The world will try to beat you into mediocrity.

The following is adapted from the Preface for my new book, Winning Isn’t Normal

The world will try to beat you into mediocrity.

We’re pressured into grinding jobs that leave us frustrated and fatigued. Sold into a sedentary lifestyle that turns our bodies into shapeless lumps. Chided into following a pre-determined path of that avoids risk and is devoid of adventure or originality.

The worst part is that the mediocrity often sneaks up on us, dressed as convenience, security, and comfort. So we often don’t even notice it, until it’s too late. Infiltration through obfuscation.

This book is about fighting against mediocrity. And winning.

My eyes were first opened when I read Stephen Covey’s masterpiece, The Seven Habits of Highly Effective People. Pouring through Covey’s lessons – be proactive, private victory before public victory, begin with the end in mind – shaped me as a thirteen year old boy. My perspective and approach to life was changed. profound ways. If this book’s impact is a fraction of a fraction of 7 Habits, I would be overjoyed.

In the following pages, we’ll talk about overcoming our fears, navigating obstacles, pushing through rejection and failure, staying curious, and constantly striving to do things better. We’ll talk about doing things that are difficult and different.

It is with this approach that we do battle with the insidious forces that limit our potential and keep us small.

While I can’t offer you definitive evidence, I want you to know that I do my best to live the values, ideas, and techniques put forth in this book. I certainly don’t have all the answers, and I fail to live up to my own exhortations all the time. And yet, I have strong reasons to believe that this stuff really works. Ultimately, that’s for you to decide.

Every book has a beginning. I’d like to thank Ryan Hupfer for convincing me to start my blog, Sebastian Marshall and Derek Flanzraich for our wonderful writing collaborations, Janet Chang for coming at the eleventh hour with thoughtful edits, and Kai Davis for the conversation that lead to this book.

And of course, I’d like to thank my readers for their questions, ideas, suggestions, and stories. If you’d like to reach out to me about anything, I’d love to hear from you at or on my site,

I hope this book makes you think differently. But even more so, I hope this book makes you act differently. Let’s go do some epic sh*t.

My Book, Winning Isn’t Normal, is Now Available on Amazon

3D Cover Winning Isnt NormalIn the past three years, I’ve put countless hours into The Art of Ass-Kicking. It’s been a lot of work, but also tremendously rewarding, both personally and professionally. More than a hobby, this blog has become an integral part of my life. I write to internalize what I’ve learned, and to share with with you, my readers.

In the early spring of 2013, I was thinking about where I could take the blog next, and after a conversation with Kai Davis, decided to publish a book that represented by best ideas, stories and strategies.

Over the course of many months, I put together a book that spans three major themes: focusing our Minds, strengthening our Bodies, and increasing the impact of our Work. I edited and rewrote thirty-one essays (representing over 50k words), designed a cover and three pieces of original quote typography, recruited Sebastian Marshall to write a foreword, and navigated the Amazon Kindle Publishing program.

Today, I’m thrilled to announce that Winning Isn’t Normal, is now available for download on Amazon as a Kindle ebook.

Note: through October 22nd, there’s also a special giveaway related to the book launch. Scroll down to learn more. Continue reading…

I’m Writing a Book and Alexis Finch is Illustrating It

Editor’s Note: Alexis and I ultimately didn’t work together on this book, but we’re still friends! And the book is out now: get it here!

winning_isnt_normal_cover-2Since fall of 2010, I’ve done my best to help readers kick ass and make things happen, with step-by-step guides, crazy/stupid adventures, slide decks, personal stories, reader contributions, videos and more.

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

alexis finch
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.
Continue reading…

Ignore the critics: Lean In should be required reading for everyone, including men

Disclaimer: as a man writing about gender inequality, I acknowledge my privileged (and biased) viewpoint in this discussion. I’ve run this post by several smart, awesome women and incorporated their feedback, but I know I still run the risk of getting things wrong. Still, this topic is so important that I felt I had to try to add to the conversation.


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.


[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.”

Why “figuring it out after thirty” is a terrible idea

jacketI just finished reading The Defining Decade: Why Your Twenties Matter and How to Make the Most of Them by Meg Jay. My friend Jason Evanish has written about how much he enjoyed the book, but I didn’t get around to it until I had a conversation with Jonathan Gurerra about a few days ago.

The book is written from the perspective of a therapist who has seen many twenty-somethings make good and bad decisions and has been doing her practice long enough to see how those decisions pan out. I’m 26 today (turning 27 in two months) and this book is very relatable, with detailed conversations between the author and her clients that will definitely sound familiar.

Her basic points are this:

  • The idea that our 20′s are just a time to fool around, find ourselves and delay the real-world till 30 is a myth
  • Twenty-somethings need to be deliberate about their choices – what work they do, who they love, where they live
  • In regards to work: do something to build “social capital” vs being a barista, even if you’re not sure it’s your “true passion”
  • In regards to love: do the math. If you want to be married with two kids by 35, you can’t keep dating bad-for-you people into your late twenties

I feel that I’ve done pretty well in my career so far. Despite starting work a year later than my peers (I stayed for a 5th year masters at Stanford) and not working at any blue chip companies, I’ve developed a strong set of skills, experiences, connections and assets. The future is by no means assured, but I’m confident my efforts in the working world will serve me well.

Where the book really hit home was in the love/relationships section. I’m currently in a monogamous long-term relationship with a wonderful lady, but I’m not thinking about marriage anytime soon. While I do want to start a family some day, it’s always been something I thought I’d figure out “after thirty”.

But the book makes it clear: things don’t just magically fall into place when you turn thirty. For instance, doing the math: if I want to get married and have two kids in my mid-thirties, how much lead time do I need?

  • 1 year of engagement
  • 1-2 years of childless marriage
  • 3 months (if you’re lucky!) of trying to get pregnant
  • 9 months of pregnancy
  • 1-2 years between children
  • 1 year of trying + being pregnant
  • Total: 5-7 years

So if you want those two kids by age 35, you must be proposing no later than age 30. The math does not lie.

Certainly the timeline could be made shorter, you could cut the engagement shorter or post-marriage childrearing etc, but it could also go in the other direction: the girl you propose to (or marry) doesn’t work out, you have a miscarriage, etc.

Anyway, the author is not advocating that everyone just marry the next person they meet or commit to a corporate stooge job they hate, but she is saying that twenty-somethings need to face the hard truths of reality in order to prepare/choose a future that will make us happy in the long run.

The book is an easy read and pretty short. I finished it in a weekend and highly recommend it for anyone under 30. If you are over 30, I would recommend you DO NOT read it, unless you feel particularly good about how life has turned out, and you want to see what you did right.

You can buy The Defining Decade on Amazon here.

Note: this post contains affiliate links