You don't have to have a multi-million dollar exit to go through this. You just have to find yourself in a position where you had some amazing responsibility and direction and now you don't in a way that mere mortals cannot relate. There are numerous different ways to get there.

My story:

For just about ever I have been a developer in the civilian world and an Army reservist. Normally the Army reserves thing is just a part time weekend gig doing some really boring administrative work, but sometimes its more.

The first time I was in management I was 24 years old. I hadn't finished my bachelor's degree yet. I was working as the tech lead of network operations in a group called TNOSC. This network, though, covered all of US and coalition forces in Kuwait, Iraq, and Afghanistan except for airport control systems.

This was in 2004 during the post-invasion surge into Iraq. I am not sure how many dedicated users I had (maybe 100,000) but there around 300,000 people who were impacted by my network between coalition military forces and supporting civilians. For perspective 300,000 is bigger than Google, Facebook, Microsoft, and Apple combined. In that management position I published the organization's taskorg (a diagram of who owns who plus the structure of our clients). We had two dedicated brigades to manage and my higher authority was CENTCOM with a dotted line to DISA. My clients were two 3-stars and a 4-star.

Running that organization was somewhat like running a start-up in reverse. We already had business and dedicate clients to support, but just jumping you are actually figure out the necessary relationships and how to do the technical aspects of your job. Life doesn't wait for you to catch up. You just have to figure everything out immediately.

In the real world I am software developer. I am not in management. I don't even bring up the prior military story. People simply cannot relate. They know the corporate world they are isolated into. In the civilian world you don't get magically dropped into that kind of position out of the blue.

Furthermore, people outside the military are more fragile. In the civilian world one of the most important interpersonal qualities is kindness while in the military kindness isn't valued. In the military kindness is like hard work. In most jobs nobody is rewarded for hard work. They are reward for what they accomplish. Hard work is silently implied. In the military what's important is honesty, respect (above and below), and bluntness.

I find in the corporate world I am constantly tempering my words and using my "inside voice" so that I don't come off as offensive. It is so easy to come off as an arrogant dick. People who have known me for a while or been through similar environments get it, but for everybody else its too easy to look like an asshole.

This is even more true in that I work as a web (JavaScript) developer. The most frequent kind of developer in the web are people who don't want to be there, have absolutely no regard for the technologies, and wish they were doing something else. The other extreme are immature childish developers who work in the web because it has a lower barrier to entry in the contributor roles require a large dose of abstractions and dependencies for every aspect of their job. Both of these groups are different shades of imposters who constantly live in fear that they will be discovered. Pro tip - Everybody knows who the imposters are. I sure as hell cannot relate my military experiences to these groups who hanging to their one and only career by their nails.