The Freeway’s Ghost: A Pragmatist’s Reckoning with the Remote Work Revolution
For years, California freeways told the story of the American workweek. Monday mornings meant the grind was beginning, and Friday afternoons signaled the great escape. From my office, I had a direct view of the freeway leading through the Central Valley of California to the Sierras and, ultimately, Lake Tahoe. Every Friday after one o’clock in the afternoon, that highway transformed into a parking lot—especially in the summer and winter—as folks fled the Bay Area for the Sierras to go camping or skiing. It was clockwork. That traffic surge usually thinned out when school let out around June 14, only to roar back when the school year resumed in August.
That old rhythm is now a ghost. The heaviest traffic these days is on Tuesday mornings and Thursday afternoons. The change isn’t just a logistical change. It’s a reflection of a more profound cultural reckoning. It’s no longer just about when and where people work—it’s about what work is and what it means. We are in the middle of a cultural struggle: generations seeing the world of work through very different lenses and leadership finding itself at odds with proven performance. I’ll admit it—my view has shifted, and dramatically so.
I come from a generation—and a profession—where sitting next to someone was how you learned the ropes. As a former VP of Claims and Risk Manager, I believed, to my core, that you couldn’t correctly train a claims examiner unless they were physically in the room with their supervisor. I was confident that the nuance, the judgment, and the understanding of complex jurisdictional rules couldn’t be transferred over Zoom or a screen share. I was so convinced that if you had told me that this transition was the only option, I would have told you that you might as well just put a gun to my head and pull the trigger. Remote training would not work!
Then came the pandemic and, with it, a forced experiment.
As a board member of a large insurance company, I had the opportunity to witness remote training in action. To my surprise—and, frankly, my delight—it was a resounding success—not just adequate but impressive. This success was not a stroke of luck but a result of the hard work of frontline supervisors and the thoughtful use of technology—cybersecurity, claims systems, and reliable internet access.
I watched supervisors open Zoom meetings each morning with their teams and stay actively available throughout the day. When new hires had questions, they received instant feedback. The supervisor could pull up the exact document, share their screen, walk through the file, and explain the nuance as if they were sitting shoulder to shoulder.
New hires got up to speed. Their productivity matched—and in many cases exceeded—that of those trained the old-fashioned way. Virtual mentorship worked. Structured learning worked. Digital tools worked. It was humbling. I ultimately had to reconsider what I thought was possible.
The traffic pattern may have changed, but so has the battlefield. This is a culture war between those who believe work is defined by presence and those who think outcomes define it. Senior leadership, many of whom came up in an era when the office was the only arena for influence and effectiveness, remains fixated on the idea that presence equals productivity. They speak of collaboration, mentoring, and culture.
However, younger generations—Gen X, Millennials, and Gen Z—view work differently. They see the two hours spent commuting as time they’ll never get back. They see gas, tolls, lunches, and professional wardrobes not as investments but as unnecessary expenses. It’s not uncommon for workers to spend $30 to $50 daily to show up at a desk where they’ve already proven they can deliver results from home.
This isn’t about resistance to authority or laziness but a revaluation of priorities. And the truth is, many of them are correct. We’ve seen that they can meet deadlines, hit goals, and drive results without stepping foot in the office. In many cases, they’re more engaged and less burned out when they do.
I talked to a worker who was incensed that she was being forced back to work even though her company had been very productive and extremely successful during the pandemic (when the entire workforce worked remotely).
I guarantee she will jump at the first chance to work remotely.
There’s also real money on the line. In a complex world like workers’ compensation, where experience, judgment, and institutional memory are everything, forcing relocation or return-to-office mandates risk of losing high-performing talent. For insurance companies or self-insured companies with millions in annual workers’ compensation losses, even a modest 5% drop in efficiency translates to millions in additional exposure. In my experience, every time a claim is transferred from one examiner to another, the disruption leads to an additional five to ten percent in claim costs. This increase comes from delays in decision-making, loss of contextual knowledge, and the time it takes for the new examiner to get up to speed on the case’s history and nuances. Requiring remote examiners who deliver strong results to return to the office will inevitably result in turnover. This kind of disruption affects team stability and triggers a ripple effect in claim handling quality. When experienced examiners leave, claims often must be reassigned to new, less familiar staff. In my experience, every time a claim is transferred from one examiner to another, it leads to an additional five to ten percent in claim costs. This increase stems from delays in decision-making, the loss of contextual understanding, and the ramp-up time needed for the new examiner to comprehend the claim’s history and nuances fully. These are not hypothetical costs—they are measurable, material, and repeated. The cost of replacing seasoned professionals and absorbing the inefficiencies of turnover only compounds these losses. The disruption leads to an additional five to ten percent in claim costs. This increase comes from delays in decision-making, loss of contextual knowledge, and the time it takes for the new examiner to get up to speed on the case’s history and nuances, which is not theoretical. That’s real money. And let’s be honest—this isn’t about plumbers, retail workers, or paramedics. This conversation focused on roles that can, and demonstrably do, function remotely.
Those organizations that figure this out and choose flexibility over rigidity are winning. Not because it’s trendy or generous but because it’s an innovative business strategy. They will access better talent, foster loyalty, keep their experienced people, and attract new ones who want a say in their lives and work.
Culture is no longer something bound to a building. It’s shared values, shared purpose, and shared accountability. Excellent management has to learn how to create a corporate culture remotely. The best results I’ve seen didn’t happen because someone was in a cubicle—they happened because the right person had the freedom to focus and the trust to deliver. We’re also not in the same technical environment anymore. With AI and automation shifting what desk jobs even look like, the idea of requiring butts in seats for the sake of appearances is becoming absurd. If the machine handles repeatable tasks, we need the human brain to focus on what only humans can do. And that doesn’t require a badge swipe to happen.
The old commute patterns are gone, and they’re not coming back. The workforce is evolving, and leadership must evolve with it. I’ve had to confront my biases and beliefs and let go of traditions that no longer serve today’s workplace. What matters now is not who’s in the office but who is getting the work done, managing the risk, and delivering the outcomes.
This isn’t about ideology. It’s about pragmatism. It’s about performance. It’s about who we want to be as employers—and what kind of people we want to attract and retain. Flexibility isn’t a luxury or a perk anymore. It’s a necessity. It’s a strategy. It’s a mindset.
Senior management will likely win many frontline battles over returning to the office. They’ll make their case with tradition, control, and perception. But they will eventually lose the broader war. Because the best talent—those with the skills, knowledge, and drive—are quietly, consistently choosing better lifestyles. They seek companies that trust them, understand the value of their time, and recognize results over rituals. This shift won’t happen all at once. It will unfold in pockets—industry by industry, region by region. But the direction is clear. The future belongs to the organizations that adapt rather than dig in.
Those who embrace it will be the ones who lead the next generation of work—not from behind a desk but from a position of clarity and foresight.
Could not agree more!