The work-life balancing act as an owner: With rates down, focus on family, customer relationships to tip scales

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Updated Sep 6, 2023
Jason and Zane Cowan of Silver Creek Transportation and Innovative Logistics Group's Adam Wingfield
Silver Creek Transportation founder Jason Cowan (left, pictured with his son, Zane, the fleet's maintenance manager) and Innovative Logistics Group's Adam Wingfield spoke to building work-life balance as an owner-operator or small fleet owner in this wide-ranging talk Tuesday.

When Adam Wingfield's youngest daughter was born, he had a load of shingles on his truck in Missouri and was heading back east near his home base in the Carolinas. 

"I'll never forget," he said, "as I was coming back I was probably about two hours out when I got the call that she was about to be here."

But once he got to the hospital and called his dispatcher to tell him the good news, "even though he said, 'Hey, congratulations,' you know, the next phrase is? 'By the way, what time [are you] going to get those shingles delivered on Monday morning?'"

The former company driver turned owner-operator turned small fleet owner and now founder of trucking consultancy Innovative Logistics Group said the experience "shook me to the core."

Wingfield loves trucking, even the mundane parts. "There's nothing like coming out of your bunk and smelling the diesel fuel at a TA truck stop ... on a Tuesday morning," he said during Overdrive's recent talk with him, focused on giving an honest look at prospects for work-life balance as an OTR owner-operator. But Wingfield values his family, his health, and (even more) his stability. He urges owners to take steps to reckon with what his trainer told him early on -- "you're going to visit home," but "you're going to live on the road." 

Wrestling with that central tension of the reality of trucking, the pressure to run miles versus the need to lead a fulfilling, healthy life, pushed Wingfield to develop some of his best business strategies. In part, it's what took him from company driver to truck ownership, to fleet ownership, to a mission to support other owners through Innovative Logistics Group. 

Catch the replay: ‘Work-life balance’ as an owner-operator, small fleet owner


More are looking for that elusive goal of work-life balance with healthy profits and maximum time efficiency on the road to justify time spent on other pursuits. It's achievable, even in a down market like the current state of freight. In this webinar — sponsored by Bestpass — two men who’ve been in those shoes in a variety of roles presented strategies toward gauging and achieving balance to improve quality of life for yourself and/or your operators, whether you’re a one-truck owner leased to a carrier or with authority, or a small fleet owner hoping to deliver better balance to drivers and, ultimately, to yourself. Sit in on the wide-ranging discussion on-demand by registering.

Also part of the panel, which you can view in full on-demand via this link, Jason Cowan, Overdrive's 2021 Small Fleet Champ and owner of Henderson, Kentucky-based Silver Creek Transportation, stressed that Wingfield isn't alone. In fact, he noted, the younger generations rising up behind him in trucking tend to prioritize work-life balance much more than those past. 2022 data from owner-operator business services firm ATBS bears that thesis out in some ways, with the ongoing annual decline in miles run. Even as current rates and cost pressures rose throughout the year just passed, owner-operator clients of the firm on average still ran fewer miles

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"I think in this industry, sometimes in the past we thought, it's a badge of honor," Cowan said of a drive to push oneself to the limit over-the-road. "How much have you stayed away from home? And how long have I been gone?" he offered as hypothetical questions in a game of driver-to-driver one-upmanship. 

But home life doesn't have to be the enemy of trucking life, Cowan said, noting he finds that drivers employed at Silver Creek who have solid relationships at home tend to be the best among his core group of operators of the company's around 30 power units, with several owner-operators leased on among them.

Independents, 'own your backyard'

For Adam Wingfield, home and the road can be powerful allies if you "own your backyard" as a small business owner-operator, as he put it. 

He urged independents in particular to improve home time prospects by putting in effort to secure direct freight out of your region. It will keep you from doomscrolling, so to speak, all those increasingly dire posts of $1.50/mile freight on load boards, too.

Work the phones with manufacturers and other shippers within your "green mile," as he called it. "You've got to pursue direct contacts with shippers that load out of your area," he said, likewise the end of those runs. "If you look at your address, or wherever" you set the brakes and say, "'Hey, this is where I'm going to lay my head.' You need to a zip code search. Search and search manufacturers, distributors and [other] shippers."

[Related: The spot market is 'not where you need to live': On building business with authority]

He challenged owner-ops to "be honest with yourself" about this next part. "Do [the local shippers] know who you are? And do they know what you do? Have you established a relationship with them? Because, if not, then you're leaving some opportunities out there on the table."

Work the phones and make the visits, sure, but work-life balance isn't just about working hard now for some theoretical family time later. Involve the family now, he said. 

Bestpass logoThe May 23 webinar even was sponsored by Bestpass, the well-known provider of toll collections options as well as a myriad of other services. Find more about the company via its website.Coach your kids or spouse to help with all that Google searching, the asking around town. Introduce yourself to local shippers and tell them about your operation. The first call like as not won't result in business, he said, but you'll get on their radar. He likened it to having the restraint not to propose marriage on a first date.

Focus on those direct local relationships, and relationships with brokers to fill in your return trips when needed. Wingfield is acutely aware of the current fraud issues in brokered-freight markets and longstanding nonpayment issues as well, but he stressed "there is good" as well as bad at every level and station in trucking. The good are out there, and it's your job to know them.  

[Related'Fraud epidemic': Congress gets earful on double brokering, speed limiters]   

All of it -- selling to potential customers, managing relationships, sussing out quality middlemen as partners -- requires a heavy set of soft skills, something small fleet owner Cowan emphasized. "It doesn't matter if we're talking about trucking, if we're talking about the car business, or no matter what business we're in: Ultimately, we're in the people business." 

Frankly, that's the problem for many drivers.

"Being out there on a load, out there on a road all the time, 70 hours a week behind a wheel," Cowan said. "That takes a lot out of your interpersonal skills and puts them on the back burner. So a lot of times, our people skills are not where they need to be." (We did say this would be honest and unvarnished, right?)

Plenty in Overdrive's audience it's certain are thinking right now of a local shipper or two worth checking in with -- make the call. The apprehension some feel about the practice Wingfield attributed to a negative current that runs throughout trucking: "If you listen to what most people are saying, then you become most people, and if 'most people can't get direct freight,' then you become the most people that can't get direct freight."  

Don't be like 'most people' -- build family, trucking relationships

Cowan and Wingfield, as well as many other top performers among small fleets and owner-operators Overdrive has covered over the decades, stress how important relationships are. Family life actually requires very similar relationship maintenance and nurturing. It makes sense to tackle both in one go. 

Exercise those relationships, get that interpersonal skill practice time in with Facetime, phone calls, social media and basically any way that technology can connect you to the people you love, said Wingfield. Rather than just making a call when things get rough, actually plan relaxing and revitalizing activities, he suggested. 

"Make sure that when you do your planning -- your 34-hour reset -- you do just that," he said. "You plan it, don't just end up somewhere. And if you do, make sure that you have some alternative and some options get away from the truck stop! Y'all, get away from the truck, period. It's good for yourself to give yourself a little break."  

Healthy food options don't always abound at truck stops, so find a way to get away, he stressed. 

Use family connections and experiences to boost your mental health, use people skills to build business connections that will allow you to reject loads that won't take you home -- all will inject, Wingfield noted, some "planning predictability to where you can actually have that, that frequent home time and be able to have better family, community connection." 

Cowan hammered those points, noting that from the fleet owner's vantage "the very last thing we want is spouses to be fighting while they're in my truck going down the road." 

Silver Creek, he said, puts in intensive work with drivers about home time expectations and what they want out of their careers. "The killer of relationships is unmet expectations," said Cowan. 

adam wingfield, jason cowanMost drivers probably don't need a reminder of the faces on children or spouses when a birthday or football game gets missed, Wingfield and Cowan both stressed. This stuff weighs heavily and should be taken seriously.

Unmet expectations also dent business relationships. When making those calls within the green mile, as Wingfield has it, be careful not to overcommit. Cowan says owners can "tend to go into saying, 'Oh, we can do whatever you need us to do.'" 

The shipper may "need a truck every day," he noted, but then they "don't define exactly what they mean by that," he said. This, invariably, will lead to unmet expectations at some point. That's why Cowan likes to "over-communicate" on what he can do, rather than just assume both parties understand. 

To the seasoned owner-op, all this may sound familiar, boring even. Of course you should focus on mental health, eat healthier, work out, make time for the kids, be pleasant in person and on the phone -- all while doing a damned hard job and worrying about making ends meet. Surely these simple actions are a silver bullet for your personal and business problems, if only you had the discipline. ... We've all heard it before, and it can be a punishing thought that you're falling short. 

But all of these suggestions do have one thing in common: They're firmly in your control. 

"We get all riled up about things we can’t control, we can talk about rates all day long but it's not going to move the needle," said Wingfield. "I can control where I select my fuel and control the pressure on my right pedal." 

Wingfield is something of a stickler when it comes to fuel mileage, stressing common wisdom that even what seems like a small gain in mpg can save an owner upwards of $10,000 in a year.

This laser focus on controlling what you can, and forgiving and forgetting what you can't, puts drivers in "a position of power," said Cowan. 

Cowan, who offers educational courses to his drivers and employees, said to learn how to read a balance sheet and drill down into costs per mile. 

"Then I have the tools to say I either can or can't run this load, and I make the decision from a place of power," he said. "I'm not just guessing" if he can run a certain load at, say, $1.50/mile. Instead, he can know for sure his end and then weigh that against business, even interpersonal questions. 

"Do I want to do it to keep the customer? I can decide." he said. "Because what you don't know, you don't know."

Hear an audio-only version of the one-hour talk via the player below, or subscribe to the Overdrive Radio podcast via Apple and Google podcasts, SpotifyTuneIn, most anywhere you listen..