Mentoring

Build Systems for Your Worst Days, Not Your Best

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I’ve had those days. You know the ones: back-to-back meetings, your inbox growing like a fungal bloom in the dark, and just a single, precious hour to get anything meaningful done. Those are the days when your tools, workflows, and systems either rise to meet the challenge—or collapse like a Jenga tower on a fault line.

And that’s exactly why I build systems for my worst days, not my best ones.

Thinking

When You’re Running on Fumes, Systems Matter Most

It’s easy to fall into the trap of designing productivity systems around our ideal selves—the focused, energized version of us who starts the day with a triple espresso and a clear mind. But that version shows up maybe one or two days a week. The other days? We’re juggling distractions, fighting fatigue, and getting peppered with unexpected tasks.

Those are the days that test whether your systems are real or just aspirational scaffolding.

My Systems for the Storm

To survive—and sometimes even thrive—on my worst days, I rely on a suite of systems I’ve built and refined over time:

  • Custom planners for project, task, and resource tracking. These keep my attention on the highest-leverage work, even when my mind wants to wander.

  • Pre-created GPTs and automations that handle repetitive tasks, from research to analysis. On a rough day, this means things still get done while I conserve cognitive bandwidth.

  • Browser scripts that speed up form fills, document parsing, and other friction-heavy tasks.

  • The EDSAM mental model helps me triage and prioritize quickly without falling into reactive mode. (EDSAM = Eliminate, Delegate, Simplify, Automate, Maintain)

  • A weekly review process that previews the chaos ahead and lets me make strategic decisions before I’m in the thick of it.

These aren’t just optimizations—they’re insulation against chaos.

The Real ROI: More Than Just Productivity

The return on these systems goes well beyond output. It’s about stress management, reduced rumination, and the ability to make clear-headed decisions when everything else is fuzzy. I walk into tough weeks with more confidence, not because I expect them to be easy—but because I know my systems will hold.

And here’s something unexpected: these systems have also amplified my impact as a mentor. By teaching others how I think about task design, tooling, and automation, I’m not just giving them tips—I’m offering frameworks they can build around their own worst days.

Shifting the Culture of “Reactive Work”

When I work with teams, I often see systems built for the ideal: smooth days, few interruptions, time to think. But real-world conditions rarely comply. That’s why I try to model and teach the philosophy of resilient systems—ones that don’t break when someone’s sick, a deadline moves up, or a crisis hits.

Through mentoring and content, I help others see that systems aren’t about rigidity—they’re about readiness.

The Guiding Principle

Here’s the rule I live by:

“The systems have to make bad days better, and the worst days minimally productive—otherwise, they need to be optimized or replaced.”

That sentence lives in the back of my mind as I build, test, and adapt everything from automations to mental models. Because I don’t just want to do great work on my best days—I want to still do meaningful work on my worst ones.

And over time, those dividends compound in ways you can’t measure in a daily planner.

Support My Work

Support the creation of high-impact content and research. Sponsorship opportunities are available for specific topics, whitepapers, tools, or advisory insights. Learn more or contribute here: Buy Me A Coffee

 

* AI tools were used as a research assistant for this content, but human moderation and writing are also included. The included images are AI-generated.

Seizing Career Leverage by Building a Body of Public Work

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On the surface, it may seem easier to pursue another certificate, add another line to your resume, or polish a few more LinkedIn keywords. That’s the default advice. But I’ve found that the true differentiator—the thing that has consistently opened the most doors in my career and in the lives of those I mentor—is something less talked about: building a public body of work.

ThinkingPlanning

For me, it didn’t start with a strategic master plan. It was organic. A blog here. A talk there. Over time, though, the pattern became clear. The more consistently I created public work—writings, talks, podcasts, code, experiments—the more serendipity showed up. People would reach out. Ideas would flow. And opportunities would emerge.

Creating in public does something powerful: it makes you discoverable. It turns your ideas into tiny relationship builders scattered across the internet. They work quietly on your behalf—sharing, connecting, and engaging. They let people find you not just for who you say you are, but for what you actually do and think and build. In essence, your work becomes your calling card.

Kevin Kelly wrote about the concept of 100 True Fans, and I think that framework applies here, too. When you create with consistency and intention, your work resonates. People engage. They share. They connect. You become a node in a larger network. Not geographically constrained. Not bound to a title. But influential because of contribution.

Of course, this isn’t easy. If it were, everyone would be doing it.

The resistance is deep and evolutionary. When you make something public—your ideas, your interests, your perspective—you draw attention to yourself. You leave the crowd. And for most of human history, that was dangerous. Our lizard brains still think it is.

But here’s the truth: life happens at the edges. It happens when you step away from the herd and choose to teach, lead, explore, or question. That’s where the value is—not just in terms of career growth, but in living a more interesting life.

The tools to get started are easier than ever. A blog costs nothing but time and focus. A podcast is within reach with a decent mic and an internet connection. A video or short-form tutorial can find thousands of eyes in hours. The barrier isn’t access. It’s courage. And then—discipline.

There won’t be a singular moment where you “make it.” Instead, you’ll find momentum. The blog post you wrote last year still gets read. The talk you gave finds its way to someone’s inbox. The experiment you published helps someone else start their own.

But here’s the trick: create to help. Self-serving content evaporates quickly. But service-oriented content—something that teaches, guides, explores—can live on. Sometimes for years. Sometimes forever.

And perhaps most important: you get to choose what you create. That’s a kind of creative sovereignty many professionals never tap into. It’s a superpower. And like any superpower, it comes with responsibility.

So here’s what I tell my mentees:

Actions speak louder than words. A portfolio is more potent than a certificate on your resume.

Teach courage. Encourage contribution. Show them that real growth—personal, professional, even spiritual—happens at the edges. Not in the safe middle.

Put your work into the world. Let it work for you. And help others as you do. That’s how you build a life and career that’s not just successful, but truly extraordinary.

Support My Work

Support the creation of high-impact content and research. Sponsorship opportunities are available for specific topics, whitepapers, tools, or advisory insights. Learn more or contribute here: Buy Me A Coffee

 

* AI tools were used as a research assistant for this content, but human moderation and writing are also included. The included images are AI-generated.

The Second Half: Building a Legacy of Generational Knowledge

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“Build, establish, and support a legacy of knowledge that not only exceeds my lifetime, but exceeds generations and creates a generational wealth of knowledge.”

That’s the mission I’ve set for the second half of my life. It’s not about ego, and it’s certainly not about permanence in the usual sense. It’s about creating something that can outlast me—not in the form of statues or plaques, but in the ripples of how people think, solve problems, and support each other long after I’m gone.

ChatGPT Image Aug 2 2025 at 04 04 22 PM

Three Pillars of a Legacy

There are three key prongs to how I’m approaching this mission. Each one is interwoven with a sense of service and intention. The first is about altruism—specifically, applying a barbell strategy to how I support systems and organizations. The middle of the bar is the consistent, proven efforts that deliver value today. But at the ends are the moonshots—projects like the psychedelic science work of MAPS or the long-term frameworks for addressing food insecurity and inequality. These aren’t about tactics; they’re about systems-level, knowledge-driven approaches that could evolve over the next 50 to 100 years.

The second pillar is more personal. It’s about documenting how I think. Inspired in part by Charlie Munger, I’ve come to realize that just handing out solutions isn’t enough. If you want to make lasting impact, you have to teach people how to think. So I’ve been unpacking the models I use—deconstruction, inversion, compounding, Pareto analysis, the entourage effect—and showing how those can be applied across cybersecurity, personal health, and even everyday life. This is less about genius and more about discipline: the practice of solving hard problems with reusable, teachable tools.

The third leg of the stool is mentoring. I don’t have children, but I see the act of mentorship as my version of parenting. I’ve watched people I’ve mentored go on to become rock stars in their own right—building lives and careers they once thought were out of reach. What I offer them isn’t just advice. It’s a commitment to help them design lives they want to live, through systems thinking, life hacking, and relentless self-experimentation.

Confidence and Competence

One of the core ideas I try to pass along—both to myself and to my mentees—is the importance of aligning your circle of confidence with your circle of competence. Let those drift apart, and you’re just breeding hubris. But keep them close, and you cultivate integrity, humility, and effective action. That principle is baked into everything I do now. It’s part of how I live. It’s a boundary check I run daily.

The Long Game

I don’t think legacy is something you “leave behind.” I think it’s something you put into motion and let others carry forward. This isn’t about a monument. It’s about momentum. And if I can contribute even a small part to a future where people think better, solve bigger, and give more—then that’s a legacy I can live with.

 

 

* AI tools were used as a research assistant for this content, but human moderation and writing are also included. The included images are AI-generated.

The Huston Approach to Knowledge Management: A System for the Curious Mind

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I’ve always believed that managing knowledge is about more than just collecting information—it’s about refining, synthesizing, and applying it. In my decades of work in cybersecurity, business, and technology, I’ve had to develop an approach that balances deep research with practical application, while ensuring that I stay ahead of emerging trends without drowning in information overload.

KnowledgeMgmt

This post walks through my knowledge management approach, the tools I use, and how I leverage AI, structured learning, and rapid skill acquisition to keep my mind sharp and my work effective.

Deep Dive Research: Building a Foundation of Expertise

When I need to do a deep dive into a new topic—whether it’s a cutting-edge security vulnerability, an emerging AI model, or a shift in the digital threat landscape—I use a carefully curated set of tools:

  • AI-Powered Research: ChatGPT, Perplexity, Claude, Gemini, LMNotebook, LMStudio, Apple Summarization
  • Content Digestion Tools: Kindle books, Podcasts, Readwise, YouTube Transcription Analysis, Evernote

The goal isn’t just to consume information but to synthesize it—connecting the dots across different sources, identifying patterns, and refining key takeaways for practical use.

Trickle Learning & Maintenance: Staying Current Without Overload

A key challenge in knowledge management is not just learning new things but keeping up with ongoing developments. That’s where trickle learning comes in—a lightweight, recurring approach to absorbing new insights over time.

  • News Aggregation & Summarization: Readwise, Newsletters, RSS Feeds, YouTube, Podcasts
  • AI-Powered Curation: ChatGPT Recurring Tasks, Bayesian Analysis GPT
  • Social Learning: Twitter streams, Slack channels, AI-assisted text analysis

Micro-Learning: The Art of Absorbing Information in Bite-Sized Chunks

Sometimes, deep research isn’t necessary. Instead, I rely on micro-learning techniques to absorb concepts quickly and stay versatile.

  • 12Min, Uptime, Heroic, Medium, Reddit
  • Evernote as a digital memory vault
  • AI-assisted text extraction and summarization

Rapid Skills Acquisition: Learning What Matters, Fast

There are times when I need to master a new skill rapidly—whether it’s understanding a new technology, a programming language, or an industry shift. For this, I combine:

  • Batch Processing of Content: AI analysis of YouTube transcripts and articles
  • AI-Driven Learning Tools: ChatGPT, Perplexity, Claude, Gemini, LMNotebook
  • Evernote for long-term storage and retrieval

Final Thoughts: Why Knowledge Management Matters

The world is overflowing with information, and most people struggle to make sense of it. My knowledge management system is designed to cut through the noise, synthesize insights, and turn knowledge into action.

By combining deep research, trickle learning, micro-learning, and rapid skill acquisition, I ensure that I stay ahead of the curve—without burning out.

This system isn’t just about collecting knowledge—it’s about using it strategically. And in a world where knowledge is power, having a structured approach to learning is one of the greatest competitive advantages you can build.

You can download a mindmap of my process here: https://media.microsolved.com/Brent’s%20Knowledge%20Management%20Updated%20031625.pdf

What about you? How do you manage your learning and knowledge? Let me know—I’m always refining my system.

 

* AI tools were used as a research assistant for this content.

 

 

The Entrepreneur’s Guide to Overcoming Fear of Failure

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Fear of failure is a common barrier that holds back many aspiring entrepreneurs. It’s a natural response to the uncertainty and risks involved in starting and running a business. However, overcoming this fear is crucial for success. Here are some insightful strategies and real-world examples to help you embrace risk and failure on your entrepreneurial journey.

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 1. Understand That Failure is a Learning Opportunity

– Embrace a Growth Mindset: Entrepreneurs need to see failure not as a dead-end but as a stepping stone to success. Adopting a growth mindset helps you learn from mistakes and continuously improve.
– Example: Thomas Edison famously failed thousands of times before inventing the light bulb. He saw each failure as a lesson, saying, “I have not failed. I’ve just found 10,000 ways that won’t work.”

 2. Set Realistic Goals and Manage Expectations

– Break Down Big Goals: Setting smaller, achievable goals can reduce the fear of failure. It makes the larger objective seem more manageable and provides a sense of accomplishment along the way.
– Example: When launching a new product, start with a pilot project or a small market test. This approach allows you to gather feedback, make adjustments, and reduce the financial risk.

 3. Build a Support Network

– Seek Mentorship and Advice: Surround yourself with experienced entrepreneurs who can provide guidance and share their experiences of overcoming failure.
– Example: Sara Blakely, the founder of Spanx, credits much of her success to the advice and support she received from mentors. Their encouragement helped her persevere through the challenges of building her business.

 4. Prepare for Failure

– Have a Contingency Plan: Being prepared for potential setbacks can alleviate the fear of failure. A well-thought-out contingency plan can help you navigate difficulties with confidence.
– Example: Dropbox initially faced significant challenges with its business model and competition. By having backup strategies and being flexible, they were able to pivot and refine their product, eventually achieving massive success.

 5. Embrace Calculated Risks

– Evaluate Risks and Rewards: It’s essential to take risks, but they should be calculated. Assess the potential impact and benefits before making a decision.
– Example: Jeff Bezos took a calculated risk when he left his secure job to start Amazon. He weighed the potential rewards against the risks, deciding that the opportunity was worth pursuing despite the uncertainty.

 6. Focus on What You Can Control

– Control Your Effort and Attitude: While you can’t control every outcome, you can control your response and the effort you put in. This focus can reduce anxiety and increase resilience.
– Example: Elon Musk has faced numerous failures with SpaceX and Tesla. His relentless work ethic and positive attitude have helped him persist and ultimately succeed, despite setbacks. (Of course, he might also be insane…)

 7. Learn from Others’ Mistakes

– Study Successful Entrepreneurs: Understanding how others have navigated failure can provide valuable insights and strategies.
– Example: Richard Branson, founder of the Virgin Group, openly shares his business failures. By learning from his experiences, aspiring entrepreneurs can avoid similar pitfalls and adopt effective strategies.

 8. Reframe Failure as Feedback

– View Failure as Constructive Criticism: Instead of seeing failure as a negative outcome, treat it as feedback on what needs improvement.
– Example: The creators of Angry Birds, Rovio Entertainment, developed 51 unsuccessful games before achieving global success. Each failure provided valuable feedback that led to the creation of their hit game.

 9. Develop Resilience and Perseverance

– Cultivate a Resilient Mindset: Building mental toughness helps you bounce back from setbacks and stay committed to your goals.
– Example: J.K. Rowling faced numerous rejections before finding a publisher for Harry Potter. Her resilience and perseverance paid off, leading to one of the most successful book series in history. (Note: I am not a fan of Ms. Rowling, but she is a good example here…)

 10. Celebrate Small Wins

– Acknowledge Progress: Recognizing and celebrating small achievements can boost your confidence and motivation.
– Example: When launching a startup, celebrate milestones such as securing initial funding, launching a website, or gaining the first 100 customers. These small wins can keep you motivated through challenging times.

 Conclusion

Overcoming the fear of failure is essential for entrepreneurial success. By understanding that failure is part of the journey, setting realistic goals, building a support network, and embracing calculated risks, you can navigate the uncertainties of entrepreneurship with confidence. Learn from others, reframe failure as feedback, and develop resilience to keep moving forward. Remember, every successful entrepreneur has faced failure—what sets them apart is their ability to learn, adapt, and persist.

 

* AI tools were used as a research assistant for this content.

 

How to Use Mental Models to Save Cognitive Energy and Attention in Day-to-Day Life

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In the hustle and bustle of modern existence, our minds are constantly inundated with a deluge of data. From sunrise to sunset, we’re faced with a barrage of choices, both monumental and minuscule, that sap our mental stamina. But fear not, for there is a solution: mental models. These nifty cognitive tools help streamline our thought processes, enabling us to tackle life’s daily obstacles with greater ease and efficiency. By harnessing the might of mental models, we can conserve our precious brainpower for the things that truly matter.

MentalModels

Unveiling the Enigma: What Exactly Are Mental Models?

Picture mental models as the scaffolding that supports our understanding and interpretation of the world around us. They take complex concepts and boil them down into a structured approach for tackling problems and making decisions. In essence, they’re like cognitive shortcuts that lighten the mental load required to process information. Mental models span a wide range of fields, from economics and psychology to physics and philosophy. When wielded effectively, they can dramatically enhance our decision-making and problem-solving prowess[1][2].

 Unleashing the Potential: Mental Models in Action

 1. The Pareto Principle: Doing More with Less

The Pareto Principle, also known as the 80/20 rule, suggests that 80% of results stem from a mere 20% of efforts. This principle can be a real game-changer when it comes to prioritizing tasks and zeroing in on what truly matters.

Real-World Application: Picture yourself as a project manager with a daunting to-do list of 20 tasks. Rather than trying to juggle everything at once, zero in on the top four tasks that will have the most profound impact on the project’s success. By focusing your energy on these critical tasks, you can achieve more substantial results with less effort[1].

 2. Inversion: Flipping the Script

Inversion involves approaching problems from the opposite angle to pinpoint potential pitfalls and solutions. By considering what you want to avoid, you can unearth strategies to achieve your goals more effectively.

Real-World Application: Let’s say you’re orchestrating a major event. Instead of solely focusing on what needs to go right, ponder what could go wrong. By identifying potential snags, such as equipment malfunctions or scheduling snafus, you can take proactive steps to mitigate these risks and ensure a smoother event[1].

 3. First Principles Thinking: Breaking It Down

First principles thinking, a favorite of Elon Musk, involves deconstructing complex problems into their most basic elements. By grasping the core components, you can devise innovative solutions that aren’t shackled by conventional thinking.

Real-World Application: Imagine you’re trying to optimize your daily commute. Instead of accepting the usual traffic and route options, break down the problem: What’s the fundamental goal? To reduce travel time and stress. From there, you might explore alternative transportation methods, such as biking or carpooling, or even rearranging your work schedule to avoid peak traffic times[1].

 4. The Eisenhower Matrix: Mastering Time Management

The Eisenhower Matrix is a time management tool that categorizes tasks based on their urgency and importance. By sorting tasks into four quadrants—urgent and important, important but not urgent, urgent but not important, and neither urgent nor important—you can prioritize more effectively.

Real-World Application: Your email inbox is overflowing, and you’re drowning in messages. Use the Eisenhower Matrix to sort through your emails. Tackle urgent and important emails first, such as those from your boss or key clients. Important but not urgent emails can be scheduled for later, while urgent but not important ones (like promotional offers) can be quickly handled or delegated. Lastly, delete or archive those that are neither urgent nor important[1].

 5. Confirmation Bias: Challenging Your Assumptions

Awareness of confirmation bias—the tendency to favor information that confirms our preexisting beliefs—can help us make more objective decisions. By actively seeking out diverse perspectives and challenging our assumptions, we can avoid narrow-minded thinking.

Real-World Application: You’re researching a new investment opportunity and already have a positive opinion about it. To counter confirmation bias, deliberately seek out critical reviews and analyses. By evaluating both positive and negative viewpoints, you can make a more informed decision and reduce the risk of overlooking potential downsides[1].

 Putting Mental Models into Practice: Tips and Tricks

 1. Create a Mental Models Toolbox

Assemble a personal collection of mental models that resonate with you. This could be a digital document, a notebook, or even a series of flashcards. Regularly review and update your toolbox to keep these models fresh in your mind[1].

 2. Start Small and Build Momentum

Begin by applying mental models to everyday decisions. For instance, use the Pareto Principle to prioritize your daily tasks or the Eisenhower Matrix to manage your time. With practice, these models will become second nature[1].

 3. Reflect, Refine, Repeat

After applying a mental model, take a moment to reflect on its effectiveness. Did it help simplify the decision-making process? What could you improve next time? Iterative reflection will help you fine-tune your use of mental models and amplify their impact[1].

 4. Learn from the Best

Study how successful individuals and organizations use mental models. Books like “Poor Charlie’s Almanack” by Charlie Munger and “Thinking, Fast and Slow” by Daniel Kahneman offer valuable insights into the practical application of mental models[1][2].

 5. Never Stop Exploring

Keep exploring new mental models and expanding your cognitive toolkit. The more models you have at your disposal, the better equipped you’ll be to handle a wide range of situations[1][2].

 The Bottom Line

Mental models are indispensable allies in our quest to conserve brainpower and navigate the complexities of daily life. By integrating these cognitive tools into our routines, we can make more informed decisions, solve problems more efficiently, and ultimately free up mental space for what truly matters. Whether you’re prioritizing tasks, managing time, or challenging your assumptions, mental models can help you streamline your thinking and unleash your full potential[1][2]. So, start building your mental models toolbox today and watch as your cognitive load lightens and your decision-making sharpens.

Remember, the goal isn’t to eliminate all cognitive effort but to use it more strategically. By leveraging mental models, you can focus your brainpower where it counts, leading to a more productive, balanced, and fulfilling life[1][2].

Citations:
[1] https://fronterabrands.com/mental-model-examples-and-their-explanations/
[2] https://nesslabs.com/mental-models
[3] https://commoncog.com/putting-mental-models-to-practice-part-5-skill-extraction/
[4] https://durmonski.com/self-improvement/how-to-use-mental-models/
[5] https://jamesclear.com/mental-models
[6] https://blog.hubspot.com/marketing/mental-models
[7] https://fs.blog/mental-models/
[8] https://jamesclear.com/feynman-mental-models
[9] http://cogsci.uwaterloo.ca/Articles/Thagard.brains-models.2010.pdf
[10] https://betterhumans.pub/4-lesser-known-mental-models-that-save-me-30-hours-every-week-efc60f88ec7a?gi=e3c8dbd3d48c
[11] https://www.julian.com/blog/mental-model-examples
[12] https://www.youtube.com/watch?v=hkL7S9cQLQM
[13] https://www.coleschafer.com/blog/ernest-hemingway-writing-style
[14] https://www.okayokapi.com/blog-post/why-your-writing-style-isnt-wrong-or-bad
[15] https://www.turnerstories.com/blog/2019/3/10/how-to-find-your-writing-style
[16] https://carnivas.com/writing-style-culture-7740ad03d7a6?gi=e15f15841156
[17] https://www.reddit.com/r/coolguides/comments/1bgdmp9/a_cool_guide_cheatsheet_to_mental_models_with/
[18] https://writersblockpartyblog.com/2018/04/05/finding-your-writing-style/
[19] https://www.slideshare.net/slideshow/reflection-sample-essay-reflection-essay-samples-template-business/266204999
[20] https://www.slideshare.net/slideshow/example-of-critique-paper-introduction-how-to-write/265714891

 

* AI tools were used as a research assistant for this content.