Feb 5, 2013 · 9 minutes

Yesterday morning, archeologists announced that they had unearthed the bones of England’s King Richard III — a fantastic historical find. Those amongst us, who read history or know Shakespeare, were immediately able to identify the warped spine of a hunchback. Turns out it was true. The guy really was a hunchback.

Living during the late Middle Ages and having a hunchback was particularly brutal, because not only was it untreatable, but it also came bundled with an even bigger problem — everyone thought you were an asshole.

That’s right, the pious authorities of both Classical and Medieval society generally agreed that a twisted exterior implied a twisted heart and mind. And King Richard III has been associated with just about every vice imaginable — Greed, pride, envy, lust, and the rest of the Deadly Sins.

He was, at least according to Shakespeare, a living embodiment of vice.

All that being said, I really don’t have a problem with most people being greedy, proud, or harboring lust in their heart. Heck, most of our great entrepreneurs are guilty of at least three or four of the Seven Deadly Sins.

And, so, I’ve decided to put together a new list for the 21st century, especially for those of us who work in office environments. I’ve also avoided the precedent of using one-word sins — I like to be specific with people and describe the exact offense that is being committed by these poor sinners.

If you live and work in Silicon Valley, you will no doubt have encountered all of them, and you will agree that possessing even one of these deadly sins can be a career-destroying vice...

1. Defending your own flaws

This is the granddaddy sin of them all. The single greatest sin a businessperson can commit. If you are the sort of person who embodies this, then your odds of success are basically a shade above nil.

I know a few people who are poster children for this, and they have all ended up deeply disappointed with their careers as a result.

It doesn't matter what the flaw is — poor technical skills, sloppiness, inability to work with others, not showering. There are people who rally behind their own shortcomings, turning their refusal to improve into some sort of mantra.

"I know that I'm not easy to work with, but that's who I am."

“I know that I’m a terrible communicator, but it’s because I work so hard.”

There is no flaw worth defending.

The best people work to identify their weaknesses and improve them. When I was young, I had a lot of issues with my temper. I had trouble working on teams. I was lazy and procrastinated until the night before an exam. It took me years, but one by one I have tried to improve these flaws. Nobody is perfect. But people can improve very quickly when they openly concede their weaknesses and start addressing them.

2. Self-convincing

This is another deal-breaker.

I know a lot of people who somehow manage to convince themselves about, well, pretty much anything that they want to do.

They have a reason for why they are moving to New York abruptly, despite not having a job there or a plan for the increased life expenses. They have a reason for why they are quitting a perfectly good job, when they are only eleven months into it. They have an explanation for why buying that expensive sweater is not a luxury, but rather a necessity.

"Well, I could buy a worse sweater that I barely like, or pay $200 more for one that I love forever. And even though I quit my job last week, I only did it because I know that I'll be able to find a better one when I actually try this time. So I’ll buy this Prada sweater now, and start job searching next week."

These are people who time and time again sit down with a parent, friend, or confidante, to explain what they are "thinking" about doing... only to ignore a tsunami of counter-points. And they stick with their original plan, content that their great idea has now held up to scrutiny.

Ultimately, in reflecting upon six of the most successful years of my life, I had a lot of luck, but I also made three or four outstanding decisions along the way — ones that were at least partially shaped by my father, friends, or co-founders.

3. Being too quiet

This one is easy.

People who are too quiet are doing themselves a terrible disservice. But they are also hurting their company.

They have good ideas that don’t see the light of day. They anticipate stupid decisions, but don’t stop them from coming to pass. They achieve great deeds, but let somebody else share in the credit — or steal it outright. They let smooth-talking douchebags get the promotion over them, and then the rest of us are stuck dealing with that douchebag who is now in a managerial capacity.

America’s education system trains students not to speak up. They reward children for quietly doing their homework on time, following instructions, and performing well on written exams. And then, 10 years later, those children get passed over in favor of the loud self-promoting class bully who didn’t do the reading, but was happy to stand up and claim the spotlight.

As a society, we need to train our children that speaking up in class — even if it is occasionally to tell a joke or question the teacher — is a good thing. Otherwise we are training the next generation of sinners.

4. Over-networking

One of the original “seven deadly sins” was gluttony. And the modern equivalent is “over-networking.”

The parallel is an important one. Everyone needs to eat. No church official will chide a man or woman for enjoying a filling meal. But it’s the excess that turns it into a deadly sin.

Networking is much the same. It needs to happen. It’s healthy in moderation. But some people turn into “career networkers,” who seem to view it as the only major part of their job description. Some of them think that a job in Business Development is their born calling. But the truth is that great Business Development people also work their assess off on contracts, business analysis, implementing the partnerships once they are signed.

There is a lot more to being a great Business Development person than handing out cards at one Tuesday night networking event after another. A person who does that is simply an asshole.

And, most of them don’t even realize how transparent it is. Jokes on them.

5. Indecisiveness

Even a small dose of indecisiveness can cause you a world of pain.

When you hire somebody, and determine two months later that they absolutely aren’t the right fit, then you have to let them go. Letting them linger while you try to “monitor the situation” is like slowly poisoning your own company.

When you have a term sheet from a great investor, but you think that you could sit on it for a few weeks to see if something better comes along...in hopes of avoiding a percentage point of dilution. That’s when the Dow Jones collapses, your term sheet gets pulled, and you lose everything.

When it’s time to pull the plug on an under-performing feature or initiative, but you want to gather another month’s data just to be sure that it’s a dog...that is a great way to squander a month of valuable engineering time.

The examples are endless. But the point is the same. Making quick decisions, as long as they are informed and defensible, is almost always the way to go. Finding the perfect balance between this and Sin No. 2 is the ultimate sign of a great executive.

6. Bullshitting

Telling a lie was something that a person used to get away with — maybe up until 10 years ago.

But in the modern world, it is almost impossible to lie and get away with it. There’s just too much data out there, and if somebody really wants to investigate your claim, they can call you on it 9 times out of 10.

Just watch as Manti Te’o and Lance Armstrong try to cobble together lies and excuses for their bizarre actions. Even a cursory review of archived Tweets shows how many holes there are in the Te’o story. And Lance Armstrong’s efforts to gag his former teammates might have worked in 1985, but not in a world where everyone has a megaphone in front of their face from the moment they wake up in the morning until the moment they go to bed.

Bullshitting was always a nasty habit, but for somebody to do it in the modern day, they have to have an awful lot of chutzpah. So often, they think that their pitiful explanations are being ingested by their straight-faced onlookers, but as soon as they leave the room, they are a walking joke.

Google can untangle just about any Web of lies.

7. Being comfortable

Here is my general opinion on “being comfortable” in life.

The moment you feel that your life is very comfortable, you should figure out a way to make it less comfortable.

Our ancestors warned against sloth in a world where skipping harvest days could lead to Winter starvation. Thankfully, that is not the world we live in today. And it’s precisely because we live in a world of opportunity and aspiration that simply subsisting is not nearly enough. Or shouldn’t be enough for us.

But how many people do you know who have been doing the same job for eight or nine years, with small changes in scope and responsibility, only to begin viewing the world through the lens of “the Accenture way”?

They love making their gainful living with a 3-4 percent raise each year, and earning praise from somebody a rung or two up the ladder is enough to make their day. They actually take pride in those cheesy loyalty awards with the corporate logos on them.

Most of our ancestors survived some form of peasantry or servitude, made it through wars and depressions, and were forced into cross-ocean boats at the end of a whip or in the face of starvation. Sure, they would have loved to live in a comfortable middle-class suburban home with plenty to eat...

...but they also had 10 times the guts and strength that we do in the modern day. The least we can do is honor their memory by channeling one fraction of their fortitude.

Comfort is dangerous. Don’t give into it. Life lasts a long time, and it’s never too late to take risk. If you have spent the last 10 years as a consultant, IT manager, or accountant, then you know exactly which industry is in need of disruption. Now kiss your spouse, and prepare them for the adventure that awaits. It’s time to get your hands dirty. You can always go back if you fail.

[Image by James Ensor courtesy wfu.edu]