I still remember my first appearance in a Cook County courtroom, briefcase in hand, heart pounding, tie slightly crooked. Law school taught me negligence and causation; the courtroom taught me that behind every “claim” is a person who didn’t ask for their life to be turned upside down.

That, in a nutshell, is what it means to be a personal injury lawyer in Chicago. It’s part advocate, part counselor, part investigator, and all heart. After four decades helping injured people and families throughout Illinois, here’s the truth about this work and why I still love it. (I’m Stephen D. Phillips, Managing Partner at Phillips Law Offices and past president of the Illinois Trial Lawyers Association.)

Phillips Law Offices

Personal Injury Attorney chicago
Personal Injury Attorney chicago

You’re meeting people on the hardest days of their lives

No one calls us because life is going well. They call after a crash, a fall, a surgical error, or the unthinkable: a wrongful death. Your job is to stabilize chaos, explain the law, protect their rights, and build a path forward.

In Illinois, that means understanding liability, comparative fault, insurance coverages (UM/UIM), and damages inside and out. The statutes give you tools; how you use them, early evidence preservation, smart medical documentation, expert selection, often decides the outcome.

The learning curve is steep and lifelong

Law school teaches doctrine. Practice teaches persuasion.

Early on, I learned a humbling lesson: being right isn’t enough, you have to prove it in a way jurors understand and trust. That requires fluency beyond the law: medicine (imaging, mechanism of injury), biomechanics, human factors, crash reconstruction, and the psychology of how people perceive pain and credibility.

Every deposition rewires how you prep the next one. Every mediation sharpens how you frame liability and damages. And every trial reminds you the best story still needs rock-solid facts.

Contingency practice: long hours, real risk, high stakes

Personal injury is mostly contingency work. You advance costs, carry cases for months or years, and you don’t get paid unless you win. That changes your mindset. You become meticulous about case selection, proactive with discovery, and relentless about preserving (not just finding) evidence, scene photos, EDR (“black box”) downloads, surveillance video, cell records, and treating physician testimony.

It is demanding. You’ll draft at midnight, wake up at 3 a.m. thinking about a cross-examination, and spend weekends prepping experts. But when you put a settlement check in a client’s hands that covers medical care, replaces lost income, and restores stability, it’s worth every mile.

The reward: making a real difference

One of the cases I’m proudest of involved a catastrophic trucking crash. Liability was denied for more than a year. We reconstructed the scene, subpoenaed telematics and maintenance data, worked with top experts, and tried the case. The jury returned a result that finally acknowledged the harm and secured the family’s future.

Verdicts and settlements don’t undo loss, but they do deliver accountability, medical security, and dignity. That’s justice, applied to real life.

Empathy and resilience: both are non-negotiable

You’ll feel your clients’ grief. You’ll also face defense tactics designed to minimize it. Social media “gotchas,” selective IME reports, delay and deny claims handling, you’ll see it all. Your job isn’t to be cynical; it’s to be prepared.

Empathy keeps you human. Resilience keeps you effective. The work asks for both, every single day.

Practical advice if you’re thinking about this career

  • Become evidence-driven. Photos, scene video, EDR data, medical imaging, wage documentation, collect early and aggressively.
  • Learn the medicine. Understand spinal injuries, TBI, pain management, and surgical indications. You’ll explain them to jurors for years.
  • Master negotiation, but prepare like you’re trying every case. The best settlements come when the other side believes your trial plan.
  • Guard your integrity. Jurors can sense authenticity. So can judges. Your credibility is your most valuable asset.
  • Remember the human being. Behind every exhibit sticker is a family figuring out tomorrow.

What keeps me fighting for injured people every day

For me, this isn’t just a job; it’s a calling. Every case is a chance to rebalance a life that got knocked off course by someone else’s choices. Some days will test you. Some will humble you. Many will remind you exactly why you became a lawyer in the first place: to help people when they need it most.

If you’ve been injured in Illinois, or you’re a young lawyer curious about this path, reach out to our Chicago personal injury lawyers at Phillips Law Offices. We represent clients across Chicago and throughout Illinois, and we’re always willing to talk, lawyer to lawyer, or lawyer to client.

About the Author

Stephen D. Phillips
Managing Partner, Phillips Law Offices – Chicago, IL

Stephen D. Phillips has spent more than 40 years representing injury victims and families in Illinois, securing record verdicts and settlements and serving as President of the Illinois Trial Lawyers Association. His practice spans catastrophic injury, trucking and auto crashes, medical malpractice, product liability, construction negligence, and wrongful death.

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