1% Leadership

1

Personal improvement is a prerequisite to leading professionally.

LEADERS. ROLE MODELS. HEROES. THE WORLD IS FILLED WITH human beings that society and culture teach us we should look up to and emulate. But often to our surprise, we learn that each one of them is imperfect because, ultimately, they are all human beings. Our error is in expecting them to be angelic, and perfect, when, like us, they are merely on a path to becoming different versions of themselves.

Hopefully better versions of themselves. Their flaws are often minor, but the more we idolize them, the more extreme those flaws are to us because we feel let down. Our heroes do not always practice what they preach, or they are forced to make trade-offs that we find uncomfortable. At that point, it is easy to turn away from the lessons they offered us. If their wisdom didn’t work for them all the time, then how could it work for us at all? Phrased that extremely, it sounds absurd, but that is often how we judge others.

Because people often look to follow a path to perfection, that absurd question always hangs over us. In seeking the perfect, we sometimes turn away from the lessons that could help us, the wisdom that may be applicable in some situations, the ideas that we might benefit from.

The uncomfortable truth is that there isn’t a single formula for leadership. There is no “do this right thing” and people will follow you. The first person you need to lead, though, is yourself. If you aren’t able to lead yourself on a journey of improvement, others will have a hard time following your path. When they stumble—and they will stumble, because growth is never seamless—they will need to see that you stumbled, as well. And, more important, that you picked yourself back up and kept improving.

These next essays are all structured around ideas for personal development, but they are ideas that will reflect themselves onto the people around you. Your growth—especially in how you interact with people around you—is the foundation on which your own leadership style can develop. It might be easy to dismiss personal growth as mere self-help, but the people you lead will constrain themselves with your affect. If you never seem to have fun, then, implicitly, you’ve banned fun. If you never acknowledge mistakes, then they fear ever being caught making a mistake. This section is a self-help guide; it’s a set of tools not only to center yourself, but to help you be a more authentic leader.

Some of the tools here will work for you. Some of them have already failed you. But the premise—that leadership begins with you—is the first building block, one that will give you a place to stand before you can move the world. The chapters that follow are short essays on personal leadership, on a way of seeing and understanding the world as you walk through it. Most of the essays are just about how you see the world, a few are on how you interact with others, but together they form a guide that helps you become your better self every day and find the bright spots along the way. It isn’t about being a shining light to the entire world. It starts by being a light to yourself and then to those around you.

Personal improvement is a prerequisite to leading professionally.

2

Your attitude is in your control.

THE WORLD SUCKS.

The world is awesome.

Both of these statements are true.

Even in that paradoxical world, your attitude is in your control.

We simultaneously live in a world that is the most awesome version of the world so far and the most horrible so far. The former is more true than the latter. The world today—at least as I write this, and hopefully still as you read this—does not compare to even the historic everyday horrors of starvation and total abject poverty, let alone global genocides or total wars. But, thanks to the Internet, the world has also gotten smaller, and every day the speed of social media and viral videos leads to new horrors being splashed across our eyeballs and burned into our brains.

The world is imperfect, even as, day by day, more people rise out of extreme poverty, and fewer people are enslaved, and freedoms slowly spread around the world, and education access improves. It’s easy to lose sight of all of these things, especially if you are near a place where they are less true. And every day, your experience is filled with both delights and tragedies, sorrows to rend the soul and joys to lift the heart. How do you deal with that overwhelming emotional experience?

We can choose to not engage in the world, to just put our heads down and pretend that the world today is just as it was every other day in a history we don’t carefully look at. On that path lies apathy, but it’s a clean and simple apathy, for one simply withdraws a bit from the world, experiencing only one’s own private joys and sorrows, except when the world manages to intrude a bit into our isolation.

Or we can choose to be spun up about every outrage, each horror. We can spend our days sharing memes and hot takes on social media and patting ourselves on the back because we spread a little more knowledge of the ill in the world—but at the expense of filling ourselves with anger and spreading that more deeply into our communities. We can be continuously disappointed in our neighbors because obviously they aren’t achieving our ideals and assume they must be vile villains bent on destroying the world. We can hate ourselves for our helplessness in the face of that villainy, to see the cost of action being so high that we can never get to it, worn out from the stress of outrage at ourselves and our neighbors.

Or we can choose grace. We can choose to see the good in the world and, beginning with ourselves, amplify that good. We don’t need to ignore the bad, but, rather, we counter the darkness with our own light. Not a light of fire and destruction, but a light of peace and joy. It’s a harder path, because it is one filled with self-restraint. Like a diet in which we must pass up treats, we must also pass up the rush we get from joining others in righteous anger. We can recognize that we are truly fortunate in ways that most of humanity a century ago couldn’t even dream of and use that serenity to weather the troubles that plague our days.

Those are the paths that lie before each of us. The people around us are influenced by the path they see us choose, even as their choice of path influences us. The paths aren’t always obvious. Our attitude in looking at the world creates the path ahead of us; we can’t always see the path until after we choose it.

Your attitude is in your control.

3

Your blessings exist only if you remember to count them.

A COLLEAGUE OF MINE ONCE ASKED THEIR COWORKERS, “ON A SCALE of one to ten, how fortunate do you feel?” Another colleague immediately said, “Ten. I’m not a nematode.”

Think about it. There are, by some estimates, more than a billion insects on the planet for each human. Five hundred fish. Four hundred trees. And that doesn’t count bacteria, where we have to use scientific notation just to estimate how many exist. Which means that not only are we a ten on a scale of one to ten, but we’re a ten dozens of times over! Even on our worst day, we are still much more fortunate than a bacterium floating in the Sargasso Sea.

But let’s ignore all of the nonhuman competitors for a moment and marvel at how fortunate we likely are, even among all humans. Baseline quality of life of the median human now is better in so many ways than the quality of life of the most fortunate human one hundred years ago: vaccines, the Internet, better infrastructure. We still have improvements to make, but with more than a hundred billion humans ever born, just being alive now rates another ten on a scale of one to ten.

If you’re reading this, you likely have other advantages, too, and great blessings. Perhaps you live in a free and prosperous country. Maybe you have a good job and an excellent family. Possibly you’re brilliant. You have free time. There are hundreds of ways you can be fortunate, and much of that good fortune doesn’t preclude other human beings from also being fortunate.

So that’s where you start: you are an amazingly blessed individual, even with all that goes wrong in your life. But we get a choice as human beings: we can focus on the good or on the bad. Sadly, all too many humans focus on the bad. We find reasons to be unhappy with our situation, or frustrated at the imperfections of the world, and then we forget to treasure our joys.

Perhaps we are too fortunate. Can a person who has never really seen misfortune grasp how fragile good fortune can be? The people who most seem to optimistically cherish life are the ones with misfortunes that break my heart: the refugee from a war-torn country whose parents were left behind, the parent whose child has a mortal affliction, the veteran who carries hidden scars for life. And the people who have lived a life full of advantage often see the world as irreparably broken—the problems they see feel huge in contrast.

And so each day, I like to think about how fortunate I am. When someone asks me how I am, I’ve trained my reflexive response to be “I’m fantastic!” It’s a reminder to myself to make it true, to see the excellence and grace I am blessed with, and to share it widely. Most people laugh or make a joke—but even in the gentle mockery, they smile, because now they feel a little more fantastic themselves.

My wife started a more specific tradition to count our blessings. Each night at dinner, each family member is prompted to share a bright spot of their day. Even on our worst days, we can show gratitude for something or someone. Remembering that those moments exist helps us build a foundation of serenity.

The reality is that we live in a world so full that, almost by definition, it’s a mixed bag of positive and negative situations. Even in a positive or negative situation, it’s easy to find elements that run counter. Maybe you got a promotion, but it didn’t come with quite the pay raise you expected. Maybe you had a bad encounter with your boss, but a colleague gave you words of encouragement.

The world you live in is just the set of situations that you choose to focus on. You can remember all of the bad elements of your day, be convinced that the world is awful and worthless, and respond with frustration and anger. Or you can remember all of the good elements of your day, and be convinced that there is beauty in the world, and respond to nurture and grow that goodness. Your reaction—whatever you choose—then becomes an experience that other people can choose to remember. If you respond to badness with more badness, then you’ll increase the net badness in the world near you, which will come back to rebound on you and those around you.

Your blessings exist only if you remember to count them.

4

Becoming right requires accepting that you might be wrong.

YOU ARE WRONG! CONGRATULATIONS!

I know, that seems a little odd. Why am I celebrating being wrong? Because being wrong comes with some amazing superpowers. First, you get the opportunity to learn something new. It’s really difficult to learn things when you’re already right; it’s in acknowledging that we’re wrong that we usually get the opportunity to learn new things quickly.

Note that being wrong—or, really, failing in some way—isn’t a binary condition. You can succeed beyond your wildest imagination and still find errors that you can improve on. Looking for the ways you were wrong and asking, “How could I do this better next time?”

That’s the boring superpower. The awesome superpower is that you can’t lose an argument when you start out acknowledging being wrong.

That seems weird, doesn’t it? Imagine I started a conversation with “The sky is green today.” That conversation is… not likely to go well. Odds are, anyone I talk to is going to tell me that I’m wrong, that the sky is blue, or gray, or maybe start questioning my choice of pharmaceuticals. Wherever the conversation goes, it’s likely to only frustrate me (since whatever reason I had for starting that conversation is something we’ll never get to) and anyone else in the conversation (because I’m obviously wrong, so why am I starting pointless arguments), and it’s probably a waste of time. But what if, instead, I started out with admitting my own possible error and making a smaller argument?

“I might be wrong, but it seems to me that the sky is a bit green today.” How can someone argue with that? By telling me the sky is blue? I’ve already conceded that point! Instead, I have invited my conversational partner into the real conversation. “Why does the sky seem green to you? What makes you say that?” And now maybe we get into a conversation about the pollen in the sky, or maybe there are cool optical artifacts from the wildfires in California (I’m pretty sure that whenever you’re reading this, there are still wildfires in California). But I’ve invited you past the obvious argument, into a more subtle conversation, and there are only two possible paths: you can quickly agree with me that I’m wrong, in which case I win because not only was I correct in my assessment, but we didn’t waste time arguing. Or you can disagree with me (on my wrongness) and tell me I’m right. It’s very important to not apologize for being wrong at this stage; saying “I’m sorry if I’m being obtuse, but it seems to me that…” creates a distracting signal of weakness in many environments.

The value you take away is tied to understanding your objectives in this conversation. Maybe your goal is just to be right. That’s rarely actually a helpful goal, although you’ll encounter many people who seemingly act as if that’s their primary goal. But if your goal is to move forward a conversation in a specific direction, then you’ve played a form of rhetorical jujitsu; your partner gets to be right, and you get to have the conversation you wanted.

That later piece is really powerful. A lot of people, when involved in a conversation, want to add value to the conversation. For many people, value comes into being when they make a contribution that they don’t think would have been made without their presence. Specifically, they can provide value explicitly by disagreeing with you. “You’re not wrong” is a form of value that they get to provide.

By starting out with an expression of being wrong, their reflexive disagreement actually furthers the conversation by getting into real agreement. Embrace the possibility of being wrong and move on to being more right more quickly.

Becoming right requires accepting that you might be wrong.

5

Even if you don’t succeed, a story about failure can be a reward.

NOT EVERYONE LEADS A CHARMED LIFE. I SUSPECT THAT NO ONE leads a charmed life, even those who, when we peer in from the outside as they count their blessings, seem to. For almost everyone, every day includes some event that goes wrong. Not necessarily horribly wrong. But, nonetheless, things don’t always go according to plan. But when plans fail, you get an opportunity to have an experience. And you might learn something.

It was the year 2000, and I’d just started working at Akamai. Despite being a security engineer, I was tagged to audit a software installation, on a distributed network of a few thousand servers around the planet (a number that feels so tiny now, but this was in the precloud era). Our installation process was fairly simple: The installer would “suspend” a group of one-eighth of the machines, which simply told our load-balancing system to stop sending them traffic. Once traffic had been given time to fall off on those machines, the installer would run an installation script that would mass-install all of the systems in the group. Then the auditor would perform a basic checklist on a handful of machines, make sure they seemed all right, and give the installer the go-ahead to start the next group.

You might notice the absence of a command to “unsuspend” any of the machines. In those days, there were two ways to suspend a machine. In one, you sent a signal to the main application on a machine, and it would tell the rest of the network to stop sending it traffic. When that application restarted, it would “forget” that it had been suspended and come back up, ready to serve traffic. Then there was sticky suspension, where a configuration file was altered on the machine so that when the application came back up, it would remember to tell the network it was suspended. We used sticky suspension for installs that took multiple steps, like updating the operating system, and regular suspension when we were just updating applications.

That night—we always did installs during US nighttime—we were doing a normal software installation. It was my first ever as auditor. The installer was doing his second ever, after doing an operating system upgrade the prior week. They were using the checklist for that installation, which, unfortunately, specified sticky suspension. I, as the auditor, had the checklist for an application installation, which… did not.

By the time we were finishing the fifth group and had just suspended the sixth group, the network operations team called me. They had a giant wall of monitors, and every server was displayed by a small rectangle. The rectangle was gray when everything was normal, yellow when machines were suspended, and red when they were down.

“Andy, there are a lot of suspended machines.”

“I know, we’re doing a software install.” And I hung up.

Ring ring. Ring ring.

“No, Andy, there are a lot of suspended machines. The whole wall is yellow.”

“Uhh…” I quickly pulled up our monitoring system. Yup, 75 percent of the network was suspended.

We stopped our install, quickly figured out and solved the issue, and finished up.

This was not an experience I’d qualify as Type 1 fun (fun you have while doing it). It’s more like Type 2 fun (fun only in telling the story of its horribleness, like running a marathon). It’s easy to take the experience, be upset that it messed up your day (explaining how this had happened to our boss, my colleague getting stuck with the nickname “Sticky”), talk about having a horrible day, and move on.

But in trying to forget about the day, I’d also lose the benefit of the experience. Of learning that human errors result from seemingly simple, but very fragile, complex systems. Of learning not to dismiss a warning from a colleague. Instead, in telling the story, I helped future colleagues see that being the human trigger in a crisis wasn’t necessarily career-ending.

Ultimately, in any activity, either you get an experience or you get a story. And you get to choose how you tell the story. And there is something to learn every time your experience isn’t perfect.

While the learning is valuable, it’s often the story that keeps that learning fresh in our heads; it’s the story that allows us to share our experiences with others in relatable ways.

Even if you don’t succeed, a story about failure can be a reward.

6

Gift kindness where it isn’t expected.

AS A LONG-TERM EXECUTIVE AT A SUCCESSFUL COMPANY, I RECEIVED a lot of attempts from vendors to get meetings with me, as precursors to selling me their product. And by “a lot,” that’s generally dozens every day. These sometimes come as phone calls (there’s a reason I don’t generally answer my phone), but more often as emails. Most of the time, they’re automated, but many of them are handcrafted; a junior sales representative spent a few minutes looking me up on the Internet and has been tasked with getting an appointment for me, often with a more senior sales rep. It’s a thankless task, and getting the deluge of notices can be rage inducing.

I have colleagues across the industry who respond with a level of snark and condescension, and I’ve been tempted to, as well. Usually, I just ignored the messages, even when the