3 yrs exp, but left trucking 4 yrs ago making $120K+, where do I pick up?

Hey guys, long story short, I drove for C.R. England as a Phase 1 Trainer from 2008-2011, and made roughly $120K+ for each year I was there.

With all of the money that I saved, I quit and tried to start many other unsuccessful businesses that flopped, lost a lot of money in the stock market, and basically made poor investment decisions.

I also made about $100K for 2 months in 2013, but have since been unable to replicate that success.

From there I bought and sold items on eBay and Amazon FBA, and made $25K or so in 2014.

In November 2014 , I took care of my 2 year old son, while my fiancee in the Air Force got deployed. I told her not to do it. She did it, and when she returned, our 4 year relationship was ended.

I want to get back on the road and start making serious money again, and I also have 3+ years experience, but haven't drove in the past 4 years. So my question is, where should I start this time? I am dirt broke, staying with my stepmom currently, with $3 to my name. Where should I start, if you guys were in my shoes?

I know that I want to at least be making 100K+ a year for at least a few years. Trying to see what would be the best course of action to take, or if I would be better off working a local job with benefits and just working a second job as well.

I need your guys advice. I do want to do a career change to computer programming and coding (java, javascript, python, ruby etc) but just not sure how to do it. Plus being dirt broke doesn't help.

Any advice is appreciated!

Edit: So it seems, I won't be able to break $100K unless I train again, but I don't want to train. That stuff takes its toll on a person. So I have adjusted my expectations, and reasonably, someplace where I can make $50K-$65K if I really ran hard, and they paid pretty decent. I don't care about miles, because I can dictate my own miles if I can get to a good company and do most of my DM's job for him, and possibly even pre-book my own loads.

 

Lol, your probably right. Once I learned the system, I took advantage of it. I ran 4 basic routes, east coast to west coast. It wasn't too hard. I also had a good DM, or at least I force him to be a good DM!

Once I learned the Smithfield, Conway, FedEx, and FreshExpress routes, it was easy for me to get 6000+ miles a week consistently. Of course, I would always call up my DM and tell him to get me loads from these places. Many times I would deadhead 200-300 miles just to put myself in an area where I knew loads where constantly moving east to west coast, and vice-versa. Whats $150 out of pocket for fuel, to get a 2000+ mile reload was my thinking? Chump change when I'm moving 24/7 OTR

You could say, I mastered the system at CRE somewhat.

 

The only thing is I only want to do about 2 years OTR from this point on. Not 2 years, then more years after that. My goal is to save up again, then try my luck in Silicon Valley! I also want to move to SanFran and just be in that area once I'm more stable.

I'm not sure if your serious or joking? How are they paying that much if you don't mind me asking? When I was their I was grossing $220K-$250K a year, and taking home $120K or so. How are they hitting $375K? Higher mileage pay? Curious