The Challenges of Job Hunting at Age 63

Yep, I’m job-hunting at age 63. It’s a strange feeling, because I’ve spent most of my life as an entrepreneur, small business owner, and freelancer. The few times I’ve worked for someone else have been either because of a business acquisition or through personal connections. I haven’t submitted an unsolicited resume in over 20 years!

Four years ago, I decided to take a full-time position with Yellowstone Wildlife Sanctuary and let my kids take over our tea shop. Within a year, I was their Executive Director. Now, I’ve decided to move on. At this point in my life, I want to get back to creative work and analysis instead of managing other people.

I’ve only just begun the job search, but I’m already seeing some serious challenges that others my age might want to ponder and prepare for:

Challenge 1: Age

It’s illegal to discriminate based on age. That doesn’t mean it won’t be a problem. If you’re five years out of college, all of your experience is recent. Hiring managers will consider it current and relevant. If you’re 40 years out of college, they are likely to look at most of your experience as no longer relevant.

There’s a stereotype in our society of older people being technophobes, resistant to change of any kind. Since turning 55, I’ve learned two new programming languages, adopted a wide variety of new software tools, taken over a dozen online courses, and started a podcast. I’m constantly learning — more than most people half my age — and constantly changing direction. But that stereotype is hard to break.

Overcoming the challenge

Why not just leave my age off of the resume? I do that, of course, but it’s not hard to infer. Anyone with the most mediocre of Google skills can figure out my age and background. Instead, I focus on accomplishments. Mentioning 29 published books, 7 computer manuals, and over 300 articles will get someone’s attention no matter how long it took me to do it.

Challenge 2: College Degrees

Not finishing my college degree was a no-brainer at the time. It was Silicon Valley in the 1970s, with job offers everywhere I turned. Being skilled with software development and writing made me a valuable commodity, and that only got better as I learned to design microelectronics. Lack of a degree never had the slightest effect on my career.

Until now.

Despite the fact that I had enough industry experience to get a teaching credential, having to fill in “none” or “high school diploma” on a job application form puts me at an immediate disadvantage. A few forms offer “some college” as an option, but not many.

I completed 77 units toward a computer science/data processing degree before dropping out to take a job as an operating systems programmer. Virtually none of what I learned back then would be relevant today. The first functional demonstration of the Internet using TCP/IP happened when I was a sophomore. There was no mention of object-oriented programming, as languages like C++, Java, Python, and Perl didn’t exist yet (I studied FORTRAN, assembly language, Pascal, BASIC, and PL/1). Tim Berners-Lee hadn’t yet dreamed up HTML and the World Wide Web.

Yet, for some reason, I would be much more likely to be hired if I had completed that degree 40 years ago.

Overcoming the challenge

Don’t try to hide the lack of a degree. Instead, work in counterpoints at every opportunity. In my case, I focus on that teaching credential, even though it’s long expired now. You could also focus on any time you spent in college even if you didn’t graduate, or focus on certificates, credentials, and online courses you’ve taken.

Challenge 3: AI Resume Analysis

The biggest challenge in job hunting used to be getting that first interview. Now, the challenge is getting a human being to look at your resume. Most larger companies use artificial intelligence tools called Applicant Tracking Systems (ATS) to pre-screen applications. If you’re rejected at that stage, nobody will ever see your carefully-crafted cover letter that explains your relevant experience.

This compounds the college degree problem for me, because the dropdown menu doesn’t include “no degree, but I got a teaching credential in computer technologies” as an option. Most don’t even have “some college” as an option, leaving me to select “high school diploma,” which is rejected out-of-hand by the AI tools.

Overcoming the challenge

This is a hard one to fight. If the application allows you to upload a cover letter, do so. If the job listing includes the name and email of a hiring manager or recruiter, reach out to them. If you know anyone who works there, see if they’ll put in a word on your behalf.

Challenge 4: A Freelance Background

Much of my resume is filled with freelance work. In a traditional job application format, that doesn’t look like a real job – even though freelance writing was my primary source of income for over 15 years. You can’t just list everyone you’ve ever freelanced for, either. In my case, that would add dozens of “employers” to the resume, making it virtually unreadable.

It’s hard to show freelance work well on a resume when you’re hunting for full-time work. On the other hand, freelance writing is the ultimate meritocracy. A busy magazine editor isn’t going to chase you down on social media to see how old you are or what color you are. All they care about is that you write well and accurately.

Overcoming the challenge

One solution is the old “if you can’t beat ’em, join ’em” approach. I’ve considered going back to the freelance world, but I’ve been out of it long enough that I don’t have the network of contacts that sustained me back in those days. I’m hoping for a full-time job, but we’ll see what happens.

UPDATE 2023: I did move back into the freelance world, but I’m using current contacts from my most recent job instead of going back to freelance technical writing or ghost writing.