Which is better to work for a company or be a independent operator?

You won’t have to wait to retire to drive semi trucks. Some trucking jobs can be a very good fit for off duty employment. Local P&D or short haul private fleet jobs worked the best for me. I drove trucks on my days off most of my career. You just have to find the off duty jobs that fit your schedule. I was a company driver most of the time but I was also a short haul owner op during some of my FD years.

 

To add an example to @Banker .
My brother in law farms spring, summer and fall. Winter he hauls propane.

You might not want to do that, but it's just one example.

 

If Holland has a terminal near you this could work. The larger terminals need and use Casual(part-time) dock workers in the evening. If you get a good reputation as a hard worker who is dependable and energetic and buddy up to the yard drivers, they may eventually let you work in the yard moving trailers around some. Then one day when you have been there several years and you are 21 they may actually train you to get your CDL and work you a couple days a week driving in the city. Some Holland terminals don’t work any part time drivers, so don’t get discouraged if the one near you doesn’t. Most LTL Freight Companies years ago used Casual drivers to work dock and drive. ABF at some locations still does and I am sure if you look hard enough you will find a company that does. Another option is most Ready Mix Cement companies hire part time drivers, but you need to be 21 with a CDL.

 

A lot of those freight companies you listed are actually by where I live! So what you suggested could actually be a possibility for me So thank you for suggesting that! I honestly had never thought of that before!

 

Sorry for getting to the party a little late, but I'll chime in for what it's worth.
It's a great idea to get your class A CDL and there's ways to do that if you look around. I would suggest getting the license, but remain in your studies and not actually driving the truck.
I'm an independent trucker with my own authority, and it takes years of experience to handle that level of responsibility, it's very expensive to set up and it takes a lot of hustle to maintain which is not something you'd want to take on as a new owner at 18 years old.
It's just a lot to look after and cultivate.
Having the license creates other possibilities for you without adding tons of financial and legal responsibilities. Plus your career path is a really good one. Much better than trucking in may ways and it's much more consistent and stable. Fire fighters are the cream of the crop in terms of occupations, respect and necessity. Even though truckers are pretty much the same thing in terms of necessity, we're often viewed as dirt, disposable and unimportant or not vital to an economy; so, we don't get any respect.
Avoid all of that.
Stay on your career path and keep the CDL so you can work your way up to driving a ladder. I have a good friend who does it and he started out in a smaller department and moved up fairly quickly.
Good luck little brother, wish you all the best

 

I'd say go work for a local lumber yard driving one of their flat deck straight trucks (the ones with the Moffat forklift on the back). Might be more likely to find something like that for 2 days a week for 8 hours a day. I've never seen the appeal of OTR driving and chasing miles. Myself, I'd be far more interested driving a small tandem flatdeck around town.