Julia Hensel: Your career did not begin in law. What inspired you to make the transition from teaching to becoming an attorney?
Mary Ellen O’Connor: I was a teacher for six years. I had just finished my second master’s degree and was on maternity leave after giving birth to identical twin girls, two of my three children.
The twins were born prematurely and had some health issues as a result. They also did not sleep. If one was asleep, the other was probably awake, so for several months I was essentially up around the clock.
One night at about two in the morning, toward the end of January, I was watching Law & Order. I remember sitting there thinking, “Why didn’t I go to law school? I could do that. I want to go to law school.”
As a kindergarten and second-grade teacher, I had worked with many children who had special needs and were not always receiving the special-education services they were entitled to. I became a strong advocate for them during special-education meetings.
At first, I thought perhaps I could combine that experience with law and become involved in special-education advocacy.
That same night, I went online. This was during the dial-up internet days, so I am dating myself. I discovered that the LSAT was coming up and that if I registered immediately, I could still make the late-registration deadline.
I suddenly had about two weeks to prepare.
The Princeton Review course was around $1,800, which I did not have at the time. My daughters were on special formulas, and that simply was not an option.
I looked for a preparation book online, but even that was about $100 and would not have arrived quickly enough. So I convinced my mother to go to the library with me without telling her exactly what I was doing.
When she eventually found out, she thought I was crazy. She said, “You have three babies. You cannot go to law school.”
I told her, “I’m not going to law school. I’m just taking the test.”
The LSAT preparation book at the library was a reference book, so I could not even take it home. I photocopied some questions simply so I would have an idea of what the exam looked like.
Then I went in and took the LSAT.
Believe it or not, I did extremely well.
I started receiving interest from law schools before I had even submitted applications.
That was not what I had expected at all. I had imagined perhaps going back to school once my daughters were older. But sometimes an opportunity knocks, and you have to open the door.
I started looking at schools in the New York area and ultimately chose the City University of New York because it had daycare. It was only seven dollars per child per day, and I had received a scholarship, so everything seemed to be lining up perfectly.
Then, after I had already enrolled, I learned that the daycare did not accept children until they were 20 months old.
We had to scramble, but everything worked out.
I started law school in August 2001. During my second week, September 11 happened.
This August will mark 25 years since I began law school. I do not regret it for a minute.
It began with one sleepless night after many sleepless nights. My mother asked whether I was crazy, and perhaps I was.
But I also believe things happen for a reason.
Julia: How did you manage law school while raising three young children?
Mary Ellen: I think having so little time actually helped me because I did not have enough time to overthink everything.
People talk about test anxiety and study anxiety. For me, it was simply, “Get it done and move on.”
A paper was finished? Good enough. Move on to the next thing.
I did not have time to spend days wondering whether I had studied enough, read enough case law, or prepared enough.
I tried to keep things in perspective. I was going to do the best I could and keep moving forward.
Sometimes when people are anxious, they convince themselves they have not done enough when they actually have.
There were also moments when I would think about people I knew who were already attorneys and tell myself, “If that person can do it, clearly I can do it.”
Having three children and so many responsibilities forced me to focus on what actually needed to get done instead of trying to make everything perfect.
Julia: What eventually led you to open your own firm?
Mary Ellen: Like many things in my life, it happened somewhat by circumstance rather than through a carefully designed plan.
But many of the things I did not plan have turned out to be the best things that happened to me.
At the time, I was working for another attorney. We had recently moved, and my daughters were entering a new school district. I wanted to take them to their first day at their new school.
The managing attorney would not let me take the day off.
That was my sign that it was time to leave.
What made the situation especially striking was that I had previously had the exact opposite experience while working in-house for an insurance company.
When my daughters were starting kindergarten, I had only been at the company for about two weeks. The CEO, Steve, noticed that I was scheduled to be in court on their first day of school.
He came to me and said, “Don’t you have kids? When do they start school?”
I told him it was Wednesday, but that I was scheduled for court.
He said, “You can’t go to court Wednesday. You have to bring them to school.”
I told him I had just started and was not even through my probationary period, so I could not work from home.
He said, “I’m the CEO. I’m telling you that you can.”
It was a completely different leadership philosophy.
When I decided to leave the firm years later, I went back to Steve and asked about returning to the insurance company.
He gave me a piece of advice I have never forgotten: “You never go back in your career.”
He told me I could come back, but not simply into the same in-house attorney role I had previously held. I needed to move into something different.
Then he gave me another option.
He said that if I wanted to start my own practice, he could provide enough work to keep me busy while I built my own clientele.
I was extremely fortunate.
I did not jump out of the plane hoping a parachute would appear. I went out with a parachute.
I had guaranteed work from the insurance company while I began building my own practice.
Julia: What were some of the biggest challenges during the early years of building the firm?
Mary Ellen: One of the biggest challenges was that I was spending so much time doing work for the insurance company while simultaneously trying to build my practice and raise my children.
Looking back, I probably devoted too much time to the insurance company and not enough to growing my own client base.
In hindsight, perhaps I was spending 80 percent of my time on insurance-company work and only 20 percent on my practice. A 50-50 split might have made more sense.
But hindsight is always easier.
At the time, I was grateful for the work because it provided security. I have always liked having a security blanket.
Eventually, that security blanket disappeared. The insurance company was legislated out of business.
At first, I was terrified.
I kept wondering, “What is going to happen?”
In reality, having that security blanket taken away was one of the best things that ever happened to me.
It gave me my time back.
Suddenly, I could devote those hours to building my own clientele and growing the firm.
Sometimes ripping off the Band-Aid is exactly what you need.
Julia: You have built a large team, including many remote and global team members. How have you approached leadership and company culture?
Mary Ellen: I have worked in some form of hybrid or remote environment since around 2005.
Back then, telling someone that you worked from home one day a week was unusual. People would look at you as though you were doing something completely different.
Again, a lot of that goes back to Steve, the CEO of the insurance company.
He was particularly good at developing women leaders. He actively supported women within the company and helped them move into leadership positions.
That experience influenced the way I lead today.
I try to ask myself, “If I were the employee, how would I want to be treated?”
I do not like being micromanaged. Sometimes I may need someone to remind me that a report is due, but overall, I want to hire people I can trust.
It is trust, but verify.
I also believe in treating people with respect.
If someone tells me at four o’clock that they have a terrible headache and need to leave, my response is generally, “Fine. Go. I’ll see you tomorrow.”
What is accomplished by forcing that person to sit there miserably for another hour?
I have worked for bosses I loved and bosses I did not love, so I think about the type of environment I would want to work in.
Not everyone would necessarily want to work in the environment I have created, and that is okay.
But I have many women on my team and many employees with families. Whenever possible, we try to accommodate the realities of their lives.
One person may prefer working weekends. Great. We need people available on weekends.
We try to work around people’s schedules where we can.
I jokingly tell everyone, “If I won the billion-dollar lottery, I wouldn’t be here either.”
We all work because we need to make a living. So while we are here, we should try to make the experience as positive as possible.
And when you turn the computer off, leave it off. Go spend time with your family and friends.
Julia: How do you keep a remote team connected when people are not sharing the same physical office?
Mary Ellen: We are intentional about creating opportunities for people to interact beyond their daily work.
Even in a traditional office, some people love standing around the water cooler talking, and others never go near it.
With a remote team, you have to create some of those opportunities.
Sometimes we organize 15-minute coffee breaks and pair team members so they can jump on Zoom together and simply talk.
We have held virtual bridal showers. Everyone might contribute a favorite recipe, and we create a recipe book for the person getting married. We play games like bridal bingo.
When someone on the team is expecting a baby, we may do a virtual gender reveal together.
Once a month, we have a game day where one team member creates a virtual game for everyone.
We also have an off-topic Slack channel where people share pictures from their lives and things they have done with their families.
If you were sitting next to someone in an office every day, you would naturally learn those things about them.
With remote work, you have to be more deliberate about creating those moments of connection.
Julia: Do you believe work-life balance is actually possible?
Mary Ellen: I think there can be work-life balance, but I also think there is a lot of imbalance.
Pretending that everything is perfectly balanced all of the time is unrealistic.
For me, work-life balance means having the ability to do things when I want to do them while still completing my work.
My children are older now, so my version of balance looks different than it did when they were young.
For example, we rent a house on Cape Cod. Recently, I was working there. At 4:30 in the afternoon, I shut down my computer, grabbed my Kindle, and went to the beach for an hour and a half.
Then I came back, had dinner, and worked again from about 8:30 until 10:30.
Some people might look at that and say, “That is not work-life balance. You are working at 10:30 at night.”
But for me, it is.
I do not particularly need to watch television from 8:30 to 10:30. I would rather work during that time if it means I can spend part of the afternoon at the beach.
Work-life balance looks different for different people.
When my children were young, balance might have meant being able to go into their classroom in the middle of the day and read a book to the class without having to sacrifice the entire day.
When I was a teacher, if I wanted to do something like that, I would have needed to take the whole day off.
As an attorney running my own practice, I had more flexibility.
In 2015, we took a family trip to California. Because of the time difference, I could work from six in the morning until nine in California, which covered nine to noon in New York.
By the time my children were ready to leave the hotel at nine, I had already completed the important part of my workday.
At that point in my life, I needed to continue working and earning money, but we were still able to have a family vacation.
It was the best of both worlds.
Everyone goes through different seasons of life.
Today, my children are grown. My balance may involve going to the beach by myself with a book.
When they were little, balance meant being home when they came home from school or spending an afternoon with them when I could.
I certainly was not there every afternoon. Sometimes I was in court.
But if I could be there twice a week, that mattered to me.
Julia: You handle workers’ compensation and Social Security disability matters, often involving people going through devastating circumstances. Are there cases that have been especially meaningful to you?
Mary Ellen: We see many unfortunate and tragic situations in workers’ compensation and Social Security disability cases.
Death cases are especially difficult for me.
I feel deeply for widows and widowers whose spouses die because of their work.
Many death claims are also controverted, meaning the insurance company does not simply accept responsibility. We have to fight.
I work hard for every client, but with a death case, I work incredibly hard.
I research everything. Even when I know the relevant cases inside and out, I double-check them and read them again.
Sometimes I prepare as though it were my first hearing or trial because I understand what is at stake.
For these widows and children, this may be their one opportunity to receive the benefits they are entitled to.
One case that is particularly meaningful to me involved an attorney who became a mentor of mine.
His law firm was in Lower Manhattan after September 11. He was not involved in rescue or recovery work, but he went into his office every day.
Lower Manhattan was still filled with dust and environmental hazards. People working in that area were being exposed to many of the same toxins as those participating in rescue, recovery, and cleanup efforts.
Unfortunately, many cancers associated with 9/11 exposure have long latency periods.
He was ultimately diagnosed with cancer and passed away in 2022.
I was very close with him and his wife.
I brought a claim on his wife’s behalf, arguing that his death was related to his occupational exposure while working in Lower Manhattan.
The insurance company fought us every step of the way.
After nearly four years, we finally had the trial, and the judge ruled in the widow’s favor, finding that his death was related to that exposure.
That case is still very fresh in my mind, and it means a tremendous amount to me.
Julia: Are there other cases that demonstrate the kind of challenges your clients face?
Mary Ellen: I have another case involving a gentleman who was struck and run over by an 18-wheeler.
Then, while he was undergoing surgery, there were additional medical complications. Today, he is in a wheelchair and has significant neurological problems.
The insurance company provides a home health aide, but only for seven hours a day, Monday through Friday.
We are fighting to allow his wife to be compensated as a home health aide as well because his needs obviously do not disappear outside those limited hours.
Cases like that are why, at this point in my career, I am particularly drawn to matters where I feel completely committed to the fight.
My associates are extremely capable and can handle much of the work, which gives me the ability to become especially involved in cases where my experience can make a significant difference.
I spent years working on the insurance side before moving to the claimant’s side, so I understand how the other side evaluates these cases.
Over the years, I have also been involved in developing some of the case law that I now rely on when representing clients.
That experience becomes very valuable when you are dealing with an especially complicated claim.
Julia: Your clients are often experiencing significant trauma. How do you help your team manage the emotional weight of that work?
Mary Ellen: We joke about the phrase “counselor at law,” but there really is a counseling component to this work.
Our clients are dealing with many different forms of trauma.
They have been injured. They are out of work. They may not be receiving any money, or they may not be receiving the correct amount.
They may not have enough money to pay their rent or put food on the table.
They are in pain.
They may not be receiving the medical treatment they need.
Our paralegals and other team members listen to all of that. They want to help.
But if you are a person without professional training in processing trauma, how are you supposed to absorb these stories every day without allowing them to affect you?
That is something I think law firms need to take seriously.
We bring in psychologists and other trainers regularly to help our team understand how to process the trauma they hear from clients without internalizing it themselves.
We also provide ongoing education and training.
We have Wellness Wednesdays, where we might do something as simple as a ten-minute meditation. People can participate if they want to.
A lot of my team members are young. Some are in their early twenties.
Suddenly, they are hearing very intense stories from people dealing with pain, financial stress, disability, and loss.
They may not yet have the life experience or coping mechanisms to know what to do with all of that.
Mental health can easily be taken for granted.
I think we have a responsibility to give people tools to process what they are experiencing.
Julia: What advice would you give someone who is considering starting their own firm?
Mary Ellen: It is a lot of work.
There is no question about that.
But one thing that has probably helped me throughout my career is that I tend to plow through things without overthinking them.
I am not paralyzed by perfection, and I am not paralyzed by planning.
Sometimes my attitude is simply, “Okay, let’s do it and see what happens.”
If it does not work out, I can always go work for someone else.
That is something I would encourage people to remember when they are considering opening their own business.
Ask yourself: What is the worst thing that happens?
Maybe it does not work.
You put your résumé together and find another job.
Obviously, there are financial realities involved. Starting a firm can be expensive.
I would avoid taking on unnecessary debt if you can.
I was very fortunate because I could perform per diem work for an insurance company while building my practice. If you are in an area where you can do court appearances, contract work, or other per diem work while developing your own clientele, I highly recommend it.
Having cash flow during those early stages can make a tremendous difference.
To the extent possible, I would also limit how much money you borrow at the beginning.
Give yourself room to try.
And remember that deciding something is not for you does not mean you failed.
Julia: You have spoken about the importance of being willing to change direction. Where does that philosophy come from?
Mary Ellen: One of my children was pursuing a Ph.D. and eventually realized that the career path was not what she actually wanted.
She was afraid that leaving the Ph.D. program would mean she had failed.
I told her the opposite.
Spending six years completing and paying for a program when you already know it is not what you want is not success.
Sometimes the successful decision is recognizing that something is not right for you, leaving it, and following another path.
It was good that she tried because otherwise she might have spent her entire life wondering whether that was what she wanted.
The same is true when starting a law firm.
If you open a practice and discover that ownership is not for you, that does not mean you failed.
You tried it. You learned from it. Now you know.
The failure would be never trying because you were afraid of what might happen.
No matter what happens, you will develop skills from the experience that you can carry into whatever path you choose next.
Julia: Is there any career advice that has stayed with you throughout the years?
Mary Ellen: Steve, the CEO I worked for at the insurance company, told me something I still think about: “Never go back in your career.”
I think there is a lot of truth in that.
Sometimes we want to go backward because something feels comfortable or familiar.
That does not mean you can never return to the same company.
But if you left as an associate and eventually return, return as a senior associate. Come back in a different capacity. Take what you learned and use it to move forward.
I have seen people leave jobs, try something different, and then return to exactly the role they previously had. Often, it does not work as well as they imagined it would.
Of course there are exceptions.
But as a general principle, I think you should always try to keep progressing.
You may change direction. You may pivot completely.
Just do not confuse moving in a different direction with moving backward.
Keep learning, keep building your skills, and keep moving forward.
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