How to Get your First Online Freelance Gigs

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In this episode of the HomeWorkingClub podcast, we tackle a subject that WE know many readers are interested in: How to get your first freelance gigs, specifically on freelance job boards such as Upwork and PeoplePerHour.

We talk about how to stand out, what kind of jobs to apply for, and which to avoid, and provide expert insight on getting your profile looking just right.

There’s a full transcription below if you’d rather read than listen to our dulcet tones.

Included in this podcast:

  • Getting your profile looking good (2:55)
  • How to stand out when applying for jobs (7:00)
  • Why small, one-off jobs aren’t always a bad thing (15:00)
  • Why you need to stick at it (19:52)

Supplementary Links and Information

Full Transcription

Some repeated words and unclear sections of the podcast have been edited to enhance readability.

ALEX: Welcome to the HomeWorkingClub podcast. I’m Alex and…

BEN: This is Ben.

ALEX: Hello, Ben. How are you doing?

BEN: Yeah, Not bad. Thank you. I’m looking out the window at some lovely, bright sunshine today. Which is always a bit uplifting.

ALEX: Excellent. The classic HomeWorkingClub podcast weather update. Although we are doing this over Zoom and you appear to be sitting on a tropical beach.

BEN: Yeah, I have been playing with the backgrounds a bit. You’ve got to do what you do to keep yourself entertained in these lockdown days, haven’t you?

ALEX: Absolutely. It’s amazing how good everybody’s getting with Zoom these days, and various other video conferencing stuff. It used to be the bane of our lives, but everybody’s enjoying them now.

BEN: Yeah, absolutely. I should probably say, as we said in the last couple of podcasts, apologies if there are any sound issues because obviously, we are at the mercy of the technology these days.

ALEX: Aren’t we all? Aren’t we all? So this podcast we’re going to be talking about something that actually I’m really, really excited about. Not that I’m not excited about the others, of course.

How to get your first gigs on freelance job boards. So, as is traditional Ben, pretend I’m an idiot. Tell me what these platforms are and how they work.

BEN: Okay, so I’m talking primarily about freelance job boards like, PeoplePerHour, and Upwork. They’re the main ones, but there are others as well. I have an article for the show notes listing all the alternatives as well.

So, they are boards where companies or individuals advertise for the freelancers that they need. As a freelancer, you can send in a pitch to do the jobs and hopefully begin to build a freelance business.

And the reason that we’re tackling this subject really today is that it’s something a lot of people have suddenly found themselves at home and thinking, “Right. Where do I find some work?”

The freelance job boards are booming at the moment because many of us can’t leave the house, or anything like that, because of what’s going on in the world at the moment.

So, I thought it’d be nice to sort of try and help people who are going from a standing start and just trying to establish relationships with those first two or three clients. Whether that is on, Upwork, or anywhere else.

ALEX: You know that there are many others available, we should say… even though we’re not the BBC, and we don’t have to have that disclaimer. There are loads out there, but those are the three sort of really famous names. They are the ones I’ve heard of anyway, so they must be pretty big.

BEN: Yeah, the nature of it is that they are the biggest ones and therefore where you’re going to find the largest number of opportunities as well.

ALEX: Yeah, I suppose it’s the case that if you are actually somebody looking for a freelancer, you want to go on the well-established boards, you want to go on the ones where you think that you’ve got the reputation to back up your company I suppose.

BEN: Very much so.

ALEX: Good stuff. So point number one and probably the most important thing is: Get your profile looking good. How do I do that, Ben?

BEN: Yes. So, on the all the freelance boards you have a profile area which is almost like an online resume. So you would have a profile photo, a summary of what you do, your experience, your key skills and attributes.

The way I’ve always put this is, putting together a profile for something like Upwork should be taking you hours and not minutes. If it’s only taking you minutes, I think you have got to wonder if you’re doing it right, because there are… I don’t think I’d be exaggerating to say millions of people on some of these boards.

So you do need to stand out and we’re going to move on to how to stand out when you actually come to apply for work. But the profile is every potential client’s first impression of you. So you’ve got to put your best foot forward and you’ve got to have it looking impressive.

You don’t want to be making any spelling mistakes. You want to be highlighting your key experience and highlighting what makes you unique as well.

I mean, a lot of people sort of say, “Well, I’m a writer.” It’s a lot better to say “I’m a cybersecurity writer” or “I’m a luxury travel writer” or something like that because there are so many tiny niches. It is better to sort of have a niche rather than look like a jack of all trades…which can be a bit of a problem if you do consider yourself to be skilled in lots of different things. But it is best to keep it focused.

People are looking for specialists and they can find specialists. So it is good to highlight what you are particularly good at and where you may be unique.

For example, there are virtual assistants that can do all sorts of different things. But you might be a virtual assistant who is particularly experienced in the financial industry or the medical industry, or you might have board governance experience or something like that.

Anything like that, that is unique to you, you want to be making sure people are aware of it.

ALEX: Good stuff. So basics wise, you obviously need a picture, good work history, and any previous roles as well. Spelling and grammar, as you mentioned. In terms of the level of detail, is it the more the better?

BEN: Not necessarily. I think certainly, in the area where you put the summary of yourself, people online have got incredibly short attention spans. And you will find when you’re applying for these freelance gigs, you may well find you are amongst 40 or 50 other people applying for them.

So you’re probably only going to get a glance at best. So you definitely want to make sure that you highlight the most pertinent and important information near the beginning of what you say and what potential clients are going to see. So longer is not necessarily better, I think.

It’s almost like you want that top bit of your profile to be what they would call an elevator pitch.

ALEX: Yes, absolutely. So, yes. Strong, strong summary backed up with detail. And I suppose that the point is that people will always…if they want to find out more about you, they can always ask.

BEN: Yeah, I mean, it is particularly important when you are first starting out as well because all of these job boards are feedback based. So once you’ve had your first few jobs and presumably got good-quality feedback, which is imperative if you want to make a success of these things, people are going to look at what other people have said about you… probably before what you say about yourself.

Until then, obviously, it’s entirely on you to create that right first impression. I think some of the platforms even allow you to do a video introduction as well. And so many people are frightened of putting themselves in front of a camera.

If you have got the skills and the confidence to do that, I urge you to give that a go. I don’t know…I should have researched before which platforms allow you to do a video profile. But I think you definitely can on some if not all of them these days.

ALEX: Well, guess what? We can probably put that in the show notes.

BEN: We could, yes.

ALEX: Well, that brings us on neatly to the second point which really is: how to stand out.

Obviously, let’s assume that we’ve got a good profile on there. We’ve got some good information. But what are a couple of things that you can do to really stand out from the crowd?

BEN: Okay, so what we’re talking about here is how to stand out when you actually begin to apply for jobs.

What I would say is, if you are new to the platforms, be completely honest that you are new to them. There’s no point in trying to paper over the fact that you haven’t got a history and you haven’t got feedback to share.

So, be honest that you’re new to the platform, perhaps even say, “As I’m new to the platform, if you’re not satisfied with my work, I won’t charge you.” That’s obviously a judgement call. But it’s something that I’ve done before when I’ve had the confidence that I’m going to make a good impression.

Think of other places where people have had positive things to say about you. I mean, if people have, for example, endorsed you for your skills on LinkedIn, with their permission, there’s nothing to stop you copying and pasting the nice things they’ve said about you, and including those in your profile or even in a specific application.

Obviously, get your spelling and grammar spot on. I know that sounds really obvious, but so many people don’t. I don’t think I’d be exaggerating to say you’re probably putting yourself in the 50% of the best applications if you just get the basics of the spelling and the grammar right.

Make sure…quite often the clients will hide something in their job description or their requirements. Something like “Please include the word monkey in the first paragraph of your application” and stuff like that. Literally to weed out people who don’t have attention to detail and aren’t reading the descriptions properly.

I’ve used that tactic myself when I’ve recruited for people on Upwork, and I literally bin every application that hasn’t followed that instruction. It’s a bit harsh to do it, but I think you want people who are taking it seriously when you are recruiting. So look out for things like that.

One other thing I would say is when you’ve completed an application, which again you should be taking a bit of time over and not just firing them out one after the other, read it through. Please, please read it through!

We were talking before we started recording…I’ve applied for writing gigs and spelt “writing” wrong! On Upwork at least, I’m not sure about the other platforms, once you’ve sent an application you don’t get it back.

You can read what you said and then put your fist in your mouth when you realise that you spelt “writing” wrong, but you can’t get it back. So read it through before you send it.

ALEX: I mean that’s just a maxim for me, having worked in the world of marketing for a long time. Before you send anything out read it, read it again, and when you’re happy with it, then read it one more time, and then send it.

It’s one of those things that I’m not naturally that way personally, but I’ve sort of taught myself to be like that over the years. The number of times that you catch something on the third reading. Or the number of times that you pass it to somebody else to just go through and they’ll go, “You’ve spelt your name wrong.”

BEN: Yeah.

ALEX: You get so close to something that you don’t notice.

BEN: Yeah, very true. So that final read-through is really important.

We spoke in the profile bit about video. One thing that you can do when you’re applying for a particular job, if you’re not afraid to get in front of the camera, is to actually record a video application. So you could record a little video and put it as unlisted on YouTube and speak directly to that client.

It’s so rare that people have the courage to do it. You could be almost certain that the client will take a look at what you’ve done, and if you say the right things and tick the right boxes for them… I’ve read articles from people who use these techniques to apply for jobs on freelance platforms and they find a lot of success doing video applications.

I can imagine a lot of people shuddering, “I wouldn’t do that.” It would frighten me a little bit as well, to be completely honest. But if you find yourself willing to do it, it is well worth giving it a go.

ALEX: Yes. I suppose it’s what you’re comfortable with as well. I mean, you want to be your authentic self as much as possible. You don’t necessarily want to kid people into thinking you’re something you’re not. But if you are comfortable with that sort of thing…

I remember, years ago, I used to have a picture of myself on my resume or my CV, which not many people did, and the logos of the companies I’d worked for just to sort of smarten the document up a little bit. I remember the chap who actually hired me saying, “Oh, yeah, you don’t look anything like your picture on your CV.” It’s like, “You remembered I had a picture?” “You were the only one who had a picture on your CV.”

BEN: Yeah.

ALEX: It worked!

BEN: This is the point, it is all about standing out. On a previous podcast we interviewed Matt Barrie, who’s the CEO of, and standing out was the thing that he said several times about when you’re taking your first steps onto these platforms. Anything that’s going to make you just rise that little bit ahead of the many other people you’re going to be competing with.

ALEX: Yeah, well worth a listen that podcast with Matt Barrie. Really inspirational and motivational guy, isn’t he?

BEN: He was, yeah. We’ll have to stick that in the show notes.

ALEX: Excellent. It’s becoming our catchphrase: “Stick it in the show notes.”

BEN: Yeah.

ALEX: So we’ve got a really good, detailed profile, we’ve highlighted our key skills, and made ourselves look decent. And we’ve done a couple of things to stand out. So now we’re applying for jobs. What would you say in terms of looking for jobs? What are a couple of tips there?

BEN: Well, there’s one thing I’ve actually written here. Don’t apply from rubbish gigs! I think there can be a temptation, especially in the early days.

I actually contributed to an article on how to win jobs on freelance platforms only a few days ago, and I got sent a link to the article…again, I will put it in the show notes…Someone else who contributed to that article gave the advice of just apply for as many things as you can.

I thought that is really, really terrible advice that I don’t agree with.

I think in the early stages you could find yourself sending quite a lot of applications out and not getting anything. It makes you almost kind of lower the bar and lower your standards more and more and more.

But you should still be looking out for the basics, such as: you can read feedback on the clients, you can look at how much they usually pay freelancers and have paid freelancers in the past.

I do tend to apply the same kind of standards to the job descriptions, as I would to the applications as well. It’s just if I feel the client hasn’t put much thought into what they’re asking for that rings an alarm bell for me. If it’s very clear that they’re paying really, really poor money as well. So, all of those things.

I think we could do a whole separate podcast on how to separate out the good gigs from the bad ones, but all I would say is don’t, out of desperation, drop your standards below where they would be otherwise.

ALEX: Yeah, I think we touched on, earlier on, that these platforms are booming and there are a lot of people competing for, particularly, the better jobs. But that doesn’t necessarily mean that, you know… if you back yourself and you think you’re going to do a decent job, that doesn’t necessarily mean that you should give up or feel that you’re going to have to go for anything that’s there.

I think, you know, it is perhaps a bit of a buyer’s market at the minute. But that doesn’t mean necessarily that you should, as you say, it doesn’t mean necessarily that you should drop your standards because of it.

Just compete a bit harder.

BEN: Yeah, absolutely. I’ve written sort of another side to this, which is, don’t necessarily dismiss small gigs because quite a lot appears on these platforms…

One example that I’ve got is… quite often there are jobs for people who want people to do, not voice work, but actually recording voice recordings to train sort of systems like Alexa and Google Home, and stuff like that.

And they might want people with specific dialects like Southern American accents, Northern American accents, Southern English, Northern English, Scottish, that kind of thing. These jobs might pay $10, they might pay $50. But if you put in a good application for them….to train these systems they need dozens and dozens of people to do these things…actually something like that could be a good way of just getting a quick bit of five-star feedback.

It might be something completely outside of your interests or outside of your knowledge. But there are those kinds of low-value jobs that are from particularly reputable companies. So don’t dismiss them!

Just because something is small and it’s 10 minutes work for $5-$10. That actually could be a good way to get your first few bits of feedback. So don’t dismiss those. I did some of those in the early days, and I don’t regret having done it.

ALEX: Fantastic. I suppose that’s the sort of thing…if you are looking. I think we talked before about “Don’t just jump on the on the first one that you see.” Go through, consider quite a few. Some of these platforms will charge you for the number of applications or something…Is that right?

BEN: Yeah, Upwork does. Essentially you have to pay for connects, so it does cost you a nominal amount. It varies on the value of the job, but somewhere in the region of 60 cents per application.

So it’s not an enormous amount of money, but you still don’t want to be throwing that away applying for things that are either completely irrelevant, you’re not going to stand a chance of getting them, or things I would put in the category of rubbish gigs. Which we spoke about a couple of minutes ago.

Other platforms don’t necessarily work in the same way. I’m pretty sure doesn’t cost you anything until you actually win a job.

Generally speaking, you should be applying for things that are a perfect fit for your knowledge. Which is why it’s well worth searching for anything you know a lot about.

So you know loads about snooker, each time you go on the board type in “snooker.” Find out if anyone wants articles written about snooker if you’re an expert in it because that’s going to make you shine when you actually come to put the application in.

So think of what you know about, think of the knowledge that you have that other people don’t generally have, and then try to look for things in those kinds of niches. So that’s the general rule.

I’m not for a moment suggesting that once you’re experienced on Upwork or Freelancer that you should carry on just applying for random $10 or $20 gigs. But, it is a bit different when you’re looking for your first ones…because if you’re looking to build up your first three bits of feedback, it doesn’t matter if one or two of those are for doing something that really anyone could do.

It’s just a question of pleasing the client. Doing it in a timely fashion. Doing it well. Doing it right.

ALEX: Yeah. I genuinely didn’t think, when I was writing the notes for this, that we would be talking about snooker at all during the course of the podcast. There we go.

BEN: I don’t think I knew until about four seconds before I said it!

ALEX: I think that’s actually a really, really useful thing. Having a look around and actually seeing that… hadn’t really occurred to me before. I think a lot of the stuff we’ve been talking about is from the basis that there’s going to be loads of people doing stuff out there, but there are things that you can do to narrow down the field and actually make it really fit into your wheelhouse and be the sort of thing you should go for.

Actually, I think if you find yourself in that position where you’re applying for something and you can go, “I know a lot about this subject,” then that’s going to make your application better in itself because that’s always a great way to start off.

If somebody comes in and goes, “I’m a massive expert in this area,” then you’re going to read the next thing that they say.

BEN: Yeah, absolutely. I think the more generic that you come across as, and the more sort of “jack of all trades” you come across as, that’s just going to lower your chances.

These are gigs they’re not… obviously we always hope that freelance gigs will develop into long-term client relationships… but your first few gigs you do on Upwork or Freelancer… all the clients want to know is that you’re going to do that job without aggravation and do it well for a price that everyone’s happy with. So that’s what you’ve got to prove you can do.

ALEX: Good stuff. Is there anything else that you would suggest as a tip? Anything else that really stands out in your experience?

BEN: Stick at it. I think a lot of people are scared away from these platforms too soon because…yes, it can take a lot of applications before you start getting the gigs. I always make use of the eBay analogy. You’re not going to get the same amount of money for selling stuff on eBay until you’ve established a decent amount of good feedback.

So these first steps, they are hard. Again, referring back to the podcast with Matt Barrie that we had, he said it is the hardest freelance job to get, is that first one. That is very true!

So try not to be one of those people who gives up before it happens. Because if you do all the things we’ve said, it will happen. I’m confident of that.

ALEX: Excellent stuff. And of course, I mean, if you are one of those people that doesn’t give up, then you kind of want everybody else to give up as well. So, you know.

BEN: What was it that Matt Barrie said? Average… “there’s no room for average anymore” or something like that.

ALEX: Yes. I did have the notes up but I took them down, being very efficient. But yeah, “The age of average is over,” I think it was, wasn’t it?

BEN: Yeah. I think that very much applies nowadays. They are undeniably crowded platforms. But I can vouch for the fact that, if you do this right you do find work.

Once you get to that stage where you’ve got a good amount of feedback built up, it’s incredible that you can go to these platforms and know that there is almost like a tap of work that you can turn on. That’s a great thing to have. Especially… well any time…especially in uncertain times as well.

ALEX: Yeah, well, absolutely. Looking at the big picture of these. We are now in a world where, you know, we can talk about things like Upwork, Freelancer, and PeoplePerHour being well-established platforms. That marketplace of skills…

I think there’s an article we touched on in terms of the freelance world issues such as the gender pay gap and equality in employment. Those things are much less stark in the world of freelancers because people tend to employ more on skills than they do an appearance and background and that kind of thing.

So it is a wonderful opportunity out there. That if you are a skilled person, you are looking for work, these platforms are there. There are lots of jobs available and there’s lots of stuff out there. So don’t be put off by the fact that they’re being really popular because it’s a really positive thing.

BEN: Yeah. This world is a genuine meritocracy. Which is nice to see.

So if you keep on at these platforms and you feel it’s sort of unfair that you’re not getting the work… be very honest with yourself. Think, “Okay. What am I doing that might be coming across as average? How am I not raising my head above that kind of average level and appearing something special to these clients?”

Because that’s what you need to do to get the work.

ALEX: And of course, you know, the world does need average people after all. So don’t be too hard on yourself.

Otherwise, how would we define ourselves as exceptional!?

BEN: Absolutely. I think that’s about all. I would hope that would be enough but I do also have an article, which once again I will put in the show notes, that I’ve got about 27 tips for applying for these jobs. So you’ll probably pick up some more from that as well.

ALEX: So just to recap very quickly. When you’re setting up your profile on your chosen platform, make sure there’s good detail in there and highlight your strengths. But also, perhaps, don’t look to put too much in there and make sure you really are providing a very good summary of what you’re good at and why somebody should employ you.

BEN: Just one thing I’d like to add there, as well. It’s sort of a basic of sales and marketing, but try to sell the benefits that people get from using your services rather than just listing attributes.

That can be quite difficult. But if you can master that… and you can always look at other people’s Upwork profiles and profiles of successful Upwork people, they’re freely accessible…Have a look and see how people are doing that.

Sorry, it’s just something I’ve…

ALEX: No, that’s a really good idea.

Yeah, absolutely. Look at what other people have done…people who have been on there for a while. I think it’s a really good tip.

You also said, Be honest. If you’re new to the platform, say you’re new to the platform. Be authentic. If you really want to stand out, look at some endorsements that you’ve got elsewhere. Try and find some validating information that will make you attractive to those employers.

And if you want to do something along the lines of a video… a video application, or a video on your profile, that apparently has really helped some people stand out.

The other thing is, don’t give in to desperation. We’re not recommending that you fire off hundreds and hundreds of applications, but do be choosy about what you apply for. Don’t necessarily think, if you’re not being successful, that you have to give in to the first thing that comes along.

Also, keep your mind open to some things that perhaps you weren’t considering when you first went onto the platform, because there are some really cool small gigs out there that might actually get you along your way and, at the very least, provide you with some good feedback.

The other super tip was look out for those “Easter eggs.” Look out for the things in the job advertisements. Really read them carefully, because there might be some things in there that will actually help you stand out from the rest or will help you get through to the next round.

BEN: Yes.

ALEX: Have I covered everything there Ben, do you think?

BEN: I think you have. Thank you very much.

ALEX: Well, good stuff.

Thank you, everybody, for listening and do please write, subscribe, and write a review.

What we’d really love is to get in touch. If you’ve got experience of these platforms or you want to talk about them a little bit more, do get in touch with us. We’re always happy to hear from people. Ben, how can they do that?

BEN: Via my email address.

ALEX: Thank you very much. Ben will be putting the show notes up on this as well. So if there’s anything we’ve talked about, it should be in there. But if there’s anything we’ve talked about that we missed, then do please get in touch and we will absolutely sort it out for you.

Thank you very much for listening.

BEN: Thank you.

2 thoughts on “How to Get your First Online Freelance Gigs”

  1. Hi, another great podcast. Some of the things you mention are so simple but sometimes we forget the simple. Loved the part about the video application, something that terrifies me but for that ‘stand out’ feature it is worth thinking about, Thanks guys.


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