Essay One | The Observatory Deck

I am present in my life, engaged in it, moving through it with genuine care. Alongside this engagement there has always been something else, a vantage point, an interior space where I observe not just what is happening around me, but also the unseen things happening within: patterns of thought, motivations, some mixture of feelings flowing through, and a curiosity for what might be alive and happening within other people around me.

This manner of observation isn’t unique to me. I’ve encountered many people who, to varying degrees, engage with the world in this way.

Sometimes I think of it as a room filled with chandeliers, each one casting its own cluster of light, with my mind then wandering and browsing, looking for the interconnections and relationships between them.

I have come to refer to this analytical vantage point as the observatory deck.

Why do I bring this up?

Because for the past twenty years, this observational habit has quietly maintained its focus on a question.

The Question

I still remember a morning bus commute early in my career, when I was a new articling student at one of the big four accounting firms. Every day, the bus drove past a café, and through the window I could see people sitting with their coffees, unhurried, and with seemingly no particular place they needed to be.

I wanted that. Not just the coffee, but the ease.

The sense that life was still simple enough to just inhabit and enjoy it, to sit in the sunshine, to spend time with family and friends, and to go on a leisurely walk, with no urgent or weighty responsibilities to complicate things.

I was in my twenties however, and that feeling of freedom and ease was beginning to recede. There was an immense amount to learn vocationally. A fixer-upper house mid-renovation. A first child on the way. Finances tight. The days were full in a way that felt meaningful and promising on one hand, but also slipping beyond what I could elegantly hold.

I was well-intentioned and I worked hard. My father and mother modelled, then and still now, a quiet, serious diligence that I absorbed early and carry still. But even so, I was beginning to notice that effort, professional competencies, and good intentions alone were not quite enough.

The question that would follow me throughout the next twenty years was beginning to form:

How does a person steward their life well?

Not just manage it, not just survive. But steward all of the active life domains, with intention and purpose and some sort of structure that is actually proportional to the weight of the responsibilities carried.

I’ll pause here briefly to acknowledge that the term stewardship is not used very often outside select circles or the not for profit sector, but I do have a specific meaning in mind when I use this term. I’ll unpack it carefully as this series of writings continues to unfold.

And so - at the core, what I was wrestling with was how a person who carries genuine ongoing and complex areas of responsibility, across the life domains of work, family, finances, personal well-being, admin, household, relationships, and community, move through that responsibility with some measure of clarity and peace? Is it simply common sense? Am I alone in contemplating this? Is it possible to be present and engaged as husband and father, within my profession, as a friend and community member? Not by simplifying one’s life down to something it isn’t or sacrificing one life domain at the altar of another, and ideally, also not by merely increased hustle, burning the candle at both ends, pushing beyond one’s limits to such an extent for such a duration of time that things start to break and fragment beyond repair.

In the seasons of life that followed, I became well acquainted with what the absence of an answer can feel like. The sense of overwhelm at the sheer volume of competing responsibilities that never fully resolves; tasks, projects, and obligations spread across every domain of life, each one legitimate and deserving attention, with the evolving risk that none of them will quite get the attention needed to thrive.

Then there is the sensation of feeling troubled by your own good intentions. Wanting to work hard, wanting to show up well, wanting to be the type of person that can handle everything, but then finding that the sense of meaningful peace, calm, deep rest, stability, and quiet satisfaction never quite arrives, at least not fully, even when you are giving genuine effort.

There is the stress of feeling party to a cycle you can recognize, but cannot seem to exit. Batches of time sensitive and important urgencies surface, your nervous system and adrenaline respond, and you address it. Followed by a brief welcomed relief. Until then the next cluster of urgencies arrives, while somewhere in the background, the growing list of important things—the things that are not yet on fire but will be—continues to smoulder and wait for its time to become time-sensitive, urgent, and on your radar.

Then there is the apprehension or underlying sense of fear about what might fall apart if you allow yourself the space and time to rest, taking your eyes off the ball. Or the feeling of ambiguous guilt that somehow surfaces just in time to sabotage your rest. Or the particular loneliness of trying as hard as you can, while carrying the quiet persistent feeling, that it still isn’t quite good enough, and not being sure anyone around you understands.

Ultimately, at a certain point, it can feel like you have leaped off a cliff—into marriage, parenthood, your vocation, into the full weight of adult responsibility—and you are now scrambling to build an airplane, while in free fall, hoping to have it airworthy before you run out of altitude.

And so the question arises, how do people do this? How does one develop the capacity, the structure, the necessary constraints and rhythms to hold what is being carried, and hold it well?

I did not have an answer to this question then. And I’m not sure I have a complete one now. But I have been living inside this question for a long time.

I do want to point out that in response to this dilemma, some voices have said: Phillip, you just need to simplify your life. And I agree, there are times where the most prudent thing is to be clear on boundaries, to gracefully say no, and to do is to shed certain responsibilities. But I have found that this can only take you so far. There are legitimate situations where the question cannot be how to carry less. Your responsibilities are real and they are yours, and shedding or simplifying them is simply not a viable option.

There is, of course, another option, or perhaps it is more of a coping mechanism. Neglect, avoidance, and denial. Perhaps paired with some form of therapeutic rationalization and justification. But then again, the question isn’t how to feel better. The question is how to sustainably carry what you have well—with structure, with rhythm, with intention, with something that looks less like fragmentation and more like art and grace.

And so—that is what this series is about.

Fair warning, by trade I am a CPA and finance professional and so I do not bring any sort of academic credentials in life design. What I bring is twenty years of quiet observation—of my own life, of the lives of people I have worked alongside, and of the serious thinking that thoughtful writers and researchers have contributed to these and related questions. In short, I am a careful observer who has spent a long time with this question.

If any part of what I’ve described feels familiar—the weight, the cycles, the fragmentation in how you’re carrying your life responsibilities —then my hope is that this series of writing and careful exploration will be both thought provoking and of practical service to you.

My observatory deck has been a private space for a long time. I look forward to opening it up.