Comments By Ithel

Congratulations to you both on passing your CDL tests. But congratulations also for 39 years of the intimate friendship known as marriage.

I came very close to closing my business about a year ago and getting into trucking, but the timing wasn't quite right. Some family circumstances have changed, and I'm ready to do this.

Many thanks to the experienced drivers on this board who have enabled me to think this through as clearly as possible from the outside. I'm not completely at peace, giving up as I am a profitable though unsustainable business, but I'm as close as I have ever been. I've discussed this with some trusted friends as well as my wife and daughter, and I think we're all on the same page now.

I've been talking with Mike, a recruiter at TMC. Their CDL classes are open to people from Kentucky, where I live. I had to submit copies of my tax returns going back to 2012, since I am self-employed. I'm waiting to hear from them now.

As I learn more, I'll post again. For now it's jumping into High Road and learning/relearning a lot of things so I can go to Iowa with my permit.

You will give this friend a Form 1099 in January 2018. Like W-2 forms from employers, you need to have sent it to him by January 31st. You will fill out and file Form 1096 with the IRS (by February 28th) so that the IRS can match the 1099. Don't forget to include this amount on your own tax filing as a business expense. You can contact the IRS to have them send you a blank version of the Form 1096, unless you use tax software that includes the ability to e-file that form. (Generally, this is a form you can't just print off on blank paper and expect the IRS to accept. The 1096 form looks like this: https://www.irs.gov/pub/irs-pdf/f1096.pdf If you have your own business I'm sure you already are familiar with a 1099.

No penalties unless for some reason you miss those deadlines.

I hesitate to jump in here, as I have mostly lurked this past year and am not a driver, but as a small-business owner who advises other small-business owners at tax time, my advice is that going into business in this new path for you is a very bad idea. Owning a business is far more complicated than most people imagine it to be. Even from the outside I can see trucking has a tremendously steep learning curve that will require your concentration and diligence. Learn how it works and gain some experience before adding the complication of also learning how to run a business. It would be painful enough to find six months in that trucking is not as workable for you as you thought.....how much more painful if you also now had investments you cannot easily recover!

There are better ways to approach this, and this site has many resources to help you decide how to make the most of your opportunities.

My 2 cents.

Given the additional weekly costs listed here for certain situations, I'd assume those are weekly premiums. But call them to make sure. http://www.roehl.jobs/roehljobs/media/sitecontent/Documents/2017-New-Employee-Benefits-Summary-Student-Driver.pdf

I realize that a smart business person would be able to turn my business into a commodity that could be sold, but I am not that person. The one thing that has allowed me even what success I have had is personal service. When someone calls me for help, it's me they get, not an intern or a seasonal temp. Aside from that, with the liabilities in the tax industry being so outsized compared to the compensation, I would be exceedingly reluctant to turn things over to a helper. I think the process of double-checking someone's work would take me longer, honestly, than simply doing it myself. I realize the tax chains do it differently, for that is where I started before setting out on my own a decade ago. I also have pretty deeply held philosophical objections about earning money off someone else's labor. Again, I realize that is an extreme minority outlook that few would agree with, but it is nevertheless a line I would not willingly cross. That's not necessarily a line that is crossed by a finder's fee, but it does give me pause.

Having said all that, I did finally reach someone at Online Transport today who was able to answer my questions. It is a no-touch situation, 7pm-7am four nights a week, with overtime pay. It can be any night. All that was a plus. But I asked about how long the trips were.... it turns out this is entirely warehouse to factory to warehouse, all within the same little city about five miles from home. So correct me if I'm wrong, but this sort of work would not even count as driving experience if somewhere down the road I applied for a different kind of trucking? That's my understanding from what I've read here on your forums. She also said she was surprised that anyone had proposed that particular driving account to me, as normally 6-month experience was required. She said there was no guarantee it would be available, as they had several other applicants already. Their training is once a month, and I've just missed it for this month. The next training begins Feb. 13th and lasts seven weeks, pushing this out to near the end of March.

Old School, your post was such a relief to me, honestly. The factors in play aren't precisely what you've described, but they come pretty close. The personal stress has never been higher, and if I could have sorted things out more quickly, my decision would be clear. But given the above, I feel I've backed myself into a corner so far as the current tax season is concerned. I'll just do everything I can to take care of my clients one more season then revisit my options in May. The writing is on the wall, as they say. But if I can get through this season, at least I can go into that transition with some cash on-hand.

I can't begin to say how much I have appreciated these thoughtful and genuinely helpful replies. Nothing was out of line, and I thank you very much. I wish I'd found this forum back in August rather than late November.

I just want to say thanks for all the thoughts you've taken the trouble to share. I tried to get more information today, but it was a different person who didn't know. As I typically begin my season mid-January, the clock has probably wound-down about as far as I dare.

I'd been in conversation with a trucking company near me, Online Transport, about a dedicated run, home daily, at Toyota, in Georgetown/Lexington, KY. That position requires 6-months OTR experience. They haul Lexus parts. I was more or less resigned to slog through another tax season (I own a tax prep office) with the intent of pursuing a traditional OTR path in May, when the recruiter I spoke with asked how far I was from another town.... five miles away. "Well, we do have a dedicated route there that might fit, once you get your CDL through our training." Apparently, this is hauling plastics in the KY/TN/IN area, home nightly or near-nightly, paid on an hourly basis. The hourly rate he mentioned would represent an annual compensation roughly double the average annual profit of my business, plus medical benefits.

Being away from my 15yr old daughter and sweet wife weeks at a time has been, easily, the greatest barrier to my thinking about this sharp turn in career choice.

I feel I would be a fool not to take this risk, as I am uncertain the chance would be there in May. Obviously, though, many old and contradictory adages come to mind. Things like, it's always greener on the other side... And, a bird in the hand is worth two in the bush... My wife, being a wiser and better woman than I have any right to expect, handed me her Bible today and said to read Proverbs 12. And I came across this: "Better to be a nobody and have a servant than to appear to be a somebody and have no food." I had to laugh, because that's how it feels right now. There's a certain pride in saying I own my business and have lived off my own labors and efforts and client-care for nine years....yet had to top off my credit card to get us through December/January.

I have agonized over this decision. Everything I've ever done in my life I've taken very seriously. I don't commit quickly, but once I do, I stick to it sometimes to a fault. In our family conversations on the matter, my daughter has laughed several times, observing, "And so the pendulum swings..." She and my wife are supportive no matter what I choose. They even gave me a very nice insulated coffee mug for Christmas to take on the road. I felt Monday that opening the office this season was the only intelligent choice. I've invested so much life into it, often way way outside my comfort zone. I genuinely care for my clients, most particularly for the score or so elderly shut-ins I make house-calls to. Everyone knows me as the tax guy, with all the unstated and probably untrue assumptions about my mental acuity. On the other hand, 1500 business-related phone calls a year has really worn this pretty intensely private person out. Monday night, I couldn't sleep, just heart pounding and crazed thoughts all night, to the extent I finally got up at 4 and sent Online the more detailed list of references they had requested. They've now emailed me and want to talk about setting up the training.

So here I am, planning to call either Online tomorrow morning to see how solid that offer is... or my tax software provider to purchase this year's $900 installment.

So my question is this: if I'm planning to take the driving plunge anyway (and thus would have to shut my office down next year for certain), is this an unusual enough opportunity that I'd be wise to jump on it now? Or are these sorts of dedicated, regional/local routes common enough that I am likely to come across another one if I wait? This one wasn't listed on their webpage, for instance.

Thanks again for any insights you might offer. Apologies again for over-sharing. I know at least a few of you have owned a business and might have an idea what's racing around in my head right now. And all of you have made pretty significant career turns to get where you are. So, yeah, give me something to be sleepless over tonight.

According to their website, there is no tuition. http://www.driveforonline.com/jobs/Training/

I'd love to hear updates, if you're so inclined.