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[WORKSHOP] Pitch to Paycheck: 5 Strategies to Land New Work

How to find work as a freelancer.

Business as usual is long gone. Especially when it comes to finding work.

Approximately 38% of the workforce is currently engaged in freelance work. Within the next five years, that number is expected to increase to 50%.

This creates a problem. Working as a freelancer requires a very different set of skills than just being a good employee. If you’re a freelancer, you’re running a business – even if that business is just you.

Your skill is your product. In my case, I’m a writer. I’m in the business of selling writing. If I want to be successful, I have to find people who want to buy my product.

Like any business, that’s easier said than done.

I’m a writer. Writing is valuable, but not all kinds of writing are valued the same. The market may not want or need your skills or what you have to offer. ChatGPT won’t do a very good job writing a novel, but it can write a pretty good SEO article that ranks for a specific keyword.

You have to put yourself into the market to understand what it’s looking for and what you have to offer.

This workshop will dive into five strategies you can use to see what the market is looking for and land work for yourself. While it’s geared towards freelance writers, the underlying skill of developing a product and selling it is the same in any industry.

These strategies can be adapted for any profession and can help you find work whether you’re a full-time freelancer or are starting a side hustle.

The more economic buyers you can identify and find in the market, the more chances you’ll have at finding success.

This workshop will cover:

⚡How to generate new work

⚡ The best places to look for clients

⚡ How to set rates to make yourself competitive

⚡ Tools you can use to up your game

Strategy #1: Pitch the Right People

How many jobs have you applied to without getting any response back?

A lot.

The same thing happens with freelancing. Just like you’re supposed to tailor your resume and write a cover letter for the job you’re applying for, freelancers have craft pitches to sell their product.

For writing, that entails coming up with a unique story and angle, identifying an editor to share it with, finding their contact information, and drafting a succinct email that convinces them to buy your article.

It’s a lot of work. You can spend hours sending out pitches and not a single one could bite. As a freelancer, you eat what you kill. If no one buys your work, you’re going to go hungry.

When I started freelance writing, I signed up for several different freelance job boards and newsletters. These are great resources, but I think most freelancers are using them wrong.

If you’re receiving a free newsletter with a bunch of pitch opportunities, chances are a few thousand other freelancers are receiving the same email.

You can have the best pitch but if you’re competing with a bunch of other freelancers, the editor you’re pitching probably isn’t going to see your email.

Instead of responding to pitch openings like everyone else, focus on building rapport with editors and content managers who can buy your work.

Here’s what you can do:

  • Send a connection request on LinkedIn

  • Find their email and send them a letter of introduction

  • Ask if they’re accepting pitches and if so, inquire about what they’re looking for

  • Share a few samples of your work

Last fall I saw a pitch announcement in a free newsletter that I was subscribed to. Rather than following the instructions to submit a pitch, I reached out to the editor directly. I sent her an email telling her who I was and shared a few samples of my work.

Email

A few weeks later, she was looking for help and reached out to me. My background fit with her needs and I won the work.

Use freelance newsletters and job boards to identify who’s hiring in the market. Then find the right people to reach out to who can actually pay you.

Strategy #2: Create a Contact Roster

You might not think of yourself as a salesperson but these days we’re all salespeople.

Responding to job positings and freelance inquiries is one way to get work, but it isn’t the only way. You can use outbound sales tactics to find work too.

Instead of spending hours crafting unique pitches, create a contact list of managers and editors that you can proactively reach out to in the future. Connect with them and send them an email introducing yourself.

By doing this, you give someone the opportunity to work with you in the future even if they aren’t actively looking for help right now.

I started freelance writing in the personal finance space. I’ve mostly written SEO blog posts and newsletters but I’ve been looking for new experience.

I made a list of industry trade publications that provide content to financial professionals. I found contact information for editors at each publication and sent a cold email introducing myself.

One individual got back to me and offered me $1,000 to write a 1,500 word article! Not only is it a new opportunity, that rate is well above what I get for SEO blog posts of a similar length.

Strategy #3: Pitch the Right Publications

Not all publications – or employers – are created equal. Some pay more, some pay less.

Your job isn’t to pitch anyone who’s willing to pay you. Your job is to find work that you want to do and will compensate you for the value you provide.

Most writers who submit pitches are doing so to publications where their content is the end product. A newspaper, magazine, or website that provides content to an audience as their primary source of revenue isn’t going to pay very well.

Instead, look for work at publications where your skill is a service.

A lot of companies have blogs or newsletters as part of their overall marketing strategy. Take Hubspot as an example. Hubspot is a software company that provides tools for organizations who need help with inbound marketing. Hubspot’s product is their software.

Hubspot produces several blogs and newsletters. The content they publish is a service rather than a product. Because of that, they can afford to pay writers more than a website like Business Insider (which I’ve written for) can pay because their product is their content.

These are some examples of publications you can write for that probably aren’t actively soliciting pitches but regularly work with freelance writers:

  • Blogs and newsletters for SaaS products

  • University alumni magazines

  • Industry trade publications

  • Consulting firms looking for white papers and internal reports

  • Conferences that need help with marketing collateral

Find the contact information for decision makers within these organizations and add them to your contact roster. Proactively reach out to see if they’re looking for help. If they are, position yourself to be the solution to their needs rather than just another unsolicited pitch.

Strategy #4: Know Your Value

There are only 24 hours in a day and of those 24 hours you’re hopefully sleeping for at least eight of them.

The point is time is limited. You only have so much time to spend selling your work and then making good on actually doing it.

To prioritize reaching out to the right people at the right publications, you need to know your value. If you don’t, you’re not going to know when to say yes – and more importantly, when to say no – to work that isn’t a right fit.

Last year I lost a lot of my freelance writing income. I started pitching publications willy nilly and responding to the postings that I found in freelance newsletters. I got a gig writing for a website that only paid $70-$120 per article.

I track my time religiously. Even though most of my clients pay per word or per project, I know how long it takes me to complete assignments and thus how much I’m worth. Even though the work was paid work, it was a fraction of the hourly rate I was getting from my other clients.

Spreadsheet

The more time I spent producing work for this site, the less time I had to find better work that aligned with the value I had to offer. It drained me mentally and it didn’t take long for me to begin resenting the company. (Fortunately, they went belly up within a month of bringing me on so we parted ways naturally).

If you don’t know what you’re worth, you’ll be taken advantage of. As more and more people go freelance, there’s going to be a ton of labor in the market. For some types of work – like SEO content – I think it’s going to be a race to the bottom for wages.

Keep track of your rates. I recommend Clockify as a tool to track your time. Create a spreadsheet to measure how productive you are and how much your time is worth.

Doing this will not only allow you to say no to low-paying work, it’ll give you a figure you can use to negotiate new work with people you reach out to from your contact roster.

Strategy #5: Use AI

AI is going to take a lot of jobs. But it isn’t because AI is a better writer. It’s because someone out there is spending time learning how to use AI within their existing writing process to produce better work.

Learn how to use AI to your advantage.

When it comes to finding work, you can use tools like ChatGPT to brainstorm ideas with you. It can help you identify publications to pitch to, contact information for editors at those publications, and help you refine your cold emails before you hit send.

Writing is my second career. I didn’t go to journalism school and I have no idea what the protocol for pitching is. I’ve just been winging it as I go.

Because I don’t have a writing background, I don’t always know who to reach out to within an organization. There’s associate editors and managing editors or growth marketers and content marketers. I don’t know who’s who in the zoo.

I’ve used ChatGPT to help me figure out who to send my emails to. It has recommended potential clients to work with and the job titles of decision makers within companies that I should reach out to.

ChatGPT

This saves time, allowing me to reach out to more people that I would otherwise be able to.

Recap

Don’t

❌ Apply to freelance job listings

❌Apply for the same gigs as every other freelancer

❌ Look for gigs where your deliverable is the final product

❌ Take jobs where you’re paid less than you’re worth

❌ Use ChatGPT to do your work for you

Do

✅Pitch editors who have the ability to hire you and pay you

✅Build an outbound contact roster

✅ Look for gigs where your content is a service and not a primary source of revenue

✅ Keep track of your rates

✅ Use ChatGPT to supplement your work

By using these strategies, you’ll be able to connect with more people who have the ability to hire you and pay you for your work. The more you sell your skills and find buyers who want to work with you, the more successful you’ll be.

Resources

Freelance Job Boards

Pitching editors from a job board might not be the best way to find work, but these job boards are a good way to find out who is hiring and what they’re looking for. Here are a few job boards to subscribe to if you aren’t already:

✏️ Six Figure Writing Jobs

✏️ Placed

✏️ All Things Freelance Writing

✏️ Freelance Framework

✏️ Freelance Opportunities

✏️ Write Jobs PLUS+

Freelancers to Follow

Getting started freelancing can be hard. Here are some freelancers who provide insights on how to be successful as a freelancer.

✏️

✏️

✏️ Jen A. Miller

✏️ Kaitlyn Arford

✏️

Book Recommendations

📚The Money Book for Freelancers, Part-Timers, and the Self-Employed

📚Notes From a Hired Pen: How I Made $135,000 in One Year of Freelancing

Tools

⏱️Clockify

What would you recommend?

These are some of the resources and strategies I’ve used to find freelance work but I would love to know more about what your experience has been. Share your feedback in the comments 👇

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