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November 30, 2020

Recently, thoughts about how I spend my time, energy, and expertise; and if I am living up to my full potential day-to-day have been top of mind. I question if I am giving my best efforts to the various communities I am a part of. Part of this contemplation is directly related to completing my Master’s degree at the beginning of the year and not yet feeling like I am applying the knowledge I gained or skills I developed over the course of my studies. More than this, I am thinking about the period I am at in life, what I have to show as the culmination for a life’s worth of work, and I find myself comparing where I am at to what others what to show” for their comparable position in life. Considerations such like this are never healthy, neither is considering one has completed a life’s worth of work at the age of 37, but here I am.

For the longest time I have held myself back from pursuing roles of management and formal leadership. The main reason for not advancing” further in terms of traditional bureaucratic structures— I struggle to find alignment between my personal core values and what society says managers and leaders should be. Although I do believe that leadership doesn’t require a title, having written very personally about this:

In considering the leadership roles that I have held throughout my career, I am reminded that the most rewarding and valuable ones were those that I undertook with no formal permission, title, or recognition. Such roles have proven to provide me the opportunity to make significant impact, within a community, without being hindered or directed by politics, organizational mandates, administrative procedures, or bureaucratic processes. I have found that these types of informal leadership roles allow for my work to remain connected to the communities I aim to serve while limiting outside influences from individuals or organizations such as funders, politicians, and private interest groups. - The Importance of Place

I can’t help but to consider the need to play the games which our society demands we play. If we wish to live a life that balances personal needs with monetary demands, while at the same time battling bouts of severe depression rooted in understandings of personal identity tied to a Protestant work ethic engrained in our North American culture, there is a strong but unhealthy argument that is too easily made about giving in to capitalism which is all too invasive in our life’s and simply playing the game we’re born into.

But I digress.

These thoughts have me wondering if I am holding myself back from making the most impact I can make in life. When I consider the things that frustrate me the most with the management structures I work under, and what many organizational structures constitute as leadership, I question if I am not taking the necessary steps to remedy the frustrations I face. Wouldn’t becoming a manger, or formal leader as recognized by institutions, be a solution that would provide some additional opportunity to change the structures that stress me out the most while trying to eliminate the frustrations my colleagues and I face? While this may very well be the case, a fear I have is that if I were to advance” through corporate and organizational labyrinths I would become the very version of management and leadership which I have come to despise or that the work itself will be so demoralizing that I will lose all interest.

Informing these thoughts is the consideration of what the purpose of a career is, versus a job, and how I wish to invest my energy in life. James Shelley summarizes many of these thoughts succinctly as part of his book-in-progress, Simplicity Praxis. Of particular interest is the section titled, Mediocity, which rethinks the terms of engagement when it comes to achievement and success. Sub-sections include considerations on: being micro-ambitious, the wisdom of doing as little as possible, and perhaps the most relevant of the sections for the considerations I am having—The Careerist vs. The Dilettante. Over the years I have returned to James’ words time and time again as they resonate deeply with my values and beliefs. This period in my life is no different.

As I continue working through these thoughts, wait with the remainder of the world to understand how our global pandemic will shape immediate and long-term futures, and look into the coming year to see what it might have in store for me I can’t help but to think about the uncertainty which (always) lies ahead. Thankfully, James has words to help with this too:

Instead of chronically fearing, dreading, or ignoring the inevitable surprises and shocks to come, what shall we do with them? We could try examination and exploration. In an embrace of uncertainty, we might adopt a genuine inquisitiveness about the strange and zany things that life constantly throws at us. - Uncertainty, as mantra by James Shelley


  • I am finished my annual re-read of Essentialism: The Disciplined Pursuit of Less by Greg McKeown
  • I am finished reading for 2020. My aim for the remainder of the year is to focus on developing out my reading plan for 2021; an approach that will have me reading fewer works but spending a greater amount of time with each, contributing to a dive deep into a select number of topics that I find particularly interesting.
  • After a month away from the Good City Co. community I will return tomorrow to see what has transpired over the past month. I am looking forward to returning recharged and finding ways to engage in the ongoing discussions and work of the group.
  • I am freaking out about the potential for the floors to collapse in my home. Spending 24hrs 7-days-a-week in my home had provided ample opportunity for me to experience every nook and cranny of this place, for better or worse.
  • I really enjoyed this 20 year old episode of This American Life titled, Americans in Paris. It is definitely worth a listen.

November 30, 2020 Now


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