Overcoming work history gaps / getting foot in the door in 2018

I've been doing a lot of reading but I wanted to get some ideas from drivers/people in the industry here. I got punched in the gut yesterday when I finally called Millis to inquire about starting school with them. I've been unemployed most of this year due to taking care of my Grandmother and my work history going back to 18 isn't that great. I've moved around a lot of my life and was mostly self employed up until a few years ago. My home town doesn't have many great job prospects aside from temp. work so I've been hopping around to different temp. jobs after they lay off seasonal workers every year. Did a little stint as a security guard and worked in a bakery as a helper for awhile in there too.

Basically, my work history sucks and I can't provide pay stubs/W2s for most of my work history because I was doing under the table work and/or odd jobs for friends to get by. My background is in computer programming and a lot of my income came through doing freelance work and living on donations from that but it was never enough to claim on taxes.

I want to break into the industry and stay with a company long term. My plan was to go to school through Millis because they were local but it doesn't look like they want to work with me or give me a chance. What are my other options? Should I just pay for CDL training myself at a proper school and hope for the best once I get out? Will a company like Swift take a chance on me so I can prove myself? I'm tied to this area due to family obligations and at some point I want to earn enough money to build myself a house on the family farm and maybe go O/O but it seems like I can never get started. No one in the local area pays more than $9 an hour and getting anything beyond part-time hours seems impossible. I feel like I just can't escape the depression that's overcome this town in the last few decades. Almost everyone I know has given up and gone on disability/Government assistance. I can't even name 2 people with a proper career in the area my age because there are no prospects.

I'm already 32 years old: Do I have to go flip burgers or work at Wal-Mart stocking shelves for 3 years before a company will even consider me?

 

By "stay local" I meant I'm tied to the area due to the family farm. Other family members can take care of that while I'm away. I want to go OTR and this job is kind of an excuse not to have to be around the farm everyday if I'm being honest.

I just meant that when I do get home time this is where I'll be spending it. My plan is to work my ### off OTR so I can make sure my Grandmother has enough money for food/taxes/home care. My father is retiring this month so the main reason I've needed to stay at home so often is now taken care of. I didn't mean to imply that I didn't want to go OTR. I'm willing to drive to where ever they want to send me for as long as they want to keep me out. I'd actually prefer staying out for months at a time and saving up home time to take all at once. I have no need to be home every week or anything like that.

 

I understand that they're mainly looking to document where you've been and what you've been up to these last few years. When I called yesterday I inquired about this and was told flat out: nope we need W2s and paystubs. I can get notarized letters stating that I've been taking care of family, doing farm work, and doing work for people in the area. Lots of folks willing to vouch for me.

I was just kind of surprised they were so quick to dismiss me like that because I'd heard from people here that Millis would work with you. Millis was really appealing because they have a terminal in the small town I live in and I'd heard so many good things from current drivers. Perhaps I should try again and hope to speak with someone else?

If I do end up going to a driving school myself is there any in the NC/VA area you guys would suggest? That was one of the reasons I wanted to try going with Millis because I heard they were really strict in training. I've heard the horror stories about places like Swift. I want proper training if I'm going to pay for it and while I know it isn't going to prepare me for everything I don't want to get OTR and find out I'm not prepared.

I'm willing to work a slave wage for a year if that's what it takes to get in with a decent company. I do eventually hope to either have my own truck or save the money from this job for starting my own non-related business. My ultimate goal is to be independent.

 

I have enough saved up to pay for CDL school. Paying cash for it right now isn't my issue. I'll inquire about this though thanks.

I called their 1-800 number yesterday and it was the first thing she asked about and refused to speak with me further when I said I have a year gap in employment.

Concerning tickets: My driving record is mostly clean. I had a seat belt violation many years ago and a speeding violation that I pled down to improper equipment. Is this going to screw me?

Sorry about all the questions. I just really want to break in and get started.