#79: Six-Figure Freelancing: Consistently Sending LOIs and Using Upwork, with Laura Pennington Briggs
11/12/20 • 45 min
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
Resources:
Laura’s website: Better Biz Academy
Laura’s book “
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
Resources:
Laura’s website: Better Biz Academy
Laura’s book “
Previous Episode
REPLAY: #27: 10 Micro Habits to Improve Work-Life Clarity
On today’s show I am going to outline 10 micro habits that you can consider implementing in your life to improve your work-life clarity.
Building habits into my life helps me commit to work-life clarity. Micro habits are tiny, incremental things you can start to do that seem so incredibly easy that you might just continue to build them. And, if you find they are working for you in some way, they might grow into larger habits and eventually habits you don’t even think about.
Not all of the micro habits I’m recommending are directly related to your business. Your life and your business are intertwined. Plus, I think we should all be focusing on our health. So, some of these will be healthy micro habits, and some will be things that will lift your energy and put a smile on your face.
I’m not recommending you implement all 10 of these micro habits. It’s better if you start small and just try a few of them. Plus, some of these might not be relevant for your individual life or may not interest you. But I hope they will spark your own ideas of what micro habits you can try out.
1. Brush your teeth after dinner.
I first heard about this micro habit as a recommendation on the Happier podcast with Gretchen Rubin. The idea is if you brush your teeth after dinner, you will be less likely to eat again that evening.
2. Set an alarm for bedtime.
3. Listen to a podcast in the morning.
4. Take a lunch break—and do it without your phone.
5. Play with your pets.
6. Learn something new in five minutes a day.
7. Text one important person in your life each week.
8. Drink one glass of water in the morning.
9. Meditate for one minute each day.
10. At the end of your work day, take 5 minutes to write down how you felt about the day.
Biz Bite: Download Restaurant Apps
The Bookshelf: “Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones” by James Clear
Resources:
Happier podcast with Gretchen Rubin
Duolingo language app
Next Episode
#80: Six-Figure Freelancing: Writing B2B Tech Content, with Satta Sarmah Hightower
Today’s guest is Satta Sarmah Hightower. Satta is a journalist-turned-content marketer who lives in Boston. She produces content for agencies and brands in the industries of technology, health care IT and financial services. She previously worked for AOL and the Tribune Company and holds a bachelor’s degree in journalism from Boston University and a master’s degree in journalism from Northwestern University's Medill School.
Satta became a full-time freelancer in August 2014 after her second layoff in five years. She realized early on that she could make more money writing B2B content than doing only journalism. Then, she realized she was good at, and enjoyed, writing about B2B technology.
In 2016, Satta hit her goal to make six figures, during her second full year of freelancing. It had been a goal after she came close to that mark in 2015.
Satta believes it’s important to balance higher-earning client projects with your own passion projects, such as coaching, essay writing or podcasting. For Satta, that means developing her fiction writing by taking online fiction writing classes through GrubStreet in Boston.
Satta won’t work for free or do unpaid tests. In fact, she doesn’t like to do any test projects because her resume, clips and experience should be enough for a client to assess whether they want to work with her.
It’s difficult to earn six figures if you’re focused on lifestyle journalism and content (parenting, fashion, health and wellness). The niche is saturated with writers, which brings down the rates. You can still write on these topics, but Satta suggests mixing them in with other, higher-paying niches, such as technology, health care or financial services.
Be easy to work with. As someone who also assigns articles for her clients, Satta has come across too many freelancers who miss deadlines, are hard to reach and/or difficult to work with. Be collaborative with clients and communicate in advance if you run into challenges.
Satta struggles with turning off work at the end of the day. To be present with her young son, it helps her to physically separate herself from her workspace and her work tools. This means sometimes leaving her cellphone in a different room.
Satta is a very early morning person. She often starts her workday at 4:30 a.m. She does this partly to get her work done early so her husband can watch their son in the morning before she takes over in the afternoon. She also knows that she can write easily very early in the morning but struggles to write late at night.
She works about 5–6 hours a day and reserves Fridays for administrative work, recognizing that her brain is tired from writing by the end of the week. She also tries to reserve personal errands and chores for the start or end of the work day, not the middle of the day.
Satta doesn’t work for hourly rates because they penalize her for being efficient. She works for flat fees or retainer agreements. But she does have an “internal hourly rate” that she aims to earn. Tracking her hours and having an internal hourly rate helps her know how to price projects and know whether a proposed fee is fair for her.
Ongoing marketing is crucial to keep the work coming in. You can’t start marketing only when work dries up. Satta gets a lot of work through referrals, including from other freelancers. Working with agencies is helpful because one editor can refer you to other editors at the same company.
LinkedIn is also a good way to get clients. Keep your profile up to date with relevant keywords, and post your work on LinkedIn so potential clients can see that you know certain topics or have worked with certain clients.
Satta tried having a virtual assistant, but it took time to train the person, plus she realized she didn’t want to be anyone’s boss. She prefers the “consultant model,” in which she outsources tasks to third-party services like a transcription service or payroll provider.
Biz Bite: Use an email scheduling tool.
Resources:
Book: “Little Fires Everywhere” by Celeste Ng
ASJA (American Society of Journalists and Authors)
Temi transcription service
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