Successful OOs if you were starting out new, how would you do it?

Discussion in 'Ask An Owner Operator' started by truckovation, Feb 15, 2026.

  1. PSM379

    PSM379 Heavy Load Member

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    I wouldn’t call myself successful by any means. I am getting by, and when it boils down to it I love what I do. I wouldn’t have listened to all the negative people, some I think were just giving me negative info so I wouldn’t go out on my own. I would have done it once I started out. Own authority, truck and trailer. I would have incorparated from day 1, instead of operating as a sole proprietor under my own name. I truly do not think I could walk away from this. As stupid as it gets some days I truly don’t think I could walk away. At 39 I still eat,sleep and breathe trucks. Not many folks can say they are doing what they said they’d do since they could speak. If anything the stupidity on the roads would possibly make me walk away, I’d try to be involved with trucking and old trucks somehow though if I did.
     
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  3. OldeSkool

    OldeSkool Road Train Member

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    I was an owner operator for around 7 years. Done fairly well with it. I quit because I moved north and didn’t have any of the connections up here I did in the south. Now I work for a company. Honestly if I’m going to stay trucking I’m gonna stay with a company. If I got out of it and was able to do anything I wanted I’d be an airline pilot. I am very fascinated with airplanes. But my wife and kids come first so don’t see a career in flying.
     
  4. sirjeff

    sirjeff Medium Load Member

    If I were to start over again... My first truck would have been just broken in instead of brand new, and I'd get into deck work right away instead of trying to be the guy "who made it" hauling wood chips

    No regrets, though. Doin quite fine and learned a lot along the way
     
  5. Opendeckin

    Opendeckin Medium Load Member

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    I think many saying they would have chosen a different path fail to realize how much those other paths suck. I did good trucking early and hit a 6 figure retirement by 27 years old and have been coasting for a while now figuring I’d find something else to do, but the more I think about it the more I think staying trucking is ideal.

    machinist don’t get paid worth a #### and don’t have much room to advance. Diesel mechanics destroy their body. Electricians could get shocked to death anyday and have to navigate tight spaces a claustrophobic person like me couldn’t handle. Welders get cancer and messed up lungs.

    also to the guys saying just go company and make they same are failing to account for the tax difference which if you have a good CPA Is Massive. W2 guys get royally ####ed.
     
  6. Arctic_fox

    Arctic_fox Experienced mx13 execrator

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    Get a PPL, they arent that expensive if you spread the cost out over a few years. Around 60-70hours average at $150 an hour at the high end. Spread that over 2 or 3 years and it costs less then superbowl tickets per year. And once you have your PPL you can rent planes to casually build time and just have fun. Maybe get an IR rating as well. Wont be the same as being a professional pilot but flying is by far one of the most fun things you can do and would be a fun thing to take the family off someplace in a plane.

    Just remimber though. You cant pull a plane over, so safety safety safety. If its dumb and boring. Do it anyway because the rule was written in the blood of the dude that ignored that rule or didnt have that rule at the time.

    There are a few points your missing there. Namely home time, getting to see your family and friends enough to actully be involved in their life. the fact that trucking can mess your health up just as much as say a welder getting lung cancer (go look up bladder, back and prostate problems/cancer rates in truckers, its an eye opener. 50 to 500% more likely for bladder cancer depending on how many years you drive for....as a non smoker for instance. The percentage for smokers is in the thousands of percentage more likely and ive seen reports as high as 7000% more likely depending on the source) the fact that while those jobs CAN be dead ends a diesel mechanic doesnt mean just trucks. See trains, heavy equipment, generators, ships and boats ect. Lot of guys who get to those fields make bank. Mechanics same thing, car mechanic makes peanuts, a mechanic with an A&P can get around 70-100K get some certs for jets and turbine and that goes up by a LOT.

    Its just like trucking. If you just look at the 1099s and companys like western express. Truckers are basically starving to death. You get some experince or go for more specialized you make way more cash.
     
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  7. Opendeckin

    Opendeckin Medium Load Member

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    I wouldn't recommend OTR trucking that's for sure, but I find you can make good money being home every other day and/or every weekend. I'm never gone more than a day and hit the gym 3 days a week minimum. All my work is and for years has been straight out and back. It's worth noting that many trades guys live on the road for extended periods chasing work. Sometimes months.

    The bladder/prostate cancer isn't something I was aware of. That's good to know and I'm sure my risk is worse since I run a 3406E.

    For sure every industry has it's tiers. Not saying none of these other trades have bright spots. I'm just saying if you asked the veterans in those trades if they would do it again if they could they'd probably say no as well.

    Grass is always greener I suppose is what I'm getting at.
     
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  8. Short Fuse EOD

    Short Fuse EOD Road Train Member

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    If I started over as an owner operator again, what would I do different? When getting started with new customers, I would have been less choosy on what lanes I prefer. Knowing what I know now, my favorite lane is the lane my customer has the most trouble covering. What would I have done the same? Started out with a customer instead of all in on load boards. Using only new equipment Is something I would repeat as well. That worked for me and I’m still here doing my thing.
     
    Last edited: Feb 16, 2026
  9. Blu_Ogre

    Blu_Ogre Road Train Member

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    I am from an entrepreneur and business owner background, and a 3rd generation driver. I was a leased to a carrier, self dispatched from internal load board.

    A bunch of those answers would be location and customer base dependent.

    Living in Salinas, CA most of the freight was either harvest related or refrigerated out. Also mostly nonexistent in the winter. Had to figure on deadheading out Thanksgiving to Easter.

    I moved up to the PNW - I5 Corridor. Containers and cars from the ports along with lumber industry are the volume leaders up here. There is a good amount of general freight that comes in, not so much going out. Doing dry van, I would tend to grab freight from trade shows, freight import houses, or local manufacturing places and haul it south. Return trips, which tended to pay better, tended to be trade show/convention things or chemicals to be used by production places.

    Looking forward, I do not have a positive feeling for the industry. I believe the Owner op community will continue to suffer under the Amazon type dispatch systems. I would be reluctant to encourage anybody to get into being an Owner op now unless they had a solid book of direct customers. I am kinda soured on the industry as a whole, which is why I did not renew my CDL.
     
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  10. MTMAUS

    MTMAUS Light Load Member

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    I can't say what I would or wouldn't do, because I don't know haha.

    What I can tell you is, if you are starting out, you need to be prepared to do it for 15 years.

    First 5 years - Lucky to earn a wage, wonder why the hell you are doing it.

    2nd 5 years - Things are getting better, starting to make some money.

    3rd 5 years - Wonder how you are making so much money, and why couldn't it have been like this from the beginning

    However by year 15, you will hate driving, body will be shot and start to plan your exist.
     
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  11. OldeSkool

    OldeSkool Road Train Member

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    I don’t buy that about taxes and CPA. I used at least three separate CPA’s and yes they really were CPA’s and the one I finally used was an out of state guy that was supposed to be super good with trucking. Every one of them I paid high taxes and everyone told me the same thing. Sole proprietors get hit the hardest on taxes since they don’t have employees.

    The only guys I know that didn’t pay high taxes that owned their own truck did shady things like business trips for vacation and turned everything in they bought pretty much as businesses expense. Might as well just sell drugs if you aren’t going to operate legally anyway.

    Edit: Sorry about my rant. Nothing personal but I just had years of paying taxes out the nose and got tired of hearing I shouldn’t have to but none of my tax accountants seemed to have that idea.
     
    Last edited: Feb 16, 2026
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