Welcome back to our weekend reflection on leadership, legacy, and the quiet strength that forges true victories—not always in boardrooms or on fairways, but in the unyielding pursuit of principle. This weekend (October 24–26, 2025) provides a rich tee-off point for our theme of “enduring American grit,” as the ever-defiant Donald Trump embarks on a high-stakes Asia tour while navigating domestic headwinds at home.
In this edition, we’ll break the trip into three business-lessons drawn from three rounds on the course:
- Lesson 1 – Boldness on the Tee (Friday, October 24)
- Lesson 2 – Chipping from the Rough (Saturday, October 25)
- Lesson 3 – Putting for Purpose (Sunday, October 26)
Let’s step up to the tee.
Lesson 1: Boldness on the Tee – Friday, October 24
On Friday, President Trump departed for his Asia trip, aiming for Malaysia, Japan and South Korea — a bold international move amid domestic turbulence. Yahoo News+3Politico+3Al Jazeera+3
On that same day, his administration announced federal monitoring of elections in California and New Jersey — a domestic assertive step in a time of government shutdown uncertainty.
Business/leadership takeaway for our “golf” metaphor: On the tee box, you often face winds you didn’t expect — similarly, stepping into new markets or arenas (like Asia for Trump) while handling internal disruption demands boldness. You need to swing with conviction even when the fairway seems obscured.
- Saying “we’ll find a way to fund food stamps” amid a shutdown: a demonstration of playing through adversity.
- Pulling out of trade talks with Canada over a provincial ad: a bold decision to reshape the field.
- Addressing the demolition of the White House East Wing and the naming of a ballroom — symbolic shifts in architecture of power.
In business terms: when you’re at the tee, sometimes you have to choose your club even when you’re not sure of the lie — and commit to the shot. The ability to launch a venture or enter a new region (or new product line) while the enterprise is dealing with internal friction is a hallmark of American grit.
Lesson 2: Chipping from the Rough – Saturday, October 25
Saturday’s round found Trump traveling aboard Air Force One in Asia, announcing new tariffs on Canada, conducting diplomatic meetings in Qatar, and preparing the ground for deeper engagement in Asia. A highlight: his arrival into Malaysia triggered what was described as a “dance” with traditional performers at the welcome ceremony. Omni+2Al Jazeera+2
Business/leadership takeaway: The short game is where the margin for error is tightest. On the golf course, your chip shot can salvage a par or lead to bogey. In business, when you’re mid-project, you’re often in the rough: the terrain is unclear, alliances are shifting, tariffs and trade deals can upend assumptions.
- Announcing additional Canadian tariffs is like repositioning your strategy mid-round.
- Diplomacy in Qatar while en route: multitasking under pressure.
- The “celebratory dance” in Malaysia: the importance of cultural fluency and optics — in business, you don’t just deliver results, you build relationships and show respect.
From our “Golf with THE Chuck” perspective: when you find yourself in the rough, resist the panic of just hitting. Instead, assess the lie, take the smart club, respect the conditions, and focus on alignment. The chip is not about brute force—it’s finesse. American grit isn’t only about powering through; it’s also about adapting in the moment while staying focused on the hole.
Lesson 3: Putting for Purpose – Sunday, October 26
On Sunday, the scene was in Kuala Lumpur, Malaysia, at the Association of Southeast Asian Nations (ASEAN) summit. Trump oversaw the ceremonial signing of the Kuala Lumpur Peace Accord between Thailand and Cambodia, and engaged in trade diplomacy with Malaysia, Canada, and China. Ministry of Foreign Affairs Malaysia+3Wikipedia+3Wikipedia+3
Business/leadership takeaway: The putt is often the most nerve-wracking shot. The green is smooth, deceptively simple—but one misread and you’re off. In business, the finishing moves matter: the deal, the contract signing, the handshake. Sunday is where you convert the weekend’s work into tangible outcomes.
- The peace accord: diplomacy turned into deliverable.
- Trade framework with China: tentative, but purposeful.
- The optics of dancing with local performers: the finishing touch that builds goodwill beyond the metrics.
From Chuck’s fairway: when you’re standing over the putt, you’ve already done the prep (the tee shot, the chip). Now you align your stroke with purpose: aim for the hole, read the break, trust your stance. That’s the moment when enduring American grit shines—not because you yelled loudest, but because you executed calmly in the zone.
Summary
This October 24–26 stretch reads like a legendary loop:
- Tee boldly with leadership under pressure (Friday)
- Chip from the rough of international trade and diplomacy (Saturday)
- Putt with purpose as deals come to fruition (Sunday)
The broader theme: grit is not always about raw force. It’s discipline, focus, cultural awareness, and readiness to perform when the lie is imperfect and the stakes are high. That’s what the weekend’s events with President Trump’s Asia tour illustrate, and that’s what “Golf with THE Chuck” is all about—bringing lessons from the course to the boardroom and beyond.
Wrap-up
May this week remind you: whatever fairway you’re navigating—startup, nonprofit, team leadership, or personal legacy—stay in your stance, commit when you must, adapt when needed, and finish with integrity. American grit doesn’t retire when the job gets harder—it shows up.
See you next week for our next edition. May your golf swing be steady, your business moves strategic, and your legacy worthy.
— Chuck Cordak
Be sure to bring your driver, your wedge, and your putter to the game of life.
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