Ask HN: Is it possible to get pigeonholed to certain company sizes/cultures?
A master&#x27;s degree will not materially improve your employment prospects but will cost a lot of money and years of opportunity cost.<p>You should devote approximately one week to reading about how to interview better and practicing and then get as many interviews as you can at companies which are large enough to offer a competitive benefits suite. If I were in your situation I&#x27;d optimize for brand-name ones first, since the last name on your resume dominates people&#x27;s impression of it. (&quot;Worked for ten years at university IT departments and small software companies then Yelp&quot; rounds to &quot;ex-Yelp employee&quot; according to basically every recruiter I&#x27;ve ever spoken to, and there are a lot of companies which round to Yelp.)<p>Even if one thought that one was below the supposed bar for large companies, they&#x27;re sufficiently imprecise regarding interviewing that you have at least a 20% chance of an offer given ability to get onto a phone screen and pass the local version of FizzBuzz. Make it your mission to get failed out of their interview loop twenty times; it&#x27;s virtually impossible.<p>P.S. One does not have to change one&#x27;s personality to <i>present</i> differently for twenty minutes on a phone call if one believes that one&#x27;s perceived personality is causing the phone rejections.