Thirty years in, I still get paid to figure out why the thing is broken.

I’m Dan. I have been building for the web for 30 years, across design, architecture, databases, deployment, and every awkward seam in between. These days I run Hello World, a Portland consultancy I founded in 2015.

The through-line of my career is not a language or a framework. It is a stubborn belief that most technology problems are decision problems wearing a technical costume. Teams rarely fail because they picked the wrong database. They fail because nobody had the standing, or the nerve, to say out loud what the tradeoff was, and by the time the cost shows up the decision is three quarters old and nobody remembers making it.

A lot of my work now is AI-shaped, and I try to be honest about what that means. AI is not replacing software engineering, it is changing what software engineering looks like. That is a harder claim to act on, because it means rethinking review, testing, security, and what a junior engineer is even for. Buying a tool and declaring victory is not the same as doing that work, and the gap between the two is where most of the disappointment of the last few years has come from.

What I actually care about

People who are trying to get in. I started Mentorship Saturdays in 2014 because the path into this industry is mostly undocumented and quietly gated. The advice that circulates is either abstract or survivorship dressed up as strategy, and the actual gates are things nobody writes down: which job requirements are real, who is deciding in an interview loop, whether the thing you are embarrassed about is disqualifying or completely normal. None of that is hard to explain. Almost nobody bothers.

Software that works for everyone. Accessibility and digital equity are not a compliance checkbox at the end of a project, they are a design constraint at the start. Treated that way they make the product better for people who never noticed they were accommodated, which is the whole point.

Longevity over novelty. The systems I am proudest of are the boring ones still running years later, maintained by people who never met me and do not need to. That is a harder thing to demo than a rewrite and a much better thing to have built.

Before the keyboard

I coached basketball and taught sports for the better part of a decade. It is the least technical thing on my resume and the most useful. You cannot fake your way through a season: either the people around you got better or they did not, and either way it shows up on a scoreboard every week. Running an engineering team is the same job with worse cardio and a longer feedback loop, which is mostly what makes it harder.