Any Regrets About My Law School Journey?


I recently saw a Quora question asking attorneys if they regretted anything in their journey. I thought it was an interesting question, and after some reflection, I would unequivocally say: no.

Going into law school, I knew that I wanted to work in Big Law, practice for a few years, and then step back and assess my updated career goals. I was a Big Law litigation associate for about two-and-a-half years before I left to start a media startup called Suspend The Rules.

I was fortunate to attend a solid school that offered many on-campus interview opportunities. While I ultimately found my Big Law gig through some creative tactics, Penn maximized the chances that I would find a job. It can be harder to enter Big Law at other lower-ranked schools, especially if you have poor 1L grades. You have a bit more leeway when searching for your first job if you attend a “prestigious” school. The prestige of your law school can also provide a solid credential if you’re trying to do something outside the legal field—as I currently am.

I also think that attending a law school near three major metropolitan areas helped me secure a Big Law job. Location is an underrated, yet crucial determinant when you are vetting law schools. Being in Philadelphia and relatively close to New York City and Washington D.C. was certainly helpful as I was searching for a job.

As for Big Law itself, I had a good experience. I worked with extremely bright attorneys on complicated matters. It’s not for everyone, and I think that you should be aware of the realities before choosing this path. Sure, the compensation is awesome, but you’ll be making sacrifices (like personal time and perhaps even friendships).

Ultimately, law school and legal practice taught me certain skills that I use beyond legal practice. I’m specifically thinking of attention to detail and managing client expectations. The more I practiced, the stronger I became.

That said, I’m not saying people should go to law school solely to learn these skills or to use a law degree has a “backup plan.” Everyone has their own reasons for going to law school and the financial angle plays a disproportionate impact on whether law school is “worth it.” You’ll have to evaluate whether the costs (including opportunity costs) outweigh the benefits you receive from a J.D. For me, the benefits outnumbered the costs.