Life planning peels back the layers of our soul, seeking the best and highest calling for our existence. Seek out a financial advisor who understands what you truly value and structures your finances accordingly to best support your life’s mission.

The idea is simple yet ingenious. Begin with the end in mind.

Let’s take another look at George Kinder’s well-known “three questions” that seek to uncover those goals and values most central in our lives. Number one is “If you had all the time or money you needed, what would you do?”

The response to this question typically provokes a long list of everything we want that money can buy. But with reflection, it goes deeper, stirring the longings of our heart.

The second question aims at these deeper desires. “What do you want to do or be so in the end you will feel that you’ve lived fully?”

These values most commonly revolve around three different realms. First, we yearn for meaningful connections with others starting with our immediate families and extending into our communities and the world at large. Second, we seek authentic spirituality, an odyssey that shapes and renews our very identity. And third, we revere beauty, creativity, nature and special locations. These three realms, righteousness, truth and beauty, are the areas where most of us find meaning and significance.

Kinder’s third question can be encapsulated by the phrase “Twenty-four hours to go.” It probes beyond our relationships and activities into the sum of our very existence. “Imagine that your doctor shocks you with the news that you only have 24 hours to live. Notice what feelings arise as you confront your very real mortality. Ask yourself: What did you miss? Who did you not get to be? What did you not get to do?”

This is a daunting question for many of us to even contemplate. Every day we get up preoccupied only with our to-do list, assuming we always have tomorrow. One day we won’t have tomorrow. We all know intellectually that day will come, but we don’t want to make our plans in light of it.

It is especially difficult to face our own mortality if we have not taken the time to deal openly and honestly with the issues in the first two questions. These three questions must be taken in order. We all want to perceive our lives as successful and significant. But justifying our existence is a daunting challenge.

Every day we face the dual desire to improve the world or to enjoy it. One requires judgment; the other, contentment. We struggle between the duty to do what we should and the passion to do what we love. The first structures our lives and the second strengthens and nurtures us. The consequences of these decisions are not always easy to understand because we must live our lives going forward. Kinder’s third question gives us the opportunity to stop and look back, to assess how our decisions have changed the course of our life if our life were to end tomorrow.

How do you want to be remembered by your friends and family? Author Samuel Butler wrote, “Life is like playing a violin in public and learning the instrument as one goes on.” Our faults are often embarrassingly obvious and humbling. First we have to learn to play the instrument. Then we need to learn to make our own music. At every moment we can confront our own mortality and reflect on the progress we have made.

Surveys have found that people regret what they didn’t do more often than what they did. And when people express remorse about having done something wrong, it was usually what I call a “life buster”–one of those decisions that can greatly compromise your life.

Serious life regrets include marrying someone you knew wasn’t right for you, getting hooked on drugs or breaking the law. You can recover from these, but you will lament the spiritual death and wasted opportunities along the way. A good rule of thumb is always to ask, “What’s the worst that could happen?” If it might destroy your life, hesitancy is indeed a virtue.

Regrets about things we didn’t do are more subtle. Our lives can change course dramatically and be filled with serendipity all because of some small decision on our part. How many times have we heard the story of how a happily married couple met, only to be surprised that it almost didn’t happen? If the worst outcome of a decision is a little embarrassment, perhaps the chance is worth taking.

We each long to participate in something significant. And that requires foresight, planning and forgoing our momentary desires in order to work toward realizing our greater passions. The choices we make each day determine the ones we will have the opportunity to make in the future. Without those hesitant, often stumbling first steps, we can’t complete the journey.

The Latin phrase “Audaces fortuna iuvat” translates as “Fortune favors the bold.” We commonly use a milder version of it in our family: “You do not have because you do not ask.” Often our hopes and dreams are unrealized because they are left unmentioned.

Voicing what we are passionate about can be scary. Beginning to act on our ideas can feel overwhelming. But courage isn’t a lack of fear, it’s action in spite of fear. And our fear may an indication that we are on the quest of our lives.

For entrepreneurs, overcoming fear is a regular occurrence. Many, perhaps even most, multimillionaires have at least one if not more failed businesses in their past. That’s because only those willing to risk failure–and the lessons learned from it–have the grit to achieve success.

Entrepreneurship, or its equivalent, is a form of proactive living. You don’t necessarily have to start a business, but you do have to begin the journey toward your life’s goal. When you take ownership of your life, you can do what you think is best, go where you think you are called and be who you believe you should be. Life can have fewer compromises and therefore fewer regrets.

I asked Kinder why he championed his three questions among financial advisors. He answered, “Money is the facilitator of what is most meaningful for us in the world. When we understand this, everything about money becomes clear and falls into place. We don’t hire a financial advisor just because they’re a nice person, they show us interesting spreadsheets, and they seem pretty much on the ball. We hire them so that with their professional financial expertise they can best deliver our brilliance into the world. Without being crystal clear what our most profound goals are, we can’t begin that process.”

A violin resonates because of the laws of physics. But virtuosos have to feel the music in their souls. Only after we know what we are striving to do with our lives can we make financial choices that enable and reflect our own special music.

Photo by Megan Marotta

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See Also:

• Life Planning Part 1: Plenty of Money
• Life Planning Part 2: Just a Few Years Left

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