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Reflection:
Why We Choose to Stay in the Weeds |
Whacking weeds at Stately Freeberg Manor
Owner Operating Style Quiz (Which one are you?)
Answer honestly. There are no right or wrong answers. Your result helps determine whether you’re operating as a Crisis Junkie, Weed Dweller, Aspiring Operator, or Strategic Builder — and what to do next.
July 16, 2025
Several lifetimes ago, I was a restaurant waiter. I wasn't very good at it. If I had more than four full tables, I would fall "into the weeds." That's Restaurant Speak for falling behind. Then patrons become impatient and hostile, they complain. It's stressful and embarrassing. I knew some waiters and waitresses who could handle six, seven, eight tables at once. They were fabulous multitaskers who made some pretty enviable tip income. I admired them.
Now I think of any kind of "falling behind" as being "in the weeds." They might be sales orders. They might be that jammed email in box with 10,000 messages in it. It might be the honey-do list. It might be deferred maintenance on your house or your car. It might be a pile of debt. It might be that cluttered garage or basement, or both. It amounts to some pile of unkept promises that causes anxiety, stress, and shame.
As an Economist, I specialize in identifying and crushing bottlenecks to improve throughput and catch up on all that stuff. You might say I'm a "Weed Control Specialist."
I've been doing it a long time (officially 29 years as of this writing, and unofficially, longer). After all that time and experience, I've noticed a strange thing:
Some people seem to want to stay stuck in the weeds. It's their comfort zone.
At first, this comes as a strange surprise to me. But upon reflection, I have one of those "aha" "I could have had a V-8" moments and I realize, the reason this person remains stuck in the weeds, the reason he or she dabbles half-heartedly in solutions, the reason he or she is so good at "Creative Avoidance" is because that is where he or she is most comfortable.
I mean, think about it: what would you do if you were all caught up? All would be dead silence. Zero in box. No ringing phone. Just you alone with your thoughts.
And then what I call The Big Questions would creep into your mind. Questions like, "Who am I?" "Where have I been, where am I going, and why?" "Why are we here?" "What is life's purpose?" "Is there a God?" "Where do babies come from?" "How can bumblebees fly?" and so on. (Well, maybe you know the answer to one of them.)
There are other daunting questions many of us would rather avoid, like the twenty-two on this list: big financial goals that many of us find overwhelming.
Yes, like small talk, minutiae can be comforting. However, it can also keep us small, stuck in an endless cycle of self-defeat.
Mom. I remember when my mom was alive, she owned a small secretarial services business called The Paper Crunch. For her, it was a way to pay some bills, but it was also a diversion from some pretty acute personal pain.
I helped her untangle her books and catch up on payroll taxes. One day, while I was there, I put my hand on her shoulder and asked, "Mom, where do you want to be in five years?" I was sincerely interested in her vision for the future of the business, her aspirations for growth and development.
She broke down in tears and angrily snapped back at me, "Right here! I want to be right here!"
(A few years later, she was dead, at age 59, of brain cancer. I think she knew she wouldn't live five more years, and that is one reason why she cried. I also believe she grew a tumor from worrying, and from trying to reconcile irreconcilable ideas in her mind, like mixing oil and water, instead of facing facts. Cognitive dissonance killed her.)
In other words, she didn't want to grow; she didn't want to develop; she didn't want any change at all. She wanted to stay inside her comfort zone, inside the comfortable little routine she had set up for herself, to divert her attention from the pain. And in asking the question, I touched a wound that I didn't realize was there, until I saw her tears.
The Doctor is In. I began Making End$ Meet with inexperience and idealism. Let's set goals and achieve them. Pretty straightforward. Also pretty naïve.
Now I approach my work more with the mentality of a physician. Where does it hurt? Let's fix that, then hope that relieved pain will result in a more expansive mindset, making contemplation of the bigger questions and goals possible.
But sometimes it never happens. Regardless what I do, regardless what problems I solve or what pain I relieve, the patient just generates more minutiae, more weeds, and avoids addressing The Big Questions.
At this point, the care I provide become palliative. OK, we'll never answer the Big Questions or set & pursue the Big Goals. Let's just minimize pain and avoid calamity. Perhaps that is all that can be hoped for.
I'm not going to lie. When I reach that realization, I'm disappointed. I have big hopes and dreams for everyone. I believe in unbounded human potential. I believe we're all created in God's image and likeness, containing a divine spark, capable of the infinite.
And, it'd be nice to have some bragging rights: "Look at this wildly successful client! Look at those multiplied revenues and profits! I helped make that happen, aren't I awesome?"
Yes, that is what I hope and strive for. But people can be people: self-defeating, in their own way. And so, I must confess, that while we have enjoyed some of the above-described successes, what I have also seen is this phenomenon of Choosing the Weeds, of wanting to remain in that Comfort Zone.
In either case, I rejoice in progress, but I also understand mortal constraints and comfort zones. I am certainly not in the string-pushing business. There has to be energy on the other end of the string; and if there isn't, well, the best I can do is defense, damage control, loss prevention, pain relief . . . palliative care.
It is as if they're saying, "I say I want a CFO, but what I really want is a Paramedic."
I'd rather be on the offense. I'd rather be proactive and strategic. That's the fun stuff.
But sometimes, people just aren't ready, and maybe they'll never be. When they aren't, it's pathetic and disappointing, right? Would you really wish that on yourself, or on anyone you cared about?
So what does it take? What's necessary to surmount that torpor, that despair, and really take the bull by the horns and win big?
Often, I find that such a breakthrough happens on the other side of some kind of personal crisis. But must we really wait for the crisis? Isn't that also pathetic?
I like to believe that it's possible to just wake up one day and choose.
I hope this reflection helps someone out there do precisely that. Don't wait for the crisis. Just choose, and act.
My friend Paul Akers did that. He's a Lean Guru. He talks about "keeping the rope tight." He's highly disciplined.
It involves becoming somewhat of a freak with a Zero Tolerance attitude. Get that in box to zero. Eliminate all waste. Wake up. Think critically. If you're behind, don't tolerate that mess. Don't live like it's normal. Clean up and catch up on whatever it is.
I know that's how it's done. I've seen people do it. I've done it myself.
It's a decision.
Now it's your turn. What is your decision? Stay stuck in the weeds because they're comfortable and familiar distractions from life's Big Questions, or rise above them, grow and develop into a better version of yourself who can be a blessing to the world?
The choice is yours.
If you'd like help crushing those bottlenecks, getting out of the weeds and staying out, and living a big life crushing big goals, please give me a shout. I can help.
The first step is that complimentary Lifetime Savings Plan. Give it a whirl!
Several lifetimes ago, I was a restaurant waiter. I wasn't very good at it. If I had more than four full tables, I would fall "into the weeds." That's Restaurant Speak for falling behind. Then patrons become impatient and hostile, they complain. It's stressful and embarrassing. I knew some waiters and waitresses who could handle six, seven, eight tables at once. They were fabulous multitaskers who made some pretty enviable tip income. I admired them.
Now I think of any kind of "falling behind" as being "in the weeds." They might be sales orders. They might be that jammed email in box with 10,000 messages in it. It might be the honey-do list. It might be deferred maintenance on your house or your car. It might be a pile of debt. It might be that cluttered garage or basement, or both. It amounts to some pile of unkept promises that causes anxiety, stress, and shame.
As an Economist, I specialize in identifying and crushing bottlenecks to improve throughput and catch up on all that stuff. You might say I'm a "Weed Control Specialist."
I've been doing it a long time (officially 29 years as of this writing, and unofficially, longer). After all that time and experience, I've noticed a strange thing:
Some people seem to want to stay stuck in the weeds. It's their comfort zone.
At first, this comes as a strange surprise to me. But upon reflection, I have one of those "aha" "I could have had a V-8" moments and I realize, the reason this person remains stuck in the weeds, the reason he or she dabbles half-heartedly in solutions, the reason he or she is so good at "Creative Avoidance" is because that is where he or she is most comfortable.
I mean, think about it: what would you do if you were all caught up? All would be dead silence. Zero in box. No ringing phone. Just you alone with your thoughts.
And then what I call The Big Questions would creep into your mind. Questions like, "Who am I?" "Where have I been, where am I going, and why?" "Why are we here?" "What is life's purpose?" "Is there a God?" "Where do babies come from?" "How can bumblebees fly?" and so on. (Well, maybe you know the answer to one of them.)
There are other daunting questions many of us would rather avoid, like the twenty-two on this list: big financial goals that many of us find overwhelming.
Yes, like small talk, minutiae can be comforting. However, it can also keep us small, stuck in an endless cycle of self-defeat.
Mom. I remember when my mom was alive, she owned a small secretarial services business called The Paper Crunch. For her, it was a way to pay some bills, but it was also a diversion from some pretty acute personal pain.
I helped her untangle her books and catch up on payroll taxes. One day, while I was there, I put my hand on her shoulder and asked, "Mom, where do you want to be in five years?" I was sincerely interested in her vision for the future of the business, her aspirations for growth and development.
She broke down in tears and angrily snapped back at me, "Right here! I want to be right here!"
(A few years later, she was dead, at age 59, of brain cancer. I think she knew she wouldn't live five more years, and that is one reason why she cried. I also believe she grew a tumor from worrying, and from trying to reconcile irreconcilable ideas in her mind, like mixing oil and water, instead of facing facts. Cognitive dissonance killed her.)
In other words, she didn't want to grow; she didn't want to develop; she didn't want any change at all. She wanted to stay inside her comfort zone, inside the comfortable little routine she had set up for herself, to divert her attention from the pain. And in asking the question, I touched a wound that I didn't realize was there, until I saw her tears.
The Doctor is In. I began Making End$ Meet with inexperience and idealism. Let's set goals and achieve them. Pretty straightforward. Also pretty naïve.
Now I approach my work more with the mentality of a physician. Where does it hurt? Let's fix that, then hope that relieved pain will result in a more expansive mindset, making contemplation of the bigger questions and goals possible.
But sometimes it never happens. Regardless what I do, regardless what problems I solve or what pain I relieve, the patient just generates more minutiae, more weeds, and avoids addressing The Big Questions.
At this point, the care I provide become palliative. OK, we'll never answer the Big Questions or set & pursue the Big Goals. Let's just minimize pain and avoid calamity. Perhaps that is all that can be hoped for.
I'm not going to lie. When I reach that realization, I'm disappointed. I have big hopes and dreams for everyone. I believe in unbounded human potential. I believe we're all created in God's image and likeness, containing a divine spark, capable of the infinite.
And, it'd be nice to have some bragging rights: "Look at this wildly successful client! Look at those multiplied revenues and profits! I helped make that happen, aren't I awesome?"
Yes, that is what I hope and strive for. But people can be people: self-defeating, in their own way. And so, I must confess, that while we have enjoyed some of the above-described successes, what I have also seen is this phenomenon of Choosing the Weeds, of wanting to remain in that Comfort Zone.
In either case, I rejoice in progress, but I also understand mortal constraints and comfort zones. I am certainly not in the string-pushing business. There has to be energy on the other end of the string; and if there isn't, well, the best I can do is defense, damage control, loss prevention, pain relief . . . palliative care.
It is as if they're saying, "I say I want a CFO, but what I really want is a Paramedic."
I'd rather be on the offense. I'd rather be proactive and strategic. That's the fun stuff.
But sometimes, people just aren't ready, and maybe they'll never be. When they aren't, it's pathetic and disappointing, right? Would you really wish that on yourself, or on anyone you cared about?
So what does it take? What's necessary to surmount that torpor, that despair, and really take the bull by the horns and win big?
Often, I find that such a breakthrough happens on the other side of some kind of personal crisis. But must we really wait for the crisis? Isn't that also pathetic?
I like to believe that it's possible to just wake up one day and choose.
I hope this reflection helps someone out there do precisely that. Don't wait for the crisis. Just choose, and act.
My friend Paul Akers did that. He's a Lean Guru. He talks about "keeping the rope tight." He's highly disciplined.
It involves becoming somewhat of a freak with a Zero Tolerance attitude. Get that in box to zero. Eliminate all waste. Wake up. Think critically. If you're behind, don't tolerate that mess. Don't live like it's normal. Clean up and catch up on whatever it is.
I know that's how it's done. I've seen people do it. I've done it myself.
It's a decision.
Now it's your turn. What is your decision? Stay stuck in the weeds because they're comfortable and familiar distractions from life's Big Questions, or rise above them, grow and develop into a better version of yourself who can be a blessing to the world?
The choice is yours.
If you'd like help crushing those bottlenecks, getting out of the weeds and staying out, and living a big life crushing big goals, please give me a shout. I can help.
The first step is that complimentary Lifetime Savings Plan. Give it a whirl!
The Four Archetypes of Business Owners (Which one are you?)
Use this to quickly recognize patterns in yourself or your team. The goal is to graduate from crisis and weeds into disciplined, proactive building.
| Archetype | Mindset | Behavior | Core Belief | Tells / Red Flags | Relationship to a CFO | Best Strategy |
|---|---|---|---|---|---|---|
| Crisis Junkie | Pain-focused | Reactive | “I’m at my best when the stakes are highest.” | Boasts about firefighting; always “in the trenches”; last-minute decisions. | Wants a paramedic, not a CFO. Perpetual triage. | Decline or limit to fixed-scope triage with a hard exit. |
| Weed Dweller | Pain-aware | Stuck | “I hate this chaos, but it’s just the way it is.” | Overwhelmed; blames externals; nods at plans, implements none. | High maintenance; low follow-through. | Offer education or a low-stakes diagnostic; avoid full engagement. |
| Aspiring Operator | Growth-curious | Transitional | “There has to be a better way; show me what it looks like.” | Admits gaps; asks specific questions; some discipline present. | Ready to be led; implements with guidance. | Sell a diagnostic/roadmap; guide into system design and cadence. |
| Strategic Builder | Vision-driven | Proactive | “Predictable profits come from predictable systems.” | Thinks in quarters/years; uses scorecards; values discipline. | Ideal partner; high lifetime value; referral-rich. | Offer comprehensive engagement; retainer/advisory with clear KPIs. |
Quick self-check:
- When do you decide? Last minute under pressure, or weeks in advance with a plan?
- What does success look like three years out? Fewer fires, or a designed, scalable system?
- What systems/scorecards exist today? None, partial, or disciplined cadence?
Monetizing Reluctance: A Strategy Brief
Brainstorming Session with ChatGPT — October 2025
1. The Core Insight: Reluctance Rules Everything
Across health, business, government, and technology, the same fundamental pattern repeats: people prefer to minimize, delay, and nibble rather than confront problems head-on. They:
- Put band-aids on deep wounds.
- Play with tools rather than use them fully.
- Avoid heavy lifts like accountability, documentation, and discipline.
This behavior protects the ego in the short term but destroys value over time. Avoidance doesn’t eliminate the work — it simply defers it, adding interest and making the eventual reckoning more painful.
2. Reluctance Everywhere
- Health: Treating cancer symptoms with fiber instead of addressing the disease until surgery becomes unavoidable.
- Government: Debating seven-week continuing resolutions instead of fixing structural budget issues — even as shutdowns stretch just as long.
- Security: Short-term political games put funding for defense, law enforcement, and emergency services at risk.
- Business: Clients use only 5% of powerful systems — dashboards and notes — while ignoring time-tracking, SOPs, and performance management.
- Estate Planning: A trust is created but never funded — an empty box that solves nothing.
- Technology: Companies “toy” with AI tools instead of redesigning workflows to harness their full potential.
The lesson: Reluctance is not the exception. It’s the default human operating system.
3. The Shift: Stop Fighting It — Monetize It
Trying to “educate people out of reluctance” leads to frustration. The strategic move is to profit from human nature instead of battling it.
□ A. Circus-Proof Business Model
- Tier 1 – “The Sideshow”: $199/user/month. Basic features only. If they want to nibble, they pay for the privilege.
- Tier 2 – “The Ringmaster”: $10K–$25K onboarding package. You get paid to implement, train, and clean up what they refuse to do.
- Tier 3 – “The Main Event”: $75K/year base + 15% of improved margin. Full fractional CFO partnership with accountability and outcomes.
Result: Heads you win, tails you win. They either stay surface-level and pay more for less, or they invest in transformation — and pay even more for measurable results.
4. Messaging: From Toys to Transformation
Borrowing from the AI world’s “stop trifling” tone, reposition your offer around seriousness and outcomes:
- Headlines: “Stop Nibbling. Start Building.” | “This isn’t a toy — it’s the backbone of your business.”
- Manifesto: “Most owners poke around at the surface and then wonder why nothing changes. Dashboards don’t build companies — discipline does. The ones who document, train, track, and hold people accountable are the ones who win.”
- Framing: “There are three ways to use a system like this: Toy. Tool. Engine. Only one will change your business.”
This approach reframes you from app builder to architect of transformation — and it creates a natural pull toward the deeper, more profitable engagement.
5. Strategic Takeaway
Reluctance is universal — and predictable. The smartest businesses don’t fight it; they design for it. They:
- Monetize the nibbling.
- Charge for cleanup.
- Profit from outcomes.
- Call out the behavior in their marketing.
In short: If the world insists on being a circus, sell tickets and popcorn.
Copyright © 2025 Kris Freeberg. All rights reserved.
The “Owner Operating Style Quiz,” “Four Archetypes of Business Owners,” and all associated content, scoring methodology, descriptive text, and landing-page language are original works protected under U.S. and international copyright law. No part of this material may be reproduced, distributed, or transmitted in any form or by any means, including photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the copyright owner, except for brief quotations in critical reviews or scholarly works.
