My work history:
1. Part-time package handler at Fedex Express. Not hard to get into, especially back in 2004.
2. A couple years later, my brother's best friend knew a manager at a new Fedex Trade Networks office that was opening up nearby. Lots of hiring. Since I was already a Fedex employee, making the move was easy.
3. After 7 years at Fedex Trade Networks, a co-worker that I was good friends with was recruited through Monster.com by another logistics/brokerage office just down the street. It's a smaller company that has referral incentives in place, and takes those referrals pretty seriously. So following him over there was pretty easy.
My experience is that social connections are the only guarantee, and beyond that it's mostly a matter of luck. For any desirable position, it takes a world-class work history and reputation to get around that. You can have a demonstrably good skill set and work history, but it doesn't matter until either someone on the inside helps you be noticed or a mid-level position needs filled
right now, meaning they interview the first few candidates with decent credentials they're able to hunt down on their own instead of putting out a hiring call.
It seems to me like the vast majority of people "fall in" to their line of work by pure circumstance, much like I did, and never manage to escape. Trying to break out sucks, and I honestly don't know anyone who's done it. The only people I know who made it into a career of their deliberate choosing did so by steadfastly refusing to put themselves in permanent full-time work positions, staying in school, staying single/uncommitted, and living on student loans until they got the job they wanted.
Getting an interview also seems to be the hardest part.
Resume tips:
-In my case, for jobs #2 and #3, I literally just asked my friends if I could have copies of the resume that got them hired, and adapted those to myself.
-I always listed everything I had any knowledge of that might be relevant to the job, even if my knowledge of a subject wasn't too detailed, and tried to strike a balance between generalizations and details.
-I quantified myself by comparison to co-workers (without mentioning names, of course) and the impact I had on the workplace. For example, both resumes for jobs #2 & 3 mentioned that when I had a day off at Express, three people had to be brought in to take my place (which was true). For job #3, I noted that I summarized a stupid 50+ page training manual about how to process
Lacey Act documentation down to 5 sentences, and the entire office of around 120 employees used that as reference.
Also, I still think you should look into customs brokerage. It's not satisfying or glamorous work by any means, but it would be steady work that I think you would be good at. It's legal in nature and all about knowing a ton of detailed rules and being organized. And if you get a broker's license, which I don't think you'd find difficult, you're basically guaranteed a job. They're highly valued.