March 01, 2019 Feature

What I’d Tell My Younger Self

Rebecca Thomas, James E. Meadows, David Reischer, Cheryl Borland

If you’re like most lawyers, you’re probably much wiser today than when you stepped into your career in the law. In fact, if you could rewind the video of your life, you could probably freeze-frame certain moments that you now know were turning points. Or maybe looking back today, you now see so clearly what you’ve learned and recognize it as your guiding principles or mission in life.

We asked lawyers to do that look back to when they first began practicing and tell us what they’ve learned that they’d now tell their younger self. These responses from four lawyers are insightful and inspiring, and we think they’ll have you nodding along or even thinking of the lessons you’d pass on to the younger and less-experienced lawyer you once were.

The Joy of Discovering You’re VERY Good at What You Do

When you gain confidence, you also gain perspective. What you learn can change your life and career.

By Rebecca Thomas

Our firm recently hired a young attorney. After a meeting one morning, she told me she’s inspired by my confidence and success. I chuckled at first and thanked her, but later on, while sitting alone in my office, I began reflecting on just how far I’ve come since starting my career as a fresh, young attorney.

I’ve always practiced litigation, initially insurance defense followed by plaintiffs’ personal injury work, and, most recently, as co-owner of a law firm specializing in plaintiffs’-side medical malpractice. I prefer the writing aspect of litigation—formulating legal theories, drafting and responding to written motions, performing legal research, and so on.

When I started out as a young attorney, I passionately disliked oral arguments and trials because I thought I stumbled over words and sounded like a rambling amateur. This internal perception came not from any particular experience, but just the culture of being a brand-new attorney.

Sound familiar to you?

I’m certain many of you fellow litigators can relate. You excitedly walked into your first law firm job. You thought you were prepared for anything. You’d just recently dominated that monster of a bar exam!

Instead, you quickly felt like you were drowning in the ocean. You were given random assignments from several senior attorneys. “Draft an answer.” “Prepare discovery.” “Research charitable immunity.”

Your head was spinning. You were never actually taught how to practice law in law school. You desperately sought guidance from anyone. The receptionist. The mailroom clerk. The after-hours cleaning staff!

Eventually, you gained your footing and some confidence. You were given your own case load. You smiled because you finally had a bit of autonomy. Your smile quickly faded when you realized you weren’t the captain of the ship. Instead, you were a deckhand required to report case developments to and request authority regarding any defense strategy from an insurance adjuster. That’s right—an insurance adjuster.

For several years, you weren’t authorized to take depositions or argue motions in court because the adjuster didn’t feel you were experienced enough. Those matters were to be handled only by senior attorneys and partners. The constant undermining of your abilities impacted your confidence.

I was eventually “authorized” to handle those matters, but the internal damage was done. I always felt inadequate in my oratory abilities and simply dreaded oral argument and trial.

Wait, I’m actually good at this!

It wasn’t until I formed my own firm with no option but to handle those dreaded tasks that I gained the confidence I was lacking. I realized I was good—really good, in fact—at oral argument and trying cases.

Upon reflection, I can only attribute this boost in confidence to autonomy. There was no one looking over my shoulder and criticizing how I handled something or undermining my abilities. I could follow my instincts and handle the matter how I best saw fit. Simply, I was free to be an attorney.

I wish it hadn’t taken forming my own firm to become fully confident as a lawyer. I still favor the writing aspect, but I know for certain it’s not due to a lack of confidence or fear.

As the old adage goes, “If I’d known then what I know now,” I’d have been more confident in myself and my work. I’d have focused more on my achievements and spent less time stressing over my own perceived inadequacies.

I was good then, and I’m even better now. As a more senior attorney, I hope to encourage any new attorneys we hire with autonomy—when appropriate and within reason—to follow their instincts and become confident in their abilities.

Dear Self: Where Exactly Are You Going?

An end game can help you get where you want to go, but you’ll also have to accept some risk.

By James E. Meadows

Dear Jim,

As you embark on your career in the law, I find it difficult to give you concrete advice. The general field of law is, in reality, very complex; there’s no sure-fire way to be happy or make money. Instead, my advice is abstract, but I hope it’ll still be helpful: Take risks.

I grew up in rural North Carolina, attended a small law school in the same state, and, in all honesty, I probably should have ended up practicing there as well. I defied this expectation, deciding to take a job in New York City with few contacts and no family nearby. I worked there for 10 years, in a city seen as cold and cutthroat.

Although it might be cliché, I was able to succeed there because I worked hard and loved my practice. I chose technology law because it was dynamic; it changed about every five years as technology itself evolved, and so I was never bored.

Hardware law gave way to software law, which in turn combined with telecommunications to involve major computer systems and outsourcing, which led to the internet, which led to ecommerce, which led to privacy and data security, which led to social media, and many smaller steps in between.

I also focused on contract law because, at the end of a deal, both sides are usually reasonably happy and prepared to work together over the terms of the contract. I loved that aspect of the law, and, in turn, I worked much harder than I would have if I’d have disliked my job.

Know where you’re going

However, one of the most essential lessons I’ve learned is to have an end game. I always knew I wanted to end up with a more fluid practice; I didn’t enjoy the traditional structure of a law firm and knew that many of my colleagues didn’t, as well.

When I had the opportunity to take another risk a few years ago and create that more fluid type of firm, not only for my benefit, but for others’, I jumped at it. Now, I operate mostly electronically, which affords me a much better work-life balance, enabling me to live at the beach while still handling work for Fortune 100 clients in New York City.

I knew this was my end game; I was done with the hustle of the city but not ready to retire. Starting a new firm was most definitely a risk, but it was a calculated one I’d been considering for a long time. My willingness to take that risk in launching a cloud-based law firm has not only reshaped my practice and life for the better, it has resonated with more than 60 other seasoned lawyers who have joined our firm because they were also looking for a better way to practice law.

If you take risks, work hard, and work smart—and have a general idea of where you want to end up—you’ll be a successful lawyer.

All the best,


Money Doesn’t Nurture Your Spirit

It’s easy to lose sight of your dreams when you’re trying to pay the bills. When you find your focus again, the result is much sweeter.

By David Reischer

It’s 2001, and I’m staring out the window of my office in downtown Manhattan.

The downy snowflakes are slowly wafting into my view on this late Friday night. The preoccupying thought of my mind is, “How on earth have I accumulated more than six figures in student loan debt working at a big law firm that’s misery personified?”

I haven’t eaten properly since I started this job, and I’m overwhelmed with work-related stress. This 2001 period was one of the most disheartening periods in my life, and very different from how I had envisioned my legal career when I first began law school just four years earlier.

When you forgot why you came

I’d entered Brooklyn Law School in 1997 with a passion to learn about the legal system and the desire to do pro bono work, to “give back” something to the larger world community. I myself had come from a single-parent household where I watched my mom struggle with paying bills by cleaning apartments to receive extra income. When my father passed away, my mother couldn’t afford any legal services, and I remember my mother representing herself pro se in a holdover action with our landlord.

Perhaps it was naive of me, but I’d always wanted to provide help to those most in need of legal assistance, and this desire was the main reason I went to law school. In fact, that’s the primary reason I chose to attend BLS. It’s known for its public interest clinics that train law students in a hands-on fashion to satisfy legal needs in low-income and underrepresented minority neighborhoods in a variety of public interest areas.

The clinic programs at BLS teach the practical skills on a wide range of legal issues, such as filing an asylum application for immigration to the United States or applying for a restraining order to protect against domestic abuse.

In my case, BLS provided me with an internship program to clerk at the Equal Employment Opportunity Commission, where I spent a considerable amount of time researching and writing legal memorandum and bench memos for an administrative judge to protect people from wrongful discrimination in the workplace.

My clerkship experience at the EEOC, in which I was afforded the opportunity to learn how to help people navigate the complex process of filing a complaint with the EEOC, was one of the most personally rewarding experiences of my youth. It was truly a wondrous feeling to help people who needed legal assistance with their legal problems.

When I remembered my dreams

When I graduated BLS in 2000, the economic reality of finding a job that would allow me to meet the obligations of my exorbitant student loans took precedence over my former desire to become a lawyer out of social magnanimity and philanthropic principle. I thus began working at a major asbestos litigation firm in downtown Manhattan because the pay was quite above average.

However, the day-to-day machinations of prepping for complex litigation at this firm was mind-numbingly depressing. Watching snowflakes fall outside my window on that 2001 weekend before Christmas, I’ll never forget the piled-high medical reports for which my task was to separate and categorize based on mesothelioma injury classification.

I oftentimes reflect upon this late Friday because I knew I was at a career crossroads, and it was my reflections that night that led me to tender my resignation from the firm on the following Monday morning.

It was this decision to resign that became the career predicate to setting up my own solo law practice and launching an online business that allows people from all over the world to get affordable legal advice on the internet. I launched an online legal referral service at with venture capital from other philanthropically minded people who are passionate about providing pro bono legal services to low-income people.

If I could communicate with my younger self, I’d emphasize the importance of recognizing my dreams and motivations. It’s easy to defer dreams and lose sight of one individualized purpose. In my case, I could have saved several years of career misery if I’d only realized that money alone doesn’t nurture one’s spirit. Instead, you must never lose sight of your real goals.

Be Kind to Everyone, Including Yourself

The path to happiness and contentment for this lawyer wasn’t direct or easy. But she wouldn’t change a step.

By Cheryl Borland

Dear Younger Cheryl, where did the time go?

What a wonderful and exciting ride this has been. And, just so you know, it was certainly worth it at the end. Your vision and perceived road, although you had a unique start, has hardly turned out the way you expected.

Now, having reached a modicum of success in life and the law, I often look back on the decisions I made along the way, as well as some of those decisions that were made for me. Some took me to places I’d never have fathomed. Some still carry a bit of an ouch factor that cause me to wonder if I’d do things differently. But overall, I wouldn’t change a thing.

I harbor very little regret and revel in the beauty of my life.

The law was different then

My career began in the era when we thought we could do it all and were indeed expected to be able to do it all. It was still a time when women attorneys weren’t respected by attorneys, judges, or clients. I remember a lecture I attended by a judge that focused on proper court attire. We were admonished not to wear “beach wear” to this judge’s court, which meant we had to wear suits with skirts, not pants; stockings; no flashy jewelry; and for goodness sake, we were told, don’t wear open-toed shoes. Oddly, I don’t think my male classmates got that same lecture.

I opened Griesing Law’s Cincinnati office in March 2017. The firm was formed eight years ago to retain, grow, and develop women attorneys, a truly novel concept within the legal community. Before I joined this firm, there were times that I hated my job and wanted to quit. Clients were difficult. Firms were difficult. Opposing counsel were difficult. Cases were difficult.

I was often discounted by BigLaw male attorneys. I was often mistaken for a paralegal or secretary instead of an attorney. But I was fortunate in having some old, white-haired men who became not only mentors but sponsors (sadly, it wasn’t other women who had senior roles who were my mentors or sponsors). So rather than quitting, I found a way to use my experience to refocus my career so that it was energizing and exciting again. I began to view my practice as being an entrepreneurial legal professional.

The joys of being introverted

My secret skill has been being an introvert in a sea of extraverts within the legal arena. My attention to detail and my ability to be a discerning listener has paid huge dividends. Often, it’s not what’s said, but what’s unsaid, that’s the most important.

I also began to see each change in my career as a way to make sure I was truly following my passion and to recognize that, although it seemed like I often didn’t have control (you know how we lawyers love control), I had opportunities to learn, to grow, to be uncomfortable, and to truly discover.

Along the way, I learned a few lessons that have stayed with me. One or two particularly difficult clients have been excellent teachers, as has a lack of collegiality among opposing counsel (or sometimes within my own firm). Both have been quite humbling, but they taught me to know my value. My time and expertise is valuable irrespective of whether others saw or acknowledged it. I’ve spent my career living by a Dr. Seuss quote: “Say what you mean, and mean what you say.”

Finally, I never gave up on my goals and dreams. I knew I wanted to be a lawyer, but I wanted to be a lawyer who made a difference. I learned to practice self-care and to remember that my family was truly important. I traded a big salary to be able to leave my office at 4 p.m. to watch my son play baseball and soccer and to watch my daughters’ dance lessons.

Before we had the ability to work remotely, I remember getting a call from my children on Christmas Eve wanting to know when I’d be home. They also wanted to know what could possibly be more important than cooking Christmas Eve dinner and Christmas cookies? Unfortunately, it was the Securities and Exchange Commission. But after that, failing deadlines that I couldn’t control, I spent the week between Christmas and New Year’s with my family.

And when those self-doubts crept in, I remembered that I’m a brave, strong, resilient, sweet, and beautiful person. I work hard and try to remember to be kind—to others in the profession, to my clients, to my family but, most importantly, to myself.

CHERYL BORLAND is of counsel at Griesing Law in Cincinnati and chair of the firm’s trusts and estates practice group.


Rebecca Thomas

Rebecca Thomas is a founding partner at Thomas and Wickenheiser LLC in Quincy, Mass., where she focuses on representing injured parties in medical malpractice actions.

James E. Meadows

James E. Meadows is the founding partner of New York City-based Culhane Meadows PLLC. He focuses on technology law, including internet and ecommerce, privacy and data security, cloud computing services, and outsourcing.

David Reischer is an attorney at and CEO of Legal Marketing Pages Corp. in New York City. The firm launched, whose mission is to provide affordable legal access to consumers who need high-quality legal advice, and, which seeks to increase access to legal advice and information to those who can’t afford it.