Three wise, wonderful, curious things I read this week - Feb 16, 2018


For many of us, daily life suffers from a profound lack of creativity, inquiry and reflection. The demands of working, commuting and simply living in the 21st century make it tough to find even a quiet moment, much less the time needed for deeper thought.

While I can't offer you more hours in a day, I can invite you to make a little space within your regular comings and goings to engage with some interesting ideas. Here are three things I read this week that sparked my sense of curiosity, wonder and wisdom.

1. Your company's Slack is probably sexist 

"Age, experience, and hierarchical position undoubtedly influence digital behavior. Does gender influence our office’s electronic communications? When I began asking my colleagues, nearly every woman said yes. Overwhelmingly, men said no."  Read more.

2. Where did Valentine's Day start? Lupercalia: Rome's most bizarre spring rite

"While Valentine’s Day has become a fun, commercialized, slightly silly holiday dedicated to candy, cheesy TV specials, cards, and overpriced romantic dinners, the origins may be wilder than anything we would imagine. It is inevitable that holidays evolve, and customs change, but how severely they may do so is variable. The story of Lupercalia and Valentine's Day may show how a holiday can retain the same themes over 2,000 years and do a complete 180-degree turn on how those themes are expressed and celebrated. "  Read more.

3. The tech bias: why Silicon Valley needs social theory

"Silicon Valley tech companies draw on innovative technical theory but have yet to really incorporate advances in social theory. The inattention to such knowledge becomes all too apparent when algorithms fail in their real-life applications – from automated soap-dispensers that fail to turn on when a user has dark brown skin, to the new iPhone X’s inability to distinguish among different Asian women." Read more.

Photo by Aradhika Sharma

A helpful question when you’re afraid to hope for too much


I spent a lot of my early adulthood doing my best to avoid disappointment. I had big dreams for how I wanted my life to be, but I was afraid of them. Even as I imagined a life full of writing, romance, world travel and grand adventures, I was afraid to hope for too much.

I set low expectations for what I could achieve, both to myself and other people.

I undersold my talents, lest my friends and colleagues discover I was an imposter all along.

I hid my vulnerabilities fiercely, lest someone find and exploit them.

I tried not to get too invested in my dreams, lest fate come down and remind me I didn’t deserve them.

I lived by phrases like, “Underpromise, overdeliver,” and “Keep your expectations low. That way, you’ll never be disappointed.”

I spent so much precious time and energy doing everything I could to avoid the pain of disappointment.

I think we all do this. The sting of disappointment is, somehow, one of the hardest parts of being human.

As part of my 30-day journaling challenge, I was journaling recently about my relationship with myself, and I was thinking about the ways, even now, I try to manage my own expectations and protect myself from disappointment. I found myself wondering about this.

I found myself wondering why we — all of us — try so hard to avoid disappointment. Why does it sting so much? Disappointment need not crush a person, after all. It will hurt, and we will get through it, and one day, we might even look back and feel some gratitude for what we learned from the experience.

It seems to me that the bigger challenge has to do with expectation, and specifically what we expect of ourselves. So much of my own fear of disappointment has come from my unwillingness to let go of my own unreasonably high expectations for myself.

Expectations that demand perfection on the first try. That insist anything less than overnight success is complete failure. That see any sign of struggle, any small error, any show of vulnerability as undeniable truth that I do not measure up.

Oh, the suffering we needlessly create for ourselves!

I wonder if it isn’t so much the fear of disappointment as it is our impossible expectations that keep us from daring to live more fully. Disappointment itself isn’t really so bad. But when we treat the experience of disappointment as proof of our own innate not-enoughness… well, then things start to get interesting.

What would it look like to dare without expectation? How might that change our relationship to what is possible?

I’ll leave it there. Sometimes a question is more powerful than an answer.

Three wise, wonderful, curious things I read this week - Feb 9, 2018


For many of us, daily life suffers from a profound lack of creativity, inquiry and reflection. The demands of working, commuting and simply living in the 21st century make it tough to find even a quiet moment, much less the time needed for deeper thought.

While I can't offer you more hours in a day, I can invite you to make a little space within your regular comings and goings to engage with some interesting ideas. That's why I'm starting a weekly roundup of articles, art, ideas and other things that spark my sense of curiosity, wonder and wisdom.

Here are three things I came across this week that I especially enjoyed.

1. Why Hiring the Best People Produces the Least Creative Results (Aeon Magazine)

Complex systems, political science and economics professor Scott E Page argues that building teams for diversity, not meritocracy, is the best way to solve complex problems. Read more.

2. Why Do So Many Managers Forget They're Human Beings? (HBR)

Somewhere along the way, being human at work became a radical act. While the suggestions in this article are far from radical, they're an excellent starting point for leaders who want to bring more humanity and authenticity to their leadership. Read more.

3. A Stoic’s Key to Peace of Mind: Seneca on the Antidote to Anxiety (Brain Pickings)

Anxiety has been a constant companion throughout my life, and it seems to be a mainstay for many in the 21st century. I find Seneca's wise words on the subject tremendously comforting, not only for their wisdom but for their reminder that anxiety is a very human experience, not unique to any single person, time or event but a broadly shared and very human experience. Read more.


What are you reading that's made you a little bit wiser? Head on over to Facebook and let me know!


Leadership rule #2: Diversity and inclusion are not optional

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This is the second article in a 10-part series on what it means to lead effectively in the 21st century. Read the whole series here.

There was a time when you could pay lip service to the importance of diversity, promote a token minority or two into management and otherwise ignore the issue entirely, yet still be lauded as a great and transformational leader. That time has passed.

If you want to be a great leader in the 21st century, diversity and inclusion are not optional.

I don't just mean you can't afford to ignore the ample evidence showing that diverse teams foster more innovation, make better decisions and are overall more profitable. I mean that even if you did want to ignore all the research-based arguments for diversity and inclusion (which would be a very bad idea), you don't get to ignore the moral imperative.

You don't get to occupy your position of privileged, salaried comfort and look down on people who didn't have access to the same opportunities you had. You don't get to boast about "meritocracy" when your company systematically excludes large swaths of people from advancing. You don't get to complain about a lack of diverse job candidates when you only source from Stanford and the Ivy Leagues. And you don't get to treat diversity as a matter of checking off boxes while doing nothing to address the underlying structures and privileges that got us here in the first place.

In the 21st century, this is not what it means to lead. 

Real leadership means being unafraid to tackle hard problems without obvious solutions. It means having the moral backbone to do the right thing, even when it is not the fastest or easiest or most popular thing. It means having brutally honest conversations about where we are now, how we may benefit from a system that oppresses others and how leaders in particular can use our positions of privilege to advocate for greater fairness and justice.

Above all, real leadership means recognizing that there is no rising tide unless we are that rising tide.

A management philosophy called radical candor--which author and entrepreneur Kim Scott describes as "the ability to Challenge Directly and show you Care Personally at the same time"--has been catching on in leadership circles this past year. In-the-know leaders fawn all over it as a way to build trust and collaborate more effectively. That doesn't go far enough. 21st century leaders must be willing to look in the mirror and apply some radical candor to their own organizations' roles in perpetuating exclusion and inequality.

So let's have a radically candid conversation about diversity and inclusion. Let's talk about what it would really take to remake organizational cultures so that they break down, rather than uphold, barriers of privilege.

I'll go first.

  • Eliminate the Bachelor’s degree as a blanket precondition for employment.
  • Get rid of unpaid internships.
  • Do a salary review for everyone on your team. Immediately fix unjustifiable pay inequities. Then implement pay transparency so it never happens again.
  • Offer full benefits to part-time employees.
  • Ruthlessly examine your own biases. Go beyond the obvious. For example, age, weight and class discrimination are rampant, yet far too often, they go unchallenged.
  • Radically rethink your hiring strategy. Rely less on LinkedIn and your existing network. Instead, look at job fairs, community colleges, night school programs, non-profit outreach programs and minority professional groups. I can personally recommend YearUp.
  • Actively recruit people with stigmatizing work histories, i.e. long employment gaps, criminal records, stints of homelessness, addiction struggles, you get the idea. You just might find they become some of your best employees.
  • Hold company leaders accountable for diversity and inclusion goals. Add them to the company dashboard along with sales, marketing, product and all your other business goals.
  • Implement paid family leave. Make it safe to actually take it.
  • Embrace remote work and flexible schedules. Again, make it safe to actually take advantage.
  • If you're a startup, offer your employees the same preferred stock options that you offer to investors, even if that means less financial gain for you.
  • Survey employees anonymously, and ask them three things: 1) How well does your work support your ability to live your life? 2) How often do you feel valued, respected and welcomed at work? and 3) What else could we be doing to ensure that all employees can be at their best while they're here? 
  • Take harassment seriously. Don't minimize or dismiss complaints. Do investigate them respectfully and fairly. Employees have a right to feel safe at work.
  • Thank your employees. Thank them often and genuinely. They're the ones who are keeping you in business, after all.
  • Take a leaf out of Dan Price's book and pay every employee at your company at least $70k per year.
  • As a leader, speak out against inequality and unfairness when you see it. Use your privileged position to advocate for those less fortunate than you in your company and your community.

Set the example. Whether you're a new manager or the CEO, show the rest of your team that you practice what you preach. Embrace a flexible schedule yourself. Go out of your way to source candidates from non-traditional backgrounds. Hold other leaders accountable for the standards you wish to set. In other words, be the rising tide.

If these suggestions sound hard, unpopular and politically risky, well, they are.

They will make a lot of people angry and uncomfortable. At some companies, they might even get you fired. That's why great leadership in the 21st century demands a tremendous amount of courage.

Start where you are, do what you can and trust that your actions matter.

It won't be easy, but it's the only path to lasting change. Even (especially) if your company is filled with dysfunction, one person's ability to rise even slightly above it can make a huge difference in the lives of other people.

You don't have to do it all, but do something. Doing nothing is not an option.

In corporate America, leaders eat first


We love to glorify the importance of leadership in corporate culture. Great business leaders — Richard Branson, Jack Welch, Peter Drucker, Warren Buffett — take on an almost god-like status, every word they speak treated like the proclamations of a prophet.

Yet in spite of our obsession with the power of great leadership, corporate culture as a whole suffers from a profound lack of it (I suspect these two observations are related).

Simon Sinek, another leadership demi-god of our corporate age, famously said, “Leaders eat last.” I was lucky enough to see him speak at the annual ATD conference last year. I didn’t agree with everything he said, but I appreciated his willingness to speak truth to power about the sorry state of leadership in the corporate world today. Everyone applauded at his theories of great leadership. No one applauded at his searing practical critique of the finance industry leaders who got us into the mess of the Great Recession (though I saw several well-dressed executives shift uncomfortably in their seats). Damn, I wish I’d clapped then.

Because the truth is that most leaders don’t eat last. They eat first.

When a company needs to cut costs because of poor decisions at the top, front-line employees tend to be the ones who disproportionately lose their jobs. When a company does well financially, wealth tends to disproportionately accrue to investors, shareholders and executive bonuses, not the aforementioned employees whose labor created that wealth.

Leaders eat first, even kind, well-meaning leaders who genuinely do care about their teams, because the system is designed to feed them first. I’ll never forget the first time I truly understood this. I was at a company leadership team offsite, sitting around a table with the rest of my executive team making “important business decisions.”

And I realized that if we fucked up, if our strategy was totally wrong and we had to change course, we probably wouldn’t be the ones to lose our jobs. We wouldn’t lose the ability to feed our families against our will. Other employees might. But we would eat first.

Maybe I’m being unfair. People, even leaders (especially leaders), make honest mistakes. Economic downturns happen. The world changes, and business must change along with it. This is all true. And it is also still true that when these unfortunate events occur, frontline employees almost always suffer more. Leaders eat first.

So what does this mean if you’re the sort of leader who wants to eat last, who believes in servant leadership and cares deeply about doing the right thing by your people?

I tried to be this kind of leader for my team. I don’t know how well I succeeded, but I learned a few things along the way:

  1. You’ll be uncomfortable a lot. You’ll find yourself advocating for positions that could potentially lead to fewer profits or greater inefficiency because you believe it’s what best for your company’s people rather than your company’s bottom line. When there’s a clear money-making idea on the table and you’re trying to make a moral argument against it, it’s a mentally tough place to be.
  2. Sometimes, the right thing to do and the “right thing for the business” are very, very different. When this happens, you must ask yourself, what kind of person do I want to be? Who do I want to see when I look in the mirror every morning?
  3. Just because something is legal doesn’t mean it isn’t a shitty thing to do. I ran into this a lot in digital marketing. It was perfectly legal to spam the heck out of our email database (as long as you provided a link to unsubscribe), retarget them with creepy ads that followed them everywhere across the Internet, collect a ton of data without their consent, cross-reference it with other data collected without their consent, and use it to serve them even creepier retargeted ads (ahem, I mean relevant, timely, personalized content), all in the name of selling them more shit they didn’t need. Legal? Yes. Shitty thing to do? Also yes.
  4. At some point, you will be asked to cross an ethical line. When (not if) this happens, you will have a very difficult choice to make. I’m not here to judge. Maybe you can’t afford to lose your job. Maybe the opportunity for personal gain is too high. I will just say, decide which lines you’re willing to cross to keep your job, and decide which ones you aren’t. Then draw them. Not in sand. In cement. Because at the end of the day, you have to be able to look at yourself in the mirror every morning.
  5. When it’s possible, do your best to eat last. It won’t always be possible. Sometimes, decisions will be made even further above you that reinforce your privilege within the hierarchy. But sometimes, it will be possible. Sometimes, you can sacrifice a new headcount on your team to save a job on someone else’s. Sometimes, you can take the heat for a subordinate’s mistake. Sometimes, you can advocate for an unpopular position. Sometimes, you can even win.

I guess that’s my final point. In today’s corporate culture, trying to be a leader who eats last will always feel like an uphill battle. It’s a feature of our current system, not a bug. I know that sounds discouraging, so I’ll leave you with these words of encouragement:

If being a leader who eats last feels like a constant struggle, it means you’re doing something right.