How easily would you be able to distill the breadth of your experiences to one piece of paper? Single sided. 11pt font. If it's easy for you, then I need your services.
I despise cover letters and resumes like no other task I've had to complete. It does not get easier with gloves on (like gross cleaning tasks). I cannot hire someone else to do it for me (review it, yes; know my life well enough to create content, no). I have no problem talking about myself or tooting my own horn. My problem is doing these things authentically while conforming to arbitrary formatting and language structures.
My understanding is that a resume and cover letter form the first step in determining if an applicant is qualified for a position and how well they will fit that position. But I'll counter that you can have the most capable person in the world fill the position and spend the next however many years hating that person's guts because he or she is a huge jerk. Think about the people you work with. You can train them on the skills they need to complete their job. You cannot de-jerk-ify them. So isn't it more important to find someone to fit with the climate of the office? And how can personality be determined by such structured writing?
This is why I struggle to find jobs. I must first overcome my revulsion for this application structure, then complete said application materials, then hope they find redeeming qualities within them, THEN I get to charm them in person. I would much prefer to just charm people outright and have them offer me a job because they have met me, have seen me perform tasks, and know that I'm not a nitwit.
Just one more reason writing makes sense to me as a career choice. If I'm trying to get hired somewhere, or even just get one piece published, I am judged on my work or my body of work. I don't have to write some silly letter that falls over itself trying to compliment the employer AND show I am a worthy human being, all while using every single loaded buzz word I can remember.
Forget representing myself in the two-dimensional. As a woman, as a writer, as a human being, I am far more complex than that.