The Most Expensive Estate Planning Mistake Happens Ten Years Before The Estate Plan
TheShenkinLetter
Financial leadership · Board governance · The long game
Issue #4 · Month 2 ~7 min read
Board Governance · Leadership · Risk Oversight
01 The Big Idea
The Most Expensive Estate Planning Mistake Happens Ten Years Before The Estate Plan
Over the years, I've worked with hundreds of successful entrepreneurs, family businesses, and high-net-worth families.
One thing has always fascinated me.
The families that do the best job preserving wealth across generations rarely spend more time planning than everyone else.
They simply start earlier.
Most business owners understand the importance of estate planning.
They have wills.
They have trusts.
They have powers of attorney.
The documents exist.
What often doesn't exist is a strategy.
And those are two very different things.
I've noticed that many owners treat estate planning the same way they treat insurance. They know they need it. They intend to address it. They just don't believe it's urgent.
Until suddenly it is.
A business receives an acquisition offer.
A founder approaches retirement.
A health event changes priorities.
A child becomes involved in the company.
A significant increase in business value creates new tax concerns.
That's usually when the phone call to the estate attorney happens.
The challenge is that many of the most valuable planning opportunities existed years before that phone call.
I've seen business owners spend decades building companies worth tens of millions of dollars only to discover that their best wealth transfer opportunities disappeared as the company's value grew.
The irony is that successful businesses often create estate planning challenges precisely because they are successful.
The company becomes more valuable.
The owner's net worth increases.
The planning window narrows.
The available strategies become more expensive or less effective.
Meanwhile, many of the biggest risks have very little to do with taxes.
Who will control the business?
Which children will own it?
Which children will run it?
How do you treat active and inactive family members fairly?
What happens if the founder is no longer able to make decisions?
Those conversations are often far more difficult than any tax calculation.
In my experience, estate planning is not really about transferring assets.
It's about transferring decision-making.
It's about creating clarity before uncertainty arrives.
It's about making thoughtful choices when you still have options.
The families that navigate these transitions successfully usually have one thing in common.
They began planning long before they thought they needed to.
The wealth transfer itself may occur years later.
But the decisions that determine the outcome were often made a decade earlier.
That's why I believe the most expensive estate planning mistake isn't failing to create a plan.
It's waiting too long to start one.
02 One Number
10 Years
Many of the most valuable estate planning opportunities occur approximately ten years before a major liquidity event, business sale, retirement, or generational transfer.
The earlier planning begins, the more options typically exist.The later planning begins, the more options have already disappeared.
03 What I'm Thinking About
The most successful business owners I know understand the power of compounding.
What many don't realize is that estate planning compounds too.
Small decisions made today can produce enormous benefits for future generations.
The opposite is also true.
Delaying important decisions often compounds future problems.
Time is one of the most powerful assets in both investing and estate planning.
04 Office Hours
If you own a business, ask yourself this question:
If something unexpected happened tomorrow, would your family know exactly how ownership, leadership, and wealth should transition?
If the answer isn't an immediate yes, it may be worth having the conversation now rather than later.
If you'd like to discuss estate planning readiness, succession planning, family office services, board service, or fractional CFO support, reply directly or schedule 15 minutes on my calendar below.
No pitch. No presentation deck. Just a direct conversation about your situation and whether my experience can help.
