Taking another swing at it

First my truck has to qualify. Thus the sticker.

 

I'm considering getting my own authority and renting a trailer. That old O/O I met all those years ago has that line that is still haunting me.
"You can be a company man, or you can be your own man."

I'm an O/O myself now, through failing into ownership by doing it all wrong.
I'm driven to take it to the next level. Obviously I'll wait until spring when freight gets on the upswing again.
(And more ducks are in a row)
Only then will I feel that I have completed the mission

 

Sometimes I think I sleep better in my truck than at home in my king size bed.
I've heard stories of retired truckers with a master bedroom, but they put a bed in the walk in closet because it feels more comfortable

 

Thank god hockey season is upon us!
Due to the loader screwing up, instead of a load to MI. I ended up with a load to FL. Hopefully they unload me tomorrow as its scheduled for Wednesday

 

Rain rain rain. Going to atl for a 2 stop tomorrow then a run back.
Supposed to be home Saturday but we will see how juicy of a load they offer.
I'm reminded this week, the more you make, the more things pop up that you have to pay for. No such thing as extra money.

 

I looked into a quote for insurance if I made the leap on my own with my own trailer. Just under 10k annual or about 2800 down and less than 1k/month. Trying to figure out if it would be worth it.
Seems every time I go forward lately, in hindsight I thought I was making "good money" and by comparison I wasn't. I wonder if that will be the same outcome of I make the leap.
I know I need a couple of months of expenses saved up before doing it, for eventualities that can, will and do happen.

Will I look back and ask, why did I wait?