Reess Kennedy

Ideas, sharings, projections

Being the “Picture Painter-in-Chief”

Picture Painter-in-Chief is basically Elon Musk’s job title.

Yes, technically I am sure he is brilliant and just as capable as the senior engineers he employes. But the guy is doing so much, he can’t be in the weeds doing the research and math and all the nitty-gritty.

He’s really more like the storyteller or picture painter. This is his main role. The latest video for his latest endeavor, The Boring Company, is the best example of this. (Embedded at the end of this post.)

Normally, you’d watch something like this and think, “This is science fiction, never going to happen.” But Elon has the defied the odds so much and in is such an influential place of power and has gained so much good will he has absolutely reignited the 60s era space race imagination of the country.

Because of this, he now releases a video like this and instead of being dismissive about it we think, “Yeah, I can see that. Why not? He could probably do it.”

And maybe even more importantly we think: “If he can do it, what else can I do?”

It’s an awesome world to live in when we have these storytellers able to dream a dream and have enough of a track record of success and goodwill behind them that the world believes that dream!

And it’s awesome to live in a world where we have brave men doing hard things and inspiring everyone else to imagine and paint beautiful pictures of an improved tomorrow.

The freedom of constraints

It’s a paradox but it’s true. Constraints help boost productivity.

Setting time constraints is clearly a way to focus the mind. I wrote a quick post on this. There are, however, also constraints on the form of your creative product that can help as well.

Somewhat related is the common quote that “discipline will set your free.”

The older I get and the more experience I have the more I realize it.


  • Twitter: Having only 140 characters eliminates creative hesitation. People who might never create a blog post are prolific tweeters. And there’s real value, in the aggregate, of the creative output this 140 character limitation has caused.
  • Haiku: These are poems with a small constraint just like on twitter. It’s really fun to debate and wrestle with only 17 syllables. If you’re trying to write a book and you want to make sure every word is perfect, you’ll be working on it for eternity and still not finish. With 17 syllables you feel like with a little bit of thought you can get close to the perfect words to say something in a short time.
  • Bootstrap or any frontend, grid-based design framework: You can still basically do anything within a design grid but having a grid system to design within boosts confidence in the reliability of the final product and that makes creating more fun.

The hardest thing I do might be to write a post on this blog because there is no set format.

I like M.G. Seigler’s idea of trying to restrict his blog posts to 500 words with his blog I should have thought of that.

Numbers to remember each day

  • 14 billion
  • 4 billion
  • 70,000
  • 17,000
  • 2,000
  • 1492
  • 1776
  • 7.5 billion

These are numbers that rattle around in my head.

I think about some daily.

Meditating on these numbers helps me keep things in perspective and motivate me to be more bold.

In order, the numbers above represent the following:

  • Age of the universe
  • Age of earth
  • # of years ago all Homo Sapiens were known to live as smallish tribe in East Africa before spreading and taking over the planet
  • Earliest signs of art created by Homo Sapiens in France at Lascaux
  • Approx distance from death of Christ
  • Columbus new land voyage and America
  • America freed; rethinks what a country should be from scratch given lessons from history
  • Approximate number of humans alive today

2009 was, apparently, the year I invented Uber and Pinterest

2009 was, apparently, the year I invented Uber and Uber Pool and Pinterest.

Except, I didn’t.

Cleaning my GDrive today & find this stray note in doc called “2009 – Notes.”

Screen Shot 2017-03-12 at 1.56.14 PM

Then I find this:


This was many something like what Pinterest now is.

Common, oft-repeated takeaway is: Ideas are freeeeee, free, free and abundant and thousands of people have the same or similar idea at the same time. There were dozens of people working on the invention of flight around the same time but only the Wright Bros get credit. Same thing with the telephone. Similar thing with this Facebook thing I use right now to distribute this message.

The great book The Master Switch talks about this a bit too.

Eternal execution for the creative mind

If you’re creative, you have a billion ideas. You have ideas that sprout from ideas. It can become this wild tree of ideas that becomes so heavy it starts to jeopardize the strength of the root structure!

You’ll begin executing on a task and find a new idea emerges about how to create some new system or product or spreadsheet or article idea that will help with X.

Not allowing new idea branches to distract you from your primary, current objectives requires focus.

For me, I have to constantly ask myself, “What are the three things I can do today, right now, to move me closer towards my specific daily and weekly goals?”

And then to avoid my creative mind from distracting me from the execution of these tasks I have to set specific time goals to complete them.

That’s it.

Execution for creative people is all about asking the following two questions constantly:

1. What are the are the three things I can do today that will help strengthen the existence of my idea in the world?

2. What is my specific time goal for how long getting this task done will take?

I literally “gameify” all tasks this way. I set a timer on my computer write the task out on my to do like like, “Get the email introduction to John written by 1p.”

And then I race to hit that.

It’s tiring but effective. And can be fun too. Because getting way more done is fun.

Goalie training: Blocking bad inputs

When you get older you realize how important it is to be careful about all your inputs.

If you care about maximizing your output, you need the best input of food and information and people.

“Garbage in, garbage out” is a familiar refrain from Computer Science and database management.

It’s true.

Inputs need to be thought of as everything:

People and the relationships in our lives we let in.

Media and the books and music and film and advertising we choose to let in.

Chemicals or the food we let in.

The more I think of my body as a machine the more I am able to program it to get more of what I want out of it.

But this starts with understanding crumby inputs and blocking them know they will just bring you down and stop you from seeing the good stuff coming.

Blocking requires persistent discipline. It’s like being a soccer goalie and a lot people are punting these rockets at you and you have to protect the goal. At first, you fail and let some in the net. Over time, making amazing saves becomes easier for you and requires less effort.

Your motivation to keep blocking increases as you see the reward that comes from the increase you feel from only allowing the best things in.

Relaxation at tension

Forcing the body to relax under pressure is really powerful. But it takes practice. And focus.

The five mile road race I ran this morning had me thinking about this. At mile three my muscles start to tighten and I began, as people often say, “grinding.” But today I focused on using my mind to fight against this muscular tension as I carried my pace over the final miles.

it seems like impulse pushes us to meet pressure with pressure but experience tells me to, at times, resist this.

In today’s race I maintained and accelerated my pace over the last few miles while working hard to override this impulse to tighten– and to relax my muscles instead. It was a transfer of pressure from my muscles to my mind. My mind now had to work harder to improve the performance of my body by calming it down.

In this way, tense running becomes mindless, lazy running. Coaches tell you not to “fall asleep” during a race and this essentially means turning off your mind’s power as force to keep your body relaxed as you push forward towards the finish.

Martial arts disciplines try to teach these principles of relaxation under pressure as well and Yogis likely become accustomed to forcing relaxation under the tension of a stretch.

But I also think this relaxation under pressure can be generalized to produce benefit outside of running and athletics–and that’s the purpose of this post.

Business dealings and relationships can benefit as well. I remember listening to a tense Senate inquiry of Apple CEO Tim Cook a few years ago that highlights this. The senators were, at the beginning, grilling Cook and, amazingly,  it seemed that the more pressure they put on him the softer and more calmly he spoke. It was masterful. After a few minutes his relaxed but professional demeanor diffused their tension completely. He knew he could not meet fire with fire. He had to meet all levels of increased pressure with increased focus on relaxation.

I’m sure it was hard for Cook to do this. Just like my legs started to tighten today at mile three, I’m sure Cook’s temper started boil a bit when Senator’s really started to dig into him. He figured out a way to override his default and created a better personal outcome as a result.

Cook was such a master of this it seemed he’d had a lot of practice with being “calm in the storm.” This ends up being the mark of a great leader and it’s something you can learn with practice and study. Engagement in challenging physical activities can be instructive and merely the general awareness and acceptance that relaxation under pressure can help one achieve better performance goes a long way towards moving one closer to a Tim Cook-like mastery of this art.








Trump: Magician for the unwitting

Magic only fools you when you don’t know how it’s done–the technical aspects of the trick.

A magician watches another magician and he might be impressed by the delivery but he’s not fooled by the method. He knows how it’s done.

Trump is a magician, like David Blaine. Instead of using sleight of hand to con his observers, Trump uses “sleight of words.”

People fall for it because they haven’t studied his method–the technical aspects of his use of language.

The good news: We can learn all the “magic tricks” Trump uses to fool people by studying the attached cheat sheet which defines all of the logical fallacies.

These logical fallacies aren’t new, they’ve been around since the beginning of time. They’re just hard to memorize so very few of us do.

Without a solid understanding of these, however, we might be prone to grant credence to dubious and false statements.

But with an understanding of these tricks we see the method.

So use the download below to arm yourself against trickery.

(Or trick others who haven’t studied it just like Trump. Your choice. Free country. Love to all.)


These were modified and simplified for this post from

7 Trader Joes-inspired business success strategies I use

People in NYC love Trader Joes.

I’ve found that TJs operates by some simple principles that can be applied to any business which I outline below.

1. Don’t try to do everything for everyone
Trader Joes stays nimble by only offering a few items but making sure people really like those items. They’re okay knowing that you’ll have to go elsewhere for some things because they know you’ll still buy from them the things they do better than others. Trying to create a store that would be a “one stop shop” would hurt their ability to do all the other things they do well. “Put more force behind one arrow” is a powerful mantra for any business and the way a David can take down a “Goliath” — the focused slingshot rock right at the blind spot inevitably created by the Goliath’s size.

2. Set reasonable prices, make money on volume
TJs keeps things simple and wants to offer value. People recognize this and customer loyalty is created. People also recognize that the lack of frills is a part TJ’s charm and what allows them to offer affordable quality.

3. Experiment and discard what doesn’t sell
TJs is constantly introducing new stuff and removing old stuff that isn’t selling. Inventory or product or feature pruning and focus is important with any business.

4. Invest your profits into your staff
Staff members at TJs are generally happy and friendly. Maybe this is because they make more money and are given better benefits than those working elsewhere. The customer experience is far more enjoyable as a result. It sounds corny but it does seem like somewhat of a family when you shop there. Consider how much more confident you’d be in retaining customers at your own business if they also felt like they were a part of a family as a customer of your business.

5. Give free samples
Free samples just make people happy and show you’re confident with your products. At TJs this means literally giving out food samples but in other service of product businesses it may sometimes mean providing your services or products at a discounted, below market price at the beginning to make it easy for new customers to see how good you are and win trust.

6. Offer sustainability
Having an advertised mission beyond profit shows customers you have a higher purpose and are working to also make a larger difference.

7. Keep location overhead low
People care about the value of the products and not the office space. Good employees will care more about whether they are making a good living working on something they care about than the grandeur of their office.



Newspaper front pages

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