WEX Systems Admin to trucker? (MAINE)

A little about me, I'm 40 years old and for the last 16 I have worked at WEX (formerly Wright Express) as a systems administrator. Some of you may be using our fuel cards. I do tech support and maintenance on the computers that authorize the fuel card swipes, process the purchasing data and odometer readings, and send out the bills. Although I don't interface with the business or customers much, I'd like to think I've been helping a lot of you keep your fuel tanks full and trucks on the road.

Unfortunately for me, WEX has decided to outsource the entire IT department and my last day will likely be in mid April. I could perhaps get a job working for the outsource company (CSC) but in all likelihood it will be a painful transition and my job there would be offshored to India after one year. I'm very disappointed but excited to be able to look at opportunities outside of WEX without any strings attached. In my 16 years there I have only interviewed once outside the company.

I am interested in CDL work as a second career, or something I can do between IT jobs. I predict that outsourcing and offshoring in the IT field is just going to get worse. For some of my co-workers this is the 3rd outsourcing they're going through.

I am fascinated with diesel trucks and equipment. For the last five years I have been fixing up a 1966 surplus military three axle deuce-and-a half. I taught myself how to drive stick on its five speed Spicer transmission and Rockwell two speed transfer case. I have changed all the fluids and filters, greased all the zerks, replaced the radiator and starter, upgraded the fuel and oil filters, and replaced about 40 feet of brake line. I own a 45hp Yanmar tractor and learned how to use its loader and pallet forks, and figured out how to install a remote hydraulics kit on my own. I also tinker with air tools and mig welding. I'd like to think these hobbies of mine would be beneficial experience in operating a heavy truck and dealing with unexpected problems with equipment.

Financially I'm in pretty good shape. WEX has been good to me and I have a 401k nest egg for retirement. My immediate needs are to keep paying the mortgage, taxes, and utilities. CDL work will be a pay cut in the short term but at least the jobs are there and the pay is within my means. I'm married but no kids, my wife does encourage me to get a CDL and/or find a second career outside of IT.

I will admit I'm a bit of a homebody, my ideal off time is puttering around home working on projects, seat time in the farm tractor, or harvesting firewood. So I think I would mostly be interested in regional work or home heating oil delivery, but I would like to experience OTR. Are there companies that offer a mix of both? Or perhaps just part-time assignments OTR? Having spend most of my career in a cubicle, however, I am interested in new sights and scenery that CDL work has to offer.

I am very good with electronic map navigation and planning road trips. I've helped my brother move between Fort Campbell and Fort Lewis, and Fort Sill, and enjoyed those trips immensely. The largest truck we drove on one of those trips was a 26K GVWR Ryder Box truck while towing a car on a dolly. I have also used a towbar to recover another deuce-and-a-half safely 75 miles away. When towing the trucks together I linked the gladhands from the front truck to the brake booster on the rear truck for extra brake power, it worked great, and love playing with stuff like that.

I don't think it would bother me much by touching freight and/or operating a fork lift. It'll probably be good exercise anyhow - I say that now, naively. I also realize I need to pay my dues. I have spent most of my career in 9-5 cubicle, but I'm not afraid to get dirty and work. Snow plow or dump truck operations are other interests I think I could get into.

For CDL training it would be very convenient for me to enroll with NTI in Scarborough. I have sat down with them and passed the initial screening interview I have a stable work history, no accidents, and my last speeding ticket was over 10 years ago.. Although I think the cost ($6500) is a bit expensive I do have the money to cover it. In any event, I realize CDL training is just skimming the surface and there's a whole lot more that needs to be learned.

Well, that's my skinny and I hope its not too long winded. I would love to read any advice you have about learning the ropes or landing suitable work out of Maine.