I was reading a post about a new freelance Copywriter (who had some pretty impressive early success) today and it got me thinking about risk and reward.
Itās something we all need to think about when it comes to deciding whether to take the plunge and write copy full-time for a living. Itās a big and often life-changing decision - it certainly was for me.
In some respects, you could say this particular writerās rapid progression was unusual, but on the other hand, it could and does happen all the time. If youāre in the right place, in the right copywriting niche, at the right time thereās no reason it couldnāt be you.
First, let me fill you in with the background to the story, then the big decision that had to be made.
Read to the end, thereās a twist in the tail (and a useful resource) in todayās newsletter š
The backstory
Our story concerns Elanor Paterson, a relatively new Copywriter working in the fintech space.
For anyone whoās unsure what fintechās all about, hereās a description I found online:
Computer programs and other technology used to support or enable banking and financial services. Fintech is one of the fastest-growing areas for venture capitalists.
Elanor had about a month of freelance copywriting experience under her belt, and in that time, she had completed two jobs for two different clients. The first copy she wrote at $80/hr and the second she had pushed her price up to $100/hr and was pleasantly surprised there was zero pushback on the higher rate.
Sidenote: In the fintech space, assuming Elanor is a good writer (and it sounded as though she was) sheās still underpriced at $100/hr.
The last bit of the description of fintech above goes a long way to explain Elanor's early success in her fledgling copywriting career. Sheās working in a space thatās very much in demand - something to take note of if youāre deciding where to lay your own copywriting hat - go where the money is.
Elanor landed both her clients through LinkedIn, and she was sure there were many more where they came from.
So far it was looking really good.
Responsibilities, risk & reward
Before we get to the big decision Elanor had to make, a little background that has a huge bearing on the course she chooses.
Elanor had previously been in full-time employment before taking the plunge and becoming a full-time freelance Copywriter. She understood the risks, but was determined to do it,
Her husband was a full-time student, so she was the only breadwinner in the house and she was supporting him in his studies - this was a fact that weighed heavily in the difficult decision Elanor was about to make. She only needed $60-65k a year to meet their needs for clothes, food, health insurance, etc.
In the early stages of Elanorās copywriting career, the risk/reward part of her decision to go copywriting full-time seemed to be panning out. Even more so, she thought, if she could steadily increase her rates, which, as Iāve already said, she definitely could.
Eleanorās big decision
Elanorās quick success had not gone unnoticed on LinkedIn.
She was approached by a recruiter who told her that if she was prepared to write full time for a client of theirs (an employed position) there was a salary of $110, 000 p.a. on the table.
Obviously, the possibility of a guaranteed $110k against a new and uncertain copywriting career had Elanor caught between a rock and a hard place. Her head was buzzing, she had to weigh up the pros and cons of her situation, they looked like this:
Pros
The job would mean stability for her and her husband.
The salary would more than cover their expenses.
Sheād have a steady flow of work without having to chase down new clients.
Cons
She had just left a full-time job, would going back to one so soon be a āfailureā she could live with.
Did she really want to be tied to a desk between 9-5 (she assumed she'd have to be)?
She felt invigorated by her success so far and the thought of going back to a paid job didnāt have the same challenge associated with it.
When I read Elanorās story, she still hadnāt made a decision one way or the other, she was asking the readers on the forum for advice.
The question is, what would you have done in Elanorās situation?
My thoughts on Elanorās dilemma?
There are a few things I would advise her on.
The first thing that occurred to me was that the job offer wasnāt finalized yet, not even close. Some random recruiter on LinkedIn telling you about a job is a long way from putting your first salary in the bank. Caution required.
Secondly, she was just scratching the surface in her new career, how far could she take it, say 3 or 6 months down the line? She was already underpriced (I donāt think she realized this as she was still feeling her way), what could she raise her rate to? Maybe her freelance Copywriting earnings could outstrip the job salary.
On this point, you know I advise new Copywriters to keep pushing the envelope and discover their ceiling, I would advise Elanor to do the same.
What about doing the job and freelance copywriting as a side hustle?
This was another possibility, how did she know her commitment without pursuing the job opportunity and nailing down what was involved, maybe she could manage both?
Finally, would she ever be truly happy if she went back to a job, sheād left one to go freelancing for a reason. Would it be a regret sheād carry with her for the rest of her life, a dream sheād given up on?
When I last looked at Elanorās post, there was no firm decision made, but plenty of advice coming in.
What would you do? Comment below.
Thanks for reading to the end
The twist in the tailā¦
This story is 100% true, the name and the picture of Elanor Paterson above are not.
The picture comes from a website called thispersondoesnotexist.com
The website uses AI to generate lifelike pictures of people who donāt actually exist in real life, itās fun and really useful.
Note: to generate more faces on the site, just keep refreshing the page in your browser (right-clickārefresh).
Oh, and the name Elanor Paterson, an anagram of ānot a real personāā¦
Donāt forget to comment below!


