So far I’ve submitted 25 applications. None have gotten past screening.
About a week ago I watched a GitHub live stream hosted by Gwyneth Peña-Siguenza and Cassidy Williams. During the stream I asked in chat if using AI to help with writing cover letters was a good strategy. The response was no, it’s not a good idea.
This confirmed what I had been thinking for a bit now, that using AI to help with writing my cover letters is proving more trouble than it’s worth. While I don’t have a philosophical problem with using AI to help write my cover letters, I found myself spending more time wrestling with my humanizer and voice skills than actually doing productive work on my applications. So I’ve stopped using AI to write my cover letters and form answers, though I’m still using it to personalize my CV to each role, and for helping me with other steps in the process.
Another thing that stood out from the stream: Gwyneth mentioned that around the year 2015 she ended up submitting 200 or 300 job applications before landing a help desk job. So that’s my new goal. I aim to submit 300 job applications before feeling that I’ve adequately done this job search.
That, of course, means that half an application per weekday won’t cut it. I’m in the process of updating my Beeminder goals to move me to four applications daily. Even so, at four applications per weekday, that will take me just under four months to complete.
I won’t be relying on a single goal to require this. I plan to create four new goals, one per application, spaced throughout the day. That way, if I’m having more trouble one day, I won’t end up procrastinating until I only have an hour left to prepare and submit all four applications.
After stopping using AI to write my cover letters, I’ve found a process that seems to be working well for writing my letters efficiently:
- I talk back-and-forth with Claude about the role until I have a good handle on everything I want to say and the relevant experience and gaps I want to include.
- I write the letter in Obsidian, pulling in reusable paragraphs I’ve saved from previous cover letters, modifying them and adding surrounding paragraphs as needed.
- Claude reviews the letter for accuracy and gaps.
- Once complete, I submit the cover letter with my application.
- Claude then extracts any new reusable paragraphs from my submitted cover letter and saves them for future cover letters.
This has helped writing the letters be a lot less overwhelming and faster than any of the approaches I’ve tried previously.
Wish me luck!