Break Into Law School® Podcast
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Break into Law School® is the podcast for students who are ready to break down generational barriers to law school and walk confidently into their future.
This podcast provides transparent, quality, and ethical law school advice in a way that is uplifting and relatable.
Sydney Montgomery, Esq, is a law school admissions consultant specializing in working with first-generation and minority applicants. She herself is a first-generation graduate of Princeton and Harvard Law School. Through Barrier Breakers®, she and our team have helped over 7,000 students gain admission to law school.
Are you struggling with information overload? Are you getting lost in Reddit and Google? Are you feeling stuck, not sure what to write about, not sure how to even begin the application process? Join a community of students who are choosing to stop the cycle of confusion and missed opportunities and find quality and ethical answers to their application questions.
No scare tactics here. No tearing people down. No shaming anyone. This show is all about leading with love, uplifting you, and encouraging you as you step confidently into your career as an attorney.
Meet Your Hosts

Ep 53: Succeeding in Law School with Alison Monahan
Alison Monahan, co-founder of Law School Toolbox and founder of The Girl’s Guide to Law School, joins us today to talk about succeeding in law school. Alison has also been involved in a wealth of publications and shares what she has learned through helping law school students in their education and careers. Alison shares some real gems of advice and insight into how to make the most of law school and graduate without regrets.

Ep 52: Personal Statements with Former Harvard Law Admissions Officer
I am thrilled to share this episode with you because we're joined by Monique Atkinson, former Harvard Law School admissions officer and current Associate Law School Consultant here at SMC. Monique and I discuss everything you need to know about personal statements - and trust us, you'll want to pay attention because your essays can make or break your application. Learn which topics to avoid and which to highlight, the kinds of writing styles to adopt, as well as proofreading strategies for your personal statement.

Ep 50: Berkeley Law, Full-Tuition, 152 LSAT - Tiffaney's Story
I'm especially proud and excited to share this story with you. Tiffaney Boyd, a former boot camp client, will be attending UC Berkeley School of Law this fall with a full-tuition scholarships. Get this....she had a 152 LSAT. Tiffaney is living proof that your LSAT is not the entirety of your application and you can still get into a top school WITH MONEY when you know how to emphasize your strengths. Watch this interview to hear Tiffaney share her story, her journey as a re-applicant, and tips and advice she has for applicants.

Ep 49: Tackling the LSAT with Expert Tutor Mena Pirone
I am very excited for this episode because I am joined by Mena Pirone, fellow Harvard Law alumna and founder of Logic Games Pro, a customized LSAT tutoring service. I ask Mena common questions and misconceptions about the LSAT, how/when students should approach seeking external help with their prep, and both the direct and indirect factors that cause disparities in scores among students of different backgrounds. We also talk about the future of test-optional policies among law schools, and why it's still a good idea to keep studying for the LSAT.

Ep 48: Getting Started On Your Law School Applications
May is the perfect time to start working on your law school applications, but you may be wondering HOW to start exactly. In this episode, I'm doing to discuss how and why to brainstorm, how to plan out your application materials with a month-by-month example, and how to begin working on your essays and non-written app components.

Ep 47: Reapplying to Law School: An Immigrant's Journey to Yale
I'm very excited to share this episode with you all because I am joined by my former client, Ebele Eseka, who has just committed to Yale Law School!! Curious to know about the process of reapplying to law school? How about the law school admissions experience as an immigrant? Tune in for this fun conversation as Ebele shares her experience and advice to fellow applicants. You can reach Ebele at okbyeve@gmail.com

Ep 46: When to Start Preparing for Law School
In this episode of Break Into School, I discuss when you should start preparing for law school. I'm also going to give you a month-by-month breakdown of how you should spend your time as you put together your materials both written and non-written.

Ep 45: Transfer Admissions with Harvard Law School Dean of Admissions
I'm so excited to be joined today by Kristi Jobson, Assistant Dean for Admissions and Chief Admissions Officer at Harvard Law School. We're going to discuss her background and role at HLS and then dig into how transfer applications really work for law school. Kristi will break down common myths surrounding the transfer process, how transfer applications differ from regular applications, resources available to transfer students, as well as some really great advice for students. This one's a gem so I hope you enjoy listening!

Ep 44: How to Get Your Law School Loans Paid For
In this episode of Break Into Law School, I am joined by Alice Foley, Associate Law School Admissions Consultant here at S. Montgomery Admissions Consulting. Alice graduated from law school in 2013 and has since worked in admissions. She'll shed some light for us on public service loan forgiveness programs and afterwards, I will be discussing loan repayment assistance programs. We're going to cover how these programs work, who qualifies, and how COVID has changed them.

Ep 43: The New Rankings - Should You Care?
In this episode of Break Into Law School, I'm going to have a conversation about the new USNWR law school rankings.

Ep 42: The Do's and Don'ts of Waitlist Responses
In this episode of Break Into Law School, I'm going to be discussing the do's and don'ts of responding to waitlist offers.

Ep 41: How to Decide Between Your Law School Offers
In this episode of Break Into Law School, I'm going to discuss how to decide between your offers of admissions.

Ep 40: What to Do if You Haven't Heard Back From Law Schools
In this episode of Break Into Law School, I'm going to discuss what to do if you haven't yet heard back from law schools.

Ep 39: How to Approach Scholarship Negotiations
Many of you have started to receive offers and acceptances (yay!) and this season always brings with it the conversation of scholarship "negotiation." In this episode, I discuss this term and ways you can approach this process with a different and, arguably, healthier perspective. I will also share some personal stories of how I approached admissions and attained more money.

Ep 38: All About Pipeline Programs
In this episode of Break Into Law School, I'm going to discuss what a legal pipeline program is and when you should start applying. I am also going to talk about how to figure out which pipeline is right for you, how it will actually benefit you, and I'll share examples of some great pipelines for you to check out.

Ep 37: Navigating Admissions, Mental Health, and Scholarship Negotiations with Mike Spivey
Today I am joined by Mike Spivey, former dean of admissions at Vanderbilt Law School and founder of Spivey Consulting Group. In this episode, we discuss the changing landscape of the admissions world, interesting stories from his time as Dean, processing and navigating mental health in the application process, and how to approach scholarship negotiations. It's a special episode and I'm lucky to call Mike a friend of mine.

Ep 36: Can You Still Apply This Late in the Cycle?
In this episode of Break Into Law School, I want to have an honest discussion about application timing. It's February and I know many applicants are wondering if it's too late in the cycle to still apply. I specifically am going to discuss who can still apply, who would really benefit by postponing their application, and how you should feel about the February and March LSAT.

Ep 35: How Much Debt is Law School Worth?
In this episode of Break Into Law School, I'm going to be talking all about debt. How much debt should you be taking out for law school? How does debt relate to your future career as a lawyer? How can you minimize the amount of debt you'll have after you graduate? The good news is you don't have to pay off loans forever just to attend law school. Conversely, you don't have to give up a top school just to live debt-free.

Ep 34: You've Been Waitlisted, Now What?
In this episode of Break Into Law School, I want to talk about waitlists. What does it really mean to be waitlisted? Should you be happy about it? What steps should you take once you've been put on the waitlist? I am going to discuss these questions as well as what to include in your letters of continued interest.

Ep 33: Paying Your Bills While Attending Law School
How do you pay your bills and personal expenses while attending law school full time? How much should you take out in loans? What's the smartest money move to make as a student? In this episode of Break Into Law School, I want to discuss with you how personal allowances work and how to get them, how much to take out in loans, and alternative ways to earn money for your bills.