Personal Strategy Compass - January 2026 Issue
Navigating your success your way, one quarter at a time
Personal Strategy Compass - January 2026 (#13)
Honor Thy Error as a Hidden Intention
A Quick Note on This Newsletter
Starting this month, Personal Strategy Compass is now free for all subscribers.
I initially launched it as a premium newsletter, but that decision never quite sat right with me. This work is at its best when it’s open, shared, and useful to as many people as possible. That’s the direction I’m committing to.
If you were a premium subscriber, thank you. Your early support made this possible, and I’m genuinely grateful. From now on, all posts will be free for everyone. Paid subscriptions are now just a way to support the newsletter, not a requirement to read anything. If you’re currently paying and would prefer not to, you’re very welcome to switch to the free option; you’ll keep getting the full newsletter.
For those who would like to support the newsletter going forward, I’ll continue to offer an optional way to do so, entirely voluntary, no gates, and no pressure. The work itself will remain open. It’s my Open Source model.
Now, on to this month’s idea.
Opening Signal
Your brain is lying to you.
If you’ve ever sat down to plan a new quarter and felt an odd sense of déjà vu, you’re not alone.
You’re motivated. You have good information. You know what should work. And yet your plans keep circling familiar ground—small variations on strategies you’ve already tried.
This isn’t a discipline problem. It’s not a lack of ambition. It’s something subtler. Your expertise is doing its job too well.
When you know a field deeply, your mind defaults to proven patterns. That’s efficient, but it can quietly block genuinely new strategic moves. The challenge isn’t generating more ideas. It’s interrupting the ones you already trust.
The Core Insight: Why Expertise Becomes a Strategic Trap
Most professionals believe strategic progress comes from better analysis: more data, clearer goals, tighter plans.
But analysis has a blind spot. It works inside your existing mental framework. When you ask, “What should I do next?” your brain reliably serves up options that feel sensible because they’re built from what worked before.
That’s how you end up optimizing strategies that are no longer distinctive, energizing, or even relevant.
The real barrier to strategic renewal isn’t ignorance. It’s familiarity.
Artists have understood this for decades. When Brian Eno created Oblique Strategies, a deck of cryptic, paradoxical prompts. His goal was disruption, not inspiration. Each card was designed to interrupt habitual thinking and force a new angle of approach.
What turns out to be true in music and art is also true in professional life: breakthroughs rarely come from thinking harder. They come from thinking differently, often through deliberate constraint or disorientation.
The Pattern Interrupt: “Honor Thy Error as a Hidden Intention”
One Oblique Strategies card captures this perfectly:
“Honor thy error as a hidden intention.”
At first glance, it sounds almost indulgent. Why honor mistakes when strategy demands rigor?
Because what we label as “errors” often reveal something important we’ve been unwilling to admit.
· An abandoned project.
· A decision that never quite felt right.
· A strategy you tried and quietly walked away from.
Instead of asking, “How did I mess this up?” the card invites a different question:
What intention was this pointing toward that I didn’t yet have language for?
Seen this way, mistakes aren’t failures. They’re early signals and the hard evidence of a direction your rational planning hadn’t caught up with.
This reframing doesn’t excuse poor execution. It changes how you interpret friction. Discomfort becomes data.
The One Experiment: A 30-Minute Strategic Reframe
This approach works particularly well during your Personal Quarterly Offsite, when you have protected time to think without execution pressure. But you don’t need a formal PQO to benefit from it. If you’re planning a Personal Quarterly Offsite or simply feeling strategically stuck, try this:
Think of one decision, project, or direction from the past year that felt like a mistake or a misfire.
Set a 30-minute timer.
Write answers to just one question:
“If this wasn’t an error, what intention might it have been revealing?”
Don’t correct it. Don’t fix it. Just explore the possibility.
You’re not looking for justification. You’re looking for a pattern you may have dismissed too quickly.
Often, the most valuable strategic shift is permission to acknowledge what you were already moving away from. Once you have your answer from the card exercise, don’t act. Just let it percolate at the back of your brain for a week.
I’ve found that an AI prompt will allow you to generate a random Oblique Strategies card and walk you through the exercise by nudging you into areas to explore and allowing you to keep iterating. The follow-up query “Tell me more” can often open up insights and directions that are useful in unexpected and profound ways. I used this AI technique with the card that says only “Water” on it, and it turned into one of the most useful sessions I’ve ever had.
You might also draw a card before your Personal Quarterly Offsite and use it as a theme for your PQO or as the focus for one session. There’s still plenty of time for you to have a Q1 PQO for 2026.
A Personal Note
The card “Honor thy error as a hidden intention” surfaced for me in a very concrete way this month.
I initially launched Personal Strategy Compass as a premium newsletter. On paper, the decision made sense, but it never felt settled. When I sat with the card “Honor thy error as a hidden intention,” I stopped asking whether the pricing model was right or wrong and asked a different question: What intention was this discomfort pointing toward?
The answer was clear once I allowed myself to see it. I wanted this work to be open, shared, and useful to as many people as possible. 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 intention underneath.
That reframing changed the decision from something to fix into something to understand.
Closing Thought
Your next strategic breakthrough may not be hiding in a new idea.
It may be hiding in the thing you labeled a mistake and stopped examining.
As the card reminds us: honor the error. It might be trying to tell you something you’re finally ready to hear.
Resources
Oblique Strategies (online): https://stoney.sb.org/eno/oblique.html
Physical deck: https://oblique-strategies.com
What is a Personal Quarterly Offsite (PQO)?
A PQO is a dedicated block of time—typically 2-4 hours—where you step away from daily execution to think strategically about the next quarter. It’s the personal equivalent of a corporate offsite, with you as the focus, leader, and event planner, so it’s customized to your needs. The goal is clarity about where you’re investing your most valuable resource: your strategic attention.