How to Get Freelance Work on Upwork (That Actually Pays Every Month)

Michael Elliott, who says he's earned over half a million on Upwork, argues that Monthly Recurring Revenue from retainers beats chasing one-off projects. A few $1,500/month retainers outpace someone grinding $2,000 gigs. He shows how to land retainer clients, build reviews, and reach $20K/month MRR.
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Hey guys, Michael Elliott here. If you haven't met me before, I've earned over half a million on the Upwork platform. Almost every freelancer that I know starts next month on zero. Every month they finished last month's projects, got paid, and now they're back to sending proposals like nothing happened. That's not a business, that's a hamster wheel with invoices. Today my job is to explain MRR in a digestible format so that you can understand how to layer and grow your individual freelance business. Monthly recurring revenue is the only metric that really matters, because when it comes down to monthly recurring revenue, you are in a position where you are building something. And there are many different nuances to this that benefit you as a business owner. You can have a certain baseline that you want to stay at and then have a lifestyle business. You can continue to grow and hire more people and scale the business that way. You can do whatever you want to do. But one thing that you know for a fact is that every single month when you look at your dashboard, your invoices are all going to land. You're going to have X amount of dollars inside of it, and your competitor is going to be chasing 50 proposals like a dog chases a bone or chews a bone. And this image illustrates it perfectly, because if we take Freelancer 1— two of these freelancers doing exactly the same thing, just a different model— Freelancer 1 takes one-off projects. He sends 50 proposals, he wins one project, that's $2,000, takes him a couple of weeks to complete it. He then starts over sending proposals again. His annual earnings are $24K. 12 separate projects, $600 per proposals. This is a simplistic way of looking at it, intentionally. So 12 separate projects, 600 proposals. Now when we compare that to Freelancer B, he has retainer clients, so he still does the same 50 proposals, and he may very well still do the first $2K as part of that project. But what Freelancer B has learned is that you prime the client from day one for a long-term retainer. You drop a few things in about upkeep, maintenance. Doesn't matter how big the retainer is as long as it is a retainer. You are constantly tailoring your sales pitch towards that client going on to a long-term retainer for you, whatever your service is. Like, even web developers, hosting, like, they may make up a markup on hosting websites. It's crazy. Like, and if you're freelancer B and you figure this out, what happens is you have client A come through the door, $1,500 a month in recurring revenue, then client B, $1,500 recurring revenue, then C and D doing the same thing. They all pay simultaneously on the first of the month, pro rata, whatever. But every month Even if they send zero proposals after that, you are in a position where— after month 4, should I say— you're in a position where you have 4 clients, zero proposals sent, and your annual MRR, if you can retain them, is $72K a year. The difference between those two individual things really isn't much. It is a technique and a strategy being deployed properly in order to be able to build that MRR. Now, what does this look like that might look a little bit more familiar to you? Let me draw this out. This is the months of the year, and this is the amount earned. Now what you're going to see if you are a normal business that runs on a single project retainer and doesn't focus on MRR is this: the roller coaster every month like this. I'm going to run out of space to show you, but you can have really good months, but then you're back down again, and you just end up on this, this sort of roller coaster of inquiries and projects. You win a project, that's great. This month was really good, so here we made some big dough. It was a great month, but then that client's gone and there's no monthly recurring revenue. Whereas what it should look like is this. If you draw the same similar graph and you have month 0 here, and this is month 1, we get to month 1, we get a $1,500 retainer. Then month 2, we get another $1,500 retainer. Same again, same again, same again, same again, same again. And I call this the roller coaster versus the staircase. Method. That's the two different ways as a freelancer you have opportunity. You can either build it like a staircase and add on blocks like Lego building blocks, add them on, or you can literally sit fighting for projects, quoting for one-off projects. Even if they are larger in value doesn't mean that as a prolonged effect you're going to make more money. It actually doesn't. It means the complete opposite. I've seen people take on projects maybe like 3 times the size of mine, but it takes them 3 times as long to do it, and they don't have the monthly recurring revenue. So once that project ends, they end up stuck on the raft. Of course, the ideal sort sort of gap here is that you get an extremely large bag of money for a project and then they become MRR. And that's perfectly doable, I do it all the time. But when it comes down to your strategy, it 100% needs to look more like this on the right. Now of course, for the realists in the room, you are going to see some downward steps. You're not going to have your best month on record every month, especially as you get further and further in. It all depends on your activity, the inbound, etc. But what will happen is you will see with the staircase case approach, a line that goes like this. Whereas with the approach of a freelancer who quotes one-off projects and just builds them out for fun, you'll see a line that goes like this constantly. And if you're very, very lucky, you might have some sort of median where you continue to win jobs, but nothing is promised. Nothing's promised to this freelancer either. But let's fast forward and just say like 10 years. This client onboards one client a month. He's at 120 clients. There might only be 67 left with him, but this client here has probably got 6, like maximum, because he felt lucky on a few retainers that the client brought up. Technically, he'd be on zero. So you can see very clearly there, we're at $1,000 each at this stage. $67K a month, he's got a 7-figure business, whereas this client is still starting every month from zero. That's the difference, and that's the difference between success and MRR. And I can tell you something now, when you hit about $20K a month in recurring revenue, it doesn't matter if you're earning $200K a month or if you're earning $100K, just to pick out two numbers. Your lifestyle really doesn't change for the normal person. $20K a month, it's around the number where nothing changed after that for me. I got to this stage and I was in a position where I got to $20K, then got to the higher numbers. And as you get to the higher numbers, what starts to happen is you don't actually— you pay more tax. You try and do what you can to ensure that you invest and carry on growing the business instead of that. But my lifestyle hasn't changed. I could go and buy the really fancy car, could go and buy the massive, massive house. But I don't. I live in a decent-sized house and I just focus on like living life normally. And that's my number for me. If you're at $20K a month and you're taking that home, you pay tax on it, you know, whatever's left, $12K, $13K, you live a perfectly good lifestyle. You can go anywhere you want in the world. You can do whatever you want to a certain level. So what I'm saying to you is this: when you start hitting $67K a month retainers in MRR, life becomes a little bit of a joke because we don't all want to be Elon Musk. $67,000 a month. Like, can you spend it really? Because I couldn't spend it unless I fed my Rolex addiction or like, you know, continue to, to blow it on incredibly expensive things. And that's just not the way that I'm wired. So if you are, like, good for you, but it's not for me. I invest and reinvest. The client stack. So every retainer stacks, you never go backwards. You try and never go backwards anyway. It's not always the case, but this illustrates again very, very clearly how the month one is the baseline here is zero. You then win the clients. These are varying this is why I put this in here, because they vary in numbers. But you'll see that the average grows, and then the new retainer sits you at £7,500. As the cancellations come in, you don't actually worry about them, because as you grow, and you— if you went down the team route, you would end up like 4 clients canceled but 9 came in. So your MRR just keeps growing, and that's how every successful business is built. That's just the way that it goes. So the monthly reset without MRR— you wake up on Monday the 1st or whatever day it is, and you're in a constant panic. You're worried about where the money's going to come from, feeding you're constantly applying for jobs. Focus on— and especially if you haven't made a decision on the service you're going to use yet— focus on something that can deliver monthly recurring revenue. Trust me, you'll thank me later. When it comes down to the— with MRR, they have $6,000 already locked in on the first month. They have certainty, they have growth, they have freedom, they have everything that you could possibly want out of life, and they have the ability to be able to go on and scale way beyond what they would be able to if they were taking one-off projects. And this is a massive, massive problem in the AI arena because you take on a lot of AI projects. And when you have like 6 AI projects spinning, they are high value, but scope creep kicks in. Things start to happen no matter how much you try. I don't care what anybody says, when they have these scope creep documents, something always creeps in. And if it doesn't creep in, you are very strong with your boundaries, which is how you should be. But when you do that, you end up with an upset client, bad review, something happens, friction, chargebacks. All these things can happen. If you build a service that you offer every single month where there's something new, fresh, delivered, that's built, that the client can tangibly see, you leave yourself in this position right here, which is where you to be. And obviously on the other side is the position without MRR where you don't want to be. Now realistically, some of you watching this video will have a lot of money, some of you won't. And you'll have— some of you will have a lot of MRR, some of you won't. Some of you won't even have a skill set yet. But this is what you need to do. You find a skill. This is you in this little box. This is you. You learn a skill. You put time into learning something that you know pays monthly recurring revenue. That is the only service that you should focus on learning. Monthly recurring revenue services. Nothing else. Anything else, just bin it. I don't care. Monthly recurring revenue. You then take it to platforms like Upwork, like Facebook groups, like I mentioned before, like cold email. You take it to these individual areas and you start trying to win clients from them. And yeah, you'll kiss a few frogs. No one's gonna lie to you on this channel, but eventually you'll win a few clients. Your Upwork projects start to progress. So when it comes down to your Upwork projects, you've then— you've done a little bit of cheap work than what you would do, you've underquoted, but you've now got 10 projects that have 5-star reviews on them. Not only that, 7 of them went on to— well, let's say that the projects close, it depends on that, because obviously to get the 5-star review, the project has to close on Upwork. But let's say they— the first 10 close after a while, but you've still got 20 left in the bank. You've got monthly recurring revenue that you can count on every single month, probably totaling definitely totaling 5 figures plus, okay, so $10K plus per month. And you focus on delivering a good service to that client so they don't leave. In the very same way, if you're posting in Facebook groups, which is something I strongly, strongly advise— Facebook group activity is really important. It's like a base level of brand awareness, but you have people coming to you. Trust me, I still get DMs to this day from— that's exactly where I started. And Facebook groups are important because they're unique, they're not saturated as much as everywhere else. And what they allow you to do is build an authority inside of groups that are relevant to your niche, then win monthly recurring revenue jobs that add to this total. And then cold email, a little bit of investment from your side, or you can just go and cherry-pick them. Eventually you'll grow out of that as a, as a business. You'll end up starting to pay for things like Inboxology where you can then buy loads, and Instantly where you can send the cold emails from. Instantly is an amazing tool. You can buy emails directly in there. But that's how you get to a 5-figure-plus MRR. That's what you do. You master the skill first. We don't even master it. Nobody's mastered anything. Everyone's improving. Like, the 100-meter runtime improves because people improve in the way that they approach things. Everybody improves at everything. And you just need a baseline that's better than what business owners have and provide a true value so you're not a cowboy. You're actually somebody who can go into a business and make a difference. And that's why I'm not against starting when people are starting out against free to no work. The best line really is— what I like is, if you don't like it, you don't pay, and what you pay is whatever you want. And I like that fine because it's sales-driven. But when it comes down to that, if somebody came to me with that, I would, one, think that they were extremely competent in what they did. It would give me good vibes because I'd be like, okay, like, you're up for the challenge, I guess. Two, it would mean that there's no risk, so there's no friction. And three, when it came down to paying them, I would likely pay them more than what the retainer would have been, because at the retainer point of view, I would have negotiated, whereas I wouldn't have negotiated when it comes down to somebody who does this job and I'm like, whoa, That's crazy, you did that, that was amazing. Here. And I don't advise you stick on that model forever, just doing things and hoping that somebody comes and pays you, like, because again, like a lottery ticket. But that's a great way to get off the ground. Do it for a lot less than your competitors for testimonials, video testimonials, 5-star reviews. You don't understand how far that goes. But monthly recurring revenue is the key to every freelancer's success. Whether you want it to be classed as a business or not is up to you, but if you have MRR you have a business. If you don't have MRR, you might have a bit of credibility, you might have a bit of brand awareness, but you have no money on the first of every month. So I want you to focus now on driving monthly recurring revenue because it is the only thing that matters. Hit like, hit subscribe. In the comments, drop me a message if MRR is something that you are focused on, or if you've gone for volume of projects, because it's really important, not just to me, not just to you, but to everybody who's watched this video. They need to know that they're not on their own. Because I've been on the hamster wheel and I've been off it, and trust me, being off it is a lot better. My name is Michael Elliott. I'll catch you in the next one.










