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Sheereen E. Middleton of Middleton Legal: “Never underestimate the power of effective marketing”

Never underestimate the power of effective marketing — My first law office launch was a complete and total bust. I had no experience as a business owner, and did not value marketing. I thought I could announce that I was in business, and the clients would come. Wrong — it wasn’t until I started to market my practice that […]

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Never underestimate the power of effective marketing — My first law office launch was a complete and total bust. I had no experience as a business owner, and did not value marketing. I thought I could announce that I was in business, and the clients would come. Wrong — it wasn’t until I started to market my practice that I began to gain clients.Lawyers need to learn to optimize marketing and sales to have a successful practice. I also teach them some of the techniques that worked well for me, particularly using social media.


As a part of my series about “5 things I wish someone told me when I first became an attorney” I had the pleasure of interviewing Sheereen E. Middleton, Esq.

Sheereen E. Middleton, Esq. is from Silver Spring, MD, and moved to Florida to attend the University of Miami in Coral Gables in 2002. While attending UM, Sheereen was a member of the cheerleading squad and cheered for the football team, volleyball team, and basketball team. After graduating from UM, she attended law school at St. Thomas University in Miami Gardens. Sheereen is a licensed Attorney and Realtor® in both Maryland and Florida. Today, she practices Bankruptcy, Real Estate, and Estate Planning. When Sheereen is not in the office, she enjoys spending time at the beach, and being amongst friends and family. She volunteers in the community and has a passion for helping others. Her professional approach and knowledge are key in resolving clients’ issues.


Thank you so much for joining us! Our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law?

While attending law school at St. Thomas University, I participated in the bankruptcy clinic and provided pro bono services. Participating in the bankruptcy clinic allowed me to see the immediate impact that we, as attorneys, can have on consumers. I fell in love with providing pro bono services and have an ethical duty as an attorney to do so. Since 2013, I’ve dedicated 20% of my bankruptcy practice to servicing pro-bono clients.

Can you share the funniest or most interesting story that occurred to you in the course of your law career?

In 2018, I was three months postpartum when I got laid off from my law firm job in Florida. After working a series of low-paying gigs, I relocated to Maryland and worked as a contract lawyer for other law firms. I was working hard, driving all over the place, and barely making any money after the cost of child care and commuting. My sisters saw something in me that I knew I had all along but was scared to try. I set out to start bankruptcy practice full time, and it was the best decision I’ve ever made. I’ve been able to secure my career, provide for others, and make a difference in people’s lives. It’s been gratifying.

What are some of the most interesting or exciting projects you are working on now?

I’m currently working on “Bankruptcy Buildout,” a book designed to teach lawyers how to launch, grow and scale their consumer bankruptcy practice with confidence.

What are some of the most interesting cases you have been involved in? Without sharing anything confidential, can you share any stories?

I recently had a bankruptcy case where my client filed for protection from creditors. One creditor violated the bankruptcy law by continuing to contact my client in an attempt to collect a debt. They called him over 50 times! We ended up filing a lawsuit against this creditor and settled the dispute.

Which people in history inspire you the most? Why?

Barack and Michelle Obama, they are the quintessential presidential power couple.

What advice would you give to a young person considering a career in Law?

Go for it! It’s extremely rewarding and makes an immediate impact on the people you serve.

If you had the ability to make three reforms in our judicial/legal system, which three would you start with? Why?

1. Make alternative dispute resolution mandatory before filing a civil lawsuit because a lot of time and money is wasted with frivolous claims or suits that lack merit;

2. Make pro bono legal services readily available for those who are unable to pay attorney’s fees because they deserve legal justice and relief;

3. Criminals convicted for crimes that are no longer considered crimes, particularly marijuana possession, should be released and records expunged because having a criminal record adversely affects African Americans disproportionately.

How have you used your success to bring goodness to the world?

In 2020, I received recognition from the Maryland Volunteer Lawyers Service for taking more than 10 cases in the fiscal year, as well as a new award category that they created for me. The MVLS made the COVID19 Response award for me because when the pandemic began, I volunteered to take on all of the bankruptcy cases they had on file for Baltimore City residents.

I know this is not an easy job. What drives you?

My daughter drives me the most. She is watching every move I make. I want to be an excellent example for her, not necessarily to be like me, but to be better than me, mentally, spiritually, and financially.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or an example for each.

1. Law school performance does not necessarily determine your ability to be a great lawyer.

As a law student, I STRUGGLED‼️ I would come home and cry out of fear and frustration. We weren’t reading textbooks, we were reading cases — huh? My performance on ONE exam determined the whole semester. I was having a hard time adapting to this new learning mode…While in school, I was kicked out of class twice for being unprepared and placed on academic probation, which canceled my scholarship.

*Reality Check*

The School of Life taught me that anything worth my while, wasn’t going to come easy. I got my stuff together and turned it around. I worked hard, dedicating my time and my attention to perfecting this new skill set. God challenged me, and I discovered untapped gems that would’ve never been unveiled if I didn’t experience this hardship. By the grace of God, I ended my law school career on the Dean’s List with excellent academic credentials. By the favor of God, I passed the bar exam the first time I sat for it. It’s grit that keeps you going!

2. Put all of your time and energy into preparing for the Bar Exam

This is key unless you don’t plan on practicing law after law school. It is imperative because your law license can open doors and new opportunities. The Bar is designed to be very tricky, so get used to it, and practice essays over and over and over again.

3. Find a Mentor

A mentor can show you the ropes, introduce you to like minded individuals, and can be there to bounce ideas off of. They have usually been through more, and can guide you. Save yourself the time and pain of making mistakes that can be avoided by having a conversation with someone who has been around longer than you, and has seen more.

4. Be open to continuing education

It’s okay if you don’t know everything, but make an effort to learn. The laws change, and lawyers need to be in the know. Be open to learning other areas of the Law too. As the demand changes, you may need to adjust your business model and the offered services.

5. Never underestimate the power of effective marketing

My first law office launch was a complete and total bust. I had no experience as a business owner, and did not value marketing. I thought I could announce that I was in business, and the clients would come. Wrong — it wasn’t until I started to market my practice that I began to gain clients.Lawyers need to learn to optimize marketing and sales to have a successful practice. I also teach them some of the techniques that worked well for me, particularly using social media.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

I’d love to have a private meal with Jay-Z. I’ve always admired his art, as well as his entrepreneurial endeavors. When I attended his live 4:44 show, he spoke to the audience in between sets, and dropped so many gems! I wish I had a notepad, or at least recorded it. He’s super wise, and has made excellent business decisions. Plus, there may be a bonus of Bey attending 🙂

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