Social Media is a Highlight Reel

I’m not much of a professional sports fan, but I found this short post-game interview video this morning and thought it was on point and worth sharing. The interview goes on to focus around the importance of embracing failures but I wanted to focus on the first 20 seconds.

Your social media timelines and newsfeeds are “highlight reels” that don’t make you feel any better nor do they help you focus on the process vs. the goals. No one likes to post about their failures, so all you tend to see are “overnight successes” without any footage of the hard work and mistakes made behind the scenes. I’ve often found myself comparing my Stage 1 to someone else’s Stage 10 and assuming that I’m doing something wrong when I haven’t even put in any hard work.

I don’t regret my decision 6 months+ ago to install a Chrome Extension that blocked my Facebook Timeline on desktop. I’m not perfect, and I occasionally check the timeline on my mobile phone when I’m in a morning commute. As an extrovert, it’s a tough feeling to feel a bit disconnected to what’s going on in your friend’s lives.

The flip side is that it’s a great feeling to catch up with individuals and genuinely chat about life updates vs. secretly already knowing everything about their lives from social media posts.

Drastically cutting down social media usage has also helped me focus for longer periods of time without distraction and achieve deeper states of workflow. Try cutting down on your usage and see how it affects your productivity and your mental health.

Continuous vs. Achievement Driven Success

In the last two weeks of every year, I enjoy sitting down to do a yearly audit and planning for the upcoming year.

In previous years, my audit + planning doc used to look something more like this:

  • Purpose
  • Lifetime Goals
    • Metrics of Success
  • 1 Year Goals
  • 90 Day Goals

As you can see, it was a bit more “goal” and “success” oriented, which is how most people tend to structure their own life planning.

The problem with this format is that periodically throughout the year, I always found myself staring at this long checklist of goals that I hadn’t achieved.

These goals started to feel like those items you put on your task list and leave for months at a time. If that’s ever happened to you, you’ve probably felt de-sensitized to a point where you don’t even want to look at your task list anymore.

Needless to say, I wasn’t feeling great. No amount of “accomplishment” ever felt like enough and I felt lacking.

This year, I altered my doc to include these sections:

  • A summary recap of how I felt about the entire year
  • Bullet points around things that went well and things that didn’t go so well.
  • A retrospective around the 1 year goals I had set for myself for that year and whether or not I accomplished them
  • An upcoming year planning section containing:
    • Purpose (usually a 1-liner vision statement)
    • Habits to Start / Continue
    • Habits to Stop
    • 1 Year Goals

I left in the 1 Year Goals section because it’s tough to quit all goals cold-turkey and I want to ease into this goal-less transition.

I also added a section around feedback (I was inspired by a really good friend of mine Tam) from friends and other people in my community (this deserves another post so I won’t elaborate too much here).

At first, I felt a little guilty.

In previous operating roles at startups, we always set impossible OKRs for ourselves so that we could always be reaching higher and accomplishing more.

Was I not thinking big enough? Was I missing out by removing all these goals?

Last week, I stumbled upon this picture while reading this amazing blog post from Patrick O’Shaughnessy and it helped to put into perspective everything that I had been feeling.


Patrick laid it out so succinctly with three words: “Growth without Goals.”

The legacy education system and social media drives us towards a necessity for achievement driven success but two things happen when we follow that method:

  1. We feel like we’re lacking all the way until we hit those success “milestones”
  2. Once we “achieve those milestones,” we realize that we’ve just lost the thing that gave us a sense of purpose

Continuous success is about growth without goals. Developing habits into a way of life.


Strive for Five


One of my favorite images that I never get tired of looking at is this pyramid of ownership. This image laid the foundation for how I think about taking ownership in my work and I often send it to others looking for career advice.

It’s fairly self-explanatory and 80% of the people I show it to experience their own lightbulb moments.

No matter what level you are in your organization, you should always be aiming for stages 4 or 5.

Depending on the organization, you may need to build trust through consistent and accurate decision-making in stage 4 before you are entrusted to follow through on the execution of your recommended solution.

Founders perpetually live in stage 5 because they have no choice – ruthlessly identify, diagnose, and solve problems or the company dies.


Solving the Right Problem

Mathematicians undergo years of education and training and oftentimes spend most of their entire lives dedicated toward solving one mathematical problem of their choosing.

These mathematical problems range widely and solutions to some of them would create mind-blowing implications to multiple fields including math, science, and technology.

An example of some of these important problems are the seven Millenium Prize problems, stated by the Clay Mathematics Institute in 2000.

Anyone who can complete a solution to these problems will be awarded a $1mm USD cash prize, and likely become a strong contender for the esteemed Fields Medal.

Only one of the problems (Poincaré conjecture) has been solved thus far. The Russian mathematician, Grigori Perelman, who solved it ironically turned down both the cash prize and the Fields Medal.

Whenever I read about these mathematicians, I think of two questions:

  1. How much time does a mathematician spend before settling upon the problem they want to dedicate their lives to working on?
  2. Once they decide, do these mathematicians feel a great sense of clarity and peace knowing that they can focus all their efforts onto one thing?

As the year comes to a close, it’s a good opportunity to ponder the relevance of these questions to your own life.

Have you spent your time this year ensuring that you’re focused on the right problem? Does working on this problem give you mental clarity and peace? If not, why not?

Happy holidays everyone.

Family Time

Earlier this year, I went to do a regular catch up with a good friend at his company office in San Francisco. We headed up to the rooftop to give each other our quarterly life updates. After awhile, our conversation slowly shifted towards how old we were growing and what life goals we were hoping to achieve.

He mentioned that he wasn’t that close with his parents and barely saw them in person anymore, but he worked hard every day so that he could eventually buy his mom a home.

As another first generation American who grew up with many cultural + communication differences from my immigrant parents (since I was born and raised in American culture + society), I sympathized with his statement.

We chatted about this some more, and discussed how it would take several years before he’d be able to purchase something like that for his mom.

After some thought, I asked him an intentionally leading question:

“In 5-10 years, when your parents are even older, do you think they’d be happy if you spent your youth working endlessly without seeing them and one day surprised them with a new house?”

He went quiet immediately and looked away from me – I could notice the discomfort in his face and we sat there in silence for a few seconds.

Too often, we assume that money and material goods can substitute for our lack of communication with family and friends.

When your parents are in their final decades of life, the last thing they need is a bigger home or a more luxurious car. Every day they grow older, material possessions mean so much less and their relationships mean so much more.

All they want is more time with you.

Intellectual Capital

With the meteoric rise of cryptocurrencies and a new generation of crypto-millionaires, I keep thinking back to this epic tweetstorm by Sizhao Yang and how relevant it is for the rest of my life.

Financial capital comes and goes but intellectual capital retains forever.

The wrong mindset is to get caught up in the hype and dream about get-rich-quick scenarios. The right mindset is to remember to continue accumulating knowledge along the way.

Accumulating knowledge and the right mental models allow you to make the smartest decisions and invest in the right areas at the right time.

Even if you missed the crypto boat this time around (unlikely as all ships continue rising in this rising tide), investing in your mind and learning from this experience will pay off dividends in the future.


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.

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.

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.


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…