Jeff Doolittle - From Web Dev To Software Architect

Jeff Doolittle is a software architect, transformational leader, and se-radio.net host who’s on a mission to make good software professionals great.Jeff joined me on Ditching Hourly to talk about his journey from a web dev working for free pizza to an in-demand software architect.Along the way, we talked about the importance of strategy, systems thinking as applied to software, and finding a balance between “wonk” and “geek” in order to deliver real business value.Related LinksJeff's websiteJeff's LinkedInJeff's TwitterJeff's GithubExploring Requirements: Quality Before DesignOn the Criteria To Be Used in Decomposing Systems into ModulesiDesign.netLean Software Systems Engineering for DevelopersThinking in Systems: A Primer ----Do you know you need to niche down, but keep hesitating because you're afraid of picking the wrong niche, cutting off good opportunities, or boxing yourself in?You DON'T need more convincing that vague positioning is a problem.You DO need a way to make positioning feel less risky so you can finally choose a direction, test it in the market, and adjust without blowing up your business.On Tuesday, September 8th, 2026, at noon Eastern Time, I'm running a live workshop called Positioning For Soloists Having A Hard Time Niching Down.That's what we'll tackle in this workshop.It's the second session of my Fall 2026 Soloist Growth Workshop series for expertise-based business owners just like you.Live attendance is limited to 20, so don't wait.Learn more at: https://jonathanstark.com/sgsEnroll in Positioning For Soloists now »Hope to see you live in Zoom on Tuesday.