Let's Copy Them: What the Trucking Industry Just Taught Everyone

Last week, the federal government created a fix to a labor shortage without creating anything new. The Freedom Haulers initiative went into effect last week by the Department of Transportation, as they partnered with the Department of Labor, Veterans Affairs, and the Department of War. This program creates an easier pipeline for veterans into commercial trucking. According to the American Trucking Associations, the trucking industry is short roughly 82,000 drivers. Set aside the politics surrounding the announcement, because the mechanics are what matter, and the mechanism is really straightforward. Let’s take four things that already existed and connect them: 1. Credential translation. Veterans with military heavy-vehicle experience skip redundant CDL road testing. Basically, if you drove a big truck in the military, it’s now easier and takes less time to be able to drive big trucks as a civilian. 2. Re-emphasizing existing funding. Truck-driving schools are already GI Bill and VR&E eligible. The VA simply increased outreach to roughly 19 million veterans. 3. Pre-separation pipeline. The Department of Labor's Employment Navigator now connects transitioning service members directly with trucking employers before they leave uniform. Essentially Skillbridge’s main intent now with more marketing 4. Industry commitment. Werner Enterprises publicly pledged 1,400 veteran and veteran-spouse hires, giving the whole program credibility through a clear hiring target. That's the whole equation: Experience translation + utilizing existing benefits + clear pipeline + industry commitment = veterans hired. Let’s take a look at insurance now. The Industry With a Bigger Gap and (Potentially) Better Parts I’ve only been in insurance for two years. I heard on my first day, and many times between then and now, how little talent comes into the industry and how many boomers are about to leave it. An article from the Jonus group says that half of the current workforce is expected to retire over the next 15 years, leaving more than 400,000 positions unfilled. Our 55-and-over cohort has grown 74% in the last decade. The incoming side is worse: only 4% of millennials say they're considering insurance careers. So both things that I’ve heard from producers and insurers in casual conversation is backed up by the studies…but we’re basically ignoring it… I like to use proxies for everything. On the negative side, the accounting industry is an example of what could happen to our industry if we continue to admire our problem instead of solving it. The accounting and auditing workforce has shrunk by more than 17% since 2020, with over 300,000 professionals gone. First-time CPA exam candidates fell 33% between 2016 and 2021, and the math for their labor equation is similar to how the insurance industry’s is trending: roughly 124,000 annual openings against about 55,000 graduates. That kind of deficit is an obvious problem, as more than 720 public companies have cited insufficient accounting staff as a risk factor for reporting errors, up 30% from 2019. Insurance, especially the specialty side, is much different than accounting is, but at a certain point, we won’t be able to fight the consequences of this deficit internally. And while the impacts of accounting errors have huge implications, the impact of improperly written coverage due to an overworked, understaffed underwriting division could be just as damaging to their clients if not more. On the military side, the Aviation industry proved that a military pipeline could staff an entire skilled industry, until it’s not maintained. Before 2001, about 70% of U.S. airline pilots came from the military. That share of new hires has fallen to roughly 30%, and regional carriers have parked aircraft for lack of pilots. I believe this is turning around in the last few years, but it’s another reason to keep veterans at the forefront of your labor solutions. Wholesale Will Feel the Labor Shortage More Within insurance, excess and surplus lines could potentially take the hardest hit. Premium has more than tripled in a decade. Headcount has not. The workforce that places this business (insurance agencies and brokerages, roughly one million workers) is projected by BLS to grow just 4.7% over the next ten years. It wasn’t new talent that benefited from the last ten years either. The E&S boom was absorbed by more premium per broker, handled by increasingly senior people. Specialty expertise takes years to build, and that expertise is on the cusp of mass retirement. So now our wholesale industry has a double-edged sword of labor problems: talent isn’t coming in + E&S expertise takes time. Veteran Labor Supply Exists Perpetually. Roughly 200,000 service members transition to civilian life every year, and they're not taken advantage of correctly. Here are a few simple facts: - 42% of transitioning service members leave their first civilian job within a year; 80% within two. They cite poor cultural fit and lack of identity within the company as the main reasons. - Nearly one-third of veteran job seekers are underemployed, a rate 15.6% higher than non-veterans. Penn State's research puts a mechanism and a price on it: employers struggle to translate military skills — particularly leadership — and underemployed veterans dissatisfied with compensation earn $11,000 to $24,000 less than their peers three years out. So we can use these facts to create a rubric for hiring vets and keeping them: 1. Identify how their work translates 2. Understand what kind of worker they are: individual contributor (Broker, Agent, production side), deeply technical (Actuarial, claims, underwriting pricing) or leadership/management (operations, product, and many others). 3. Create clear metrics by which they will be promoted, awarded, or recognized in some way. They don’t need to feel special, but they do need a deliberately designed track. 4. Communicate what their future will look like on their current track 5. Consistently give them feedback. If this is a mentor program, great. If it’s the organization bought in as a whole on their vets’ success, even better. **Biggest thing to avoid: hiring them for their potential, but then keeping them in a role that has no path towards recognizing that potential.** What is most military experience? It’s risk assessment under uncertainty, operating within clear authority frameworks, complex-problem analysis and decision-making, leading teams under pressure. Trucking gets a veteran's easily transferrable hard skill. Insurance can get the intangibles. Freedom Haulers Parallel: Put the Freedom Haulers rubric against insurance and everything exists for our industry as well: GI Bill and VR&E already fund licensing exam preparation and professional designations eligible today. SkillBridge already exists; carrier participation is thin and wholesale participation is effectively zero. Producer licensing streamlining is the Commercial Driver’s License waiver parallel, specifically the pre-licensing courses, with the licensing exams retained. The industry commitment costs nothing to the initial group of companies other than an estimated hiring number and an article on LinkedIn. It’s not a perfect parallel because I’m equating a hard skill in truck driving with a more nuanced and interpretive set of soft skills. But pre-sorting personality types with their service records can make the interpretation more accurate, and this is an industry that needs veterans learning how to lead some of the most important companies in America. Trucking created its veteran pipeline in a single announcement. We need to stop admiring our coming labor shortage and start creating similar programs to combat it now. - Author: Nourse Fox, 8.7.26 Sources: U.S. Department of Transportation "Freedom Haulers" announcement (July 30, 2026); U.S. Bureau of Labor Statistics; AM Best Market Segment Reports (2024, 2025); NAIC; WSIA stamping office reports; ZipRecruiter/Call of Duty Endowment veteran employment study; Penn State Clearinghouse for Military Family Readiness; Syracuse University Institute for Veterans and Military Families; First Advantage/MilitaryConnected.org. All statistics linked inline.