50 Insights

To mark the milestone of 50 issues, I’d like to share 50 insights from this newsletter.

1. Being a generalist is a superpower. When you work across disciplines, you find patterns, principles, and behaviors that are transferable across domains.
2. Friction is a bi-directional force. You can add friction when you want to increase intention. You can remove it when you want to increase speed.
3. What you consume, you assume. Be mindful of the information you take in because it shapes your thinking.
4. Filters create focus. When you have strong philosophies, principles, and playbooks for doing work, you focus your priorities and improve your decision-making in the process.
5. Sustainability is the result of balance. And it’s never quite in perfect equilibrium because you’ll generally have too much—or not enough—of something. It’s in the fluctuation where self-correction occurs.
6. Measuring impact comes from pairing the right leading and lagging metrics. The leading metrics are the inputs; the lagging the outputs. You learn what you need to do more of to increase impact.
7. The best teams think out loud, show their work, and write everything down. These principles underpin every great team I’ve worked with, no matter the environment.
8. To create great work you must create great systems around the work. The best system creates a support structure for the work to emerge organically.
9. Exceptional products spark joy in predictable ways. From how they’re packaged to the personality they embody to the way they are intentionally crafted, beautiful products elicit emotions.
10. Exceptional teams are led by ego-free leaders who give them space with the right level of support. Expectations are clear, focus is protected, and the details of the work are connected to the bigger vision to heighten purpose.
11. Weekly Updates are a useful artifact for keeping a project moving forward. They should clarify the schedule, give updates, and set priorities. They are a snapshot that, when woven together, form an evolutionary log of progress.
12. The act of planning is more important than the plan itself. A Project Plan lets you visualize the lines and edges of the work, allowing you to adapt in real-time as things change (they always do).
13. Product sense is grown through an understanding of the thought process. If you want an engineer to develop a better understanding of design, they need to see Product Reviews where context is freely shared and understood.
14. Models of thinking are the highest form of leverage. Whether it’s design thinking or first principles or systems thinking, you can create transferable knowledge to solve a wide range of problems.
15. Before you commit, experiment. When you have an idea, design an experiment to test your hypothesis, observe the results, and continue iterating. This applies to personal and professional development.
16. A Project Log is a breadcrumb trail to log key milestones in a project’s journey. Use it to track discussion, decisions, and any other data points that may be relevant.
17. Demos of working software are the lifeblood of progress within software development. Showing working software is the best way to validate work and measure progress.
18. Principles are evergreen, foundational truths that form a system of beliefs. They help you make decisions, think critically, and align your actions with your values.
19. Knowledge Alchemy is how you recognize ideas, reflect on them, and repeat them in your work. This process is how ideas transform, grow, and evolve.
20. If you aren’t uncomfortable, you aren’t growing. Life is change and change is growth. And discomfort is where growth lives.
21. Tension guides balance. When two principles pull in different directions, it creates a tension. When managed appropriately, that tension is good because it can create balance.
22. Pulses (reviews + plans) create steady beats that fuel continued growth. Planning in the absence of reviewing is like a weak heartbeat—it doesn’t generate enough energy into the system to work effectively. And a plan without a review risks misdirection.
23. Feedback Loops help conceptualize inputs, outputs, and the process required to take those inputs and convert them into the right outputs. Use them to modify and improve the process.
24. Energy is your most critical resource. Time is a treasure chest and energy is the gold that fills it. Time only matters when it’s paired with energy.
25. Writing is the best method of mental interrogation. Keep a Thought Lab to track and develop your ideas through extensive writing. Language surfaces gaps in knowledge.
26. Rebuild energy by creating space, starting small to build momentum, and finding your ideal flow. Energy fluctuates—optimize for it and adapt.
27. Collaborative Clarity is how you productively discuss and work through problems as a team. You need defined outcomes, space to explore, and a shared mental model of what’s emerging.
28. Cultivate a life of curiosity, experimentation, and iteration, and you’ll unlock new opportunities that naturally fall along a progressive life path. Create a Filedbook to design, track, and test your hypotheses.
29. Sometimes a simple phrasing change can make all the difference. Find a way to reframe the work. Even if you don’t know the solution yet, you can phrase the task as an open-ended question.
30. Surface area is a variable. You can control it up or down, expanding to increase the signal, or contracting to create focus. Used wisely, you can control the surface to shape the outcome.
31. Create better defaults to protect your time, energy, and focus. Say no more, always ask why, and start with small units of work to reduce risk.
32. PM Rounds is a process to assess the context, diagnose the work, and choose a treatment. It’s fluid, adaptable, and dynamic to the work it’s influencing.
33. Reverse Refinement is a development process to build a fast prototype, document the discovered issues, and refine continuously in small iterations. It’s all guesswork until you do the work.
34. Signal Practice forces you to rethink your priorities with a fresh perspective each day. Start with a blank slate, think deeply, and plan intentionally.
35. Artifact Mining is a process to track the works in progress—the early seeds of thoughts, the messy iterations, the evolution of the work. It’s not just about the end product. The evolution matters.
36. Iteration is the connective tissue between speed and quality. Build prototypes, get feedback, and continuously iterate.
37. A healthy team culture is one where healthy behaviors naturally emerge. You spread ideas through memes, build shared mental models, and celebrate the moments where such behaviors happen.
38. A Product Mindset is an Experimental Mindset, driven by a relentless curiosity to continually refine the fidelity of solutions. Once you understand the problem deeply (The Heart), and have a sense for the direction to go (The Compass), you can design low-risk tests to capture feedback iteratively (The Lab).
39. The Project Compass keeps a project on track by understanding where we are right now, where we’re going, and what we’ve learned. It’s about the past, present, and future—all time modalities.
40. Misalignment is a silent killer. Alignment Pillars create the language to find work that’s sustainable, energizing, and meaningful.
41. Leveraged Thinking is the process of slowing down to think clearly so you can act with intention. When you don’t, comfort takes over and drives complacency.
42. Feedback is the fuel of iteration and continuous improvement. It requires diligent management to capture it, prioritize it, and act on it to close the loop.
43. To make better decisions, you need to increase your context window. Like LLMs, higher-quality input creates higher-quality output. Understanding context is how you adjust the conditions necessary to make better decisions.
44. Novelty is a conduit for creativity. New activities, new places, and new approaches unlock new insights. Infuse novelty into your routines to stoke curiosity, creativity, and fresh energy that lights the fire of inspiration.
45. Planning is just a thought experiment. You can choose to keep pretending life is neat and orderly and goes according to a plan. Or you can embrace the chaos of uncertainty, stay mindful in the present moment, and trust your gut to make decisions as you move forward.
46. A Generative Loop generates tangible skills at each step, culminating in the compound output of resonant clarity—that feeling when all the pieces finally connect in your mind, and you uncover the force driving seemingly disparate parts into a coherent whole.
47. You can’t prompt insights. If you rush to the end state, you miss those beautiful moments along the way. All those wondrous “aha moments” are central to the human experience and creative process.
48. Design is meant to be integrative and holistic. While some high-fidelity mockups in Figma may contain intentional thinking, they’re usually visualizing the surface—a high-fidelity visual paired with low-fidelity thinking.
49. While the foundation of great teams is built on trust, the best teams build a unique working rhythm. They work with the garage door open and let ideas flow freely, cultivating an atmosphere of creativity and respect.
50. Nothing is ever done. When you create a plan, it changes when you start. When you share an idea, it evolves. When you build a product, it changes. Life is about the process of change. Because all the best processes catalyze change. They forge new growth.