How to Pitch Yourself to Get Freelance Work


May 6, 2020


We're expanding on the art of the cold pitch because well, it's kinda scary, it takes a bit of chutzpah and you risk the uncomfortable feeling of rejection. But when you really need work and the long game won't work for now, you've got to get out there and go get it.

How do you master the art of the cold pitch? Why aren't you getting any replies? How do you follow-up without being annoying?

This quickstart guide is written with freelancers in mind but it applies to anyone who writes cold emails in the creative industries, from the writer pitching to write for a blog to a brand asking for a sponsorship request. We’re going to cover some basic universal-ish principles that will sharpen your freelance toolkit, whatever work you do.

First things first: the most important aspect of the cold pitch, in my humble opinion, is empathy. Empathy is the superpower soft skill that gets so overlooked but is the undercurrent of so much that is good and right in the world, from how we connect with others to how we work together. And it matters a lot when it comes to getting clients. All anyone is trying to do is their best. Most people aren’t mean-spirited on purpose.

And if you want to get your work out into the world, work on some cool projects and make some money, the best thing you can do is learning to put yourself in someone else’s shoes.

It’s really the secret to not only successful pitching (reading the room, understanding needs, tailoring your approach), but also the secret to being consistent with it and not taking things personal when you get a rejection, no response at all, or worst of all, a seemingly enthusiastic response followed by the ghost. It’s (probably) not you.

How you feel about things affects so much of whether or not you continue with it. Perseverance is tough but more than talent and more than luck (which is kind of a byproduct of perseverance), it matters. Even though the act of pitching seems somewhat monotonous and repetitive, it can take a lot of emotional willpower to sustain over time.

But it can lead to great things: many success stories weren’t “they came to me” or even “I asked once and got it”. Pulitzer-prize winner Gone with the Wind was rejected 38 times before a publisher said yes.

So take control of what you can and get into the right mindframe for successful pitching: how can I best add value and communicate that? If you start with empathy at the core of how you communicate, a lot falls into place: you’re probably not sending walls of text because you want to be respectful of someone’s time, and so getting to the point and to the value of what you’re pitching as succinctly as possible just makes sense.

Here’s another secret: there’s a lot of talented people out there who pass the first screen (“Yeah this person would probably be great”) but can often be left hanging in inboxes for eternity because other things take priority and other things get in the way, or a new slew of people come pitching, bringing the “I meant to get back to this person” mental note from the top to the bottom of the neverending pile of things to do.

You. Have. To. Follow. Up.

Don’t worry about being annoying but know when you should probably redirect your energy elsewhere. I generally cap it at two follow-ups spread out over time; three follow-ups in two weeks is too much.

On the receiving end of pitches, I’ve found that those that follow up separate the pile and makes it easier for me to make decisions - when I have a whole bunch of great and talented people to work with, any way that helps you stay top of mind makes the process more clearcut and simple.

As an example, out of the most recent writers we’ve commissioned to write for SuperHi, 80% had followed up. Of course, that doesn’t mean that following up will save a bad pitch or the wrong fit - but it does help if you are the right fit and have nailed your pitch.

Okay, now that we’ve set the stage (yes to empathy and yes to following up), let’s tackle the basics.

What goes into a successful cold pitch?

Keep it simple and brief

All you need is a little bit about yourself and something that shows that you’ve tailored your pitch to help bridge the gap between being person A,”random person who wants something from me”, to person B: “this person could add some value”. Even if you’re a writer, and no matter how elegant your prose is, consider your audience. Their job probably isn’t email-reader. They’re just trying to do their actual job, reading emails just one tiny part of it.

So keep it as brief as you can, while saying what you need to say. It’s not really the time to leave anything to the imagination but you don’t want to send an email that makes someone tired just looking at it. They’ll skip to next.

The rule of internet writing is a good guideline to keep in mind: paragraphs should be short, one to two sentences max each.

Address it to a person if possible, but if you can’t find a name or are unsure, a simple and friendly “Hello SuperHi!” will do. Also, name-dropping, as silly as it sounds, works. If you have some sort of connection with who you’re pitching, whether it’s through a person or a company you’ve worked for, mention that.

But how do you say what you want to say? There are a lot of weird psychological tricks growth hackers have apparently come up with that I’ve been on the receiving end of (for example, guilt-tripping people into responding - “I guess you’re not interested in growing your business” - or teasing them with mystery to get a response because of the so called “foot-in-the-door” sales technique) but there’s a huge risk to taking this path because the more people who do this, the less of an invisible trick it becomes and more into a “oh geez, not this again”.

It feels a bit sleazy. Let’s just keep it real and write like people do.

“Keeping it real” can depend a bit on your industry and even your personality. But it’s about being professional yet human. Here’s a general outline of what a pitch could look like:

  • A greeting

  • An introduction: Who are you and why are you writing?

  • Your “pitch”: Ideas for what you can do for this person/brand/company

  • Your work: Samples to paint a picture of your style, voice, point of view, etc. (more on this in the next section)

  • A call to action: Don’t make the “how” of working with you a mystery. What’s the next step?

And that’s it!

The only little bit of psychology you may want to use is the art of a genuine compliment. So maybe call me a hypocrite but it’s a nice way to make people feel good and show them that you appreciate their work - after all, isn’t that part of why you want to work with them? Don’t be afraid to connect on that level. No matter how often it happens (probably less than you think it does), a genuine compliment never goes unnoticed.

Most people are too busy or wrapped up in their own work to vocalize their appreciation for others (even though we often think it - I’m guilty of this too), and so many people are stuck in a cycle of feeling under-appreciated and overworked.

You don’t need to write a love letter: one sentence is plenty.

Share your most relevant work and then your best work

Okay, so firstly: yes to showing your work. There are pitches floating around that are basically a version of “I do x. Would you like to work with me? If so, I’ll send you some examples of my work.” And while it’s possible that some very non-busy people prefer to receive pitches like this, it’s a bit of a gamble. Why make it harder to work with you? Why make someone do extra work? So please, show your work.

Now that we’ve established that baseline, what work should you show? And how do you show it?

Again, people are busy so there’s no need to inundate anyone with all your work. Personally, my preferred method is linking to specific projects that are the most relevant to what this potential client may be looking for, to give them a sense that you could fit in and fit in well with what they’re trying to do.

Pro-tip: if you’re linking projects, share a very brief description and make your link text descriptive - in most email clients, links are by default, a different color, so if someone’s skimming your email, make sure that your links catch their eye. They may not read the rest in detail unless something piques their interest.

And if your work is visual, you could also attach a file, but that can be risky as some people are hesitant to open up large files (it’s that extra bit of effort it takes to download something) and you could even be filtered out by some email clients as spam. Sharing links (even ones to private URLs, such as a Dropbox or Notion link) is generally safer.

Then, you can always link to your broader portfolio which should contain a more general scope of your best work. (And if you’re not already doing it already, make sure this link is in your email signature - it’s the first place people look if they can’t immediately find your portfolio.)

Depending on what kind of work you’re looking for, you may also want to include ideas of how you can work together. I find that pitching yourself as versatile and a jack-of-all-trades is less likely to wield results as pitching yourself as doing one, specific thing that you know this company needs and is looking for - although, that could depend a lot on the type of company you’re pitching and your work experience. But generally, I like to go with specificity (yes, ha ha).

What are you best at? What kind of work do you really want to do? Start there, and let your portfolio do the rest of the talking when it comes to future possibilities.

Write to fit the tone of the audience and person you’re pitching

One of the things gatekeepers are on the lookout for is the very vague concept of “getting it”. It’s hard to quantify this but it roughly translates into being able to speak their language.

So, look at the tone and voice of the brand. Who are they? What do they sound like? What do they believe in? What’s their vibe?

This one’s sometimes tough because it brings up some questions like: Why do I have to change myself to be liked? Shouldn’t my work speak for itself? Or, isn’t it inauthentic to pretend to be something I’m not?

But I think that’s a personal decision you have to make. In an ideal world, we’d all only pitch ourselves to do the work we all truly believe in but when circumstances are tough, your best bet is not the shotgun approach. It can work, especially for certain fields such as illustration where visuals speak so much louder than words, but for most other kinds of work, you’re selling yourself on being a culture fit too, just like you would with a job. (I also think that so much of what we perceive as authenticity is really just learned behavior that may or may not be a true representation of who you are, so there’s that.)

Why isn’t anyone responding to me?

If you don’t hear back, it’s not because they don’t like you or that they think you’re annoying. Out of the various types of pitches I’ve received, I’d roughly estimate that fewer than 10% of pitches land in the “This is terrible” category. Things that could land you in that rare group:

  • No introduction whatsoever

  • Lack of attention to detail (ie tons of typos)

  • Too many hoops to see your work

  • And again, giant walls of text

If you suspect that you might be in that category, you need to finesse your pitch first. Ask a trusted friend, maybe someone who works in the industry, to proof your pitch.

And if you think you’ve got it right, then it might come down to a) not being the right fit or b) not following up. When it comes to following up, a 2-4 week timeframe feels right for enough time to have passed where it doesn’t feel premature.

Keep going

The internet is a noisy place and the downside of accessible communication is that it’s so easy to ignore even very good work. Sometimes it’s worth thinking outside the box to explore other creative approaches to pitching: direct mail pieces, pitching on social media, super tailored promotional projects. (An idea for another article?)

But for now, there you have it, a quickstart guide on mastering the art of the cold pitch. For more on how to get clients including setting yourself up for long-term success, check out The Creative Freelancer’s Guide to Getting Clients. If the art of a pitching is the more immediate sales side of freelancing, working on your internet presence is the marketing side of building a thriving freelance practice.

If there’s anything left to say here, it’s this: keep going. That beautiful next gig, amazing next client, or the next project that’s going to pay your rent - all of it may just be one email away.

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About the author

Ana Wang was previously the Head of Content at SuperHi. She is an ex fashion designer and copywriter who ran a whole bunch of ecommerce stores and brands and then helped other people run ecommerce stores, then helped other people help other people run ecommerce stores. Now, she's a creative generalist who plays with different mediums to tell stories.

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