Some of the most meaningful health investments in my life did not begin with intention. They began with curiosity. With travel. With sitting quietly in rooms where I had no business being the expert.
Since my early twenties, I have traveled across New England, sometimes across the country, and often up into Canada for professional continuing education workshops in fields that, at least on paper, had nothing to do with me. Manual therapy courses. Communication intensives. Psychology adjacent trainings. Somatic work. Education spaces where my name, credentials, or resume carried no weight.
I keep going because I am endlessly awed by the people I meet there. The depth of experience they bring. The wildly different perspectives on life, health, values, and what it means to contribute something meaningful to the world.
I ask questions. A lot of them. What drives you? Who do you admire? What do you want more time for? What feels misaligned right now? What are you building toward?
It is a numbers game. Some people are unsettled by that level of curiosity. Others lean in.
Enter Annalise Calder-Wright.
The Unexpected Oracle in Yellow Crocs
Annalise is a friend, a savant cellist, a gifted linguist, a data analyst with extraordinary pattern recognition, and a walking contradiction in the most delightful way. She wears yellow Crocs. A fanny pack. She laughs loudly and often. She cheers people on like it is her full time job.
If you met her casually, you might assume she is simply the life of the party. Boundless energy. An infectious laugh. A cannon of expressions that seem to loop endlessly. “Oh NICE!” “Super COOL!” “Rad!” “Oh WOW!” on repeat.
We were paired together during a workshop. Within minutes she smiled and said, “Oh… you are verbal. Niiiiice.”
Typically, I sit back in these environments. I observe. I listen. Even when I sense my brand of questioning could add texture, I lay low. More often than not, simply listening exposes gaps in my own thinking or reinforces ones I already suspected.
A small group of us decided to grab dinner. We talked. We wandered. Eventually, we headed back toward our shared lodging. Somewhere along the drive, a song by Fulton Lee came on.
Annalise started bopping along and casually mentioned that she plays the cello.
That small, almost throwaway comment cracked something open.
As we walked the streets of Walpole, Maine that night, a deeper layer emerged. Annalise is the daughter of a highly celebrated composer. A musician who spent years immersed in classical traditions, including an extended stay in Germany to explore the roots of the music she loves.
Her demeanor shifted, like a jukebox taking a sharp left turn mid playlist.
What revealed itself was not just talent, but depth. A deeply analytical mind. A curiosity that runs far deeper than the surface. A sense of self so steady that she never needs to brag, overshare, or compete in spaces she could easily dominate.
The Investment, Named Briefly
This is the moment where the investment becomes clear.
Within the Health401k® framework, this was an unexpected, multi level health investment rooted in something deceptively simple: intentionally placing myself in environments where curiosity could compound.
Not as a personality trait, but as a portfolio allocation.
Asking deeper questions of strangers. Letting younger people influence me. Seeking people who reorganize my thinking rather than confirm it. Occasionally choosing one learning environment per year where I am not the expert, recognizing that for some, that may look like a weekend workshop, a community class, or even a single intentional conversation.
This investment did not look like “health” on the surface. But it paid dividends across multiple dimensions.
How the Returns Showed Up
- Intellectual: Conversations with Anna invite entirely new angles of inquiry. Music, language, bodywork, pattern recognition, and how ideas translate across disciplines.
- Social: New friendships. New circles. New people entering our lives who would never have crossed our path otherwise.
- Environmental: Invitations into unfamiliar spaces. Dinner parties. Outings. Creative environments that feel both novel and nourishing.
- Spiritual: A shared reverence for music, art, language, and humanity. The quiet meaning that emerges when people feel deeply seen and understood.
- Emotional: The richness that comes from being challenged, surprised, and expanded by another human being.
These conversations did not just enrich us. They inspired us to act.
Adria and I began bringing together people who did not know one another but felt like they should. A social experiment of sorts. People change people™, in the wild. Watching new connections form has been one of the most gratifying experiences of our adult lives.
Watching Someone Clarify Their Own Portfolio
One of the most meaningful parts of this relationship has been watching Annalise clarify her own priorities in real time.
She is exceptionally talented in the digital marketing world. A gifted data analyst. A pattern recognition savant. And yet, her heart continues to pull her toward manual therapy.
Watching her drill down on what matters, create a clear hierarchy of priorities, and intentionally reallocate her time, energy, and resources has been extraordinary. She is thoughtfully managing the areas of her life that tax her physically and emotionally so she can move toward a vision that feels more aligned.
This is what intentional health investment looks like in practice. Not perfection. Not optimization. Alignment.
The Question That Lingers
This story is not about Annalise being exceptional, though she is. It is about what becomes possible when we treat curiosity as something to invest in deliberately.
When we allow unexpected people to reorganize our thinking.
When we widen our environments instead of narrowing our behaviors.
What would happen if we stopped fixing behaviors and started fixing environments?
Ryan Travis Woods