Interview with Andrew, a freelance writer who works remotely

Funnily enough, I never intended to freelance remotely full-time. At first, I had found the website Upwork, where you could apply for writing jobs that clients were looking for writers. Thinking it would be a good way to get some side cash here and there, I put in for a few jobs.

Upwork has a simple enough system to apply for jobs, making it easy to apply for a bunch of work at once. Since I had no experience and no ratings, I figured I’d put in for a lot of different jobs, throwing the net wide in the hopes of getting one or two bites.

Much to my surprise, I had multiple clients reply to me fairly quickly.

I was working a delivery job at the time and so had some downtime to the point where I could do both jobs, I’d deliver food and while waiting for another delivery to come in, I’d write.

Then, within a month, I was hit with so many clients that I’d actually be losing money if I didn’t quit my day job.

It happened so quickly that I said to myself “okay, I’ll just take a break from delivery work and see how this goes.” I never went back to working full time anywhere else.

One of the cool things behind Upwork was that not only could you easily find clients, but clients could also find you, inviting you to apply for their jobs. This meant that the more success you had on their platform, the higher chances you’d have of getting invited to various new jobs. This made transitioning to working for myself far easier than I would have anticipated.

Switching from working full-time on a set schedule to working on my own schedule wasn’t particularly challenging for me. Before I started freelance writing, I spent my free time writing various different books and stories, so I had the discipline developed to just sit down and write. Perhaps the biggest challenge was learning how to write to please a client.

I enjoyed the change immensely. Going from always having to follow a bunch of company policies, rules and regulations to being able to just kick back and work at my own pace was a pleasant transition. I still enjoy working remotely today. So fewer headaches and you save a bunch on gas, which is a real plus!

Right now, I’m working for an addiction and substance abuse blog.

I write various articles about the different types of drugs that are out on the market as well as write about the negative effects that they have on people’s minds and bodies.

It’s a pretty great gig, my client uses a content management system to create a workflow for the writers. I can take on as much or as little work as I like in any given week.

All I have to do is select the topics that are available to me and then I get to writing. It’s an easy and no-frills way of getting down to the business of actually writing.

My routine is about the same each day.

First off, I don’t work regular hours too often because I’m a night owl at heart. Working the 9-5 life was always tough because I hated having to get up in the morning.

I don’t really feel like I hit my mental peak until around 11 at night, so working freelance lets me work those hours no problem.

A typical work day starts with me checking my master list of work and figuring out which jobs need to be handled next.

I tend to work with checklists, trying to get a certain number of words written per day instead of focusing on working a certain amount of hours. Hitting number targets give me incentives to work quickly and more efficiently, as opposed to hitting an hour target.

My routine is generally fluid. After all, when you have total freedom with both your schedule and your time, what’s the point of keeping things the same? I tend to work either early mornings or extremely late at night, depending on if I have other things going in the day. I have a lot of friends who work outside of the 9 to 5, so having flexible hours allows me to spend time with them in the morning when everyone else is busy.

Probably the biggest thing I had to adjust to when working remotely was the fact that I wasn’t going to be interacting with people very often. I enjoy working with others and am a very social creature. Truthfully, I don’t spend any time with others while working and that can make remote work a bit lonely. It can be tough sometimes, but the freedom afforded by the remote work is most attractive.

My routine essentially stays the same. But my thinking has evolved significantly in the recent months. With Upwork, it’s easy to just become a pipe-fed remote worker, waiting for the next job to arrive to you, but those jobs don’t always pay the best.

Now, I’m realizing that freelance work has unlimited potential for earning, if I’m willing to put in the time to find the right kind of clients or be willing to negotiate more aggressively with my clients. It’s definitely something that takes me out of my comfort zone, but it is also exciting at the same time.

I would say the only dedicated work space I need is a laptop to get the words written out.

But joking aside, I tend to stay at home when I write, usually sitting at my desk in the living room.

In previous times I had my own office, but that expense seemed to be a little unnecessary for the benefit that it was providing. I avoid busy places, although in my town there is this beautiful little tea house that has the perfect rustic charm and a great staff that I enjoy visiting to write.

Otherwise, I just stick at home. It’s comfortable and I can control the AC which is another important factor for me.

The too much work problem is always a great problem to have. Generally, I handle a high workload by one of two different ways.

The first is that I price my way out of additional obligations. Most of my workloads come from clients who are sending me a steady stream of jobs, so if I find myself with just too much on my plate, I will increase my prices, as a way to reduce the amount of work coming my way. It usually doesn’t cut off my client, but it does slow down how much they send me, giving me time to catch up on my workload.

The second way that I handle a high workload is by buckling down hard and knocking out projects aggressively. I usually do this by increasing my hours spend working on a job. I normally average between four to six hours a day working on my writing, but when it’s crunch time I can usually push between 10 to 12.

It’s not ideal, of course, so I try my best to prevent having to have these crunch days by learning to say no to new work when I have a large pile of stuff to do. It’s not easy passing on certain jobs, but it’s necessary. You can’t chase two things at once, or else you run the risk of losing them both.

As for having a scarcity of work, that’s definitely one of the bigger challenges that comes with this line of work.

I’ve had a few occasions where suddenly the pipeline has dried up, and let me tell you, it’s never a pleasant thing to finish a contract and realize there’s nothing left.

Usually when that happens, I start aggressively looking for new clients. Fortunately, with a higher level of ratings and a large track record on Upwork, I don’t have much trouble finding work. It’s usually just a matter of time before I get more work coming my way.

Although, in the past I learned a valuable lesson, unless you have a gig that is designed to give you more work, don’t assume that a client will keep their word when they say they’ll “work with you again.” I’ve had far too many clients tell me that they’ll send me another job soon, never to hear from them again.

A great way to prevent suddenly running out of work is to always be applying for gigs that you find interesting. Let’s say you’ve got a few jobs that will take care of you for a month. During that month, while working those jobs, you should be putting our applications for other gigs, but since you aren’t desperate for the work, you can be a little choosier and even increase your price point. Negotiation is hard when you know you absolutely need the job, so by negotiating when you don’t need it, you’ll be a lot more comfortable asking for higher prices.

It’s always a tough thing to figure out which clients are worth your time and which ones aren’t. While you never really know if a client is a good one until you’re working with them, there are a few red flags that I tend to look for.

The biggest one is the price ratio versus the demands they are making.

If I see someone who has a large list of demands for a project, but a very small price point, it means the client’s going to be too much of a hassle for the pay.

It’s one thing to pay very well and have a large list of rules to follow for a project, but if you’re expecting premium level work for pay below minimum wage, you’re not the kind of person I’d like to work with.

Another red flag is when a client has strange and unrealistic expectations for a work. For example, I’ve seen plenty of proposals where a client wants a book written that will become a New York Times Best Seller, or worse, they want a screenplay made based off of a “million dollar idea” that they had. These kinds of clients don’t have much of a connection to reality and will end up being a real hassle in the long run.

Sometimes you’ll run into clients who offer really steady work, but at incredibly low pay rates. But since the job is so steady, you might be tempted to take their offer and work for them. Chances are if you have strict time limits and a client who’s badgering you to get the work done as quickly as possible, chances are that you’re working with a farmer.

A farmer is someone who accepts freelance contracts for his own, then hires out other people at a reduced rate to do the actual work. He takes the lion’s share of the profits for doing none of the work. It might seem like a good deal at first, but the truth is that you could be the one getting the actual contract and getting paid the full amount instead of getting paid peanuts by someone else.

Usually I use whatever tools my clients request of me. Most often I find myself using Trello, which is a great project manager system that allows multiple people to coordinate on a group project together.

It’s easy to use and helps me organize which jobs are going to who. When I’m overwhelmed with a large amount of projects, I use my own Trello board to organize them all properly.

Other than that, I use little else other than Microsoft Word and my phone’s timer. Using the timer helps me stay focused on getting a certain number of words done in an hour if I’m on crunch time.

One of my favorite productivity methods is the Pomodoro Technique. It’s a nifty trick where you divide your work time into intervals of productivity followed by a break. Most people like to divide their work into 25 minutes, then a 5 minute break, but I find that my focus gets too interrupted by just 25 minutes.

Instead I work for about an hour uninterrupted, then I take a break, usually for 15 minutes. This method usually gets a significant productivity out of me, in terms of words per hour, I usually am able to slam out 3,000 words in an hour if I’m going at that pace.

Putting the phone out of reach is another important trick. I use my timer, but when the timer is running I don’t touch the phone. I put it to the side where I can slightly see the clock running, that way I know how much time I have left to hit my target goal. It’s easy to just spend your day messing around on your phone, especially since you don’t have a boss to yell at you about wasting your time. Sometimes, when I’m working a job that doesn’t require a large output of words written, I’ll actually just put the phone somewhere else. Out of sight, out of mind.

My biggest method of staying productive involves working almost as soon as I wake up in the morning.

I find that my creative energies wane as the day (or night) go on, so the earlier I can get going, the more productive I am. Even if it’s just for an hour or two, I find that working right after I wake up will increase my productivity by a high margin. If I wait until later in the day, after I’ve expended a lot of energy on other things, I tend to be sluggish and not nearly as focused.

In a word, I love the freedom of it.

I like being able to go at my own pace, work the hours when I want to and have a flexible schedule and life.

I enjoy all of the little things too, the lack of dress code, working out of my house, and the ability accept and refuse jobs based on my interests.

To me, remote work extends beyond a job, it becomes a lifestyle. Instead of having to order my life around my job, I have the ability to order my job around my life. For an individual who values freedom highly, it’s perfect.

The discipline required to work remotely is far more taxing than the discipline to work at an actual location.

Without having anyone breathing over your neck, there’s considerably less anxiety, but there’s also more temptation to slack off.

If you aren’t rigorous and disciplined with yourself, you could potentially end up wasting precious time or even days, putting you behind. While a regular job has guaranteed income, all you have to do is show up, remote work comes with a heavy burden, if you don’t finish your contracts, you don’t get paid. Sometimes that can get to me.

And then of course, probably the thing I like the least is the lack of socialization. Working in an office has a lot of negatives to it, but the thing I miss the most was having people that you could work with and talk to on a daily basis. Working remote is a lonely life. But like all tradeoffs, the question comes down to does the pros outweigh the cons? And in the case of freelance work, the cons are absolutely worth it.