How to Be a Successful and Happy Lawyer

This essay began as an ArbX talk I gave to young lawyers at the 2021 YSIAC Conference. It has since been revised and edited for clarity.

Throughout my career I’ve been blessed to have leaders, mentors and teachers who have taught me many valuable lessons. I’d like to share five of these lessons, framed by the proposition: “How to Be a Successful and Happy Lawyer.” Now, let me start by assuring you that this is not a contradiction in terms. Yes, it is possible to be both successful and happy as a lawyer. However, since we are lawyers after all, it’s critical that we first understand the definitions. What is “success”? What is “happiness”? According to the dictionary: Success - the achievement of a desired outcome or goal; Happiness - feeling happy, contented, satisfied, pleased. Both definitions refer to or hint at something outside of the definition, a point of reference. So if you want to be successful and happy, you first need to know what success and happiness mean to you. What is your “desired outcome”? What will make you feel “happy, contented, satisfied, pleased”? ?

Some might say the answer is found in money and material wealth: successful, happy people are rich. They are correct. To a point. Some studies have found that across the world, happiness and income are correlated up to a certain level of income; this is estimated at around SGD93,000 in Singapore and around USD80,000 in the United States. A more recent study looked at a different data set and concluded that there is an ongoing correlation between income and well-being even above this level, but that “the more people equated money and success, the lower their experienced well-being was on average”. And this was true even among high income earners: Rich people who equated money and success reported lower levels of well-being than rich people who didn’t. In other words, the more you think success is measured by money, the less likely you are to be happy.

This leads me to Lesson #1: Beware the golden handcuffs. I learned this lesson from a mentor I met in law school when I was a legal intern with International Justice Mission , a human rights organization started by lawyers to seek justice and restoration for the marginalized and oppressed. This mentor left a successful and very well-paid litigation career with a top US law firm to join IJM and rescue victims of sex trafficking and slavery, bringing their abusers to justice. She observed that many young lawyers found it hard to leave their law firms and pursue careers in public interest causes once they’d adjusted their lifestyles to match their large law firm paychecks (there’s a reason why Macklemore sang “If I'd had done it for the money I'd have been a f***ing lawyer”). I’ve met many lawyers who are unhappy or discontent with their jobs, yet they find it hard to leave because their lifestyles have become dependent on big paychecks. What about you? Do you know any lawyers who earn six or seven figure incomes yet seem unhappy or discontent with life? Any who aren’t happy but don’t want to leave their jobs because the money’s too good? Maybe money alone isn’t the answer.?

Others may say the answer to the question is found in professional accomplishment and recognition. Making partner, becoming general counsel, winning a “40 under 40” award or getting to the top of some publication’s ranking of your field. These are all what psychologists would consider “external validation”, affirmations that come from other people rather than “internal validation” that comes from within yourself. There is nothing intrinsically wrong with external validation. But it is risky to build your success and self-worth primarily on the validation and opinion of others that are subject to bias and often based on incomplete information, and that will change with time. There is also the very real risk that the people giving out these awards and validations are using flawed measures of success: Like someone trying to measure distance using gallons and litres, you may wake up one day and realize their way of measuring success doesn’t work for you.?

This leads to Lesson #2: Don’t accept someone else’s definition of success; find your own. I learned this from another law school mentor, a transgender Vietnam War veteran and a well-respected criminal defense lawyer and civil rights activist. My mentor never worked at a law firm, and she challenged me to question the conventional path to success that was laid out in law school. And while what I am about to describe is American in flavor, I suspect this is a fairly universal paradigm across the world: Do well in law school > Get an internship with a prestigious and well-paying law firm > Don’t mess up as an intern, get an offer to join the firm > Join the firm > Make partner (and a lot of money).

Don’t get me wrong, this is a fine path for some. It is also fine to start down this road to get experience, or to pay off student loans and establish a sound financial foundation before moving on to something else. But too many law students and young lawyers slog down this road because that’s what law school says they should do and they see everyone around them doing it, without stopping to think if it’s right for them. The result, which we are unfortunately too familiar with, is that they achieve “success” but do not find happiness. To solve this, we need to better understand what makes us happy.

Now, there are many ways to understand happiness, but let me share two concepts in contemporary psychology that are rooted in ancient Greek philosophy: Hedonism and Eudaimonia. The pursuit of pleasure, and the pursuit of a meaningful life.?

We are all hedonists. Allow me to clarify that in this context “hedonism” is not used with any negative connotations. Instead it encompasses a broad range of experiences and behaviors that bring pleasure, even altruism and helping others. The psychologist Abraham Maslow described a hierarchy of human needs, including some basic things that we all need to have some measure of happiness and satisfaction with life: food, rest, shelter, intimacy. Most of us would be miserable living as ascetic hermits shunning the basic creature comforts of life. But as Maslow’s hierarchy indicates, these aren’t sufficient. I won’t go into all of the higher needs in Maslow’s paradigm, but will simply observe that many of these higher needs are reliant on other people for their fulfillment, needs such as emotional intimacy, belonging, love. There is abundant scientific research that also demonstrates how helping other people is correlated with higher reported happiness and better mental and physical health. In No Exit, Jean-Paul Sartre observed that “hell is other people”, but perhaps heaven and happiness are too. So if you want to be happy, find pleasure in meeting your higher needs.

Eudaimonia is a Greek word that can be translated as the good life or the life worth living, and it is fundamental to happiness. Disclaimer (I am a lawyer after all): I am going to discuss eudaimonia in the context of contemporary psychology rather than Greek philosophy. And as such, while some philosophers argued (and still argue - after all we’re talking about philosophers) that eudaimonia and hedonism were at opposite ends of the spectrum, I believe that both co-exist as empirically important factors in our happiness.?In the context of psychology, eudaimonia means having a reason to get up in the morning, finding the value and purpose in your life that comes from knowing and pursuing what matters to you. If you don’t know this, then eudaimonia will elude you and so will a lasting and deep happiness that doesn’t depend on your circumstances and hedonistic experiences. Eudaimonia also provides the answer to the question implied in Lesson #2: How do you measure your own success? If you can find a reason to get up in the morning, an outcome to aim for that gives your life meaning, you’ll know what true success looks like.

Now, while this understanding of eudaimonia is subjective and will vary from person to person, not all meanings and purposes in life are of objectively equal value. Some meanings, some whys, will have more impact in the world and in the lives of the people around us. I would also observe that your why, your meaning, depends on your experience of life. Sometimes it takes cumulative experiences in life for us to find clarity of meaning. Sometimes it takes a personal encounter with or experience of a hardship, tragedy or injustice. If you’re reading this and wondering what is your why, don’t worry. It’s never too late to find it, and indeed what we find meaningful can and perhaps even ought to change over the course of our lives, just as we do.

?So what is your why? What matters to you, what gives your life meaning and purpose? What do you believe is worth fighting for? Once you know this, you will know what you must do to live your eudaimonia and find happiness. You might even make the world a better place as you do it.

Some Advice for the Journey

?Allow me to close by sharing some advice I received from other mentors. Regardless of what eudaimonia and success mean to you, this advice will help you get wherever it is that you want to go.

Lesson #3: Stay humble and curious, always. I learned this lesson from a partner at my old law firm who led his practice group and was a respected thought leader in his field. Even though he was an acclaimed expert in his field, he always remained humble, curious and grateful that his work gave him the opportunity to search for answers to complex and novel questions. I vividly recall walking with him to lunch one day while he gushed about a complicated question his client had posed and enthusiastically exclaimed, “Isn’t it great that we get paid to learn all this stuff??” No matter how much time we are given in life, no matter how much we learn, there is always something new to learn and to help us grow. And if we stay humble and curious, we’ll keep growing.

Lesson #4: Show up and be ready to help, day after day. The mentor who taught me this built her life and very successful career in Washington DC as a political staffer and ultimately a leading advocate on human rights policy and law. Drawing on her decades of experience through numerous political changes and working with politicians on both sides of the aisle, the timeless wisdom she shared was that it’s hard to get the right opportunities, and it’s even harder if you’re not there when they show up. And the only proven way to be there at the right time is to consistently show up. And if you want to get those opportunities that show up when you do, be interested in others’ work and ask if you can help. If you think your time is too valuable for you to be patient and wait, or if you think the work is beneath you, it’s unlikely that you’ll be there and called upon when the opportunities show up.

?The final lesson I’d like to share is the most important lesson of all, and it is one that I have learned from almost every single mentor and teacher in life.

?Lesson #5: People outlast the work. Be kind. Our work will change over time. Deals and cases will come and go. You might change your law firm, your area of practice or even your profession. But people outlast all of these changes. Clients on opposite sides of a bitter dispute today may one day become business partners, even friends. What about their lawyers? At the end of every matter you’ve worked on, will the other side be able to say that you treated them fairly and with dignity and respect? That you were kind and considerate of them as fellow human beings even while you staunchly advocated for your client’s interests? If they had to recommend counsel one day or had to engage counsel for themselves, would it be you? Let me be clear that this is not just a moral lesson but also a practical one. Behavioral scientists have found that reciprocity is a value hardwired into humanity across all cultures. We remember people who are kind to us and treat us well, and we seek to return their kindness. If you treat others well, especially those who don’t expect it, it will benefit you in turn. And it doesn’t take much. Simple courtesies can go a long way.

Thank you. I hope these lessons will help you on your journey towards success and happiness. I wish you all the best.