Are You Winning in Retirement?

Retirement has never been a game of winning or losing. However, in less than 80 years clear characteristics of winning in retirement have emerged in modern society – having a sizable nest egg and the ability to do whatever you want. Don’t believe, me? Google the word “retirement” and check out the results. You will find an endless list of the latest tips and tricks to secure more income or rate of return. If the blog or article isn’t financial in nature, it’s likely about how to spend your money or stay busy with all of the newfound free time.

According to the American dream, the more money and more leisure you have, the more you are winning in retirement.

Here is what winning in retirement is NOT…

  • Winning in retirement is NOT about how much money you have
  • Winning in retirement is NOT about how well your investments are doing
  • Winning in retirement is NOT about staying busy, but also…
  • Winning in retirement is NOT about how much free time you have
  • Winning in retirement is NOT about how few responsibilities you have
  • Winning in retirement is NOT about doing nothing

Recently, I stumbled across this t-shirt for sale that says, “Retired: Super Busy Doing Nothing.”

Obviously, I understand the satire. But, should this really be the goal of retirement? Should winning in retirement be when you have the ability to do nothing?

The more nothingness in retirement, the better?

Occasionally, you will find well-intentioned articles trying to help retirees combat nothingness. Here’s an excerpt from an article written on how to structure your retirement day.

Now, through the lens of the American dream, endless days like this are a grand-slam! You would have lots of time for rest, relaxation, hobbies and socializing (none of which are bad, by the way).

I can guarantee, if you live each day like this you certainly won’t have any stress, but you will be BORED within a short period of time.

Pastor and author, John Piper compares in his book Rethinking Retirement the American dream of retirement to a curse. Obviously, Piper has some very strong words which speak directly against the world’s view on what winning looks like in retirement, but does he have a point? Is the way modern society defines a win in retirement really a curse and a sign of misfortune?

O God, don’t let me waste my final years! Don’t let me buy the American dream of retirement—month after month of leisure and play and hobbies and putzing around in the garage and rearranging the furniture and golfing and fishing and sitting and watching television.

Lord, please have mercy on me. Spare me this curse.

~John Piper, rethinking retirement

The truth is you were created for more.

You have a specific purpose, calling and assignment for your life. This does not change the moment you retire. Retirement is a crescendo, not an end. It is a time where your fulfillment should increase, not because you don’t have the stress of work, rather, as a result of stepping into a deeper realm of your own existence. Your life experiences, good and bad, have all prepared you for this season – where you begin to walk fully into who you were uniquely created to be.

As you walk this journey, not only do you feel more fulfilled, but the impact you have increases as well. Oftentimes, this happens will less effort. You will still have plenty of time for rest and leisure. However, the rest and free time are book-ends to impactful and purposeful work.

You won’t have idle, unintentional or wasted time. And best of all, you will KNOW that you are ending well – having a life well-lived, confident and regret-free.

Winning in retirement is possible, but you won’t find it following the world’s definition.

Ready to begin actually winning in retirement?

There’s a better plan and process.

I’d love to chat.

Go to and click on “Breakthrough Call“.

Retired Repurposed Available on Apple Podcasts

Jerrid Sebesta

Co-Founder of Retire Repurposed

Co-Founder of Retire Repurposed Jerrid Sebesta