Tag: Entrepreneurship

Is it possible to read too much?

Deconstructing the different “types” of reading


The “firstest” of all first world problems is being anxious about having too much to read. The most audacious humblebrag has got to be: My voracious curiosity is sooooo stressful. (And it’s not lost upon me that there’s traces — or gobs — of this in all things Rad.) This tragic affliction is exponentially exacerbated by the digitization of the universe. If you think your Instapaper or podcast queue is unmanageable today, just wait until you have unread VR messages to respond to.

If I just read ‘one more thing’

But this feeling goes away, right? One more promotion, one exit, once I hit the number. Personally, I pine for the days when I could go to bed content without being stressed about the content I didn’t read.

Thankfully I’m not alone — a stack of unread Economists can send others into a existential crisis. I recently interviewed Scott Norton on the Rad Awakenings podcast. Scott’s a bicycle-riding Millennial with a dope mustache, who co-founded a ketchup company and sold it to Unilever eight years later. He’ll never say it, so I will — he crushed it. Yet his master is a pile of Economists. And it robs his wife and son of his most precious gift to them: his presence.

Your nemesis: a stack of economists

During our conversation, we walked through the triggering elements of this venerable publication. For starters, the Economist is full of really smart people doing really smart people stuff. So you can learn about this stuff. Then, if you’re a “connector,” (i.e. good networker) there’s a chance you could help these entrepreneurs. And with some capital, you may be able to invest. And when it’s said and done (under the hefty assumption that they succeed) you’re able to say “Oh wow, I had a hand in that.” That sounds pretty innocuous, but it felt like there was more behind this. And indeed there was. Scott adds:

I don’t fear death literally, but I do exhibit the symptoms of someone who fears death. I want to create babies — versions of myself that live beyond me. Legacy.

Should reading be blissful?

The irony that an unread stack of Economists somehow prompts an existential meltdown made us both chuckle. Yet I kept noticing versions of this conversation amongst really successful individuals. Patrick Collison, the co-founder of the unicorn Stripe discussed his stressful relationship with reading on Farnam Street (emphasis mine)::

With reading, I just feel stressed out by [the fact that so many things feel] important, [they’re] obviously important, and I don’t know it. And so, shit, I better get to work. When I’m reading, I’m not in this blissful place. I enjoy it perfectly fine, but I think there are extremely important things that I really should know and I don’t, and that feels problematic.

You could extend the reading anxiety to podcasts and YouTube videos. I’ve long shared my former addiction to chipmunk setting (aka 2.5x speed). Here’s a Twitter exchange I had with Lux Capital VC Josh Wolfe (who IMHO is one of the most thoughtful people on Twitter):


I could totally relate to Josh’s info anxiety and question if it’s something I’d ever be able to be at peace with. Here’s Josh’s candid response:


Where does this urge come from?

I miss the days when the most risqué part of reading was hiding under the covers immersed in a fantasy book with a flashlight. How did this activity morph into this competition of consuming and synthesizing all of the world’s ideas? It could be that globalization has raised the collective stakes for knowledge workers. I can’t speak for the others in this post, but for me it’s more — a bizarre cocktail of insecurity around identity, achievement and success.

It’s important to distinguish between different types of reading. Reading for information. Reading for leisure. (Reading for virtue signaling.) Ideally the intersection between the first two is large. Presumably we bounce between the two spheres based on our life’s circumstances and aspirations.

Should your reading strategy be adaptable?

And for me, every couple months these ratios get thrown out of whack. In fact, I had one of those moments two months ago right after I shared my notetaking process and Eugene Wei’s approach to rotating chapters on his Kindle. Immediately after, I went on a tear — I think I read four books in two weeks, meticulously annotating them digitally. Many of the ideas from those books percolated into these posts. But here’s the catch, something triggered this compulsive behavior. I can’t specifically pinpoint it, but it might have been a dip in subscribers or a tepid response to something I wrote. Because it was motivated by these subconscious forces I flamed out spectacularly. In fact, I’m still feeling this hangover — I haven’t read a book in months.

So next time you pick up that book. Ask yourself: why this book? Look around you to see if someone you care about is clamoring for your presence. And remember that reading can be a blissful experience.

Hi, I'm Khe Hy and this is from RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and investors by subscribing here. We cover productivity, learning, and self-exploration and all our stories are at Rad.Family.

RadReads n°169

This week: How to pick a career that actually fits, being vigilant against hedonic adaptation, what does it mean to retire, Jeff and Bezos’ leadership lessons


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Navigating fatherhood and entrepreneurship

58 mins |Rad Awakenings podcast | iTunes| Google Play

Adam Schwartz is an entrepreneur playing by a different set of rules. He and his partner co-founded TeePublic(an e-commerce platform for independent creators), a high growth business that can hang with deep pocketed, VC-backed startups. This has implications for control, profitability, urgency, and recruiting. But does this mean that Adam can carve new boundaries between work and life? Has he created a lifestyle business? The conversation then turns to him becoming a new dad the anxieties surrounding how this addition will impact his fully optimized life.


How to pick a career (that actually fits you)

60 mins from WaitButWhy

Another Tim Urban gem, rich with career frameworks. There’s the Yearning Octopus(i.e. trade-offs between personal, lifestyle, moral, social, and pragmatic desires), separating subconscious forces(i.e. the “basement of our house”), a prioritization framework(non-negotiables and things to resist), and remembering that traditional careers are a) changing and b) just one of the many “career board games”we can play. Tim’s a blogging idol and you’ll see his influence in my takes on identity, status anxiety, persistence, uncomfortable introspection(my take on the “basement”), paradox of choice, financial pragmatism, and changing career paths.


Racism’s punishing reach

30 minute podcast The Daily (NYTimes)

It’s impossible not to be appalled by the arrest of two black men waiting for a friend at a Philadelphia Starbucks. Seeing this is a personal reminder of my straight Asian male privilegeand the slew of injustices I’ll never encounter. This podcast discusses a 30 year study challenging the notion that racial inequality can be eliminated by reducing economic inequality. To reinforce the point, watch this visualizationtracking the lives of “black and white boys who grew up in families with the same income, similar family structures, education levels and levels of wealth.” For more, read Republican senator Tim Scott’s perspective on raceand the rite-of-passage conversation black men (irrespective of socio-economic standing) have with their sons about how to act when you’re pulled over.


Hacking hedonic adapation

5 mins from MrMoneyMoustache via @womtang

Buying stuff feels good. But because of the mean-reverting nature of our “baseline happiness,” it can be pretty short-lived. Then we adapt, and lifestyle creepkicks in. Are there purchases worth considering? The hacks at the bottom of the article are truly provoking and I can’t wait to try them (especially the habit trigger, piecemeal, and delay tactics). And don’t miss all our money and finance posts.


Jeff Bezos’ annual Amazon shareholder letter

10 min read from SEC filings

Jeff Bezos’ annual missive has become a must-read on leadership. This time he tackles customers’ non-static expectations and the impact on high standards (using “the perfect handstand” as a metaphor). Are high standards intrinsic or learned? Domain-specific or universal? Regardless, once you’ve set those standards, they become an invisible competitive advantage for recruiting and retention. For more Bezos, listen to Eugene Weidiscuss his time there in the late 90s.

Below the fold

BEST OF THE REST

FROM THE #RADFAM

LAST WEEK’S MOST READ

RADJOBS

Some rad mission-driven rolesthis week with Parity Partners (driving gender parity ✊) and Ghost (open-source journalism), as well as an baller 🏀 position at Wired. If you’re looking to have your dream job delivered directly to your 📥, sign up here!

A Simple Formula to Explain Happiness

Beware the “reality distortion field”


There’s an ancient samurai tradition that is meant to develop resilience, improve mental fortitude, and enhance your killer instinct. It’s called the misogi. By deliberately leaving your comfort zone, you can stretch limits of possibility and ultimately re-wire the pathways in your brain. I heard about this banal idea through an unlikely source — the mop-haired and boyish Kyle Korver of the NBA Cleveland Cavaliers. Each year, Korver and his crew of physical misfits dream up a challenge for themselves: schleping large rocks underwater for four straight hours or stand-up paddleboarding (Korver’s first time, mind you) for 25 miles in open water. So I texted a few of my homies and we came up with our own misogi: 1,000 burpees over a 24 hour period.

And we completed the challenge, albeit with numerous dad-like injuries and to the bewilderment of both our wives and kids. But as ambitious strivers, always looking for a new challenge — a streeeeeeeetch goal — the misogi felt like a strange badge of honor and validation that we had the ability to bend reality to our wills.

All about “stretch goals”

I begin each morning by going through my Omnifocus to-do list and to come up with the day’s mini-misogi. I pick 10 tasks (both big and small), and without fail mange to under-estimate how long each task will take, over-estimate my ability to focus, and somehow forget how many one-off requests I’ll encounter. As the day winds down, I return to the list only to find a three of them checked off. I fight the urge to beat myself up, yet bring that residual disappointment back to my wife and kids. I then mentally count down the minutes until everyone goes to bed, so that I can hop back on the laptop to get the dopamine hit of one more checked off task (and that wonderful swoosh sound). #MisogiFail. Every. Damn. Day.

Can you really bend reality to your will?

Wait But Why blogger Tim Urban introduced me to formula to help explain this pernicious cycle. It’s really simple:

HAPPINESS = REALITY — EXPECTATIONS

So each day, my expectations (10 units) face off with my reality (3 units) resulting in negative 7 units of happiness. Forthcoming podcast guest and psychology professor Molly Crockett described her own productivity system, one influenced by her own research on the brain’s ability to form habits.

Each morning, Molly takes a fresh sheet of paper and divides it into two columns: Hard and Easy. She then picks two tasks, one in each category. TWO!!!! She completes both, plus an additional few more. Here’s Molly’s math: reality (4) minus exceptions (2), equals positive 2 units of happiness. (To my math geeks, please don’t try to unitize Molly and my respective productivity to see who’s net-positive. It won’t work, I tried!)

I then spoke to blogger and podcaster Sarah Peck who discussed how this lens could have been applied to her own dating experience. Years ago, Sarah had just broken off an engagement and started online dating. She was struggling to meet Mr. Right when a friend suggested that she list the ten attributes she was looking in a future mate. Once she did that, the friend had her pick three. Now, I’ve never met Mr. Sarah Peck, but for argument’s sake (and no shade thrown) let’s say he had five of these attributes. Here’s Sarah’s math: reality (5) minus exceptions (2), equals positive 3 units of happiness.

What about BHAGs?

Now I’m expecting some blowback from you guys. This is a community of doers and strivers — we don’t set the bar artificially low just so we can leap over it. And I’m with you fam, I’m all for the proverbial BHAG. But I think the goals require some deep introspection (in fact, this is why I prefer systems). Take my Omnifocus example: If I’m constantly falling short by negative seven, it doesn’t mean that I’m not ambitious. It just means I’m delusional about my abilities (which actually detracts from my ambition). And the longer term-effect may be envy and unshakeable feelings of inadequacy.

I’m a numbers guy and so I’m not done with Urban’s formula. I’m going to propose two additions:

HAPPINESS = REALITY — EXPECTATIONS*(YOURS + OTHERS’)

RadReaders are hard enough on themselves, we don’t need to saddle ourselves with the added burden of our peers or societal expectations. Here’s one expectation that’ll make this math pretty clear: the two month’s salary expectation. And here’s the final adjustment:

HAPPINESS = REALITY*(YOU CAN CONTROL — YOU CAN’T) — EXPECTATIONS*(YOURS + OTHERS’)

Trust the process

For the longest time, I over-indexed on things I could control. But this addition to the formula helps separate the process from the outcome. Public speaking (an activity more feared than death itself!) is a perfect example where worry and anxiety (i.e. things you can’t control) exceed your preparation (which you can control). Everyone’s experienced the ensuing mental agitation. Once again, this doesn’t mean abandoning your resolve to deliver a banger of a presentation, instead we can borrow from one of our great teachers Frank Ostaseski: Have a plan, hold it lightly.

So the next time you begin to embark on one of your daily misogis, try this. Take a deep breath. Explore your reality and your expectations. And if you’re still lost, a simple spreadsheet can reorient you back to your True North.

Hi, I'm Khe Hy and this is from RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and investors by subscribing here. We cover productivity, creativity, and how to get out of our own way. Read more at Rad.Family.

What can a rap name generator teach you about entrepreneurship

Just start


I was bored the other day and played with a rap name generator. You answer a few questions and then it spits out a bunch of rap personas. Khedona, a likely tribute to the Wu Tang Clan. Urkel Urkel, as the geek chic has also found a home in hip hop. And my favorite, Big Corky, after my first pet — a guinea pig. But this was more than a silly internet distraction, I was borrowing a tactic from real hip hop stars. Long before they racked up Grammies and platinum awards, both Austin Post and Donald Glover used the same generators for their own namesakes — Childish Gambino and Post Malone. Why on earth would a musician relinquish their namesake — their entire brand and persona — to a janky algorithm on the Internet? My theory: they know how to start.

I then made up a scenario in which Donald Glover gathers a group of consultant friends to help him come up with his rap name. They might use focus groups or conduct an analysis of how rap names have evolved over history. Maybe put their findings in a pretty little deck. As this fictitious story pans out, Glover pulls out his iPhone, pushes a button, and boom: “Childish Gambino. Now let’s start making some fucking music.”

Starting is hard

Ideas feel so crisp and doable when they’re in your head. But as the translation takes place onto paper and into action, it’s not nearly as fun. In The War of Art author Steven Pressfield calls this the Creative Resistance, “the force that will stop an individual’s creative activity through any means necessary, whether it be rationalizing, inspiring fear and anxiety, emphasizing other distractions that require attention, and raising the voice of an inner critic.”

If only I had the right tools

We avoid starting by requiring the fanciest tools. Boy, have I fallen for this one in my life. Running a marathon? Buys the most expensive shoes. Want to write more? Gets notebooks and pens shipped from Japan. Want to be more productive? Downloads five new iOS apps. The need for tools is part of the Resistance. In fact, creativity usually benefits from the constraints of having inferior tools:


Let’s go back to hip hop and talk Fruity Loops. Nope, that’s not another automatically generated rap name, but a $100 piece of software used to create beats. Here’s Metro Boomin (of Future, Kanye, Migos, Gucci Mane fame):

In seventh grade I was in the band for a second playing bass guitar. I wanted to rap, but I needed beats. I couldn’t buy any so I just made my own. On Christmas when I was 13, my mom got me my first laptop. I downloaded it FruityLoops, cause I had heard about it, and started messing around. Shit just blew from there. I still use FruityLoops today.

And Maaly Raw (who produces Lil Uzi Vert):

A lot of producers, they got to have all this crazy equipment. If your talent’s there, all you really need is some speakers and FruityLoops. Another thing, I didn’t even have Beats headphones. I was using my Apple earphones, the ones that come with the phone. Of course, now, I got some Beats. (…) As far as equipment, that’s all I have.

The illusion of learning over doing

Another way to not start is to favor learning over doing. The Internet makes it so deliciously tempting to bathe in its free and abundant resources — in the form of explainers, blog posts and YouTube videos. (And when you’re done with those, throw in a few Kindle books.) But blogger Can Duruk warns:

It really is another form of procrastination, if not a more dangerous one in my opinion, than randomly starting to play a video game. The fact that you can fool yourself, for the most part, into thinking that you have done something really valuable with your time is really dangerous.

But the biggest obstacle to starting is caring about what others think. To go Sapiens on y’all, we are wired to seek acceptance from our group — if they reject us, we’d wither away alone on the cold tundra. Yet creativity is an act of rebellion. The first (and second, and third) thing you create — will suck.

This week marked the five year anniversary of Ben Thompson’s Stratechery. Thompson’s blog and newsletter (and business model) have been a huge source of inspiration for these pages. For the unfamiliar, he’s one of the most prominent analysts covering FANG and the business of the internet. He’s the perfect example of the unbundled career and its impact on credentialing and distribution models. Thompson shared the importance of starting with this nostalgic tweet:


Today, the internet lore has Thompson at 10,000 paying subscribers (vs 2,000 in 2015). In five years, he’s written 308 Weekly Articles and 659 Daily Updates (and recorded 159 podcasts.) How’s that for a start?

So here’s my attempt at a Childish Gambino moment. I want to make more videos — I love the challenge of visual storytelling and truly believe it to be yet another way to interact with the RadReads community. But you need tools? Nope, iPhone and iMovie. But only 12 people will watch it? That’s ok, it’s more then Ben Thompson had. But the copy and editing is so crude? Just stop talking and start. So here’s my start (an improvement from this cringeworthy 2016 video and this January magic hands video):

I showed the video to my wife and she quickly pointed out the elf with the noose around his neck (in the top right) and implored me to rerecord it. Nope, I told her I would not succumb to any Resistance. And in my Big Corky voice I said “Just trust me baby, we got this.”

Hi, I'm Khe Hy and this is from RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and investors by subscribing here. We cover productivity, creativity, and how to get out of our own way. Read more at Rad.Family.

Don’t confuse options with safety nets

Options only work if you take risk


In 2007, as a newly minted Vice President at Blackrock I bought a “junior 1 BR” (aka studio) in the East Village. A friend, in a similar situation bought his first place too in Williamsburg. It was a dizzying time in New York. The finance and hedge fund industries were booming and few knew about the lurking crisis. We were two single guys who had worked hard and saved diligently; easily seduced by flashy brokers, with their floor plans and architects’ renderings of these unbuilt condos. And “all” you needed to reserve your spot was a 10% down payment.

Not long after cutting the brokers these sizable checks, Bear Stearns and Lehman went under. Markets tanked, people got laid off in droves. My friend and I survived this and anxiously wondered what this would mean for our apartments. They were experiencing their own construction delays and finally, two years after we had put down the deposits, the apartments were ready. It was time to close and lock in sizable mortgages (90%) and monthly payments. But, we each had the option to close. I chose to close. And he chose to walk.

An option vs. an obligation

Options are powerful financial instruments that can be used to take or mitigate risk. If you buy an option you make a payment (or series of payments) for the right (but not the obligation) to buy something at a fixed price, at a later date. In our apartment example, the deposit was an option (albeit an expensive one). Two years after this option was acquired, the world changed. The apartments had definitely declined by more than 10% in value. More importantly our job prospects and earnings potential had dramatically changed and our diverging decisions represented differing views on risk. (TLDR, I sold my apartment six years later at a wash, net of fees. Eleven years later, we both should’ve held on.)

Options are everywhere

Options aren’t always so mathematically rigid, in fact whether you’re a hedge funder or high schooler, you’re constantly making decisions about options in your daily life. The premium payment often isn’t financial — it can be time, access to your relationships, opportunity costs, or cognitive burden. For example, my double major in CS and Econ (payment: time, payout: job opportunities in multiple industries); buying life insurance (payment: annual premiums, payout: a large lump sum, should the unthinkable happen); taking a networking meeting with an important person who is an a-hole (payment: time, payout: the possibility that the person could help in the future); receiving advisor shares in a startup (payment: time, payout: upside, should the company sell).

The most clichéd example of optionality can typically be found in the 20-something Wall Street male, obsessed with “keeping his options open” when it comes to dating and marriage. I never dated in the Tinder age (thankfully or regrettably, I wistfully ask myself) but I confess that in my twenties, I knew that the right combination of text messages, date nights, and well-timed compliments were a useful arsenal in simultaneously dating multiple women in New York’s dating “gray zone.”

Low cost options — a manna from the heavens?

People in finance love collecting options, especially low-cost options. Intuitively, this makes sense. As Harvard Business School Professor Mihir Desai explains in The Wisdom of Finance: (emphasis mine)

I’ve lost count of the number of students who, when describing their career goals, talk about their desire to “maximize optionality.” (…) Options have a “Heads I win, tails I don’t lose” character — what those in finance lovingly describe as a “nonlinear payoff structure.” When you hold an option and the world moves with you, you enjoy the benefits; when the world moves against you, you are shielded from the bad outcome since you are not obligated to do anything. Optionality is the state of enjoying possibilities without being on the hook to do anything. (Read more on optionality)

Don’t forget, options aren’t free

Optionality is one of those tenuous instances where financial optimization falls short when applied to the messy complexities of our daily lives. For starters, we underestimate the cost — especially the non-financial cost. Returning to the example above, the advisor share work is never just “a couple hours a month.” Requests arise such as reviewing decks, helping interview a candidate, attending an event — not to mention the friction in setting up all those communications and the opportunity costs (such as hobbies, spending time with family, exercise — or god forbid, sleep!). And on the dating side, I can’t tell you how many of my single male friends are burnt out (like literally, physically exhausted) and financially depleted from the never-ending Tinder, Bumble, and Hinge dates.

Options can be stressful

Next there’s the paradox of choice. The great thing about options is that you don’t need to commit. The possibilities are endless. But too much choice is also stressful. In his critique of higher education Excellent Sheep, former Yale professor William Deresiewicz describes how students at elite universities “can be anything in the world, so they try to delay for as long as possible the moment when they have to become just one thing in particular. Possibility, paradoxically, becomes limitation.” One of his students adds:

“My friends and I didn’t run sprinting down a thousand career paths, bound for all corners of the globe,” he wrote. “Instead, we moved cautiously, in groups, plodding down a few well-worn trails so as to ensure that two or four years down the road, we could be stem cells again, still undifferentiated, still brimming with potential.”

Options require risk taking

But the biggest blind spot in the optionality mindset actually is directly related to the math of options. Options increase in value when there is volatility or risk (Finance geeks: I know they’re not the same, but bear with me). For example, let’s say you bought a fancy car and the requisite insurance. You may be apprehensive to take it around town — it could get keyed, dinged in the lot, or even worse, there’s always the possibility of an accident. But you wouldn’t consider leaving the car in the garage, where it never risked a single blemish. Driving the car comes with risk. It’s an active risk decision that is mitigated by the option (i.e. the insurance).

Let’s extrapolate this back to careers. Desai adds:

Creating optionality can backfire in surprising ways. Instead of enabling young people to take on risks and make choices, acquiring options becomes habitual. You can never create enough option value — and the longer you spend acquiring options, the harder it is to stop. The Yale undergraduate goes to work at McKinsey for two years, then comes to Harvard Business School, then graduates and goes to work Goldman Sachs and leaves after several years to work at Blackstone. Optionality abounds! This individual has merely acquired stamps of approval and has acquired safety net upon safety net. These safety nets don’t end up enabling big risk-taking — individuals just become habitual acquirers of safety nets. The tool that was supposed to lead to more risk-taking ends up preventing it. (Read more on optionality)

Why do we become habitual acquirers of safety nets? What prevents people from taking risk? Fear. Fear of commitment. Of social critique. Of failure. Deresiewicz adds that it starts with the high expectations that are placed on students:

The prospect of not being successful terrifies [students], disorients them, defeats them. They have been haunted their whole lives by a fear of failure — often, in the first instance, by their parents’ fear of failure. The cost of falling short, even temporarily, becomes not merely practical, but existential. The result is a violent aversion to risk. You have no margin for error, so you avoid the possibility that you will ever make an error.

Becoming an entrepreneur comes with risk. So does getting married. No one is advocating for either of these, nor willy-nilly risk taking. Risk taking requires a self-awareness around the true costs and outcomes, sprinkled wth a modicum of confidence and faith. Options play a key role in risk taking, and when used correctly the returns can be spectacular.

Hi, I'm Khe Hy and this is from RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and investors by subscribing here. We cover productivity, creativity, and how to get out of our own way. Read more at Rad.Family.

Why are you so afraid of being broke?

Failure doesn’t equal Flop Houses


I’m really excited about a new investment opportunity. I want to build a portfolio of poorhouses, flop houses, and cardboard boxes. Why? It seems to be where many successful professionals think they’ll ultimately end up living. And plus, in the investing spirit of Peter Lynch, I’d be “buying something I understand.”

Just this week, three signs confirming this investment thesis came my way. First, in the book The Soul of Shame where psychiatrist Curt Thompson described a successful marketing executive bracing for the day when his business would collapse and “he and his family would one day end up living in a box under a bridge.” Then there’s ABC news anchor Dan Harris who worried that his receding hairline would impact his camera-facing career. In the book 10% Happier, he described his irrational tendency to “immediately project forward to an unpleasant future (e.g. Balding → Unemployment → Flophouse in Duluth).” And then one of my teachers, Andrew Taggart sent me the following note:

“I, meanwhile, am beginning to count on my fingers the number of high-powered executives who have mentioned to me their fear of finding themselves in ‘the poorhouse’ someday. (I may have to rent some more fingers.)”

The caveman must survive

What the heck is going on? I guess there’s the evolutionary (pop) theory that these are our caveman instincts on display enforcing vigilance in anticipation of the cataclysmic event that knocks us off of our professional pedestals. (But recall that fear inhibits the right side of our brain and hence our creativity and problem solving skills.) Or maybe it’s the way we confuse financial security and meaning? Or that our stress is a perverted relationship with time?

Earlier this year, I was in an entrepreneurial rut. And I confided in Andrew that this was leaking into my personal life. Despite pouring my heart and soul into the RadReads community — writing, podcasts, and events — on a week-over-week basis the subscriber base was actually shrinking. Fo real? Then my caveman instincts kicked in: I started researching growth hacks, creating new landing pages, and being more aggressive in my marketing. After all, a decline in email subscribers must be the canary in the flop house. Andrew reminded me of my preoccupation with “the cult of scale” and one of its gnarly side effects: the idea that “a line trending downward carries ideas of failure, degradation, bleeding, and decay.”

We amplify losses, dismiss wins

There’s a financial concept called negative convexity. In layman’s terms it describes a security that tends to lose more than it can gain. So tails, I lose; heads I win, but not as much. You can see this at play with these flop house predictions. Yes, The losses are amplified, but we’re also too quick to dismiss the wins.

Professor, author, polymath (and longtime RadReader) Adam Grant spoke about this phenomenon on the Farnam Street podcast:

”I don’t think we’re very good at mental time travel. When something goes wrong, we amplify it and catastrophize it — it starts to feel like it’s “the worst thing that ever happened to me” yet in rare cases it is. That’s stiff competition. For something to be the worst thing that ever happened to you of all the bad things that have ever occurred to you in your life — this has to be the worst. The odds are, it’s not the worst thing.”

The imperial tendency of the mind

Dan Harris calls this Prapanca, a Buddhist term he describes as “the imperialistic tendency of the mind.” I’ve struggled with this catastrophization and want to share one of my tools. Every time one of these events happen, I write them down in Evernote. It’s funny to look back at them, because as Adam says “the odds are, it’s not the worst thing.” In fact, oftentimes its not even a thing. Here’s a screenshot of my Prapanca Journal:


I pasted the doc “as is” to avoid any narrative-building confirmation bias (check the “updated” date and I hid one thing for privacy). Yes, with two young kids in the city, neighbors can be a big source of anxiety and you’ll recall the car rental incident (which had a 100% positive resolution). I urge you to try this — you’ll quickly realize how thoughts think themselves and the flop house probabilities will plummet.

And just like convexity, we should remember this in the opposite direction — the wins, both big and small must be savored. When good things happen to us, we’re quick to dismiss them, move on, and reset our baseline expectations. Here, Adam proposes that in these milestone moments he rewinds the clock, asking himself “If my five years ago self knew that this was going to happen, how excited would I be?” Because after all, “moments of joy are really important and part of what makes life worth living and what we have to look forward to. Being human is being able to enjoy life.”

Hi, I'm Khe Hy and this is from RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and investors by subscribing here. We cover productivity, creativity, and how to get out of our own way. Read more at Rad.Family.

RadReads n°160

This week: You don’t retain what you Binge Read, Hiring ‘Insecure Overachievers,’ Does Convenience beget Conformity [SUBSCRIBE]


Good morning –

Greetings from the Bahamas, where we’re having our first kids-centric vacation and where I got to meet Shane Parrish!

Looking for a coach? Check out our new curated list of Rad Coaches. And don’t miss our free webinar on How to Start Blogging on March 9th.


You are what you repeatedly do

1 hour | Rad Awakenings | iTunes | Google Play

My happy place is interviewing a high energy meditator who curses like a sailor. Jeff Warren is a meditation teacher and the co-author of Meditation for Fidgety Skeptics with Dan Harris. The two of us bounce of the walls in this fun conversation. We talk a lot about mental health and how, yet’s its possible for a longtime meditator to really struggle from ADD. We talk stories, à la Sapiens with real examples about how stories can shape our realities. And Jeff answers the long time RadReader pushback about why one should welcome inquiring into your fears, with one of the best meditation metaphors ever.


The Tyranny of Convenience

7 mins | The New York Times

Convenience is a good thing, n’est-ce pas? After all, our lives are unquestionably getting more convenient — but with it can come conformity. Is there a benefit to having to strive and suffer to get certain things? Tim Wu, a total polymath (listen here) argues that convenience is “all destination, no journey” (see last week’s postscript) and “threatens to erase the sort of struggles and challenges that help give meaning to life.”


If You’re So Successful Why Are You Still Working 70 Hours a Week?

6 mins | Harvard Business Review

Did you know that firms explicitly target and recruit “insecure overachievers?” (my life all of a sudden makes a lot more sense 😜). This bunch is driven “by a profound sense of their inadequacy, typically stemming from childhood.” (Ahem, cuddle puddles!) Paradoxically, they don’t blame their employers, because impostor syndrome kicks in, and somehow everyone around you appears to be coping better than you are. This post is brutally incisive.


Why We Forget Most of the Books We Read

9 Minutes | The Atlantic

There’s a distinction between reading for knowledge and for information. Thanks to digitization, “recall memory” (the kind one uses to crush Trivia night) is no longer important. Yet, we continue to binge on information, be it Netflix series or even the written word, with very little of chance of the information actually “sticking” — and becoming knowledge.


What is the mindful response to a school shooting?

4 mins | Kottke

Like everyone else, I’m sickened and saddened the Parkland shooting (and maybe there’s a glimmer of hope that social media helps effectuate some sort of change). This article is about mindfulness, from Robert Wright’s newsletter about resistance. Oftentimes people confuse mindfulness with acceptance or resignation. This couldn’t be further from the truth — it’s the practice of cultivating a “clear, alert, acutely aware mind.” I found this article highly practical in response to both mass shootings and the clarity required in activism. (I’ve also written about Wright’s book Why Buddhism is True.)

https://upscri.be/277e81/

Below the Fold

ICYMI
🎙 Abby Raphel founder of the Redwoods Initiative on knowing your shadow: Abby’s circuitous journey to educating the uber-wealthy about, well, wealth.

🖥 The cost of being the best (4 mins, The Mission): Last week’s postscript on winning 5 or 1 Super Bowls. No, this isn’t a takedown of excellence.

💼 RadJobs: If you haven’t polished up your resume this year, now’s the time. Roles at Trax, Waymo, X (Google), Luke’s Lobster, and a sweet family office gig at Raga Partners. If you’re looking to have your dream job delivered directly to your 📤, sign up here!

LAST WEEK’S MOST READ
💔 The Marriage Decision: Everything Forever or Nothing Ever Again (27 mins, Wait But Why): What’s the best heuristic to use for the biggest decision of your life?

The cost of being the best

Would you rather win 1 or 5 Super Bowls?


Tom Brady is the G.O.A.T. Yes, despite falling one drive short of their sixth Super Bowl, it’s hard to throw shade at Brady and the Patriots. Who wouldn’t want to be the handsome underdog turned future hall-of-famer, a savage competitor with ice in his veins, performing at his peak at age 40, and, let’s not forget, Gisele’s arm candy. (But what’s up with not eating strawberries?) You’d have to be nuts to not to want aspire to be Brady or the Patriots.

How can you hate on Tom Brady, the GOAT?

Enter the shade, delivered via defensive end Lane Johnson from the Super Bowl champion Eagles. He criticized the Patriots’ “culture of fear” adding: “You only get to do this job one time, so let’s have fun while we’re doing it. Not to be reckless, but I’d much rather have fun and win a Super Bowl than be miserable and win five Super Bowls.”

Most of us would call BS on that statement. After all, five is greater than one. Excellence at all costs is what we strive for. And fun? Save the strawberry daiquiris for retirement, once the trophy case is complete. These are just the words of a newly victorious and braggart lineman — not worth deeper consideration, right?

Lifestyle versus venture-backed businesses

But we often face a variant of this dilemma in our everyday lives. Do we take the job with more pay and put up with brutal hours? Do we start a lifestyle business or venture-backed start up? How do we reconcile delayed gratification versus living in the present?

When I left the corporate world, I was very fixated on starting a high growth, venture-backed company. I wanted to prove that I could do difficult things. I wanted to make a lot of money. No joke, I wanted to be featured in the X under 40 lists. Behind closed doors, I was (arrogantly) dismissive of the high-growth company’s lowly opposite, the lifestyle business. This type of venture, optimizes for quality of life and flexibility as opposed to outsized wealth and prestige. This was my own one versus five Super Bowl moment — messily capturing my usual angst around achievement, financial security, identity, and freedom. Three years into my entrepreneurial journey, I can comfortably say today that a lifestyle business is much better suited to, well, my lifestyle.

This isn’t a takedown of “excellence”

I need to be emphatically clear that this isn’t a knock on Tom Brady, the Patriots, ambition, excellence, or even doing things for money. I am in awe of what Tom Brady has done in his career — there are parts that I’ve tried to emulate, and others I’ve abandoned (seriously, dude — the strawberries).

On the contrary, it’s an invitation. An invitation to examine the motivations behind winning your own Super Bowls and discerning both the benefits and trade-offs that come with that journey. And noting that these trade-offs evolve with time and life circumstance. I know that for me, they’re completely different when you’re young and single, raising two young kids, and (presumably) when your kids are self-sufficient.

Regardless of your ambition, consider (even for 1 minute) the journey

If you want to add a bit of spiritual joo joo to this football-heavy conversation, there’s the trade-off between the journey and the destination. This doesn’t mean we should drop everything and live in the moment. On the contrary, Zen Hospice Project founder Frank Ostaseski encourages us to invest in the people we love yet to have a plan, hold it lightly. Robert Hastings’ poem The Station captures this tension beautifully:

“Yes, when we reach the Station, that will be it!” we promise ourselves. “When we’re eighteen. . . win that promotion. . . put the last kid through college. . . buy that 450SL Mercedes-Benz. . . have a nest egg for retirement!” From that day on we will all live happily ever after.

Sooner or later, however, we must realize there is no Station in this life, no one earthly place to arrive at once and for all. The journey is the joy. The Station is an illusion–it constantly outdistances us.

I recently spoke to a talented and ascending venture capitalist in San Francisco about this. He is in a dream role, but the hours, travel, and emotional commitment are demanding — approaching burnout levels. Married, but pre-kids, he wondered aloud how he could sustain this pace once they had kids. He told me, “Right now, I think I want to win more than one Super Bowl. Maybe two, but that’s it.”

Hi, I'm Khe Hy and this is from my weekly newsletter. RadReads is like "broccoli for your brain" and read by 15,000 entrepreneurs, creators, and thinkers. Subscribe here and join our conversation about deliberate ambition in both our work and lives. I also host the Rad Awakenings Podcast and write at Rad.family.

RadReads n°159

SUBSCRIBE // The marriage decision, statistics in a misleading age, the modern manager guide, intentions vs. time

Photo by Lucas Davies on Unsplash

‘Sup RadReaders,

Welcome to our newest community members. We’re constantly growing, in fact, we’ve got our first happy hour in Washington DC on March 14th (sign up). I’m also humbled by the number of responses for the Frank Ostaseski podcast(and book review).


Our webinar series continues onwards with How to Start Blogging on March 9th. The video and slide presentation for the Omnifocus webinar are now live.


The Marriage Decision: Everything Forever or Nothing Ever Again

21 mins | Wait But Why

What better way to honor Valentine’s day than with a quirky and thought-provoking post on arguably the biggest decision we make. Even if you’ve taken the plunge, this essay captures fear, “trusting your gut,” avoiding edge cases amidst our primal forces. (Serial entrepreneur Auren Hoffman and I talked extensively about marriage as a “default option” on the podcast.)


Stepping into your shadow

57 mins | Rad Awakenings | iTunes | Google Play

Abby Raphel grew up in a two stoplight town in rural Florida, where she raised hogs, swam competitively, and was exposed to leadership at a young age when she joined the Future Farmers of America. She started modeling in college and moved to New York with two bags and two phone numbers. But as a “broke and B-rate model,” she went on to teach young girls about self-esteem then founded the Redwoods Initiative, an investment education company that helps the uber-wealthy navigate their money. also discuss self-improvement and privilege, the role of hyper-agents in effectuating change, and confronting your shadow.


Tim Harford’s guide to statistics in a misleading age

15 mins | Financial Times

How does one develop “everyday practical numeracy?” Harford uses the “index card trick,” that is, fitting everything you need to know on one card. The six tricks: observe your feelings, understand the claim, get the back story, put things in perspective, embrace imprecision, and be curious. (PS — the story was not paywalled, as of the time of writing. Try Googling it, if you have issues.)


The Indispensable Document for the Modern Manager

11 Minutes | First Round Review | HT: @ryandawidjan

We’ve written in the past about User Manuals, IMHO an under-utilized tool for transparency within a team. User manuals clarify social norms and facilitate different working styles and expectations. This one is particularly cool because the author is hyper-aware of his own quirks and expectations such as “[let’s avoid] recency bias in 1:1s,” “track sophistication of new hire questions.” and “on micro-management, I’m hands-on until I trust you.” Noted!


You Never Have Time Only Intentions

4 mins | Raptitude | HT: @morganhousel

I’ve recently been obsessed with time. It’s a never-ending source of anxiety that also causes strange non-economic behaviors. Because of time’s ephemerality, we never actually control it — thus we never “have time,” only “intentions.” And this isn’t just semantics “there’s a tremendous difference between believing you own and control the upcoming three hours, and understanding that you have intentions for it but don’t own it.”

Below the Fold

LONG READS
🐺 Too Clever By Half (20 mins, Epsilon Theory): A wonderful, finance-heavy post on playing the meta-game, through the lens of “coyotes vs. raccoons.”

🏂 Chloe Kim: the face of the Korean Olympics (7 mins, The San Diego Union Tribune): I love reading about the sacrifices made by other parents for their children, particularly through the perspective of immigrant parents.

🖥 How to Design Social Systems (Without Causing Depression and War) (13 mins, Joe Edelman): This takes a bit of time to get rolling, but if you’re interested in design thinking, community, and social media it’s a wonderful piece.

ICYMI
🎙 Have a plan, hold it lightly: Don’t miss Frank Ostaseski on this moving podcast about fear, delayed gratification, and mystery. I also reviewed his must-read book The Five Invitations.

💼 RadJobs: Some sweet new gigs this week including an investment associate at a high growth NYC family office, Instagram, Facebook, Netflix, SafeGraph, Pantera Capital, and Sole Bicycle Co. If you’re looking to have your dream job delivered directly to your 📱, sign up here!

✅ How to use Omnifocus A YouTube video and presentation on why anyone would pay $50 for a to-do list app.

LAST WEEK’S MOST READ
🚀 Crafting a life (15 mins, The Economist 1843): Are there cracks in the Neoclassical economics belief that work is, by definition, a cost?

https://upscri.be/277e81/

What Unhappy Millennials Can Learn From 70 year olds

Avoid the thirty year happiness trough


As a kid, did you ever dream of being a certain age? When I was really little, I wanted to be “big” so that I could go to work like my dad. Mostly because I loved the french fries in the cafeteria. As teenagers, my suburban friends would dream about the freedom that came at sixteen with the learner’s permit. And in college, who didn’t count down the days until your 21st birthday? Once I hit that birthday, I stopped wanting to be a different age.

What’s the perfect age?

Well, we can start with what apparently isn’t. There’s the well-documented U-Bend of happiness, a longitudinal study in which participants were surveyed about their happiness. Once the childhood innocence and joy faded (around age 20) there was a stunning trough until age fifty, at which point happiness started to climb again. Some of the happiest folks out there are in their 70s. Think about that — US life expectancy is 78, yet they feel time affluent!

Why the thirty-odd year trough of unhappiness? Blind childhood optimism meets adult realities. Stress about work, money and kids. We try to stand out within our tribe.

Expectations, meet reality

And then there’s expectations. I’m sure that as a child, many of you fantasized about becoming president, vets, athletes, or astronauts. You could call these dreams, unhindered by expectations and probabilities.

Somewhere along the way these dreams hardened and turn into expectations. Why? As social creatures, there’s the irresistible force of external validation. It gets even more confusing when you add financial security, meaning, and mortality into the mix. And with expectations comes the attachment to specific outcomes. Some are subconscious, some set by our peers and others are downright arbitrary. This isn’t a dig at ambition, instead it’s an invitation to look more closely at ambition itself. Let’s now revisit the trough, then the inflection point of the happiness curve:

“Middle-aged people tend to feel both disappointed and pessimistic, a recipe for misery. Eventually, however, expectations stop declining. They settle at a lower level than in youth, and reality begins exceeding them. Surprises turn predominantly positive, and life satisfaction swings upward.”

What the woke 70 year olds know

I’m unwilling to accept that I’m at the midpoint of 30 year happiness trough. So what pearls of wisdom can we steal from these wise septuagenarians?

  • None went to a job he did not like, coveted stuff she could not afford, brooded over a slight on the subway or lost sleep over events in the distant future.
  • They came to accept their strengths and weaknesses, gave up hoping to become CEO and learned to be satisfied as assistant branch manager, or with their watercolour on display at the church fete.
  • They have fewer rows and come up with better solutions to conflict.
  • They are better at controlling their emotions, better at accepting misfortune and less prone to anger.
  • They cherished the small, daily interactions, and set realistic goals.
  • They had known adversity and survived.

So back to our original question — what’s the perfect age? The “exact time that you realize how absolutely short life is” and “how completely lucky you are.”

Hi, I'm Khe Hy and I'm this essay originally appeared in my RadReads, my weekly newsletter. Join 15,000 entrepreneurs, creators, and thinkers by subscribing here. Through the newsletter and Rad Awakenings Podcast, I'm eager to spark a conversation about fear, anxiety, and insecurity - through the pragmatic lens of work and life.