found it hard to juggle the workload between my big client and the smaller ones. My worst fear was letting clients down or having to break a commitment.

I had a tough choice to make: Fire the smaller clients and accept what was more or less a full-time job—albeit on a significantly reduced wage to that which I'd become accustomed. Or fire the big client and try to make up the shortfall by recruiting a few more smaller new ones.

Such naivety.

I hadn't anticipated being in that position, and I found it hard to see the best way forward. With the opportunity of a do-over, I'd handle it a lot differently.

As it was, I opted to focus on bringing on a couple of smaller clients and get some full-time freelance experience. This meant my arrangement with the big client came to an end. A couple of months and many failed CloudPeeps pitches later, regret set in.

To be a freelancer, you have to be willing to take the times of low cash flow along with the good times. "Peaks and troughs" was a phrase bandied around a lot whenever I sought reassurance from other freelancers.

I like peaks. I hate troughs. In fact, I found troughs very hard to deal with.

It soon became apparent that outright freelancing was not the remote life for me.

Sure, freelancing offered the freedom I was after. But I wasn't built for the volatility, and it relied heavily on a regular pitching cycle. I didn't have the financial backing to not worry about whether I had a client that month.

After letting the opportunity for full-time remote work pass me by—and knowing I would never make it as a proper full-time freelancer—I worked on finding a client on a self-employed retainer. After a few months, I found a great role and began working with a client from Finland.

Seven or eight months in and cracks began to show in what was a pretty fantastic setup. The company was great. The team was excellent. But something was missing.

Job security.

It actually came about because I'd begun thinking about mortgages. Turns out unless you have a stable work history and a secure future promise of income, they won't give you a penny. Who knew?

Apparently everyone knew. Everyone but me.

We had a contract. It was as "legally binding" as any contract ever is. But there were no protections for me as an employee. If they decided to cut, run, and ghost me, I had no recourse. đź‘»

Sure I could take them to a small claims court, but an international case between a limited company and a self-employed freelancer? Solicitor fees alone would have destroyed me.

So I searched for another role and agreed to part ways at the end of my contract. The irony is it was the next self-employed retainer, this time with a UK company, that ended badly—a story we will save for another day.

I began to lose hope in the remote system. Freelancing relied on being everything from a sales pro to a customer service agent. Self-employed retainers were flimsy in the remote context and offered no real protection. And fully employed remote roles were as rare as unicorn shit. 🦄

I must come across as irritating, picky and no doubt privileged.

I know people would walk through fire to get a glimpse into the remote life. Here I am belittling the whole thing.

The truth is, because I'd already made the drastic leap to a remote life, I didn't want to settle.

I had built up this idea of a remote work utopia. The kind of life you see on Instagram.

The sort of thing people Vlog about. Seemingly able to scale Machu Picchu at the same time as building disruptive apps and SaaS platforms.

I wanted that freedom.

Like I said before, I didn't actually want to climb Machu Picchu. I didn't have the desire to travel the world. But I wanted the freedom to do it.

And out of nowhere—ok more like a few months of back and forth—I found that freedom, in the shape of HelpDocs' bright pink heart mark.


When I started this journey into remote work I didn't know what to expect. All I knew was that I wanted more freedom and the autonomy that I was sure a remote work life could offer.

But remote life isn't like the vlogs and grams show. It's tough.

The hardest part isn't communication. It's not a lack of culture—which is totally not a thing, the best teams I've worked with have been since going remote.

It's not even loneliness.

The hardest part about remote work is the same as with any employment. Finding the right opportunity for your expectations, and the right company to support you in your work.

Not All Remote Jobs Are Equal
Share this