First, stop second guessing yourself. (You did it at least three times in your question.) Second, CARPE DIEM! (Seize the day.) You will NEVER have the same free

First, stop second guessing yourself. (You did it at least three times in your question.) Second, CARPE DIEM! (Seize the day.) You will NEVER have the same freedom tomorrow that you have today. (Figuratively speaking.) Time and responsibilities have a way of accumulating over time and now, when your time is your own and the world is at your feet, is when you should be experiencing life even if you're not certain of your direction. It's said that "time is wasted on the young and wisdom is wasted on the old". I realize it's hard to know what the right direction is and making the right choices ultimately means a "leg-up" against the competition. But honestly, the competitive spectrum is WIDE and there's plenty of room for someone to rise to the top no matter how late in the game they make it. So don't worry to much about this. As far as your personal situation, i almost did the Air Force thing and I've gone through their OTS summer programs. I'd argue that their office jobs are NOTHING like the private sector. If you're eager to try out the startup game, there are people hiring like crazy right now and I'm positive you could land any of them (even as an intern). Express your desire. Drop the uncertainty act. Try it out and see. Here's an intern gig in NY that I HIGHLY recommend: http://www.skillshare.com/careers/jobs http://www.skillshare.com/careers/jobs Here's a great intern site for a bunch of startups all over the country (still young and might not have stuff in your immediate area): http://www.internmatch.com/ http://www.internmatch.com/ And in the way of getting that first job, here's a post I wrote for someone who was in a slightly similar situation: http://nobulb.com/2011/05/wanted-an-entry-level-job-that-doesnt-suck/ http://nobulb.com/2011/05/wanted-an-entry-level-job-that-doe...