I was talking to some folks about applying to Y Combinator [1] and preparing themselves to found a startup more generally. One point that I found myself talking about, especially in terms of timing, was the two distinct emotions that I that many founders seem to posses, especially in the early days. [2]

They have an intense dissatisfaction with something in the world and an irrationally large sense of confidence about themselves.

As any founder will tell you, doing a startup is hard. Being passionate about the market you’re tackling, having a love for building great products —  that’s all well and good. But when push comes to shove, there are few things more motivating than being a little pissed off.

When you’re mad, you work harder, you hold out longer, you move faster. You might be mad at the big players who are screwing over consumers, mad at your old boss who turned down your promotion request, mad at all the investors or media people who don’t get what you’re doing.

And that anger is fuel.

Paired with the anger is thinking you are the shit. To take the plunge and do a startup is to implicitly say:

“Despite the fact that most startups fail, I think I can succeed. And thus I believe I’m smarter, more capable, more persuasive than the majority of founders.”

It takes some cockiness to say that. Think about Elon Musk, Steve Jobs, Mark Zuckerberg, Paul Graham, Jack Dorsey. [3] In their own way, each had a tremendous belief in themselves: their vision, judgement and abilities.

When I started Ridejoy, I had a chip on my shoulder, in part because the CEO of the startup I worked at once told me I was “a bit junior”. And yet he had dropped out of college to start that company and was the SAME AGE AS ME.

I’ve always had a unreasonably large amount of confidence and I did believe that I was better than other founders. Getting into Y Combinator certainly supported that thesis. [4]

By no means were these qualities “everything you need” to be a success. In fact, you’ll still most likely fail. But if you were thinking about making the leap asked me if NOW was the time to start your company, I’d ask: “Are you feeling a little angry? And a little cocky?”

FOOTNOTES

[1] If you don’t already know, I’ve written a 92 page guide to applying to Y Combinator – you can get it for free if you sign up for my email newsletter

[2] Clearly this is anecdotal evidence —  and yet our brain is wired to respond to stories and data of this nature. Take from it what you will.

[3] Same deal as [2] – correlation doesn’t prove causation, but sometimes it can suggest it.

[4] I say that at the risk of sounding like an douche, but I’m just telling the truth. When you’re in the top 7% of thousands of teams who apply to YC, you start to feel a little special.

Related Posts:

• Ariely Talk on Psychology of Money
• Violent Plans (quote)
• Data-Obsessed Guy Seeks Technical Cofounder via Hilarious YouTube Video
• Startup Founders: Don’t Forget to Sell the Dream
• Cronyism is alive and well (or why relationships matter)

I normally don’t write about random stuff I find on the internet but this was too good to pass up. I was on Facebook and came across an ad that asked “Will you be my cofounder?”

Amused, I clicked through and I hit a 5+ minute YouTube video of a guy named Daniel Vitiello who’s looking for a technical cofounder for his business. Here it is below:

I’m torn: on one hand, it’s a great example of hustle as Dan talks about the 166 pages of research he’s done on “the data ecosystem”, the industry leaders he’s networked with and the MVP he’s set up — a service that allows consumers to sell their own grocery store reward data directly to data companies and advertisers.

On the other hand, it’s full of awkward/painful moments, like when he does the “Oh hey! Didn’t see you there” walk by, or throws out cheesy lines like “I’ve tested and failed fast with eleven different business models” and “If you are Googling me and see a mug shot, don’t worry. It’s all been taken care of.”

Ouch.

Finding a cofounder is hard as hell and I admire the creativity, but I’m not sure this is going to work out for Dan. The video is a hidden gem though.

Are you a developer? What would be your reaction to this kind of a recruiting pitch?

Related Posts:

• A Little Angry, A Little Cocky
• Startup Founders: Don’t Forget to Sell the Dream
• When Software is Eating the World, You Better Start Making Dishes
• Thoughts on Competition for Early Stage Startups
• Take Advantage

Here’s what I’ve done so far:

• Jan: Sit-Ups in 1 Min (pre-training | post-training)
• Feb: Handstand Pushups (pre-training | post-training)
• March: One Mile Run (pre-training | post-training)
• April: ???
• May: Pull-Ups (pre-training)

So what happened in April?

Well, my goal was to train for the flagpole. If you don’t know what a flagpole is, it’s where you grip an upright pole and pull yourself horizontal. It requires a lot of core strength + alternate bicep/tricep strength (depending on what side you push/pull on).

Here’s a picture of me doing one in a photoshoot for Outside Magazine:

(it’s actually not perfect because I’m angled upward instead of being fully perpendicular)

Anyway, I went on a trip to Southeast Asia in April and somehow tweaked my back, which made it rather painful to perform the flagpoles. So I have the “pre-trained” flagpole footage, but no post-training. =(

I hope to make a full recovery from what I believe is a pinched nerve in my lower back, and then I can maybe double up one month, training for 2 activities and complete my year. Will keep you posted!

Get to the Pull Ups Already

Alright, so that’s a long way of saying: I’m sorry I dropped the ball, but I’m back in the game. Here’s my pre-training video for max pull-ups. Note: The sound is a little off at the end and I’ll try to fix that, but let’s be honest, you’re not watching the video to hear my luminous voice.

(Email readers click through to watch the video)

Related Posts:

• FitChal #2: Max Handstand Pushups (Final)
• FitChal #2 Start: Max Handstand Pushups
• FitChal #1 Finale: Max Sit-Ups in 1 Minute
• Introducing The Monthly FitChal (Max Sit-Ups Pre-Training)
• Running a Fast Mile

He’s an account strategist at Google, a gig he earned after investing dozens of hours of preparation through a system of gamification that he created for himself. It’s fair to say that he’s pretty obsessed with engineering his behavior. But as I’ve said, winning isn’t normal, and I think there’s a lot to learn from Jonathan’s approach to behavior change.

So enjoy and here’s Jonathan:

My experience with rejection (and how it benefits you)

One of my first encounters with The Art of Ass Kicking was reading about Jason’s experiences with Rejection Therapy. The idea of Rejection Therapy resonated with me for one reason, and one reason alone: rejection scares the living crap out of me. Nevertheless, handling rejection is such an important life skill, I didn’t feel it was an option to allow myself to be affected so strongly by it.

While all rejections are less than pleasant, I tend to let rejection control me most in social realm – especially when it comes to introducing myself to strangers or asking girls out. Quite aware of this, I’ve recently decided it was time to be more proactive with this area of my life. But rather than use a brute force strategy (i.e. pound shots when I’m not feeling social at a party), I wanted to create a system that subtly, but consistently guided me to take positive actions, even with the risk of rejection present.

My weapon of choice for creating this system was gamification, the application of game mechanics to systems where they may not have otherwise existed. Although I was new to the use of gamification for rejection therapy, I’m no stranger to using gamification to get things done, build habits, and achieve epic wins. In this post, I’ll be focusing on the use of gamification for systematically overcoming rejection. I’m still in the midst of this long-term experiment, so I’ll be sharing my progress thus far, with the hope that you can use these techniques in your own life.

Getting started

The best way to learn to handle rejection is simply to get rejected more often. If only it were that easy though. I knew that I needed a system in place to guide me to tolerate (and even embrace) rejection in order to experience enough rejections to become resilient to them.

So I took a post-it note, put it on my desk, and scribbled the following:

Each box on the post-it note represents a milestone, which, in this case, is a new rejection. Upon reaching five rejections, I’d earn the reward on the bottom of the post-it note. A quick and easy reward system for taking actions I found uncomfortable. However, knowing myself and how consistently I avoid rejection, I knew this wouldn’t be enough.

So I added another game mechanic: variable rewards. For every rejection I attempted (even if I failed), I’d get to flip two coins. If they both landed on heads, I’d earn a bonus reward (in this case, a book from my Amazon.com wish list). This mechanic was designed to encourage me to take action towards this goal, regardless of whether or not I was successful in earning my rejection. With these two mechanics (milestone tracking, variable rewards) in place, I was ready to get started.

Finding the rejections, kaizen style

Now that I had defined my starter goal of five rejections, the next step was identifying how to put myself into likely rejection scenarios in order to build up my rejection tolerance. If there’s one thing I’ve learned about setting goals, it’s that you need to start slow and build your way up through steady, continuous improvement (often referred to as kaizen). Those who attempt aggressive changes at the beginning of a goal are likely to experience strong resistance and backtracking. To avoid this, I started small with only five rejections.

From there, I realized that some rejections are much worse than others. For example, being blatantly rejected in public is significantly worse than when you don’t receive a reply from someone you’ve been talking to on OKCupid. So I decided to start with the easier rejections to tolerate, and then ramp up the difficulty level with every increment of five rejections.

How did I find this first round of rejections? Simple. I hopped on OKCupid and spent a week setting up a few dates for myself. I had been looking to start dating again anyways, so I saw it as a win-win. Either I’d get rejected, and get one step closer to my goal, or I’d find a good match in the process.

Results so far

I won’t go into the series of long (oftentimes entertaining) stories about the dates I went on for this experiment; suffice to say, I have three rejections down, two to go. Those three rejections were earned fair and square, but they’ve also shown me how far I have to go before I can comfortably handle more intense forms of rejection.

As you can see in the image above, I’m still in progress with my rejection goal. I’ve only hit three out of five so far (as seen on the leftmost post-it note), so I’m still finding ways to get rejected. However, once I reach five rejections, I’m planning to move beyond OKCupid dates because those rejections don’t sting nearly as much as they used to (I’ll discuss this more below).

Additionally, to assist with this experiment, I’ve added a new game mechanic based on streak bonuses. In a nutshell, if I can go 10 days in a row, during which time I converse with a stranger each day, I’ll earn a bonus reward. If I miss a day, I have to start over. Currently, I’m at a streak length of 7. Here’s to hoping I can make it to 10 days!

After going through the trial phase of this experiment, yeah, I’m left with some awkward memories, but I’m already reaping some pretty awesome benefits.

• My attitude towards dating is healthier. After going on five dates in one month – two good, three ending in a rejection – my attitude towards dating is a bit more relaxed. Although the rejections were very frustrating at first, they started impacting my mood much less once I became comfortable with the idea that not every girl will be interested in me. This has been the biggest benefit thus far, since the last thing dating should be is stressful.
• I’m more confident. Competence breeds confidence. Rejection usually involves some sort of failure (clearly, you don’t really intend to be rejected, so it’s a failure when you do). And as we all know, failures are amazing learning opportunities for next time. Pushing past the fear of rejection has allowed me to fail faster, which has subsequently allowed me to learn faster and become more comfortable with the activity at hand.
• I have more fun! When your fears have less of an impact on you, you’re free to have fun and enjoy your life. I’m still a world away from having my dating life handled, for instance, but I’m better able to enjoy the ride from having starting this experiment.

Looking ahead: Other ways to gamify rejection

Now that I’m looking to go beyond rejections from dates, I plan to focus more on talking to strangers (as noted in the previous section). I think that being comfortable when it comes to connecting with people you don’t know is quite a valuable skill. As such, here are some game mechanics I’ve either recently implemented, or plan to implement soon:

• Streak tracking for conversing with a stranger each day (seen in the image above)
• Earning points for how embarrassing the rejection, and redeeming those points for a reward (testing this in phase two)
• Creating a small web app that lets me and my friends track our rejection metrics against each other (project for down the road)

Gamifying goals is a topic I’m very passionate about, so drop me a line if you’re interested in talking more about it (email: jrrera@gmail.com, twitter: @jonguerrera). I also write about it extensively on my blog, Living For Improvement.

Related Posts:

• The Six Fundamental Elements of Effective Behavior Change
• Three Studies Find Ways to Get an Extra Boost of Willpower & Self-Control
• The Power of Having a Mindset of Infinite Opportunity [guest post]
• Using Variable Rewards to Drive Behavior Change
• Getting Rejected 30 Days in a Row [video]

I love taking these meetings because I get to get back to the community that has supported me plus I learn a ton in the process. For instance, it was from all these meetings last time around where I wrote my most popular post of 2012: 11 compelling startup pitch archetypes.

This post addresses a very specific piece of the startup pitch: selling the dream.

The Final 10%

The vast majority of your pitch should be around the mechanics of your business: your customers, your product, your team, your distribution strategy. This is what’s going to make you successful: competent people who really understand the needs of their users and who have the ability to create the right product to address those needs and get it into the hands of their users.

But, there is a final 10% of your pitch which should be more aspirational. It’s about the vision, the dream, the magic. It’s the answer to the question “How is this going to be a billion-dollar business?” [1]

Two of the companies that I’ve spoken to were missing that part of their pitch. They had identified a market segment which had a burning problem, and their products all that problem, and they had good specific strategies to acquire those customers. This is a great start. [2]

But they were missing that aspirational story.

Give Them Something to Dream About

You might think that investors simply invest to make money. And of course, that is a very big part of what they do. They have their own investors in the form of limited partners (LP’s) and are expected to deliver significant returns on huge sums of money.

But startup investors understand that a tiny handful of their portfolio will return most of the gains. Three-quarters of Y Combinator’s portfolio company valuation comes from two companies: Airbnb and Dropbox. And Paul Graham himself had this to say:

When you interview a startup and think “they seem likely to succeed,” it’s hard not to fund them. And yet, financially at least, there is only one kind of success: they’re either going to be one of the really big winners or not, and if not it doesn’t matter whether you fund them, because even if they succeed the effect on your returns will be insignificant. (from Black Swan Farming)

A founder who wants to raise capital from a professional investor needs to instill the sense that there may be a chance this company could be fucking massive. Because a reasonable shot at base hit or double isn’t enough. There has to be a chance this thing is a major home run. And since investors tend to have a bit less creativity and optimism (or they’d be entrepreneurs themselves) they need some help seeing that dream.

Case Study: Airbnb

Airbnb started out by letting people rent out floor space with inflatable airbeds for people to stay during conferences. Eventually it grew to helping people with an extra room or whole apartment offer that place for travelers looking for unique and affordable housing. Now you can imagine a very boilerplate startup pitch that goes something like:

“There are X million people in the US and XX million globally who have extra rooms in their house or extra homes that they keep. They’d love to make more money from that space. Meanwhile, the hotel industry is XX Billion. We think we can take X% of those travelers and direct them to our hosts and make XXX million dollars annually.”

It’s a solid pitch but completely without any aspiration or magic. Now of course, Airbnb has done a bang up job of positioning themselves so that is not at all their (admittedly customer-facing) pitch. Their section on “Live a Richer Life” captures the aspirational elements of Airbnb as a host. [3] But imagine what the sexy, magical version of the Airbnb pitch might have been:

“Airbnb enables people to live richer lives, where their extra space allows them to be with their children, take more vacations and save for retirement. We transform travel accommodations from cold, sterile rooms to amazing experiences with locals in unique spaces. How will we become a billion dollar company? Airbnb will host more travelers than the entire Hilton hotel chain with 5,200 locations around the world, without having to manage a single piece of property. We will be the future of travel.”

It’s a little different right? It’s much more than just making money. An investor, like a founder, wants to be a part of something that is really going to change the world. Something to be proud of. Something that they can say “Yeah, I invested to those guys/gals when they were just getting started because I saw the potential in what they could create and the impact they could have on the world”

Now again, I want to emphasize that 90% of your pitch should be about the nitty gritty of your business. But don’t fail to include that 10% of a dream.

I end with more words from Paul Graham from his instructions on how to apply to Y Combinator:

Like all investors, we want to believe. So help us believe.

FOOTNOTES

[1] Hint, this question should not be taken literally. It is not “We will reach 1M customers paying us each $80 a month.”

[2] I wonder if maybe their focus on business need and revenue opportunity was shaped by the “if your startup doesn’t make money, you are screwed” mindset held by many as a backlash (perhaps rightly so) to a lot of the free apps out there.

[3] And in fact, that is the top result for the Google search for “Live a Richer Life“

Related Posts:

• The Story of How a Business Guy Earned the Opportunity to Co-Found a Tech Startup
• Great by Choice: the surprising lessons of how tech startups succeed over the long term
• Aardvark Business Analysis for Stanford MBA Course
• Ignore the critics: Lean In should be required reading for everyone, including men
• When Software is Eating the World, You Better Start Making Dishes

Tell anyone you’re learning Ruby on Rails and you’ll soon get a recommendation for Ruby on Rails Tutorial by Michael Hartl. After spending 6 weeks working with Treehouse‘s programing content and building a basic web app, I decided to jump into Hartl’s tutorial.

Michael is a former Y Combinator alumni and his tutorial (from now on RoRT) takes you through building a Twitter clone in Rails. It took me around two months to finish 10 of the 11 chapters, and I thought I’d share some thoughts and lessons learned.

Even simple programs require a ton of work
Hartl has us build a Twitter clone in RoRT, without using any gems for user authentication. This ends up being a surprisingly large amount of programming. I was intimidated by all the steps involved in adding validation, building different models (user, micropost and session), creating partials, passing information between different classses and handling errors.

Super thorough and complete
I’ve never met Hartl but he seems like he’d have his sh*t together in every way. The tutorial almost like an elegantly written program in of itself: it’s complete, bug-free, modular and self-referencing. Hartl specifies the exact version of every gem, database and Rails/Ruby on Rails to use. The book had absolutely zero errors from what I could tell – every time something messed up or seemed wrong, it ultimately was an issue on my end. That gave me tremendous faith in the course.

Professional
One thing that immediately strikes you about RoRT is that Hartl has you using git, GitHub, Heroku, branching and testing right away. It feels very professional, like I was doing things the way a “real programmer” would. We used a fair number of gems, but it seemed like we used the most common/established ones. We also did a lot of things by hand, which was educational and felt very hands on.

Typos = Death
At least 50% of the total time I spent doing RoRT was dealing with errors, most of them in writing test code. I retyped all the code by hand and would misspell a function name or miss a period, comma, bracket or colon, and my test would fail. It usually wasn’t clear what went wrong, and so I’d consult Google and review the last few pieces of code I wrote, but at least I always knew it was me, and never RoRT. It was tough, but I slowly got better at checking my typing the first time around, because I knew it’d save me a lot of time in the long run.

Don’t interrupt me!
Unlike Treehouse, RoRT’s chapters got considerably long. Chapter 10 took me a few weeks to finish (though this was due in part because I got rather busy) and it required a huge amount of concentration to work through the exercises. I tend to leave Gmail open and getting my concentration broken by a gChat meant a huge loss in productivity. My best work was when I set 30 minute timers for myself to power through, then switching to social media. I bet crappy managers would probably interrupt programmers way less if they experienced this for themselves.

Reloading the context
Because RoRT’s chapters are so long, I would leave my browser tab, text editor and terminal window open between sessions (often a day or more apart). However, it often took up to 10 minutes just to figure out where I was in the chapter and what I was doing. Reloading all the context was tough. I really liked Treehouse’s module’s where they would remind me: “In our last section we did X, now we’re going to add Y.” [1]

Test-Driven Development is a bitch is tedious
When I was in middle school and high school, my biggest challenge was having the self-discipline to double check my homework answers, especially in math. It was so boring and annoying, even though I’d often find mistakes in my calculations. TDD is like creating a framework to make sure you get the right answer the first time, but it’s not as fun as just coding the functionality you want to build. And yet, like double checking your answers, TDD is necessary if you really care about getting things 100% right (or having a bug-free app).

Terminal is cool
One of the great things about RoRT is that it teaches you cool tricks in Terminal. I set up a sublime text shortcut, made “b” equal to “branch”, learned how to navigate file structures, create files and other neat shortcuts that made me feel like a real pro when it came using Terminal, a program I have come to associate with programming and technical expertise.

Final Thoughts
If programming is like driving a car, then Treehouse is your buddy spending a few hours with you in a parking lot while driving 2010 Honda Civic in automatic. And RoRT is like a 3 day intensive training course on driving a formula one race car taught by exacting German instructors.

RoRT is a lot of work but if you’re careful and patient, you’ll learn a lot. I may revisit it in the future but for now, I’m off to start working on my first app on my own.

What’s your experience with learning Rails? Do you have anything to add to my thoughts on RoRT? Would love to hear it in the comments.

FOOTNOTES

[1] This is possibly an unfair comparison because Treehouse is a paid product but RoRT is free. There is a screencast version you can pay $125 for which might provide more of that context, but I was just using the online version. On the other hand, most people who recommend RoRT are recommending the free online version, not the screencasts.

Related Posts:

• Learning to Code: Lessons from Building a Rails App with Treehouse
• When Software is Eating the World, You Better Start Making Dishes
• Startup Founders: Don’t Forget to Sell the Dream
• Ignore the critics: Lean In should be required reading for everyone, including men
• My First Screen iPhone Apps as of November 2012

Since the company was acquired earlier this year, I’ve decided to port this post over and share it with you guys. Hope you enjoy it!

Photo: My father reunited with some of his old friends

My father was born in China as the middle of three brothers. His father rose through the ranks in the local college to become the Dean of Foreign Languages – the only one without a PhD. When he was 16, the Cultural Revolution occurred and young people everywhere were sent to be “re-educated” in rural China.

My father spent his later youth and early adulthood living and working on essentially a rice farm with his brothers. They woke up at dawn, worked in the fields, ate giant bowls of white rice and slept in shacks. Sometimes they would man a concrete boat that carried a massive load of manure on a two-day trip down the river to sell in the market. My father and his brothers would eat and sleep on literally a floating pile of cow dung.

The years went on. Some of my father’s friends lost hope of ever returning to the city and married village girls to settle down. But my father believed things would turn around. Instead of playing cards at night, he would read books and study English. Eventually he got a job as a teacher in a village school and no longer had to work in the fields.

My father’s father worked hard to influence the right people in government and the eldest brother was brought back into the city. Then the youngest. And finally, ten years later, my father returned to his hometown at the age of 26, where he entered college with very little formal education for a decade.

He graduated college, married my mother and bore a son, me. Soon after I was born, he was applying to graduate programs and received a scholarship to study at Boston University’s Graduate School of Education. He moved here, my mother and I followed a year later. We built a new life in America.

Whenever we ran into a hard time, or whenever I’d complain about something, whether it be doing my homework or missing out on a TV show, my father always had a different perspective.

Life was wonderful. We were healthy, happy, had a roof over our heads, clean beds to sleep in and fresh, tasty food to eat. We did not spend days sleeping on a boat filled with feces.

As I’ve gotten older, I’ve really come to appreciate his perspective. In comparison to his youth, day to day life in middle-class America seems like paradise. I’m now about as old as my father was when he left the farms and I now understand, there really is nothing to complain about.

Related Posts:

• Winning Isn’t Normal
• How to Avoid the Emptiness of Delayed Gratification
• Rebounding from Setbacks: a step-by-step guide
• Why I Started Using Tumblr Again
• Twelve Life Lessons Learned from Burning Man

This summer, I’m taking it one step further, by publishing a Kindle book.

Folks on my Insider’s List heard about it a few weeks ago, and now I’m making it official. Winning Isn’t Normal is a hand picked collection of 30 of my absolute best posts, revised and polished to perfection. Plus, I’m writing exclusive all new content that’s never been published anywhere.

You can see a table of contents here.

Introducing AgentFin

Now on top of all that awesomeness, I’m  excited to announce I’m collaborating with Alexis Finch, UX strategist and sketch note extraordinaire, to make Winning Isn’t Normal an illustrated book.

Yep, we’ll be making graphics/illustrations that reinforce and expand on the content. Bringing a visual element is great because not just because the book will look nicer, but because the message will go deeper. Research has shown how illustrations + captions can be even more effective at teaching concepts than verbal summaries, and so these illustrations are really going to make a difference.

I first met Alexis as Ignite speakers (me on Rejection Therapy, her on How to Draw a Dinosaur). She’s been rocking the UX world for quite a few years now as a mentor, researcher and strategist. In addition to sketchnoting folks like Dave McClure and Steve Blank, Alexis is just coming off a project with Mike Rohde (the illustrator behind Rework). She brings an awesome new angle to this book project and I’m honored to collaborate with her.

If this is getting you excited, why not get a discount on the full price of the book by preordering now?

Check out some of Alexis’s work below at at graphitemind.com. You can also follow her on Twitter at @agentfin.

Sketches of yours truly!

Aaron Levie Talk at TwiloCon 2012

Related Posts:

• Use This Navy SEAL Technique to Virtually Guarantee Victory
• Startup Founders: Don’t Forget to Sell the Dream
• Ignore the critics: Lean In should be required reading for everyone, including men
• Why “figuring it out after thirty” is a terrible idea
• How to Be Charming: Highlights from The Charisma Myth

I recently finished Sheryl Sandberg’s new book, Lean In: Women, Work and the Will to Lead. [1] Everyone from the New York Times, Slate, TIME and a host of bloggers has weighed in on Lean In — and many of the reviews are quite critical.

Among other things, people have said it blames women, offers unrealistic advice from a wealthy elite, and dismisses stay-at-home moms.

Ignore the critics. They’re wrong and they’ve missed the fact that Sandberg has produced a powerful book that should be required reading. [2]

Incidents like the disastrous PyCon/Adria Richards debacle underline the fact that some men have little understanding of the unique difficulties professional women face, and some female professionals have struggled to find effective ways of dealing with these challenges. We need to bring more constructive voices to the table discussion. Lean In is a nuanced and highly relevant read for anyone who cares about building a more equitable world in tech and beyond.

A short summary

Sandberg is a total badass, and yet she has struggled with significant hurdles to achieve professional success. Many of these struggles were with confidence, advocating for herself and balancing competence with likability, as well as overt sexism. I was forced to reconsider how to evaluate outward appearances of confidence between men and women and recognize there are no simple answers for ensuring a meritocratic workplace.

Sandberg cowrote Lean In with Nell Scovell, a professional writer, and acknowledges the help of many experts in refining her arguments. The collaboration made for writing that’s leaps and bounds above your typical business-buzz-book fare: paragraphs flow well, stories contain appropriate detail, research is cited and explained.

In the rest of this post, I’ll share some highlights, but I seriously encourage you to read the book for yourself.

More women in power

Sandberg makes the mission of her book very clear. She wants to see women in board rooms and the halls of Parliament, running companies and nations.

In the first chapter, she recounts hosting a dinner party for Leymah Gwobee, the winner of the 2011 Nobel Prize winning activist. Gwobee had helped lead women’s protests that toppled the dictatorship in Liberia and was asked what the best way to help her people and fight the mistreatment of women.

Her answer: “More women in power.”

Sandberg writes this book from a moral imperative. She wants to help ambitious women succeed, not just for their own sake, but to bolster the conditions of women across the globe.

Sitting at the Table

A phrase that frequently appears in Lean In is “sitting at the table.” Sandberg recounts a story of hosting a number of Silicon Valley executives along with Tim Geithnier, the Secretary Treasurer, and his staff at Facebook. While all the executives sat at the main table, Geithnier’s all-female staff seated themselves in chairs along the side of the room.

Sandberg was surprised and waved them over. They demurred and refused to “sit at the table”. Women often are unwilling to jump into the action, Sandberg claims, and this holds them back from moving their career forward and making their voices heard.

She says this not disparagingly from up high, but from the perspective of a woman who has sat on the sidelines herself more than once, and often feels doubts about her position as one of “the most powerful women in the world.”

Confidence versus Caution

There seems to be a disparity in how men and women value their abilities and approach job hunting. According to data from recent graduates at Northwestern, males were 8x more likely to negotiate their salary than women. At Hewlett-Packard, an internal report found that while men apply for open jobs if they think they meet about 60 percent of requirements, while women are more cautious and won’t apply unless they think they meet 100 percent of the criteria.

In the book, Sandberg shared her thoughts on negotiating once she received her COO offer from Facebook:

“My husband, Dave, kept telling me to negotiate, but I was afraid of doing anything that might botch the deal. I could play hardball, but then maybe Mark would not want to work with me. Was it worth it when I knew that ultimately I was going to accept the offer? I concluded it was not.” [3]

In discussing this post with a former female coworker, she told me how one time, after receiving a generous offer from a new employer, she made the decision to negotiate. However, her own mother actually tried to dissuade her from negotiating, saying “It’s already a such a high offer! Don’t push it!”

Ultimately she negotiated a better offer and accepted the position (woot!), but I thought this was a poignant example of how women are often discouraged from negotiating — a message rarely given to men.

Competent women lose points on likability

Sandberg cites a tremendous wealth of research around gender bias: the most memorable example is involved a real-life business case study about a take-charge entrepreneur/venture capitalist named Heidi Roizen. In 2003, some Columbia business school professors had their class read the case study, but half the students got a version of the case with “Howard” switched for “Heidi.”

When polled, students found both Heidi and Howard equally competent, but Howard appeared to be a more appealing colleague. Both men and women felt that Heidi was more selfish and “not the type of person you would want to hire or work for.” This is a very clear example of gender bias: the students read the exact same case!

“When a woman excels at her job, both male and female coworkers will remark that she may be accomplishing a lot but is “not as well-liked by her peers.” She is probably also “too aggressive,” “not a team player,” “a bit political,” “can’t be trusted,” or “difficult.” At least, those are all things that have been said about me and almost every senior woman I know.”

When you want to become C-level executive, having the support of your peers is crucial, and we must be aware of how competent women lose points for likability. This is the double whammy that makes it hard for women to advocate for themselves: because they’ll be docked points for seeming “too aggressive”.

When Sandberg finally did negotiate with Zuckerberg around her offer, she did it in a friendly manner, emphasizing that as COO, she would be doing Facebook’s deals and of course needed to demonstrate her ability to be a good negotiator.

Forming truly equal partnerships

“I truly believe that the single most important career decision that a woman makes is whether she will have a life partner and who that partner is. I don’t know of one woman in a leadership position whose life partner is not fully— and I mean fully— supportive of her career.”

To get more women into power, they shouldn’t have to decide between raising families or advancing careers. [4] There has to be a way to do both.

On this point, Sandberg wants women to ask for truly equal partnerships (if they have a partner) and for men to respond and deliver on an equal partnership. In households where both men and women work full-time, women still do 30% more housework and and 40% more childcare than men. It is unsurprising then that women might feel more burdened by their jobs and struggle more professionally, as they just have a higher total workload than men.

And just in case you feel annoyed by Sandberg’s wealth and ability to hire nannies, note this anecdote:

“When I went back to my job after giving birth, other working mothers told me to prepare for the day that my son would cry for his nanny. Sure enough, when he was about eleven months old, he was crawling on the floor of his room and put his knee down on a toy. He looked up for help, crying, and reached for her instead of me. It pierced my heart…”

Being a working mom is hard, no matter who you are and while Sandberg has lots of money, it does not buy her unlimited maternal bliss.

Closing Thoughts

This book covers a lot of ground: Sandberg also discusses mentorship, taking initiative, seeking growth opportunities, stay at home dads, and a host of other topics. I’ve just scratched the surface with this blog post. I especially encourage men to read it because even if you think you’re “gender-neutral” [4] , I bet this book will led you to change the way you do things.

Here are some very unflattering examples of how Lean In has been relevant for me:

• When discussing the business career prospects of a girl I knew growing up, I made an offhand remark that “it probably doesn’t hurt that she is an attractive Asian female.” I’m mortified those words escaped by lips, but even more disappointed that this line of reasoning made any sense even in my head.
• When having a coffee meeting (not a date!) with a female I had previously only talked with online, I found myself wondering if the meeting was going well because she wasn’t smiling or sharing very much. Then I wondered if I would have the same concerns if I was meeting with a man. Probably not.
• When I’m in conversation with any group that includes women, I am much more cognizant of how often I interrupt/talk over men vs women.

Lean In is an important book that should be read by men and women, in tech and beyond. Having more women in power will help unlock the abilities and contributions of a significant proportion of society that is often under appreciated. And making sure that talent surfaces and worthy ideas are heard is good news for all of us.

Thanks to Winnie Kao, Christine Yen, Margot Leong and Kat Li for reading drafts of this and Christine Lan for helping shape my thinking on this subject.

Footnotes

[1] This is an affiliate link. If you buy this book on Amazon, I’ll get a few cents.

[2] To address those claims directly:

• Blaming women: Sandberg acknowledges there is a chicken-and-egg issue with gender inequality, with external barriers and internal ones. As a woman who’s struggled with these internal barriers and an executive who’s seen hundreds of women struggle as well, she’s chosen to focus this book on the internal ones, without denying there are significant societal problems that prevent gender equality.
• Unrealistic advice from a wealthy elite: while it’s true that Sandberg has more money, power and connections than your typical working woman, she routinely discusses her own struggles before she became one of the most powerful women in the world, and she also shares stories from younger, “more typical” women she’s mentored and how they’ve leaned in. Additionally, she shares some of her more recent struggles of being a professional and a mom. In my opinion, the fact that Sheryl-fucking-Sandberg, the TED-talking COO of Facebook, still sometimes cries at work over issues that probably relate to her gender go a long way in underscoring the far greater difficulties that “regular” working women must overcome.
• Dismisses working moms: simply not true. First she says she’s grateful to the many volunteers, who are mostly mothers, that sustain our schools, nonprofits and communities, and calls for working mothers to “regard mothers who work inside the home as real workers.” She describes many of the painful the trade-offs she’s made as a mother in order to work full-time and recognizes it’s not a path everyone would want to choose.

[3] Sandberg ultimately decided to negotiate only after her brother-in-law made a striking point about how no man at this level would ever accept the first offer. [4] Sandberg makes it clear that not every woman wants to be a working mom, and that some people find full-time motherhood deeply fulfilling and she honors that. She does point out though that the more you can achieve before stepping away to bear your child, the more likely you’ll want to return to the workforce because you could have an exciting career lined up.

[4] Actually, people who claim to have no bias are actually more likely to be biased, according to research Sandberg cites in Lean In. So people who think they’re gender-blind may need this book the most.

“When evaluating identically described male and female candidates for the job of police chief, respondents who claimed to be the most impartial actually exhibited more bias in favor of male candidates. This is not just counterproductive but deeply dangerous.”

Related Posts:

• Two Mindsets to Adopt at Work and in Life
• Cronyism is alive and well (or why relationships matter)
• Book Notes on [Good Strategy / Bad Strategy]
• How to Overcome the Naysayers and Get People to Buy-In [art of buy-in 2/3]
• Why do some people almost always get their ideas shot down? [art of buy-in 1/3]

I’ve never been a particularly fast runner and even after training for and completing a marathon, I’m still pretty slow. So my March Fitness Challenge is a single mile.

A mile is 1609 meters, about 30 feet more than 4 laps around a standard track, which is 400m on the inside lane. I did my test run on March 1st and surprised myself by running it in 6m 50s. My friend Jason Evanish, who ran cross country  in high school and ran something like a 4:45 mile, gave me me some tips on training for a fast mile. Maybe not revolutionary stuff, but as someone used to training shorter distances, it was helpful:

• Intervals workouts: run 1 laps at the track at your goal pace (mine is 6min, so slightly under 1:30 for the single lap). Repeat 4-8 times, with a few minutes of rest in between. Last one should really hurt. Once or twice a week.
• Longer runs: 4-5 mile runs, don’t worry as much about time, just get some endurance in
• Fartleks: Swedish for “speed play”, this is something inbetween intervals and long runs, a mix of easy running, with bursts of faster pace interspersed. I’ve read a lot about these and need to actually try doing them
• Swinging arms: it’s important to swing your arms straight forward and not cross your arms across your body, which wastes energy. Also, swing your arms back hard enough that your hands meet your hips. This opens up your chest so you can breathe better.

I’ve been trying to follow his advice and also modifying my workout routine a bit: doing heavy lifting only one time a week, down from two (which helped for improving handstand pushups) and doing moderate biking on the days I don’t run or do track workouts.

The month is already over half over so we’ll see how it goes. I’m hoping to crack a 6 minute mile. Let me know if you have any other tips or advice for me in the comments.

Edit – Final Mile Time

So I finished my mile challenge with about a 20 second drop, from 6:50 to 6:30. I was hoping to drop it further, to the low 6 minutes and perhaps even break into 5, but it was not going to happen.

The day was a little cool and I wasn’t feeling my best, but you just gotta make the most of testing day. Was definitely wiped at the end. My friend Jason tells me a 20 second drop is pretty good for a month, probably because when you’re training a ton like he was, you didn’t see drops that big, that quick.

Anyway, here it is!

Related Posts:

• Introducing The Monthly FitChal (Max Sit-Ups Pre-Training)
• FitChal #5: Max Pull-Ups + What Happened in April
• FitChal #2: Max Handstand Pushups (Final)
• FitChal #2 Start: Max Handstand Pushups
• FitChal #1 Finale: Max Sit-Ups in 1 Minute