25 years old full of potential: tempted to go O/O

Here's a post of mine from 3 years ago:

22 w/ 40k saved... what do I do with my life?

Update:
I'm 25 now. Will be getting Associates in Engineering in 2 months at a Community College. Knocked out all my Calculus/Physics. I've got a 3.6 GPA and I'm involved in all kinds of clubs and activities. I'm on the verge of potentially transferring to a University but I'm just not feeling it. I've applied to one university, a couple internships. Seeing what comes of it. I keep changing my mind between different branches of Engineering. Can't decide on anything I have a true "passion" for.

Trucking is still in my blood. I've been trucking still during the summer and winter breaks with a company. Great company. They've worked with my school schedule. Everyone in the office knows me. Great people.

I remember that year when I was 22 with a goal set for myself that I was chasing and it felt good. I was out there hardly communicating with anyone and I didn't care because I was so focused on saving that money. I expected college to bring out the same focus but I feel like I've completely dragged myself through this. It's hard to explain because my grades are good but I just have no motivation to ever study. I'm always procrastinating and stressing out about tests. Last year and last semester I was smoking weed all the time but I've stopped that. I guess I was just that bored.

Overall I describe my current feelings as being restless, no direction. Like there's a void. Like I need a change of scenery and a new goal/purpose.

I don't consider my community college experience a waste of time either. Feels good to finish something I started. If anything, I'm at a good "stopping point" where I could easily go to a University in the future. Also in doing this, I moved to a town that I was born in but never got the chance to grow up in. Always looked at it on the map and said "Man I want to check this place out one day." What better way to do it than go to college there. Here I am 2 years later and I feel like I've lived here long enough to feel like it's "home." It's been a great experience and college has been fun. I'm extremely popular on campus. Over the breaks when I go trucking I have about 100 college kids (and even some faculty) that follow me on Snapchat. They all think trucking is the coolest thing ever. I've enjoyed every part of college except the part where I have to think about careers.

I still have a CDL, over 300000 miles with no issues, and close to $60k saved. Community college was cheap. A University would eat up a lot of that 60k. If I transfer to a University I'll be graduating in 2-3 years with much less money than I have now, and a degree that I'm worried that I will not be passionate about but will feel obligated to try to make good on my investment. I'm a smart guy and probably very capable. But I'll never become the best I can be at something I'm not passionate about.

I feel like a total free agent to life right now.

I spend a lot of free time looking at real estate. Throughout the last 2 years I've had several periods of 2-3 days at a time where I am so distracted from school because I am fascinated in doing this research. I also got into stock trading. It's nowhere near being dependable money but I enjoy learning about it. I feel like at my age buying property should be of the utmost importance and would be the best way to really get a leg up so to speak towards building wealth. I want to buy property. My idea now is to go back into trucking with the explicit goal of buying property. I want my first property to be a multi-family property, preferably a fourplex. Eventually I think it would be cool to own apartments, student housing, self-storage facilities, etc.

The trucking life does grind on me, but I've only ever been a company man. I've got a buddy that runs with Landstar, with a freightliner he bought from LoneMountain and it sounds awesome. Like a completely different trucking experience than what I've had being thrown up and down I-95. I'm really tempted to go this way before I throw money at a University. And, I feel like I've peeped the trucking game and understand it a little better than I did when I was 22.

I grew up in a traditional family where everyone goes to college, gets a job, 401k, etc... During my 2 years OTR I would go home for thanksgiving and listen to extended family members that I haven't talked to in years tell me that I need to go back to college. It worked for them. I feel like I have made my best attempt to follow in those footsteps. It's one of these things where if I went back to trucking I'd have to decide that I have no time to explain myself to anyone. As it is, I'm not much of a family person anyways. I've been living on my own in different states and haven't taken a dollar from anyone since I was 20.

It's one of these things where I wonder. How good would it feel to bet on myself? What would happen if I bought a truck, put my head down for a year and went back into grind mode. Run everywhere out west with my guitar and my set of disc golf discs. Right now I'm interested in buying one property (preferably somewhere south like Nashville TN, or Texas because I grew up there, or St Louis because I used to live there as well and I know about it) which I could probably do within a year. How fulfilling would that feel? If that goes right, who knows what my opportunities could be in the next year after that? Where would I be in 2-3 years? I can only imagine. I feel like if I can manage to own a single truck and a few properties before I'm 30 I'd be in a much better position than a degree would have me in. Eventually could back away from trucking too.

So somebody give me the real deal on Landstar. Is it a good place to start? I've got money, credit, experience. I obviously am good with money. Am I thinking realistically here?? Are there different avenues to look at for O/O? Where's the best place to look to buy a truck? Is LoneMountain a good source?

I gave you all a lot to read but this seems to me like a good place with the right perspective. Too many people I talk to will start in with "Well you know, automated trucks..." Right... Hope to get some good input here. Like I said I don't consult my family a whole lot on this type of stuff because I know what they would say. I feel like I've got a solid well thought-out plan and emotions I need to act on. What say you?

Thanks for reading

 

Just to clarify. I drove 2 full years of OTR before I started college.