Bennie figured he had just a few years left, although who knew? He counted every day as a blessing, especially as he felt his verve for life slowly decline and saw his health decline faster. Those declines, though, had him asking what am I leaving behind? Throughout his life, Bennie hadn’t thought much about his legacy. He instead just lived. But lately, he had been thinking about his impact and what he would leave behind. Bennie even wished he’d thought much earlier in his life about the legacy his life would leave. Yet regrets weren’t going to do anyone any good, Bennie figured. Instead, he decided to see what he could do to improve his legacy before it was too late. He only needed to know where to turn for help.

Advice

Advice is only good when you’re ready for it. And even then, some advice is good, other advice is better, and some advice is no good at all. The thing about advice isn’t so much its author. You can have all the experience and skill you wish but still make a mess of things when giving others advice. Don’t listen to someone just because they’ve been around the block. They may have missed a few things that they should have noticed along the way. When you finally open your eyes to see that you could maybe use a little help, a little strategic advice, maybe a little nudge here or there, don’t trust everything you hear. Blind trust may have been what left you short of your goal, missing out on important things. Instead, evaluate the advice you hear. Let the advice you hear work its way through the filter of your own experience. 

Humility

Especially filter the advice that you hear through your experiences where you realize now that you fell short. Failure, faults, and shortcomings are fabulous filters, when you know that they’re there. When you have the humility to see how poorly or inadequately you handled a responsibility or opportunity is when you’re ready to change. Honest humility is a powerful stance. Real humility is not denigrating oneself just to look and feel better. Authentic humility trusts more in the truth than in oneself. That’s what makes it so powerful: honest humility is the lens of truth. Honest humility won’t accept sugar coating faults or buttering up. So as you read this strategic advice, thinking about what you want your legacy to be, keep humbly in mind what your legacy just might be if you don’t adjust course a little. Think, in other words, about what you don’t want your legacy to be. Filter this advice through your shortcomings and faults. If you do so, you just might be able to make those necessary or helpful adjustments to burnish your legacy.

Retrospective

See, a reliable guide doesn’t just show you what’s ahead. A good guide also helps you see what you’re leaving behind. Guides don’t just scout where you’re headed; they also frequently look back. Only by looking at the ground you’ve already covered can you ensure that you’re adjusting your heading toward meeting your mark. If you’ve leaned a little too heavily into earning a living, and finances are secure but relationships are tenuous, maybe you need to adjust. If instead you’ve been tending the home fires nicely but not keeping the pantry stocked, then maybe you need to put in a little more effort bringing home the bacon. Don’t know your neighbors? Maybe it’s time you took a slow stroll around the block. Disconnected from your community? Maybe it’s time you look for a local problem you could address or cause you could serve. Even caring adequately for your own health can be a legacy issue, if you hope to be a good model and not be too great a burden in your later years. So, maybe it’s time for some disciplined adjustments to your diet and exercise. A good guide helps you take a look back to assess the direction you need to be heading.

Time

Time is an agent of change, both for good and bad. Your legacy is a product of your stance’s interaction with time’s agent of change. Legacy involves taking a stance. Do you love your spouse and children? If so, then stand on it every waking moment of your life, and love will be your legacy. Do you care for others in your community? If so, then stand ready to recognize and serve their needs, and that will be the legacy you leave. Do you believe in your efficacy in the world, that you can make a positive difference? If so, then gird yourself for the battles that chaos will bring against you, saying that you can’t. To shape your legacy, you don’t need so much to dream up a grand vision like the world’s never seen. If you can, then do so. But your legacy might then be as a dreamer of foolish visions. Instead, let the change agent of time bring your vision to you, if you first adopt the bold and righteous stance. Your vision arises at the intersection of your stance and the potential that time’s chaos brings to you. Let time do the work. You take the stance. 

Stance

The right stance is what a good guide shows you. The guide doesn’t know what’s coming from around the next bend, whether a mother bear protecting her cubs hidden beside the path or a spectacular sunset to capture with your camera. Yet a good guide can show you how to be ready with both the courage to confront the bear and wonder to take the sunset snapshot. You can’t create a legacy in an instant, although instants can shape your course. A legacy requires having a consistent response to the day’s maelstrom. We could call it character, but character is more a product of your stance than its generator. Or the two, character and how you approach things coming your way down the path, go hand in hand, one feeding and shaping the other. A guide, though, can’t really change your character. But a guide can show you a good stance to take that, held long and firmly enough, can give you good character. And good character exhibited enduringly across one’s life is what shapes a legacy. So, start with the right stance.

Fruits

By their fruits you shall know them. Don’t follow anyone who is not leaving a sound legacy behind. Don’t follow a guide who’s already led a few parties over the cliff and into the canyon far below. Listen to those who have the respect of their families, employers, neighbors, and communities, those who look most likely to leave behind their own rich rather than meager legacy. Indeed, look around you at the individuals and types who seem to bear the most fruit in authentic goods, not the virtue signaling of moral language but the evidence of a well-lived life. Those fruits for which to look, as evidence of a reliable guide, may be long, close, supportive, and stable relationships, many hope-filled and healthy grandchildren, hundreds of well-educated and appreciative graduates, or thousands of appreciative patients or clients. The fruit that will lead you to a reliable guide may be an otherworldly peace you notice your guide maintaining in the midst of a storm or an otherworldly insight your guide has into the mortal soul. Judge the advice you receive not just by how it resonates with your own experience, especially in revealing your own self-admitted faults, but also by the fruit borne by the one who offers the advice.

Experience

That your guide has significant relevant experience can also help. My advantage in accumulating experience from which to draw strategic insights has to do not so much with my own long, varied, and richly challenging and rewarding life. My advantage has more to do with the lives of others I’ve observed up close along my way. In my young life, I traveled the country as a horse trainer, which taught me a lot about the ambitions and opportunities of both rich and poor folks in different walks of life. But my nearly forty years as a lawyer truly pulled back the curtain on how life works in its greatest heights and depths. That in the course of those years I also had the privilege of teaching law to adult students of all ages, while leading two campuses for a decade and a half, gave me another broad and deep look into the richness, complexity, and opportunities of life. Charitable nonprofit leadership and representation, and pro bono service to a few thousand homeless and disadvantaged clients, further broadened my picture. This guide doesn’t share the dozens of client stories that continue to inform me. It instead shares the accumulated insight.

Care

The other thing you need from a guide, beyond the ability to look both forward and back in humility, help you form a sound stance, and show you the fruits you should expect of wisdom, is for your guide to care about you. Just to care. Obviously, don’t listen to advice from people who hate you. They’re plotting your demise. Yet also don’t listen to advice from people who don’t care about you either way. They’re just entertaining themselves, maybe making themselves feel better about their own regrets. And beware advice from those who have financial interests to pursue. Conflicts of interest shape advice. Consider the incentives and disincentives surrounding the advice of your physician, financial advisor, lawyer, plumber, grocer, real estate agent, and, well, you name it. They may all care deeply about you, but then again a few of them may not. Find those people who care about you most, and listen to their advice. They may not always be right, but at least they’ll have your interests at heart.

Commitment

My commitment to you in this guide is to care about you. I have nothing else to gain but to care. That commitment to care is why I’ve been writing this series of Help with Your books addressing jobs, careers, marriage, divorce, money, faith business, nonprofits, and other subjects. The advice these books share aren’t tricks and tips so much as just sound and largely traditional advice, although strategic advice pointing toward deeper goals. You can get through life without taking much of a look at it. You can follow the crowd, and the crowd will take you where crowds go. But you may instead have reached the point in your life where you want to be sure that you’re headed where you should go, a place that may be much higher, richer, more meaningful, better, and more satisfying than the places where uncaring crowds will take you. Come along on the journey. You can see a long way and get a great perspective from those high places the journey will help you reach.

Reflection

What makes you interested in shaping your legacy for the better? Do you believe that you have the time and ability to do so? Are you humble enough to accept some advice on improving your legacy? Do you feel that looking back over your life may help you look forward to leaving a stronger legacy? Do you wake up each day in the right mood and with the right stance to improve your legacy? Think of those you know who look most likely to leave a strongly positive legacy. What fruits do you see in their lives that makes you think of them as oriented toward their legacy? Whom do you know in your wider circle of acquaintances who has such substantial life experience as to have the wisdom and discernment about how to shape a legacy? Who cares about you deeply enough to offer you sound suggestions on improving your legacy? 

Key Points

• You must be ready for advice if advice is going to make any difference.

• A little humility goes a long way when seeking advice on your legacy.

• Looking back over your life can help you look forward to your legacy.

• Time will bring you all the opportunities you need to shape a legacy.

• Get in the right stance toward your legacy, and you’ll likely shape it.

• Take advice from those who produce the fruits to prove its value.

• Take advice from those who have the rich experience to offer it.

• Take advice only from those who care about you, not the heartless.

Read Chapter 2.