Impossible, or possible?

When you’re told that something is impossible, is that the end of the conversation, or does that start a second dialogue in your mind, how to get around whoever it is that’s just told you that you can’t do something? So, how am I going to get past this bouncer who told me that I can’t come into this night club? How am I going to start a business when my credit is terrible and I have no experience?

~ Eric Weinstein


Step 2

People – especially really smart people – have a tendency to attempt solving big problems (like earning a profit) without first solving more basic ones (like how you’ll get there). This is why the “Step 1, Step 3” joke resonates. And it’s why understanding the hierarchy of earning profit is so important.

~ Morgan Housel from,

Oh, crikey! That’d be me. I too–frequently get frustrated when my “awesome idea” isn’t received the way I’d like it to be. I think it’s exactly the same step–two problem that Housel points out. I’m jumping over step 2. But in cases where I try to figure out step 2… *crickets* It occurs to me that there’s another way to address the issue: Stop chasing ideas that solve a problem that I have, and instead try to chase an idea that solves a problem someone else has.


Interesting jobs

I distinctly remember [my dad] saying not to worry about what I was going to do because the job I was going to do hadn’t even been invented yet. […] The interesting jobs are the ones that you make up. That’s something I certainly hope to instill in my son: Don’t worry about what your job is going to be. […] Do things that you’re interested in, and if you do them really well, you’re going to find a way to temper them with some good business opportunity.

~ Chris Young


What’s the point?

I think many people assume, wrongly, that a company exists simply to make money. While this is an important result of a company’s existence, we have to go deeper and find the real reasons for our being. As we investigate this, we inevitably come to the conclusion that a group of people get together and exist as an institution that we call a company so they are able to accomplish something collectively which they could not accomplish separately. They are able to do something worthwhile— they make a contribution to society (a phrase which sounds trite but is fundamental).

~ David Packard Jr. from,

“Important result,” as in: One way to measure value created is to use accounting, and money is a wonderfully well-understood thing with which to keep account. There are other ways to measure value creation, obviously. But even a not-for-profit company has to keep account of it’s balance; if its income doesn’t balance expense, eventually the creditors will cease extending their services. Everything—people, companies, communities—is somewhere on the spectrum from consumption thru creation, via accounting of value. The magic sauce is our minds. We each use our minds to create value, and we each find a vehicle for taking our ideas to fruition.

Anyway, that’s how I see it.



This, in one sentence, is the difference between the laborer-for-hire and the entrepreneur. This is the Professional Mindset.

~ Steven Pressfield from,

Pressfield’s example—I’m always assuming you’ve clicked-thru and read—is oversimple: the factory worker. But that laborer-for-hire mindset is real. The shift required is real, and really difficult. Hard like: This is the air I’ve always breathed. …and I want to be a fish, so I need to grow gills, get in the water and learn how to swim in water without seeing the water—in the same way I used to be oblivious to the air. That is to say: Impossible.

Morning friends! How’s the air?!


Genius working alone

The team must consist of three sorts of specialists, he says. Otherwise the revolution, whether in politics or the arts or the sciences or whatever, is sure to fail. The rarest of these specialists, he says, is an authentic genius — a person capable of having seemingly good ideas not in general circulation. “A genius working alone,” he says, “is invariably ignored as a lunatic.”

~ Kurt Vonnegut from, Bluebeard

Meta: Copy-paste-and-search if you want to read the entire, surrounding passage. As a creator of content myself, I decline to copy and paste the much longer passage as many others have.

This passage from Vonnegut is brilliant, but it makes me a little nervous. Am I the genius? …or more likely, the lunatic? Perhaps I’m one of the other two specialists. Or worse, I’m not any of the three.


I remember why I keep bourbon on hand.


Nothing Fails Like Success

There are internet companies (like Basecamp, or like Automattic, makers of, where I work) that charge money for their products and services, and use that money to grow their business. I wish more internet companies could follow that model, but it’s hard to retrofit a legitimate business model to a product that started its life as free.

~ Jeffrey Zeldman from,

ahahahahahahahahhahaahahhaaa! Sometimes I like to share stuff just because it makes me happy. (The stuff; not the sharing of said stuff, I mean.) I regularly talk about how this web site is a vehicle for my reflection—I’m quite often literally thinking through things. Writing, (tappity-tap-tapping on the keyboard here,) and writing, (scratchity-scritch-skratching with a pen on paper,) are two of the ways I figure out if the dross I regularly find in my head actually corresponds to reality.

When I read sentences like the ones I quoted above, I leap (sometimes literally) to my feet knocking over my chair in the process. It does my weary—deeply deeply weary it be—heart good just to read sentences like this. And I hope—not in the sense that I little value your ability to think and “hope” you’ll finally get what I’m saying; no. I only hope that sometimes, some of the things I share make you happier.


I try to forget my ideas

Keeping track of project ideas, in my experience, is usually a waste of time. I used to fear that if I didn’t capture and review my sparks of brilliance I’d forget them and an opportunity for impact would be lost.

The reality, however, is that most people (myself included) have waymore ideas for things to work on than they have time to work. Forgetting ideas is not your problem. Having too many ideas competing for your attention to execute any one well is a more pressing concern.

~ Cal Newport from,

In the beginning I didn’t try to do anything with my ideas. Even though—my mom may disagree—I had mastered bathing and dressing, I was still under the false-impression that my mind was for holding ideas. It’s not good at that. Actually it’s terrible at that.

It took me a few decades to figure out— …honestly, I never did figure it out. Rather, I started reading a bunch of stuff about how to get my arse organized, and started to write things down. College helped. 43 Folders helped, a lot. Reading Getting Things Done made the final pieces click into place.

Whereupon I entered the Second Epoch of Craig. At this time I dutifully studied, and earned my title, Wizard of Process and Organization, with a specialization in Internet Dark Arts. Do not meddle in the ways of Process and Organization Wizards; we are quick to anger and you are tasty with ketchup. As you can tell, I completely lost my marbles in the process. Near the end of this Second Epoch I reach the epitome of my list-building, (and project management setups, and universe-domination plans.) I was completely drowning in over-planned, over-committed, over-stressed, over-organization.

Cue, Thus Spoke Zarathustra, and the dawning of the Third Epoch of Craig. Wherein I straight-up deleted most of my lists of ideas and plans. The really important stuff continues to live in my level-37 wizard process-management systems. I know they’re working when I forget they’re working and yet things magically appear when I need them to.

Ideas are worthless. It’s execution, (plus luck, and timing,) that makes them valuable. I’ve a few ideas that I cannot get out of my head. Those are the ones I’m working on in an attempt to make them go away. But it’s a good day any time I can manage to just forget about some idea having blissfully done nothing with it.


And then it gets harder

I don’t think we emphasize enough the importance of evidenced-based metrics. Deep work is important. Making lots of bets is important. But if these efforts are not grounded in the reality of your field — including the hard truths about what you really do need to potentially succeed, not just what you know how to do — they are wasted.

Cal Newport from,

Deep work; yes. Making lots of bets (or, fail faster, pick yourself, iterate quickly, etc.); yes. Grounded in reality; yes. Are those all necessary? yes—actually, hell yes, amen and once more, louder, for those in the back!

But are they sufficient? If you have those three, will you be successful? Setting aside the timing and random luck parts of success, nope I think you also need tenacity.

I’m not sure if it’s learned, innate or both of those. But there’s a necessary tenacity. Ever play tug-o-war with a dog and a rope-toy? That dog has the tenacity, in Spades. (Without Googleing, can you tell me where the phrase, “in Spades” comes from?) holy shit no you dont thats my rope toy i am never gonna let go as long as you want to play this is my favorite game oh my gawd best day ever!!

But, a good dog also knows it’s a game. Tenacious? Absolutely. Drop that toy like a hot potato when something better comes up? What rope toy?


Try erasing the whiteboard

You know what the best thing about being an entrepreneur is? That you never have to experience self-doubt, the way people with normal day jobs do.

Ha. I was just kidding. Actually, as an entrepreneur, you have self-doubt coming out of your pores like cold sweat. And that’s on a good day.

~ Hugh MacLeod


A “local maximum” is a nearby, tall hill. If you find you’re standing in a puddle and the water is rising, walking uphill is a great idea. This will lead you to a local maximum. “Local” means a maximum which you can find by simply heading ”up” from where you are.

Imagine you have a project under discussion. You and your team are thinking, talking and writing [and editing and erasing bits here and there] on the whiteboard as you capture the project you are imagining. Because you have some perspective— because you can see the entire idea as it’s laid out on the board, you can probably find a maximum better than just a “local” one. You can notice broad connections, and realize that (for example) if you do some extra bit of that’s-not-obvious work, then these two far-apart pieces will give us this new feature. Hey! …that’s better, and it’s not a simple improvement—that is, it’s not simply directly up out of this rising puddle of water.

But it’s still a local maximum. Sure, it’s not the one immediately adjacent to the puddle. But it’s still a maximum in the context of what’s on the board.

What happens if, after you are done— after you’ve got the best solution you can image— What happens if you note the key features that are the “must haves”, and then you entirely erase the board. (This is a metaphor. If you do this for real, definitely take a photo before erasing!)

Now take your blank board and write in the things you identified as the key parts before you erased. Now build the thing again.

Did you get the exact same thing you had before? If not, what exactly is missing, or added, in the new version? Is this version better, or worse? What if you’re whiteboarding about something that you cannot reset and start over— You can easily erase the whiteboard, but not the actual thing. Can you learn something from doing the “erase the whiteboard” exercise that would enable you do something not normally obvious…

…to head down the hill, off your current local maximum, to a hill you can’t see from where you currently are. What if that other hill had all the current great stuff—not everything, but the great parts—and it had something else?


How do you create culture?

I’ve become increasingly interested in how culture is created within teams. One part is clearly modeling the behavior one wants to see. But I’ve been spending time thinking about how I talk to others about goals, challenges and setbacks. The more I look, the more I see I’m faced with so many interwoven elements: Communication—synchronous, asynchronous, mixed?; Feedback—positive, negative, immediate, delayed, public, private; Goal setting—team, individual, conservative, challenging, insane; Growth; Trust; Shared vision; Shared mission; Morals …

I find myself focusing almost entirely on communication. I try to spend as much time as possible explaining what I’m thinking and what my goals and visions are. At the sametime, the better I get at asking questions, the better I get at understanding what’s going on. There’s a balance. Too little conveying of direct instruction and concrete goals leaves some people struggling to grow. The opposite is also true; Too much and some people are stiffled.

“Curiouser and curiouser,” said Alice.

So what’s a question you ask your teammates that has led to surprising insights?