5 tough lessons I learned as a novice freelancer that cost me thousands in potential earnings

5 tough lessons I learned as a novice freelancer that cost me thousands in potential earnings
Mary Kearl.Courtesy of Mary Kearl
  • Mary Kearl is a professional freelance writer and marketing consultant.
  • When she first began freelancing, Kearl says she made mistakes that cost her thousands in lost potential income.
  • Now, she asks for partial deposits from new clients, confirms rates and budgets upfront, and avoids unpaid tests.

I began my freelancing career while I was still a journalism undergrad and held numerous side gigs throughout my 20s and early 30s as I climbed the ladder in social media, content, and marketing roles. Finally, at 32 I decided to leave my full-time career behind to give freelance writing and marketing consulting a try.

Initially, my goal was simply to travel with my family for a year while working remotely to help offset the cost of visiting 12 countries. But once I got the taste of being able to set my own hours, choose my clients and projects, and determine my own rates, I was hooked.

Of course, it wasn't - and still isn't - always easy. I'm continuously learning how to run my business more efficiently, to set both my clients and myself up for success.

Along the way, I've definitely had some challenges. Here are some of the key financial lessons I've learned, that cost me thousands of dollars in wasted time and potential lost income,my advice for avoiding these kinds of issues altogether.

1. Not seeking out partial payment upfront for new smaller clients

Many of my initial freelance gigs were with major companies, such as Adobe, Zillow, and Target, with formal processes for handling everything from freelance contracts to the invoicing and payment process. While everything was largely on their terms (not mine), I almost never had to worry about chasing down payments.


It wasn't until I began branching out to work with smaller companies, startups, and solopreneurs that I learned the hard way what I needed to do to ensure I'd be fairly paid.

One of the most important lessons: Whenever possible, when onboarding new, smaller clients, I ask for a 50% deposit upfront for the first project before I begin working.

I began to do this late in 2019, after I'd created a social media strategy, a content calendar, and social media posts for a startup marketing agency client who ghosted me. First, the project was put on hold. Next, my contact stopped responding to my calls and emails about the project and invoicing for the work I'd done. Then the in-house email they'd created for me stopped working. I tried various routes to track down payment, to no avail.

This may be an extreme example, but if I'd asked for a partial payment upfront I'd have $1,000 extra dollars - at least 50% pay for the work I completed.

Since then, I now ask for deposits upfront. In an initial introductory call, I say something along the lines of, "My terms for kicking off new projects with new clients include a 50% payment upfront before I begin working on the assignment."


Now that I ask for partial payments upfront, I'm a lot less worried about getting paid and can focus on producing high-quality work.

2. Participating in multiple rounds of interviews before confirming budget and rates

When I first started freelancing, I had mixed success securing work with new clients. Some knew what they were looking for, what they were willing to pay, and that their needs and budget aligned well with my skills and compensation expectations.

For others, it seemed like I had to jump through a series of hoops - calls, test projects,, and writing proposals - before I even could find out if I was a good fit. And most times after investing this time upfront, I simply never heard back.

For one B2B startup that was looking for social media support, I went through four rounds of interviews and completed an unpaid content strategy test. In total, I probably spent six to 10 hours pursuing this client before they ultimately went with someone else who charged less.

These days whenever I get in contact with a potential new client, I thank them for their interest and ask them about their budget right away before even getting on a call. Here's a sample reply I've used to save myself and potential clients time and quickly eliminate opportunities that aren't a fit:


Hi [Name],

Thanks for reaching out and for your kind words. The opportunity to collaborate with [Company name] sounds exciting, and I'd be interested in learning more about the chance to help out with your needs. Can you share what budget you have in mind [for XYZ project] to make sure we're in the same range?


3. Doing unpaid tests instead of paid test projects or sharing my most relevant samples

After years of freelancing, I now better recognize the value of my time, experience, and capabilities. As a result, I only pursue opportunities with clients who will accept my most relevant samples or are willing to pay me for a trial project.

Completing paid tests helps me land steady copywriting and content marketing work, and also helps me get a feel for whether the projects are a fit for my interests and skills.


Even if you're just getting started, you can create sample work for your own website or social media. Platforms like Medium are great ways to demonstrate knowledge of a particular topic or in-demand skill and may even generate inbound leads after people see your work.

4. Not sharing the most relevant work samples

When I'm chatting with a potential new client, I try to share with them the most relevant examples of my past work. I drill down to samples that highlight my experience with a similar:

  • Type of company (whether a B2B business, B2C brand, nonprofit, etc.)
  • Size company (such as startup versus corporate)
  • Type of skill or service they're looking for
  • Industry

For instance, if a company is a mid-size B2C brand in the wellness space looking for general marketing support, I can share samples from my time working for two healthcare startups, marketing for three health publications, and serving as the social media lead at the New York City Marathon.

The more niche a company is, the greater relevance and industry expertise they're usually looking for.

5. Being too generic when pitching to new clients

"I'm a seasoned [freelancer offering XYZ general skills] with X years of experience who has worked for XYZ well-known [but general] companies, and I'd like to help [name of company]."


That's an OK pitch, but with some simple tweaks it could be a lot more effective.

After all, potential clients don't all necessarily care about the work you've done for just any other company, no matter how much you name drop or refer to your number of years of experience. That's because just like any other type of customer, they don't want to be sold on your product features.

Instead, they want to be sold on the benefits of your product - that is, the benefits of working with you as a freelancer - and be assured that you're the best person to meet their needs. So, flip your pitch from being focused on you and your general experience, and instead center it on the company's specific needs and how your expertise matches up.

Generic pitches similar to the one above have cost me landing paying clients, so I've updated my pitch to ensure I'm focusing on the specific needs of the customer, not just stating accomplishments to be impressive. Here's what I say now:

Hi Name,


I see that [Company] is looking for [specific type of freelancer] with an understanding of [industry niche, such as SaaS] and [specific skills, such as content strategy] I'd be happy to help with your [specific needs]!

I have worked with [well-known companies within a given niche] and have [specific skills you're looking for]. Here are samples of my work [specific to the company, industry, niche, and skills desired].

Thanks for the chance to collaborate!