Welcome to the 75th edition of #theFutureReadyAdvisor Newsletter!
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The Whiteboard That Saved Apple
In the summer of 1997, Steve Jobs walked into an Apple product review meeting with the company 90 days from bankruptcy. His team expected a rallying speech about innovation, about fighting back against Microsoft.
Instead, Jobs grabbed a marker, drew a 2×2 grid on the whiteboard, and said: “We’re going to make four products. Consumer desktop. Consumer portable. Pro desktop. Pro portable. Everything else gets killed.”
The room went silent.
Apple had over 40 products in development. Engineers had spent years building these offerings. The existing plan called for diversification, for competing across multiple categories.
Jobs was ignoring all of it.
“But Steve,” someone protested, “we’ve invested millions in these product lines. The roadmap—”
Jobs cut him off. “The roadmap is why we’re dying. We’re going to make four great products instead of forty mediocre ones.”
Within a year, Apple was profitable. Within three years, they launched the iMac and changed personal computing forever.
This reset wasn’t abandoning Apple’s mission—making insanely great products. It was ruthlessly refocusing on what actually mattered.
Which brings me to my reset. This is the final edition of The Future-Ready Advisor newsletter in its current form. And like Jobs in that conference room, I’m about to explain why I’m ignoring the plan I started with three years ago—not because it failed, but because clinging to it would be the wrong move.
The Plan I Started With
When I launched this newsletter in May 2023, I had a clear plan: Write for financial advisors. Share insights on behavioral finance and client psychology. Publish bi-weekly. Build a modest following of practitioners.
The plan was working. Subscribers grew steadily. Engagement was solid.
But somewhere around edition 30, I noticed something: the readers who engaged most weren’t just advisors. They were CEOs, executives, consultants, entrepreneurs—leaders across industries facing similar challenges around decision-making under uncertainty.
The themes that resonated most weren’t the narrowly tactical ones about portfolio construction or even behavioral insights. They were the deeper leadership principles: how to navigate ambiguity, when to persist versus pivot, why teams resist change even when they know it’s necessary.
I had optimized the newsletter for yesterday’s vision. But the territory had changed. I needed to reset.
Three Lessons About When to Reset
Lesson 1: Plans Optimize for Yesterday’s Conditions
Early on, I wrote detailed pieces on behavioral finance concepts—prospect theory, loss aversion, mental accounting. These were solid: well-researched, tactically useful for client conversations.
The advisor audience engaged as expected. Open rates were fine. Comments were polite.
But something else was happening offline.
Consulting clients—CEOs, executives, leadership teams—kept referencing the editions that weren’t specifically about investing. The invisible gorilla experiment and what leaders miss when hyper-focused. The marshmallow test and delayed gratification in organizational culture.
“That piece you wrote about the Pittsburgh Steelers winning by doing simple things consistently?” a manufacturing executive told me. “I shared it with my entire leadership team. It’s exactly what we need to hear about operational excellence.”
Leaders in my network started forwarding editions to their teams, not because they were about financial advice, but because they addressed universal leadership challenges: decision-making under uncertainty, managing human behavior, navigating change.
My plan was optimized for one audience (financial advisors), but the work was resonating with a much broader one (leaders across industries facing similar human challenges).
Think about Intel’s Andy Grove moment in 1985. The memory chip business wasn’t failing catastrophically—Intel was still shipping product, still had customers. But Grove asked: “If we got kicked out and the board brought in a new CEO, what would he do?” The answer—pivot to microprocessors—required acknowledging that success in one market was masking a bigger opportunity in another.
The principle: Plans are maps, not territory. When the territory reveals itself to be larger than you mapped, you have a choice. Stick to the original boundary, or redraw the map to match actual terrain.
Lesson 2: Process Beats Outcomes (But Outcomes Reveal Which Processes Matter)
Initially, I measured newsletter success through typical metrics: open rates, click-throughs, subscriber growth. These didn’t tell me much about whether the work mattered.
Then readers started reaching out: “Your piece on the invisible gorilla changed how I run team meetings.” “I shared your Everest story in our leadership offsite—it reframed how we think about risk.”
These weren’t vanity metrics. They were signals that the process—writing to clarify thinking, distill complex ideas, provide practical frameworks—was creating real value.
Like John Wooden, I needed to focus on the inputs (writing quality, framework clarity, practical applicability) and trust that outcomes would follow.
But here’s the key: outcome feedback told me which inputs actually mattered. Low engagement on tactical advisor content told me to write less of it. High engagement on leadership principles told me to write more.
The principle: Focus on controllable inputs, but use outcome feedback to refine which inputs deserve your energy.
Lesson 3: The Best Resets Come from Strength, Not Weakness
When Netflix split its DVD and streaming businesses in 2011, it looked like desperation. Stock price collapsed 77%. Media declared it corporate suicide.
But Hastings, its CEO, wasn’t panicking—he was adapting from a position of strategic clarity. He saw streaming was the future, tried one path, realized it was wrong, and pivoted within weeks.
Contrast this with WeWork. They pivoted constantly—from co-working to “space as a service” to “community company” to whatever pitch worked with investors that week. Each reset came from weakness, from trying to escape fundamental problems.
I’m not rebranding because The Future-Ready Advisor failed. I’m evolving because it succeeded beyond its original scope.
The principle: Reset from a position of clarity about what’s working, not panic about what’s failing. Jobs didn’t kill 40 products because Apple was doomed; he did it because he had clarity about the four that could save them.
Three Questions Before Changing Course
Every leader faces the same tension I’ve faced with this newsletter: You need a plan. It provides direction and accountability. You also need to ignore your plan when conditions warrant. Rigid adherence in changing conditions is how organizations die.
The question isn’t whether to stick to the plan or change course. It’s knowing which one serves your mission at this moment.
1. Has the environment changed, or just my enthusiasm?
Real environmental shift: Market fundamentals altered, client needs evolved, competitive landscape transformed.
False signal: I’m bored, a competitor launched something shiny, the latest trend looks appealing.
For me: The environment changed—audience composition shifted, engagement patterns revealed different needs, book publishing created platform expansion opportunities. Not boredom, not chasing trends.
2. Am I abandoning the plan or evolving it?
Evolution: Core mission intact, methods adapting, building on strengths.
Abandonment: Chasing entirely new goals because the original one got hard, pivoting to an unrelated opportunity, starting over from scratch.
For me: Evolution, not abandonment. Still about navigating uncertainty with clarity and confidence. Still practical frameworks. Different containers, same essence.
3. Am I pivoting from strength or from fear?
From strength: “This is working, and there’s a bigger opportunity emerging.”
From fear: “This isn’t growing fast enough, try something else.”
For me: Pivoting from strength. Newsletter succeeding. Book launching with strong early response. The rebrand captures where the work is actually going.
What’s Staying, What’s Changing
Like Jobs’ 2×2 matrix—I am keeping what matters, and changing what doesn’t:
What’s Staying:
- Bi-weekly rhythm — every other Tuesday morning
- 5-7 minute read length
- Practical frameworks — tools you can use immediately
- Story-driven insights
- Free access — core content remains accessible to all
- My voice
What’s Changing:
- Brand name — The Future-Ready Advisor becomes The Uncertainty E.D.G.E.
- Platform — moving to Substack for full content (LinkedIn gets excerpts)
- Content depth — no character limits, complete frameworks, downloadable tools
- Audience — explicitly serving leaders across industries, including advisors
The Leader’s Reset
I started this newsletter thinking I was teaching what I knew. I discovered I was learning alongside you.
The irony isn’t lost on me: I’m writing about when to ignore your own plan while announcing that I’m ignoring my own plan. But that’s exactly the point.
The best leaders don’t stick rigidly to plans or abandon them at the first difficulty. They hold them lightly enough to adapt when conditions change, but firmly enough to maintain direction toward what actually matters.
Steve Jobs understood this in 1997. He didn’t save Apple by sticking to the existing plan or by pivoting aimlessly. He saved it by ruthlessly refocusing on what mattered: making insanely great products, just fewer of them, with total commitment.
This principle—knowing when to persist and when to pivot—runs throughout my latest book, The Uncertainty E.D.G.E.: Lead with Clarity, Adapt with Confidence, Win with Conviction, available now. https://books2read.com/theuncertaintyedge
The Uncertainty E.D.G.E. Newsletter launches January 13th
Starting January 13th, my newsletter continues under its new name in its new home on Substack. Substack provides a better home for the kind of work we do here: disciplined thinking, evidence-based insights, and practical decision tools for complex environments. You’ll receive the same strategic content—now delivered in a format built for depth and continuity.
The next edition will drop here on LinkedIn with the Substack subscription link, a preview of the first full The Uncertainty E.D.G.E. edition, and details on what’s coming in 2026.
Until then, I have a challenge for you: Review your own 2025 plans—business strategy, personal goals, team objectives. Which ones need to stay the course? Which ones need a reset?
More importantly: Are you making that call from clarity about what matters, or from confusion about what’s easy?
Sometimes the smartest leaders ignore their own plans—not because they lack commitment, but because they’re committed to something deeper than the plan itself.
Thank you for three years of reading, engaging, challenging, and sharing. The work continues. The mission deepens. The edge sharpens.
See you in January. Happy Holidays!!
