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Is Your Endgame 100% or Just 50%?

Is Your Endgame 100% or Just 50%?

April 26, 2021

Multiple unforgiving players influence your retirement and estate plans (collectively your “endgame”). They include the IRS, the Social Security Administration, and the Center for Medicare and Medicaid Services. Several of your most important decisions with these players are nearly impossible to reverse. Plus, if you qualify for a pension, how you activate it is another irreversible decision.

If you’re married, then your one-time decisions compound the outcomes. Are you more of a planner than your spouse?

Countless endgame “plans” were created by 50% of a couple:

  • the 50% who typically is the first to die,
  • leaving the surviving 50% not only grieving the loss of the deceased 50%,
  • but in 100% distress
  • at having 0% clue as to what that “plan” entails
  • if it ever even existed beyond the first 50%’s fading memory to begin with!

Do you know anyone in that boat?

Plus, there’s nothing like no plan to set up a widow or widower for failure or worse—elder abuse.

Should you decide to seek professional help with planning the final chapters of your life, congratulations. Smart move. After asking questions you expect to hear, that pro better ask you some questions that challenge your comfort zone. If those conversations are 100% feel good, “everything is awesome,” then your plan will be unrealistic.

There is a balance in the conversation between being optimistic, aspirational, and realistic. But realistic means just that—not all that is real is comfortable to consider.

In my book, Keep Your Life: Plan Your Endgame So Loved Ones Stay Loved Ones, I elaborate on two steps to avert being taken. Briefly, the first is to understand how your advisers are compensated. The second is to apply the wisdom of teams. Your team should include select licensed professionals and select Loved Ones.

A plan is not a portfolio, a pile of documents, or wishful thinking. Rather, it is a mission.

Think of it like the Apollo Mission that John F. Kennedy launched in 1962. It was bold, bodacious, fraught with risk, full of aspiration, with a decade horizon for success—to reach and return safely home from where no person had ever gone before.

Now, you might be thinking, “Millions of people retired before, and millions more will.” Yes, but for you it’s the first time. It’s a new frontier. And by the time you realize you’re ill equipped, you have the least amount of power to do much about it.

If you “plan” to retire a decade from now and haven’t begun to plan, you’re behind. Not hopelessly behind, but consider this: every year you delay, you lose a degree of freedom and security.

How’s that?

Each year put off is one less year for the good stuff to be compounding for you: risk-adjusted growth, optimizing contributions, and diversifying your tax buckets as you nimbly navigate ever-changing tax laws. Right now, you’re the youngest and probably the healthiest you’ll ever be. That can matter a ton for earning potential and for favorable underwriting of your protection policies.

Each year put off is one more year for the bad stuff to compound against you: faulty assumptions, suboptimal portfolio design, paying excessive taxes, or faltering marriage uncounseled. Divorce costs 50% plus fees.

My wife, Karen, is right-brained. When we met 40 years ago, she knew immediately that I was “the one.” Go figure. But then, she didn’t “figure.” She felt it. I’m left-brained. And no joke, I spreadsheeted the situation for 8 years before committing. Did I mention she’s patient?

Karen has 0% desire to get into the nuts and bolts of planning. Yet, she has 100% desire for 100% assurance to be safe and secure when (presumably) I die first. Her 100% assurance is because her 50% joined my 50% at the table. That’s a 100% endgame.

And if you’re single, that other 50% could be whoever is most important to you.

I’d love to hear from 100% of you. When it comes to planning your endgame, what’s your single biggest challenge, frustration, or concern? Kindly put “PREP” in the email subject line so I’ll know you’re responding to this article. Feel free to be detailed and specific. Email me at

DISCLAIMER: The views and opinions expressed in this article are those of the author and do not necessarily reflect the official policy or position of Global View Capital Advisors, LTD or any of its affiliates.

This article was previously published in the Post Register.

Photo by Mike Palmowski on Unsplash