Hi, I’m Jason

Software engineer, late starter, and someone with a pile of half-finished projects. I write about building, learning, and what I should have learned sooner.

Screen Test

When is a screen a test? Every time, if your interviewer is good at their job. I was reminded of this recently, when I had a first interview with a company I hadn’t spoken with before. Going into this first round, I did the exact thing you should never do when facing the unknown. I made assumptions about the interview based on prior interviews that I had been through. The first screen is never terribly technical, right? ...

July 7, 2026 · 2 min · Jason Chestnut

How Your Resume Lies While Telling the Truth

The most dangerous thing that can happen with your resume when working with an LLM to optimize for job applications isn’t an outright lie. It’s a completely believable exaggeration. Led the decomposition of monolithic Java applications into modular Spring Boot services, defining service boundaries and communication patterns to support independent feature development. Sounds good, right? It does, except what really happened was more like Part of a six-person consulting team decomposing a legacy monolith for a large financial services client. I worked on service boundary decisions and some of the Spring Boot implementation. One of several engineers on the project. That bullet made it into exactly one application before I caught it. One. And I could have missed it even then. ...

July 4, 2026 · 3 min · Jason Chestnut

Stop Lying to Yourself (and Others)

The lying resumes had to stop. After enough customizations for enough job descriptions, my resume had started to look like a copy of a copy of a copy: roughly the right overall shape, but not quite recognizable as the same document. As I’ve been seeking a new job opportunity this time around, I’ve been trying to be selective about where I apply, but also to tailor the resume I submit to highlight how I fit the specifics of each job description. To avoid pulling my hair out, I have also started to rely on an LLM to help. The output typically meets my standards, but one major issue that I’ve started to notice is that my repeated modifications had started to introduce a lot of drift from ground truth and had lost the plot. For example, one position working with a large international bank customer had somewhere picked up the location of Toronto, Ontario. I’ve been to Toronto exactly once, and I never left the airport. ...

June 30, 2026 · 2 min · Jason Chestnut

Lets Go, or A Life-Long Love of Language

“Let’s Go!” — Or, a Life-Long Love of Language I have a collector’s mentality. If it comes in different colors, shapes, or styles, my natural inclination is to own one of each. In a lot of ways, it is about aesthetic beauty. I’ve collected Magic: the Gathering cards with their beautiful art, old Disston handsaws with their stunning etches and hand carved apple handles, and a lot of other things of beauty in my life. The one collection that seems to be consistent, though, is programming languages. It started early on, in my freshman year of college, and still affects my day-to-day relationship with software development. It might be hard to see how that relates to the other stuff, but to me the patterns and shapes of the written code carry their own unique loveliness that is kind of unique in the world. ...

June 19, 2026 · 4 min · Jason Chestnut

Is It Too Late for This?

There’s something embarrassing that I need to admit. I don’t have a portfolio. It’s not that I have just a sparse one, nor an outdated one. I mean a proper, intentional, here’s what I can do portfolio. I’ve worked to convince myself that I either didn’t need one, or didn’t have the right projects to share. Maybe I didn’t have time to really devote to the task. Ultimately, though, the real reason was that starting felt like walking into a room full of people who had been there for years and announcing my presence. Kind of terrifying, really. Maybe you know that feeling, too. ...

May 28, 2026 · 5 min · Jason Chestnut