I am a combination of the "hard work" and "still climbing the ladder" categories.
I don't believe it when people say thing like, "Nobody ever gave me nothing, I had to work for everything I've got." People usually get a lot of help from people in their lives, and I was fortunate enough to have some good teachers and coaches and a mother who loves me.
I am a teen program director and finally achieved my dream of working with kids in the outdoors full-time. Lots of camp counselors go for it, but sustaining jobs in outdoor education are quite competitive. It's typical for a job earning between $20-30,000 to have dozens or hundreds of applicants, and a high percentage of those will have a college degree and two years of experience.
The numbers the other way, from an applicant's perspective, are tough. I had been looking for three years when I got this job. Let's see, my numbers from that time period would be:
about 200 resumes sent out----> about ten phone interviews ----> three in-person interviews -----> one job offer!
Peace and good luck!