Sometimes you have to back up before you can move forward. In this chapter we need to do exactly that. So, let me back up a bit to set the stage…

Back in 2014, it took us the better part of our first year driving professionally, to realize that getting our things in storage and releasing ourselves from the monthly cost of a dwelling we rarely enjoyed, was the sensible thing to do.

We left home in San Diego, in late December, to attend CDL school in January, 2014. We went to orientation with Conway Truckload in February, started training in March/Apr and had the keys to our truck in the first week of May, 2014.

Were we to advise any couple going into professional team driving together now, we’d strongly suggest they do as much as possible to handle their housing matters, in advance of going over-the-road — which of course is outlined in my new book “Make A Million With Your Marriage” 

In our case, we didn’t put our things in storage and skip the month-to-month costs for housing until October, 2014.

At that time we had an Airstream, parked in San Diego, that had served as our home on wheels for the previous 10 years.

Our 1969 Airstream… home on wheels!

When we started down the team trucking road, our Airstream was ensconced in a wonderful little trailer park — think small, cute and right on San Diego Bay — we had an outdoor garden house with an additional small storage building loaded with a ton of tools and lots of extra items that wouldn’t be easy to move quickly. Nevertheless…

There was no point in spending $$ for living quarters we never saw.

During a relatively short home-time in October 2014 — less than 10 days — we had to break everything down, get packed up, separate out what went into storage in San Diego and get the rest to St Louis, along with our personal truck — a Chevy, Silverado, 3500, HD Dually — the Airstream and things we had to have access to.

This was a herculean job to complete in 10 days and move 1,800 miles across country… along with our Conway truck of course!

Had we done all of this before going OTR with Conway, it wouldn’t have been such a tight timeline.

Conway’s company policy for home-time amounted to ONE DAY OFF for every week on the road.

Thankfully, Conway had a great home-time policy because they allowed you to bank home-time days instead of losing them. If you didn’t use your home-time each week, you could save up the days to use whenever you wanted.

10 weeks on the road equaled 10 days of home-time. Days OFF that wouldn’t disappear like they do with so many companies out there — and — those days could be taken consecutively with no limit.

Say you had 30 days of home-time. You could take it all at once and not lose your truck assignment or standing in the company. 

Since we were home, at our place in San Diego, exactly 11 days in our first 8 months of team driving and used very little home-time anywhere else, we had enough time to get the job done.

Well… almost.

We did have to leave our truck and the Airstream sitting in Conway’s yard in Joplin, while we went back to work for a couples of months. Because it was inside a locked gate on Conway property, it wasn’t a worry.

Altogether, it took roughly three months to get everything handled with the move, the storage of personal items, the Airstream and our truck.

Because we chose to go into trucking in one fell swoop — starting with attending (and paying for) CDL School half-way across the country, then on to orientation, then into training and finally driving all back-to-back, we knew there would be a fairly long stretch of time with NO INCOME.

As it turned out for us that stretch lasted from late December 2013 to May, 2014.

That’s a pretty long NO INCOME window!

James and I would repeat to one another — and honestly — we did this every step of the way, on a daily basis — “failure is not an option, right?”

“Right! Not an option!”

And then we’d laugh. And then… we put our heads down and knew there was no stopping until we reached our goal.

After paying our bills through all of those “no income” months, paying for CDL school and having just enough to eat everyday… I will never forget what was left in our bank account on the day Conway handed us the keys to our first truck…

$65.73

It wasn’t empty! It was just… stretched. LOL

All we could afford to put on the truck the day we left to pick up our first load was beans and rice. We ate that every day until our first check came.

I had no idea there could be so many ways to prepare rice and beans!

I can tell you that there were a few times when it DID look like failure was imminent. 

As each challenge appeared — a miracle came (seemingly) out of nowhere.

The most amazing potential FAIL was right at the tail-end of CDL school when the MIssouri DMV refused to allow me to test for my license.

Here’s what happened…

At the end of the CDL training, the instructors would take groups of students to the DMV in the trucks — to do their driving and knowledge tests.

When I got there and stepped up to the window, I handed over my CDL permit to get my test kit. The kit has the maneuvers you’ll have to do and which DMV tester you’ll work with. 

So, the woman took my license, looked at it for a moment closely then walked away from the window.

I was ready! I couldn’t wait to get his done.

When the woman returned, she pushed my permit under the glass and across the counter and said flatly, “No. We can’t test you.”

“Pardon?” I asked in disbelief as I picked up my permit and glanced at it.

“You have a Class A license. We can’t test you.”

“What?” again in disbelief.

“I’m sorry that’s not a Permit License. You’ll have to go back to California, get your Permit and come back for the test. I can’t test you. You have a Class A license” she said again. 

Then she continued, “Ok, I need to move on”, she looked past me to the person standing behind me and waved them forward.

I stood there for a moment unable to move. I couldn’t believe we had come this far and they wouldn’t test me?? What were we going to do?

I went back to the truck where another student was waiting, climbed into the passenger seat and burst into tears.

When my fellow student asked what happened I just said, “they won’t test me.” He didn’t know what to say and neither did I.

I had gone to take the test before James, because he was in the next group to go to the DMV. Each group had the use  of the trucks from the school.

James was standing in the yard when we got back. He saw me climb out of the truck with tears running down my face and asked what happened. I told him what I was told and right then his group was leaving for the DMV. He had to go. He quickly said, “we’ll figure this out” kissed me on the cheek and took off for the truck.

As it turned out, the lady at the DMV was correct.

I didn’t have a “CDL Permit License”. California had made a mistake. The DMV sent a full Class A License that somehow got past everyone at the school for the last month — including me.

When James got back from his test, he had been disqualified and didn’t get his license either. The instructor was going to allow one more chance since it was a problem with the truck. He was scheduled for later in the afternoon.

In the meantime, James and I went into the school building, found an empty office we could use and closed the door so I could call the California DMV.

I explained the situation to the first person that answered — and to my amazement — I was put through to the head of the DMV for the State!

For several minutes I explained that I had — incorrectly — been sent a full Class A License when I was supposed to get a Permit. I went on to say this meant I had just gone through a month of CDL training at a school in Missouri and could NOT be tested by the Missouri DMV because I already had a Class A license! AND FURTHERMORE — this also meant I would have to go back to California to start this process from the very beginning and that was not in the realm of possibility — AND finally — I needed Mr. DMV (we’ll keep his name anonymous) to somehow make this right!

Once I was done, the head of the DMV for the State of California took a long pause.

James and I waited not knowing what to expect.

When the gentleman started to speak, it seemed like he lowered his voice a bit and maintained a very calm and impressive tone…

“Mrs. Steward, you’re right this should not have happened. (pause) If you don’t want your Class A license, you’re welcome to send it back. I will happily accept it. You can then return to California and begin again…..”

My heart dropped to somewhere in the vicinity of my ankles and I drew a breath. I looked at James who was listening closely and waiting…

The man continued, “…on the other hand Mrs. Steward, you have a Class A license. Would you like to keep it? Or return it? 

Do you understand?”

James and I stood with our heads together, listening to the speaker of my phone. We looked up at each other at the same time. The absurdity of the situation had just dawned on both of us.

I barely whispered — more like mouthed the words to James, “Did we just hear what the head of the DMV of the State of California, just said?”

James eyebrow shot up and a sideways grin appeared.

“Um…” I had to find my voice, “well sir, I think I do understand.”

“I’m glad” he said calmly. “Will that be all Mrs. Steward or can I do anything else for you?”

“Um, no sir.” I said, “Thank you so much” and he hung up. 

James and I hugged and I screamed just a little bit! All I had to do was get my diploma and run all of this past Conway. It would be up to them now.

And it didn’t end there…

The following week, we went to the Conway Orientation, in Joplin, Missouri. That’s when we learned that getting a “promise to hire letter” doesn’t mean you’re actually hired. You must pass every driving, backing and information test they have over the week of orientation — or you’re out.

AND… if you fail somewhere along the line, you cannot re-apply for 60 days.

We thought a “promise to hire letter” meant it was guaranteed.

Uhhh… nope.

Throughout that week in Joplin, James and I watched as seasoned drivers applying to drive for Conway along with us, failed tests one after the other.

Here we were — complete noobies who had never driven professionally — watching pros wash out and get sent home on the spot.

Were we going to pass a backing test when neither of us had backed a 53 foot trailer more than 4 or 5 times in a CDL class?

It still brings a smile to my lips when — in my mind’s eye — I see James do his backing test. He would move the truck a few feet, stop, climb out and go have a look. He would climb back in, move a few more feet, get out and have a look. This went on for awhile until the trailer was in the hole. It was comical. 

Many of the pro drivers in our orientation class seemed to think that getting out to look made them look stupid or that it was somehow unprofessional. 

I noticed that no one really looked stupid until they HIT something and got sent home!

NOT HITTING ANYTHING was the whole point of the test.

The instructor said over-and-over again to all of us, “get out and look as often as you want — just don’t hit anything. Got it?”

So, James and I got out and looked. A lot! Out of an orientation class of some 35 people we were two of the 6 drivers who got passed through to the training program!

The training program was 10,000 miles each with our respective trainers.

While James’ trainer was right there and ready to go… Conway didn’t allow women drivers to train with male trainers at that time. It had to be a woman. 

There were so few women willing or able to be trainers that I had to wait until a woman trainer could be found. And no one knew exactly when that would be.

So, I stayed at the hotel Conway had put us up in for the full orientation, which they paid for — by myself — while James went out with his trainer.

One week turned into two and I was still sitting in the hotel.

By the end of the second week — and still no trainer — it was starting to look like that NO INCOME stretch was getting stretch a bit too thin. If we weren’t able to pay our bills long enough to start earning — that could mean losing everything we had worked so hard for.

Trainees weren’t allowed to spend much time on the phone while training. That meant that James and I were only able to manage a few minutes on the phone, every other day. 

As we had done from the beginning, we reminded one another, “failure is not an option, right?”

“Right!”

None of us are promised that life will be easy and frankly — it’s not. Life is school and we’re here to learn whether we want to or not. 

That said, if one is willing to put in a bit of effort and leave the “how” alone, it’s nearly impossible to lose. 

I have come to understand that while I CAN decide on the “what” — I cannot figure out the “how” — and thankfully — it’s not my job.

James and I kept our eyes on the WHAT and not the HOW and it turned out to be everything we needed, every step of the way. 

At the end of week two in the hotel by myself, a woman trainer was finally found. 

I was excited to meet my trainer. As it turned out she wasn’t quite as excited to meet her first student. My newly minted female trainer was an excellent driver with an excellent record… as a solo driver. 

What my new trainer didn’t take into consideration when she took the opportunity to train someone was that she would have to be in the truck with another person… something she wasn’t good at doing. Seriously, this lady genuinely didn’t like people.

In fact…

…she didn’t like to be spoken to or touched. And here we were in a very small T660, which is one of the smallest Kenworth cabs out there. If I barely brushed against her she would come unglued. By day four it was getting pretty stressful for both of us.

My 10,000 mile training was just about halfway done when my trainer cracked. She suddenly decided she could not have anyone in her truck. 

Period.

Without warning and for no reason she could explain, I was kicked out of her truck — literally — and dropped off at one of Conway’s sister terminals, in South Texas. 

I was now several hundred miles from James and from Joplin, with my stuff on the ground and nowhere to stay or go. 

Conway called my phone literally moments after all of this happened. 

The head of Safety, sincerely and profusely apologized for my trainer’s behavior and assured me this would all get worked out  AND above all… this had nothing to do with me.

At that moment, it didn’t feel like it had nothing to do with me LOL! 

So, I gathered my things — which amounted to a fair amount of gear, including a jacket, a pillow, a sleeping bag, a bathroom bag and a small duffle with clothes and some basic cooking gear. Nothing fancy but definitely quite a bit to carry by yourself.

Conway arranged a bus ticket for me to get from South Texas, back to Joplin and the Texas terminal manager very kindly drove me to the nearest bus station where I lugged all my gear around until me and 1,400 other people got on the same bus! 

17 hours very tired hours later and I was back to Joplin and back in the hotel waiting once again for another woman trainer.

James was still on the road finishing his training program.

Woman Trainer #2 arrived within a couple of days. In the first  moments of meeting her — though she was definitely an interesting person — I was certain that she didn’t hate humans completely, so it was a go. 

I managed to get through the entire 10,000 mile training program with flying colors — a few bruises — but mostly flying colors!

James had an amazing trainer — a 35 year veteran driver named J.W., a man we still talk to now and again and who’s an excellent and patient teacher.  

Why did James hit the jackpot and I kind of… didn’t? It may be strange to say it but we both got what we needed and came out stronger and more determined.  

After a few weeks apart, James and I were reunited in Joplin when I was done with training — and all that was left was to find out if we would be hired… or not.

A day later we were asked to select a truck and were given the keys to our first truck — a beautiful Kenworth T680 — brand new — which I promptly dubbed “Bella”. If you go to YouTube and look up that name on the LovinTruckin channel, you’ll see her!

By the way, it’s true that we started out in our first company driving position with $65.73 in the bank — and then made over a million dollars in a little over 4 years of driving team. What’s possible? You tell me. 

I realize as I come to the end of this that it’s not even close to what I had planned to share with you this week. 

When I sat down to write — with my iPad propped on the steering wheel, as usual — it appears I wasn’t in charge of where my fingers wandered on the keyboard and I didn’t resist! 

Maybe this is for someone on this list who’s facing a difficult challenge and recounting our little story can show you that the basic act of not giving up can practically guarantee success. At the very least you’ll come out with the tools to do things you never imagined possible before! 

Over these last few years, which I will get into more next week (I promise), I’ve become quite literally an unreasonable human being. 

Being unreasonable regarding your dreams is good. It is a super-power to refuse to be reasonable or logical when it comes to seeing your dreams come true.  

Reasonable people quit when things get tough. Don’t be reasonable… be ridiculously unreasonable when it comes to your dreams and they will manifest in the real world. 

Honestly, I’d be thrilled to be the most unreasonable person you know!

Truthfully,
Andrea

P.S. The fastest way to ruin your life:
Do what others want for you.
Never question what you’re told.
Take the route that seems safe on the surface, but is the least safe of them all.
Avoid the essence of life – trial and error – and close yourself off to the profound, the deep, and the meaningful.
The greatest mistake of all is not making any mistakes.
This is the life of the masses.
– Dan Koe