Could hiring a cover letter writer be worth it?

January 20, 2023 7:44 PM

Writing cover letters has been very difficult for me lately. Is it ever worth hiring a cover letter writer? Have you done it? Did it work out for you? Did it not work out for you?

I know they're not easy for most people, but I find writing cover letters to be mentally excruciating. It wasn't great before 2022 happened, but I was never terrible and during my last job search I had a really good ratio of interviews to applications. I can write one and write a good one.

However, I have a huge mental block when writing cover letters. Especially since that mess with my previous job happened (which I'm working on!!), all my anxiety rises to the surface and I'm filled with dread and low-level anxiety while writing it. As I write these letters I just spend the entire time thinking that a) I'm simply not good enough for the position and this is a waste of time or b) even if I am *in theory* "good enough" with my skills, I'm just horrible at translating that in a cover letter. I sound like a sad robot in my most recent ones, I think. It's just so hard for me! I don't have that confidence that a good job searcher is supposed to have. Also, advice from places like AskAManager, with regards to cover letters, has never rung true for me. I read advice about writing resumes and I just think "ok maybe for other people, but that won't work for me because I'm a giant loser!!"

Today, I wrote a draft of a cover letter and sent it off to a few people to review, and even that act fills me with dread. I'm pretty embarrassed imagining what their feedback might be.

It's a pretty huge barrier I have when applying for jobs. Because of this, I'm wondering if it might not be a bad idea to hire a cover letter writer and test my luck. Even just to see a different WAY of writing one and incorporating my experiences into something different.

Have you done this yourself with success? Was it worth it? Any tips or recommendations for a good cover letter writer?

posted by VirginiaPlain to Work & Money (14 answers total)

I got a lot out of The Job Closer by Steve Dalton. He offers a very comprehensible and dare I say easy but effective cover letter formula. A cover letter writer could be worthwhile, but you really need a system - and a book is probably cheaper.
posted by randomquestion at 7:50 PM on January 20, 2023

Hello! This is me. Writing cover letters makes me feel physically ill, and I have read every Ask A Manager cover-letter post ever, as well as hundreds of both legitimate and content-farm pieces on the internet and several books. None of them have helped. (Though I haven’t come across The Job Closer, randomquestion, so thank you for the recommendation!)

Infuriatingly, almost all cover-letter advice I’ve seen is for entry-level workers. I know this *should* register with my brain as, Cool! We don’t need to over-invest in this, because it’s probably not a make-or-break thing for senior-level personnel! Instead, my brain shrieks, WE MUST WRITE THE PERFECT 400-WORD EPIGRAMMATIC SUMMARY OF OUR ONCE AND FUTURE EXPERTISE OR NEVER HAVE A JOB AGAINNNNNNNN

If you want to work with a human who is incredibly positive and straightforward, I worked with someone a few years ago that I really recommend - her name is Mac, she’s a foster-cat mama and former headhunter who now does career-building support work full time, and working with her was effectively like a short course in work therapy. It hasn’t cured my anxiety, but the work we did together has continued to help me a couple of years down the line.

It looks like her cover-letter-session-plus-writing package is $150. If you have any questions or want to reach out, send me a MeMail. The interpersonal support was far more important than any tips I’ve read or samples I’ve pored over.
posted by rrrrrrrrrt at 8:14 PM on January 20, 2023 [7 favorites]

I wonder if this might actually be a case where GPT-3 with its ability to write conventionally and confidently might be useful?
posted by Superilla at 9:12 PM on January 20, 2023 [8 favorites]

I hired a cover letter writer, a MeFite in fact, and had great success. Unfortunately, it appears that she's out of that business.
posted by mpark at 10:37 PM on January 20, 2023

I also hate them. I can say that the second (and last) job I ever got, I was told after hiring that one person really liked my cover letter because it explained why I found the job interesting. But none of them have done any good since, so who the fuck knows. It might have helped to get me my last interview, but then again, didn't get the job.

Frankly, they're easier to write if I actually have any experience and/or interest in the job. The ones I really don't have any justified reason to hire me for them, or I am pretty much only applying because they look like a non-service job and nothing else about them appeals to me at all, well, those letters are pretty generic and vaguely suck. I have generic plug-and-play formatted letters for those, which is probably not great, but I'm not sold on the job and it's a "well, it's something to try" position.

I can't recommend you someone to do it for you, but I can get why you're having a worse time of writing one than usual, if that helps any.
posted by jenfullmoon at 10:51 PM on January 20, 2023

Shoot me a memail if you like, I used to train in this* professionally and have been considering freelancing. Demented as I am, I love a) writing cover letters and b) unlocking the skill of doing it well even though you hate it.

*both the practicalities and mindset of job-seeking
posted by Iteki at 11:51 PM on January 20, 2023 [2 favorites]

Would it help to know that, depending on the field, much of your competition sucks at cover letters?

My anecdotal experiences from serving on some search committees in recent years:

1. If our postings say the cover letter is “optional,” many applicants do not bother. In certain roles this has little bearing on whether they are selected for interview; in roles where strong written communication skills are essential, it’s much more important.

2. Among people who do provide a cover letter, the majority provide a shitty one. It may be shitty in more than one of the following ways:
- Plagiarized, in whole or in part, from one source or several (not only unethical, but a sign of poor judgment generally)
- Generic (full of glittering generalities about the candidate, but no indication that they understand/want this particular role)
- Written with extremely poor mechanics — spelling and punctuation errors, run-on sentences, sentence fragments, and verb tenses are all over the place
- Badly formatted (fonts/line spacing change at random, or no paragraph breaks at all; gimmicky color schemes)

3. Then there are the rare birds who actually write their own cover letter, and who are capable of writing worth a damn. These cover letters are a sight for sore eyes.

I could see the value in collaborating with a professional to develop a cover letter that sounds like you — someone to help you break through the writer’s block. I know you say it was jarring to elicit feedback on your drafts, but I honestly think that was a great idea, too. If you can be open to the feedback, it might spark the inspiration you need.

I’d be wary about hiring someone to ghostwrite it outright, though. Hiring managers want to know your voice.

I’ve read your posts around here. You can write worth a damn! That’s fairly common on MeFi, but it is relatively rare back on Earth. You are on the high-skill/high self-monitor end of the old Dunning-Kruger bell curve.

I wish you could see some of the stinkers I’ve seen from the opposite end. I really think you’d feel emboldened.
posted by armeowda at 12:43 AM on January 21, 2023 [13 favorites]

Seconding the recommendation to try ChatGPT. I've used it for all sorts of purposes, like writing email messages, reports, and even my annual self-evaluation at work. Granted, you have to be careful, because sometimes it writes stupid things, so you have to edit carefully.
posted by alex1965 at 6:02 AM on January 21, 2023

Um...article on using ChatGPG (Washington Post) starts out like this:
Steph Swanson’s latest cover letter begins like this: “I am writing to beg for the opportunity to apply for the position of professional dog food consumer in the abandoned parking garage.”
The rest of the letter — which you can read here if you’ve got a strong stomach — only gets darker as the applicant expounds on her desire to stuff herself with pet food in a secluded parking complex.
posted by jenfullmoon at 9:58 AM on January 21, 2023

I worked with someone experienced as a hiring manager in my field as a coach or consultant who did a whole job application package review, including resume, with a before and after discussion. It was about $400 in total. It resulted in a huge change to my resume and probably substantially increased response rates. She had a totally different perspective on what my strengths were as a candidate. As a less than confident person, this was invaluable as I have an unreasonably low evaluation of those strengths and was under emphasizing them. The resume is often more important, and there's a lot of difference you can make in how you present it. If you can find someone with genuine knowledge in your field, that is best but any third party will see you differently than you see yourself. It also boosted my confidence as an applicant. I would strongly recommend it.
posted by lookoutbelow at 10:55 AM on January 21, 2023 [1 favorite]

Response by poster: Thanks for the advice so far. (I have no idea what ChatGPT is, so that's not an option.)

I think what really messes me up during the job search/cover letters/interviews is that everything feels like it's going to turn into a "GOTCHA!" moment. It feels more like an exam than any formal exam I've ever taken, so constantly feeling like I'm about to get "caught" for one mis-step is torturous.
posted by VirginiaPlain at 4:33 PM on January 21, 2023

Not sure what your field is, but in civil service jobs cover letters are basically not a thing. So that’s one way to avoid them!
posted by exceptinsects at 5:33 PM on January 21, 2023

Nthing Chatgpt, and praying that once we reach a critical mass of AI writing these egregiously pointless cover letters, job applications will stop requiring them.

Chatgpt is very easy to use, and can get the ball rolling creatively, so you’re never starting from scratch with your writing. I personally love writing, but used it a few times last month to get me out of mental blocks.

It’s very much worth the 20 minutes of googling and signing up for an account and writing a decent prompt.
posted by asimplemouse at 2:37 AM on January 22, 2023

Ask A Manager on having ChatGPT writing your cover letter.
posted by jenfullmoon at 9:44 AM on February 2, 2023 [1 favorite]