Live Like You’re Dying, Maximizing Risk-Adjusted Returns

In my over two decades of managing money, I have noticed parallels between key money management principles and life management strategies. As a bond manager, an angel investor and now treasurer of a tech venture capital group, I have seen my fair share of economic, security and corporate implosions.

Experienced investors know that crisis is inevitable; we just don’t know when or how it will unfold. The same is true in life. In the recesses of our minds, we all know we will die — we just don’t know how or when death will beckon us or our loved ones. Two recent personal tragedies this past quarter have compelled me to reflect, share and write about how the strategies I used to prepare for and manage financial crises are also applicable to preparing for and managing life crises.

Experienced investors know that crisis is inevitable; we just don’t know when or how it will unfold. The same is true in life. In the recesses of our minds, we all know we will die — we just don’t know how or when death will beckon us or our loved ones.

Alan Braxton, a childhood schoolmate and friend, started feeling weak while playing tennis with his daughter. It turned out he had a cancerous tumor the size of a grapefruit in his stomach. After his diagnosis, Alan used to joke with close friends that the trees seemed more vibrant green and his favorite soft drink tastes extra sweet. Although doctors successfully excised the initial tumor, the cancer returned with new tumors growing in after successive surgeries. The procedures led to scarring that precluded future operations. Alan and his wife, Deborah, decided to forgo additional chemotherapy and focus on his quality of life. Alan passed away one month later.


I co-hosted a women’s retreat for asset management where I reconnected with an effervescent young woman whose enthusiasm and zest for realizing her dreams was infectious. Tanji Dewsberry was a fellow financier and 37-year-old single mother of a 10-year-old son who aspired to write a children’s book and become an entrepreneur — goals that she eventually accomplished. One of the younger members of this retreat, Tanji’s enthusiasm and drive quickly endeared her to the entire group. This past April, an electrical short in the walls of her home smoldered and ignited in her son’s bedroom. Presumably attempting to save him, Tanji went into his room, where firefighters later found them both deceased. Tanji and her son had no warning of their demise.


While the context of these deaths varies, one unifying lesson binds them. The same way a market can crash in an instant, life can be taken away in a moment. Neither Alan or Tanji could have predicted their fates. These experiences reminded me that life is a fragile gift and is one worth both treasuring and protecting. Inspired by these experiences, I surveyed individuals, asking, “What would you do if, God forbid, you knew you had only two years to live?”

I heard:

“I would never get angry or have a heated argument with my wife again.”

“I’d spend more time with my family.”

“I’d take more risk doing what I really wanted to do.”

“I’d travel to places I’ve always wanted to see.”

“I’d have much less stress and more clarity about what really matters in life.”

“I’d let those who really matter to me know.”

“I’d videotape key, personalized messages I want each of my children and loved ones to hear after I’m gone. I’d finalize my will and share values I’d want to impart.”

The more I listened to what people shared and reflected on my losses of this past quarter the more I wondered, “Why wait until for bad news to start living fully?”

Despite death’s irrevocable certainty, it still holds the power to take us by surprise. I am reminded of two things. First, I think of the song, “Live Like You Were Dying.” This phrase might sound like a call to live recklessly. I see it, instead, as a call to cherish life and take full advantage of what you can create and what life has to offer while being aware of the risk and inevitability of death. While it may initially seem like an odd parallel, the spirit of these lyrics mirrors my clients’ money management mandate, “Deliver attractive risk-adjusted returns.” This mandate essentially means that money managers are supposed to maximize their returns while accounting for inherent portfolio management risks. A portfolio’s loss can obviously never compare to a personal life loss, but similarities nevertheless exist. As a portfolio manager, I knew of the inevitability of things not going as hoped or planned; companies and securities I invested in could implode, and economies and or markets would falter at some point. In investor parlance, I had to generate attractive risk-adjusted returns, constructing portfolios poised for the upside but use strategies to protect portfolios from downsides.

The more I listened to what people shared and reflected on my losses of this past quarter the more I wondered, “Why wait until for bad news to start living fully?”

How can we focus on the best of life while planning for the worst of life? There are many ways to prepare for life’s pitfalls. For example, an individual can save enough financially for not only a rainy day but also for a rainy season. This might include securing adequate insurance, summarizing your finances for loved ones, creating an ample financial cushion and/or personally creating both a basic and living will. In the personal sphere, being prepared could mean telling those you love how you feel, apologizing to anyone you’ve hurt, reaching closure with any unfinished business or writing letters for loved ones.

While preparing for life’s downsides, add value to your life by creating your upside. Alan taught me that we all can discover how to appreciate life’s simple things. I learned from Tanji’s story to act now and not put off until later what we can do today. Their legacy has led me to fully appreciate and advocate and to practice living more fully each day. Today, we can love freely and unconditionally. We can choose to let go of resentments. We can take the time and effort to create special moments. We can forgive; lead with love; live each day fully and joyfully. We can give and serve in ways that really matter.

One strategy that can enhance your own personal portfolio and maximize personal returns includes taking care of and investing in yourself first so that you can then take care of and invest in others from a position of strength. One way that I invest in myself is getting adequate sleep and exercise. These practices give me energy to be the mom, the significant other and the friend, that I want to be. It fills my personal well. Another strategy you can use to enhance your personal portfolio is to engage in activities that better the lives of your loved ones and your community. Ultimately, you will reap the greatest returns from aligning your actions with your core values and doing what is in your heart. Do what you love and love what you do.

One strategy that can enhance your own personal portfolio and maximize personal returns includes taking care of and investing in yourself first so that you can then take care of and invest in others from a position of strength.

At the center of both financial and personal returns are you and your choices. So until that day when you leave this world, keep in mind what is important. Live like you are dying. Maximize your personal returns of happiness during your brief stint on earth. Don’t put it off until tomorrow. Start now. Choose joy.

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