It’s hard to believe it’s been 31 years since I first walked into Chicago-Kent College of Law on West Adams Street. I was 22 years old—young, green, and honestly, a bit clueless. I didn’t have a grand plan or lifelong dream of becoming a lawyer. I only applied to law school because one of my college roommates told me it was his plan and that you could do a lot with a law degree. That, and the fact that going to school meant I could delay entering the real working world for a few more years. Looking back, that kind of thinking definitely came from a place of privilege.
Of course, back in the early ’90s, law school tuition wasn’t nearly as crushing, and I managed to get by thanks to a combination of savings and part-time work as a law clerk and bartender. Things are a lot different now—economically, socially, and especially in terms of the law school experience itself. Technology and COVID-19 have completely changed the game. Kent marketed itself back then as the technology law school, but we still had to learn to research in actual books. I can’t imagine any school does it that way now.
Still, after three decades in and around the legal profession, I’ve learned a few things I wish I had known when I started. So, here’s my honest advice for anyone just beginning their legal education, especially the incoming Class of 2028.
The first year of law school is intense, but it’s often more about the mind games than the actual material. You’ll hear that classic line, “Look to your left, look to your right; one of you won’t be here by graduation.” It’s meant to scare you, and in some cases, it does. People overcompensate by showing off how much they’re reading, outlining, or stressing out.
But here’s the truth: most people who leave law school do so because they choose to, not because they flunk out. They realize it’s not for them, and that’s a perfectly valid reason to pivot. Better to figure that out early than to end up with massive debt and no desire to practice.
If you’re at a top-tier (Top 25) law school, being in the top half of your class might be enough to land a lucrative summer associate job. These clerkships at big firms—places like Sidley, Jenner & Block, or Baker—pay very well and can fast-track your career, if that’s your desired path.
If you’re at a second- or third-tier school like I was, it’s a different story. You’ll likely need to be in the top 10 percent of your class to be competitive for those same jobs. It’s not fair, but it’s the reality. That said, big law isn’t for everyone. Your happiness and long-term success might lie elsewhere, and that’s okay, too. There are a lot of miserable attorneys making huge dollars and working 80–90 hours a week. Nothing wrong with knowing that isn’t for you.
And know that once you are a lawyer and practicing, nobody really asks where you went to law school anymore, or cares.
You’ll encounter brilliant classmates and professors, and some who are just average or below. You’ll also meet lawyers out in the real world who make you wonder how they ever passed the bar. That’s not meant to be harsh—it’s meant to show you that you don’t have to be the smartest person in the room to succeed in law or pass the bar exam. Walk over to your closest courthouse and see some attorneys in action. My guess is that it won’t blow you away. The old joke goes, “What do you call the person with the lowest passing bar exam score? Lawyer.”
Younger lawyers today have a huge advantage in one area—technology. Most law firms are notoriously behind the curve regarding social media, AI, and digital communication. If you know how to code, create content, or manage online branding, lean into that. Highlight it on your resume. Some young lawyer is going to become a millionaire teaching firms how to do TikTok right—why not you? Your knowledge of using social media and other technology can be an advantage, like speaking a foreign language.
This is probably my number one tip for success. It’s easy to let the workload consume you, especially if you’re prone to overstudying. But the truth is, if you put in consistent, focused effort—say, nine-to-five most weekdays—you’ll be in great shape. You don’t need to study until 2 a.m. every night to succeed. Working smarter, not longer, is the key. Sure, there will be late nights at times, but if you are doing that in the first couple of weeks, you are doing it wrong.
Your classmates, professors, and alumni connections can open doors that grades alone can’t. Go on informational interviews. Attend mixers and panels. Make friends, not just contacts. Many jobs in law are filled through referrals and relationships. The wider your network, the more opportunities you’ll have down the road. Don’t be too cool for school. You might meet and hang out with people that you wouldn’t have previously. This is all a part of growing up, and your success depends on it, too.
One of my most impactful experiences in law school was a mediation clinic. I became a certified mediator, worked on real disputes, and gained practical skills that no lecture could have taught me. Legal clinics—whether it’s criminal defense, immigration, family law, or environmental justice—offer real-world exposure and help clarify what areas of law you might actually want to pursue. It’s also a great resume builder. Just the other day, I was reading an attorney’s bio on their website, and it mentioned how they got their interest in employment law through their law school legal clinic. Twenty years later, they are still practicing employment law. That’s not unusual to see.
This can be hard to figure out, but some law firms have such terrible reputations that clerking for them can negatively affect your resume. Before taking a job offer, research that firm and see what their clients say about them. And use your career services office as a resource, so you don’t make a bad decision.
This should go without saying, but in the age of online oversharing, it bears repeating: if you wouldn’t want something coming up in a job interview, don’t post it. Most firms do background checks, including social media checks. Keep your online presence professional, or at least private.
Law school is challenging, no doubt. But it’s also an opportunity to live in a great city (if you’re in Chicago, lucky you), meet smart people, and have some fun. Take breaks. Explore. Go out with classmates. Know your goals and make time for what matters to you. I promise you that the most important thing is to graduate and pass the bar, but if you are miserable for those three years or miss out on life, you’ve failed. No lawyer I talk to ever says that they wish they studied more in law school or regret the fun they had when they had a chance to have it.
During law school, I met my wife, got a job that eventually led to starting my business, made some amazing friends, and even got to see a lot of Cubs games. Good luck—and remember, it’s a marathon, not a sprint.
