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  • Writer's pictureAndrew Petty

025 The Contentment Conundrum

Cracking the Code


How content are you? A little? A lot? Sometimes you are and sometimes you aren’t?

The fact that we all have different answers to that question just shows how elusive the answer to the Contentment Conundrum remains for we humans. I’ve never met someone who said that being more Content didn’t appeal to them at all.

And if Contentment was easy, we would have nailed it by now.

In this episode, we uncover some of the key reasons that Contentment eludes us and what to do about them--and get a lot closer to cracking the code on the Contentment Conundrum.

This Episode Goes Out to…

The Contentment Conundrum comes up a lot in my line of work--whether in 1-1 coaching settings or in group settings like Graveyard Group masterminds. In fact, I dedicated this episode to the OG TGG, as we call it--the group of guys who came together for the first-ever Graveyard Group mastermind two years ago. I’m a player-coach in that group--it’s where I do my own Mortality-minded work to become the man I’m made to be and live the life I’m made to live. We’re still going strong, and another discussion around Contentment gave me the inspiration for this episode.

What is Contentment, Anyway?

Before we dive in, let’s define what we mean by “Contentment.” For our purposes, we’ll call Contentment “an overall sense of satisfaction and wellbeing that’s based in reality and not dependent upon circumstances.” There may be other ways to describe or define it, but it’s this kind of Contentment that we’re chewing on.

Let’s also touch on what we DON’T mean by “Contentment.” We don’t mean brainless bovine contentment--out of touch with and unaffected by real life in the real world, like a cow grazing in a field as the world swirls around them. There are at least a couple of ways to achieve this kind of contentment--this counterfeit of the real thing. One of them involves self-destructive use of substances or other reality-escaping practices. Another involves simply living in a chronic state of denial. In my opinion, neither of those end well or bring our best into the world. And if you’ve tuned into even just a few episodes already, then you know that in my book, that’s a terrible tragedy. Both for the liver of the life and the world they inhabit.

Paradoxically, although the first definition of Contentment requires more commitment and courage, it yields a bumper crop over time--while the second ultimately requires more desperate measures to maintain against the constant encroachments of reality upon its borders and, in the end, yields a harvest of mediocrity at best and ruin at worst.

My strong hunch, though, is that if you listen to this podcast, you’re much more interested in the first definition of Contentment.

Guest Co-host

As I was chewing on how to approach this topic, I realized that I wanted to have a conversation about it rather than just share some thoughts in the usual solo episode way. So I invited my wife, Charis, to join me. She first appeared on Andrew Petty is Dying in ep. 021, Sometimes, the Grass IS Greener: How a Familiar Bit of Conventional Wisdom Could be Holding You Back from the Life You Were Made to Live. That episode wasn’t an audition, but if it had been, she would have “gotten the part.” And since evidently her first experience wasn’t overly traumatic (rumor has it, she actually enjoyed it!), she agreed to help me crack the code on the Contentment Conundrum with me, for you. Tune into the full episode to hear the many pearls of wisdom she adds to the conversation.

The Contentment Conundrum: Cracking the Code

Our conversation was organized around two major headings:

  1. Contentment can’t be found by looking for it.

  2. We experience Contentment as we persevere in becoming the person we were made to be and living the life we were made to live.

Contentment can’t be found by looking for it.

Before we discussed how we obtain contentment, it was first important to dispel this underlying misconception. In my opinion, not only is it true that contentment can’t be found by looking for it, but the more intent we become on finding it, the more elusive it becomes. It’s like trying to hold on to an eel. Or chasing a mirage. Or mistaking the good times had in the car on a road trip for the purpose of the trip. Good times in the car on a road trip are a by-product of traveling to a destination--not the sole purpose of the trip.

In the rest of this part of the conversation, we discuss how time-honored self-care practices can actually feed into this misconception and create quite the opposite of contentment as a result.

And Charis shares what kind of shape I was in just 3 days after returning from my first-ever personal retreat.

With this critical misconception addressed, we next unpaced what actually does produce contentment in our lives.

The Recipe for Contentment

I think we experience contentment as we persevere in becoming the person we were made to be and living the life we were made to live. There are at least 5 key ingredients in the recipe for becoming the person we were made to be and living the lives we were made to live, including:

  1. Connection with a Higher Power

  2. Finding and Traveling our Unique Path in Life with Guts, Gusto, Abandon, and Purpose

  3. Cultivating Positivity

  4. Practicing Presence and Possession

  5. Making People Our Priority

We walk through this recipe step-by-step in the rest of the conversation, and Charis adds examples from her own life to help you “see” what we’re talking about--including a professional evolution that required a lot of guts and deeper self-knowledge from her and in the end produced a harvest of increased self-confidence and yep--contentment.

I think this recipe yields genuine contentment much like an exquisite meal yields amazing flavor and warmth in our belly. It’s not the meal itself, but it’s an awesome and welcome byproduct of it.

This kind of contentment--genuine, deep, abiding contentment--comes with scars and wounds picked up in the battle of life. In fact, this kind of contentment is possible at least in part because of the scars and wounds acquired in the battle of life. We mistake freedom from suffering, stress, and hardship as a source of contentment. When in fact those are some of the most important ingredients in the recipe for living a life that produces Contentment along the way.

Landing the Plane

Our conversation concluded with two final points. First, we discussed the surprising value of discontentment. And secondly, we discussed how Mortality plays into all of this. Tune into the full episode

So What’s the “So What?”

If you’re seeking more Contentment, first, stop looking for it. Then, commit instead to living the life you were made to live and becoming the person you were made to be. Pay attention to the discontentment indicators on the dashboard of your life. What system malfunction is it alerting you to? Check the recipe of your life. Which ingredient in the recipe for becoming the person you were made to be and living the life you were made to live isn’t there in sufficient measure or is absent altogether?

And as you discover and travel your unique Path in life with greater guts, gusto, abandon, and Purpose, you’ll start to notice the presence of a very welcome and pleasant companion:


Contentment that’s not dependent on fickle circumstances. Contentment that’s rugged and durable and UP TO YOU!

Remember, you ARE going to die. But you’re not dead yet. So get after it!

I Can Help You

With Mortality as our motivator, this podcast exists to help you cultivate the Mindset and the Means to live the life you were made to live with guts, gusto, and abandon. That’s my purpose as a coach, too.

Connect with me on Facebook, Instagram, LinkedIn, visit my website, or email me. Go here to learn about Graveyard Group masterminds----where we make time each week to invest in your life's most important work.

Episodes Mentioned in This Episode

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I’d Love to Help You

My purpose as a coach is to help you live the life you know you were made to live--with guts, gusto, and abandon. Connect with me on Facebook, Instagram, LinkedIn, visit my website, or email me. Go here to learn about Graveyard Group masterminds----where we make time each week to invest in your life's most important work.

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1 Comment

Bonnie Haines Church
Bonnie Haines Church
Mar 12, 2021

I have listened to the contentment conundrum thrice and am sharing it widely. Andrew offers such nuanced insights that demand more than one listen...and Charis is so real. Thanks for helping us pay attention.

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