What would be your biggest regret if this were the last day of your life? Stop reading for a moment, close your eyes, and pause to answer the question.

What is it?

The top regrets of the dying, as recorded by caregivers, include the following:

• I wish I had the courage to live a life true to myself, not the life others expected of me.

• I wish I hadn’t worked so hard.

• I wish I had the courage to express my feelings.

• I wish I had taken better care of myself.

• I wish I had let myself be happier.¹

Do any of these resonate with you?

Arguably, each of the regrets is a function of advancing toward the wrong goal line. Many times, it is only as people are dying that they finally discover that although they wanted to live a life true to themselves, instead they lived in accordance with someone else’s expectations.

I know this was true for me. For decades, I strove for the false metrics, was passive about my decision-making, and ignored my intuition. As a result, my work, my health, and my relationships suffered. I found myself further and further away from the life I wanted to live.

Does any of this sound familiar?

When I look at the list today, I can honestly say only one regret remains: “I wish I had the courage to express my feelings.” Like many lawyers, I am super skilled at thinking but not so great at being vulnerable. For many years, I hid my opinions and emotions from those in my ecosystem.

Not anymore.

I strongly believe the legal profession is at a critical inflection point. And I am on a mission to change the hearts and minds of lawyers. It’s an audacious goal because, let’s be honest, we’re a tough audience. So, what better way to get someone’s attention than to talk about the ultimate taboo topic – our own mortality.

Why This Matters

Lawyers and people generally in our western society have become exceptionally adept at avoiding existential queries because of the anxiety they produce. This fear often lulls us to ignore the reality of death, which can result in failing to make decisions that can protect or enhance our lives.²

Why talk about death to improve lawyer well-being? Because it is a progressive idea to accelerate change. We have come a long way from when I started practicing law in 1995. As a result of the groundbreaking Lawyer Well-Being Report issued by the American Bar Association (ABA), we can count the following wins: numerous firms have signed pledges of wellness, most states have created well-being task forces or commissions, law schools are incorporating wellness into curricula, and much more.³

But we are not moving fast enough. The legal profession is years behind corporations in integrating well-being as a standard part of work culture. And talk of well-being still raises eyebrows in some legal circles. Moreover, while lawyers are addressing many of the issues outlined in the report, we have not yet sufficiently tackled other stealth-like conditions such as burnout, health issues (for example, heart disease and autoimmune disorders, which are often related to or exacerbated by stress), or emotional strain that does not rise to a mental health diagnosis.

In my 20 years of experience as a lawyer and consultant, I have seen that my colleagues and clients are extremely successful at achieving what they think they want. But most of us are rarely honest about what we really desire. From the outside we possess the façade of happiness, health, and prosperity, but on the inside we can’t shake the sense that something is missing. To avoid dealing with these emotions, we compulsively throw ourselves into the comfortable distractions of work, technology, alcohol, drugs, or food. As we have seen from the state of our profession, this approach chips away at our energy, productivity, work quality, and physical and mental health. 

Thinking About Death Can Improve Well-being

Although death awareness can, on occasion, lead to negative outcomes, Dr. Kenneth Vail, a psychologist, and his colleagues conducted an analysis of studies and found that existential thinking can yield positive personal benefits.⁴ Here are a few:

It Motivates Us. When we begin to examine our life from the perspective of our deathbed, our sense of urgency around priorities shifts. Throughout history, philosophers, psychologists, and spiritual leaders have recommended keeping death in “conscious awareness” to remind us how short life is. This, in turn, motivates us to live as authentically and as fully as possible.⁵ As Steve Jobs put it in his address to Stanford graduates, “Death is … life’s change agent.”⁶ Developing our awareness around death “brings the scarcity of time front and center to our consciousness” and can empower us to act now to pursue our passions, realize our dreams, and do the things on our bucket list.⁷

It Improves Physical Health. An emerging body of research highlights the potential for death thoughts to encourage healthy behaviors and attitudes. For instance, conscious thoughts about death can spur increased “fitness and exercise intentions, reduce smoking intensity …, and increase intentions to use sunscreen.” One study found that “death reminders increased intentions to perform breast self-exams when women were exposed to information that linked the behavior to self-empowerment.” In short, the studies show that conscious thoughts about death can boost the desire to minimize “perceived vulnerabilities” and potentially lead to action and a change in mindset that advance physical health.⁸

[C]onscious thoughts about death can boost the desire to minimize ‘perceived vulnerabilities’ and potentially lead to action and a change in mindset that advance physical health.

It Makes Us Happier. In another study, a researcher asked participants to “write about death … each day for one week, or … just reply to specific questions such as: If you are aware life is short and that you could die sooner than you think, how does it make you feel and how does it impact you in general?” The study participants “report[ed] lower levels of depression, increased positive mood, increased self-esteem and increased intrinsic motivation.” The researcher further found that mildly depressed individuals benefitted most from a deep contemplation about death.⁹

It Helps Us Reprioritize Goals and Values. To paraphrase English writer Samuel Johnson, “When you know you’re to be hanged in a fortnight, it concentrates the mind wonderfully.” In other words, this type of awareness helps to acutely and immediately clarify our priorities and decisions and tunes out any extraneous noise.¹⁰ Conscious thoughts of death serve as an “awakening experience,” leading people to reexamine external goals related to status, money, and image and consider goals that are personally meaningful.¹¹

Now What?

Let’s go back to the question posed at the beginning. What was your answer? Now ask yourself:

• What is the first thing I can do to lessen the risk of having this regret?

• Do my current actions take me toward or away from my goals or values?

• What is something I have wanted to do but keep pushing to the future?

• What would I stop doing right now?

Write down your responses. Post them on your computer. Share them with a friend.

All this talk about death may seem like a radical way to discuss lawyer well-being. This article may encourage you or puzzle you. It may even make you irritated or angry. It is an uncomfortable topic. I get it. But my intention is that it inspires you or provokes you to inspire someone else you see suffering in silence. And maybe, just maybe, it could be another step in helping our profession become more civil, sustainable, and healthy.

As Steve Jobs said at the Stanford commencement: “[F]or the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.”¹²

If Steve Jobs did this, perhaps we can too.

» Cite this article: 94 Wis. Law. 51-53 (September 2021).

Endnotes

¹ Bronnie Ware, The Top Five Regrets of the Dying (Carlsbad, Calif.: Hay House Publishing 2012); see also Grace Bluerock, mindbodygreen, The 9 Most Common Regrets People Have At The End Of Life (Feb. 24, 2020).

² Irvin D. Yalom, Existential Psychotherapy (New York, NY: Basic Books 1980); see also Irvin D. Yalom, Staring at the Sun: Overcoming the Terror of Death (San Francisco: Jossey-Bass 2009).

³ https://lawyerwellbeing.net/.

⁴ Kenneth E. Vail et al., When Death is Good for Life: Considering the Positive Trajectories of Terror Management, Personality & Social Psych. Rev. 16(4), 303-29 (Nov. 2012). Note that while past research suggests that thinking about death is destructive and dangerous, fueling negative behaviors and attitudes such as racism, greed, and violence, more recent studies have shown that there are positive benefits to thinking about mortality.

⁵ See, for example, the writings of Friedrich Nietzsche, Thomas Merton, and Viktor Frankl.

⁶ See David M. Ewalt, Steve Jobs’ 2005 Stanford Commencement Address, Forbes (Oct. 5, 2011).

⁷ Sigal Samuel, The Surprising Benefits of Contemplating Your Death, Vox (Aug. 12, 2020).

⁸ Vail et al., supra note 4.

⁹ Nathan Heflick, Thinking About Death Can Make You Value Life More, The Conversation (April 11, 2014).

¹⁰ Gregg Levoy, The 5 Benefits of a Mortality Meditation, Part 1, Psych. Today (Feb. 24, 2016).

¹¹ Vail et al., supra note 4.

¹² Ewalt, supra note 6.