Why Estate Planning Feels Intimidating and What To Do About it

By Kristen Heaney

If you’ve ever sat through an estate planning meeting and left feeling like you just left a foreign language class (only to immediately forget half of what you heard) you are not alone.

For people with significant resources, estate planning isn’t just about writing a will. It’s a series of weighty decisions:

• Who should raise your kids if something happens to you? 
• Should your assets be held in individual trusts or one large family trust?
• What powers should your trustee have, and who should that even be?
• How and when should you utilize your lifetime gift and estate tax exemption to pass assets to the next generation?

These are tough, high-stakes choices and unfortunately many people end up making these decisions before they truly understand the implications of their choices and how they align with their deeper values and intentions. 

The Technical Fog

Lawyers and advisors want to make sure your estate is tax-efficient and legally sound, but somewhere between “grantor retained annuity trust” and “dynasty trust,” a lot of folks’ eyes start to glaze over. They nod along politely, maybe ask a few questions, but often walk out feeling more overwhelmed than empowered.

And that’s when one of two things tends to happen - Either people delay, intended to return to the process when they get more clarity…which is unlikely to happen. Or they sign off on plans that sound reasonable on paper but aren’t fully aligned with their family culture or personal values.

Neither of these options serves the family well.

And in the best case scenario, families do make plans aligned with their values and intentions, but the plans are so complex they can’t explain or understand any of it in time. 

Why It Matters

Estate plans aren’t just legal documents. They’re blueprints for the future that shape the experiences of your heirs, influence their sense of independence or entitlement, and affect how your family relates to money, and to each other, for generations.

So when a family sets up a plan where each heir gets an equal share, large distribution at age 25, but they actually believe in delayed gratification and retaining the wealth across multiple generations, there’s a disconnect. Or when a well-intentioned parent puts everything into a single family trust to promote unity, but hasn’t prepared the heirs or the trustee to navigate decision-making with so many beneficiaries, chaos ensues.

There Has to Be a Better Way

And there is. It starts with slowing down the rush to strategy and making space to ask a different set of questions first:

• What kind of relationships do we want to preserve or build in our family?
• How do we define the intended purposes of our resources and how can the terms of our trust reflect these intentions?
• What messages do we want our estate plan to send?
• How do we want to prepare our heirs for these realities?

Once those values are clear, then you can move into the design phase of planning, ideally with an advisor or coach who speaks fluent “technical” but can also translate and guide the conversation back to what really matters.

Bottom Line

If estate planning has left your head spinning, you’re not broken, stupid, or disinterested. 

You just need a bit more time to: 

• LEARN - give yourself time to learn the language of trusts, tax, and estate planning outside of your attorney’s office. 
• CLARIFY - The intended purpose of your resources goes beyond being only legally sound or tax-optimized - spend time considering your values and wishes by doing some scenario planning given the trust terms you are considering. 

We’re here to help with both. Our Scholars program offers a fantastic route to building confidence for navigating all those pesky estate planning terms and our other peer groups and individual coaching can help you develop clarity on your intentions. 

Before you know it you’ll be ready to navigate estate planning decisions with confidence, knowing you’ve fully aligned your plans with your intentions and are ready for the future. 

You’ve got this!