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  • Writer's pictureHannah Boundy, CFA®, CFP®

Five Ways to Live Your Legacy While You’re Still Working

Updated: Jan 10, 2023

When building a living legacy, many people don’t realize that the preparation involves more than saving and investing to build a sizeable portfolio. An equally important aspect of crafting a living legacy is refining the habits, intentions, and values that will define your living legacy in retirement. One of the best ways to do that is to begin living your legacy right now. This doesn’t mean you quit your job and retire immediately. But it may mean exploring what it looks like to spend intentionally, brainstorming what is important to you and how you might want to express that with your spending, and discussing with your family how they might also participate. Below are five ways to live your legacy now while you’re still working in preparation for living your financial legacy in retirement.

Practice Saving and Spending (Everything in Moderation!)

When it comes to financial planning, one of the common things we see as advisors is that people are either savers or spenders, but rarely both. Either, we’ll work with someone who has lived frugally all while diligently saving for the future, and when it comes time to retire, they don’t know how to flip the switch to spending and continue “saving” even when they’re done working. Alternatively, we may work with someone who loves spending and has struggled to save what they need to continue to spend in retirement. Sometimes the two are married, which creates a fun balance!

The point is, as with most things in life, it helps to view saving and spending in moderation. As you probably know, saving is key to attaining your financial goals. Adequate savings is what makes most retirement plans possible. However, saving for something you’re willing to spend on is also important. At some point, you have to ask yourself what you are saving for and when the time comes will you be able to permit yourself to enjoy the fruits of your hard work?

A straightforward way to practice this is to do it on a smaller scale. Set short-term savings goals for things you enjoy, such as a home improvement or vacation. Practice saving and spending in your day-to-day so that when the time comes to execute some of your goals on a larger scale, you can mentally flip the switch from saving to spending, in moderation, of course. Saving is an excellent habit, but we hate to see it wasted when the opportunity finally arrives to enjoy the result of all your saving.

Be Intentional with Your Spending

One of the best ways to learn how to spend well is to set intentional goals for spending. This is the opposite of impulsive spending in the line at the cash register. It is the antithesis of buying a pack of gum or a soda because it looks good at the moment. Intentional spending is also a great way to involve your loved ones in your financial legacy. It may look like gathering everyone together and planning a memorable family vacation with the express purpose of spending time together. As you save for this goal, your intention to create memories becomes part of what you’re saving for, just as much as for plane tickets or a week at a resort. Intentionality is a crucial aspect of crafting a living legacy, and practicing intentional spending is a great way to explore what you may want your legacy to look like.

Brainstorm (and Take Notes)

Another common experience we have as advisors is working with a client who has been so focused on saving for their retirement that they haven’t considered what it could look like and what they might want to do once they’re done working. Don’t wait until it’s time to retire to think about what’s important to you and how you may want to spend the latter part of your life. At any given moment, we are crafting our values and shaping what’s important to us in how we live and spend our time and money. Unfortunately, when we aren’t actively defining those things, it’s easy for them to be determined for us instead of being decided by us.

In my family, we sit down at least annually to talk about the important things and how we realize those values in our lives. One such item is generosity and charitable giving. Every December, our family gathers to look at our giving and discuss how we’re being intentional with our resources in pursuit of living generously. We then brainstorm where else we can give and how we might want to engage in that family value in the coming year. We will also write down our ideas, so we don’t lose them in the chaos of the day-to-day when we walk away from the conversation. Taking time to think about the legacy you want to live is just as important as living it, and writing it down so you can return to your thoughts later will help you stay attuned to those values and goals.

Engage with Your Loved Ones

Another common theme we see when helping clients plan their living legacy is wanting their families to be a part of it. The easiest way to incorporate your family into your living legacy is to engage with them while you’re still working. One of the greatest disservices we can do to our families and ourselves is failing to talk about money and values early. When we don’t talk about important topics early and often, it makes it much harder to have those conversations later on. That doesn’t mean it will be easy or feel natural.

I’ve learned from talking about our finances in my own family that it takes time to create a common language around money. Especially early on in my marriage, I can recall having conversations with my spouse about how we wanted to structure our finances. These conversations often ended poorly because we weren’t familiar with how the other person viewed money and the words they used to describe it. My spouse would make a statement that meant one thing to him but that I heard differently. Over time, we worked to define how we collectively spoke about our resources and values, and our conversations have become much more productive.

Meet With a Professional

The number one obstacle clients have to living their legacy; both now and later, is not knowing if they can. When we talk about financially living out our values, we’re often referring to the upper levels of Maslow’s Hierarchy of needs – things like spending for connection and community, status and recognition, and ultimately for self-actualization. But before spending on those things, we need to know that we will be ok. We need to know that we’re not jeopardizing our safety and security. This is the great balancing act that we’re all trying to achieve. We want to know that we’re saving enough to safely and successfully retire but at the same time enjoy our time on earth now because we know the future isn’t promised to us.

For us, this is a monumental question and one best answered through financial planning. Digging into the details and doing the math allows us to understand better if we’re saving enough and what we can afford to spend in pursuit of our values in the present. If having that analysis is something that appeals to you, we’d love to talk. You can schedule an introductory call with one of our advisors today and take the first step in crafting and practicing your living legacy, even while you’re still working.


Sherwood Financial Partners, LLC is a registered investment adviser. Sherwood Financial Partners, LLC may only transact business in those states in which it is registered, or qualifies for an exemption or exclusion from registration requirements. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and, unless otherwise stated, are not guaranteed. The information contained herein is not intended to convey or constitute legal or tax advice. Be sure to first consult with a qualified financial adviser, legal professional, and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance. Principal value and investment return will fluctuate. There are no implied guarantees or assurances that the target returns will be achieved or objectives will be met. Future returns may differ significantly from past returns due to many different factors. Investments involve risk and the possibility of loss of principal.


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