Everything, but not enough

Searching for complexity, friction and challenge: the keys to a psychologically rich life

JL Orr of The Travel Paradox

Nov 09, 2025

What is going on with me?

On Thursday, July 3, 2025, I wrote these words. They broke my heart.

‘I am entirely comfortable. Everything I need is here. I have so much freedom.

It isn’t enough.’

The next day I went so far as to write a list: All the things I have that are necessary for a happy life…

I have it all, so why isn’t that enough?

By day 5 of this existential crisis I declared that I was starting to think that I’m not actually built for the ‘good’ life. I said, “The easy life, the comfortable life. I think they might not be for me.”

Here I was with all the time and resources and interests, and my primary feeling was malaise.

But what I hadn’t realized was that leaving work meant that I was giving up challenge, friction and complexity. Retirement had meant embracing the simple life, and this is where things went off the rails for me.

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I’m an overthinker. There is nothing that I can’t chew over endlessly until I’ve driven myself crazy. So what happens when you ‘overthink’ midlife malaise?

This is where I landed.

I was BORED. Which felt UNREASONABLE. I was AFRAID that I was going to waste my life. And I felt GUILTY for not being content and thankful for all that I had.

But I also felt like if I didn’t make a change, I wouldn’t make it. Period.

I have long understood that ‘the good life’ is the search for happiness and meaning. I believed that I had achieved these two goals, and I carried this through to my retirement life.

A third dimension to the ‘good life’

In Life in Three Dimensions: How curiosity, exploration, and experience make a fuller, better life, Shigehiro Oishi makes the case that limiting our understanding of ‘the good life’ to a focus on happiness and meaning misses a critical component; psychological richness. I also talked about this book here.

Happiness is defined as simplifying one’s life so as to have reliably positive experiences. Contentment is the key to happiness.

A life of meaning is about dedicating one’s life to others with compassion.

But for many, happiness and meaning are simply not enough.

Yet the paradox of happiness and meaning is that the complacency they foster can make for an incomplete life with major regrets, doubts, and unanswered questions. - Shigehiro Oishi

“A psychologically rich life is not for everyone. It suits the curious more than the content. The comfort and security of a happy or meaningful life provide a safety net that a psychologically rich life, with all its unknowns, often lacks. Yet the paradox of happiness and meaning is that the complacency they foster can make for an incomplete life with major regrets, doubts, and unanswered questions.”1

Oishi says that to foster psychological richness in our lives we must lean into the unfamiliar, the risky, and the challenging. While familiarity generates reliable happiness for some, it doesn’t generate much richness.

I am one of those people whose life well lived must include not only happiness and meaning; I need psychological richness, that third dimension of the ‘good life’.

“A psychologically rich life is a life with twists and turns, stops, detours, and turning points; a dramatic and eventful life instead of a familiar and cozy one; a life with complexity and multiplicity; a life of expeditus, or spontaneity, rather than a life of deliberatio, or careful deliberation; a life of long, winding journey rather than a simple straightforward one.”2

Every once in a while, a book arrives in my life with exactly the right message. This was exactly the right message for me.

I’ve given myself permission to harness my boredom and discontent as fuel to pursue a different life – a life full of challenge and complexity. I want to keep doing the hard things. I want to live life without regret. I’m going to attempt things I never thought I could do.

What about you? Are you pursuing a psychologically rich life?

Here’s what I’m recommending this week…

Fly little book, fly! by Josefin Waltin

And Parker J. Palmer’s Now I Become Myself

Find out why by listening to the audio version of this newsletter.

Here’s what others are saying about the audio version of Jumble of Sea Glass:

It’s such a lovely experience hearing you read your writing in the way you intended for us to hear it, JL. ~ Min L of A Quiet Turning

I hope you have found something in this JUMBLE of Sea Glass that speaks to you.

I appreciate you spending some time here.

JL Orr

Okanagan Valley, British Columbia, Canada

Going deeper…

If this topic interests you I strongly suggest that you download Shigehiro Oishi’s paper from the 2021 American Psychological Association’s Psychological Review entitled A Psychologically Rich Life: Beyond Happiness and Meaning. I believe this paper is the starting point for his book.

You must also access his book in which he lays out a Top 10 list for psychological richness. I don’t want to give it all away, but I will talk about how I intend to apply a few of his suggestions to my own life.

These direct quotes come from the APA paper mentioned above with page numbers in the footnotes.

Lifelong learning

‘A life of curiosity-driven learning helps individuals acquire skills in perspective-taking, empathy, and creativity needed to solve recurrent adaptation problems encountered in navigating complex, shifting physical and social environments. These skills in turn accrue social and cognitive advantages that benefit not only the individual but also the group. One pay-off of pursuing a psychologically rich life may be increased opportunities for discovery and learning.’3

Even before reading this book I realized that I need to dive deep into learning as a way of keeping my brain fully functioning. I wrote a piece called I sent my brain back to school which laid out my plan to keep my mind fed and watered.

Don’t be afraid of negative results

‘We suggest that one important function of the psychologically rich life is to cope with tragedy and other adverse events. Difficult moments are inevitable. But by valuing them (and the perspective changes they bring), people may find value in experiences and lives that are not otherwise happy or meaningful. In other words, psychological richness requires valuing not only the bright moments of life, but also the darker moments that make such moments possible.’4

While this report primarily focuses on unavoidable tragedies and hardships, this advice can also apply to the times when your adventures and attempts go badly.

While no one enjoys failure, and we might be tempted to avoid failure by avoiding doing hard things, true psychological richness is enhanced by difficulties and negative outcomes, because it is in this place that we find opportunities for perspective change.

Write and tell

‘Thus, it is not enough to simply experience tragedy (or even a great variety of interesting/positive events). For such experiences to contribute to psychological richness requires the ability to remember, actively reflect, and integrate those experiences. A basic prerequisite for such integration is the ability to store and recall memories. Thus, self-reflection and memory may be prerequisites for transforming experiential richness into psychological richness.’5

Self-reflection and memory. We can have many experiences, but if we do not take the time to reflect and document those experiences it is very likely that we will not receive the full benefit of the experience.

‘Processing tragic, dramatic, or surprising experiences by making sense of them may be a key component. Writing about a traumatic event not only improves health, but does so via people’s ability to form a narrative or coherent story that explains the trauma they have experienced.

‘Thus, although tragedies and adversity may offer opportunities for revising mental narratives and structures to accommodate them, actually engaging in such accommodative processing may be necessary to ultimately experience such events as psychologically rich.’6

For me, writing daily helps me to memorialize and understand my experiences. Without this important step it is too easy to let the opportunity for learning pass by. I also choose to tell some of my stories because I think there is a good chance that there are others who can relate and find comfort in my experiences.

Jumble of Sea Glass is a place for me to do this writing and telling. But there is another place in which I process many of my experiences.

Many of the things that make my life psychologically rich happen when I travel. Many of the greatest dilemmas and conundrums I try to unravel are most present when I travel. Travel takes me to places where I often question my most basic perceptions of the world, society, and our natural surroundings.

You can find this writing specifically at The Travel Paradox – it’s exactly what it says on the tin. It’s the search for a psychologically rich life through travel, deep questions, and occasional epiphanies.

I will conclude by quoting from this report:

‘In short, we argue that psychologically rich lives are uniquely associated with curiosity, openness to experience, and willingness to defy systems. Complexity and difficulty fuel psychologically rich experiences, and informant and self-reports converge in suggesting that psychological richness grows over time in response to perspective-changing life experiences such as studying abroad. Finally, not only do people across cultures view a psychologically rich life as a good life, but also a small but consistent minority would even choose it at the expense of a happy or meaningful life.’7

If this speaks to you, I hope you will read more of Shigehiro Oishi’s work. And I hope that you will also share your experiences with pursuing a psychologically rich life with me and other readers.

Jumble of Sea Glass

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