I've wondered similar things. Well, and sometimes don't have to wonder, because a lot of people hiring have all the awareness, social graces, and HR-savvy... o

I've wondered similar things. Well, and sometimes don't have to wonder, because a lot of people hiring have all the awareness, social graces, and HR-savvy... of dirt... and will pretty much tell you that they only want early-20s engineers who will look busy for long hours and are unmarried and in no danger of having children soon. :) You said you don't want management track. Do you want to just be only a rank&file IC software developer? What about technical lead of a project team? Do you have interest and experience in being a real Principal Engineer (potentially lots of cross-company technical responsibility, including direct with execs)? If you just want to do "Sr. Frontend" or "Sr. Backend", I hate to say this, but, if your last several years of resume has enough of the keywords that people are looking for right now... maybe that's the experience that goes on your 1-page resume. The abbreviated version could be enough to get your resume past some shadowy unseen influence that is mysteriously filtering what resumes a great hiring manager sees. Nothing says you need to list every job you ever had, and you can always have a 2-page version you show the potentially great hiring manager. (Realistically, there are better individuals and teams than there are companies, so don't rule out a job because the company has ickier elements. Go for the manager and team first, and they have to see you.) (My own situation is different than yours, because I'm targeting the role of startup technical co-founder, who defines and builds much of the MVP, and then grows into building and leading an engineering team. And advertising a big pile of experience is not only relevant to wise founders, but a very useful way for me to filter-out founders who don't value experience.) (But when I look at an IC role at an established company, I still occasionally consider trimming the 2-page resume down to 1-page, and eliding some very relevant earlier experience that I was fortunate to have. Because I know I look a lot older on paper than I am in person, and I'm well aware of not-unusual biases in techbroland.)