The lost art of figuring shit out

Photo by Marvin Meyer on Unsplash

In the IT industry, critical thinking and troubleshooting skills are cornerstones of success. However, in recent years, I have observed a troubling erosion of these foundational capabilities.

While technological advancements promise efficiency and innovation, they also foster dependency and complacency inadvertently. For instance, automated systems and AI-driven tools often remove the need for manual problem-solving, encouraging users to rely on predefined solutions. This ease of use, while convenient, can stifle the development of deeper troubleshooting skills and critical thinking. As a result, when these systems fail or present unforeseen challenges, individuals cannot often resolve issues independently. The art of “figuring shit out” — the ingenuity and persistence that once defined IT problem-solving — is increasingly lost to automation, over-reliance on tools, and a lack of hands-on experience.

The historical baseline

Not so long ago, IT professionals were often self-taught pioneers who relied on curiosity and resourcefulness to navigate the uncharted waters of emerging technologies. Books, forums, and trial-and-error methods were the tools of the trade, fostering a hands-on approach to learning that built resilience and critical thinking. Unlike modern pre-packaged solutions, these methods require IT professionals to engage deeply with systems, troubleshoot creatively, and persist through challenges to uncover solutions. This culture of learning by doing fostered a deep understanding of systems and the ability to troubleshoot effectively. Breaking things — and then fixing them — was not just tolerated; it was encouraged.

Contrast this with today’s industry, where structured certifications and pre-packaged solutions dominate. While these innovations have undeniable benefits, they often leave professionals ill-equipped to tackle nuanced, real-world challenges. Memorizing a certification’s content does not guarantee the ability to think critically when systems fail in unexpected ways.

Dependency on tools

Modern IT environments are brimming with tools that promise to simplify work: AI-driven monitoring systems, automated deployment pipelines, and low-code platforms. While these tools undeniably save time, they can also create a dangerous dependency. It’s increasingly common to see IT professionals struggle when confronted with problems that fall outside the tool’s predefined capabilities.

For example, an engineer reliant on an automated monitoring tool may struggle to identify the root cause of a performance issue when the tool fails to provide actionable insights. The critical thinking required to dive into logs, analyze network traffic, or piece together disparate symptoms is at risk of becoming a lost skill. For instance, I once encountered a scenario where a critical network outage required correlating logs from multiple servers, analyzing packet flows, and identifying a subtle configuration error. Such a challenge demanded not just technical knowledge but also creativity and persistence — skills that are increasingly rare as reliance on automated tools grows.

Contrasting experiences: Xfinity customer care vs. early broadband troubleshooting

My recent experience dealing with Xfinity customer care exemplifies the erosion of critical thinking and problem-solving skills. When trying to move my elderly mother’s cable to a temporary address, I encountered customer service representatives who lacked both language proficiency and the ability to troubleshoot effectively. Everything they touched, they screwed up. Their reliance on scripts and superficial fixes only prolonged the problem, leaving me frustrated and without resolution until escalation became unavoidable. It wasn’t until an experienced tech came to my mom’s condo to fix her cable did things start to shake out.

This stands in stark contrast to my early days as a technical writer during the rise of cable broadband. Back then, addressing connectivity issues often meant rolling up our sleeves and diving into the nuts and bolts of network systems. We didn’t have pre-built playbooks or automated tools to lean on; instead, we relied on deep technical understanding, creative problem-solving, and collaboration. These experiences not only resolved the immediate issues but also enriched our skills and confidence in handling complex systems.

The difference between these two scenarios underscores the consequences of the modern “plug-and-play” mentality and a lack of emphasis on foundational skills. The art of troubleshooting has become a rare commodity, replaced by dependence on rigid processes and external escalation. This shift can have serious consequences for businesses and end-users alike. Without robust troubleshooting skills, organizations face prolonged downtime, increased costs, and frustrated customers when issues arise. End-users, in turn, are left navigating subpar service experiences, often enduring delays or incomplete resolutions due to the lack of expertise on the front lines.

The cost of experience

One of the most significant contributors to this decline is the diminishing value placed on hands-on experience. Entry-level professionals are often expected to hit the ground running with limited training, relying on pre-built templates and tools rather than developing a foundational understanding of systems. Organizations prioritize speed and cost-efficiency over nurturing talent, resulting in a workforce that may know “how” to do things but not “why.”

This gap in understanding is particularly stark in areas like cybersecurity, where attackers are constantly innovating. Professionals who lack critical thinking and troubleshooting skills are ill-equipped to respond to novel threats, leaving organizations at risk.

Reclaiming the lost art

The path forward requires a cultural shift within the IT industry. Organizations must prioritize critical thinking and troubleshooting as essential skills, equal in importance to technical certifications. This can be achieved by integrating these priorities into hiring and training practices. For example, hiring managers could include scenario-based questions during interviews to evaluate problem-solving abilities. Training programs should focus on hands-on workshops that replicate real-world challenges, ensuring that employees develop the skills to analyze and resolve complex issues effectively. This involves fostering environments where curiosity, experimentation, and learning from failure are encouraged. A few key strategies include:

1. Investing in training: Training programs should go beyond teaching how to use tools. They should emphasize understanding underlying principles, systems architecture, and problem-solving methodologies.
2. Encouraging hands-on practice: Simulated environments, hackathons, and “break-it-to-fix-it” exercises can help professionals develop the skills needed to troubleshoot effectively.
3. Mentorship programs: Pairing less experienced professionals with seasoned mentors can bridge the gap between theoretical knowledge and practical expertise.
4. Valuing experience: Organizations should recognize and reward the depth of knowledge gained through hands-on experience, not just certifications.
5. Promoting curiosity: A culture that values asking “why” and “what if” will inherently foster innovation and resilience.

Conclusion

The IT industry’s rapid evolution brings tremendous opportunities, but it also demands a reevaluation of the skills we prioritize. The art of “figuring shit out” isn’t just a nostalgic relic of the past; it is a critical competency for the future. By reclaiming and fostering this art, we can ensure that IT professionals are not just operators of technology but true innovators and problem solvers.

Will Kelly is a writer, marketer, and keen observer of the IT industry. Medium is home to his personal writing. He’s written for CIO, TechTarget, InfoWorld, and others. His career includes stints in technical writing, training, and marketing. Follow him on X: @willkelly.