Live Like You Were Dying

Important lessons that underlie Tim McGraw’s song title


Yes, I’m a Tim McGraw country music fan. And though I think he might be considered old-school country music, when we unpack the subject of planning for our legacy, we conclude with the idea that we must first face our own mortality. What is it that we really want out of our lives? What purpose or cause are we excited about? What will we look back on at our end that will have truly brought us joy and fulfilment?

One of my favorite sayings is, “Begin with the end in mind.” I don’t know who said it first, but I know it’s the premise of the book “The Seven Habits of Highly Effective People” written by Stephen Covey. When we begin with the end in mind, i.e., our own mortality, it gives us better perspective and context around the decisions we make today. It stimulates our passion and urgency to impact those around us in a positive way. It also enlightens us as to what values we would like to pass on to our children.

I turn fifty years old this July 2024, and I'm starting to feel a sense of urgency about what I am passing on to the next generation. Don’t get me wrong, I’m not concerned as much about how my children will handle gobs of money when I die (not yet anyway!). On the other hand, I’m more concerned about setting them up for success and not passing on certain dysfunctions I have battled through in my life.

I want my kids to be more secure in who they are than I was. I want them to know that in all situations, they are worthy, they are loved, and they are valued. You might say, these are our family values that I want to be intentional about passing on. Furthermore, I sincerely believe that I may have been a better military and commercial-airline pilot if those values had been part of my natural identity from the start. When I think about creating my family, or community legacy, these are the things I think about.

This is an article about money and finances, so how do our values fit or apply to passing on wealth? My answer to that question is this; if all I do is pass on financial wealth, there is a good chance my money may do more harm than good if the values I believe in are not also part of my legacy. In essence, if I only pass on money to the next generation, I may actually set them up for failure.

Passing on character, values AND financial wealth is a very difficult thing to do. In fact, most millionaires in the United States are first-generation millionaires. In a recent article in Business News Daily, author Stella Morrison says it this way, “… around 68 percent of those with a net worth of $30 million or more made it themselves. Further, a second study by Fidelity investments found that 88% of all millionaires are self-made, meaning they did not inherit their wealth.”

Let’s face it, airline pilots are earning more money now than ever. Many of you will be able to pass on significant wealth to the next generation and/or causes you care about. Furthermore, you will leave a legacy whether you know it or not, whether it’s good or bad. Why not take the time to make it a good one? When you’re facing the end of your time on this Earth, what will you value the most? Allow those questions to guide your life right now.

Below are some practical steps and points to ponder to help you begin to think about how to proactively design your life and legacy. Think of it this way; if you don’t take the time to be intentional about your plans, the future is coming and what happens (without your planning) you may not like!

Define the problem

You work your butt off to create income, wealth and a good life. But your children probably didn’t see you overcome the obstacles and the challenges it took to get where you are. Money is not like other areas of our lives where we can expect our kids to pick up on our good habits and characteristics without significant effort and intentionality.

The other day. I asked a friend of mine how his son became interested in the weightlifting team at his high school. He shrugged his shoulders and commented that his son must have been influenced by seeing him and his wife work out consistently over the years. Learning about money and personal finances, on the other hand, is very different. Often families have great money habits, but if these principles and habits are not clearly communicated, misperceptions can form. For example, “My parents don’t spend lavishly, therefore we must be broke.” In this example you may have excellent money habits but unless your money values and your intentions are clearly communicated you may unintentionally pass on an attitude of scarcity versus an attitude of abundance.

Three steps to consider if you want to be intentional about passing on your legacy

Your children may not see all the hard work and sacrifice you put in to become a high-income airline pilot. All they see is that you are home three to four days a week trying to catch up on house chores before you pack your bags again. (Admittedly, that’s not so bad … I like this airline stuff!)

1. Share your experiences, challenges and struggles with your loved ones.

Consider sharing more of your experiences with your family. At the appropriate time, discuss some of the challenges you overcame to become that highly skilled, highly sought after airline pilot. Your kids may scoff (mine just laugh) at you a little when you share but they will remember you struggled and overcame obstacles. Hopefully, when inevitable challenges come their way, they will remember that even you struggled at times, and you were able to overcome obstacles and achieve your goals. At least they will know enough to not expect the path to always be smooth.

Unfortunately, this means we must be a bit more vulnerable and open about some of our challenges. (Men, take particular note.) Personally, I like to make people think it was all a breeze. That would mean that I’m smarter, tougher, stronger than I really am. That’s not what our kids need to see.

2. Communicate with your spouse, significant other or trusted friends.

Often, we are creating a great legacy and positively influencing those around us without thinking about it. It may just come naturally to you. However, for the rest of us, the first step is to literally say it aloud. What is it you want? Bring the subconscious into the conscience by discussing it with someone. I often forget that my wife doesn’t know what’s on my mind or doesn’t know what I’m trying to accomplish by talking to our kids about “who they are.” 

Better yet, write it down. There is something very powerful that happens when you write down your goals, visions for your family or your family’s core values. If you google, “why is writing down my goals important,” you will get a slew of great articles about how you are 42 percent more likely to achieve your goals if you write them down.

One article from written by Peter Economy, The Leadership Guy says, “writing your goals down not only forces you to get clear on what, exactly, it is that you want to accomplish, but doing so plays a part in motivating you to complete the tasks necessary for your success. The process of putting your goals on paper will force you to strategize, to ask questions about your current progress, and to brainstorm your plan of attack.”

3. Write down what you want people to line up to thank you for on your death bed.

A little morbid – I know. However, let's just admit that we’re all going to die someday. And all the toys you’ve accumulated will not be on your mind when that time comes. What will be on your mind? What do you want your epitaph to say?

The next time you’re flying from New York to San Fransisco take some time to ponder what the top five things you want to say about yourself before you’re gone. Take some time to plan what you want to be remembered for, forever.

Write down what non-financial character traits and values you would like to see passed down for generations. Is it your faith? Is it something specific to your family, such as an attitude of service before self or leadership. Be intentional and plant the seeds now.

In closing, here are a few of the values we are trying to pass on to our young children.

  1.  An attitude of stewardship versus an attitude of ownership. In other words, we’ve been blessed with something (money, health, relationships) and it is our responsibility to take care of them, nurture them and hopefully bless others along the way.
  2. Attitude of generosity. Study after study shows that giving makes us happy. That’s all there is to it, so help them build habits of generosity now.  
  3. An attitude of abundance versus scarcity. I believe if our kids are secure in who they are, they will not feel the need to get more for themselves at the expense of someone else.
  4. An attitude of ownership and responsibility. We want to teach our kids that it’s okay to make a mistake or even fail at something. It’s part of the growth process. I want my kids to know they can fail and overcome the situation or face the consequences and it’s okay. If we shortcut or insulate the struggles our kids may face or go through, we cheat them out of the opportunity to find out what they really want and what they are willing to do to get it.

Finally, what we do now will impact multiple generations, possibly hundreds of years. Passing on financial wealth is the easiest form of capital to pass on, but it can be the most destructive if we haven’t prepared the next generation to handle the responsibility of wealth.

Hopefully, you found this article interesting and helpful. If you have any questions, contact us at 865-240-2292 or [email protected]. Also, please tell us if we can help you on your journey to financial peace and prosperity! Click here to sign up for our newsletter or click here to schedule some time to chat about your circumstances in more detail. Also, check out our Pilot Money Guys podcast where we regularly discuss these types of financial topics along with some fun airline news updates and interesting guest interviews — even with the editor and founder of Aero Crew News – Craig Pieper!

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Charlie Mattingly, a CERTIFIED FINANCIAL PLANNER™ professional, is a first officer for one of the "big 4 airlines," based in Atlanta. Charlie and his team of dedicated professionals specialize in helping pilots create, grow and protect their wealth so they can have as much fun in retirement as they did flying airplanes for a living. Originally from Louisville, Kentucky, Charlie earned his Bachelor of Science degree in Mechanical Engineering from the University of Tennessee in 1997. He then served with the United States Air Force for ten years as an officer and F-16 fighter pilot. While serving in the Air Force, Charlie shared his passion for personal financial planning by administering Dave Ramsey’s Financial Peace University to his fellow military servicemen and women. After the Air Force, Charlie wanted to begin a new career helping others understand and thrive in personal finance which drove him to earn his MBA in Financial Planning from California Lutheran University. Charlie also received the CERTIFIED FINANCIAL PLANNER™ (CFP®) professional designation in 2012. Charlie’s passion is to understand each client’s unique situation and their family’s goals and dreams for the future. His objective is to take the worry out of personal finance. He works hard to be worthy of his clients’ trust, providing absolute transparency, a high level of integrity and objective advice. Charlie believes his prior life and work experiences as an Air Force officer and pilot have helped him understand the discipline, knowledge and leadership it takes to be an effective financial advisor for his clients. Charlie was hired by the airlines in 2007 and is fortunate to have the flexibility to continue to fly for the same company today. Charlie commutes to Atlanta from his home in Maryville, Tennessee where he enjoys spending time with his wife Leisa and their three beautiful girls Emma, MaryJo and Ellison. In his spare time, Charlie loves to read, play golf and even sometimes pretends to be a horse farmer!


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