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Why Meanness Fails, What Tools are For, & The Value of Contemplating Death

Resource: Mean People Fail

“there are at least big chunks of the world that mean people don’t rule, and that territory seems to be growing.”


Being mean has multiple disadvantages. Since you don’t do your best thinking when you’re fighting, being mean hinders creative thinking while still draining you of energy. Being mean also makes it difficult to hire the best talent since people will only work for you because they have to. And the best talent usually have more options than that.

The most successful startup founders are usually driven by something much deeper than money (ie. improving the world) and they are typically not mean.

The best way for startups to win is not by attacking or arguing, but by racing ahead to the next innovation or opportunity. Successful startup leaders see fights as distractions and delays.

Instead of fighting over a scarce resource, focus on building something new. It’s better to create than compete.


On the rarity of seeing success and meanness combined:

“It struck me recently how few of the most successful people I know are mean. There are exceptions, but remarkably few. Meanness isn’t rare. In fact, one of the things the internet has shown us is how mean people can be. A few decades ago, only famous people and professional writers got to publish their opinions. Now everyone can, and we can all see the long tail of meanness that had previously been hidden. And yet while there are clearly a lot of mean people out there, there are next to none among the most successful people I know.”

Your brain is not in an optimal state when fighting:

“You never do your best work in a fight, because fights are not sufficiently general. Winning is always a function of the situation and the people involved. You don’t win fights by thinking of big ideas but by thinking of tricks that work in one particular case. And yet fighting is just as much work as thinking about real problems. Which is particularly painful to someone who cares how their brain is used: your brain goes fast but you get nowhere, like a car spinning its wheels.”

How startups win:

“Startups don’t win by attacking. They win by transcending. There are exceptions of course, but usually the way to win is to race ahead, not to stop and fight.”

Why being a mean founder hurts your ability to find great talent:

“Another reason mean founders lose is that they can’t get the best people to work for them. They can hire people who will put up with them because they need a job. But the best people have other options. A mean person can’t convince the best people to work for him unless he is super convincing. And while having the best people helps any organization, it’s critical for startups.”

On benevolence as a major advantage:

“if you want to build great things, it helps to be driven by a spirit of benevolence. The startup founders who end up richest are not the ones driven by money. The ones driven by money take the big acquisition offer that nearly every successful startup gets en route. [1] The ones who keep going are driven by something else. They may not say so explicitly, but they’re usually trying to improve the world. Which means people with a desire to improve the world have a natural advantage.”

The futility of battling for scarcity:

“For most of history success meant control of scarce resources…that is changing. Increasingly the games that matter are not zero-sum. Increasingly you win not by fighting to get control of a scarce resource, but by having new ideas and building new things.”

What drives successful startup founders:

“It’s unlikely that every successful startup improves the world. But their founders, like parents, truly believe they do. Successful founders are in love with their companies. And while this sort of love is as blind as the love people have for one another, it is genuine.”

Resource: No New Tools

“My world is laden with bad tools, because my culture is simultaneously obsessed with productivity and novelty.”

“Consider making a program for people, not a program for a computer. I don’t want a new app to help me do work; I want different ways to think about work so I can get more done. It’s a nuanced difference, but I think it is an important one.”


Tools are are ideological. They express and arise from a very particular way of thinking about how work should be done. In order to effectively use a tool, you have to think about work in terms of the ideology that gave rise to the tool. Hence, the tools we use can shape the way we think for better or for worse.

The need for new tools is overrated. Far more important is the ability to think differently and change behavior patterns. If people’s thinking about life/work/productivity hasn’t fundamentally changed, the addition of new tools will just lead to “bucket recursion” — the process of coping with leaks in you existing buckets by adding new buckets that also have leaks.

Leaks in our thinking are best fixed by new mental models rather than new mechanical models.

Build tools for people, not computers.

Don’t get stuck in the cycle of adopting new tools just for the sake of novelty. If a tool isn’t reducing pain and/or increasing pleasure, drop it and move on.


The problem with being an unscrupulous early adapter:

“You’re moving, but you’re not actually going anywhere, only devising ever-increasingly complex methods to make yourself feel slightly more barfy. You are in a loop de loop of productivity, changing for change’s sake. I made an agreement with myself in January: no new apps on my phone or computer. Don’t do new stuff. Just do your work. Text editor, spreadsheet, email, pencil, paper, Photoshop. OK. That’s enough.”

What tools are useful for, bucket recursion, and how to know you have dress-up tools:

The things we make should either reduce pain, increase pleasure, or do some mix of the two. If you’re really good at goal A, you get a bit of goal B for free. And if you don’t figure out how to do either, you’re playing dress-up. Increasingly, I feel like a lot of my tools are dressing-up as tools, because they don’t offer any savings in time or effort, just slightly different methods to mindlessly shift information from one bucket to the next. And if one bucket has a hole in it, you get another, smaller bucket to catch anything coming out of the hole in the first bucket. This goes on and on with more holes and buckets, and before you know it, you have an intricate network of buckets whose reason for existance is to catch the information you can’t manage in the first place. You are stuck in bucket recursion, adding tools to patch the shortcomings of other tools. Those patches are how you know you have dress-up tools.

Are our tools really making us better?

“There are whole breeds of technology that do the opposite of my stated goals—they increase pain and reduce pleasure. Ignore all the privacy issues of Google Glass, look over the utilitarian hurdles in making a smartwatch seem useful to a normal person. Instead, ask yourself a question: who wants to have perpetually visible email notifications? To me, this sounds more like an anxiety bomb waiting to go off than a tool or toy. No delight, no productivity, just more anxiety medication.”

How tools are ideological:

“What’s interesting about digital tools for information work is how frequently they are born from a specific ideology: someone thought work should be done in a certain manner, they found no tools to support that method, so they set off to build their own tool that presumes their ideology is true and best. Thus, we get another to-do app, Twitter client, or project management app.”

How tools force the mind:

“Everything that’s made has a bias, but simple implements—a hammer, a lever, a text editor—assume little and ask less. The tool doesn’t force the hand. But digital tools for information work are spookier. The tools can force the mind, since they have an ideological perspective baked into them. To best use the tool, you must think like the people who made it. This situation, at its best, is called learning. But more often than not, with my tools, it feels like the tail wagging the dog.”

Instead of building new tools, build people by devising new methods of thinking/strategizing:

So, now I come to the part where I make my plea: no new tools, please. If you are interested in improving how people work, you should devise methods for work, manners of behavior, and methods of decision making. Document your ideology and apply it with existing tools, so nearly anyone can follow along. Why don’t you use our best tool? Language. Increasingly, I feel documentation beats an app if you’re trying to shepherd an idea along. This approach seems to have worked pretty well for David Allen’s Getting Things Done and Josh Clark’s Couch to 5K. Of course there are innumerable apps supporting each method, but the ideas are bigger than an app, so you don’t need to download anything. Buy a notebook or put on your running shoes. Commit to the plan. They are not leaky buckets.

Resource: The Five Invitations: Zen Hospice Project Co-founder Frank Ostaseski on Love, Death, and the Essential Habits of Mind for a Meaningful Life


The theme of this post reminds me of Solomon’s observation that it’s better to attend a funeral than a party because of the transformation of perspective that results from considering our end. When we are near death, whether our own or that of others, we’re open to a different range of possibilities within ourselves.

Death is not waiting for us in the distance. It’s with us all the time and is available at any moment to teach us about life.

To be rescued by love, you have to let it come through instead of waiting for it to come to you.


On how the contemplation of death leads to transformation:

“Dying is inevitable and intimate. I have seen ordinary people at the end of their lives develop profound insights and engage in a powerful process of transformation that helped them to emerge as someone larger, more expansive, and much more real than the small, separate selves they had previously taken themselves to be. This is not a fairy-tale happy ending that contradicts the suffering that came before, but rather a transcendence of tragedy…. I have witnessed a heart-opening occurring in not only people near death, but also their caregivers. They found a depth of love within themselves that they didn’t know they had access to. They discovered a profound trust in the universe and the reliable goodness of humanity that never abandoned them, regardless of the suffering they encountered. If that possibility exists at the time of dying, it exists here and now.”

On death as the ever-present teacher:

“Death is not waiting for us at the end of a long road. Death is always with us, in the marrow of every passing moment. She is the secret teacher hiding in plain sight. She helps us to discover what matters most.”

Rescued by love:

“In the horror of my own suffering, I always had held out the hope that one day someone would rescue me. I had imagined that I would be saved by love coming toward me. Just the opposite. I was rescued when love came through me.”

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