What Should My 2nd Trucking Job Be Once I Reach 1 Yr, 100k Miles Experience?

Hello, I haven't posted/visited this forum in a long time. Been busy.

Spent most of last year going from zero knowledge/experience about the trucking trade, to successfully getting a 2yr DOT certificate and a Class-A CDL in November through Wilson Logistics. I'm not a solo OTR driver with them.

During the training, I did 25k team driving training with a trainer, and then 30 or 35k team driving with a student.

This isn't the first time I broke into a new trade. Last time it was welding. I spent the first 7 years straight out of welding school getting rooking level jobs to use to make all my rookie welder mistakes, get fired due to those mistakes, learn from it, etc until I got my first professional level job fabricating bulldozers for Caterpillar. COVID shut the factory down and that led me to door dash and that eventually led me to trucking since I discovered through door dash and even delivering for Amazon that I enjoy driving for a living more than I did welding for a living.

I assumed that my experience breaking into the trucking trade was gonna be the same as when I first became a welder. First year always sucks. That's when you make all the mistakes you HAVE to make to learn the things you'll never learn in the class room.

...But my performance as a year one rookie isn't as bad as I thought it would be. So far only been late for a delivery once since my training days and was still able to deliver, and still no accidents. I kind of assumed my performance would suck, I'd make all my rookie mistakes with Wilson and then when I get a second trucking job, that's when I would perform a lot better just like how I did with temp welding jobs VS Caterpillar.

Most of the really good paying jobs I've seen in the trucking trade via indeed require 1 year and 100k miles of experience.

So I'm staying with Wilson Logistics until I meet that 100k/one year milestone in my experience before seriously looking for another, better paying trucking job. Best case scenario, I'll just stay with Wilson Logistics the whole time because I only plan on being a trucker for 2-3 years to save up a bunch of money and then I'm immigrating to Mexico to buy/build a house outright, become an english teacher, then go back to college and finish my education in math, engineering and physics so that I can become a STEM professor some day.

Because of what I'm trying to accomplish with my life, recently paid off all my debts before even becoming a trucker, have no wife or kids and won't even date again until I'm in Mexico, and won't even go back to college until I'm in Mexico, if for some reason I end up leaving Wilson for a 2nd trucking job instead of staying for my 2-3 years as an OTR trucker, what would be yalls advice on what company to apply for?

If it helps yall answer my question, I would only apply for the kind of OTR trucking job in which I would be living out of my truck and never going home. That's what I'm doing right now and wouldn't leave Wilson unless there was a better paying trucking job once I reach my 100k miles/1yr experience milestone.

Technically speaking, I'm homeless and my truck is my home. My sister lets me use her address as a physical address to have on my ID paperwork because you can't function in society without a physical address. Everything I own is either in my truck or in two storage tubs in my sister's shed. The idea is to own as little as possible so when it comes time to immigrate, I can move to mexico with just the clothes on my back, my passport, and a few luggage bags.

Currently, company drivers at wilson are getting paid .50/mile and get 1,500-2,400 miles/week.

I was a company driver for Wilson Logistics for a month, so I could learn how that works. I'm now a lease operator for several months before I go back go being company driver because I simply wanted to "experience what it's like" to be a lease operator haha. I literally became a lease operator just out of curiosity so I can experience the difference between lease operator VS company driver. And I do plan on becoming company driver again several months from now for obvious reasons that are mentioned many MANY times on this forum. :)

Should I stay at Wilson for the rest of this year, next year, and worst case scenario a third year before immigrating to Mexico, or is there a more lucrative option for me as a basic Class-A CDL driver who really enjoys living on the road, once I hit my 100k miles/1year experience milestone later on this year?

oops, there is a typo and couldn't find the edit button lol.

I meant to say "I'm now an OTR driver for Wilson" not "I'm not an OTR Driver for Wilson" lol

Hello, I haven't posted/visited this forum in a long time. Been busy.

Spent most of last year going from zero knowledge/experience about the trucking trade, to successfully getting a 2yr DOT certificate and a Class-A CDL in November through Wilson Logistics. I'm not a solo OTR driver with them.

During the training, I did 25k team driving training with a trainer, and then 30 or 35k team driving with a student.

This isn't the first time I broke into a new trade. Last time it was welding. I spent the first 7 years straight out of welding school getting rooking level jobs to use to make all my rookie welder mistakes, get fired due to those mistakes, learn from it, etc until I got my first professional level job fabricating bulldozers for Caterpillar. COVID shut the factory down and that led me to door dash and that eventually led me to trucking since I discovered through door dash and even delivering for Amazon that I enjoy driving for a living more than I did welding for a living.

I assumed that my experience breaking into the trucking trade was gonna be the same as when I first became a welder. First year always sucks. That's when you make all the mistakes you HAVE to make to learn the things you'll never learn in the class room.

...But my performance as a year one rookie isn't as bad as I thought it would be. So far only been late for a delivery once since my training days and was still able to deliver, and still no accidents. I kind of assumed my performance would suck, I'd make all my rookie mistakes with Wilson and then when I get a second trucking job, that's when I would perform a lot better just like how I did with temp welding jobs VS Caterpillar.

Most of the really good paying jobs I've seen in the trucking trade via indeed require 1 year and 100k miles of experience.

So I'm staying with Wilson Logistics until I meet that 100k/one year milestone in my experience before seriously looking for another, better paying trucking job. Best case scenario, I'll just stay with Wilson Logistics the whole time because I only plan on being a trucker for 2-3 years to save up a bunch of money and then I'm immigrating to Mexico to buy/build a house outright, become an english teacher, then go back to college and finish my education in math, engineering and physics so that I can become a STEM professor some day.

Because of what I'm trying to accomplish with my life, recently paid off all my debts before even becoming a trucker, have no wife or kids and won't even date again until I'm in Mexico, and won't even go back to college until I'm in Mexico, if for some reason I end up leaving Wilson for a 2nd trucking job instead of staying for my 2-3 years as an OTR trucker, what would be yalls advice on what company to apply for?

If it helps yall answer my question, I would only apply for the kind of OTR trucking job in which I would be living out of my truck and never going home. That's what I'm doing right now and wouldn't leave Wilson unless there was a better paying trucking job once I reach my 100k miles/1yr experience milestone.

Technically speaking, I'm homeless and my truck is my home. My sister lets me use her address as a physical address to have on my ID paperwork because you can't function in society without a physical address. Everything I own is either in my truck or in two storage tubs in my sister's shed. The idea is to own as little as possible so when it comes time to immigrate, I can move to mexico with just the clothes on my back, my passport, and a few luggage bags.

Currently, company drivers at wilson are getting paid .50/mile and get 1,500-2,400 miles/week.

I was a company driver for Wilson Logistics for a month, so I could learn how that works. I'm now a lease operator for several months before I go back go being company driver because I simply wanted to "experience what it's like" to be a lease operator haha. I literally became a lease operator just out of curiosity so I can experience the difference between lease operator VS company driver. And I do plan on becoming company driver again several months from now for obvious reasons that are mentioned many MANY times on this forum. :)

Should I stay at Wilson for the rest of this year, next year, and worst case scenario a third year before immigrating to Mexico, or is there a more lucrative option for me as a basic Class-A CDL driver who really enjoys living on the road, once I hit my 100k miles/1year experience milestone later on this year?

Sure seems like you may have answered you own question. You have a plan and the future doesn't seem to involve trucking. You've developed a good relationship with your current company and you don't seem to have any issues with them. One thing I've learned about this industry is the grass isn't always greener. In fact most of the time you'll find you would have had it better if you just stayed where you were.