From Part-Time to Five-Figure Copywriter in Two Years

Sherri Caldwell

Two years ago, with my kids graduating from high school and leaving home, I began my midlife career transition to copywriting. I joined AWAI training programs and attended Bootcamp in 2015 and 2016.

Following the process in The Accelerated Program for Six-Figure Copywriting, step-by-step, to write specs, I won an AWAI Spec Challenge at Bootcamp 2015! I joined Circle of Success with that $1,000 check — an investment in my continuing education with AWAI.

In the last year, I’ve worked on editorial and direct-response projects with AWAI, and some outside freelance copywriting projects, too. But I was still working part-time as a teacher through 2016.

Fast forward to … now.

February 2017 — less than two years from the beginning of my copywriting adventure …

I just signed a copywriting Retainer Agreement — and received the first check — for a monthly amount that is more than I made (copywriting) the entire year before!

Here’s how it happened and how you could easily imitate my success …

At the very end of December, I noticed a post in a Facebook networking group for copywriters, looking for someone to write emails and other content about women’s health. I responded with a brief introduction and linked to a relevant sample on my website.

The connection with the marketing director was immediate.

We worked through a brief Spec Assignment, by email and telephone conference, and on to negotiation and agreement quickly. That part only took about 10 days, over the New Year’s holiday.

What took more time was finalizing the contract with the company’s Legal and Financial Department, three more weeks to be exact. It was AGONIZING … and felt like forever.

Fortunately, when the contract went to the company’s Legal Department for review, I went to my AWAI resources and pulled out the Business Forms package (AWAI’s Essential Templates for Your Copywriting Business program).

The AWAI templates for Contracts and Retainer Agreements gave me the confidence boost I needed as this was my very first copywriting contract. The forms gave me a better idea of what to expect, as far as contract terms and standards.

What came back from the company’s Legal Department was … a 12-page contract in the language of legalese. Or, more appropriately, legal-unease.

At first, I panicked. Then I read it through, word-by-word and out loud. I needed to let it set in and because it was late, I went to bed.

It wasn’t any better when I looked at it the next morning. But then I noticed something peculiar, a template file name on the bottom of each page. “A-ha!” The company was using a fill-in-the-blanks template.

Well, I had one of those, too! And it wasn’t anywhere near as scary and confusing.

I opened up the AWAI Retainer Agreement template on my computer. I carefully filled in the blanks with my business info and the numbers and terms already agreed upon.

I consulted a legal advisor who has a lot more experience in contracts and law than I do. We went through and modified the 12-page legalese form, crossed out sections here and there, made changes where necessary, and made a note in several places:


I emailed the contract back with the changes, with my ‘usual’ one-page copywriting retainer agreement attached … and waited to hear back …

It took a couple of days — another weekend — and more agony.

When it came back, they had agreed to most of the changes, and included my one-page agreement, nearly word-for-word (including advance payment), as an attachment to the final contract.

The negotiation, waiting, and finalization process is an emotional roller coaster. You experience every high-high and low-low in confidence as you reach out … and wait … and respond … and wait … and back and forth …

But when it finally all comes together, and you’re through that part of the process and on to the fun part of researching and writing and working with the team, it’s a tremendous boost to your confidence.

And so now the work begins …

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Published: February 23, 2017

4 Responses to “From Part-Time to Five-Figure Copywriter in Two Years”

  1. My congratulations to Sherri. I purchased The Accelerated Program for Six-Figure Copywriting over two years ago, and I am sorry to say, have let it languish, while focusing on other issues in my life. It is this story that is motivating me to blow the dust off my purchase and get busy. Thank you Sherri for sharing your story! And maybe in a couple years I will be sharing my story and motivating others.

    Bob BarcleyFebruary 23, 2017 at 12:41 pm

  2. Thanks for sharing Sherri's inspiring success, Will. When fatigue threatens me as I study the current assignment in the Companion series, I'll remember Sherri's journey and her remarkable success.

    Again, thanks, Will!

    Pat HFebruary 23, 2017 at 2:45 pm

  3. This was very helpful, I am just a beginner and hoping this program will work. Thanks for sharing!

    Sharon MFebruary 24, 2017 at 9:32 am

  4. Hi AWAI TEAM Sherri Caldwell has Success, Email copy writing is Lucrative in B2B and B2C Businesses.

    DarrickFebruary 24, 2017 at 11:39 am

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