Why Estate Planning Is Easy and Legacy Planning Is Hard

Estate planning is easy. It’s finite, calculable.

What happens when you die? Who gets your stuff? How much will you owe in estate taxes and how can we prevent or prepare for it? You hire a lawyer to draft a will and possibly one or more trusts that provide for what happens when you die. It’s done. Complete.

You tuck your documents away in drawer or safety deposit box and sleep well at night, knowing you have taken care of your estate plan. Death is inevitable, so planning for it—while admittedly uncomfortable for some—is relatively easy. Life, on the other hand, is hard.

Estate planners may very well help you tidy up your affairs for when you die, but who is helping you with your life decisions? Who is helping you build the life you want to live and the estate and legacy you ultimately want to leave behind?


Humans are rational, thinking creatures. We have the unique ability to reason and not just react. The fundamental difference between us and any other species is our ability to make choices. Instinct, which is what the rest of all living beings rely upon, is the absence of choice: you eat because you are hungry; you flee because you sense danger.

Humans, on the other hand, can choose to act contrary to our instincts. We can decide to not eat, even though we are hungry. We can choose to walk down a dark alley despite our fears. In essence, our every movement can (and should) be intentional, as opposed to instinctual. We have the power to live by choice. We have the power to choose our life and direction, to write our own story.

The problem is, we are too focused on planning for the inevitable—for death—instead of planning for all of the uncertainty of life, and the choices we have the power to make.

How do you build the life you want to live and ultimately leave behind? How do you proactively live your legacy with intentionality and purpose? To start, you don’t do it alone.

Building a Legacy through Teamwork

It takes a village for you to build your best life—a team of professional advisers working daily and behind the scenes to help you achieve the life you want. You need a legacy team. Stop thinking you can run every aspect of your life, and admit that you need help.

While you may understand taxes and be able to prepare your own tax return, you simply do not have the time to be your own accountant and be your best self. You have to be in the business of being the best you and choosing the life you want to live. So, while you may be very intelligent, you cannot be your own team of advisors. Trying to will only cause you to lose control and revert to being instinctual. You will end up reacting to life, instead of intentionally living your life.

In addition to having a team, you need to understand that your life is a process, not a finite result. Who you are—your legacy—is ever evolving, and it is fueled by your daily choices. You need to wake up every day and be committed to living your legacy. It is not too dissimilar to going to the gym and staying healthy. The process must become routine. Much like meeting your personal trainer, your legacy team creates accountability. Ultimately, your legacy team will make you a better you.

The framework through which you and your legacy team operate is the beginning of your legacy plan. There are inevitable financial, legal and tax implications to your plan, but it is important to not simply react to those. While your legacy team may consist of various technical experts—e.g., legal, tax, financial, etc.—at the end of the day they should all be advisors, counseling you on how to make your best choices while navigating their particular area of expertise.

They should all be helping you plan for life, and all of its ugly challenges. That is a difficult and never-ending job. Planning (or not) for your inevitable death is easy. The question is: do you have the strength and willingness to plan for your life?

DISCLAIMER: The information contained in this article is for informational purposes only and is not intended, and must not be taken, as legal advice on any particular set of facts or circumstances. You need to contact a lawyer licensed in your jurisdiction for advice on specific legal issues.