Cultivating Contentment

Stop keeping track

It's a challenge to stay content when you'r keep score. Keeping a mental tally of the work you do, and then expecting it to be reciprocated is what I refer to as a one-way promise. If you're a people pleaser, you'll continue to do more, secretly expecting some 'pay day' later. The longer we wait, the more resigned we grow and resentful of the other. Author Richard Carlson explains that this is actually the foundation of Don't Sweat the Small Stuff.

Drop your expectations

We seek happiness, yet happiness is fleeting. It's here one moment and gone the next. What we ought to instead be seeking is contentment.

By design, happiness is unexpected. The more we search for it, the more elusive it is. When we expect it, it rarely shows up. In fact, expectations alone can thwart happiness altogether! Think about the last movie you enjoyed. If you went to expecting it to be good, did it live up to your expectations? If you went to it without a single expectation, were you surprised it was good? It's why once you've read the book, the movie rarely lives up to it!

Sidebar: This gets into something in regards to prejudices and preconceived notions. The halo effect. False assumptions about somebody or something.

Metrics of happiness

Whose defining what makes us happy? Is it culture? Is it marketing? Is it our parents? Our friends? Our spouse?

Or is it us?

Pain vs. suffering

Is suffering a habit? Although the pain is gone, do we continue to suffer? If your life have moved on, but your stuck in the last chapter you just read?

The View

We live in a constant continuum of pleasant, neutral and unpleasant. Every moment, activity, and exchange moves the needle.

'The View' is a buddhist term that refers to our ability to see this and to be content in all 3 states (and every variation of such).

Does a good life require we spend all our time in the pleasant state? I think you'll find you put yourself through a lot of unnecessary suffering if you live this way.

Two paths to cultivate contentment:

  1. Discern the truth
  2. Appreciate what we have

Discern the truth

Recognize that we are alive, here now, and human. Alive as human beings and not here as an insect, chicken, or cow. That we live where we live and not in some war torn part of the world.

Appreciation and Gratitude

There are entire courses on this topic, but the basic premise is to recognize our blessings.

Happiness is impermanent.

Drama

It's takes others to fuel the drama in our lives. Others will fuel the drama! Don't go there. Be stoic. You can accept everything as it comes, without judging it's it good or bad. You are getting clues as to which way to go next. If you are sad, angry, or anxious - it's a clue to do something about it!

Self-Agency

Contentment within self-agency looks like doing the best work you can with the body, skills, and circumstances you actually have today, and letting that be “enough” without tying your worth to the outcome. It is the shift from “Did this beat my old record?” to “Did this express my current potential with honesty, effort, and care?”

Contentment and control

Philosophical traditions like Stoicism define the healthy locus of contentment as what is “up to us”: our attitudes, choices, and actions, not external results, other people, or time. In practical terms, that means measuring a good day by whether you lived your values and made a sincere effort, not by whether you hit an old number or somebody else’s standard.

When you cook a meal, the “win” is choosing good ingredients, paying attention, adjusting seasoning, cleaning up, and serving it with care, all within your actual skills and energy at that moment. The satisfaction then comes from integrity between intention and action, not from whether the result could impress a professional chef or your younger self.

Potential as a living target

Aristotelian and modern “self-actualization” frames both say that fulfillment is realizing your potential in the present conditions of your life, not in some fixed, idealized past version of you. Seen this way, “potential” at 55 with back pain is different from “potential” at 35 with a bulletproof spine, but it is not lesser; it is simply a different arena with different constraints.

Under that lens, a 45‑minute, intelligently scaled workout done with attention and respect for your body is you fully realizing today’s potential, not falling short of yesterday’s. The personal best you are chasing becomes qualitative (presence, form, consistency, alignment with your values) more than purely quantitative (weight lifted, miles run, hours logged).

Aging, expectations, and self-compassion

Research on aging consistently shows that self-compassion—treating yourself with the same understanding you’d offer a friend—helps older adults cope better with pain, physical limits, and lost capacities. Beating yourself up for not performing like you did at 35 not only ignores biological reality; it also predicts worse physical and emotional outcomes over time.

Resetting expectations is not settling; it is accurately updating the game you are playing so that effort can feel meaningful instead of like chronic failure. A self-compassionate stance might sound like: “Given my age, my back, my sleep, and my life right now, what does an honest, caring effort look like today?”

What this looks like day to day

In practice, contentment inside your own agency can look like:

In that light, growing older becomes less about losing former capacities and more about deepening into a style of living where process, honesty, and self-respect carry more weight than any scoreboard ever did.