Why Most Freelancers Fail at Pitching (And the Secret to Landing Your First Client)

Most freelancers fail at pitching because they send generic templates instead of showing a specific client how they can solve a real problem. In this episode, Al Calder explains how to niche down, build a portfolio with no clients yet, personalize every pitch with the Problem, Agitate, Solve framework, and keep reaching out even when you hear crickets. With the right clients, smart pricing and a little patience, you can land your first client and turn them into a raving fan.

Welcome back to The Freelance Insider Show!

Today we’re looking at why most freelancers fail at pitching and how to break the odds and land your first client. We’ll really get into the nitty gritty of this crucial topic – it’s impossible to land clients if you have no idea how to create a pitch that grabs their attention. Not to worry, you’ll be writing pitches like a pro after this episode.

If you’re ready to start writing killer pitches let’s get this started!

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What You’ll Learn in This Episode

• Niche down to stand out: clients hire experts, not generalists, so specialize in a specific service for a specific type of client, and start with something you are passionate about.
• Build a portfolio with no clients: create tailored samples for your ideal clients, even fictional ones, and volunteer for nonprofits you care about to gain real-world experience and testimonials.
• Craft a compelling, personalized pitch: research the client’s pain points, show you have done your homework, and use the Problem, Agitate, Solve (PAS) framework to present your service as the solution.
• Find the right clients: start with your existing network, then target sweet-spot clients through strategic outreach on social media or targeted emails to marketing executives.
• Use platforms wisely and price with confidence: treat Upwork and Fiverr as stepping stones, not a final destination, attract clients with passive pitching, and start with no-brainer pricing, then raise your rates as you gain experience.

Episode Highlights:

• Finding your focus
• Cracking the portfolio puzzle
• Mastering the art of the pitch – personalization
• Problem, agitate, solve (Pas)
• Ups and Downs of outreach

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Full Episode Transcript

Welcome: Pitching Your First Client

Al Calder: Welcome to Freelance Under the Hood, the podcast where we take a close look under the hood of the freelance world. I’m your host, Al Calder, a freelance writer and audiobook narrator. I’m here to help you with your freelance journey. Whether you’re just starting out or looking to ramp up your freelance game, you’re in the right place. Hey there. Ready to dive into the world of freelancing again? All right, let’s do it. Today we’re going to be talking about pitching and landing that first client. We used a really great mix of resources to put this week’s episode together. We looked at a ton of articles and YouTube videos backed by my years of experience, battles through trial and error and many highs and lows chasing the elusive perfect freelance client. So all focused on helping you go from zero to 100 on your freelance journey.

Niching Down to Stand Out

Al Calder: So, one thing that really jumps out from all of these sources is the idea of niching down. You know, it seems kind of counterintuitive at first. You would think that being a generalist would be the way to go. You know, you have more options. It might seem that way, but you have to think about it from the client’s perspective. Like, if I’m looking to hire someone, I’m looking for an expert in the thing that I need help with, right? Not someone who just kind of dabbles in everything. So instead of saying, ‘Oh, I’m a writer.’ You’d say something like, ‘I specialize in writing website copy for health and wellness brands.’ Makes sense. That specificity helps you stand out. Because there’s a lot of people who just say, ‘I’m a writer.’ You know, I could write anything. But then that doesn’t really tell me anything about what you’re good at, what you enjoy doing. In fact, niching down can help you command higher rates as you build your reputation. I mean, it makes sense. If you become known as the person for a specific type of service, then people are going to be willing to pay more to work with you. It’s like you’re the go-to person.

Now, in a YouTube video titled, ‘How I’d land my first freelance client in 48 hours,’ Dea adds this really interesting layer to the whole niching down conversation. She basically says, ‘You should start with something you’re passionate about, okay? Even if you adjust your niche later on, it’s like don’t overthink it too much in the beginning. Just start with something that you actually enjoy. You can always adjust it later.’ And I think that’s smart, too, because you know passion fuels your work. You’re going to be motivated. You know, get better if you enjoy it. And it makes the whole freelance journey more enjoyable. I mean, if you think about it, it’s like the difference between, you know, working on a job that you dread and doing something that you actually love. It’s just a completely different energy and that translates to the quality of your work. Ultimately, I think that attracts clients. So, you’ve got your niche, you’ve got that passion, but then there’s this hurdle that a lot of new freelancers face.

Building a Portfolio With No Clients

Al Calder: How do you build a portfolio when you haven’t had any clients yet? That’s a tough one. It’s like the classic chicken in the egg problem, right? How do you get experience if you need experience to get hired? In an Upwork article, there’s a really interesting suggestion that addresses this. They recommend creating samples tailored to your ideal clients, even if those clients are fictional for now. So, you’re basically creating work that showcases your skills and the types of projects you want to attract, even if you haven’t been hired for them yet. So, you’re kind of building a model home to show potential clients what you can do. And another article on the Medium platform takes this idea even a step further. They recommend volunteering for nonprofits to gain real-world experience and testimonials. It’s a win-win, right? You’re helping out a good cause and you’re also building your portfolio at the same time. One caveat, you should always pick organizations that you actually care about, so you’re more likely to stay motivated and produce high-quality work. Makes a big difference when you’re actually invested in what you’re doing. Okay, so you’ve got your niche, you’re building that portfolio.

Crafting a Compelling Personalized Pitch

Al Calder: Now, how do you actually land those first clients? Well, that’s the big question. Let’s get into it. The articles we reviewed for this podcast zero in on the importance of a compelling pitch. They stress that personalization is key. So, it’s not about sending out a generic template to everyone you can find, right? It’s about really taking the time to understand the client’s pain points and position yourself as the solution. You got to be like a detective, you know, do your research on the client, understand their challenges, and then craft a pitch that really shows that you’ve done your homework and that you’re the person to help. It makes sense.

Now, Dea, in her video, she actually introduces this copywriting framework that I think can be really helpful. Have you ever heard of the concept of problem, agitate, solve, or PAS? You start by identifying the client’s problem. Then you highlight the negative consequences of not addressing the problem. And then finally, you present your service as the solution. So like if you’re a freelance web designer, you might say something along the lines of, ‘Are you struggling to get traffic to your website?’ Well, you could be losing out on thousands of potential customers. But don’t worry because I can help you redesign your website to attract more visitors and boost your sales. Something like that. It’s super clear, concise, and persuasive. It’s a good way to kind of frame the value that you’re providing. Now, Dea also emphasizes the importance of repetition and outreach, even if it feels scary at first, because it’s easy to get discouraged if you don’t hear back right away. I mean, every freelancer’s been there. You know, you send out a bunch of emails and you hear crickets. Yes, it can be really disheartening, but you’ve got to be persistent.

Keep Going When You Hear Crickets

Al Calder: Dea shares this really incredible story in her video about going from charging $10 an hour to building a six-figure freelance business. It’s an amazing success story and it shows that consistency and determination can really pay off. It’s inspiring. You don’t have to start perfect. You just have to start. Just get started. She also suggests starting with lower prices to minimize risk for clients. That makes sense, right? Especially if you’re just starting out. It’s like you’re saying, ‘Hey, I’m new at this, but I’m willing to give you a good deal to prove myself.’ It’s almost like building trust in a track record. It’s about being really strategic in those early days. Just remember to boost those rates once you establish yourself. Okay, one last thing before we move on. What about these freelancer platforms like Upwork and Fiverr? Are they a legitimate route to freelance success? They definitely have their value, especially for getting started. I mean, they can be a good way to get some exposure, connect with potential clients, and even build up your portfolio a little bit, but I’d also caution against relying on them too heavily. The main concern is this. You can get caught in this cycle of competing for lower-paying gigs. And it’s like you don’t want to get stuck there. You want to be able to eventually raise your rates and work directly with clients. So, it’s almost like a stepping stone, but not a final destination. We talked about niching down, building a portfolio, crafting that compelling pitch, and even dipping our toes into the freelance platforms.

Finding the Right Clients

Al Calder: What’s next on this journey to landing that first client? Well, I think now we can kind of shift gears and talk about, you know, finding the right clients. Like, not just any client, but the ones who really align with what you’re offering. It can feel daunting, especially when you’re first starting out because there’s so many options. How do you even begin to find them? I think one of the first things to think about is your existing network. Some of the articles we looked at really emphasize this. So like former colleagues, uh people you went to school with, people you already know. Consider your work friends, family friends, family, even people in your online communities, like anyone you’ve already built a relationship with. It’s not just about what you know, but who you know. Networking is super important. And it doesn’t have to be this like scary thing. You don’t have to go to networking events or conventions. No, you can just simply send an email to people letting them know that you’re freelancing now and the type of work that you’re doing. Just putting it out there, right? And you never know who might need your services or know someone who does or who can connect you with the right people. This isn’t reinventing the wheel. It’s simple stuff, but highly effective.

So, what if you’ve kind of tapped into your network and you’re ready to branch out a little bit more? Well, that’s when it’s time to think about the dreaded cold pitch. I kind of hate the term cold pitching. It sounds so impersonal. I think it’s more strategic outreach. How do you do that strategically? Well, Dea actually has this really great approach in her video. She calls it targeting the sweet spot client. These are companies that aren’t so small that they can’t afford your services, but they’re also not so large that they already have like a huge in-house team for everything. So somewhere in between, it’s like finding that Goldilocks zone, right? The companies that are actively growing and likely need the specialized skills that you offer. And so how do you find these sweet spot clients? Well, Dea gives some really tactical advice in her video about using social media. She suggests looking at things like follower count, engagement rates, and even the type of content that a company is sharing to kind of get a sense of their size and their activity level. It’s like you’re doing a little investigation to see if they’d be a good fit before you even reach out. Some of the articles we looked at actually take a little bit more of a traditional approach to cold pitching. And they recommend focusing on crafting really targeted emails to marketing executives. Both strategies have their place depending on what you’re comfortable with. I think Dea’s approach might work better for someone who’s comfortable with social media and wants to be a little more targeted, whereas the email approach might be better for those who prefer that kind of more formal communication style. It’s about finding what feels most natural and effective for you. But no matter which approach you choose, personalization is key. No one wants to feel like they’re just receiving some generic mass email. You really want to take the time to tailor your pitch to the specific client that you’re reaching out to and show that you understand their specific needs.

Freelance Platforms as Stepping Stones

Al Calder: So, we’ve talked about networking and we talked about cold pitching, but let’s take a closer look at those freelance platforms like Upwork and Fiverr. They can all be really valuable, especially early on. They can be a great way to get your feet wet, gain some experience, build a portfolio, but it’s important to use these platforms strategically. You don’t want to get caught in that trap of constantly competing for low-paying gigs. You don’t want to get stuck there. So, it’s about seeing them as a stepping stone, not a final destination. Now, there’s one more powerful strategy that we need to talk about.

Passive Pitching: Clients Come to You

Al Calder: And this one might surprise you. It’s called passive pitching. It’s more about setting things in motion so that clients come to you instead of you always having to chase after them. You want to start by crafting a stellar profile by showcasing your skills and experience in a way that makes it really easy for clients to find you when they’re searching for someone with your expertise. It’s like optimizing your online presence to attract the right clients. Think keywords, compelling descriptions of your services, and a portfolio that really highlights your best work. It’s like setting up a shop window that’s really enticing. It requires consistent content creation and increasing your digital footprint all the time. Things like blogging, posting on social media, creating videos, all of that by consistently sharing valuable insights, demonstrating your expertise, showcasing your personality. You’re essentially creating a magnet for your ideal clients. Instead of constantly chasing clients, you’re creating a space where they can discover you. And the best part is that this content continues to work for you even when you’re sleeping or working on other projects or even relaxing on that beach. It’s like having a 24/7 marketing team working behind the scenes.

So, we’ve covered a lot of ground in our look under the hood of pitching and landing freelance clients. We’ve talked about niching down, building a portfolio, crafting that compelling pitch, even navigating those freelance platforms. And then this idea of passive pitching, it feels like a lot to juggle. At least it can feel that way for someone just starting out. But I think the most important thing is to remember that building a successful freelance career is a marathon, not a sprint.

A Marathon, Not a Sprint

Al Calder: It’s about pacing yourself, finding what works for you, and being kind to yourself along the way. Because there will be challenges, there will be setbacks. There will be moments of self-doubt. You’re going to want to give up sometimes, but it’s about focusing on that progress, not perfection. Dea’s story is a really great reminder of that, that everyone starts somewhere. She went from charging $10 an hour to building a six-figure business. That’s incredible. So, it just shows that, you know, it takes time. It takes persistence and willingness to adapt and learn along the way. And she has this really great call to action in her video. She says, ‘Get out there and earn a dollar as a freelancer. It just feels so empowering and achievable.’

Pricing Your Services Confidently

Al Calder: Okay, so we’ve tackled finding clients, but there’s another aspect of freelancing that can feel equally daunting, especially for new freelancers. Pricing. Yes, pricing. How do you determine what to charge? It can feel stressful. How do you put a price tag on your skills and expertise, especially when you’re just starting out? It feels really overwhelming. Thankfully, our sources offer some really helpful frameworks for thinking about pricing. Like Dea in her YouTube video, she’s a big advocate for what she calls no-brainer pricing. And her advice is basically to start lower than you might initially think. So, almost undercharge, especially when you’re brand new to freelancing. Why would you do that, though? Well, you got to think about it from the client’s perspective. They’re taking a chance on someone who’s relatively new. You don’t have that track record yet. So, by offering a lower price, you’re kind of minimizing their risk and making it more appealing for them to give you a shot. So, it’s about building that trust, improving your value. I want to really emphasize this doesn’t mean undervaluing yourself. It’s just about being strategic in those early days. And as you gain experience, build your portfolio and get testimonials. You can gradually increase your rates. So, start low and then as you gain more experience, you can charge more. Remember, she actually shares her own story in the video about going from $10 an hour to six figures. So, success is possible. It’s a pretty inspiring trajectory. It shows that you don’t have to start perfect. You just got to start. Just get started now. Other sources present a slightly different tactic. They suggest offering a small discount with the understanding that you’ll renegotiate the rate after an initial period. You’re kind of giving them a little bit of a break, but you’re also setting the expectation that the price will go up. It’s like a trial period almost. You get to prove yourself and then once you’ve shown your value, you can charge what you’re worth.

So, both approaches are about being strategic and flexible in those early days. You’re kind of experimenting and figuring out what works for you and the specific clients that you’re targeting. We’ve talked a lot about actively finding clients, networking, cold pitching, freelance platforms, but what about passive pitching? How does that all play into this? Well, I like to think of passive pitching as a creative system that attracts clients to you, even when you’re not actively seeking them out. Almost like setting up a magnet. You’re building this magnetic field that draws in those perfect fit clients. So, how do we build this magnetic field? Well, think of it in the context of your profile on sites like Upwork. Craft a really stellar profile, showcasing your skills and experience in a way that makes it super easy for clients to find you when they’re searching for someone with your expertise. Be really intentional with how you’re presenting yourself online. Think keywords, compelling descriptions of your services, a portfolio that really highlights your best work. So, it’s almost like setting up a shop window that’s really enticing. It includes consistent content creation across multiple platforms like blogging, posting on social media, creating videos by regularly sharing valuable insights, demonstrating your expertise, showcasing your personality, you’re essentially creating this beacon that attracts clients who are interested in what you have to offer. So instead of constantly chasing clients, you’re creating spaces where they can discover you. And the beauty of this approach is it works for you even when you’re busy working on other projects. Again, it’s like having a 24/7 marketing team working behind the scenes. So, we’ve covered a lot of ground in this look under the hood of pitching and landing freelance clients. We talked about niching down, building a portfolio, crafting a compelling pitch, pricing your services, and finding the right clients. It’s a lot to think about and it can feel overwhelming, especially when you’re first starting out. So, what’s the most important thing for someone to remember as they’re kind of embarking on this journey?

Take Action and Turn Clients Into Fans

Al Calder: Probably the most important thing is to just take action. Don’t get bogged down with trying to do everything perfectly from the start. Just get started. Experiment and see what works for you and be patient. Building a successful freelance career is a marathon, not a sprint. And it’s a journey that’s constantly evolving. The skills and strategies that you learn along the way will not only help you land those first few clients, but also set you up for long-term success. So, here’s a final thought for you as you embark on this exciting journey of freelancing. How will you not only attract clients, but also turn them into raving fans who will champion your work and refer you to everyone they know? That’s the dream right there. That’s the key and that’s something that we can definitely explore in a future look under the hood of freelancing. Until then, best of luck in landing those first clients. Thanks for tuning in to Freelance Under the Hood. If you enjoyed this episode, please subscribe and leave a review. It helps more freelancers like you find the show. Got questions or topics you want covered? Reach out to me at remoteofficeworld.com. You can also find the link in the bio. Until next time, keep on freelancing your way to freedom.

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