I would agree with d2viant; the most threatening element of a resume is the conception of longevity we inherited from the 20th century social compact of loyalty

I would agree with d2viant; the most threatening element of a resume is the conception of longevity we inherited from the 20th century social compact of loyalty between eager beavers and large corporations. My work history is peppered mostly with companies of less than 20 people, and a good chunk of it at companies under 10. However, the job or two I have had -- and the interactions I've had with comparable consulting clients -- in places structurally describable as "enterprise" left me with an enormous appreciation of how differently a lot of the labour force there operates. Most of the people I worked with were strict 9-to-5ers of average intelligence who, over time, became highly knowledgeable, deeply entrenched maintenance experts in various legacy systems the company had, which in many cases dated back to the late 1980s; ROI is ROI. They were quite valuable to those companies, operationally. However, they had been there 9, 10, 15, 20 years; they had virtually no transferrable skill sets whatsoever. When that technology does (did) go, so will their jobs, and they will (do) have an extremely difficult time finding another job in a competitive technology market at any place that does not specifically use those systems. Even the folks who played more generally applicable roles like accounts payable analysis, audits, marketing, etc. often became idiosyncratic domain specialists in that very company's very particular business process and very particular product and customer domain in ways that seemed to call into doubt their ability to shift into an analogous role in another place in time and space. The zeitgeist of 1950-1990 at General Electric or Ford Motor Co. has passed; it's not coming back, I fear. If there's any advice I can give to people today so that they don't end up in this situation when they're 50, it's that you have to embrace this "up or out" approach we talk about so much here. Unless you're willingly headed toward management and significant increases in compensation, preferably short-term and relatively liquid, you need to get out after a few years. When I say management, I really do mean management; one of the pathologies I have seen a lot is to give people of the above specimen doing the same kind of grunt work year-on-year managerial-sounding titles to justify further salary increases, but whose jobs still consist of procedures and processes that suffer from the above-mentioned liabilities. But anyway, the company will not take care of you. Company does not care. Probably will not be around forever anyway, at least not in the present form that has any relevance to you whatsoever.