How To Job Hunt Like a Boss (With AI)
Image by Hunters Race on Unsplash
I’ve been in the job market for exactly a month now. If anything, I currently feel busier than I did when I was in a full-time job. A month ago I was working full time and doing freelance gigs on the side. Currently I’m doing as much freelance work as I can handle to make ends meet while searching for and applying for as many appropriate jobs as possible. It’s well beyond full time.
That said, this current job hunt isn’t feeling as demoralizing as the last time I was out of work and looking for a new gig. This is partly to do with my bringing what I think is a positive attitude to the hunt. The last time I faced this situation I was catastrophically depressed and the process of pumping out applications felt like the metaphorical stations of the cross. This time around I’m fundamentally healthier mentally. I still get up at the same hour as I did when I was working full time, dress appropriately for work, and just get on with it, whether it’s contract work or pumping out resumes.
The other thing that’s different from the last time I was in this situation is AI. This has been a fundamental game changer that has enabled me to apply for far more jobs than ever before. As of today, I’ve applied for a total of 35 positions, giving me an average of more than a job a day. So far I’ve had two bites—including two written tests and one actual interview—which I think isn’t bad considering that the vast majority of the jobs I’m applying for are remote positions wherein I’m competing against candidates from across the country, and in some cases the entirety of North America.
From a purely quantitative standpoint, AI has changed everything. For one thing, it has dramatically reduced the time it takes me to find positions to apply for. Thanks to my own personal GPT, which I’ve trained with all my preferences regarding job descriptions, required skills, level of seniority, salary, and so on. I never have to remind it of what I’m looking for. I simply ask it what the latest and greatest job opportunities for a person like me are and it finds them for me from across the interwebs. Last time I was doing this I had to spend hours scouring LinkedIn and innumerable job boards for appropriate positions. That’s all history now.
AI has also made the process of preparing applications a lot faster and easier. Back in the day I would end up sending out basically the same resume with minor tweaks to an assortment of prospective employers, with the odd key phrase from the job description wedged in somewhere for good measure. Now I ask my personal GPT to create a customized resume for a particular job description and it does it in seconds.
Of course, the results are invariably far from perfect. For one thing, as we all know by now, ChatGPT loves to make stuff up. Any given resume it spits out will reference statistics that aren’t real (e.g. “increased SEO credibility by 40% for Client X”) and credits me with skills I absolutely don’t have. There’s exaggeration of one’s skills and then there’s flat-out lying, and I’m not going to do that. Also, ChatGPT is notoriously bad at math. When it produces a resume it always seems to get the dates of my job history wrong and represents them in a way that doesn’t make any sense. I mean, I was never a great math students, but come on! You’re a robot for chrissakes!
There are other ways in which ChatGPT gets job applications wrong. For one, it’s obsessed with emojis and I’m still conservative enough to think that emojis don’t belong on a resume or cover letter. If for no other reason, a resume full of cute emojis in the place of bullets is probably a clear sign that ChatGPT wrote it, and that’s not a signal I want to send to a prospective employer. And speaking of cover letters, Chat is really not very good at writing these. The introductory paragraphs are invariably real stinkers, with opening sentences like “In today’s fast-transforming digital landscape, data-driven content marketing is not a bonus—it’s a must.” Nope. Pass.
That all said, I couldn’t be more thankful to have these tools at my disposal. I still take a lot of time and care over my resumes and cover letters, but ChatGPT is absolutely brilliant at pulling key wording from job descriptions and weaving it into resumes and cover letters. Of course, I do take the time to read over the job description to make sure Chat isn’t hallucinating, but it’s usually correct.
With cover letters, I generally do end up rewriting the whole thing, but as I discussed in my “blank page of doom” post, having text on a screen to work with has a way of blasting through paralysis and getting me going. It’s a support structure that I’ve come to rely on to neutralize my natural tendency to procrastinate.
So that’s the current state of my job hunt, in a nutshell. It’s still a slog, but it’s a much more tolerable slog than it used to be thanks to our technology du jour. One poster I saw recently on LinkedIn said he ended up applying for 200 different jobs, getting a total of three offers. If these are the odds I can expect, I’m about half way towards one offer. Back in the day, this would have made my mood plummet. Now that actually seems doable. The competition may be fiercer than ever, as invariably happens when you get more senior and you go remote, but capacity to put out professional and (hopefully) compelling applications has also increased dramatically. As such, I remain cautiously optimistic.
Oh, and if you’re a hiring manager looking for a new content strategist or communications manager or copywriting guru of some kind, please reach out to me here. I’m ready and eager and increasingly AI-savvy. I’m also lots of fun to work with. Try me!
