Three themes dominated my reading:

1. The “Level Up” Mentality. From LitRPG series like Dungeon Crawler Carl and He Who Fights with Monsters to career guides like The Staff Engineer’s Path, I kept gravitating toward stories of progression. The throughline? Life and work are systems that can be mastered and optimized through intentional effort. (If you can’t tell from me reading the entire Dungeon Crawler Carl series in a couple months, I loved these books!)
2. Mastering the Inner Landscape. Between Scattered Minds, The Anxious Generation, Feeling Good, and Taming the Tiger Within, I spent significant time exploring the machinery of the mind. These books offered tools (CBT, mindfulness, and frameworks) for maintaining emotional regulation in a chaotic world.
3. Survival Strategy in High-Stakes Environments. Whether navigating alien-imposed death games or corporate inflection points (Only the Paranoid Survive), my books featured underdogs forced to outsmart larger, often corrupt systems (Empire of Pain). The lesson: strategy isn’t just about winning; it’s about adapting when the old rules no longer apply.

Turns out, I like reading about people who treat life like a game they’re determined to beat, one carefully chosen skill point at a time.

Books Read in 2025

The Holloway Corollary

While the Peter Principle explains one career trap, I’ve observed another pattern just as common that I call the Holloway Corollary:

We rise to the point where our work no longer aligns with what energizes us – leaving us competent, but discontent.

The visual above illustrates this trajectory where competence continues to rise, even as job satisfaction drops off.

I’ve seen talented people become disengaged in roles they’re still capable of excelling in. A few examples:

• Someone who is great at managing teams but loves debugging the hardest problems
• A well-spoken, rockstar presenter who is taken away from working closely with customers
• An affable but introverted manager is asked to spend more time attending and leading meetings
• The maven that cannot work on new challenges

This often comes from being focused outside our strengths and passions. When the effort and reward no longer align, we burn out. Many people can continue competently, but not contentedly.

A Recent Example

A senior engineer I know was promoted to manager and spent months doing calendar Tetris, performance reviews, and paperwork (approvals, status updates). She and her teams were doing well, but she was miserable. Eventually, she stepped back into an IC role and rediscovered her spark. (She has not ruled out going back to management as part of the Engineer/Manager pendulum where senior people alternate between IC and manager, improving themselves and staying fresh along the way.)

Signs You’ve Hit the Corollary

Here are a few signs that you’re competent but discontent:

• You dread Monday mornings, even though you’re performing well
• You’re great at your job but secretly wish you were doing something else
• You find yourself nostalgic for earlier, less senior roles

You may find the Maslach Burnout Inventory helpful in assessing your current situation.

Possible Causes

Our motivations shift over time. What once excited us can slowly become exhausting. A job that once lit us up may eventually wear us down – even if nothing external changes. That change can happen suddenly but often happens gradually. For example, the adventurous 20-something who settles down in the 30s and focuses more on family or the employee-turned-founder who grinds with strong purpose. When your job no longer fits your current motivations, you naturally lose motivation.

Equally important are external factors such as company culture and economic conditions. Many people who purposely joined a small company will dislike the company after private equity takeover. Similarly, a serial job-hopper may stay put for a while when the market tanks and job openings are rare.

Career ladders often start with quick progress but eventually plateau, especially in companies with few senior roles or rigid title structures.

Structural or unconscious bias can limit advancement, leaving capable people stuck in misaligned roles.

Finally, I have seen some people unhappily grinding it, locked in due to golden handcuffs where their current compensation is appealing enough to justify staying longer.

Possible Solutions

How can you avoid falling victim to the Peter Principle and Holloway Corollary? Here are several ideas that you should apply routinely to keep up with change.

• Consistently ask for feedback
• Introspect to understand what you like and dislike – your ikigai or reason for working
• Craft your perfect job by identifying tasks you enjoy and seeking opportunities to incorporate them into your role
• Seek experiences that best fit your desires and actively negotiate away the experiences that drain you
• Avoid career moves (up, down, or sideways) that do not align with your interests
• Include your contentment into your career calculus – money is not everything

What’s one part of your current role that drains your energy — even if you’re good at it?

Conclusion

Many people may excel in one role and get promoted only to find themselves unable to do the job (Peter Principle) or disinterested in the job (Holloway Corollary). If the idea of competent yet discontent resonates with you, it might be time to take stock of what truly energizes you – before your competence becomes a quiet trap. The best careers aren’t just built on skill — they’re fueled by energy.

I hope you all can find meaningful work.

1. Skeptics who refuse to engage with AI
2. Dabblers who have tested the waters
3. Practitioners who treat AI as a turbocharger that can help with a variety of tasks

The Practitioners are reaping the rewards and will continue to improve.

Anti-AI Sentiments from Software Developers

Not all developers are against AI. In my experience, developers’ anti-AI sentiments stem from three main causes:

• Overhyped
  • GenAI can be inaccurate. AI for coding has been hit or miss with many reporting generated code that does not work. Thousands of researchers and engineers are working to improve AI systems, from reducing costs to eliminating hallucinations to agentic systems that work through a process locally before sharing the results. These advances are improving accuracy, and benchmarks reflect those improvements.
  • Developers are more likely to understand AI than the average person and they are logical, so many developers find the marketing incorrect or unrealistic.
  • AI is a powerful tool, but it cannot do everything.
• Threatening
  • Job security. We all want to believe that we are immune to the threat of AI, but AI reduces software job security. On the other hand, AI is also creating new jobs; for example, AI researchers and prompt engineers plus many more coming.
  • Takes the art out of software. Many developers enjoy the creative aspects of developing systems and AI assistants threaten to do all the fun stuff.
  • Could erode the industry, overall quality, and community
  • Advanced AI/ML can be intimidating. While devs may know the basics of AI, there is a huge gap between understanding the basics and training the advanced models.
• Dubious ethics and unease about usage
  • People naturally fear what they do not know. Large Language Models (LLMs) and generative AI (GenAI) are new to the masses and it will take time for knowledge to spread.
  • AI is potentially biased, insecure, and dangerous. Many feel that AI is currently operating in an unchecked and unregulated way, which makes them uneasy.
  • Many feel equality is low and AI will further advantage the wealthy, rather than be a force for good.
  • Will AI regress coding knowledge? For example, could an overreliance on AI atrophy our collective problem solving abilities and harm human self-sufficience?

Get on the AI Bus

I encourage everyone to get on the AI bus and go further faster.

By not exploring and adopting the technology, you risk losing out on many benefits. For me the top benefits are

• Increased productivity: AI can help with virtually everything, saving you time when applied correctly.
• Reduced tedium: AI assistants can handle boring tasks without complaint.
• Improved code quality: all new code can be reviewed quickly by the equivalent of a very learned junior developer, which will increase the use of design principles and adherence to best practices.
• Enhanced problem solving: we now have access to an extremely well-read, patient oracle that is willing to talk about anything.

Applying AI to Your Daily Life

AI can complete a wide range of tasks right now. Below is a short list of concrete ideas with very basic prompts.

• Review and critique code
  • Get a mid-level code review without bugging your peers – critique the following code
  • Find bugs, security holes, and performance issues – help identify bugs in this method
• Generate basic scaffolding. Note: It will likely need tweaking; however, this is already the case with adapting code from books and blogs
  • Code – scaffold a responsive blog home page
  • Tests – create a test suite for this class
• Write commit messages and pull request descriptions – summarize these changes as a commit message
• Write documentation – document this method
• Generate diagrams; for example, flow diagrams or entity relationship diagrams (ERD) – generate an entity relationship diagram for this relational schema
• Create icons and images – create an image of a van with AI badging
• Act as a sounding board for help with design, coding, debugging, scheduling, etc – help me brainstorm architecture ideas for a horizontally scalable authentication service backed by a relational database
• Get personalized learning suggestions – I took data structures and algorithms in college years ago, what are more advanced topics to learn?
• Convert to a language you know – rewrite the following Java code into idiomatic Python

Overall, AI is a powerful tool to expand your knowledge and multiply your productivity. It is not a replacement for critical thinking. As with previous tools like books, blogs, and Q&A sites, you should understand the examples rather than blindly copy/pasting or parrotting something you do not understand.

Here’s to the future! 😎

This year I read 20 books with a non-fiction skew. I worked hard to improve myself mentally and physically. Beyond software leadership, meditationm and psychology, I dipped into sales.

My most recommended book of 2024 is Outlive by Peter Attia, which summarizes longevity research in an accessible, actionable way. I really enjoy Dr. Attia’s framework, and have tried to strengthen my existing good habits and adopt new habits after reading this book. Here’s to a long, meaningful life in 2025 and beyond!

“May you be free of suffering and the root of suffering.”

In trying to improve myself and help others I developed a framework to gauge and improve how I assist others: the Helpfulness Ladder. It’s a simple ladder to climb, from unhelpful to exceptional.

Exploring the Helpfulness Ladder with an example

Work is a team sport, and we are all more productive with help. “I’m too busy to be more helpful!” you say. I know we are all busy! You can climb the ladder in seconds and save future self time. Last week, I wasted an hour searching for a document a co-worker found and shared in seconds.

Imagine someone asks, “How much did we spend on Marketing in May 2024?”

The levels of helpfulness in responding to this question can vary widely depending on the depth, quality, and appropriateness of the response. Here’s the Helpfulness Ladder for this scenario, ranging from harmful and unhelpful to extremely helpful:

Level 0: Harmful (Actively Unhelpful)

• Response: Providing bad information or blocking access to the needed information.
• Example: “Read through the rules and regulations for marketing spend,” or confidently providing a number that is wildly off.

Level 1: Unhelpful (No Meaningful Help)

• Response: Ignoring the question or providing a dismissive answer.
• Example: “You’ll have to figure it out,” or simply not responding.

Level 2: Minimally Helpful (Basic Acknowledgment)

• Response: Acknowledges the question but offers little or no meaningful assistance.
• Example: “I’m not sure,” without any attempt to assist further.

Level 3: Somewhat Helpful (Surface-Level Help)

• Response: Provides a general or vague answer that might help but lacks detail or specificity.
• Example: “I think the file is on the shared drive, but I don’t know where exactly.”

Level 4: Moderately Helpful (Adequate but Generic Help)

• Response: Offers a straightforward answer that directly addresses the question but doesn’t go beyond what’s asked.
• Example: “The file you’re looking for is in the Marketing folder on the shared drive.”

Level 5: Highly Helpful (Thoughtful and Detailed Help)

• Response: Provides a thorough and accurate answer tailored to the question, ensuring clarity.
• Example: “The file is in the Marketing folder on the shared drive, under the 2024 Q2 Reports subfolder.”

Level 6: Extremely Helpful (Proactive Assistance)

• Response: Provides a detailed answer and offers additional proactive assistance to ensure the issue is fully resolved.
• Example: “The file is in the Marketing folder under the 2024 Q2 Reports subfolder. I’ve emailed you the direct link just in case.”

Level 7: Exceptionally Helpful (Empowering and Anticipatory Help)

• Response: Provides a detailed answer, additional assistance, and anticipates future needs or related issues.
• Example: “The file is in the Marketing folder under the 2024 Q2 Reports subfolder. I’ve emailed you the link. I also included a guide to accessing other quarterly reports, in case you need them for future projects. Let me know if you’d like to go over the data together!”

Essentially, a high quality response will generally have more of these elements:

• The answer
• Context around how you found the answer
• A link to necessary or related resources
• An offer for additional assistance

Responses can be weakened due to the following issues:

• Lack of clarity. Avoid formatting issues, excessive wordiness, or illogical ideas that obscure your message.
• Incorrect or inadequate information. Provide proper context, consider adding screenshots, avoid jargon and expand acronyms (e.g., “definition of ready (DoR)”).
• Unhelpful or unprofessional tone. Remember that you are interacting with a person trying to do their job. Avoid being dismissive, sarcastic, or rude.

This concept is widely applicable. For example, consider a teammate asking, “How do I debug this code?” A Minimally Helpful “Google it” pales next to a Highly Helpful “Check the logs – here’s a trick I used last week.” Research backs this: studies on workplace empathy (e.g., from Harvard Business Review) show proactive help builds stronger teams.

How to Deal with Less Helpful Responses

Navigating interactions with less helpful colleagues can be challenging, but it’s essential for maintaining productivity and a positive work environment. Here’s a guide to addressing various levels of unhelpfulness:

1. Dealing with Harmful Responses (Level 0):
   • Document Everything: Keep a detailed record of the harmful responses, including dates, times, specific statements, and any resulting consequences.
   • Escalate to Management: If the behavior is intentional or repeated, consider discussing it with their manager to find a constructive solution. Focus on factual evidence and the impact on your work.
   • Seek Mediation: If possible, consider involving a neutral third party to mediate the situation.
   • Use GenAI: Tools like ChatGPT can help draft messages, so consider working with GenAI to craft a response; for example by prompting, “a co-worker has been unhelpful and harmful in response to my simple asks. help me write a message to their manager communicating the situation.” Be sure to edit the output to ensure it is factual and objective.
2. Addressing Unhelpful or Minimally Helpful Responses (Levels 1 and 2):
   • Clarify Your Needs: Rephrase your question, providing more context and explaining why the information is essential. For example, instead of “Where’s the file?”, try “I need the marketing budget file from May 2024 to finalize this report. Do you know where it’s located, or who might?”
   • Seek Alternative Sources: If possible, find the information from another source or colleague.
   • Set Clear Expectations: If the behavior is recurring, gently communicate your expectations for responsiveness and helpfulness. For example, “I understand you’re busy, but timely responses are crucial for project deadlines.”
3. Navigating Somewhat Helpful or Vague Responses (Level 3):
   • Ask Specific Follow-Up Questions: Probe for more details to clarify the vague response. For example, “You mentioned the file is on the shared drive. Could you give me a more specific folder name or path?”
   • Offer to Collaborate: Suggest working together to find the information. For example, “Would you be available for a quick screen-share so we can locate the file together?”
   • Document and Request Sources: If they give you an answer, but not a source, you are well within your rights to say, “Thank you! Where did you find that information – could you share a link, please?”
4. Encouraging More Helpful Responses (Levels 4 and 5):
   • Express Appreciation and Reinforce Positive Behavior: When someone provides a helpful response, acknowledge their effort and highlight the value of their assistance.
   • Ask a Small Favor: If someone is generally unhelpful, try asking for a small favor or additional help to win them over, a method sometimes referred to as the Ben Franklin Effect. For example, “Thank you! I’ll work with that. Do you mind if I ask follow-ups as needed?” or “I really appreciate your help with this. Could you quickly look over this other related item for me? Your input would be very valuable.”
   • Inquire About Their Process: If they provide the answer without explaining the process, ask, “Thank you! Can you please share how you figured that out so I know for next time?” This encourages knowledge-sharing and empowers you to learn.

Benefits of Being Helpful

Being helpful is good for everyone and costs you little. There are many benefits that enhance individual performance, team dynamics, and organizational success. Here are the top advantages, grounded in practical outcomes and supported by general insights from workplace studies:

1. Foster Stronger Relationships and Trust Helping colleagues builds trust and fosters positive relationships. By being reliable and approachable, you create a network of mutual support that encourages collaboration and teamwork.
2. Boost Your Reputation and Influence Consistently being helpful establishes you as a go-to person, increasing your professional credibility and influence. This reputation can lead to greater recognition, promotions, and leadership opportunities.
3. Elevate Team Performance A helpful attitude lifts the entire team, reducing friction and improving efficiency. By sharing resources, clarifying goals, and assisting with deadlines, you contribute to higher team productivity and innovation.
4. Drive Personal Growth and Skill Development Helping others sharpens your problem-solving, communication, and teaching skills. By explaining processes and solving problems, you deepen your understanding and expertise.
5. Increase Job Satisfaction Contributing to others’ success triggers positive emotions, reducing stress and boosting morale. By being helpful, you feel more connected, valued, and fulfilled in your work. Gallup’s workplace engagement data ties prosocial behavior to higher employee happiness and retention.

In summary, being helpful with support requests has a ripple effect of benefits. By adopting this mindset, you:

• Build stronger relationships and trust
• Enhance your reputation and influence
• Elevate team performance
• Drive personal growth and skill development
• Increase job satisfaction

When to Be Less Helpful

Remember, being helpful is not about sacrificing your own well-being, but about finding a balance that benefits everyone involved. It is fair to set boundaries on your time, to prioritize your own work, and protect your sanity. There will be times when you need to focus on people who reciprocate or triage the requests based on those most in need of assistance.

Conclusion

I hope that the Helpfulness Ladder can promote intentionality, empathy, and effectiveness in interactions. By visualizing helpfulness as a progression from minimal to exceptional support, individuals can grow personally and professionally, foster a more collaborative environment, and get more done.

Next time you’re asked for support, pause. Could you add context or a resource to climb a rung? Try it! Ask a clarifying question like, “What do you need this for?” to tailor your response. Small steps up the ladder make a big difference for your team and organization. Being as helpful as reasonably possible is a low-cost, high-reward habit that pays off for everyone involved.

I was delighted by Ross Gay’s The Book of Delights as well as Brandon Sanderson’s Surprise! novels (my favorite was The Sunlit Man for its glimpse into the Cosmere).

I really enjoyed the Elon Musk biography by Walter Isaacson because it provided more context around one of the world’s most news-worthy characters.

My son and I read a few young adult books together, which marks a new chapter where we can enjoy the same things – I love it!

Since having a child, I have enjoyed the thought exercise of deciding what advice I would capture and pass on, and I think Kevin Kelly’s collection of advice is a great start.

Dr. Becky’s viral parenting book, Good Inside, was one of my favorite non-fiction books and one that I would recommend to everyone. It helped me on my quest to get better every day.

2023 had its share of highs and lows. I am grateful for so many things, including an endless supply of fantastic reads. Here’s to a wonderful 2024!

I read some great fiction this year! I caught up on a couple Brandon Sanderson series (Mistborn: Wax and Wayne and Skyward) and read The Legends of the First Empire Series by Michael J Sullivan.

On the non-fiction front I appreciated Will Larson’s Staff Engineer book for capturing a number of important topics for technical leaders who don’t go into management and Lara Hogan’s Resilient Management for capturing the basics for those on the management track. The Sum of Us and Just Mercy helped me understand the past and present lived experiences of Black Americans, while The Culture Map helped me understand more about people from across the world. Atlas of the Heart helped me improve my emotional intelligence. Become What You Are by Alan Watts and Awareness by Anthony De Mello bridged multiple spiritualities in a way that helped me feel more connected to my fellow humans.

I hope others can enjoy their reading as much as I did in 2022.

Rise by Patty Azzarello was the freshest leadership book I’ve read recently, with many helpful, applicable tips. I read several leadership fables by Patrick Lencioni, including Death by Meeting, The Motive, and The Three Signs of a Miserable Job; those books were light, quick, and good, and they led me to Overcoming the Five Dysfunctions of a Team, which I drew upon to help my teams gel more during COVID. Jocko Willink’s Leadership Strategy and Tactics resonated with me by nicely defining the “extreme ownership” that I feel for my teams and providing strategy and tactics for how to improve myself to improve the team.

For fiction I was introduced to the genre of climate change sci-fi with Neal Stephenson’s Termination Shock and The Ministry for the Future by Kim Stanley Robinson, which I found thought-provoking though generally depressing. I read a few other good fiction books to even things out.

• Thanks for the Feedback by Douglas Stone and Sheila Heen. This is the book that I have recommended the most from my 2020 reads. It is applicable to everyone from individual contributors to managers and parents to children. Some takeaways:
  • giving feedback is hard, so be grateful when you receive it
  • accept feedback without pushing back – just say, “thanks for the feedback” – later, seek to understand the feedback more deeply
  • act on good feedback and disregard bad feedback
• The Manager’s Path by Camille Fournier. One of my favorite management books. The author describes roles from senior developer up through C-levels, so this work has value for every level of technical leader.
• Thinking in Systems by Donella Meadows. Everything is a system, and that includes companies. The people and processes in place make up a system, and people will learn to game that system. To make meaningful change, we have to understand and change those systems. We cannot simply apply the best ideas from a competitor and expect it to work because their system is different than ours.
• Brandon Sanderson’s epic fantasy series, Stormlight Archive continued with Rhythm of War, which was great. Who doesn’t love a 1,200-page book?! ☺

• Homo Deus by Yuval Noah Harari. A wonderful mixture of history, psychology, and technology. I was engaged throughout.

• The Power by Naomi Alderman. What if women were more dangerous than men? This book explores the idea, and I found it mind-expanding in a good way. Let’s be excellent to each other.

• The Iron Druid Chronicles by Kevin Hearne. In 2019 I finished the Iron Druid Chronicles, a series that I thoroughly enjoyed.

• Never Split the Difference: Negotiating As If Your Life Depended On It by Chris Voss. My big takeaway is sharing the problem-solving by asking, “how am I supposed to do that?” when negotiating.

• Republic, Lost: How Money Corrupts Congress–and a Plan to Stop It by Lawrence Lessig. This book taught me that ‘Money in politics isn’t the most important problem, but it is the first problem because we cannot tackle the most important problems until we remove money from the equation.’ I found this book to be very important. I genuinely hope that we can reform American politics and reduce the role that money plays.

• High Output Management by Andrew S. Grove. This is a management classic for a reason! There are a number of great concepts in this book. I would recommend it to managers and aspiring technology leaders.