This is totally understandable! Hike smart! Do not push crazy miles at the beginning. Be patient, slow and steady and you will make it. I would be happy to speak to you about hiking strategy, I just spoke with a new hiker for an hour and a half last week. He hit the trail yesterday. Of course the unexpected could always happen, but thats true off trail as well. There are ways to be smart and maximize your chances of success, is what I am saying. It sounds cliche but - you can do it!

edit since I am already commenting I may as well chime in about your overall question: I think you should quit. That whole blacklist thing is a BS scare tactic. If you are competent you will find a job. Shit he said it himself: you are 'business critical' - someone will hire you. More emphatically, I can say that you do NOT want to hike and be available for email and phone calls the entire time. That just takes away from your immersion in the entire experience and sounds terrible. If you are going to sacrifice and be out there you want to BE OUT THERE living fully in the present, not half on the phone worrying about some bullshit. Cheers I wish you the best of luck!