Taylor Schulte

Minimizing Regret in Retirement

Published 2 months ago • 2 min read

Hi Reader,

They say that a checkbook and a calendar never lie.

If that's true (and I believe it is), then we should occasionally ask ourselves an important question:

"If an impartial observer tallied how you spend your time and money, what would they say is important to you?"

While I'm certainly hopeful they'd say that you spend your time and money in complete alignment with what's most important to you, most of us likely feel that we could do a bit better.

To help better align your time, money, and values, let's explore how we might spend more intentionally so that we'll look back with more satisfaction. More gratitude. And more awe.

In the book Die with Zero, the author, Bill Perkins, writes the following:

"The business of life is the acquisition of memories. In the end, that's all there is."

When we lose someone we love, what do we do?

We recount our memories with that person.

And since memories are often the result of having landmark experiences together...

...they should motivate us to pursue experiences that provide more memories with our loved ones.

Every landmark experience produces those memories through three distinct and enjoyable phases:

  1. The anticipation of the experience.
  2. The experience itself.
  3. The lasting memories (and photos) those experiences create.

Perkins calls these "memory dividends" because each experience adds to the memories that have come before.

(Similar to compounding in investing, but applied to life.)

What's interesting about these landmark experiences is that the most common regret is not having done it sooner.

Perhaps you've said those words yourself. And yet, we often delay the next one into the distant future.

But why?

Based on my experience and observation, people delay for two reasons:

Fear of squandering their money and/or "someday thinking."

Perkins addresses the first concern by saying:

"We shouldn't let opportunities pass us by for fear of squandering our money. Squandering our lives should be a much greater worry."

Rarely does anyone talk about that latter part.

But we should because we aren't promised tomorrow, which brings us to the second reason.

With "someday thinking," we tell ourselves that we'll eventually get around to doing this or that as if our time is infinite.

As a clarity exercise, ask yourself:

What if 'someday' never arrives? Will you regret not acting while you had the chance?

To be clear, there are occasionally good reasons to delay when the time or money isn't quite right.

But to paraphrase Zig Ziglar:

"If you wait until all the lights are green to head into town, you'll spend your whole life sitting at home."

I don't want that for you.

So, as your wheels start turning, please note that the experiences I'm advocating for don't have to be expensive; they just have to be memorable.

Sure, you may want to travel the world. Or eat at MICHELIN Star restaurants. Or buy a luxury car.

But you may also find novel ways to spend time with family or help those less fortunate. Or maybe some of each.

There is no "right way."

As you explore what's possible, remember that the very purpose of financial planning—either on your own or with a professional—is to help you live your best life.

However you define it.

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Stay wealthy,

Taylor Schulte, CFP®

Taylor Schulte

Retirement and tax planning plain English.

I'm the host of the Stay Wealthy Retirement Show and founder of Define Financial, an award-winning retirement and tax planning firm. When I’m not helping people lower their tax bill, you can find me traveling with my wife and kids, searching for the next best carne asada burrito, or trying to master Adam Scott’s golf swing.

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