Learning Days

Most of my workweek tends to quickly fill up with sporadic founder meetings, company diligence, and portfolio company support. Rarely can I find the luxury of uninterrupted work blocks to sit for hours on end and properly study anything I want to learn.

In light of this year’s theme around deep work, I’ve been experimenting with the concept of “Learning Days” where I pick any topic I’m interested in and spend a full day (Saturdays or Sundays) deep-diving into that topic.

My first two learning days (Artificial Intelligence/Machine Learning & Blockchain) were relatively unstructured as I’m still figuring out the best approach to these going forward.

So far, I’ve kicked off each learning day in the following manner:

  1. Wake up and head to the gym for a run (a healthy body is a healthy mind)
  2. Shower and make tea
  3. Create a new Google Doc and throw it up on my second external monitor to document the day’s notes / learnings
  4. Look for a Medium article where someone has already aggregated the best links / resources for learning the topic of choice. For example, my buddy Sam DeBrule compiled a massive list of curated AI / ML links which drastically helped to cut down the time I needed to spend digging around the web.(obviously you’ll want to do your own research but these types of aggregated resources provide a launching point for mapping out what you know / don’t know)
  5. Go through each article I find: read and reflect. Each article should provide foundational knowledge for the next but I try to question / probe everything I’m reading. I want to develop a sense of which authors know what they’re talking about vs. those that are regurgitating information / filling my head with incorrect information.
  6. In my first hour, I try to first understand the history behind the topic (i.e. when and why did AI / ML first come into existence, what worked and what failed, what catalysts are leading to breakthroughs now)
  7. Now that I have better context around how we got to this point, I’m better able to understand the current state of AI / ML as well as map out a hierarchy of subtopics (i.e. AI -> Machine Learning -> Deep Learning -> Neural Networks) that I’ll need to prioritize my learning around for the next few hours
  8. For each subtopic, I try to understand: what it is (literally, what is deep learning), how it works (deep learning uses neural networks? ok, how do neural networks work?), and how it’s used in practical business / life (Google Photos uses deep learning for face recognition? much wow). I was never a great academic and this last part helps me tie concepts I’m learning to the “real world” so I don’t forget them.
  9. I’m also careful to include my source links next to all of my Google Doc notes so I can easily reference them at a later time.
  10. At the end of the day, I’ll revisit all of the raw notes I’ve taken and take some time to organize / structure them in a readable format – the hope is that someone completely foreign to the topic could pick up my notes and easily understand what I’ve learned that day
  11. As an additional forcing function, I’ve tried to “Feynman Technique” the whole process by teaching my significant other everything I’ve learned. Teaching the subject matter helps me quickly figure out which concepts or subtopics I need to spend more time on. It also helps that she likes to play the “why why why” question game which really forces me to simplify each complex concept. After teaching the topic, I have a list of follow-up questions for myself that I need to dig into since I couldn’t easily explain them.

I’ve got a long ways to go with these Learning Days but I’m loving them and they’ve spurred a new love of learning that makes me even more excited to wake up every morning.


Consumer to Creator

SumoCon 2016 with Noah Kagan (SumoMe), Nathan Barry (ConvertKit), Ankur Nagpal (Teachable), Justin Jackson (MegaMaker)

In September 2016, I attended SumoCon, the first conference that SumoMe ever hosted in Austin, Texas. The photo above with Noah Kagan (SumoMe), Nathan Barry (ConvertKit), Ankur Nagpal (Teachable), and Justin Jackson (MegaMaker), represents one of the happiest and most symbolic moments of my life.

This was my first time meeting all of these guys in person, but I had already been using their products for several years. Without their products and companies, I most likely never would have become a “creator”.

Justin Jackson was one of the first “digital entrepreneurs” who I started following online. He had successfully launched a number of digital products including his popular ‘Marketing for Developers’ book and a lot of his writing taught and inspired me to think about how to create and sell digital products.

When I started Product Manager HQ, I used Noah Kagan’s SumoMe product to significantly improve subscriber opt-in conversions on my website. These subscribers became the foundation of my weekly newsletter list (a list that I’ve been sending weekly newsletters to for the past 3 years).

All of these subscribers are managed through my e-mail provider, ConvertKit, a company founded by Nathan Barry. ConvertKit helps me manage my website’s drip sequences, subscriber lists, automations, and newsletter broadcasts to make sure that I’m always engaging with my loyal readers.

Lastly, my entire online course, One Week PM, is hosted and managed by Teachable, founded by Ankur Nagpal. Teachable allows my entire course to be self-serve, where students can enroll and login to view lectures anytime they want.

Without these guys, Product Manager HQ most likely would not have existed or reached the scale that it is today. Their products enabled me to become a “creator” and for that, I am eternally grateful.

We’re trained from a young age to consume. Part of this is a result of our legacy educational system borne from the Industrial Revolution:

Mass education was the ingenious machine constructed by industrialism to produce the kind of adults it needed. The problem was inordinately complex. How to pre-adapt children for a new world – a world of repetitive indoor toil, smoke, noise, machines, crowded living conditions, collective discipline, a world in which time was to be regulated not by the cycle of sun and moon, but by the factory whistle and the clock.

The solution was an educational system that, in its very structure, simulated this new world. This system did not emerge instantly. Even today it retains throw-back elements from pre-industrial society. Yet the whole idea of assembling masses of students (raw material) to be processed by teachers (workers) in a centrally located school (factory) was a stroke of industrial genius. The whole administrative hierarchy of education, as it grew up, followed the model of industrial bureaucracy. The very organization of knowledge into permanent disciplines was grounded on industrial assumptions. Children marched from place to place and sat in assigned stations. Bells rang to announce changes of time.

The inner life of the school thus became an anticipatory mirror, a perfect introduction to industrial society. The most criticized features of education today – the regimentation, lack of individualization, the rigid systems of seating, grouping, grading and marking, the authoritarian role of the teacher – are precisely those that made mass public education so effective an instrument of adaptation for its place and time.

Source: ‘Future Shock’ by Alvin Toffler

Despite this fact, we should all aspire to break this consumption mindset.

99% of the world will be perfectly satisfied spending the rest of their life consuming, but only the bold will dare make that leap towards becoming a creator.

Any chance I get, I’ll always stand with a hand outstretched at that border, ready to catch the hand of any individual who’s willing to make the jump.

Define Your Strike Zone

In one of my early middle school English classes, I had a seat next to the teacher’s desk where he had taped a poster of hockey athlete Wayne Gretzky and the quote “You miss 100% of the shots you never take.”

If I managed to submit a quiz early, I would lay my head down sideways on my desk and stare at that poster’s quote while waiting for the recess bell to chime.

At such a young age, my brain was especially malleable and I grew to embody that quote into everything that I did. There was no such thing as a fearful moment or a lost opportunity. Everything was a shot that I needed to take and there were no regrets.

Volunteer to present our projects in front of class? My hand was up first. Everyone scared to take the first leap while cliff-diving in Hawaii? My feet took control and I’d be the first over the cliff into the water.

That quote built an insatiable and intrinsic desire to always be pushing forward. Unfortunately, this desire also meant that I often had too many toes dipped in too many projects.

As a result, a finite amount of time and focus meant that I often lacked the ability to follow-through with each new opportunity.

In hindsight, it’s easy to see how I misinterpreted that Wayne Gretzky quote. Wayne didn’t line up a thousand crappy shots and take them all because he could. He had years of practice and instinct that allowed him to optimally line up his hockey stick, rack up the courage, and take the right shots.

When it comes to investments, Warren Buffett often speaks of a taking a “Ted Williams kind of discipline.”

Ted Williams was a baseball player on the Boston Red Sox who analyzed and carved the baseball strike zone into 77 individual cells. He then created probabilistic results of successful bats for each cell based on his history of hitting in each of these strike zones.

By using his rigid method and waiting for the perfect pitches in his optimal strike zones, Ted Williams maintained a .344 batting average and was responsible for more than a fifth of his team’s runs over two decades. For context, a season batting average higher than .300 is considered to be excellent and an average higher than .400 is a nearly unachievable goal. Ted Williams even managed to hit .406 in 1941 (source).

Now that I’m a bit more self-aware of my flaws, I take more time to focus and think before proceeding to jump headfirst into each new opportunity.

Venture capital has been the perfect industry to maintain this level of discipline. While each new founder I meet is unequivocally infectious, passionate, and convincing (as they rightfully should be), I only have a limited number of shots. Now, more than ever, I need to be defining my strike zone.

The trick in investing is just to sit there and watch pitch after pitch go by and wait for the one right in your sweet spot. And if people are yelling, ‘Swing, you bum!,’ ignore them. Defining what your game is — where you’re going to have an edge — is enormously important.

-Warren Buffett

The Glorious Walks

Below is one of my favorite passages from Roald Dahl’s “Boy” about his father:

He harboured a curious theory about how to develop a sense of beauty in the minds of his children. Every time my mother became pregnant, he would wait until the last three months of her pregnancy and then he would announce to her that ‘the glorious walks’ must begin. These glorious walks consisted of him taking her to places of great beauty in the countryside and walking with her for about an hour each day so that she could absorb the splendour of the surroundings.

His theory was that if the eye of a pregnant woman was constantly observing the beauty of nature, this beauty would somehow become transmitted to the mind of the unborn baby within her womb and that baby would grow up to be a lover of beautiful things.

Call me an optimist, but I’ve always believed that these ‘glorious walks’ were a perfect parallel to undergoing any kind of experience in this world (good or bad) as they provide the necessary empathy and inspiration for bringing your ideas to life.

Great designers often started their journeys by viewing and recreating as many existing designs as possible. A common thread amongst honest designers states that “All creative work builds on what came before. Nothing is completely original.”

One of the first things I was taught as a young budding product manager was to take apps or products that I admired and deconstruct them: breaking down each business model, user flow, visual design, and piece of the technology stack.

Understanding how these great products were built from the ground up gave me even more context and reference material to draw upon when it came time to build my own products.

In venture capital, I spend most of my days observing the beauty of new companies by speaking with 8-15 startup founders per week.

Increasing my reps of meeting with each of these companies is imperative towards building my mental repertoire towards understanding what makes great teams and companies tick.

This mode of thinking has provided a specific mindset that allows me to never regret or be intimidated by any kind of human experience. And that makes life so much more enjoyable.

Formalize Your Mentor Relationships

When I was much younger, I never quite understood the advice friends gave me around formally asking people whom they respected to become their mentors.

In my mind, life wasn’t supposed to feel so transactional. I built relationships with people over time and I never felt a need to directly ask someone to be my mentor.

Asking someone to be a mentor felt like the awkward dating phase in high school where you’ve both liked each other for a long time and you’re pressured into popping the “will you be my boyfriend / girlfriend” question.

Recently, I’ve gone back to square one to question my own beliefs and I’ve come to realize what a big loss it was to never formalize these mentor relationships.

Pop the Big Question

A few months ago, I met someone in my product community whom I immediately hit if off with online, so we decided to grab some coffee given he had recently moved with his family to San Francisco.

After chatting for an hour, I came to the realization that I had a great deal of respect for him in everything he had accomplished personally and professionally.

And so, for the first time ever, when the meeting ended, I verbally asked him to be my mentor. After a week of careful thought, he agreed to my request and we kicked things off.

Prepare for the Meeting

The first thing we did was establish a regular cadence of meetings. I initially felt bad about taking too much of his time, so I threw out the option of quarterly meetings. He immediately pushed back by suggesting monthly recurring meetings and we could scale back if necessary.

I came to the first mentor meeting prepared with an agenda in my notebook. There were a couple thematic areas of my life that I couldn’t prioritize and I wanted some advice on how to proceed.

We spent the hour talking through each of these “themes,” and he asked me to rate each on a scale of 1-10 (1 = not interested in pursuing this theme at all). Based on my responses, he was able to provide some objective 3rd party opinions on how to proceed.

After helping me prioritize my areas of focus, he put me on the spot and asked me to think about my one core life goal.

His objective there was to force me to distill various goals into one overarching goal that would act as an umbrella and north star.

(side note: funnily enough, this is a common exercise I do with seed stage founders that I work with. I’ll often keep digging with questions until we get to the one core KPI they want to focus on and we’ll figure out how to maximize that KPI)

We talked about a few other topics but I wanted to give you a sense of the value that I immediately derived from that first formal mentor meeting.

Document the Learnings

After that first meeting, I immediately created a Google Doc and wrote a recap of everything we had discussed, separating my notes into:

  • Raw Notes Transcript: Data dump of everything I could remember
  • Discussion Summary: Key bullet points summarizing the conversation
  • Action Items
  • Possible Topics for the Next Meeting

Writing this document is important because it reinforces the learnings in your mind and serves as a point of reference for future meetings to show that you’re actually making progress.

To recap, I no longer believe that it’s enough to have an unspoken mentor-mentee relationship where you both meet whenever convenient and chat about whatever comes to mind.

If you want to take your mentor relationship to the next level and show visible progress, formalize your mentor relationships by doing the following:

  1. Mutually agree to a formal mentor-mentee relationship (pop the question)
  2. Establish a regular cadence of meetings (try starting with a monthly cadence)
  3. Come prepared for every meeting with an agenda or topics you’d like to discuss
  4. Document learnings in writing after every mentor meeting
  5. Act on these learnings (show your mentor that you can walk the walk)

Why I Started the Product Manager HQ Community

Many people are often curious about the backstory behind kicking off the Product Manager HQ community so I thought I’d write a quick post outlining some of the initial thought process.

My very first Associate Product Manager role was at a company called Kabam, a web / mobile gaming company that primarily worked with Hollywood IPs, helping to make games for legendary franchises like the Godfather, the Hobbit, Fast and Furious, Marvel, Star Wars, Transformers, etc…

I joined the company in it’s hyper growth phase (it scaled from 300-800 employees in the 2 years I was there) and like many first-time PMs, I was thrown into the fray with very little guidance.

The PM group hadn’t established a formal onboarding program and each PM seemed to run their games / P&L differently, so the first few months were a struggle for me to establish a baseline of whether I was “doing product management correctly.”

Shortly after I joined the company, Kabam became one of the very first massive publishers to make the crucial strategic shift away from web into mobile. As a result, many of the PMs were entering unfamiliar territory where existing web product development processes started to break down when applied to mobile (i.e. release cycles were much longer due to Apple’s stringent 1-2 week build approval process).

Since everyone was busy adapting to mobile and putting out their own fires, it was difficult for me to find a mentor within the company who would be able to dedicate time towards helping me grow into the product role.

Secondly, our product teams regularly collaborated / synced for product reviews which helped to standardize certain practices, but given this was my first product role, I was always curious how product teams at other companies might have approached solving the same problems we were facing as a company.

I chatted with a few product manager buddies at other companies and realized that I wasn’t the only one facing these problems. Other new PMs were having a hard time:

1) Finding a product mentor outside of the company

2) Finding a peer group of PMs to chat with about best practices / ideas

To solve these problems, I first turned to attending as many product events in the city as I could find. However, I quickly realized that these one-off interactions with attendees once a month weren’t enough to solidify the trust necessary to develop mentor/mentee relationships or establish a support group that I could turn to whenever I needed advice.

Additionally, I often came across time-sensitive issues at work and there wasn’t a synchronous medium that I could tap into in order to get immediate feedback.

All of this was happening around 2013, and as luck would have it, an interesting company called Slack had just pivoted into a real-time collaboration platform (the Slack we know today). I fell in love with the Slack platform as soon as I started using it, and realized that it would be an amazing medium to run a live community.

When I first kicked off the community on Slack, it was free to join and I seeded the initial 10-20 members with product manager friends. 

0-200 members:

In the early days, I would DM (direct message) every single member and start conversations to befriend them and learn about what products they were working on. Between a typeform that people had to fill out to join the community and a mini google spreadsheet CRM that I used to store information on each member, I had a nice mental map of who I should be connecting to whom.

I likened a lot of this initial community building to an experience of attending a cocktail party. Think of the times where you’ve walked into a party solo and awkwardly tried to make your way into a conversation circle – frankly, that experience sucks. Now contrast that to a cocktail party where a friend of yours knows everyone and pulls you into circles while saying “Hey everyone, have you met my friend _________?” It’s a much more accommodating experience, and you’re likely to have a better time.

If one member told me about a problem he/she was having when PM’ing an enterprise SaaS product, I would find another member working on a similar product, introduce them to each other, and ask them to both chat about their issues in public channels so that other people could learn from their conversation. To help kickoff conversations and engage lurkers, I seeded questions in public channels (i.e. “Has anyone here tried any product roadmapping tools? What were your favorite ones?”) every single day.

200-1000 members:

At around 200-400 members, I started to see more word-of-mouth growth as members started referring friends and colleagues in the industry to join the community and conversations started to organically happen daily without much input from me.

Personally welcoming every new member in the community became a bit overwhelming (especially because people joined from different time zones when I might be sleeping), so I began to use tools like Zapier and Slack integrations / bots for more sophisticated and automated onboarding messages.

To help engage the community, I also reached out to specific “power user” members who were chatting daily and asked them if they would be interested in becoming community moderators. I created a private group for these moderators, set some light guidelines, and trusted them to help engage with the community and let me know of any “bad behavior”, i.e. spammers or recruiters.

As a solopreneur who was so used to doing everything myself, establishing this moderator group was one of the most important lessons for me in terms of learning to let go / not trying to do everything myself and distributing responsibility amongst the community.

1000+ members:

At around 1000 members, I began to notice a trend where over 90% of new members joining would churn after the first few weeks (Slack provides a weekly report of which members become “inactive”). A large part of this was because joining was free, so many people joined out of curiosity and left shortly after. I suspected this trend was also happening because the community was now large enough where conversations were happening daily and it probably became quickly overwhelming for new members who had never intended to seriously engage in the first place.

To counteract this, I replaced my typeform with a new landing page / Gumroad plugin and started charging a one-time lifetime membership fee of $25 to weed out inactives and people who weren’t serious about participating in the community. After instituting the paywall, the churn trend completely reversed.

To help justify the $25 one-time fee, I made sure to include plenty of benefits such as instituting bi-monthly AMAs (ask me anything) with product leaders and working with product conferences / events to negotiate large discounts for community members. The community has since featured AMAs with well-known product people in the industry including Ken Norton (Product Partner at Google Ventures), Josh Elman (Partner at Greylock Partners), Punit Soni (Former CPO at Flipkart), Alexandra Cavoulacos (Co-Founder at The Muse), David Cancel (CEO at Drift), and Ellen Chisa (VP of Product at Lola), amongst many others.

The thing that brings me the greatest satisfaction in all of this is the value that I’ve helped to create in the product management community.

In-person meetups around the world happen organically through initial interactions in the community, and our last San Francisco meetup (which was supposed to be with a small group of PMHQ members) blew up on Facebook and brought in 200 aspiring / current PMs to fill up a local bar. Large enterprise companies such as Intuit have even onboarded their entire 200+ global PM organization into the community and continue to onboard each new cohort of PMs every year.

Over the past few years, I’ve lost count of the number of members who have landed jobs from the community. (I try to save as many screenshots of these moments as I can in a folder on my desktop labeled “Why This is Important”.)

And lastly, I’d like to think that product organizations worldwide have gained real insights into how other teams think about product and have shipped better products as a result.

Venture Capital and Product Management

Ever since entering the venture capital industry 8 months ago, I’ve been thinking about how best to cross-pollinate venture work with my previous product experience (Even going as far as to guest-speak on the #1 most listened product podcast about how Venture Capital is Product Management).

In my first post, I discussed how I first attempted to codify the qualities of a good VC. This step was important so that I could begin mapping PM skills / workflows to VC skills / workflows and look for overlapping opportunities.

At a sky-high level (reiterating: sky-high level), you can imagine product management to break down into 3 core buckets of:

Product Planning

All the user research / needs gathering / synthesis of qualitative & quantitative data that helps inform what product / features should be built.


All of the roadmap planning / sprint planning / spec writing / launch planning / cross-functional collaboration that gets the product launched.

Post-launch Iteration

The ongoing planning & execution necessary to keep successfully improving and growing the product post-launch.

If I map this to venture capital, I imagine it to look something like:

Product Planning = Sourcing

Creating deal flow through outbound sourcing (researching industries and doing cold outreach, attending events / demo days, hosting office hours at accelerators, etc…) or inbound sourcing (referrals, inbound e-mails, people pitching you at a party, etc…).

Execution = Diligence / Executing the investment

Filtering through sourced companies by undergoing deeper diligence (getting to know the founding team, deconstructing the product, digging into metrics, looking through historical financials if there are any, competitive analysis, determining customer love, etc…), negotiating terms, proving value-add to win competitive rounds, executing the investment.

Post-launch Iteration = Supporting your founders

Working with the founders to support them and help them succeed in any way possible (board meetings, strategic advice, helping them hire, finding them customers, guiding them on product strategy, thinking through growth strategies, etc…)

Tactically, here are a few random examples (these examples aren’t too structured so bear with me) of cross-pollination that I’ve thought about or tried so far:

Roadmap: I started by creating a personal roadmap outlining the VC skill-sets I wanted to improve throughout the year. I’ll need to regularly re-visit this roadmap in order to re-prioritize where I want to be focusing my time.

Venture Backlog: I’ve created a backlog of venture projects (for myself and a few members of the venture team) that I cost and prioritize so that I can actively work on top-priority projects during any rare down-time I have.

Sprints: I need to do a bit more thinking about this one. It’s easy to fantasize breaking down my workflow into sprints / sprint tasks but my weeks can be spontaneously unpredictable, especially if we’re considering an investment where the funding round is moving quickly. This leads me to believe that the traditional product sprint cycle would break far too often to be accurate or even necessary.

Specs: It’s not an exact parallel but I’ve tried to structure writing my investment memos as if I were writing product specs. There’s not as much team collaboration around memos (we’re generally expected to have filled out the majority of our memos with our own points of view) but we’re expected to be just as thorough and think through all “edge cases.”

UX: I’m always looking to improve the “user experience” for founders. I never want a founder to leave a meeting feeling like they’ve wasted time with me. I’ve been experimenting with various methods of feedback – one passive strategy was creating a Typeform that I link in my e-mail signature. Lot of clicks but no responses yet (I may shift to simply linking to this Typeform in my rejection e-mails to founders)

My e-mail signature

TBD: I’m going to keep this a living post and update accordingly as I experiment with more cross-pollination in the upcoming months

If you want some more inspiration around the importance of cross-pollinating, check out Scott Adams’ book “How to Fail at Almost Everything and Still Win Big.” For those who don’t know, Scott is the original creator of the Dilbert comics and this book is a peek into his life journey from his humble origins into the comic superstar that he is today.

It’s a great feel-good story: a seemingly average underdog overcomes potentially career-ending voice & hand health issues, works consistently on nights/weekends at his craft, and finally gets the break he needs.

More importantly, there are a few pieces of “career advice” that he sprinkles throughout the book. One particular non-traditional recommendation he gives is to forget about becoming the best at one specific thing and instead become very good (top 25%) at two or more things.

What’s the First Thing You Do When You Come Home?

A few days ago, I was enjoying coffee with a new friend I had met over the Internet when she proceeded to ask me what my hobbies were.

This question has always been tough for me to answer. I enjoy casual activities (I occasionally play guitar, sing, work out, play sports, delve into nature, etc…) and I have nothing against “hobbies,” but if I were 100% honest about it, I spend the majority of my time doing things other people might label “work.”

If I’m not focusing on venture (studying new industries, talking to founders, helping my existing portfolio companies), I’m probably looking for ways to improve Product Manager HQ or using my remaining time to learn new skills / educate myself on new topics.

I’ve often contemplated taking Jason Lemkin’s (SaaStr founder) approach of outright answering these types of questions with “I have no known hobbies.” #noshame.

One question I like to ask people instead is, “What’s the first thing you do when you get home?”

People tend to follow very standard routines / habits and the first thing they do when they get home (assuming they are working some sort of day job) oftentimes dictate how the rest of their night will go – whether that’s sitting at their desk and typing Netflix into a browser, opening a book, heading to the gym, etc…

I don’t believe that people can change their behaviors easily (there’s a reason most health / fitness apps don’t end up dramatically influencing any kind of diet or exercise behaviors) and understanding their routine actions when they come home provide a much better glimpse into what kind of person they are or aspire to be.


How the Economic Machine Works

After finishing my previous post referencing Ray Dalio’s Principles, I ended up digging around the web and came across this 30-minute gem where Ray Dalio uses extremely simple principles to explain how the economic machine works.

The video is nicely narrated & visualized – definitely worth the 30-minute watch.

Pain + Reflection = Progress

One item that’s long been on my reading bucket list is Ray Dalio’s Principles, a 3-part 100+ page living document that outlines: the importance of principles, Dalio’s most fundamental life principles, and his management principles.

Ray is probably most well known for founding Bridgewater Associates, one of the world’s largest and best-performing hedge funds, known for it’s cult-like culture.

Empathy and kindness aren’t a top priority there, says a former Bridgewater employee. The firm’s culture of absolute candor is designed to strip out emotional considerations and emphasize cold, Vulcan logic in all decision-making—the thin-skinned need not apply.

-Quoted from an NYMag piece

If you’re curious, you can read more about Ray and Bridgewater in this Fortune piece here.

A few weeks ago, I finally started digging into Principles and a few pages in, one particular section stood out almost immediately. I’ll paste it in its entirety here:

It is a fundamental law of nature that to evolve one has to push one’s limits, which is painful, in order to gain strength—whether it’s in the form of lifting weights, facing problems head-on, or in any other way. Nature gave us pain as a messaging device to tell us that we are approaching, or that we have exceeded, our limits in some way. At the same time, nature made the process of getting stronger require us to push our limits. Gaining strength is the adaptation process of the body and the mind to encountering one’s limits, which is painful. In other words, both pain and strength typically result from encountering one’s barriers. When we encounter pain, we are at an important juncture in our decision-making process.

Most people react to pain badly. They have “fight or flight” reactions to it: they either strike out at whatever brought them the pain or they try run away from it. As a result, they don’t learn to find ways around their barriers, so they encounter them over and over again and make little or no progress toward what they want.

Those who react well to pain that stands in the way of getting to their goals—those who understand what is causing it and how to deal with it so that it can be disposed of as a barrier—gain strength and satisfaction. This is because most learning comes from making mistakes, reflecting on the causes of the mistakes, and learning what to do differently in the future. Believe it or not, you are lucky to feel the pain if you approach it correctly, because it will signal that you need to find solutions and to progress. Since the only way you are going to find solutions to painful problems is by thinking deeply about them – i.e., reflecting – if you can develop a knee-jerk reaction to pain that is to reflect rather than to fight or flee, it will lead to your rapid learning/evolving.

So, please remember that:

Pain + Reflection = Progress

When I first glanced over that 3 word formula, my mind immediately raced through all of the recent painful junctures in my life. While I hope to never revisit any of those specific situations again, I can’t help but agree that those times of pain spurred some of the most pivotal changes that positively influenced my well-being.

Ironically enough, now that life has re-stabilized towards a healthier baseline, I sometimes find myself worrying that I’m not creating enough pain in my life to push through existing boundaries.

As my friend Ray and I often jokingly say to each other, “You can’t get out of bed if you’re sleeping in silk sheets.”

Tim Ferriss, one of the world’s leading self-development gurus, has previously recommended that everyone should intentionally re-create painful situations every once in awhile, whether that be intermittent fasting, or sleeping on the sidewalk outside your home for the night.

The thought process of creating these mini-scenarios is is 2-fold:

1) You’re forced to leave your comfort zones which drive you to be more resourceful and think creatively.

2) You break the cycle of hedonic adaption (the observed tendency of humans to quickly return to a relatively stable level of happiness despite major positive or negative events or life changes) and become more appreciative of your present situation. Additionally, you are less likely to feel as negatively impacted when something “bad” happens in your life.

It sounds masochistic but one thing I’d like to explore more of this year is how I can methodically create more pain in my life.

Smells like a potential side project idea…