Let’s go ahead and say that you are a true hero, and the only thing needed to turn the tide of the fight is you. First, I’m here to tell you that you are wrong. If you’re in it for money, stop reading and find a private military contractor. If you want to fight terrorists, stop dodging the local recruitment center.
My opinion is not forged from my military service, but from nine months of volunteer service in the Iraqi, Syrian, and Ukrainian battlespaces throughout 2014 and 2015. During that time I served on a volunteer basis as a non-contracted and unsponsored advisor, consultant, explosives-hazard mitigator, and trainer against Daesh (IS/IL) and pro-Russian separatist forces. I operated entirely as a freelancer and was under no governmental agreement, corporate sponsorship, association contract, group or unit affiliation, or under any organizational obligation. In fact, SOFREP did not pick me up until I had finished with such things. I am not, nor was I ever, a mercenary, and the few times that people felt sorry enough to give me a few dollars, it was always far short of delaying my imminent 2015 bankruptcy, and was geared toward providing rations outside of standard chow.
Prepare yourself to be flat broke if you’re doing this correctly. You’re going to need to sell off whatever you can—from your first-edition novels to the magnificent love of your life, your BMW 528i. It will all have to go to cover your expenses at home and abroad if you are going to do things legally and morally. Of course there are lots of opportunities to make money abroad, that is if you’re willing to risk never coming home again and/or spending time in a maximum-security prison in a hostile nation.
In late 2014, when I first left for Iraq, I had half a plan and a few contacts, but things got messy from there and quickly went awry. This was largely due to the fact that there are too many involved parties that share an overall goal to defeat Daesh while also maintaining many selfish and conflicting interests. Plan on things to go wrong. For me, things went wrong shortly before my flight. I was lucky enough to find a replacement group before I landed in-country. If that had failed, I would have simply hit the bars in Erbil and snooped around looking for an opportunity. I would not advise my fallback plan to anyone, and I surely would not have brought anyone along with me.