Freelancing can be a paradoxical existence. We exit the world of full-time so we can spend more time doing exactly what we love; yet we can end up spending even less time doing what we love because we’ve got to run the business. Your passion and skill is nothing without having actual work to do or money to do it.  In comes the skill that everyone needs yet no one cares to work on: Pitching.

Pitching can be a fearful practice, but we’ve all done it before. Another word for a pitch would be a job application. We’re using the word pitch because you’re a freelancer and not an employee, but the principles are the same; a series of sentences, however long or short, to describe what it is you do and why a client should hire you. In some contexts you might call it a cover letter. Whatever you want to call it, the better you get at it, the more time you’ll get to spend on the work you love.


Any freelancer reading this knows that sending 30 pitches a day for weeks, trying to make them all unique, remembering which goes to which company, and making sure a cute fact about that company is in the pitch somewhere, is truly soul destroying. You don’t want to get stuck in a pit of job applications. That’s why it’s so nice when clients start offering you work. But even if that happens to you often, we all have to pitch now and then. The only way to really pitch in high volume is to create a template and change it slightly for every client. You don’t want to do that, which is why you simply shouldn’t send pitches in high volume. Be selective with the clients and jobs you pitch for. If you’re new to freelancing, this may seem like a privilege. It isn’t. No matter how niche your services you will never run out of jobs to apply for. Freelancing is only becoming more popular so don’t worry about missing an opportunity. Be as picky as you can be so that you can give real time and effort to every pitch you write. It's okay to have some pre-written material, as there will likely be some overlapping information from one pitch to another, but make sure to continually review that pre-written material so it’s up to date.


Who is it you are trying to convince? Pitching a labor union is going to be different than pitching a health and wellness company. Of course their needs and priorities are different, but these companies’ brands will also inform how you present information to them. Are they light, goofy, and humorous, or are they professional and to the point? It’s important to do research into more than just the business itself, but the brand, their marketing, and their company culture.

It doesn’t take much to acquire a wealth of knowledge about any one person or company these days (slightly creepy, but we can use it to our advantage). Checking out a client’s social profiles is an essential part of your investigation, as is checking their reviews on Glass Door or Yelp (depending on the business), and doing a basic google search. What’s their work history? Where are they located? What news do they read? A lot This information may seem peripheral, but it can be incredibly useful when building a pitch or presentation. It can inform you as to how they best absorb information and what comedy they might like. If you want to make a pitch funny you better be sure what their sense of humor is like. Of course, you don’t want to get too casual. Even if you find loads of information on a person, you don’t need to bring it all up. They don’t need to be reminded of their prom photos when considering a new contract.


So you’ve chosen a client you are willing to spend time creating a good pitch for and you’ve done adequate research. It’s time to write. Starting with a blank page is tough for anyone no matter what you’re writing. Fortunately, you’ve probably written hundreds of pitches before so start with one of those. “I thought I was supposed to make all my pitches different?” Don’t worry they will be. The fact is, you don’t have infinite time to work on this pitch and whatever gets you going quicker is worth it. Even if you only end up using one word of an old pitch, it will help them get the gears turning.  

No matter what medium you are using to contact a client, Upwork, LinkedIn, Toptal, or straight up email, the construction of a pitch stays very much the same. Why are you contacting this client? Why are you interested in this opportunity? A little a bit about you. What about you is perfect for this role? What about you is different from other freelancers? Conclusion. Generally in that order. Now often a lot of this information is in other documents like a resume or a profile. Make sure not to repeat yourself in your pitch, give new information. Your pitch isn’t a list, it’s a story. Finally, you aren’t just writing lots of pitches, clients are reading tons of them (most of them shitty), so make sure yours is short, to the point, and somehow different (it’s the best way to catch their attention).

Becoming a great pitchman is a sure-fire way to do more of the work you love.