I used ChatGPT to find work in retirement — here’s how I did it

At a recent South by Southwest webinar, futurist and Wired magazine founding executive editor Kevin Kelly called generative AI “the universal personal intern.”

By that, he said, “it can do jobs that humans don’t want to do or can’t do.” And it can do them superfast. “ChatGPT is better at synthesis than we are,” Kelly said.

Read: The most common financial regrets retirees have, and how to avoid them

ChatGPT, résumés and cover letters

Already, AI and ChatGPT can quickly and brilliantly improve your résumé and cover letters — if you remember to add your own human touch.

David Fano, CEO of the personal career growth platform Teal, is a huge proponent of using AI to find work.

“I feel like if there is a tool that can help us do something, we should use it,” he told me. “I’m sure someone thought the wheel was a bad idea. Someone thought the typewriter was a bad idea. The printing press was a bad idea. That’s just going to happen.”

But for people looking to work in retirement, Fano said, “any technology that helps you better present yourself and be more efficient — you’d kind of be silly not to use it.”

Read: With house prices this high, boomers may want to become renters

AI helps people get hired

Turns out, plenty of job seekers are. A ResumeBuilder.com survey of over 1,000 current and recent job seekers found 46% reported using ChatGPT to write résumés or cover letters or both. Roughly 70% of those did got a higher response rate from employers; 59% were hired.

A January 2023 National Bureau of Economic Research study by three MIT professors found that job seekers who used “algorithmic writing assistance” experienced an 8% increase in the probability of being hired. The AI tool made smart suggestions to correct errors and clean up the job-hunter’s writing.

Using AI to find the right job

The first way to use ChatGPT (for simplicity’s sake, I’ll use ChatGPT throughout this piece when talking about generative AI; there’s also Bing, Bard, and others) for a job search in unretirement, Fano said, is to figure out the type of job you want and how to position yourself in the job market.

“Go find five job descriptions you’re super excited about. Put them all into ChatGPT and ask, ‘What are the commonalities across these five?’” said Fano.

You can also ask ChatGPT to turn up the largest companies with particular jobs in your state and then check their sites for openings.

Career transition coach John Tarnoff wrote on LinkedIn that a key rule for using ChatGPT when job-hunting: Ask it “Do you understand?” at the end of each query. That will give you a summary and you can then correct the bot if it’s a little off.

Tailoring your resume with bot help

Once you’ve found potential jobs, you can have ChatGPT tailor your résumé accordingly. (By the way, don’t worry if you’ve heard that ChatGPT’s knowledge stops in 2021. That’s true regarding news events, but if you include your work history since then, it knows to use it.)

After signing up for the service, give the bot pertinent information about your job history and the type of job you want (don’t include your phone number or address; doing so will include that information in ChatGPT’s brain for anyone to pick). The more specific you can be, the better the results you’ll receive.

Seconds after giving the AI tool what you want, it will spit out a version of your résumé with requisite keywords your prospective employer’s Applicant Tracking Service will want to see as well as a Professional Summary (if you ask for one).

ChatGPT will also help you brag about yourself, using words and phrases demonstrating your accomplishments. “People are not comfortable doing that and articulating successes and achievements in concise and crisp ways,” said Fano. “Computers are very good at that.”

You could say to ChatGPT: “Draft X résumé achievements from my résumé.”

You could also ask ChatGPT to write a fictitious résumé for a type of job you want and then use the template as a model to fill in with your own work history.

Another idea: Ask ChatGPT to tell you the skills typically required for the type of job you want. Then, you can ensure your résumé notes those skills or you could spend some time getting the skills.

Add the human touch

But you’ll be making a big mistake if you blithely send an employer a résumé ChatGPT made for you.

“ChatGPT is a great tool to get you 50% of the way there,” said Carmen Bryant, vice president of marketing for Wizehire, which helps small businesses find workers. “It can provide a draft, but it’s not going to be able to provide your unique point of view.”

AI is also prone to make mistakes; what techies call “hallucinations.” So, you’ll want to carefully review the résumé you get to ensure it has no errors.

You can also give ChatGPT your résumé plus a job posting that interests you and ask it how well your work history and skills match the job description. With that information, you can amend the résumé accordingly.

You can also use ChatGPT to do similar work to improve your LinkedIn profile, since that’s one way many employers and recruiters review potential hires.

ChatGPT and cover letters

Once you have your ChatGPT-enhanced résumé, you can turn to the bot for help with your cover letters. Here, too, the more specific you are, the better the results you’ll get.

Recruiter Lexie Garcia wrote on Viget.com that she found after playing around with ChatGPT “even an unsophisticated use of ChatGPT is ‘better’ than a lot of the generic cover letters we’ve seen in the past.” It produced cover letters that were clear, appropriately conversational, spelled correctly and with greetings and signoffs, she noted.

Give ChatGPT your résumé and a description of a job you want and ask it to produce an appropriate cover letter. Chances are, it’ll do the job quickly and offer a shorter, better version than the one you’d do on your own.

Teal’s Alli Tunell recommends using prompts to ChatGPT like these: “Write a conversational cover letter for a job application as a [position] at [company] using my résumé below as a reference.” Or: “Draft a persuasive cover letter in 150 words or less highlighting my qualifications and enthusiasm for the [position] at [company] using my résumé achievements below.”

ChatGPT for job research and interviews

ChatGPT can also help you research a potential midsize or large employer and come up with questions to ask in a job interview as well as questions you might be asked.

Fano recommends giving ChatGPT the LinkedIn profile of the person who’ll interview you and asking the bot what you could talk about together. Or give ChatGPT the job description and ask for five interview questions you might be asked.

My experience using ChatGPT

I’ve been using ChatGPT for some unretirement gig work recently and found it to be very helpful in some cases and a complete bust in others.

I was asked to employ ChatGPT to make a teacher’s guide for a financial literacy course for high-school students.

Phyl Terry, founder and CEO of the senior executive community Collaborative Gain, wanted to use some of Warren Buffett’s annual Berkshire Hathaway shareholder letters as the educational tool. He came up with questions based on information in the letters. My job was to give ChatGPT the Buffett letters and specific questions about terms and concepts in them and have AI give me the answers that I’d put into the teacher’s guide for the instructors.

In most cases, ChatGPT was extremely fast, writing full paragraph answers that were spot on. In some cases, however, it was exactly wrong. I then had to do my own research to provide the accurate answers.

So, to complete this assignment, I needed to spend a fair amount of time ensuring accuracy and fixing ChatGPT’s errors.

All in all, though, I’d give ChatGPT a B+.

A tool to get a book going

Debbie Weil, the Stonington, Maine, author, marketing strategist and host of the [B]OLDER podcast and Substack newsletter about reinventing life and work and making the most of growing older, has been thinking about using ChatGPT to help her craft a [B]OLDER book.

“After publishing 100 [podcast] episodes, I asked ChatGPT how I might organize such a book,” she told me. “The answer, within seconds, was coherent, detailed, and empowering! Now I have an outline to start from. I can add my own spin.”

I’m not surprised.

In fact, I’ll end this column with Fano’s generative AI advice for unretirees: “Play with it. Use the technology. Don’t fear it. Don’t dismiss it.”