I think it's much the same in any industry. Those that are in it for a long time know the risks and benefits so well that they become desensitised.
Many people work in different lines and so get a new perspective. For example, whilst I worked in telecommunications for 27 years, I was in small companies, local govt, retail, financial, cargo etc. I also worked in different countries and was a freelance consultant so I met numerous clients and situations - which helped me to continue to think about the end user.
Pilots, mostly, have only ever worked in the piloting business and many stay with one company for extended periods of time. Thus they can easily get distanced from the those in 56B.
I now work in a field where customers are usually first time purchasers. A few are second or third but most do not purchase more than three times in their lives. Conversely, many have worked in the business all their lives - so I see some of the 'old hands' getting casual. I was discussing this just yesterday with one of the best in the business that I have met in 22 years.
I'm now off to work with clients who are first time purchasers ...
ps I'm not that old, my two careers overlapped!