RadReads n°153

This Week: The playbook for leaving your corporate job, why envy trumps self-interest, the weak link in your digital security

Khe Hy
RadReads
8 min readJan 7, 2018

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Good Morning, RadReaders 💚

I hope everyone’s 2018 is off to a great start! Don’t miss the podcast links in today’s below the fold — they contain some real gems.

I’m speechless and grateful for the surge in new patrons (7!?!). Thank you Chris, Callie, Andrew, Raya, Rachel, Sanyin, and Michael. You’ll start to see a new hub for our community emerge at rad.family and this is entirely due to our Patron’s generosity. Join the fam for as little as a Venti Pike per month by clicking below.

🤘Join our #RadFam 🤘

We’re starting off the new year with a bang 💥 over at RadJobs. This week, we’re bringing you a record count 🏆 of new opportunities. Find roles from Apple, Kickstarter, Sir Kensington’s, Quartz, RiskGenius, All Turtles, BlockTower Capital, and IWillTeachYouToBeRich.com. If you’re looking to have your dream job delivered directly to your 📱, sign up here!

The unsexy steps to chasing your dreams

Rad Awakenings | 50 Mins | iTunes | Google Play | Stitcher

At age 22, Mike Lewis had his dream job as a young venture capitalist at Bain Capital Ventures. Mike was moving up the ranks and doing interesting work with talented colleagues. But there was a little nagging voice reminding him of a childhood dream — to play squash on the pro tour, even if it meant couch surfing and eating into his savings to do so. But he went for it, achieved a peak ranking of #112 and went on to write When to Jump: If the job you have isn’t the life you want. We’re bombarded by sexy stories about people who made the jump and Mike’s developed both a playbook and community of “jumpers.”

Why Envy Dominates Greed

16 mins | Falkenblog

Incentives matter. Human beings are rational and act in their self-interest. It’s the basic assumption that drives many economic models, decision making, and policy. But does envy and humans’ status-seeking behavior wreck havoc on these models? There are examples in finance (assets with higher vol have lower returns) or kids’ behavior (their desire to share depends on what the other kid has) which show how we benchmark our sense of well being relative to others. (Note, it’s completely acceptable to skip over the more technical parts of this essay.)

If work dominated your every moment would life be worth living?

5 mins | aeon

Are we living in an era of Total Work? “The total worker, in brief, is a figure of ceaseless, tensed, busied activity: a figure, whose main affliction is a deep existential restlessness fixated on producing the useful.” But total work is a rather new phenomenon — could it be both the cause AND the result of firing up Maslow’s hierarchy (My speculation, not the Author’s)? Andrew and I discussed a potential remedy, a life of contemplation and I encourage you to sign up to his Total Work newsletter.

Want to Be Happy? Think Like an Old Person

4 Minutes | The New York Times

Octogenarians are the fastest growing age group in America. And they embody the paradox of old age: as minds and bodies decline, happiness increases (also demonstrated by the U-bend of happiness). Why? They had known adversity and survived, cherished the small, daily interactions, and set realistic goals (and presumably abandoned the Total Work mindset 😜).

Protect your digital accounts by disabling number porting and SMS-based password recovery

2 mins | RAD Awakenings

My informal RadReader poll reveals that less than half of you use a password manager. Please do that ASAP, I’ve had many friends get their bank accounts liquidated because of poor security. (Even with my heightened security, my Paypal account got compromised). But once you do that, guess what, the weakest link is actually your cell carrier. It’s rare for me to do a RadReads PSA, but in our digitally interconnected world, we’re only as strong as our weakest link.

Postscript

This week I stumbled upon “cuddle puddles,” a sex and drug infused bacchanal for Silicon Valley’s elite. I personally don’t care what folks do in the privacy of their own mansions, but one paragraph stood out:

But many of the A-listers in Silicon Valley have something unique in common: a lonely adolescence devoid of contact with the opposite sex. Married V.C. described his teenage life as years of playing computer games and not going on a date until he was 20 years old. Now, to his amazement, he finds himself in a circle of trusted and adventurous tech friends with the money and resources to explore their every desire.

This reminded me of a recent interview with uber-entrepreneur Elon Musk in which he says:

“If I’m not in love, if I’m not with a long-term companion, I cannot be happy. (…) I will never be happy without having someone. Going to sleep alone kills me.” He hesitates, shakes his head, falters, continues. “It’s not like I don’t know what that feels like: Being in a big empty house, and the footsteps echoing through the hallway, no one there — and no one on the pillow next to you. F*ck. How do you make yourself happy in a situation like that?”

Though I’ve never partaken in a cuddle puddle (my wildest evenings were at Twilo in the late 90s) I can relate to both of these paragraphs. I was a shy, skinny, and awkward high school guy who did not run in “cool” circles and didn’t go on a date until I was 19. And like Musk, my deepest fear was being unable to find love — and spending my life alone.

In fact, this probably served as one of my greatest sources of motivation from a very young age. Work your butt off. Make money. Achieve status. This will guarantee that you don’t end up alone. It’s mildly embarrassing when you lay it out so crudely, but my guess is some of the cuddle puddlers also shared this motivation.

I pass no judgment on whether the merits of this source of motivation. But I can’t help but recognize some of the unintended consequences. As is the case with the nouveau riches, a spectacular leap in wealth or status can be a bit disorienting. I personally felt that in the early days an Wall Street, where, to put it kindly at times I acted like a douche. But below the surface was the 16 year old scared-to-be-alone-Magic-the-Gathering-player unable to wrap his arms around the fact that he could walk into a lounge, spend some money on over-priced drinks and maybe (just maybe) strike up a conversation with the opposite sex. It’s also when the Three Es (Ego, Envy, and Entitlement) started to infiltrate many of my attitudes and behaviors.

Next, there’s the belief that extrinsic goals can quell general feelings of unsettledness. It’s that feeling of “once I get there, my life will be calm/happy/fulfilling.” As a goal-oriented individual, I’ve countlessly experienced checking off an item (both big and small) only to find my happiness revert to the mean. My personal mantra is “there is no there,” you never get “there.” This doesn’t diminish the angel that chose me as her husband (she literally came up to me at Pacha in 2007 as I was too shy). On the contrary, the fear of being alone is now replaced by the thought of having to live my life without her.

And then there’s what my friend Andrew Taggart calls the “problemization” of the universe, the notion that life is problem to be solved. Many overachievers rely on the new religion of “problem, challenge, solution, repeat” in every dimension of their lives. (This playbook doesn’t work in marriage.) Problemization really messed with me by giving me a false illusion of control. As I age, reconciling this control with randomness and uncertainty is a big source of anxiety.

So where does that leave us? For starters, if you are a nouveau riche (cuddle puddler) you can still honor the loneliness and solitude in others. You can also remind yourself that striving and individualism are not mutually exclusive from community and family. And finally, remembering every single one of us has love to give — and there’s probably someone a few feet or a phone call away who will eagerly accept your love with open arms.

Below the Fold

MULTIMEDIA
🎙 Joe Rogan interviews Dan Carlin (120 minute podcast): Start at 1:48:00 where they discuss unbundled careers, how to start the smallest side hustle, and the golden age for creators. Both of are examples of obscure creators who harnessed their micro-expertise to build massive digital platforms.

📺 Want to get great at something? Get a coach (20 minute TED Talk): One of my favorite writers Atul Gawande gets a coach — to help him become a better surgeon.

🎙 Businesswoman Special (60 Mins Podcast): Journalist and reporter Ann Friedman discusses the economics of podcasting. Her pod, Call Your Girlfriend, started out as just that — an excuse to call her girl friend in LA.

ICYMI
🎙 From the cave to the trading desk (Rad Awakenings Podcast): My two-part interview with Philip Simon on reading, lifelong learning, being a contrarian, and privilege.

📚 The books RadReaders devoured in 2017: 38 book recommendations from the #radfam.

💡 Reflections on 2017: And some growth and editorial plans for 2018.

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Khe Hy
RadReads

CNN’s “Oprah for Millennials” + Bloomberg’s “Wall Street Guru.” I write about fear, ambition, and mortality. http://radreads.co/subscribe