This interview is with Cass Wennlund, Attorney at Wennlund & Associates.

Cass Wennlund, Attorney, Wennlund & Associates

Could you please tell us a bit about yourself and your journey to becoming a legal professional?

Certainly! Growing up in New Lenox, Illinois, I was always surrounded by a strong sense of community. My father, a respected figure in our town, taught me the importance of integrity, hard work, and service to others. I witnessed firsthand how local businesses and families sometimes struggled to navigate legal challenges, and it sparked a desire in me to make a difference.

I pursued my law degree at the University of Illinois Chicago School of Law, where I gained a strong foundation in understanding the law's complexities and its role in empowering individuals. After graduating, I began my career in a traditional legal setting, working hard to develop my skills and earn the trust of my clients. In 2009, I took over Wennlund & Associates, a firm originally founded by my father in 1979. This allowed me to honor his legacy while shaping the firm into one that focuses not just on solving legal issues but on serving the broader community.

Throughout my journey, I’ve been drawn to areas like civil litigation, real estate, zoning and land use, and business law. These fields give me the opportunity to help people protect their families, businesses, and livelihoods. Along the way, I’ve also taken on roles like Township Supervisor, which has deepened my understanding of the community’s needs and reinforced my commitment to public service.

For me, becoming a legal professional has always been about more than just practicing law—it’s about using it as a tool to support, guide, and empower the people and communities I care about.

What key experiences in your career have shaped your perspective on the field of law?

Over the course of my career, several key experiences have shaped how I view the field of law and my role within it. Early on, I worked on a case involving a small family-owned business that was facing an unjust property dispute due to misinterpreted zoning laws. The stakes were high—their livelihood was on the line. That case taught me how critical it is for attorneys to understand not just the law, but the real-life impact it has on people. Seeing the relief and gratitude from that family after we won the case reaffirmed my belief that law is about more than statutes and procedures—it’s about protecting people’s futures.

Serving as the New Lenox Township Supervisor has also been pivotal. It gave me a firsthand look at the challenges communities face, from zoning and land-use conflicts to ensuring transparency in governance. This role helped me see the intersection between law, leadership, and community development. It’s where I learned that legal professionals have a responsibility beyond the courtroom—to use our expertise to strengthen and guide the communities we serve. Another defining experience has been mentoring young lawyers and law students. I’ve seen how complex and demanding this field can be, and I’ve come to value the importance of fostering a culture of integrity and empathy.

By helping the next generation navigate the profession, I’m reminded of the lasting impact we can have—not just on cases, but on people’s lives. Each of these experiences has shaped my belief that the law, at its core, is a tool for service. Whether I’m advocating for a client, guiding a team, or contributing to my community, my perspective remains the same: success in this field comes from balancing technical expertise with a deep understanding of the human element behind every legal matter.

Can you share an instance where you had to navigate a particularly complex legal issue, and what practical advice did this experience teach you?

Certainly, there have been many moments in my career where I’ve had to tackle complex legal issues, but one instance stands out. I worked with a client who was dealing with a multi-faceted dispute involving property rights, business interests, and conflicting regulations. The case was particularly challenging because it required navigating intricate zoning laws while also balancing the emotional and financial stakes for the client.

On one hand, the law itself was clear in certain areas; on the other, the real-world implications created gray areas that demanded creative problem-solving. This experience taught me a few valuable lessons. First, the importance of stepping back and looking at the bigger picture. In law, it’s easy to get bogged down in the details, but finding the best solution often requires understanding all sides of the issue and how they connect. Second, communication is everything. Keeping the client informed and managing their expectations, while also collaborating with other parties to reach common ground, was critical to resolving the matter. Legal professionals sometimes underestimate how much trust and clarity can move the needle, especially in emotionally charged situations.

I learned that persistence and preparation go hand in hand. You can’t rush a complex case—every angle needs to be considered, every option explored. It’s about balancing patience with proactive steps. For any lawyer facing a difficult issue, my advice would be this: stay calm, lean into your expertise, and remember that the best outcomes often come from collaboration, diligence, and keeping the client’s best interests front and center.

Many aspiring legal professionals are drawn to the intellectual rigor of the field. What advice would you give them based on your own experience in tackling intellectually stimulating cases?

For aspiring legal professionals drawn to the intellectual rigor of the field, my advice would be to embrace the challenges but remain grounded in the human side of the work. Intellectually stimulating cases can test your skills, push your limits, and provide tremendous opportunities for growth. However, it’s important to remember that the law is not just about solving abstract puzzles—it’s about solving real problems for real people.

When tackling complex cases, preparation is everything. Immerse yourself in the details, understand the law inside and out, and anticipate counter-arguments. Some of the most rewarding cases in my career have required me to dig deep, think creatively, and approach problems from multiple angles. The key is to develop a disciplined mindset: stay organized, ask questions, and never stop learning. The law is constantly evolving, and the ability to adapt and think critically will set you apart.

That said, don’t let the intellectual side of the work overshadow the client’s needs. Every case, no matter how complicated, involves people—individuals, businesses, or communities—who rely on you for guidance and advocacy. Approach your work with empathy and humility. Listen carefully, communicate clearly, and always consider the bigger picture.

Don’t be afraid to collaborate. Some of the best ideas and solutions come from working with mentors, colleagues, and experts who offer fresh perspectives. Tackling challenging legal issues is rarely a solo effort, and the ability to work as part of a team is just as important as individual brilliance.

In the end, the intellectual rigor of law is incredibly rewarding, but its true purpose is to serve others. Keep that balance in mind, and you’ll find success, growth, and meaning in your career.

LegalConsultant.io aims to be a resource for those seeking legal knowledge. What are some common misconceptions people have about the law, based on your experience interacting with clients or the public?

One of the most common misconceptions I’ve encountered is that the law is black-and-white. Many people assume that legal issues have simple, straightforward answers, but in reality, the law is far more nuanced. Every case comes with its unique circumstances, and even seemingly clear-cut situations can involve layers of interpretation, negotiation, and precedent. Clients are often surprised to learn that outcomes can vary based on subtle differences in facts or how arguments are presented. Another misconception is that going to court is the only—or best—solution for legal problems.

Many people see litigation as the primary path to resolution, often fueled by portrayals in movies or TV shows. In truth, most disputes can be resolved through alternative means like mediation, negotiation, or settlement discussions. These approaches are often faster, more cost-effective, and less stressful for everyone involved. I also find that clients sometimes believe legal representation is unnecessary, particularly when dealing with contracts, real estate, or family matters. People assume they can handle things on their own with forms or online resources, but what they often miss are the risks of overlooking critical details.

A small oversight in language or process can lead to significant consequences down the road. Legal professionals exist to provide clarity and protection in ways that DIY solutions simply can’t. There’s a misconception that lawyers are solely focused on “winning” or making money. In reality, many of us are driven by a deep commitment to service, advocacy, and helping people navigate some of life’s toughest moments. For me, the law is not about competition—it’s about finding solutions, empowering clients, and ensuring fairness.

Ultimately, the law is complex, and while it can seem intimidating, it’s there to protect and serve people. My goal as an attorney has always been to demystify the process, provide guidance, and help clients understand how the law can work for them, not against them.

The legal landscape is constantly evolving. How do you stay updated on the latest legal developments and ensure your knowledge remains current and relevant?

Staying current in the legal field requires a commitment to continuous learning. I regularly attend legal seminars, webinars, and professional conferences to stay informed about changes in laws and emerging trends. Subscribing to legal journals and resources, like Law360 and updates from the A.B.A., helps me track important developments.

I also engage with peers through bar associations and professional networks, where we exchange insights and best practices. Technology plays a big role as well—tools like Westlaw and LexisNexis make it easier to stay up-to-date. For me, staying relevant means embracing change and maintaining a mindset of lifelong learning.

Technology is increasingly impacting the legal profession. Can you share an example of how you've leveraged technology in your work, and any advice for others looking to do the same?

Technology has been a game-changer in my practice. Tools like case-management software streamline workflows, helping us manage documents, deadlines, and client communication efficiently. For example, cloud-based platforms allow secure access to files, improving collaboration within the team and with clients. I’ve also embraced virtual meetings to enhance accessibility.

My advice: start with tools that solve immediate challenges, ensure data security, and commit to ongoing learning. Technology should complement your work, not replace the personal relationships that define great legal service.

What are some ethical considerations that you believe are paramount for legal professionals in today's world?

Ethical integrity is essential for legal professionals. Transparency with clients, maintaining confidentiality, and avoiding conflicts of interest are paramount. In today’s world, upholding honesty, even when it’s difficult, builds trust and credibility. With technology and AI playing a larger role, we must also ensure data privacy and ethical use of digital tools. Ultimately, our duty is to serve justice while prioritizing fairness and accountability.

Looking ahead, what emerging trends in law are you most interested in, and why do you think they are significant for the future of the legal profession?

I’m particularly interested in the evolution of environmental law and data privacy regulations. As communities face increasing challenges with sustainability and protecting personal information, these areas are becoming more significant.

Additionally, virtual courtrooms and digital tools are changing how we practice law, improving accessibility for clients. These trends highlight the need for lawyers to adapt while ensuring we continue to uphold ethical standards and serve our communities effectively.

Thanks for sharing your knowledge and expertise. Is there anything else you'd like to add?

Thank you for the opportunity. I’d just add that the law is not just about cases and courtrooms—it’s about people. Staying grounded, leading with integrity, and always striving to serve the community are what make this work truly meaningful.