For ambitious professionals, saying “no” is a celebrated strategic act. We use the “Strategic No” to reclaim our time, prune our commitments, and simplify our lives. It’s a powerful feeling of control and liberation.
But what about the day after?
What happens when the relief of a clear calendar fades and you’re left with a quiet, unnerving silence? I call this “The Void.” It’s a space where the lack of busyness can trigger a low-grade panic. We’ve been conditioned for decades to be doing, and this new openness can feel like a vacuum.
The common advice is to wait—to hold out for that one, perfect, soul-defining “Hell Yes!” opportunity.
I believe this is a trap. Waiting for perfection is a form of analysis paralysis. For senior professionals in transition, the real danger isn’t making a bad move; it’s making no move at all. This is the “Risk of Rusting.” Our identity, skills, and professional momentum don’t just pause; they can atrophy.
This is why I’m focusing the new issue of my newsletter, Personal Strategy Compass, on a different path: the Strategic Probe.
If the “Strategic No” is about simplification, the “Strategic Probe” is about intelligent exploration. It’s the permission slip to be messy and non-linear. A probe is a small, safe-to-fail, low-cost experiment designed to generate one thing: a Return on Information.
- Instead of launching a new business (a plunge), you have three 30-minute calls to test the idea (a probe).
- Instead of committing to a board (a plunge), you offer to advise one of their sub-committees for a single project (a probe).
This approach moves you from a state of passive waiting to active, intelligent discovery. It’s a core practice in my Personal Quarterly Offsite (PQO), where I shift from being a CEO who prunes to a Venture Capitalist who seeds a portfolio of small bets.
This month, I’m running an experiment of my own. I’m making Issue #11 an “Open House”—the main body is completely free for all readers. And that includes you. I reporduce the newsletter below.
Inside, I share:
- My “Strategic Probe Matrix,” a 2×2 framework for designing your own experiments (and avoiding “Ego Traps”).
- An AMA on managing the financial and identity risk of an encore career.
- A Personal Reflection on my recent solo camping trip and the difficulty of embracing “strategic wandering.”
The only section reserved for premium members is the AI Strategy Corner, a custom-built prompt to help you design your own probes.
This is your invitation to run a probe on the newsletter itself. There’s no risk, and the potential Return on Information is high.
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Personal Strategy Compass Issue #11: October 2025
The Strategic Probe: What to Do in the Space After ‘No’
A quick note for subscribers to the free version and new readers:
Welcome to a special “Open House” edition of Personal Strategy Compass.
The theme of this issue is experimentation, so I’m running an experiment of my own. For this month only, I’m making the main body of this issue, from the introduction to the closing manifesto, available to all readers.
I’m doing this because this month’s topic feels universal. It’s for anyone who has ever created space, only to be met with a quiet, unnerving silence.
My ”Open House” hypothesis is that once you see the full value I provide in each issue, the decision to subscribe will be an easy one. The only section reserved for premium members this month is the AI Strategy Corner at the very end.
With that, let’s get started.
TABLE OF CONTENTS
- Welcome & Introduction
- The Hidden Risk of Standing Still
- Ask Me Anything: Managing Transition Risk
- Personal Reflection: My ‘Yes’ to Strategic Wandering
- Activation Toolkit: Your KIPL Probe Worksheet
- Tip of the Month: Probe vs. Plunge
- PQO as a Practice: Your Quarterly VC Meeting
- Recommended Resource
- Closing Thoughts & The Explorer’s Manifesto
- Your Next Strategic Move
- [PREMIUM SUBSCRIBERS ONLY] AI Strategy Corner: Worth the Price of Admission Alone
Welcome & Introduction
The Peril of the Blank Slate
Saying no is a relief. It’s a clearing. A clean slate. For a moment, it feels like absolute freedom.
Then, a quiet panic can set in. I call it The Void. The space you fought so hard to create can feel less like an opportunity and more like an unnerving silence. We’ve been conditioned to be busy, and a blank calendar can be deeply unsettling.
The common advice is to wait for a “Hell Yes!” But what if that’s a trap? How many times have you actually seen an unreserved “Hell Yes!” in the wild? And if you saw one, would you say, “Hell Yes!” without doing your due diligence?
This issue offers a different path for your Personal Quarterly Offsite (“PQO”) practice. It’s an explicit permission slip to be messy and non-linear.
We’re going to invert the logic of Issue #10. If the “Strategic No” was about simplification, this is about strategic exploration. This is about the Strategic Probe. That’s a small, intelligent “yes” that generates a Return on Information and is the only real antidote to analysis paralysis.
The Hidden Risk of Standing Still
Inverting the Cost of Yes
Last month, we audited the hidden costs of saying yes rather than saying “no” strategically. Now, let’s examine the hidden risks of standing still.
- From “Commitment Debt” to “Opportunity Cost.” Every no to exploration accrues an Opportunity Cost. By waiting for the perfect option, you are paying a steep price: the loss of new knowledge and the stagnation of your identity.
- From “Cost of Carrying” to the “Risk of Rusting.” We talked about the mental load of carrying old commitments. The inversion is the Risk of Rusting in place. An identity built on being an “innovator” cannot be sustained by inaction. Without new learning curves, your core capabilities can atrophy.
- From Pruning to Seeding. The CEO prunes. The Venture Capitalist seeds. Your job has changed. It’s no longer about ruthless efficiency; it’s about intelligent discovery. Your role is to make small investments of time and energy in a portfolio of potential futures.
Taken together, these three inversions reveal a critical truth: the riskiest move is not making a bad bet, but failing to make any bets at all. The strategic imperative is not to find the one perfect “Hell Yes!” Instead, it is to begin building a portfolio of small, intelligent probes. The following sections provide the frameworks to do just that.
Ask Me Anything: Managing Transition Risk
Tackling the Biggest Barrier to Your Next Chapter
Q: “I’ve used the Strategic No to clear my plate, but I still feel anxious about leaving my high-income partner role for an encore career. How does the PQO help me manage the financial and identity risk associated with winding down a practice I spent 30 years building?”
A question I often hear from high-achieving senior lawyers is: “How do I make a change without risking everything I’ve built?” This is where the PQO shifts from a planning tool to a risk-mitigation dashboard. We don’t leap; we build a bridge, one quarterly plank at a time. Your PQO is where you de-risk the transition by running small, low-cost experiments. Instead of quitting to become a consultant, you use one PQO cycle to land a single, paid pilot project. You test the market, your messaging, and your own enthusiasm for the work before making an irreversible decision.
Financially, the PQO is where you model the future. You define the specific revenue targets your “encore career” needs to hit and work backward, setting quarterly milestones. This transforms a terrifying financial unknown into a manageable, measurable project. Identity risk is managed the same way. Use your PQO to intentionally build your new identity (e.g., “Board Advisor”) through concrete actions long before you shed the old one. Remember, your PQO is the place where you have permission and space to create Risk-Managed Transition Plans, ensuring your legacy and your financial stability are protected throughout your strategic career evolution.
Personal Reflection: My ‘Yes’ to Strategic Wandering
Why I Had to Get Comfortable with Being Uncomfortable
After retiring from Michigan State University, my instinct, honed over decades, was to immediately engineer a master plan. My PQO, however, led me to a counter-intuitive conclusion: the most strategic “yes” I could make was a “yes” to not knowing.
I took a solo camping trip on my family’s farm immediately after my last day at MSU a few weeks ago. My instinct was to pull out a notebook and force a plan and resisting that urge was surprisingly difficult. That discomfort was the whole point. It was an act of strategic wandering, allowing me to detach from the need for certainty. The big “yes” wasn’t to a project. Instead, it was to a process of exploration. I’ll be drawing from the lessons I learned on that camping trip for a long time to come.
Activation Toolkit: Your KIPL Probe Worksheet
A 4-Quadrant Matrix for Designing Safe-to-Fail Experiments
The best way to move forward is to manage a portfolio of small, safe-to-fail experiments. Use this matrix to map out your probes. Your goal is to focus on the “Smart Probes” quadrant.
STRATEGIC PROBE MATRIX
| LOW RESOURCE COST | HIGH RESOURCE COST | |
| HIGH LEARNING | SMART PROBES (GO!) (Small, reversible experiments) Write 1 article on new topic Take 3-hour online course | PLUNGES (USE CAUTION) (Bigger bets made after probes) Launch paid newsletter Major certification program |
| LOW LEARNING | MAINTENANCE TASKS (LIMIT) (Familiar, but little growth) Coffee with former colleague Attend standard industry update | EGO TRAPS (AVOID!) (High effort, low insight) Unpaid board for unaligned cause Obligatory, draining projects |
A Probe in Practice: Let’s say your hypothesis is to become a board advisor. A ‘Smart Probe’ isn’t applying to boards; it’s having one 30-minute call with a search firm recruiter to learn about the market. Cost: 1 hour. Return on Information: Massive. The “plunge” step might be to read a whole board on serving on a board or even applying for two board positions to gather data.`
Tip of the Month: Probe vs. Plunge
Before committing to a new “yes,” ask this one question: “Is this a probe or a plunge?” A probe is a small, reversible experiment designed to get information. A plunge is a large, hard-to-reverse commitment. This season of your career is for probing, not plunging, first.
PQO as a Practice: Your Quarterly VC Meeting
Reframe your Personal Quarterly Offsite. It is now your Quarterly Venture Capital Meeting. This is where you:
1. Review the Portfolio: Assess learnings from last quarter’s probes.
2. Kill, Pivot, or Persevere: Decide which bets to abandon, modify, or double-down on.
3. Allocate New Capital: Approve a new “seed fund” of time for the next quarter’s portfolio of Smart Probes.
There is the start of your next PQO agenda.
Recommended Resource
Disrupt Yourself: Putting the Power of Disruptive Innovation to Work by Whitney Johnson. This is the essential guide to applying the S-Curve framework, famous in business innovation, to your own career trajectory. Johnson brilliantly reframes career growth as a series of learning curves we must intentionally jump between to avoid stagnation. It’s a perfect strategic companion for anyone designing their next chapter and a great framework for thinking about smart probes.
Closing Thoughts & The Explorer’s Manifesto
The ultimate freedom of the “Strategic Yes” isn’t refilling your calendar with new tasks. It’s earning the capacity to place your own bets.
The Manifesto for the Strategic Explorer:
- Value learning over certainty.
- Favor probes over plunges.
- Gather data, don’t just introspect.
- Seek a Return on Information.
- Embrace the messy middle.
This points us to a new operating system for this season of your professional life. For decades, our success was defined by having the right answers and a clear five-year plan. The work now is to get comfortable asking the right questions and running the small, reversible experiments that bring back valuable data. Your next great chapter won’t be revealed in a flash of magical “Hell Yes!” insight. It will be assembled, piece by piece, from the knowledge you gain with your very next probe.
A strategic probe is the purest expression of your curiosity.
Your Next Strategic Move
This entire issue has been about the power of a Strategic Probe.
Reading this “Open House” edition was your first probe into Personal Strategy Compass. You now have the data. You’ve seen the frameworks, the personal reflections, and the step-by-step toolkits I deliver to my premium members every single month.
If your probe was successful—if you found yourself nodding along, saving that matrix, or feeling understood—then the next logical step is to move from a probe to a commitment.
This “Open House” was a one-time experiment. Next month, this level of access goes back behind the paywall, and we’ll be discussing the next step: From Probe to Pilot.
Upgrading to premium is your “Strategic Yes.” It’s your commitment to stop the “Risk of Rusting” and start actively building your next chapter. It’s also the only way to get the one tool we held back, which you’ll see below.
- Upgrade to Premium: Get the AI Strategy Corner every month and ensure you don’t miss next month’s issue. A single good idea from one issue can deliver a 10x return on your investment. Subscribe to Premium Edition
- Share with a Colleague: Or, if your probe tells you this is for someone else, the most powerful way to support this work is to forward this “Open House” edition to one colleague who is staring into “The Void” of their own.
The AI Strategy Corner: The One Section Worth the Price of Admission
Premium subscribers only
This is the only section of this month’s issue exclusive to premium members. Each month, you get a custom-built, advanced prompt to use as a strategic tool. This prompt alone can save you hours of indecision and help you design stronger experiments. It’s your personal AI venture partner.
[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]
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