After an investor’s recommendation recently, I stumbled on this question in an article in The Atlantic about the Grant Study. An incredible 80-year long longitudinal study following 268 Harvard-educated men and how they developed as adults. While most of the Grant Study men remain anonymous, some have publicly identified themselves, like Ben Bradlee and President John F. Kennedy. Simply put, it was history’s longest study on happiness. There were some fascinating discoveries in that study so far, like the six factors that acted leading indicators to healthy aging:
Physical activity,
A mature adaptive lifestyle to cope with ups and downs,
Little use of alcohol,
No smoking,
Stable marriage, and
Maintaining a normal weight.
I highly recommend reading George Vaillant’s Aging Well. If you’re short on time, Robert Waldinger’s TED talk. But I digress.
Despite always preaching to others that they should ask for help when they need it, I’m a terrible practitioner of my own advice. Sometimes I find it incredibly hard to ask for help from others. In situations I should be the expert in. In moments when I don’t think my problems are as big as others’. And in times when I don’t know what I want. While I hate to admit it, it’s often a problem attributed to my ego. And sometimes, unwittingly.
If you had to live your life over again, what problem would you have sought help for and whom would you have gone to?
The reason I love this question so much is that in asking it, we suspend our ego. It’s often easier to open up about the “[potholes] in the rearview mirror” than “[open] up about the potholes ahead” to use the words of Jeff Wald. It’s easier to answer What were you scared of as a child? than What are you scared of today?. I find it easier to:
Reflect on what I should have asked for help in.
Understand why I should have asked for help sooner in an empirical situation.
Then use those first principles to inform me when I should ask for help now.
Your mileage may very much vary. But nevertheless, over the past week, I found it to be an interesting thought exercise to go through. At the very minimum, something to journal on.
The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.
Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.
There is an incredible wealth of people in this world who self-proclaim to have insights or secrets to unlocking insights. From parents to teachers to the wise soul who lives down the street. From coaches to gurus to your friendly YouTube ad. To mentors. To investors. While there are a handful who do have incredibly insightful anecdotes, their stories should serve as reference points rather than edicts of the future. Another tool in the toolkit. No advice is unconditionally right nor unconditionally wrong. All are circumstantial.
After all, a friend once told me: All advice is autobiographical.
The same is true for anything I’ve ever written. Including this blogpost in itself.
Over the past two weeks, as a first-time mentor, I’ve had the incredible fortune of working alongside and talking to some amazing founders at Techstars LA. At the same time, I was able to observe some incredible mentors at work. And in this short span of time so far, I’ve gotten to understand something very acutely. The dichotomy between mentors and investors. For the purpose of this blogpost, I’m going to focus on startup mentors, rather than other kinds of mentors (i.e. personal mentors). Although I imagine the two cohorts of mentors are quite synonymous.
While the two categories aren’t mutually exclusive, there are differences. A great mentor can be a great investor, and vice versa. But they start from two fundamentally different mindsets.
Investors/mentors
An investor tries to fit a startup in the mold they’ve prescribed. A mentor fits themselves into the mold a startup prescribes.
An investor thinks “Will this succeed?” A mentor thinks “Assuming this will succeed, how do we get there?”
An investor starts with “Why you?” A mentor starts with “Why not you?”
An investor evaluates how your past will help you get to your future. A mentor helps you in the present to get to your future.
An investor has a fiduciary responsibility to their investors (i.e. LPs). A mentor doesn’t. Or a mentor, at least, has a temporal responsibility to their significant other. Then again, everyone does to the people close to them.
An investor will be on your tail to hold you accountable because they’ve got skin in the game. A mentor might not.
You can’t fire your investor. You can theoretically “fire” your mentor. More likely, you’re going to switch between multiple mentors over the course of your founding journey.
An investor has a variable check size-to-helpfulness ratio. Who knows if this investor will be multiplicatively more helpful with intros, advice, operational know-how than the size of their check? A mentor has theoretically an infinite CS:H ratio. Check size, zero. Helpfulness, the sky’s the limit.
It’s also much harder to find a mentor than an investor, outside of startup communities, like On Deck and Indie Hackers, and acceleration and incubation programs, like Y Combinator and Techstars. Frankly, being a mentor is effectively doing free consultations over an extended period of time. And if you’re outside of these communities, the best way to bring on mentors is to bring them on as advisors with advisor equity. I would use Founder’s Institute’s FAST as a reference point. And Tim Ferriss‘ litmus test for bringing on advisors: If you could only ask 5-10 very specific questions to this person once every quarter, would they still be worth 0.5% of your company without a vesting schedule?
In closing
As I mentioned above, being a mentor and an investor isn’t mutually exclusive. The best investors are often incredible mentors. And some of the greatest mentors end up being investors into your startup as well. Having been in the venture world for a while, I’ve definitely seen all categories on this Venn diagram. Sometimes you need more of one than the other. Sometimes you need both. It’s a fluid cycle. And for the small minority of venture-scalable startups, it’s worth having both.
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“I was a swimmer since I was very young and, you know, I never won. I never won.”
You’re probably assuming this is how the opening scene of a movie about a future world-champion swimmer begins. The beginning of the world’s most amazing underdog story. And you’re wrong. Well, not completely wrong. This isn’t a story about the world’s next biggest Olympic swimmer. Although it might be well-timed with the Tokyo Olympics around the corner. This… is a story, in my humble opinion, of one of the world’s next biggest venture capitalists. A story of a young Bangkok girl who became a VC from learning how to lose.
I’ve never been the smartest kid on the block. At least in the IQ department. So I make it my mission to hang out with folks who are smarter and more driven than I am. Jeep is no exception. I met her last month. And as if going from a World Bank economist to Intel leadership to startup advisor and investor to lecturing at UC Berkeley’s Haas School of Business was not enough, in our first conversation, she shared an incredible set of contrarian insights. So earlier this month, I had to jump into another conversation with her.
Something about going long
If you’re a long-time fan of this blog, you know one of my favorite Bezos-isms is, “If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few companies are willing to do that.”
Jeep is that same kind of superhuman.
“I started as a competitive swimmer since I was seven, and I swam so much and so hard, like three kilometers a day. It’s just a lot of practicing. I never even won a medal. And I kept doing it. And that was hard.
“Because other kids they got medals in different styles. So I learned early on in life what losing actually meant. And I think that’s very important because a lot of smart kids, they never learn how to fail early on in their life. And it’s kind of like a winner’s curse because you know, when they’re the best at everything, since they were young, throughout college , once they come out, and they realize that the world is hard, they are doing things or want to pursue a career that their parents cannot help them, they become risk averse. Meaning they don’t want to try new things.
“So I never won in [any] swimming competitions. Until I got into college. When I got into college, at the time I already quit swimming. I quit in high school. So, I didn’t swim competitively anymore since I didn’t have time to practice. I picked up other activities like piano, which I came to love. In college, one of my friends asked me, ‘Hey Jeep, why don’t you come back to the competition?’ And she knew I never won. We were in the same race at so many events. And I said, ‘I don’t know. Let me try.’ So I tried again.
“So I got back to the practice routine. Adjust my strokes a little bit. And then I won. I got gold and silver medals for a college swimming competition. And I was like, ‘This is a joke. How could I win?’
I never won ever, like for ten some years. And I joke with my friend, ‘You know why, because everybody else quit!’ They quit about the same age in high school.
I just went for it. And that was one of the moments in life that I realized that it’s all about grit. You do what you love and you don’t quit. There will be a moment that you win.”
The analogy extends further
“Failure is the mother of success.” It’s an ancient Chinese proverb that my mom used to tell me again and again growing up. Every time I “failed.” Scored low on a test. Embarrassed myself on stage for a school musical. Placed fourth, right off the podium for multiple competitions. It’s funny thinking about it in retrospect since she turned out to be the exact antithesis of a stereotypical Asian parent. And I love it!
Take tbh, an app where you send your friends anonymous compliments, as an example. It launched back in late 2017. 73 days after its launch, it went from zero to 2.5 million daily active users, which subsequently led to a $100M acquisition by Facebook. To many, tbh looked like an overnight success. But it wasn’t. Nikita Bier, co-founder of tbh, and his team spent seven years with 15 failed products before they arrived at tbh. And with each iteration, they learned and compounded their lessons from their previous failure.
Clubhouse’s Paul Davison and Rohan Seth is another example of a seemingly overnight success. From Talkshow to Highlight (acq. Pinterest), the pair went through at least nine failed apps before they arrive at Clubhouse – last reported to have passed 10 million users. And valued at $4 billion. Their lead investor, Andrew Chen at a16z, spent eight years getting to know Paul.
One of my junior swim teammates told me years ago when I was at my prime, “David, I don’t think I can beat you as you are now. But I promise you I will beat you one day, even if that means after you retire.” At the time, I dismissed it as just another snarky comment, which athletes are prone to make from time to time. But now that I’m a bit wiser than I was in high school, I find that same comment incredibly prescient. It just so happened that a few years ago, we raced each other again. Both of us had long exited the competitive arena, and he won.
In closing
Near the end of our conversation, Jeep cited something Soichiro Honda, the namesake for the Honda Motor Company, once said. “Success can be achieved only through repeated failure and introspection. In fact, success represents 1% of your work which results only from the 99% that is called failure. Many people dream of success. To me success can be achieved only through repeated failure and introspection. In fact, success represents 1% of your work which results only from the 99% that is called failure.”
She further elaborated, “For people who grew up in a society, in a culture that does not easily accept failure, I want them to know that it’s actually not a bad thing to try and hear rejection. But along the way, they have to make sure that they learn.
“It’s the same thing when I teach UC-Berkeley students. I told my brilliant graduate MBA students that there is, for me – and it’s true – there is no stupid question. If other people think your question is stupid, but at least you learn. If you learn, there’s no stupid question. Do not ask good questions, if it means you don’t learn anything.”
In a way, I’m reminded of a peculiar quote by Karl Popper, “Good tests kill flawed theories; we remain alive to guess again.” While Popper was known to be quite the contrarian thinker of his day, the same seems to hold for questions. Good questions kill flawed theories. We remain alive to learn again. After all, speaking from personal experience, I often find myself burning the midnight oil to ask the perfect question. But in the pursuit of asking the “perfect question”, I’ve forgone the adventures I would have had to arrive at the answer I thought I sought.
We learn when we fail. We learn, to one day succeed. The greatest are the greatest because they have a higher propensity to fail than the average person. As the great Winston Churchill said, “Success consists of going from failure to failure without loss of enthusiasm.”
And as Jeep said, “Winning is actually losing, but learning along the way.”
Thanks Jeep for helping with earlier draft edits!
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I’ve been this self-proclaimed “few screws loose” for a while. Rationally, what I do, it doesn’t always make sense. But in their post-mortems, my adventures often turn out to be invaluable lessons of growth. The month of March was no exception.
It all started with someone who reached out to tell me I didn’t know what I was talking about. And subsequently, that I should stop writing. It certainly wasn’t the first, but definitely the most direct one to date. I saw where he was coming from. I’d never personally taken an idea from inception to scale, much less exit. On the venture side, I’m a scout, and well that means, I don’t personally invest in many deals, if at all.
At the same time, it’s not like I didn’t expect such a comment. As a content creator, even an amateur one, I’m putting myself out there. And in doing so, I’m opening myself up to criticism. This, well, just the first of many more to come. In fact, I’ve alluded to it before. As Jeff Bezos once said, “If you can’t tolerate critics, don’t do anything new or interesting.” Now before I make myself seem smarter than I actually am by appealing to authority, I’m not. Simply, I believe their few words profoundly summarize what might take me an essay to convey.
In writing weekly content, and subsequently, doing my homework to write the best I can on any given topic, I give off the illusion that I’m smarter than I actually am. And every once in a while, I fall victim to using esoteric phrases. Like I could say the same statement above as: I give off the illusion that I have a larger repository of information than I have. But I do so because sometimes I really, really like the phrasing I come up with or come across. It’s more of a personal fulfillment than a misleading façade.
Like I’ve mentionedbefore… I write to think. An unrefined concept that through the process of writing, I come to a more robust understanding. But let’s be honest, it’s not all up and to the right. It’s a rollercoaster. I love how Packy McCormick, who authors Not Boring, described his own writing process.
After all, mine doesn’t fall too far from the apple tree. But I digress. That one message led me down a path to jump on phone calls with other folks who found my content or myself to be disagreeable. Some more perverse and antagonistic than others. Five people total. Four who had just fallen on a series of unfortunate events. Two of which just wanted to be heard. The other two seeking advice and feedback. And last who seemed to find power through berating me for 20 straight minutes. One other who has yet to respond.
Why? I’ve known for a while that I’m terrible at having tough conversations. Some of my friends might know from personal experience. A number of other founders who’ve been on the receiving end of my inability to say “No”. Especially when I first began in venture.
I thought that maybe – just maybe – if I go to the more extreme end of the spectrum, I might get better at giving others the respect and time they deserve. While I’m not sure if the five conversations have helped me mature, they made me a better listener.
When two broke down during our short call, what they needed wasn’t advice or feedback or someone to tell them everything was going to be alright. They just wanted someone to listen. Just listen. Given my personality, I was constantly tempted to respond. To give advice. And to ease the “awkward silence.” But it wasn’t awkward at all. My inability to recognize the sanctity of silence made it awkward.
For the two other founders, they sought feedback since no investor they chatted with so far gave them any constructive ones. I couldn’t promise connections nor capital. All I could promise was my own radical candor. And they were free to do with it as they saw fit. So I spent 10-15 minutes with each, listening to their pitch. No questions in between. My thoughts only chronicled on a 5×8 notepad in front of me. And only after they’d concluded, I would share my thoughts.
The last one, frankly, there was nothing I could do or say that would have changed his mind. And rather than trying to, which would only reinforce his belief, the best I could do was stay silent and occasionally smile.
I’m reminded once again of a line someone I deeply respect once told me, “The quality of communication is measured by not how much comes out of your mouth, but by how much reaches the other person’s ear.” And another, “We have two ears and one mouth; we should use them in that proportion.”
And I am still working on it. I have a long road ahead, but I’m positive if I keep the above lessons in mind, I’ll go further faster.
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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Proportionally speaking, I rarely make referrals and intros. Numerically speaking, I set up more intros than the average person. Frankly, if I made every intro that people have asked of me, I’d be out of social capital. It’s not to say I’m never willing to spend or risk my social capital. And I do so more frequently than most people might find comfortable. In fact, the baseline requirement for my job is to be able to put my neck on the line for the startups I’m recommending. The other side of the coin is that I’ve made more than a few poor calls in my career so far. That is to say, I’m not perfect.
I only set up intros if I can see a win-win scenario. A win for the person who wants to get introduced. And a win for the person they will be introduced to. The clearer I can see it, the easier the intro is to make. The less I can, the more I look for proxies of what could be one.
This largely has been my framework for introducing founders to investors, as well as potential hires, partners, and clients. Over the years, I realized that I’ve also been using the same for people who would like an intro to someone above their weight class.
Below I’ll share the 4 traits – not mutually exclusive – of what I look for in world-class founders.
I wrote an essay about the three types of mentors exactly a year ago. Peer. Tactical. Strategic.
Peer mentor – Someone who has a similar level of experience as you do in a given field.
Tactical mentor – Someone who is 2-5 years ahead in experience, and someone who can check your blind side. Because they have gone through similar situations as you are currently going through not too long ago, they can provide context as to the variables (core and confounding) involved.
Strategic mentor (which I formerly called veteran mentor) – Someone who has attained success in a particular field as you would define it. While they won’t be able to help you in the play-by-play, they can provide the bigger picture – the macroscopic view. Assessing and reassessing your long-term goals – your true north.
Rocks, pebbles, sand
Many of you might be no stranger to the rocks, pebbles, sand analogy. As the metaphor goes, if your life were a jar, you’d want to fill it with rocks first, then pebbles, then sand. If you start off filling your life with sand, you will have no more space for rocks and pebbles. Similarly, if you start filling it with pebbles, you will only have space left for sand, but not rocks. Analogized, rocks are your life and career’s most important projects and milestones. Pebbles are the smaller projects that lend itself to the whole, some of which you could do without. Sand represents the day-to-day, week-to-week ups and downs.
Rocks
Strategic mentors are most useful once a year (or at best 2-3 times/year) to see if you’re aligned with your goals. They help you set the large milestones you want to accomplish in your life.
What matters?
What doesn’t?
Pebbles
Tactical mentors, you seek after you come up with a few solutions/hypotheses that you would like to test. You don’t seek them as often, but they can help provide context to what you’re going through now, largely from their own experience having gone through it recently.
What variables am I overlooking or underestimating their effects on the outcome? Or simply put, what could go wrong?
Sand
You seek peer mentors before you come up with your solution and in problem-solving mode. These are the mentors you’re going to be spending the most time with. And most likely, the most abundant category of your mentors.
How would you attempt to resolve this dilemma? What would you do if you were in my shoes?
What are new, innovative ways I can use to tackle this problem?
While they vary in their sizes, each rock, pebble and sand is necessary to live your most fulfilling life.
In closing
Over the years, I’ve had the great fortune of having some amazing mentors and mentor figures that have shone me the proverbial light when alone, I may have struggled to find. Yet equally so, I’ve met their antithesis. Luckily very few, but nevertheless. People who don the mantle of being a mentor, but cannot tolerate your success when you surpass them. The latter I met years ago when I indiscriminately and naively sought out mentors, for the pure sake of just having “mentors”. Arguably, as a foolhardy contest of ego and pride, specifically to compensate my feelings of ineptitude.
A mentor like a friend is someone who is happier and wishes for your success than sometimes you do for yourself. Often, independent of their own escape velocity. Simply put, they invest in your success. And of course with that pretext, they are a scarcity. Even of those are willing and free enough to be mentors, given the volume of their inbound, understandably, their response rate is exceedingly low.
While that fact shouldn’t deter you from seeking mentorship, it makes me cherish the time, effort, and advice I have been fortunate enough to receive.
In the words of Tom Landry, legendary head coach of the Dallas Cowboys, “A coach is someone who tells you what you don’t want to hear, who has you see what you don’t want to see, so you can be who you have always known you could be.”
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I’ve written 102 essays on this blog in the past year, plus some change, spending an average of 1-2 hours per piece and a range from 30 minutes to 2 weeks. An average of 1,200 words per post. While not mutually exclusive, over half of which were on startup topics. One in three described the venture capital landscape. 36 (excluding #0) #unfiltered blog posts, where I share my raw, unfiltered thoughts about anything and everything. 16 on mental health. A surprising 13 on cold emails and its respective ecosystem. And my first public book review. Some didn’t age well, like The Marketplace of Startups. Some will stay evergreen.
25% of my blog posts I started writing at least 48 hours before the publish date. 1 in every 3 (-ish) of the afore-mentioned, I rewrote because I didn’t like the flow. For every 2 essays I wrote, 1 of which I had to wrestle deeply with the thought of imperfection. In effect, half of my essays were a practice to overcome my own mental stigma of “writer’s block.” Yet after over a year of writing, I realize that I’ve become prouder of my writing than when I started.
So, as the year is transitioning into the next, I thought I’d take some time to reflect on my growth 100 (+2) posts after starting this blog. Let’s call them superlatives.
Top 10 most popular
Ranked by total views per post, the 10 posts readers visit the most.
My Cold Email “Template” – My friends have asked me for years what I write in my cold emails, and now, what and how I write my cold outreaches are available for your toolkit.
10 Letters of Thanks to 10 People who Changed my Life – Every holiday season I write thank you letters to the people I deeply respect. It’s one of the best times of the year to reconnect. These are the letters I wrote in 2019. Here are also some I wrote this year for more context.
The Marketplace of Startups – While many of the remarks on this blog post are now obsolete, largely incited by the 2020 Black Swan event – COVID, the two questions at the end of the blog post are the two I still like to ask founders today.
Personal favorites
While not every one of these got the limelight I had hoped, each of these are ones I felt great pride in being able to write on.
Three Types of Mentors – I’ve always had multiple mentors in my life – all of which fell in three categories: peer, tactical, and veteran/strategic mentorship.
I had been wrestling with how vulnerable I can allow myself to be in the public space. Writing this post was frightening, but I’m glad I did. It cascaded into deeper conversations with my friends, colleagues and readers, but also inspired more blog posts after this about mental health.
I first started this blog with the intention of chronicling my own learnings in the amazing world of venture. While I couldn’t guarantee it would be helpful to every individual reading my humble meandering, I could, at least, guarantee what I write has been or continues to be instructive for me.
Within the first month it had evolved into an FAQ and a means to provide value to as many founders as I can when one day the number of people I want to help exceed my available bandwidth. Wishful thinking at the time, but a cause that inspired me forward. After the first six months, with the introduction of the #unfiltered series, I began to write to think – a way to flush out simple, unrefined ideas to more robust concepts. While I’ll forever be a work in progress, I began to make new dendrite connections that never existed before. In a way, I was and am still chronicling my own journey in hopes that it will continue to guide people beyond my immediate sphere of influence.
Thank you, each and every one of you, for accompanying me on this journey we took yesterday and the one we’ll take tomorrow. And I hope this cognitive passport will continue to serve as your cup o’ Zhou (/joe/) weekly.
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A few weeks ago, around the time I published Am I At My Best Right Now?, I started noticing more and more that my friends, colleagues, and people that I’ve met since were going through tough times. Two lost a family member. Some were laid off. Two were forced to leave this land I call home. Four broke up. Three burned out. Countless more told me they were stressed and/or depressed, and didn’t know how to escape this limbo. After I published that post, another handful of people also reached out and courageously shared the troubles they are going through now. How it’s been so hard to share with others. And yesterday, while editing this blog post, I found out that one of my high school friends had passed.
Inspiration and Frustration
During this time, I had a thought: Frustration is the absence of inspiration. There were many times in my own life when I was beating myself up because I couldn’t think of a solution. And a small percent of those times, I didn’t even bother to think of a solution since I was so engrossed in my frustration with myself.
In these unprecedented times and inspired by the conversations around me, I decided to show that we’re not alone. So, I asked people who I deeply respect and who could shed light as to what it means to be human. I asked just two questions, but they were only allowed to answer one of them:
What is the one thing that inspires you so much that it makes everything else in life much easier to bear?
What is stressing/frustrating you so much right now that it seems to invalidate everything else you’re doing?
In turn, they responded via email, text, or on a phone call. Of the 49 I asked, so far, 31 responded with their answers. 4 politely turned me down due to their busy schedules. Another one turned me down because she didn’t feel like she could offer value in her answer.
26 responded with what inspires them. 5 with what frustrates them. All of whom I know has been through adversity and back.
Admittedly, the hardest part about this study was how I was going to organize all these responses. Unlike the one about time allocation I did over a month ago, where I knew exactly how to organize the data before I even got all the responses, this one, I really didn’t know how to best illustrate the candor everyone shared. In fact, I would be doing a disservice to them, if reduced their honesty and courage to be vulnerable to mere numbers. So, in the end, below, I let everyone speak for themselves. Sometimes, simplicity is the best.
Thank you to everyone who contributed to making this blog post happen, including Brad Feld, Mars Aguirre, Shayan Mehdi, Thomas Owen, Chris Lyons, Mark Leon, Jamarr Lampart, Christen Nino De Guzman, Louis Q Tran, Sam Marelich, Dr. Kris Marsh, Quincy Huynh, DJ Welch, Jimmy Yue, and many, many more heroes who helped me and the world around us behind the curtains.
Friday last week, I jumped on a phone call with a founder who reached out to me after checking out my blog. In my deep fascination on how she found and learns from her mentors, she shed some light as to why she feels safe to ask stupid questions. The TL;DR of her answer – implicit trust, blended with mutual respect and admiration. That her mentors know that when she does ask a question, it’s out of curiosity and not willing ignorance – or naivety.
But on a wider scope, our conversation got me thinking and reflecting. How can we build psychological safety around questions that may seem dumb at first glace? And sometimes, even unwittingly, may seem foolish to the person answering. The characteristics of which, include:
A question whose answer is easily Google-able;
A question that the person answering may have heard too many times (and subsequently, may feel fatigue from answering again);
And, a question whose answer may seem like common sense. But common sense, arguably, is subjective. Take, for example, selling losses and holding gains in the stock market may be common sense to practiced public market investors, but may feel counter-intuitive to the average amateur trader.
We’re Human
But, if you’re like me, every so often, I ask a ‘dumb’ question. Or I feel the urge to ask it ’cause either I think the person I’m asking would provide a perspective I can’t find elsewhere or, simply, purely by accident. The latter of which happens, though I try not to, when I’m droning through a conversation. When my mind regresses to “How are you doing?” or the like.
To fix the latter, the simple solution is to be more cognizant and aware during conversations. For the former, I play with contextualization and exaggeration. Now, I should note that this isn’t a foolproof strategy and neither is it guaranteed to not make you look like a fool. You may still seem like one. But hopefully, if you’re still dying to know (and for some reason, you haven’t done your homework), you’re more likely to get an answer.
It was late that summer Friday evening. The sun had just crossed the horizon, changing the sky from blood orange red to a deeper indigo. Having put in 9000 yards, half of which were back-to-back sprints, we finally wrapped up our 2-hour practice, exhausted and slightly bewildered.
‘Twas our new coach’s first day on the job. We were expecting a chill practice, but this stranger made us work for it. And he did not beat around the bush. Relentless. In sum, he was the Gordon Ramsay of swimming.
Needless to say, he didn’t make the best impression on the team. And it was fair to say that some of my teammates were not his biggest fans. As they all shuffled out, and I had to wait for my parents to come pick me up from practice, I helped Coach with pulling the tarp covers over the pool.
Breaking the silence, he asks, “David, d’ya like to swim?”
“Of course,” I reflexively reply.
“Why d’ya like it?”
“It’s fun. I made friends. It helps me de-stress.”
“No.” And his next few words changed my perspective forever – both in swimming and in life. “You like to swim because you’ve won.”
Showing Gratitude
Obviously, in my prepubescent self, I took my coach’s comment for its face value. I like to swim because I’m good at it. Or at least, relatively speaking among my peers at that point in time. But as I grew older, that comment resonated with me on a different wavelength.
And a conversation with world-class hustler and founder of Fleeting (a company changing the landscape of trucking), Pierre*, last Friday reminded me exactly why. What I said then about why I liked to swim wasn’t completely wrong. I was able to achieve a moderate amount of success in the sport because my parents, coaches, teammates, and other friends supported and cheered for me. But I also forgot to thank one more for my accomplishments. The system itself.
Privilege of having access to coaches and supportive and ambitious teammates,
And, the seemingly minor technicalities,
My lane’s timers had faster reaction times compared to my competitor’s lane’s timers. For context, in regional meets, each lane would always have 3 timers each to record when you touched the wall on your finish, and they would take the median time as the final result.
My lane’s touchpad was working, but my competitor(s) may have had to rely on manual timers since their touchpad didn’t work. So, when it came down to close races and who touched the wall first, I would win.
Of course, there were moments I was a victim to said system as well. And I remember those moments far better than when I won as a result of the system.
So what?
The thing is, when everything is going my way, I often take it all for granted. One of the only times I realize and realized that there might be any flaws to the system are when I am left out. I have been and am a member of society that has profited from the systems – in swimming, in higher education, in work opportunities, just to name a few. And I’m sure there are even more I have yet to realize that I have benefited from.
The past few weeks have been a wake-up call to America, to the world, and to myself for what we have all let pass without questioning. And admittedly, it may be difficult to assess what explicit and implicit biases we have when we, in the words of Coach, are “winning”.
Diversity at the Table
So, it comes down to two fronts: internally and externally.
Internally, introspectively, let’s ask ourselves:
What have we won as a result of? And, what are we still winning in?
What have we benefited or profited from?
And just as there are winners, there exist still who have yet to win. Or win in a more consistent manner.
Externally, we need to bring into the fold those who have yet to win to help us assess what systemic flaws exist in our status quo. Frankly, it’s incredibly difficult to find our implicit biases alone. I know that I’ve been reminded multiple times in my life by those who are more cognizant in those arenas than I was and have been. And, those underrepresented and underestimated by the system can use all the help they can get.
Together, I’m confident we can find a better solution.
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost).Who knows? The possibilities are endless.
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