Resumes Don't Have to Be Hard!

Published: March 31, 2026

The Vicious Cycle Link to heading

I don’t job-hop. If allowed, I stay at an organization until either something happens that forces me out (thankfully, this has never happened), or a better opportunity comes along (more money, better balance, etc). I enjoy working and building things and the more time I spend at an organization the more I can build, the bigger those things can be, and the greater impact I can have.

Still, it is a good idea to have an up-to-date resume. And yet, for years I struggled to do this. The vicious cycle went something like this:

  1. Happily work
  2. Have desire to leave, get promoted, or change job
  3. Resume required!
  4. Dig through Documents/NAS/Backups/Cloud Drives…
  5. Realize that the .docx I made years ago has been lost to time…
  6. Be grumpy
  7. Make another Gill_Resume(20XX).docx
  8. Hate making it…
  9. Realize that Microsoft Word is bad, or that I am bad at using it…
  10. Generate something worth submitting
  11. Get the new job/promotion
  12. Promise that I will keep the resume up-to-date from now on.
    • This is a lie… I will not do this…
  13. GOTO 1

The Rant Link to heading

Every time I make a resume I have the same feelings. They are a combination of desires to best articulate my expertise which are in direct competition with ‘resume standards and practices’. You know the ones… Only one page, front and back. Margins must be blah-blah-blah… Use the correct fonts! Nothing too flashy! It’s paralyzing.

People that are into resumes are really into resumes. They have opinions. They treat resumes like an art-form. And I get it, I suppose. This single piece of paper is there to be the first introduction of you to a potential employer. It should glow with professionalism! It should scream to them that “I am the employee you want!” Which is why some of the standards surrounding resumes have always bothered me. Once you have significant professional experience, relevant personal hobbies and projects, and a set of skills that you are proud of, it is very likely that your resume will be “too long.” Perhaps it is difficult to summarize the many important and appropriate projects that would just make the potential employer’s head explode with how awesome you are!!!

And, the other elephant in the room… I write this in 2026. Hiring systems leverage integrations from a ton of online resources (Indeed, Monster, ZipRecruiter, LinkedIn, etc), meaning that in many cases those seeking to be hired aren’t really producing a traditional resume to the potential employer. Their experience, activities, projects, and skills, are being matched and submitted for hire automatically. I have seen organizations still require a traditional resume as a point of process, but it is no longer the initial point of contact for hiring. The company recruiter already knows that a candidate checks the required boxes, because the integrated systems say they do. The recruiter no longer has a desk with a stack of paper resumes where they are summarily throwing away the ones that are ’too-long’ and ‘poorly formatted’. They aren’t basking in the radiance of that perfect resume (tear in eye, chef’s kiss!). They are looking at a set of tables in whatever Human Resource system manages their organization’s hiring process. They may even be looking at it from an iPhone…

Still, it is a good idea to have an up-to-date resume. It is a record of your career, your accomplishments, your progress! It is something that you should be proud of! And, it doesn’t have to be that hard!

The Solution! Link to heading

I attended the PowerShell & DevOps Global Summit in 2025. During the ’lightning demo’ portion Gilbert Sanchez gave a short presentation about Resume-as-Code. His demo consisted of a quick walkthrough of JSON Resume. Wow!

I had tried using something similar in the past. Reactive Resume was a cool project that I spent more time on the self-hosting side than the actual resume-building side. It included a ton of features, but at the time (2023? Maybe 2024…) I didn’t have the capacity to rebuild my entire resume.

I recently changed job roles in my organization. I thought it would be nice to update my resume, but the only version I could find was at least three years old and in PDF format. Not terribly out of date, but not easily editable. It is 2026 and in walks ChatGPT… I revisited JSON Resume, had ChatGPT take the 2023 resume and convert it into the appropriate format, uploaded it to Github, and in a staggeringly short amount of time… I had a resume! One that I could update and track in source control. One that can easily be transformed using themes. One that I can instantly share with anyone interested about me.

Truly, I believe it doesn’t get easier than this. If you are struggling like I was, or looking for a new job, or just want a cool project for an afternoon, I suggest you check out Gilbert’s blog, and JSON Resume. I did, it worked, and I can finally break that vicious cycle. Until next time!