how difficult is it to get my cdl without going to school?

Check with your DMV some states required to get certified

 

And a lot of companies require it too. Or X-amount of experience.

 

Depends what you do next O/O or company driver

 

Worthy goal & you DID say one day......

Don't put the cart before the horse, though.

Check out your local community college. Likely have something that will work for you, especially if wanting to keep current employment while getting that CDL.

Most community college programs are recognized & accepted by a majority of carriers out here.

Bonus of going that route.... Will also relieve you of term obligation (up to a year) most require of you, if you get license through their own programs. But, that route seems to be moot point, as you want to obtain CDL while holding your current job.

Don't forget to check in on state/fed programs that may grant you all or most of going there, depending on your situation. Low income is NOT necessarily a part.

Good luck.

 

Which city/town are you near in Michigan?
One thing you can do right now is become a member of www.OOIDA.com which is a business website for the owner-operator. Get prices on insurance that you will need for your truck business, as an owner-operator with no experience.
In the meantime, become a company driver to gain experience & after a couple of years, take another look at becoming an owner-operator and check insurance prices again.