Job searches are humbling. They test your confidence, your patience, and your ability to stay motivated when things don’t move as quickly as you’d like. But they also teach you things about yourself that you might not have learned any other way.
For me, the past few months have been a crash course in rediscovering what really matters: not just in a résumé, but in relationships, self-perception, and how we use technology to help tell our stories. Here are three lessons that stood out.
Reach Out to Your Network (Long Before You Need It)
Your network is a living thing. It requires upkeep, time, and attention, just like a flower garden. You can’t ignore it for years and expect it to bloom the moment you need it.
Start planting early. Stay in touch with people whose paths you’ve crossed - colleagues, mentors, partners, even those you only worked with briefly. Drop a note once in a while. Comment on their posts. Share something that made you think of them. These small gestures are the sunlight and water that keep your network alive.
When I began my search, the people who reached out to help weren’t random. They were the ones I’d stayed connected with over the years - the ones I’d invested in without any agenda. That investment paid off tenfold when I needed advice, introductions, or simply encouragement.
Networking works best when it’s not about networking at all. It’s about relationships, and relationships are built long before you need them.
Know Your Worth
An old friend who runs a large recruiting firm once told me something I’ll never forget. Paraphrased, it was the following:
“Your title doesn’t matter. People can look at what you did and tell what your title should have been.”
That line stuck with me. Too often, we undersell ourselves because our official job titles don’t fully capture what we actually did. I’ve been there.
At CA Technologies, the title of one of my many roles was Director, Solution Strategy. This sounds fine on paper but outside the company, no one really knew what that meant. In practice, I was doing the work of a Field CTO: shaping go-to-market strategies, engaging the C-suite during strategic deals, mentoring Solutions Engineers, and aligning enterprise initiatives across product and sales. So when I began my search, I leaned into the title that reflected my actual scope and, suddenly, doors started opening.
That’s not résumé inflation; it’s accurate framing. It’s understanding your impact and communicating it clearly. People hire based on perceived value, and it’s your job to make sure they see the real value, not some arbitrary job title that requires them to infer what your value is.
Titles come and go, but your contribution speaks louder. Know your worth, and don’t be afraid to label it properly.
Use AI as an Intelligent Assistant
AI can be a fantastic tool in a job search if you use it correctly. I wrote about this in a previous post but it bears repeating: AI is best used as a collaborator, not a crutch.
I used it to evaluate how well my experience matched certain roles, identify potential gaps, and even clarify how to position my strengths. When I was working through a TOGAF certification course, I used it to explain complex concepts in plain English and reinforce my learning. It didn’t replace my judgment - it expanded my perspective.
Used this way, AI becomes a mirror: it reflects your story back to you in ways that help you refine and sharpen it. The output is only as smart as the input, but when used thoughtfully, it’s like having a career coach who never sleeps (and doesn’t mind being interrupted mid-sentence).
The Real Lesson
The biggest thing I learned wasn’t about résumés, titles, or even networking. It was about clarity. A job search forces you to articulate who you are, what you bring to the table, and where you want to go next.
When those things align - when your network knows your story, when your confidence matches your contribution, and when your tools amplify your message - good things happen.
Because in the end, the goal isn’t just to find a company that wants you. It’s to find a company that deserves you.