Ok folks, here we go. I graduated in 2005 with a History BA. I joined the US Military, spent some time there, and ever since have been a coffee importer/consultant. I'm debating changing paths to something in history but, in all honesty, have no idea where to turn to start research and groundwork. I know what interests me, but wanted to ask what resources are available for a job search in the field, what advice you can impart based on your own career (and entry into it), and if an advanced degree is worth it in your opinion (it depends on the work I would do of course, but I recall someone telling me go PhD or go home). In coffee, for example, there are specialized publications, job boards specifically for coffee, education for career paths, etc and I assume the same exists in history but do not know where/what is reputable.
Would any of you fine folks mind giving me some general information and guidance on the aforementioned points so I can do my due diligence and begin to research a route to take? I understand my request is broad, but any guidance you could give would help me narrow down my research and make the transition successfully.
If you're going down the route of being a university professor, it is PhD or nothing. And if you're going for an advanced degree in history, you have to seriously weigh if it is worth it unless it comes with a generous or complete scholarship.
The job market for academics was terrible ten years ago, it is worse now, it is likely going to be worse by the time you graduate. Through hard work, connections, and pure luck, you may be one of the happy few who become tenured faculty. My advice would be to look at the salary and job issues that high school history teachers have and weigh if that's something that you'd be comfortable accepting if you're not lucky enough to snag a professorship. Also weigh that an MA will take you 2 years and a PhD between 4-6. Some even take 8 years to finish their doctorate. During that period you're living on minimal funds and very economically vulnerable. Prospects afterwards don't necessarily outweigh that sacrifice. Your age and responsibilities when you start your studies are something very serious to take into account.
If you have a niche interested in coffee and the private sector allows you to work in something related to that, especially if you have years of experience and connections already, that might be the better bet. I study political history, so my best bets are professorship (unlikely but hey, who knows), think-tank (I'll shoot for the moon), foreign service (unlikely given my personal family connections, but again, you lose nothing by trying), and teaching history at a high school. Maybe something private sector related to Cuba and tourism, but those are basically my options if I do something at least vaguely related to my degree. For me, those decisions all make sense because I'm unmarried and have no kids, and have a passion for history that means I'm willing to take lower pay and quality of life over my lifetime in order to have meaningful work.
Not sure if you play video-games, but here is an analogy. All of these options and all the best effort in the world can merely give you higher percentages of success, but none are guaranteed to give you a good result. Like rolling a D20 with different stats. You need to weigh, long term, if you're willing to accept the most likely (though not the most favorable) results of getting an advanced degree. And the hardest part is, it isn't like you have one career path which is objectively superior to the others. They're all subjectively superior one to the other depending on you. This is as much a test of your ability to decide based on what is going on in the outside world as it is a test of how well you know yourself and what has the best chance of making you happy.
Edit:
Please also put your historian´s cap on when talking to people. Sources have different opinions based on different experiences. A tenured professor may know things are bleak but have a more optimistic opinion, especially if they graduated years and years ago. Other grads will be extremely bitter because they set themselves up for professorship or nothing. I´m a 20 something with an undergraduate degree who will soon head to grad school and who has at least had the privilege of having personal and family contacts in the field which serve as a foot in the door. Critically analyze who is saying what and the motives behind their position/thinking.
Edit 2:
To summarize my point, know thyself. That´s the best guiding light you can have.