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 you’re unfamiliar with Oblique Strategies, it’s a deck of cryptic prompts created by Brian Eno and Peter Schmidt to interrupt creative blocks. Each card offers a constraint or paradox designed to force you out of habitual thinking. Artists have used them for decades. I’ve found them equally powerful for professional strategy.

The card made me stop and ask a different question. Not “Was the premium model right or wrong?” but “What intention was my discomfort pointing toward?”

The answer became obvious once I allowed myself to see it. I wanted this work to be open, shared, and useful to as many people as possible. My Open Source ethos isn’t just an idea I believe in. It’s how I now want to operate.

Making the newsletter free wasn’t a correction. It was an alignment. The “error” wasn’t the launch itself, but trying to force a model that didn’t match the underlying intention.

To everyone who supported the newsletter as a premium subscriber over this past year: thank you. Your early support made it possible for me to develop this work and find clarity about what it should be. I’m genuinely grateful.

This Month’s Issue: Using Oblique Strategies in Your PQO

Which brings me to the January issue, now available to everyone.

It’s about using Oblique Strategies during your Personal Quarterly Offsite (PQO). PQOs are dedicated 2-4 hour blocks where you step away from execution to think strategically about the next quarter.

The core insight: Your expertise creates invisible cognitive loops. When you sit down to plan, your brain automatically serves up variations of strategies you’ve already tried. You get incremental thinking disguised as breakthrough.

Oblique Strategies interrupts this pattern. The cards don’t give you answers. Instead, they force you to see your challenges from angles your expertise wouldn’t naturally surface.

The issue walks through:

  • Why constraints generate breakthroughs (and why “thinking harder” rarely does)
  • A simple 30-minute exercise using “Honor thy error as a hidden intention”
  • How to integrate Oblique Strategies into your quarterly planning
  • Real examples from my own practice

If you’ve been feeling stuck recycling the same strategic moves, or if your quarterly planning sessions feel more like obligation than discovery, this issue offers a different approach.

What’s Next

Personal Strategy Compass will remain free and open going forward. For those who’d like to support the work, I’ll offer an optional way to do so—entirely voluntary, no gates, and no pressure.

The newsletter itself stays accessible. That’s the model I’m committing to.

You can read the January issue here: https://dennis538.substack.com/p/personal-strategy-compass-3d9

And if you’re curious about Oblique Strategies, try drawing a card before your next planning session. You might be surprised what surfaces.

[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]

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