#79: Six-Figure Freelancing: Consistently Sending LOIs and Using Upwork, with Laura Pennington Briggs

Today’s guest is Laura Pennington Briggs. Laura is a teacher turned entrepreneur, two-time TEDx speaker and freelance writer. She’s the author of the award-winning “How to Start Your Own Freelance Writing Business” and the Amazon bestseller “Six-Figure Freelancer” and the founder of Operation Freelance. 

Laura started as a freelance writer and virtual assistant in 2012. Now, she continues to write but also does book marketing and book launch strategy for authors. She started out as a part-time freelancer. But after 18 months of freelancing—only six months of that as a full-time freelancer—she hit the six-figure mark.

To get to that financial goal, Laura tracked her income and financial projections on a legal pad. 

Freelancers are often told not to go on Upwork, but Laura used Upwork to build and scale her business. In fact, she earned over $450,000 through the site over the years. But she points out that it’s important to have a strategy when you are using Upwork.

When she was a new freelancer, she aimed to get Upwork jobs primarily for the feedback, not necessarily the fee, so that she could build good ratings on the site, opening the door to better and more work. She called these her “fast, cheap and simple” jobs to deliver the service easily and quickly to get a fast five-star review. She now has more than 200 positive ratings on Upwork, which lands her good work.

You also have to know what the red flags are, such as clients with ridiculous expectations and a very long description for a simple, short project. Also, when clients tell you they’ve worked with lots of other freelancers before and it’s never worked out, that’s a red flag! You can also read other freelancers’ reviews of clients. Trust those reviews.

The two ways that have worked best for Laura to find new clients have been Upwork and emailing cold letters of introduction (LOIs). Laura says if you send 50 LOIs and only one person responds, there’s something wrong with your LOI or your strategy. It’s important to take the time to research the client and explain why you like that company. Make the beginning of an LOI personal and hook the person. Don’t use a standard template for the entire LOI, which is a common mistake.

Great tip: Laura emails an LOI, and then about 30 minutes later she connects with that person on LinkedIn saying, “Spoiler alert: I just pitched you via email.”

Remember: Your perspective clients don’t really care about you, only that you’re qualified. So keep that part of your LOI to about two sentences and focus instead on how you can help them.

Sending LOIs is also a numbers game—you need to send a lot to get responses. You cannot just send a 1–2 LOIs a week and expect to get a bunch of new clients. Laura recommends sending five pitches a week for three months, tracking them and seeing how people respond. Make it a weekly habit.

Laura is a morning person. She works in batches based on the type of work, not the client. For example, she spends time on pitches for different clients during the same time slot, not focusing on all tasks for one client before moving on to another clients’ tasks.

When it comes to pricing, Laura recommends newer freelancers take on smaller projects and try out their rate, rather than committing to a rate and a long-term contract. You should try out your pricing and make sure you feel comfortable with it. Experienced freelancers should examine their pricing every six months. Clients are paying not for your time, but your years of experience and expertise.

Laura does not commit to pricing over the initial phone call. She tells potential clients she will get back to them by email. She may be nervous to quote over the phone, but she may also actually need the time to consider all aspects of the project and what it may truly cost and entail.

Remember that you can negotiate everything, not just price. You can negotiate length, deadline, scope of work and the amount of communication (no phone calls, no strategy sessions unless they pay more). You can also give a discount if they sign a long-term contract.

Laura advises that you have to get comfortable with calling the shots. You might feel like you’re pitching yourself as a freelancer to a client, but you have to believe that you’re a CEO too and you get to decide what your company policies and deal breakers are.

Laura tried to be an agency owner for a year, outsourcing her writing to subcontractors. And she hated it. You do not have to outsource your client work if you don’t want to. Instead, if you want to scale, you can outsource certain pieces of the process, like marketing, administrative work, invoicing or LinkedIn outreach.

Biz Bite: Hire a virtual assistant


Laura’s website: Better Biz Academy

Laura’s book “The Six-Figure Freelancer

Laura’s podcast: Advanced Freelancing

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