DonovanVC,
I have made two major career transitions. Many people (especially women invested in your accumulated previous career status) will say that is one too many. Still, you seem to have the "strike out" yearning. That's all good, I understand completely, very admirable.
Your current customer list is pretty much off-limits, especially if you have a non-compete/confidentiality agreement. But your skills are likely more transferable than you consider. Honestly, your skills are in highly ambiguous (and challenging) fields such as legal consulting/services. Perhaps the specific application of your current employer is very narrow (totally understandable as everyone should find a niche to exploit) but your true skills are very broad (legal expertise in a given field is narrow, but legal capacity in a variety of fields is more "fungible" and a matter of immersion into a niche). If you "got smart" in one legal field, then you are probably smart enough to "get smart" in another. I'm not discounting experience totally, but you should take a broad look at your skills, especially if you are still in your 20s or early 30s.
If you like your field and seek an employer change within your field, then I agree: 1) go where there is a lot of action, 2) make yourself useful, 3) climb the ladder. Maybe it is time for a move to a bigger city in your own field...
But your topic is about making boss transactions from entirely different fields, so it appears you are willing to cast a broader net than staying "in field."
Have you ever attended a franchise expo such as:
http://www.ifeinfo.com/
That experience changed my life in many ways, and I encourage any Red Pill Aware Man to at least consider attending such a conference and owning their own business. Small business ownership is not for everyone, but I encourage you to consider it.
There are two more websites also worth visiting:
bizbuysell.com and
businessbroker.net.
These are the "realtor.com" and "zillow.com" of the small business world. Good places to search by industry or by location.
No matter what you do, you are largely asking "will my leadership ability work at the next place?" It is a fair and serious question. Some time ago, I read the following principles of leadership:
1. Know Yourself and Seek Self Improvement
2. Be Technically and Tactically Proficient
3. Seek Responsibility and Take Responsibility for Your Actions
4. Make Sound and Timely Decisions
5. Set The Example
6. Know Your Soldiers And Look Out For Their Well Being
7. Keep Your Soldiers Informed
8. Develop A Sense of Responsibility in Your Subordinates
9. Insure the Task is Understood, Supervised, and Accomplished.
10. Train Your Soldiers As A Team.
11. Employ Your Unit In Accordance With Its Capabilities
Now these rules were built for military application, but trust me they apply to the civilian world pretty well also. Rule 1 sounds awfully familiar to any regular rooshvforum visitor, and I agree it is so critical.
Donovan if you were to really consider your true skill set, then compare it very openly to available opportunities, maybe you would see more options. I suspect this is what Bannon did. How does a man follow his career path without a few curious moments of introspection that he obviously had along the way, and the realization that his skill-set was pretty broad after all?