Freelancing in the 2020s — Xtra Freelancer Community Chat #001

Updated: Sep 27, 2019

Curious what the future holds for working as a freelancer online in the coming decade? Two industry insiders meet to discuss the current state of the market and coming trends.

This is a transcript of our latest podcast episode, (Spotify, YouTube) which has been edited for clarity.

Speaker Introductions

DLKR: We're in Tokyo, where Xtra is headquartered. I've been in Tokyo for about 22 years, and specialize in marketing and online communications. I've been involved in online freelancing, mainly as a buyer of services, for many years and was excited to get on board and help out the team here at Xtra, which runs two freelancer crowdsourcing platforms; Conyac and QuickTranslate (more on these later).

Naoya: I manage the operations section. I specialize in facilitating client services and lead my coworkers who run various client projects. Most of the projects we do are translations and sometimes research. Our team structures the projects and runs them for our clients.

Freelancers Lacking Community

Naoya: Crowdsourcing was still emerging back in 2009. It expanded in 2015. Our platform, Conyac, became significant in the crowdsourcing field. One of the issues that freelancers face is the lack of security when it comes to doing full time freelancing. There's no income security, and there are insurance hassles. There is also a lack of community, which is a crucial issue.

DLKR: Obviously, there are all kinds of resources online, but that doesn't break the isolation factor. You can exchange information, but there's a limit to what you can do in terms of the human elements. I would suggest freelancers find meetups in their local area via

Xtra has organized meetups in the past, and we should get back into doing that, but we're limited by our geographical location.

If you're in any major city if you search for a freelancer meetup, or just Google that, you'll probably find something. But for more remote people, people in more isolated locations, they've just got to find some kind of social outlet somehow. It doesn't necessarily have to be meeting up with other freelancers. It could just be any kind of a sport or a hobby. So we almost need to get out once in a while, at least once a week and meet people somehow.

Naoya: As much as freelancers maybe crave for a community, what would be an incentive for them to join or continuously interact with one? Freelancing is so broad that it would be hard for them to connect around a central topic.

DLKR: You're right. For example, web developers and translators encounter different issues. About the only thing they have in common is that they're working online and not meeting clients face-to-face. However, within that, there are some things which they have in common.

We're going to have to see how our community forum progresses. Whenever you start a new forum or group online, it's a chicken and egg scenario. Nobody wants to join an empty and dead group, so through Xtra's freelancing platform, Conyac, we found people who enjoyed chatting about different issues online. We hired them to make one post or comment per day. We gave them a few quality guidelines so that the conversation would be worthwhile for new people who came in.

Naoya: Good one. If it's a free community where everyone can join, they don't have any direction, but if they can follow some sort of facilitator, it would be stimulated.

DLKR: Yeah. I fulfill that role for this particular group. There are many others out there online.

Since we're headquartered in Japan, most Conyac users are Japanese, and a lot of the job listings are in Japanese. So, with our forum being in English, there's a language barrier. Some people feel reluctant to join an English language forum and vice versa. I can read and write in Japanese, so I could join a Japanese language forum, but I gravitate towards the English ones because it's easier.

This is one thing we'd have to work on moving forward. Maybe this will be solved by other layers in the tech stack, such as online machine translation so we can have a bridge between people on the same forum. We're currently using a platform called I believe they have machine translation built-in, but of course, it still has limitations.

How to Be Successful as a Freelancer

Naoya: One of the comments I get from unsuccessful freelancers is, "I'm not seeing any proposals." I'm there on the platform as a client looking for solutions. But many times, I see requests for instructions. The common pitfall that freelancers fall into is that they can't come up with the answers that clients want.

Freelancers also struggle with marketing their ability to provide such solutions. Thus, as a client, even if you get solutions proposed by freelancers, you're worried and think, "Who is this person I'm talking to? What qualifications do they have?" Freelancers who can take a consulting approach with this scenario in mind will gain trust from clients.

DLKR: Most of my experience on freelancing platforms has been as a client. As a buyer, I've probably spent around 50,000 US dollars since the early 2000s. I first joined Elance back around 2002, and then I used it on and off. They merged with another platform called oDesk and these days it's called Upwork.

I've experienced two types of hiring:

  1. Where I post a brief in the marketplace and then people bid.

  2. Where I buy a set service which is available on the freelancer's profile.

In a marketplace, which is what you were describing, somebody will put out a brief saying, "I want you to do this, this, and this." If it's a popular job category, many freelancers are just spamming every job with a ready-made template proposal which outlines who they are and what they offer.

As a client, since they're not saying anything about my specific requirements, I feel like they're not serious. Sometimes I'll come across a freelancer who's new to the platform and has no feedback from past clients. When you're starting out on a new platform, you have to build up your track record, even if you've got a lot of previous experience elsewhere. They'll undercut the average pricing, be specific about my requirements, and use a more personal tone. Some of them even go through the trouble of recording a video speaking to me as the client — that has a lot of impact.

Freelancers may feel that investing time in a proposal could be wasted. There's a high chance they might lose to other better-qualified candidates, but they will definitely stand out.

Naoya: Sometimes, clients don't give enough information. A lot of it has to do with the user interface. There should be a more natural way to structure the request.

The Evolution of Crowdsourcing Platforms

DLKR: I've used all the most significant platforms, and none of them are perfect. Of course, they are quite refined and well put together because they've got over ten years of history. Even some of the smaller ones such as Conyac have been worked on for over a decade, but there's no end to how much they can be improved.

I use Conyac as both a freelancer and a client. Whenever I notice anything which could be improved, I'll submit it to the development team. It helps them because they see it from a technical perspective. It's essential to get that kind of feedback. The challenge is 99.99% of users of any online service if they encounter difficulties, they're not going to give feedback. They're just going to go elsewhere or struggle and try and find a way around it to make it work.

Advice for New Freelancers

Naoya: I would suggest building a multiple skill set. The labor market has changed. It's becoming more diverse with niches. Freelancers should identify these and fit themselves in. This is where self-marketing comes in.

DLKR: Based on my experience working in hiring a lot of freelancers for many different things, I would say that first impressions count a lot. If you're new to a platform, you can just work with what you've got, which is trying to make your profile as appealing as possible.

  • Have a sharp profile picture. If you don't want to show your real face, then come up with something creative that at least looks like you put some effort into it.

  • Think about how you're going to word your profile and introduce yourself and your strengths and what you can offer.

  • If English is not your first language, then maybe hire an editor to help you out with that.

  • If offering a set service, make that listing attractive. Drop the pricing until you build up at least a few five-star reviews.

  • Have consistent branding across your various profiles and accounts online and link to your Conyac profile.

Of course, you don't have to go through a marketplace like Conyac. If you've got the time, you can try to contact companies through their various social media.

Naoya: No matter how skilled you are, if you can't communicate your value to prospective clients, you're not going to get hired. Even if you're not an expert at something, if you can somehow communicate that you're willing to brush up, or serve your client differently, that's something that might persuade a client to take a chance on you.

DLKR: Building on that, I would say to narrow down what you offer. For example, marketing is the field that I'm involved in. There are many areas of specialization within it. I focus on my ability as an editor of content written in English. I have a lot of other skills and knowledge. But editing is my strongest skill. If I was to say that I'm a "Marketing Professional," it's too broad. It's better to undersell in terms of what you can do and then surprise people later with your other skills and expertise.

I have some skills when it comes to photography or editing photos, but I am not by any means at the level of a professional photographer or Photoshop guru. But when I bring those skills into a job, it adds value and is a pleasant surprise. I can add some value to the visual side of the content.

Even within the field of translation, if you say "I'm a translator of Japanese to English," that's not enough. You need to say, "I can translate medical documentation." That makes it easier for others to recommend you via word of mouth. This is something we don't hear a lot about with online freelancers. But people do give recommendations behind the scenes.

Rather than being a generic person in "X" field, you want to narrow it down to precisely what you're best at.

Naoya: Fitting into a niche is one way for freelancers to build a more secure career because there are likely going to be less competition. There is going to be different markets, but you want to be the person known for handling a particular kind of work which people contact and recommend to others.

Freelancing Online in the 2020s

Naoya: Diversity will bring niche markets. Freelancers might be able to fit themselves into a completely new market or be the only freelancer in a particular segment.

DLKR: I would advise freelancers to keep an eye on AI within their niche and how they might automate aspects of their work. For example, I have noticed how AI is creeping into photo editing tools and automating some tasks. Photographers and designers can ride this wave of increasing automation to accelerate and improve their work. They also should seek to add value on top of that, because sooner or later clients will discover that these tools exist and learn to do it themselves.

It's easier today than ever to build a freelance marketplace. There are more and more out there. Don't limit yourself to the top three. Consider smaller ones like Conyac because you might stand out more and there's less competition for some niches.

Naoya: Exactly. It's all about positioning yourself where you can deliver the most value and staying ahead of the trends.

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Transcription by Rev + edits by DLKR

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