What’s My Why?

(Some Rambling Ruminations)

I’ve been encountering the “why” question over and over again in my media consumption, from Simon Sinek’s compelling if “lightweight” TED Talk and book Start With Why, to Greg McKeown’s more substantive call to create a concrete yet inspirational Essential Intent in Essentialism, to the myriad of times the exhortation is repeated Brian Johnson’s PhilosophersNotes personal development book summaries. All of these call me to clarify my why in order to keep it central and avoid the ever-present allure of both trivial distractions and genuinely good but lesser opportunities.

I suppose I have sought a why since I was able to frame such questions, sometimes more, sometimes less, consciously. My teenage aspirations to be a scientist were a first rough but still reflective expression of that search for why. My unintentional college major in and continuing love of philosophy was and is probably at least in part another.

In my 20s, after reading Stephen Covey’s classic of personal development, The 7 Habits of Highly Effective People, I developed a “begin with the end in mind” mission statement answering “why” that still resonates with me today:

To fearlessly seek the truth.
To act always with honesty and kindness.
To find laughter, wonder, and joy each day.

The headline for that mission statement, a personal motto inspired by my reading of Robert Pirsig’s Zen and the Art of Motorcycle Maintenance, was:

Arête: Excellence. Virtue. Quality.

While I daily (hourly) fall far short of my own ideals as expressed in that mission and motto, those precepts still do seem like the path to a life of excellence. However, I now detect a fatal flaw in that broad formulation in that the commitment I was making for myself was to “excellence” in all things. I have in my middle-age learned (quite painfully and repeatedly) that striving for excellence in all things is the exhausting and unattainable path of a perfectionist, an impossible self-imposed ideal from which I am (only too slowly) recovering. As a result, I now see the need for a strong filter to select those things in which I “truly” want to attain excellence. The trivial many do not deserve such attention and should simply be passed by entirely, not pursued with excellence.

And so in more recent years I have sought to narrow my focus, to decide what has meaning for me or what I want to make of meaning to me. Through my decision to pursue an MBA and the reflections those studies afforded, this question of what my “why” is focused significantly on career, an avenue I think appropriate for my stage of life. My preoccupation has been clarifying the intersection of my passion, my skills, the needs of the world, and what I can get paid for:

Ikigai (Japanese): Enjoyable motivation to “get up in the morning” (Image Credit)

The question I have been pursuing is: While remaining that truth-seeker committed to excellence, what can I focus on to make the greatest contribution, to make the best use of my limited life?

In my reflection paper for U of C professor Davis in Business Policy, I developed a filter for opportunities based on a hierarchy of values I have come to accept. This hierarchy (in simplest terms: physical-biological-social-intellectual) directs me to devote myself to a creative project at the highest level of value at the greatest possible scale.
Sounds great. A step narrower than excellence in all things but still consistent with valuing truth-seeking intelligence above all.

But, still not narrow enough to be practical… What is my why?

TaskTrain is my current professional passion project. But a B2B SaaS app is not the ultimate end to which I would seek to devote my life energies. So what’s the why behind it? And how might I articulate it as a mantra or motto or elevator pitch that is succinct, powerful, and meaningful to others?

I’ve taken a stab at this in my LinkedIn personal branding: Strategy + Systems • People + Process.

While it fails the powerful and meaningful test, I do think that it succinctly expresses much of my unique core, at least professionally, but also personally.

I love systems. Systems thinking has been an interest of mine since I took UW-Madison Professor Tim Allen’s Integrated Liberal Studies 252 course in college. ILS, and this course on systems theory in particular, exposed me to an intellectual approach that was rigorous without being exclusionary. (It was, well, Integrated.) A system, of course, is a set of interrelated parts that carries out some (goal-driven) activity. Processes are the dynamic side of the systems view of the world. Both process philosophy and process management both resonate with me strongly. My interest in the former, sparked by Pirsig’s process-oriented “Metaphysics of Quality”, led me to the work of other process-oriented philosophies like those of William James, Alfred North Whitehead, and Henri Bergson. My appreciation of the latter was deepened by my first Master’s degree in Systems Management, as well as follow-on studies and American Society for Quality certification in the process/quality-management methodology of Lean Six Sigma.

So with that understanding of my interests and competencies, professional elevator pitch iteration #1:

I design systems to dissolve problems, integrating people with efficient process to achieve strategic goals.


I design systems that integrate people and process to effectively and efficiently achieve strategic outcomes.

Still stinky.

I push for progress by creating systems that effectively integrate people and process.

Not as repellent.

I promote progress by creating scalable systems to solve painful, pernicious problems.

Hmmm. Or as a motto:

Promoting progress by creating scalable systems to solve painful, pernicious problems.

Or with the tag line:

Promoting progress by creating scalable solutions to painful problems.

Strategy + Systems • People + Process

Or as complete sentences:

I promote progress by creating scalable solutions to painful, pernicious problems. I integrate Strategy and Systems with People and Process.

Still overly broad, as it doesn’t integrate my value hierarchy or personal interests. Maybe:

I strive to promote progress by integrating strategy and systems with people and process, creating scalable solutions to pernicious problems in areas I care about: education, environment, efficiency, economy.

The tagline version:

Promoting progress by creating scalable solutions to pernicious problems.

Strategy + Systems • People + Process

Efficiency • EdTech • EcoEconomy

Progress? Perhaps. Not as inspiring as I might like, but it is a bit more specific and does capture something meaningful about my Ikigai.

Does it make sense to anyone but me? Hard to say without feedback.

What do you think? More importantly, what’s your why?