Every autumn, the professional world defaults to the year-end sprint: digging deep, clearing the backlog, and pushing to midnight on December 31st in a cloud of dust. Nowhere is this pressure more visceral than in billable-hour or quota-driven environments, where you suddenly realize you need
The September issue of my Personal Strategy Compass newsletter is now available: “The Defense of the Baseline: Drafting Your Personal Constitution and the Re-Entry Gate.”
This issue grew out of something I noticed during a recent major life transition. High-achievers rarely slow down during transitions; they simply shift gears, often into an even
The August issue of my Personal Strategy Compass newsletter is now available: “The Night Watchman: Converting Solitary Anxiety into Strategic Leverage.”
This issue grew out of something I started noticing in my own solitary planning blocks. Once I removed the usual operational noise and created some real white space, my analytical mind did
I’ve just published the July issue of the Personal Strategy Compass newsletter, and it centers on a physical metaphor that hit me during my recent Q3 Personal Quarterly Offsite (PQO).
I caught myself spending far too much analytical energy on a minor home
With the 2026 World Cup underway, it is easy to get caught up in the drama of the opening whistle. But any coach will tell you that games are rarely won in the first few minutes. They are won or lost in the
The May issue of Personal Strategy Compass newsletter is live, picking up in the silence left behind after April’s “acoustic stage” was cleared of its noise and inherited obligations.
If April was about the courage to strip the stage down to its essential signal, May is about the craft required to sustain it.
The
The April issue of Personal Strategy Compass is out, and this one took longer to find its frame than most.
The image that finally unlocked it was Bruce Springsteen’s Tunnel of Love tour. Not the Born in the USA stadium spectacle that preceded it. The moment after, when he stripped the stage down to almost
The March issue of my Personal Strategy Compass newsletter is out.
This month’s piece explores something I’ve been noticing about strategic planning. The hardest part is usually not the work of planning itself. It’s the residue that planning drags along with it.
Ideas, priorities, and intentions tend to accumulate. We carry them forward month after
I ran an experiment at the beginning of February.
I closed my planning system and didn’t look at any of it for 48 hours. No peeking. No referencing. I just paid attention to what actually pulled at my thinking when nothing was prompting me.
Then, on Monday morning, before I opened anything, I wrote down
I launched Personal Strategy Compass as a premium newsletter a year ago. The decision made sense on paper: quality content, established expertise, proven frameworks. But something never quite felt settled.
Not wrong, exactly. Just… misaligned.
Then I drew an Oblique Strategies card during my own quarterly planning: “Honor thy error as a hidden intention.”
If
