I've been spending a good bit of time in the Product Manager interview cycle lately, and one recurring interview format that keeps coming back is the "Product Sense" interview. These interviews are typically framed around a prompt like "How would you design X" or "How would you improve X," and aim to dig into your ability to think through an ambiguous problem in a structured way, while communicating clearly throughout.

It can be easy to spin your wheels or get stuck; I've experienced it plenty of times myself. The one thing (aside from practice, of course) that helped me quite a bit was having a plan of attack beforehand. The "plan of attack" that's worked for me is here, in the form of a template, tips, and resources. I've found that if you have a default structure and adapt it to your needs well, that's half the battle. Once you win that, all you have to do is execute, and enjoy the fun part: creatively solving a problem with someone else.

1. Clarifying Questions

Anything unclear off the rip? e.g. “Can you further define “improve” or “engagement” or what platform we’re talking about? Or is this more open-ended? I’m assuming I’m a PM at X? Is that cool?”

2. Structure

Don’t just slap on frameworks. Think about what makes sense given the framing of the prompt. e.g. Do you already know your pain point or target persona? Pick and choose from the following and adapt it to the discussion:

• ⭐️ Motivation: Why does this matter?
• ⭐️ Users: Who and what use cases should we build for?
• ⭐️ Problem: What pain points do the target segment run into?
• ⭐️ Solutions: How should we address the identified pain point?
• ⭐️ Design: What should the prioritized approach look like in user-land?
• Risk Mitigation: What are potential risks or open questions?
• Evaluation: How would you validate or test that this worked or didn’t?

3. Motivation

• Impact for Users: What is the company’s mission and what does it mean for users? Why should they care that the product exists or is improved upon
• Competition + Trends: What competitors exist out there? Are there any trends occurring in the space that are relevant?
• Strengths to Leverage: Does the company have existing building blocks, market share, or tools that are relevant to the prompt?
• Strategic + Business Goals: How does this fit into the company’s goals? Increased market share? Activation? Retention? Revenue?

4. User Segmentation

Start thinking through broad segments based on frequency + use cases, and then segment further until you have a useful, mutually exclusive, oddly specific cut. Then prioritize one based on audience size / frequency of use / alignment with company strategy. More concretely this means:

1. Broad Segments: It's easiest to start with frequency of use + different use cases if they come to mind here.
2. Specific Segments: Hone in on each until you have a oddly specific cut of a few different personas.
3. Prioritization: Assess each on 1) Audience Size 2) Frequency and 3) Alignment with Strategic Goals. Pick one to focus on and explain your reasoning out loud.

5. Problem Identification

Once you have a target segment, it’s time to dig into pain points. Once again it’s simplest to start broad and then get really specific afterwards. Map out the user journey, then identify where friction occurs, and connect it to a hypothesis for why the problem exists. Laid out this looks like:

1. User Journey: Map out a quick list or flow of steps of how the target persona interacts with the product or experience.
2. Specific Pain Points: Hone in on parts of the flow with friction and pick a few pain points to connect to human emotion and pitch to the interviewer. The more specific these are, the more unique your solutions will be later on!
3. Prioritization: Don’t pick a pain point to focus on based on vibes. Assess each based on 1) Frequency and 2) Severity, taking into account existing workarounds if they exist.

6. Solution

Before you dive in to solutioning, it’s good to restate your hypothesis based on prior steps to make sure you’re anchored on that. Once you’re in the right headspace, start generating some ideas:

1. Generate Solutions: Get creative here! Generate a few divergent, interesting approaches to solving the chosen problem.
2. Prioritization: Assess each proposed solution based on 1) Impact and 2) Effort. Explain why you would focus on one, potentially weaving in strategic implications where it makes sense.

7. Design

Describe the overall shape of the chosen approach and map it back to the hypothesis you stated. Then dig into details. Get visual with it, a few boxes with words in them goes pretty far relevant to just talking it out.

1. Overall Shape: What does the overall product experience look like for users and how does it map to the hypothesis?
2. User Flow: If there’s time, get into more details around what exactly the user flow will be. Open up Figma or another design tool and draw some boxes to align on the solution. Summarize once more and typically, that’s a wrap!

Some Tips

With the above in mind, here are some more tips that worked for me:

• Share your screen. Working off a shared doc is easiest to align on.
• Don't blindly apply templates. Think through the structure that makes sense.
• Take time to collect your thoughts before you rush in and start speaking.
• Pause throughout and ask for feedback. This helps your interviewer stay engaged, collaborate with you, and redirect if you're heading off course.
• Don't monologue. Outside of the "Why" pitch and closing summary, don't be too verbose. Try to speak more choppy and bullet-like if it's natural enough.

Resources

And finally, here are some resources that helped inform this write-up:

• Master the Product Sense Interview
• The Definitive Guide to Mastering Product Sense Interviews
• How I Prepared for Meta PM Interviews: Product Sense
• How to Interview Product Managers
• Product Sense/Design Interviews: Common Mistakes
• Product Sense/Design Interviews: How to Answer
• PS Mock: Brian K Interviews Ben (Design VR Product for Elderly)
• Google Product Manager Mock Interview: Improve Headspace
• Meta Product Sense interview (with Meta PM)

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After 4 exciting years, I’m parting ways with Metabase. It’s been a fulfilling run, working with smart people to build the most delightful (or at least, least migraine-inducing) business intelligence tool out there, all while watching the team grow from 25 → 100+ employees.

When I joined Metabase as the 1st PM under our VP of Product, I was still a much more capable data scientist than product manager. I didn’t have deep experience as a PM, and I had to earn my chops on the job. There was risk involved on both sides, and looking back, all I can be is grateful it worked out how it did. I'm excited about what comes next, but before that, I would be remiss if I didn’t take a beat to reflect on what I learned during my time. So here are some of my favorite takeaways, both for future-Conor, and anyone else out there.

Shippable Units of Value

Slice up projects to ensure are shipping value as early as possible. This is critical as it not only enables you to ship faster, it also mitigates the risk that comes with spending a long time trying to build the One Perfect Thing that may or may not resonate. It's also way more fun!

Getting to a place where you have shippable units of value however, is a bit of both art and science. One thing I found is that it's best to think about projects or initiatives through this frame as early as possible, and collaborate closely with engineering during this time. How the project is structured or shaped is the biggest factor in how it can be broken out. If a "unit" is going to take multiple months, there's a good chance you aren't being creative enough.

Force for Progress

Done right, product management serves as a force for progress across different functions. The most effective lever for this in my time was short feedback loops and close collaboration. Throwing things over a wall and hoping to get back what you expect does not work, while the inverse, communicating clearly and frequently, sharing incremental updates, gut-checking alignment ahead of time, leads to good results much more often.

Early at Metabase, I was much more hesitant to check-in on things and ask questions. As I got more comfortable, I would grab teammates for a quick huddle or hit them up with questions often on a daily basis. I'd like to think this helped us ship good product, but at the very least, it helped avoid U-turns.

Articulating Problems + Strategy

Product docs and “arcs” as we called them are quite useful, particularly as a forcing function for thinking through a crisp definition of the problem (without being too prescriptive of the solution) or clearly stating a “Point B” and the intended strategy for getting there. I saw my own understanding of these artifacts evolve over my time. Take “arcs” or “initiatives” as an example:

• First attempt: “Visualizations: Opportunities + Plan” → No strategy outlining the thinking for how we’ll get there.
• Second attempt: “Visualizations: Opportunities + Strategy + Plan” → No depiction of an endpoint. Will we work on this forever?
• Third attempt: “Offer more expressiveness for viz creators: Point A + Point B + Strategy + Plan” → Framed around a solvable problem, with a strategy for how we'll get there, and endpoint that we aim to achieve.

I thought I knew what “strategy” meant before, but every time I tried to articulate my thinking it came out as a string of projects. It wasn’t until I was nudged to read Good Strategy Bad Strategy and applied it to the work we were doing, that things started to click for me.

Putting on Running Shoes

Business Intelligence is a pretty darn complex domain. The magic under the hood that needs to happen for a horizontal analytics tool to do it’s job is quite a lot. There’s millions of permutations of databases, modeling, queries, visualizations, settings, and more to consider. Even coming from a data science background, all the legos at play were largely opaque to me at first. And I was fine with that. I was doing my job, engineers were doing theirs.

As soon as I started taking moving to more technical product areas and taking on more complex initiatives, things got tricky. I was unable to be a “force for progress” since I lacked understanding. Now I’m much better at recognizing when I need to go deep so I can take off my "sandals," and put on my "running shoes," grab an engineer and talk through it, write through it, until I'm comfortable enough to move things forward like I should.

Chill User Experiences

Did I mention BI is pretty complex? Our differentiator was that it felt usable for non-technical folks. This is reflected in the Zen of Metabase well, and paired with the idea that products should be opinionated, it leads to some cool outcomes.

For example: Why add yet another setting, and the complexity and cognitive load that comes with it, when you have a strong opinion about what’s best? And if a setting is required, why make the user think about it when the system often has the information to make that call?

Arguably this framing is what resonated to me most at Metabase, and will stick with me over time. It’s a tough battle balancing new features, scaling to enterprise, and all that, with keeping the core of the product as “chill” and usable as possible, but it’s a fun battle that pays dividends.

Ambiguous Projects

Ambiguous projects are tough. When the problem or use case you are solving for is unclear, everything else is 100x harder. Even when you have that nailed down, reasoning through a huge solution space can be tricky as well. I’m still figuring this piece out, but I did see a lot of progress in my ability to steer these types of projects over my time. Some things that helped were:

• Goals and non-goals to point in the right direction.
• Open questions listed out and resolved through prototyping, design, product thinking, or research.
• Start with only the crux as a slice. Mock out anything that’s not risky from an implementation or product standpoint. It should feel like a toy at first. It won’t be connected to everything, but people should want to use it and be disappointed they can’t.
• When that's feeling good: Map out adjacent slices, middle-out, to take on next. Keep iterating for usability and completeness.

Miscellaneous Thoughts

Lastly, I’ll leave you with some stray ideas and learnings. No need for waxing poetic about these:

• Walking the line between thoughtful and moving fast at a startup is tough. I think we did it fairly well, but it requires being very intentional about when to “go” and “pause and think” at all times.
• I worked with people from all sorts of cultures, as we spanned 30+ countries last I checked. It was challenging, but more than that, incredibly cool. I learned a lot about the world and how people think.
• Open source is awesome. I’ve never gotten so much feedback and interacted with so many caring customers on a daily basis.

Conclusion

I’m sure I’m forgetting a bunch, and recency bias is a hell of a drug, but that’ll have to do as a stab at putting four exciting years into words. I’ll continue rooting on the team at Metabase, and I’m excited to see what they cook up next.

As for myself, more to come! I’m actively exploring opportunities and figuring out what I want to get into next. Shoot me an email if you’re interested in chatting or simply want to say what’s up. Feels good to be writing again. Godspeed, folks.

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Today I turned 29 and I can't help but notice that this birthday isn't hitting quite as hard as previous years. I don't quite have an answer for why. Maybe it's part of getting older. Maybe it's more stability in my day-to-day than in years past. If it's the latter, then that's set to change.

On the career side, I'm parting ways with Metabase and looking for a new gig after 4 years. On the life side, I recently got engaged to my wonderful fiancé. Things are going to look different a year from now, and I'm truly excited about that. Bring on the good, bad, and everything in between. Now without further ado, here are the things that I've learned and leaned on.

Author’s note: I’ve added a ⭐️ next to the principles that are new this year. This helps me see how my mindset changes from one post to the next.

1. Both bad and good things happen in waves.
2. Clear communication can help circumvent many types of problems. ⭐️
3. There’s nothing more important than relationships with those you care about.
4. Don’t treat mysteries as puzzles. Not everything can be answered.
5. Taste matters. Details matter. ⭐️
6. In all things, double down on what works.
7. Experience stretching steals wonder from life. Appreciate the simple.
8. Most decisions should be made on 1-2 variables alone.
9. Control the things you can control. ⭐️
10. Don't latch your identify onto outcomes. They won't last forever.
11. Take time to understand how you have been programmed.
12. You can’t enjoy highs without experiencing lows. Life is a pendulum.
13. Nobody can teach us the things that matter in life.
14. Great things come from showing up day after day. ⭐️
15. A little gratitude goes a long way.
16. Comfort isn’t weakness.
17. Find little things to care about. Even if they are silly.
18. Breakdowns can be essential to dislodge us from an undesirable state.
19. Don’t overreact when you feel stuck.
20. The worst case scenario isn’t as bad as you think it is. ⭐️
21. Learning new things rarely disappoints as a source of fulfillment.
22. Life doesn’t get easier. You’ll never “have it all figured out,” and that’s okay.
23. Move around a little bit every morning. You’ll feel better. ⭐️
24. Breathe. Breathe again. Breathe one more time. Repeat.
25. Rituals create meaning in a world where meaning is hard to find.
26. Happiness is often finding the right balance of consistency and novelty. ⭐️
27. The things that are worthwhile are never easy.
28. Make time for reflection. It doesn’t happen naturally.
29. Things aren’t nearly as black-and-white as you think they are.

If you're interested in more principles or how my perspective has shifted over time, you can find reflections from previous years below. I hope you found something meaningful here. See you next year.

• 28 Principles for 28 Years
• 27 Principles for 27 Years
• 26 Principles for 26 Years
• 25 Principles for 25 Years
• 24 Principles for 24 Years
• 23 Principles for 23 Years
• 22 Principles for 22 Years

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We often focus on the “right” way to do things, but just as important, is the “wrong” way to go about things. I’ve recently become much more aware of an anti-pattern that I keep running up against: Black and white thinking.

Black and white thinking is what it sounds like: it’s a thought pattern where you frequently think in absolutes. More often than not, this takes the shape of “If X then Y” in my head:

• If I don’t wake up on time, I won’t have a good day.
• If we don’t build a new feature a certain way, it won’t be successful.
• If I start something, I have to finish it now.

You get the picture. This anti-pattern appears in my personal life, work life, and just about everywhere in between. Over and over again. It’s a tricky thought process to catch in the act, and when I fail to catch myself, I suspect I’m about 20% less happy and effective as a decision maker.

Why this happens

In my experience, the main reason this happens is a discomfort with uncertainty. I like understanding things, and I don't like how it feels when I lack understanding. So I reduce, simplify, and distill things down to a system or set of concepts, principles that I can understand. My newsletter is called Oversimplified, for Christ’s sake. This approach kicks ass for problem solving and decision making in many contexts, but as they say, when your favorite tool is a hammer, everything looks like a nail.

Some problems, decisions, and concepts aren’t black and white, and don’t benefit from being simplified to that extent. Often it’s a spectrum. Often there are shades of grey. It’s important to acknowledge that first and orient yourself, before then deciding whether or not simplifying is appropriate.

What’s worked for me

While I'm still figuring out how to be more mindful of this anti-pattern, the main tool that has worked for me so far is self-talk. Reminding myself constantly that things aren’t black and white, that my thoughts aren’t necessarily reflective of reality. It’s okay to simplify, but it’s dangerous to do it unconsciously.

You're never going to be perfect. I still suspect most of the time I don’t catch myself and this anti-pattern flies under the radar. But if you can catch it and interrogate that way of thinking, it makes a huge difference. If you made it this far, I hope this helps get the gears turning, and maybe even spark something in your mind next time you catch yourself thinking “If X then Y” or using language like “always.” Best of luck out there.

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A Man Without a Country is a collection of essays from author Kurt Vonnegut. It’s a short and informal read, like chatting with a friend over a cup of coffee, a friend with uniquely lighthearted and thoughtful views. The essays cover a lot of ground, but the main themes that stood out to me were around gratitude, humor, society, and humanistic values. I enjoyed it quite a bit. These were the quotes that stuck with me:

Quotes

• Do you realize that all great literature — Moby Dick, Huckleberry Finn, A Farewell to Arms, The Scarlet Letter, The Red Badge of Courage, The Iliad and The Odyssey, Crime and Punishment, The Bible, and “The Charge of the Light Brigade”—are all about what a bummer it is to be a human being? (Isn’t it such a relief to have somebody say that?)
• Why had it taken me twenty-three years to write about what I had experienced in Dresden? We all came home with stories, and we all wanted to cash in, one way or another. And what Mary O’Hare was saying, in effect, was, “Why don’t you tell the truth for a change?”
• Electronic communities build nothing. You wind up with nothing. We are dancing animals. How beautiful it is to get up and go out and do something. We are here on Earth to fart around. Don’t let anybody tell you any different.
• When you get to my age, if you get to my age, and if you have reproduced, you will find yourself asking your own children, who are themselves middle-aged, “What is life all about?” I have seven kids, three of them orphaned nephews. I put my big question about life to my son the pediatrician. Dr. Vonnegut said this to his doddering old dad: “Father, we are here to help each other get through this thing, whatever it is.”
• “Welcome to Earth, young man,” I said. “It’s hot in the summer and cold in the winter. It’s round and wet and crowded. At the outside, Joe, you’ve got about a hundred years here. There’s only one rule that I know of: Goddamn it, Joe, you’ve got to be kind!”
• I’m startled that I became a writer. I don’t think I can control my life or my writing. Every other writer I know feels he is steering himself, and I don’t have that feeling. I don’t have that sort of control. I’m simply becoming.
• And his principal complaint about other human beings was that they so seldom noticed it when they were happy. So when we were drinking lemonade under an apple tree in the summer, say, and talking lazily about this and that, almost buzzing like honeybees, Uncle Alex would suddenly interrupt the agreeable blather to exclaim, “If this isn’t nice, I don’t know what is.”

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I turned 28 years old a few weeks ago. It feels alright. I’m both as grateful as ever, and things are as hard as ever. I’ve written some version of this post each year, for the last 6 years. When I started this series in 2018, I think I viewed it as a way to both catalog and share acquired ”wisdom” with others:

I don’t know if all of these principles will resonate with anyone else, or even if they’ll still resonate with me when I look at this a year from now. Some of them probably won’t. We are constantly growing, adapting, and transforming. Nothing is static. However, the fact still remains that these ideas helped make me who I am today.

It’s funny that the older I get, the less I believe that I have any worthwhile “wisdom” or “principles” to share with others. Part of that is self-deprecation, but the other part holds truth: Nobody really knows.

You can read a million pieces of advice, self-improvement books, and actionable insights. Life, happiness, and fulfillment aren’t solvable problems. We’re all just doing our best. So I think that's what this post really is. It’s a handful of ideas that are helping me do my best, at this specific point, after 28 years on this pale blue dot. Maybe they are able to spark something for you.

Author’s note: I’ve added a ⭐️ next to the principles that are new this year. This helps me see how my mindset changes from one post to the next.

1. There’s nothing more important than relationships with those you care about.
2. Both bad and good things happen in waves.
3. Confrontation doesn’t equal conflict. It’s how you go about it.
4. Don’t treat mysteries as puzzles. Not everything can be answered. ⭐️
5. In all things, double down on what works.
6. Experience stretching steals wonder from life. Appreciate the simple. ⭐️
7. Most decisions should be made on 1-2 variables alone.
8. You’re probably taking parts of your life far too seriously.
9. Don't latch your identify onto outcomes. They won't last forever.
10. Take time to understand how you have been programmed.
11. Work backwards from the outcomes you want to see.
12. You can’t enjoy highs without experiencing lows. Life is a pendulum. ⭐️
13. Nobody can teach us the things that matter in life.
14. Explore the perspectives that you disagree with most.
15. Don’t overreact when you feel stuck. ⭐️
16. A little gratitude goes a long way.
17. Comfort isn’t weakness.
18. Find little things to care about. Even if they are silly.
19. Breakdowns can be essential to dislodge us from an undesirable state. ⭐️
20. Learning new things rarely disappoints as a source of fulfillment.
21. Life doesn’t get easier. You’ll never “have it all figured out,” and that’s okay.
22. Breathe. Breathe again. Breathe one more time. Repeat. ⭐️
23. Rituals create meaning in a world where meaning is hard to find. ⭐️
24. Intelligence doesn’t mean pessimism.
25. The things that are worthwhile are never easy.
26. Make time for reflection. It doesn’t happen naturally.
27. Ambition can also be desire to preserve the current state. ⭐️
28. Things aren’t nearly as black-and-white as you think they are.

If you're interested in running back the tape, you can find reflections from previous years below. I hope you found something meaningful here. See you next year.

• 27 Principles for 27 Years
• 26 Principles for 26 Years
• 25 Principles for 25 Years
• 24 Principles for 24 Years
• 23 Principles for 23 Years
• 22 Principles for 22 Years

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There are a seemingly endless number of ways to make a living today. This optionality can paralyze young people, and rightfully so, as it all feels very permanent and important. But it doesn’t have to be that way. In the rest of this post, I'll outline an alternative way for thinking about your career.

Sampling the menu

The gist of this is pretty simple: try out different roles and environments throughout your career. Sample different values across both of these variables until you feel comfortable. Then try something else. People don’t think of their career as a 40-year expedition, but for most of us, that’s precisely the case. The reality is that it’s unlikely the first thing you pick up will be what you’re best at or fulfills you the most. So why not explore a bit?

If you meet a certain threshold of privilege as a knowledge worker, then you can hop from role to role fairly seamlessly in today’s work culture. Remote work going mainstream has certainly helped this, as you can hop from job to job without having to pick up and move. So why not sample the menu a bit before you pick the entree you'll be having for years and years? Try different roles in different environments for 1-3 years each, or until the learning curve flattens, or until you get bored or dissatisfied. Then try something else.

Why this is nice

• You develop a wide array of skills and learn what you enjoy most.
• These skills interact with eachother in ways you may or may not foresee. Even if you won’t be a designer long-term, that design skillset will make you a better PM or SWE in the future.
• You can’t predict the future, so it makes you more resilient to change and better at learning. If GPT-12 comes along and automates roles that we know and love today, then you have other skillsets to fall back on.
• It’s fun! If you enjoy the road to 80% competency more than the road from 80% → 90% competency like I do, then picking up new skills and learning the terrain is an energizing and fulfilling way to spend your days.

Why this isn't all that nice

• It’s more work. The effort you put in to optimize a certain skillset is going to be less stressful and more comfortable than picking up something totally new. Doing bootcamps, courses, etc. requires a certain degree of daily commitment that has to be internally motivated and driven forward. There are days where it’s exhausting.
• Your ‘competitors’ will be more specialized. If you’re extremely competitive and want to be the best at one thing, this approach may not be the best one for you. You’ll watch as your colleagues and friends specialize further and are flat-out better with more experience than you at certain tasks.
• You won’t make as much money. At least in the short-term, hopping from role to role will usually require you to forgo a raise or even in some cases, take a cut. This makes sense. From an on-paper assessment, a L2 PM is less valuable to the company than a L5 Sales Engineer will be. They won’t be as effective, and therefore may not get paid as much.
• Your title won’t grow and you won’t seem as impressive. It’s way easy to gain respect of your colleagues and friends when you stay in your lane, climb the ranks, and your title grows accordingly. Introducing yourself to someone new at a networking event can be an ego hit.

Wrapping up

Unintentionally, I've ended up doing this in my own career:

• Data science for 2 years at bigger companies
• Growth for 2 years at a small startup
• Product for 3 years at a medium-sized startup

I've enjoyed all of these different roles and company sizes, all for different reasons. However, the one commonality between them was that I enjoyed learning new things. That's what I'm optimizing for above all else. You don't have to "sample the menu" to do that, but for those that are ambitious, become bored easily, and are motivated by up-leveling skills, it's a very viable option.

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It’s that time of the year when I reflect on another trip around the sun. I’m turning 27 years old and unsurprisingly I don’t feel different than I did yesterday. But if I turn the clock back a year earlier, it does feel quite different now. From an output perspective, I’ve been less productive. I’ve felt burnt-out and have lacked energy for periods of time. It’s been a bit of an internal roller coaster. I’m also happier and more at peace with where I am in my life than I ever have been before. Weird, right?

I don’t have all the answers, but things are good. I’m grateful. And that’s all there is to be. Now without further ado, here are the ideas and principles that are top of mind for me 27 years into this wild ride.

Author’s note: I’ve added a ⭐️ next to the items that are new this year. Part of the fun of this is seeing how my mindset changes from year to year. This should make that more evident.

1. Nothing is preventing you from being happy. Even if it seems like it.
2. There’s nothing more important than the relationships with people you care about. ⭐️
3. Confrontation doesn’t equal conflict. It’s how you go about it.  ⭐️
4. Both bad and good things happen in waves.
5. Both in business and life, double down on what works.
6. You’re probably taking parts of your life far too seriously. ⭐️
7. Take time to understand how you have been programmed.
8. Work backwards from the outcomes you want to see.
9. You can’t enjoy the highs without experiencing the lows. Ride the wave.
10. Playing the long game is a superpower.
11. Therapy works. There’s a good reason people are passionate about it. ⭐️
12. Nobody can teach us the things that matter in life.
13. Explore the perspectives that you disagree with most.
14. The things that are worthwhile are never easy.
15. When a measure becomes a target, it ceases to be a good measure.
16. Most decisions should be made on 1-2 variables alone.
17. Don't latch your identify onto outcomes. They won't last forever. ⭐️
18. A little gratitude goes a long way.
19. Learning new things rarely disappoints as a source of fulfillment. ⭐️
20. Comfort isn’t weakness.
21. Intelligence doesn’t mean pessimism.
22. Life doesn’t get easier as you age. You’ll never “have it all figured out,” and that’s okay. ⭐️
23. When you don’t want to do something, interrogate the reason.
24. Find little things to care about. Even if they are silly.
25. Make time for reflection. It doesn’t happen naturally.
26. Actively limit the things you depend on.
27. Things aren’t nearly as black-and-white as you think they are. ⭐️

If you're interested in running back the tape, you can find all my reflections from previous years below. I hope you found something here that resonated. See you next year.

• 26 Principles for 26 Years
• 25 Principles for 25 Years
• 24 Principles for 24 Years
• 23 Principles for 23 Years
• 22 Principles for 22 Years

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The reality of our lives as knowledge workers is that we're looking at a 40-50 year career. There's recipes for avoiding this. Find multiple streams of income. Keep spending at a minimum. Retire early. You're probably familiar with the "FIRE" calling card. But for most of us, we've got decades and decades of career left. This gets much less intimidating and more exciting when you have a sense of how and when to change the work we do. Peter Drecker's Managing Oneself provides provoking questions and tools for doing precisely this. It's a short, and worthwhile read. These were the quotes that stuck with me:

Quotes

• We have to stay mentally alert and engaged during a 50-year working life, which means knowing how and when to change the work we do.
• The only way to discover your strengths is through feedback analysis. Whenever you make a key decision or take a key action, write down what you expect will happen. Nine or 12 months later, compare the actual results with your expectations.
• First and foremost, concentrate on your strengths. Put yourself where your strengths can produce results.
• And yet most people—especially most teachers and most organizations—concentrate on making incompetent performers into mediocre ones. Energy, resources, and time should go instead to making a competent person into a star performer.
• The explanation is that writers do not, as a rule, learn by listening and reading. They learn by writing. Because schools do not allow them to learn this way, they get poor grades.
• When I ask people, “How do you learn?” most of them know the answer. But when I ask, “Do you act on this knowledge?” few answer yes. And yet, acting on this knowledge is the key to performance; or rather, not acting on this knowledge condemns one to nonperformance.
• That is the mirror test. Ethics requires that you ask yourself, What kind of person do I want to see in the mirror in the morning?
• But most people, especially highly gifted people, do not really know where they belong until they are well past their mid-twenties. By that time, however, they should know the answers to the three questions: What are my strengths? How do I perform? and, What are my values? And then they can and should decide where they belong.
• Successful careers are not planned. They develop when people are prepared for opportunities because they know their strengths, their method of work, and their values. Knowing where one belongs can transform an ordinary person—hardworking and competent but otherwise mediocre—into an outstanding performer.
• The first is to accept the fact that other people are as much individuals as you yourself are. They perversely insist on behaving like human beings. This means that they too have their strengths; they too have their ways of getting things done; they too have their values. To be effective, therefore, you have to know the strengths, the performance modes, and the values of your coworkers.
• Today, however, most work is knowledge work, and knowledge workers are not “finished” after 40 years on the job, they are merely bored.
• People who manage the second half of their lives may always be a minority. The majority may “retire on the job” and count the years until their actual retirement. But it is this minority, the men and women who see a long working-life expectancy as an opportunity both for themselves and for society, who will become leaders and models.

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I’ve been a full-time Product Manager for a little over 1.5 years at this point. Like most people in the role, I didn’t formally learn how to PM. I picked it up on the fly and went deep when gaps in my skillset appeared. I’m still doing that, and the most recent gap I discovered was around developing and articulating a strategy in different product areas. I was recommended Good Strategy Bad Strategy: The Difference and Why It Matters, to help out.

I’m happy to say it did the trick, and while I’m still putting learnings into practice, I’m feeling a lot more confident in the realm of strategy as it applies to product. While I'd highly recommend taking in the whole book, if you're looking for a taste, these are the quotes that especially stuck with me:

Quotes

• The core of strategy work is always the same: discovering the critical factors in a situation and designing a way of coordinating and focusing actions to deal with those factors.
• A good strategy does more than urge us forward toward a goal or vision. A good strategy honestly acknowledges the challenges being faced and provides an approach to overcoming them.
• Like a quarterback whose only advice to teammates is “Let’s win,” bad strategy covers up its failure to guide by embracing the language of broad goals, ambition, vision, and values.
• Rather, the term “strategy” should mean a cohesive response to an important challenge. Unlike a stand-alone decision or a goal, a strategy is a coherent set of analyses, concepts, policies, arguments, and actions that respond to a high-stakes challenge.
• Many people assume that a strategy is a big-picture overall direction, divorced from any specific action. But defining strategy as broad concepts, thereby leaving out action, creates a wide chasm between “strategy” and “implementation.”
• A good strategy includes a set of coherent actions. They are not “implementation” details; they are the punch in the strategy. A strategy that fails to define a variety of plausible and feasible immediate actions is missing a critical component.
• Strategy is about how an organization will move forward. Doing strategy is figuring out how to advance the organization’s interests. Of course, a leader can set goals and delegate to others the job of figuring out what to do. But that is not strategy.
• A good strategy has an essential logical structure that I call the kernel. The kernel of a strategy contains three elements: a diagnosis, a guiding policy, and coherent action. The guiding policy specifies the approach to dealing with the obstacles called out in the diagnosis. It is like a signpost, marking the direction forward but not defining the details of the trip. Coherent actions are feasible coordinated policies, resource commitments, and actions designed to carry out the guiding policy.
• The most basic idea of strategy is the application of strength against weakness. Or, if you prefer, strength applied to the most promising opportunity.
• Having a coherent strategy—one that coordinates policies and actions. A good strategy doesn’t just draw on existing strength; it creates strength through the coherence of its design.
• Good strategy requires leaders who are willing and able to say no to a wide variety of actions and interests. Strategy is at least as much about what an organization does not do as it is about what it does.
• Half of what alert participants learn in a strategy exercise is to consider the competition even when no one tells you to do it in advance.
• “Good,” I say, and point out to everyone that Wal-Mart’s policies fit together—the bar codes, the integrated logistics, the frequent just-in-time deliveries, the large stores with low inventory—they are complements to one another, forming an integrated design. This whole design—structure, policies, and actions—is coherent. Each part of the design is shaped and specialized to the others.
• Their insight was framed in the language of business strategy: identify your strengths and weaknesses, assess the opportunities and risks (your opponent’s strengths and weaknesses), and build on your strengths. But the power of that strategy derived from their discovery of a different way of viewing competitive advantage—a shift from thinking about pure military capability to one of looking for ways to impose asymmetric costs on an opponent.
• If you fail to identify and analyze the obstacles, you don’t have a strategy. Instead, you have either a stretch goal, a budget, or a list of things you wish would happen
• Importantly, opportunities, challenges, and changes don’t come along in nice annual packages. The need for true strategy work is episodic, not necessarily annual.
• To help clarify this distinction it is helpful to use the word “goal” to express overall values and desires and to use the word “objective” to denote specific operational targets. Thus, the United States may have “goals” of freedom, justice, peace, security, and happiness. It is strategy which transforms these vague overall goals into a coherent set of actionable objectives—defeat the Taliban and rebuild a decaying infrastructure. A leader’s most important job is creating and constantly adjusting this strategic bridge between goals and objectives.
• Good strategy works by focusing energy and resources on one, or a very few, pivotal objectives whose accomplishment will lead to a cascade of favorable outcomes.
• Thus, the objectives a good strategy sets should stand a good chance of being accomplished, given existing resources and competence. (See the discussion of proximate objectives in chapter 7.) By contrast, a blue-sky objective is usually a simple restatement of the desired state of affairs or of the challenge. It skips over the annoying fact that no one has a clue as to how to get there.
• When a leader characterizes the challenge as underperformance, it sets the stage for bad strategy. Underperformance is a result. The true challenges are the reasons for the underperformance. Unless leadership offers a theory of why things haven’t worked in the past, or why the challenge is difficult, it is hard to generate good strategy.
• Strategy involves focus and, therefore, choice. And choice means setting aside some goals in favor of others. When this hard work is not done, weak amorphous strategy is the result.
• Grove recalls the turning point in 1985 when he gloomily asked Intel’s chairman, Gordon Moore, “If we got kicked out and the board brought in a new CEO, what do you think he would do?” Moore immediately replied, “He would get us out of memories.” Grove recalls that he went numb and then finally said, “Why shouldn’t you and I walk out the door, come back and do it ourselves?”
• Strategies focus resources, energy, and attention on some objectives rather than others. Unless collective ruin is imminent, a change in strategy will make some people worse off. Hence, there will be powerful forces opposed to almost any change in strategy.
• The core content of a strategy is a diagnosis of the situation at hand, the creation or identification of a guiding policy for dealing with the critical difficulties, and a set of coherent actions
• A great deal of strategy work is trying to figure out what is going on. Not just deciding what to do, but the more fundamental problem of comprehending the situation.
• An explicit diagnosis permits one to evaluate the rest of the strategy. Additionally, making the diagnosis an explicit element of the strategy allows the rest of the strategy to be revisited and changed as circumstances change.
• A good guiding policy tackles the obstacles identified in the diagnosis by creating or drawing upon sources of advantage
• A guiding policy creates advantage by anticipating the actions and reactions of others, by reducing the complexity and ambiguity in the situation, by exploiting the leverage inherent in concentrating effort on a pivotal or decisive aspect of the situation, and by creating policies and actions that are coherent, each building on the other rather than canceling one another out.
• Many people call the guiding policy “the strategy” and stop there. This is a mistake. Strategy is about action, about doing something. The kernel of a strategy must contain action. It does not need to point to all the actions that will be taken as events unfold, but there must be enough clarity about action to bring concepts down to earth. To have punch, actions should coordinate and build upon one another, focusing organizational energy.
• Good strategy and good organization lie in specializing on the right activities and imposing only the essential amount of coordination.
• A good strategy draws power from focusing minds, energy, and action. That focus, channeled at the right moment onto a pivotal objective, can produce a cascade of favorable outcomes. I call this source of power leverage
• To achieve leverage, the strategist must have insight into a pivot point that will magnify the effects of focused energy and resources.
• A pivot point magnifies the effect of effort. It is a natural or created imbalance in a situation, a place where a relatively small adjustment can unleash much larger pent-up forces.
• A “threshold effect” exists when there is a critical level of effort necessary to affect the system. Levels of effort below this threshold have little payoff. When there are threshold effects, it is prudent to limit objectives to those that can be affected by the resources at the strategist’s disposal.
• One of a leader’s most powerful tools is the creation of a good proximate objective—one that is close enough at hand to be feasible. A proximate objective names a target that the organization can reasonably be expected to hit, even overwhelm.
• Phyllis’s insight that “the engineers can’t work without a specification” applies to most organized human effort. Like the Surveyor design teams, every organization faces a situation where the full complexity and ambiguity of the situation is daunting. An important duty of any leader is to absorb a large part of that complexity and ambiguity, passing on to the organization a simpler problem—one that is solvable. Many leaders fail badly at this responsibility, announcing ambitious goals without resolving a good chunk of ambiguity about the specific obstacles to be overcome. To take responsibility is more than a willingness to accept the blame. It is setting proximate objectives and handing the organization a problem it can actually solve.
• Therefore, the more uncertain and dynamic the situation, the more proximate a strategic objective must be.
• To concentrate on an objective—to make it a priority—necessarily assumes that many other important things will be taken care of
• A system has a chain-link logic when its performance is limited by its weakest subunit, or “link.” When there is a weak link, a chain is not made stronger by strengthening the other links.
• What kind of customer needs technical help to get their product into a can?” My question only evokes blank looks. I have lectured on how to tackle seemingly formless questions like this. The first trick is to replace general nouns with specific examples. I wait a moment, and then I do it for them, a concrete example of replacing the abstract with the concrete. “What about Coors, does it need technical assistance from can companies?”
• A good strategy is, in the end, a hypothesis about what will work. Not a wild theory, but an educated judgment.
• The problem with treating strategy as a crank-winding exercise is that systems of deduction and computation do not produce new interesting ideas, no matter how hard one winds the crank.
• Making a list is a basic tool for overcoming our own cognitive limitations. The list itself counters forgetfulness. The act of making a list forces us to reflect on the relative urgency and importance of issues. And making a list of “things to do, now” rather than “things to worry about” forces us to resolve concerns into actions.
• To guide your own thinking in strategy work, you must cultivate three essential skills or habits. First, you must have a variety of tools for fighting your own myopia and for guiding your own attention. Second, you must develop the ability to question your own judgment. If your reasoning cannot withstand a vigorous attack, your strategy cannot be expected to stand in the face of real competition. Third, you must cultivate the habit of making and recording judgments so that you can improve.
• What issues do you expect to arise in the meeting? Who will take which position? Privately commit yourself in advance to some judgments about these issues, and you will have daily opportunities to learn, improve, and recalibrate your judgment.
• Social herding presses us to think that everything is OK (or not OK) because everyone else is saying so. The inside view presses us to ignore the lessons of other times and other places, believing that our company, our nation, our new venture, or our era is different. It is important to push back against these biases. You can do this by paying attention to real-world data that refutes the echo-chamber chanting of the crowd—and by learning the lessons taught by history and by other people in other places.

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Product management can be a frustratingly broad field. There are a seemingly endless number of mental "muscles" to train at any given time. From strategy to research to prioritization to execution. Any one of those could be a full semester at a university, and you still would have lots to learn. There's a blog post to be written for each, but in this post I'll focus on a specific part of the role that has given me trouble over the last 1.5 years: shaping ambiguous projects.

Defining Ambiguous

Not all PM work is tough. There's always the easy stuff. Customer X says “Hey, buddy, we're going to churn if we don’t get Feature Y” and sometimes the aforementioned feature is straightforward. There's not a lot of wiggle room in terms of what the thing will look like, it's well-contained, and it fits well within the overall product strategy. Define the thing and ship it. Full speed ahead.

But not all projects fit this mold. Some projects have a greater degree of variance in how you might achieve the desired result. The best initial approach isn't obvious, and when something does come to mind, it doesn't exactly inspire confidence. In my current gig at Metabase, this is around 25% of the projects that I work on. There's plenty of low-hanging fruit out there still, but often the most valuable stuff comes with ambiguity. It's not the micro design decisions that make these projects tough. It's the fundamental decision points that will define the project and set you down a certain path if continued.

The Journey

You can start shaping these ambiguous projects like you would any other, but eventually you hit a point where your internal monologue goes "I don't know what we should do to solve this," and that's where things get interesting.

Most recently, I was tasked with figuring out how to provide companies with a way to curate and and display the most important dashboards, charts, external links, etc. on their homepage. Sounds simple enough. But when you get into it, there are a dozen ways to tackle the problem, and each of them sets us down an explicit path. Should we provide a sandbox-like experience? Should we do something more structured and simple with links alone? Should we do the "dumbest thing" and just provide a Markdown box? Or should we try to be more prescriptive and help customers build out their homepage with a wizard-like experience? I walked through the implications of each of these options and mapped them to customer use cases, but I still didn't know.

When you hit this point, at least personally, my default state is paralysis. I’m a very analytical person by nature. I like working alone. So sometimes I struggle to lean on others. My instincts say to take this problem, go into a deep, dark cave for several days to weeks, and deconstruct it until I’m happy with a decision.

Practically, this often doesn’t lead to the best outcome because in truly ambiguous projects, there is rarely a piece of the puzzle just waiting to be picked up and make the choice for you. It can be incredibly hard to reason through these questions alone. And we're about making things easier. So here's the playbook that I've been using lately.

A Playbook

🧭 Map out the territory

Start out in analysis mode. Break down the problem you are trying to solve and segment it into sub-problems if it makes sense. Then map out the possible solution space. What are all the ways you could address this problem? Decompose each one. Think about the pros and cons of each. Think about the open questions that come with each. Make sure you write it down. You may still not have an answer, and that's perfectly okay, but you should have a clearer idea of the territory that you are working with, and the ability to better communicate that territory with others.

🤝 Lean on internal partners

Ask others for help! You don’t have to figure it all out on your own. Pull in engineers and designers with different viewpoints to help you reason through the problem, solution space, and outstanding open questions. Through these conversations, you should be able to resolve some open questions and narrow in on a smaller set of viable solutions. Take notes and feed any adjustments back into your mental model. Think through things, and make a call. It may not be the right one, and that's okay. Which brings us to the next point...

🔄 Try it out and iterate

The problem isn't "solved" when you come to a decision. You'll have to try it out to achieve a significant degree of confidence. Keep implementation cheap and structure the project in a way that you don't expend too many resources. Go with a prototype, or break out a slice of the project that can give you enough clarity. Once that is ready to play with, go back into analysis mode. Revisit the initial problem and open questions.

Is it solving the core problem that you set out to solve in the first place? Or have you gotten too in the weeds trying to solve specific open questions? Are things coherent? Is your story about how this works clear enough? Reassess. Then iterate some more. And do it over and over again. Until you have something you’re mildly proud of. It's not clean, and it's not perfect, but this is what I've found to work.

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Happy new year! It’s time for another annual review in which I look back on how the last 365 days turned out for me. I'll follow a similar structure as last year with these two prompts:

• What went well this year?
• What didn't go well this year?

Before we dive into the review itself, let's get the snapshot portion of this post out of the way. Keep in mind that lists like this always look more glamorous than they actually are:

• Finished up a 6-month digital nomad trial and settled back down in New York
• Improved a ton as a Product Manager at Metabase
• Went on several memorable trips with friends including Las Vegas and Brazil
• Surpassed 3 years in a relationship with my partner
• Published 14 blog posts
• Published 13 newsletter issues
• Finished 6 books

What went well?

🫂 Spending time with those I care about

It proved difficult to spend quality time with the important people in my life when I was in digital nomad-mode. At least to the extent that I would like. Luckily after settling back into a full-time apartment lease, that changed for the better. I saw family members on multiple occasions, was able to hang out with friends again, and spent more time with my partner. All extremely good things that made this year a memorable one.

🤝 Leveling up as a Product Manager

When I wasn’t spending time with others, most of my focus throughout the year went into my role as Product Manager at Metabase. I’ve been doing the PM thing for about 2 years now and I still see “opportunities for growth” popping up all the time. This can be discerning at times, but also tells me I’m heading in the right direction, which is encouraging through the right lens.

While my first year as a PM was about getting the excecution-side of the gig down, this past year felt different, with much more emphasis on managing and running projects at increasingly larger scales. I’m still not great at it, but it feels nice to see concrete improvement in the area. It helps when you work with smart people on a cool product.

What didn’t go well?

📝 Keeping up with creative habits

This is a disappointing one. Writing and reading are some of the most fulfilling activities for me, yet I let myself get away from spending time on them this past year. I need to get better at managing my bandwidth between my full-time job and creative projects. I used to block off an hour for this exact purpose before I started my work day. That worked really well for years.

Since I switched to early-stage startup life and more recently, switched to product management, I’ve struggled to exert the necessary discipline to respect that hour-long block of time in the mornings. Waking up and seeing 3 new Slack notifications where I’m blocking James, Katherine, and Omar from doing their jobs is a tantalizing prospect. It’s tough to see that and then let it sit for an hour, even though I know that I would be more productive long-term and happier short-term if I waited and gave myself that block of creative time. I just need to get better at following through, but hey, this blog post is a start. Let’s keep it going.

🏥 Discipline over health habits

Lack of discipline is a bit of a theme with this “What didn’t go well?” section. I was too lenient with myself in certain areas, which then turned into unhealthy habits, specifially two concrete habits.

First is overeating. I love eating, and don’t really have issues with weight gain, but man do I have trouble stopping once I get going. This normally results in me feeling uncomfortable or lazy as hell. And I’m pretty sure it’s not great for longevity. Second was substance control. I’ve slowly started smoking more and more since I moved to New York. It kind of snuck up on me, but I’ve realized that the nicotine dependence is real. I’m 2 weeks off it right now and I plan to continue that. As a bonus, it’s already making mornings easier to handle and headaches less frequent.

Appendix

📚 Books I read

I read 6 non-technical books last year. I really got away from my nightly habit towards the end of last year which is a bummer. We’ll do better in 2023 but for now, here’s the list in chronological order from first to last:

• Four Thousand Weeks
• The Making of the Prince of Persia
• Surely You're Joking, Mr. Feynman!
• Foundation
• The Book: Playing the Percentages in Baseball
• The 4-Hour Body

📝 Blog posts I published

I wrote 14 new blog posts. This is much less than the 33 I shipped last year but better than I thought. I was actually on a good pace until the end of the year. I could do a lot more. I just need to show up. Here’s the list:

• This is Water
• 26 Principles for 26 Years
• Theory, Explained
• Meditations on Time
• On Multiplayer Analytics
• Self-Serve Analytics Building Blocks: A Spectrum
• 6 Months Digital Nomading: A Review
• Notes on Surely You’re Joking, Mr. Feynman
• Making Dashboards Suck Less
• Notes on The Making of Prince of Persia
• Notes on Four Thousand Weeks
• Towards Modern Data Apps
• Quick Rules for Travel
• 2021 Year in Review

📬 Newsletter issues I published

I sent out 13 issues of Oversimplified this past year. This is the lowest mark that I started the initial version of this newsletter some seven years ago. Much like writing and reading, this got away from me in the back-half of the year. Plan on hearing from me more often this time around. Here’s the archive:

• Oversimplified: Volume 135
• Oversimplified: Volume 134
• Oversimplified: Volume 133
• Oversimplified: Volume 132
• Oversimplified: Volume 131
• Oversimplified: Volume 130
• Oversimplified: Volume 129
• Oversimplified: Volume 128
• Oversimplified: Volume 127
• Oversimplified: Volume 126
• Oversimplified: Volume 125
• Oversimplified: Volume 124
• Oversimplified: Volume 123

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This will be a short post, but I wanted to share a concept that has been helping me out a bunch the last few days. I won’t bury the lead here. It’s not novel. It’s just awareness.

Reading and writing about awareness has always felt shallow to me. Personally, the only times in which I’ve truly appreciated awareness are when I find myself experiencing it firsthand. When you feel a tinge of negativity and are able to move past it. When you go to launch Instagram and realize you can hold off. When you are all alone but still break a smile, because you realize things are good in that moment. It’s incredibly easy to let these moments pass. I find that I’m happier when I notice them.

The recent catalyst that has temporarily helped me out here (it won’t last forever without a whole lot of effort and intention) was a commencement speech from David Foster Wallace titled This is Water. I really think this speech is fucking awesome, to put it eloquently. I’ve adopted “This is Water” as a mantra that triggers awareness, and it’s working well. I highly recommend you watch the speech in its entirety, but I’ll share two concepts inspired from it that have really stuck with me:

Life wears you down

The day-to-day grind of life can and will wear you down. You don’t realize this when you’re young, but sooner or later it hits you. As novelty degrades, things become a hassle. The first day in the office is amazing. Then you start noticing more and more the slow elevators, crowded commute, and Tom, who is always just so passive aggressive, man. Your head fills up with unconscious negative thoughts. You can control and reframe these thoughts if you catch them, but first you need the awareness to catch them. That’s the tough part. It’s achievable, but tough. Even with concentrated effort.

We all worship

When life wears us down, we turn to worshipping. Stick with me on this. Worshipping is not exclusive to religion. Whether it’s your career, money, beauty, or people. We all worship things in life. It’s up to you to be aware of what you worship and audit accordingly. Ensure you worship things that are healthy. Both mentally and physically. Things that make you happy. Things that are sustainable. Even if they are silly. Personally, I think of sports here. At the end of the day, it’s a game. But checking in on how the Yankees did each day makes me happy. I’m aware of it, and it keeps me a little more sane when life wears me down. That seems alright to me.

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Another birthday has come and gone. This time I’m 26 years old. On paper, things look similar to where I was last year. I’m working in a different role at a different company, but I’m still in New York and in terms of my day-to-day life and how I spend my time, not a ton has changed.

Mentally, on the other hand, the feeling is different. There are things that gnaw at me of course, often in pretty intense ways, but I’m more content than I have been in a while. As I talked about in Meditations on Time, I’m at peace. Or at least mindful of peace as a goal, which is quite different from the “improvement at all costs” attitude that I’ve championed in the past. And while a past version of Conor would have been skeptical of this, I feel like I’m still ambitious, productive, and effective.

Things are good, and they won’t always be good, so I’m grateful. Now without further ado, let’s get more concrete by laying out the ideas and principles that shape where my mind is at 26 years into life on this pale blue dot.

Author’s note: I’ve added a ⭐️ next to the items that are new this year. Part of the fun of this is seeing how my mindset changes from year to year. This should make that more evident.

1. Time moves fast. Mindfulness is the antidote.
2. Nothing is preventing you from being happy. Even if it seems like it.
3. Life is better with people you care about.
4. Both bad and good things happen in waves.
5. Both in business and life, always double down on what works.
6. Take time to understand how you have been programmed.
7. Work backwards from the outcomes you want to see.
8. You can’t enjoy the highs without experiencing the lows.
9. Playing the long game is a superpower.
10. Mental health is just as important as physical health, if not more.
11. Nobody can teach us the things that matter in life.
12. Explore the perspectives that you disagree with most.
13. The things that are worthwhile are never easy.
14. When a measure becomes a target, it ceases to be a good measure.
15. Most decisions should be made on 1-2 variables alone.
16. Don't identify with success. It won't last forever.
17. A little gratitude goes a long way.
18. Never stop learning. Especially outside of your career. ⭐️
19. Comfort isn’t always weakness. ⭐️
20. Intelligence doesn’t mean pessimism. ⭐️
21. You’ll never really “have your life together,” and that’s okay. ⭐️
22. When you don’t want to do something, interrogate the reason. ⭐️
23. Find things to care about. Even if they are silly. ⭐️
24. Make time for reflection. It doesn’t happen naturally. ⭐️
25. Actively limit the things you depend on. ⭐️
26. Go on walks and talk to people. It helps. ⭐️

If you're interested in running back the tape, you can find all my reflections from previous years below. I hope you found something here that resonated. See you next year.

• 25 Principles for 25 Years
• 24 Principles for 24 Years
• 23 Principles for 23 Years
• 22 Principles for 22 Years

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From my distant perspective into academia, it seems that theory is something of a holy grail in published papers. Presenting novel information is interesting. Being able to explain why that information looks the way it does is better.

It’s also more difficult, and not exclusive to academics. I saw instances of this all the time as a data scientist and now as a product manager, I still continue to see them.

Defining theory

First things first: What exactly is theory? My mental model is that theory is the why. When done right, it’s an explanation of the processes and systematic reasons for something occurring or not occurring. Another definition:

A theory is a well-substantiated explanation of an aspect of the natural world that can incorporate laws, hypotheses and facts.

You might be thinking this sounds like a close cousin of causality and I think that’s right. In my view, causality is a subset of theory. I’m open to being wrong on that.

Towards theory

Practically, theory comes to my mind in the context of presenting information to others. Whether that’s via a published paper in academia or a slide deck in the business world.

When you present information without theory, you are leaving the story in the hands of the reader or listener. Chances are high that they are going to go with the first story in their mind that fits with the findings that you provided. You are giving them an abstract piece of art and trusting them to decide what it is.

So what’s a better approach? Take things a step further and connect the dots. Don’t just present your findings. Present your hypotheses for why the findings are what they are. You’ve built up a mental model digging through data and putting together these findings, put that mental model on the page for readers.

State your findings. Propose a set of theories and point to the most probable. Simple, but powerful when done right.

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