Seeing Yourself More Clearly

How AI Can Help You Navigate Career Transitions

“Work smarter, not harder.” While this phrase may seem cliché, it holds real wisdom — especially in today’s world, where AI tools like ChatGPT and LinkedIn’s AI solution can help you gain clarity about your skills, experiences, and value to prospective employers.

Job searching can be daunting, especially when it stretches longer than your bank account can comfortably handle. After submitting countless applications with little to no meaningful responses, it’s easy to start questioning your fit for these roles and even your self-worth. Before negative feelings take hold, consider enlisting AI as a thought partner to help you see your value from a fresh perspective.

How AI Helped Me Reassess My Career Path

The past year has been challenging for me, both personally and professionally. At times, I found myself scrolling through job descriptions, wondering whether reentering the traditional workforce was the right move. LinkedIn’s AI helped me tweak my profile, making it more industry-friendly (for example, adding “B2B” to describe my work at TD Ameritrade).

But the real magic happened when I started using ChatGPT.

The Prompt That Changed My Perspective:

“Below is the job description for an open role to which I would like to tailor my resume, which is also below. Please ask me any questions that would be useful before generating a new resume.”

At first, I expected AI’s value to lie in generating a polished resume and cover letter. But I soon realized that the value wasn’t in the final product but in the process.

The Answers Are in the Questions

The AI’s questions prompted me to:

• Recall valuable experiences that weren’t on my resume.
• Evaluate how well the role aligned with my skills and values.
• Notice aspects of the company or position I hadn’t fully considered.

As I worked with ChatGPT — who I fondly call Cathy — I realized that the AI wasn’t just a tool; it was a thought partner. Cathy’s questions helped me see the opportunity and myself in a new light.

I often found myself thinking:

• Oooh, I hadn’t considered the company from that angle.
• Yes! I have experience in A, B, and C — I should highlight that.
• Actually, no. I don’t want to work in an environment that values X, Y, or Z.

Cathy’s questions didn’t just refine my applications; they helped me refine my direction. Ultimately, they led me to realize that my own LLC is the best fit for me right now.

Making AI Work for You

If you approach AI as a collaborator rather than just an automation tool, it can help you:

• Recognize your strengths. AI-generated questions can surface skills and experiences you may have overlooked.
• Evaluate role fit. A job description might seem like a match on paper, but the right questions can reveal whether it aligns with your career goals and values.
• Gain confidence. Seeing your experience framed in new ways can reinforce your value and help you advocate for yourself more effectively.

AI can’t make career decisions for you, but it can help you ask better questions — the kind that leads to real clarity. So, if you’re feeling stuck in your job search, consider making AI your thought partner. You might see yourself and your next opportunity in a whole new way.

Acknowledgments

Thanks to Cathy (Chat GPT) and Guerdy (Grammarly) for helping me with this post. It would have taken me forever without you.