wait but why (are Gen Ys unhappy?)

The article explains why Gen Y yuppies (whom the author nicknames GYPSYs) are unhappy. It suggests 3 reasons:

1. Happiness = Reality – Expectations

We (GYPSYs) have unreasonably high expectations.

Our parents and grandparents’ generations had simpler goals: secure jobs, homeownership, a loving family.

The GYPSY needs a lot more from a career than a nice green lawn of prosperity and security. The fact is, a green lawn isn’t quite exceptional or unique enough for a GYPSY. Where the Baby Boomers wanted to live The American Dream, GYPSYs want to live Their Own Personal Dream.

wait but why(The stick-figure artwork is a plus)

According to Cal Newport, the phrase “follow your passion” barely existed 20 years ago!

This reality-expectations gap is made worse because…

2. GYPSYs think they’re special and unique

We not only have higher goals, but we measure success in comparison to everyone else. And there’s always someone smarter/richer/better-looking/etc

“Sure,” Lucy has been taught, “everyone will go and get themselves some fulfilling career, but I am unusually wonderful and as such, my career and life path will stand out amongst the crowd.” So on top of the generation as a whole having the bold goal of a flowery career lawn, each individual GYPSY thinks that he or she is destined for something even better—A shiny unicorn on top of the flowery lawn.

These comparisons are easier than ever to make, due to…

3. The downsides of social media

Social media creates a world for Lucy where A) what everyone else is doing is very out in the open, B) most people present an inflated version of their own existence, and C) the people who chime in the most about their careers are usually those whose careers (or relationships) are going the best, while struggling people tend not to broadcast their situation.

Their solution? Stay ambitious. Stop thinking you’re “special”. Ignore others’ success.

A fun read.

A (sarcastic?) reader comment:

This is pretty cool… except I am special. Call me a gypsy, but I studied a real major in college, went on to get my masters, had a 4.0 throughout, got my dream job, earn great money, have a smokin’ hot wife, a big house, nice car, a muscular physique and am smarter than most people I have ever known or met.

Thanks Alex for the find.

August and September Books: lots of fiction and a few audiobooks

Thanks to Yujin, I’m addicted to Farnam Street. It’s the blog I wanted to start :)

Here are the books I read in August and September. I’m using a simpler format, with the hope that less work = more consistent updating.

August

I drove from LA to San Francisco twice in August, hence the 3 completed audiobooks. Oh, and plenty of podcasts.

The Launch Pad: Inside Y Combinator by Randall Stross

I kept putting off reading this book, but after unabated nagging from a few friends, I took the plunge and got through it pretty quickly. Stross provides a great refresher of YC lessons learned, and his behind-the-scenes access unlocked plenty of new insights and stories.

On Writing: A Memoir of the Craft by Stephen King (audiobook)

Did you know Stephen King had his first short stories published at the age of 18? And that his ironclad rule is to write 2000 words a day, every day (holidays and weekends included)?

It reminds me of that Somerset Maugham quote,

I write only when inspiration strikes me. Fortunately it strikes me every morning at nine o’clock sharp.

Stephen also dislikes adverbs, for example “he aggressively jumped” or “she silently tip-toed”.

Thanks Magic Ming for the rec.

The Inner Game of Tennis by W. Timothy Gallwey (audiobook)

It’s nominally an investigation of how average tennis players like myself can perform at their highest level, but its lessons can be abstracted into a life philosophy on how to overcome obstacles, face competition, and be your best self. Some of Timothy’s lessons are trite and of the self-help variety, for example his belief that opponents are blessings in disguise, but overall I enjoyed reading the book and understanding the difference between my conscious and subconscious self.

Stein on Writing by Sol Stein (audiobook)

You know you’re a big poo-bah when the title of your book can follow the format “[your last name] on [some topic]”. Like “Jordan on Basketball” or “Santana on Guitar”. I guess that’s where Stein fits in the pantheon of book editors, having published the works of David Frost, Elia Kazan, W. H. Auden, and Jacques Barzun. I learned so much from the audiobook that when it was finished, I immediately started over and listened to it again. For example, the best dialogue should be oblique, as in:

Harry: “Did you like that new movie Gravity?”
Sally: “How can you not like a movie with George Clooney AND Sandra Bullock?”

The dialogue is oblique because Sally doesn’t just say “Yes” or “No”. So yeah, many nuggets like that.

September

Dominated by fiction.

The Giver by Lois Lowry

Yes, I read this book in middle school and I think it’s really meant for on-the-cusp adolescent boys. Where the re-reading urge came from, I can’t tell you. But I’m glad I re-read it, particularly the first half which focuses on how Jonas discovers his gift and how it changes both his relationships and his view of the world. I find it amazing that an adult author can write something which touches both children and adults, sort of like Pixar does today with its movies. The Giver profoundly affected 12-year old me, and it’s probably changed the lives of millions of kids and will continue doing so. Powerful stuff.

Hard-Boiled Wonderland and the End of the World by Haruki Murakami

As I’ve mentioned too many times before, I love Murakami’s writing. Like going on a run with a really fit friend, it pushes you beyond the limits of what you thought possible, and you’re left better for the experience with an undeniable reader’s high.

Not all’s perfect in Murakami-land, though. His sometimes bizarre, usually unpredictable endings can be aggravating, because I like to have my literary i’s dotted and t’s crossed. Those endings can feel like a girl who careens into your life, crashing through the emotional boundaries that you’ve carefully built, and then vanishes without a warning, leaving you with questions that your heart keeps asking but your brain knows will remain unanswered.

…or something like that, I imagine.

Kafka on the Shore by Haruki Murakami

The 2 books are so different that it doesn’t matter what order you read them in. Hard-Boiled was more…cerebral. And Kafka left me with a melancholy that is I wouldn’t try to explained.

If you do read them – or any of the other books – I’d love to hear your thoughts. Always open to recommendations as well. Cheers!

5 great articles – John McEnroe, Scott Weiss, Chris Dixon, Dr. Drew and The People’s Premier

Every article I read through the browser is shared via Clearly and a public Evernote notebook.

Since I doubt anybody checks it (on a regular basis, anyway), I wanted to step up the frequency of sharing interesting links, like what Seth Roberts and Tyler Cowan do with their Assorted Links.

Here are 5 recent articles I enjoyed:

  • Old article and my site may get blacklisted in China as a result, but former China Premier Wen Jiabao’s extended family is worth $2B. Hats off to NYT on great investigative reporting and ohhh, China
  • Beautifully written article on the tension between the pursuit of perfection and the management of one’s emotions featuring America’s favorite mercurial tennis player John McEnroe. I actually thought this famous outburst was overrated
  • 2 great posts from a16z’s Scott Weiss (former IronPort CEO and cofounder) on underlooked aspects of being the CEO: the need for tough feedback on a personal and board level. I really enjoy Scott’s ability to write in an upbeat tone while sharing much-needed truths
  • Chris Dixon with yet another short but thought-provoking piece on the macro-trend of digital content atomization. I’d add that, in such an environment, curation and synthesis become even more important (yes, that’s a self-serving remark :)
  • I’ve been hearing the word “grit” a lot lately. First from Dr. Drew and now popping up everywhere. As a predictor of career success, it’s the “new IQ” among the social science crowd

Why does “touchstone” mean what it does? And other words

Raining cats and dogsI’m fascinated by the history of words and phrases that have more than just a literal meaning. Why does it “rain cats and dogs”? How did “eavesdropping” come to mean listening furtively to other peoples’ conversations? And is a touchstone an actual stone?

A touchstone, as used in casual conversation, can mean two things:

  • A way to measure the quality of something, as in “His athletic success became a touchstone for future athletes at the school”
  • An essential part of something, as in “Nirvana was a touchstone of the grunge music scene in the 1990s”

Where does the word touchstone come from?

According to that most wonderful of resources Wikipedia, a touchstone is an actual stone. More precisely, it’s a small stone tablet used to determine the quality of precious metals like gold and silver. When you use gold to draw a line on a touchstone, it leaves a streak, the color of which can be compared to streaks from gold pieces of known quality and composition.

Fascinating, right? Although explaining why it’s popular today is much harder, like trying to explain why we use “what’s up?” to greet people. Who knows, maybe some famous person decided to use it and it spread from there.

Now I’ll answer the first 2 questions with less precision.

In England several centuries ago, when it rained really hard, stray dogs and cats would drown and pile up in the gutters. Thus the phrase “it’s raining cats and dogs”. Makes you think twice about using that phrase, right?

As for eavesdropping, there are several competing explanations, but old houses used to have eaves hanging from their roofs. Thus if you were right outside the window or door, secretly listening to the conversations inside, you’d be beneath the eaves and thus eavesdropping.

What words or phrases can you explain? I’d love to hear.

1-Read-A-Day: what I learned running a newsletter, September edition

Every month, I share stats and learnings on the 1-Read-A-Day newsletter. Here’s the launch post.

How well is it doing?

Subscribers: 220 (last month: 161)
Open rate: 22.9% (22.8%)
Click rate: 2.6% (2.2%)

Thanks to Kale’s feature, I got 27 signups in a single day. By far the largest jump since the July launch. I highly recommend subscribing to his Hacker Newsletter and also enjoy his Wayback Letter, a nice way to re-surface classic content that has disappeared from the interwebs.

What did I learn in September?

1. Per Tommy’s advice, I customized the Gmail preview snippet.

Open rates have increased, but it’s correlation, not causation. The change makes me feel better, though.

To customize the snippet and not harm the email’s readability, I explored several options but went with this one: the text snippet is placed it at the top of each email, then the font size is set to 1 and font color to white, so it’s invisible to readers.

2. Readers complained they couldn’t distinguish direct quotes from my color commentary. So I added a quote symbol inside each yellow box. This has received positive feedback, but there is a downside: before, each email was image free and did not require you to click “Display images below” (if you’re using Gmail) to load the quote-symbol-image. Another lesson: product “improvements” are often double-edged swords

3. Quizzes are the most complimented feature, so I added more questions to each quiz. I will also have a big, 10-question quiz after Lesson 50. I’m even thinking of launching startup quizzes as a separate project. “test your startup IQ” sort of thing

4. There’s a tension between esoteric and popular content. Well-read startup folks appreciate the esoteric content, but it’s often esoteric for a reason (niche appeal, out-of-date, too technical). However, I do agree that I’ve relied heavily on popular content, so going forward, I will feature more esoteric/lesser-known articles and bloggers (such as this thoughtful essay from Max)

What’s coming up – niche email courses and audio lessons

My goal was 50 lessons before I began to widely market the newsletter and release topic/problem-specific email courses (eg, 20 email lessons on hiring engineers, or 35 email lessons on raising a VC round). I’m on lesson 50 (congrats if you’ve read all of them), so these are coming soon.

I’m also planning to record 60-second podcasts for each lesson, for those who enjoy audio learning and have time to kill on the daily commute or while at the gym.

Thanks to all my subscribers for your participation and feedback. Keep it coming, it’s been a pleasure to do this. Here’s to showing up and getting to work. Cheers!

PS. If you run an email newsletter, I’d love to hear what you’ve learned, what works, and what doesn’t.