The Sailor's Logbook
Ten Stories In: What I've Learned, What I'm Adjusting, and What's Next
Ten Stories In: What I’ve Learned, What I’m Adjusting, and What’s Next
🌊 The Story
In sailing, you keep a logbook. Every hour or so, you make an entry: position, course, wind speed and direction, sea state, any notable events or decisions.
I remember a crossing of the English Channel where this practice helped us with decision making. We had a destination in mind, a plan to get there. The weather forecast looked favorable for the crossing.
But a few hours in, the wind started shifting earlier than predicted. Our speed dropped. We kept making the hourly entries: position, speed over ground, wind direction. Each entry told the same story—we were falling behind the plan.
Photo by Michal Balog on Unsplash
By the fourth or fifth entry, the pattern was undeniable. The wind had turned, and it wasn’t turning back. We weren’t going to make our original destination, at least not safely or comfortably.
The decision wasn’t easy. We’d set out with a clear goal. Changing destination mid-crossing felt like admitting defeat. But the logbook didn’t lie. The entries laid out the reality: this is where you are, this is your actual speed, this is what’s possible from here.
We changed course to a closer harbor. It wasn’t the plan, but it was the right call given what reality had taught us.
Without those regular position checks—without writing down where we actually were versus where we’d planned to be—we might have pushed on toward the original destination. Pride keeping us committed to a plan that would stretch us too hard, waste our energy and resources for nothing.
The logbook forced us to see what was actually happening, not what we wanted to be happening. And that’s what made the smart decision possible.
Ten articles into Leading with Stories, I’m doing the same thing—checking position, looking at what’s actually happening versus what I planned.
Not because something’s wrong, but because this is when the discipline matters most—when momentum is building and you could easily just keep going without pausing.
Here’s what ten weeks of data reveals—patterns that might matter if you’re building something similar:
The data doesn’t reveal clear patterns yet. Ten articles in, here’s what I see: “Make it Black and White” hit 1,301 LinkedIn impressions and 88% open rate. “The Sock in the Washing Machine” got 253 Substack views. “Just Be Yourself” reached 898 impressions. Meanwhile “Let Go, Trust Your Feelings” only hit 277 impressions, and “Cathedral That Floats” got 51 Substack views despite having concrete, actionable advice.
What’s the pattern? I honestly don’t know yet. Is it the topics? The titles? The Tuesday morning timing? The fact that my best performer was published on a holiday? With ten data points, I can’t tell signal from noise. But that’s exactly why these regular checks matter—I’m building awareness of what’s happening, even if I don’t understand why yet.
Weekly publishing forces movement over perfection. The constraint of “this ships Tuesday” prevents perfectionism paralysis. I have to decide: What’s the core insight? What’s the clearest way to express it?
Good enough—ship it.
Are my articles too long? Probably. Are they perfect? Definitely not. But my goal isn’t the Pulitzer. It’s getting decent stories out consistently, building the discipline of regular reflection and writing.
Tuesday morning publishing—right choice or just habit? Honestly, I have no idea. It felt like a reasonable time when I started. The data doesn’t tell me if it matters. Another thing to test eventually.
Readership is nice; engagement beyond my circle is better. Of course I enjoy seeing the open rates and view counts. But what really energizes me is when someone I don’t know engages—a comment from a stranger, a share from someone outside my network, a conversation that starts because the story resonated with someone new. That’s when I know these frameworks are spreading beyond my immediate sphere.
What’s next: writing for a larger audience. My next step isn’t just writing more—it’s actively reaching beyond my existing network. Engaging on Substack, not just posting. Mixing in tactical Business Development case studies alongside leadership frameworks.
Being intentional about growth, not just production. Because ultimately, I’m doing this for exchange, learning, teaching, connection, and inspiration. That requires more people in the conversation, not just better content for the same audience.
What I need from you: Read. Engage. Comment. Share the stories that resonate. Tell them in your own conversations when they’re useful. That’s how these frameworks spread—through people finding them helpful enough to pass along.
This is a long journey with more position checks ahead. I’m not trying to become anything special—just want my stories out there and the discipline to keep writing them. And I’m genuinely happy when someone tells me a story helped them think differently about a challenge they’re facing.
💼 The Business Reality: When to Check Your Position
Position checks aren’t just about catching problems. They’re about spotting opportunities that only become visible when you stop to look—and identifying what’s working so well you should amplify it.
The discipline combines two practices: regular logging (recording what’s happening as you go) and periodic position checks (stepping back to look at patterns). The first creates the data. The second extracts the insight.
The Scale-up Founder at the Growth Inflection
You’ve found product-market fit, raised funding, hired a team. Revenue is growing. The early chaos is settling into a real business. The temptation: keep executing the playbook that got you here.
The position check reveals: Are these the right customers for scale? Can you actually make money at these economics? Which early scrappy approaches need to professionalize, and which should you protect? What’s working better than expected—which team members, which customer segments, which approaches deserve more investment?
The Consultant Whose Calendar Is Full
You left corporate. Clients are coming through your network. Your calendar is booked solid. You’re busy, successful by conventional measures.
The position check reveals: You review accounts receivable and invoicing. Clients are slow to pay. You’re doing unpaid extras. Scope creep is eating margins. Your effective hourly rate is depressing. A full calendar hides the problem: you’re busy but not profitable.
The CEO Whose Vision Is Aging
Your company has been successful. Strong market position, profitable operations, good team. But the world is changing. Customer expectations are shifting. New competitors operate differently. Technology is enabling business models that didn’t exist five years ago.
The position check reveals: What made you successful is becoming less relevant. The strategy that worked brilliantly in 2019 needs updating for 2025. Your advantage is eroding not because you’re executing poorly, but because the game itself is changing. Time to refresh the vision—not because you’re failing, but because staying relevant requires continuous recalibration.
The Common Thread
Position checks create space to learn from your own experience and spot what only becomes visible once you’re underway—opportunities to seize, problems to address, successes to amplify. They’re about making better decisions with the knowledge you’ve gained from doing the work, not just planning it.
🔬 The Science: Why Reflection Drives Performance
Research across multiple disciplines confirms that learning comes not from experience itself, but from reflecting on experience. The distinction matters because it explains why some professionals grow rapidly from their work while others repeat the same year of experience ten times over.
Experiential Learning and Reflection
David Kolb’s research on experiential learning established that learning follows a cycle: concrete experience, reflective observation, abstract conceptualization, and active experimentation. His studies show that people who skip the reflection stage—who move directly from experience to the next action—learn far more slowly than those who pause to extract meaning from what happened.
High performers in complex domains spend disproportionately more time in the reflection stage. They’re not slower to act—they’re more deliberate about learning from action before taking the next one.
Deliberate Practice and Feedback Loops
Anders Ericsson’s research on expertise reveals that what separates elite performers from competent ones isn’t just practice volume—it’s the quality of feedback loops. Experts deliberately create opportunities to assess their performance, identify gaps, and adjust their approach.
Position checks function as self-generated feedback loops. Instead of waiting for external evaluation, high performers actively create their own assessment moments. This self-directed feedback develops metacognitive awareness—the ability to observe and correct your own performance in real-time.
Growth Mindset and Learning Orientation
Carol Dweck’s research on growth mindset shows that individuals who view abilities as developable rather than fixed perform dramatically better long-term. Her less-discussed finding: growth-minded individuals actively seek information about their current performance level, while fixed-mindset individuals avoid it.
Regular self-assessment is both a cause and consequence of growth mindset. People who check position regularly develop stronger beliefs in their ability to improve, which makes them more likely to check position in the future—a virtuous cycle that compounds over years.
The Research Consensus
Across cognitive psychology and organizational behavior, the evidence points in the same direction: regular, structured reflection dramatically improves learning and performance. The professionals who build position checks into their rhythm don’t just work hard—they work smart, extracting maximum learning from each experience and spotting opportunities that pure execution misses.
🎨 The Art: How to Actually Check Your Position
The theory is simple. The practice requires discipline. Here’s what matters:
Start Logging From Day One
Don’t wait until you have “enough data.” Begin logging immediately—what you’re doing, what’s happening, what you’re noticing. Even if the first entries feel pointless, you’re creating the baseline that makes later position checks possible.
The log can be simple: a spreadsheet, a document, a notebook. What matters isn’t the tool—it’s the regular practice of recording where you are.
When to Check Position (Not Just Log)
Natural milestones work well. Ten articles published. First 100 customers. 90 days in a new role. End of a project phase. These are moments when you’ve accumulated enough experience to learn from.
Check too early, you’re reacting to noise. Check too late, you’ve drifted too far to correct efficiently.
Also recognize unscheduled check moments: When you’re spinning your wheels. When what worked last month stopped working. When success feels hollow. These signals say pause, even between milestones.
What to Look At
Compare intent to reality. What were you trying to accomplish? What actually happened? The gap is information.
Look for patterns, not single events. One data point means little. Five similar ones tell you something.
Notice accidental successes. What worked that you didn’t expect?
Check resource allocation. Where is your time and attention actually going—not where you planned, but where it’s actually flowing.
When to Adjust vs. Stay the Course
Adjust when: Data consistently shows your approach isn’t working. What you’re doing drains rather than energizes you. You’ve discovered new opportunities.
Stay the course when: It’s working but slower than hoped. You haven’t given it enough time. Early data is mixed but not definitively negative.
The discipline isn’t complicated. It just requires doing it.
💡 The Key Insight - TL;DR
Check your position regularly—not just when you’re struggling, and not just when you’re succeeding. Make it a discipline regardless of circumstances.
In sailing, experienced skippers don’t wait for problems to check the log. They do it on a schedule—every hour, every watch change, every milestone. Not because something’s wrong, but because that’s how you stay aware of what’s actually happening versus what you think is happening. The discipline of regular logging creates the data. The practice of periodic position checks extracts the insight.
Ten articles into Leading with Stories, my position check reveals progress and choices to make:
What I’ve learned:
Writing weekly forces decisions and movement—the Tuesday deadline prevents perfectionism paralysis
The act of structuring stories into frameworks reveals patterns I couldn’t see when they just lived in my head
I’ve focused these first ten weeks on proving to myself I could do this consistently, not on maximizing engagement
Working with AI sharpens my thinking when used as a thinking partner, not a replacement
I genuinely don’t know yet what makes certain articles perform better—ten data points isn’t enough to separate signal from noise
What I’m adjusting:
Moving from “can I do this?” to “how do I reach more people?”
Engaging actively on Substack, not just posting and moving on
Exploring different ways to share stories—not just the weekly article format
Being more intentional about growth while keeping the discipline
The practice for anyone building something
Start logging from day one, even before you have patterns to see. Check position at natural milestones—10 articles, 90 days, first batch of clients. Look for what’s working to amplify, not just problems to fix. Ask specific questions about what reality is teaching you. Adjust based on actual data, not hopes or fears.
What would help me
If these stories resonate with you, share them. Tell them in your own conversations when they’re useful. And tell me your own stories—the moments that taught you about leadership, the frameworks you’ve developed, the analogies that help you make sense of your work. Leading with Stories works best as a conversation, not a monologue.
What surprised me most
Writing ten stories taught me far more than I expected. Not just about storytelling, but about discipline—showing up weekly regardless of inspiration. About setting clear intent before starting each piece. About the value of regular reflection, not just constant production. About working with AI in ways that sharpen my thinking rather than replace it. And about engagement—the conversations with my existing network have been genuinely rewarding, and they’ve made me want to reach beyond that circle, to connect with people I don’t yet know.
The logbook works. Now to see what the next leg of the journey reveals.
This story has been anonymized to protect privacy, but the insights it contains are as real as the day they were discovered. Each one changed how I see some aspect of business, leadership, or life. I hope a few of them might do the same for you.
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