Command + Shift + 4 —> Highlight section —> Finder –> Screenshots –> Upload to Screely.


I’ve already taken 6 screenshots today, my guess is an average of 14 a day. If I want to capture it in a way that’s more than just a scrap of an idea, or present something more formally Screely has been a perfect tool for quickly doing that.It lays out your screenshot with a background, shadow and in a browser.

Share your screenshots just a *bit* better to make them a formal idea instead of a web scrap.

Thoughts on building a professional network

I work from home. I don’t see people that often. So for me, I’ve been able to really lean on a supergroup of online friends, collaborators, and instigators to help me get out of a rut of feeling too down about not having people I can talk to…

It’s definitely not perfect, and if I’m being honest, I wish I had more friends in L.A.

In fact, I wish I had more regular touch with a professional network in general.

The tough thing is time and energy.

I’m so focused on my work, that most weekends I’m heads down on my laptop, or I’m out of the city.

Of course, I could go to more meetups, but it’s a mixed bag in terms of whether or not it’s worth it.

And, in LA that means driving an hour and a half across town.

In the real world, we bond with people over discussions about our interests, our values, and ultimately that moment of serendipity finding someone who’s weird just like you.

The more I’ve been talking with other members from this community, the more I’m hearing some of the same sentiment as it relates to building and maintaining a vibrant professional network.

It’s just not that easy. And seems to be less so as we get older.

A place for people like us, where we can be ourselves (no pressure, no pitching).

Something regular.

I want to be in touch with others. And, I want a group that raises the bar.

To me, Creative Caffeine is a place for people like us.

A group of artists, introverts, thinkers and everyone in between who enjoys having a space to pull our head out of day to day work to discuss bigger topics.

We stay in touch via email, and the topics that surface simply set the table for us to bring our ideas and thoughts.

I think this problem of creative isolation is actually pretty serious.

It’s something I’ve hoped lessen with the weekly live streams. (Have you been to hang out?)

But I can’t help but believe that there’s something more that can be done here.

Would you mind sharing something with me?

A: What are your top 3 problems related to Networking?


B: What else comes to mind, as you think about your network?

Answer A or B or none.

I’m going to keep thinking on it.


David Sherry

Reinvention, and Going Through a Transition

The cycles of transition and reinvention are speeding up.

We used to stay in one job, one town, for 40 years. Today, we may switch jobs every 2 years, locations every four, and industries every six.

I’m going to explain what it looks like to go through a transition or reinvention.

This isn’t to give you the answer for “how to reinvent yourself”– but rather by explaining this process, I hope to give you permission to go through the stages of a transition or reinvention, and come out the other side in a better place.

So maybe you’re in a transition, a reinvention, a career change, a relationship change…

Maybe it was of your choosing, or not.


You’ve been given a gift.

You’ve been given a pair of glasses that now let you see through fog to how things really are, exactly as they are.

It’s July 2018, this is where I am, this is what is happening, this is what the landscape truly looks like, today.

See, when we’re heads down, we narrow our focus.

We’re focused so narrowly that there is a bokeh effect to the details of the other parts of life (and the world). These details have largely been ignored, or de-prioritized.

So in an open space, a pattern break, a time of reflection or rest…

We suddenly return to seeing the bigger picture of our lives.

We begin to see the full complexity of the world.

We begin to see new options available to us that were not within our realm of possibility.

The “lens” we look through widens.

If you’re fired from your job, your options for the location in which you live go from “the city you live in now” to “any city in the world.”

If you’ve been through a heartbreak, your options of who to be with go from “this one individual” to anyone in the world.

Having choices again is freeing. Seeing the world without the fog of focus is energizing.

But, after this moment, after you begin to see the larger picture at hand, areas you’ve neglected, opportunities on the horizon…

At some point, suddenly life comes rushing at you.

You’re overwhelmed by the pure amount of new data.

There are too many options. There are too many areas to explore. There are too many details to sift through.

And so you’re overwhelmed, stuck in the face of opportunity.

And then you realize that this is why we seek engagement.
Or, as I mentioned last week, this is why we seek purpose.

Without having a direction, these new options are pointless.

We see that action is what allows us to engage with the world. And that opportunities without action are the same as non-opportunities.

If you’re lost in the woods, you pick a direction to head in and stick to it. And because you’ve decided to stick to it, being lost suddenly is a mission or a path you’re on.

If you’re lost in the woods and you don’t make a decision about which way to head… You become frightened and overwhelmed.

And this is the toughest point of the transition or reinvention process.

Some may too quickly make a decision on their path.
Others will allow too much time to pass without any movement.

But at this crux, in this point of pure self-leadership, is the fuel that can propel you.

This is Steve Jobs being fired from, and returning to Apple.

There is some type of energy behind a renewed focus, a desire re-chosen, a new path confirmed.

That when a commitment is made, the path illuminates.

This part is less logical, it’s more of a feeling. Allowing a softer whisper in you to be heard, and a relinquishing to the whisper which wakes up a newfound purpose within you.

You make a choice. Not because it’s not without trade-offs (it is), not because it’s perfect (it won’t be), but because you have the ability to make this choice.

This is the self-leadership is necessary today.

And the process that takes us to the next stage in our journey.

The Reason Ideas Spread (To Early Adopters)

THE great indicator of growth is that which cannot be tracked: Word of mouth, person to person.

When an idea flows through the culture…

When it spreads on its own…

How can you create something that does this?

I’ll lay out the simple, difficult kernel of how this works.

It’s the key to understanding early adopters.

And like any kernel, it’s deeply filled with DNA and layers of complexity, even if it’s wrapped in a simple to grasp statement.

(As a side note, the nuance between understanding what makes up a kernel, and those who just see it’s exterior, is the same difference between understanding what spreads and what doesn’t).

To spread an idea in a noisy world…

There must be a surprise. 

And in that moment surprise, we learn something new. Right then and there, we change our worldview, we confirm our suspicions, we open a new door of possibility. We become aware of something that we didn’t previously know.

Without the surprise, there is no education.

We know that education is important for “user onboarding” – but most onboarding misses the point. People see only the functional, sterile facets of education, and miss the deep ones.

Most onboarding teaches you how to use your application, how to drag and drop an image or find your settings.

Great onboarding transforms the way you view the world; through the education and story of something you were unaware of.

I don’t know anything about Golf.

I’ve only played a few times in my life, and I’m pretty much terrible. If I were to attend a tournament, I’d be entirely clueless and bored the whole day, probably thinking about how I was getting sunburned and wondering where the food carts were at.

But If I were to attend that tournament with an expert, someone who’s a lifelong fan who explained all of the subtleties to me, all of the hidden strategies of the game, the history, the rules, the controversy between players…

I may suddenly find myself fascinated.

And, later, (maybe) find myself wanting to take up golf, and engross myself in the sport.

Or maybe in the future, I would describe to others what is so interesting about the game.

So, one teacher might show me how to swing a club.

Another teacher might show me the beauty of the sport.

This goes for anything else, from Origami, to hotpot cooking to Military history.

I feel this way about bitcoin.

Even if I never bought a bitcoin it would have still been one of the best products I’ve experienced in the last few years.

It’s completely changed my worldview within 5 minutes of understanding it.

It was a surprise.

It showed me the door to economic theory, finance, governance, sovereignty and more.

It made me ask new questions.

The more we begin to understand what makes up these products, stories, industries, where the magic lies within them, the more we appreciate them.

To love is to appreciate subtleties, to find shiny, that which most miss.

Your product won’t be for everyone.

But for a few, they will find it shiny, and they will pay with their attention.

These are the people who become great customers.

Not because you gave them a tool and showed them how to use it.

But because you showed them something they’d missed, something beyond the utility.

Something they were surprised to learn.

And if you go about moving people this way,

Your ideas will spread for you.

Because what you showed them, they will share with others.

And the most important aspect of the idea, spreads…

I won’t give you advice

I took a survey and received 400+ responses from readers.

I nearly cried reading them.

The question I asked was this:  What is the single biggest challenge you have as a creative today?

(Just a few of the responses below)


“I’ve been having a rather tough time following my thoughts and turning them into something concrete for the past few months. It feels like I’m hiding from myself and holding myself back…”

“It’s hard to keep believing in the things I’ve started, and it’s hard to keep going after a solid few months. I get tired and second guess everything and overwhelmed and frustrated. And then I isolate from it all.”

“I am 80% done with a book but lack the motivation to finish.”

“trying to move past whatever blocks I’ve seemed to place on myself”

“I have visions so much bigger but can’t justify the time by knowing how much it could bring in or, worse, knowing it will be meaningless financially but fulfilling creatively. That stuff–which I love–loses almost every time.”

“I’m trying to motivate myself to think that my creativity is worth it.”

“I’m finding a lot of resistance in starting my YouTube channel because I’m scared that no one will watch it and the effort will be in vain.

“I love dreaming up new ideas and figuring out how to make things better, but have a hard time actually implementing my ideas and following through.”

“The rewards I receive from my work have all but disappeared, and I’m not hard to stay motivated. I’ve been procrastinating and avoiding things I don’t want to do because of it.”

And many more like that…

To sum up what I heard in many responses:

“I’m stuck”
“I can’t get motivated to start/finish my project.”
“I’m feeling professionally empty.”

What struck me is just how common this is. And by the same point, how much potential there is.

I won’t give you advice.

I don’t know anything about your life, or the complexities of you’re problems (at least not yet).

I’m also not going to take an image of what my path looks like, and try and place it over top of yours.

We all have different skills and interests and passions.  We all have a unique path to take.

The truth is, most times you know deep down who you want to be, how you’d like to move forward, what the right decisions is…

You simply have gotten stuck in a rut, and you’re unable to get yourself to see outside of the fishbowl you’re in (so to speak).

In a more positive light, you feel like:

“I still have my best work, relationships, and life in me, I just need to find a way to bring it forward.”

But the path forward is not advice or tactics or pressuring you through (forcing yourself to do something is a recipe for lost time and energy). It’s not hyping you up to feel a certain way, putting yourself in a state, that doesn’t last.

No, what I’ve learned is that what’s needed for growth is…


To learn to see in a new way.

So what I can do is turn some lights on.

Provide a different perspective.

Help you examine whatever roadblock or stuckness you’re in so that you can hear your own voice, get clear, and lead yourself through the next phase of your growth.

This is the purpose of the newsletters of Creative Caffeine.


[Something new]

I’m not sure if I’ll offer this forever, but it’s worth a try.

I have exactly four spots per week open in my calendar, each for a free half-hour phone call where you can bring your lay out your problems on the table to discuss.

Think of this like an artists support line you can call when you feel stuck.

No judgments, no pressure, no call-waiting music.

Who this is for:
CC subscribers (I prefer people who get what I’m about).
People serious about their personal growth.
People who see themselves as the main obstacle to overcome.

Who this is not for:
Pitching me business ideas, sales etc.
People looking for growth hacks, tricks and tips in marketing, sales etc.

I know this isn’t for everybody.

And it’s an experiment, so I’m not sure if people will book or if I’ll want to continue this forever.

But if you feel stuck,

A line is open.

Book here.


P.S. You know, some of the most rewarding (and profitable) investments of my life of time and money have been on learning more about myself. These discoveries have been priceless to me. In many ways, it’s the purpose of my life. Everything I do is another way to train, see things differently, to challenge myself, and ultimately learn more about who I am and how far I can go with the time that I have.

Algorithmic Email

What is it that makes social networks different than email?

Right now Gmail is a chronological feed, could it not be in the future that AI will read the mailings and place them in an order depending on urgency and other markers of importance?

It’s already beginning, with the introduction of “Promotions” and “Social” tabs to Gmail.

If we were to see the rise of algorithmic email, it would pose a new, and somewhat disconcerting question for users:

Do we own our inboxes, or does Gmail (or name your provider)?
Are our communications private, or are they at risk?

If an algorithmic feed for email does eventually happen, I suspect we’ll see some type of movement towards a decentralized inbox, with better controls for the user. I also suspect that Marketers will do everything they can to game the inbox, as we’ve seen with SEO. Gmail could quite literally shift email strategy, if it hasn’t already…

We are ok with the spam box controlling the flow, but how will we feel about this next step?

The 3 Businesses

Businesses have 3 problems.

Reduce the friction in any of these three problems, and youll find you successful spot within an organization.

From HBR (Unbundling the Corporation):

When you look beneath the surface of most companies, you find three kinds of businesses —a customer relationship business, a product innovation business, and an infrastructure business. Although organizationally intertwined, these businesses are actually very different. They each play a unique role; they each employ different types of people; and they each have different economic, competitive, and even cultural imperatives.

1. People (Internal Team/External Customers) – Attract and build a relationship with customers.
2. Technology (Product) – Come up with new technologies and products for customers.
3. Scale (Infrastructure) – Making the Logistics and Delivery of product that’s efficient.

In the great unbundling that’s happening with the Internet, we’re seeing more companies focus on dominating one of these key areas (focusing on all three tends to lead to conflicting energies).

Personally, I’m in the Customer Relationship Business.

How about you?

Community Mail: Intelligence, Business as Machine

One of my favorite questions to ask people is:

What is the difference between smart and intelligent?

In reality, there is no difference. At least not according to a dictionary or thesaurus. But what’s interesting is that due to question bias, people try really hard to find a difference because they “know” there’s a difference between smart people and intelligent people.

I’d love to ask you the same question! What are your thoughts?


Hi David,

As an educator, I beg to disagree to some extent with your premisses :

You write :
Intelligence is connecting ideas, things, people in a way that gives us a result.

Intelligence is finding elegance in a new option, seeing a new opportunity, asking a new question.

But how can you connect what you don’t know or realise that what you thought was new had actually been discovered ages ago…?

I think the very real problem you highlight, viz. so many things to read / learn, so little time & then there are computers anyway, stems from the conflation of two separate issues :

1. Our nostalgic hankering for the Renaissance Man model of culture & knowledge (and Leonardo da Vinci was exceptional even for his time anyway!). Modern science has simply put paid to that myth, but most Western education curricula are still in thrall to it.

2. Computers can do everything we can faster & better : well yes BUT what if all power resources eventually disappear? Good luck with running operating systems then… plus not everyone can understand coding & algorithms and, personally, I’m not wild about a system where ignorance will allow the few to keep distorting things for the many.

What a good education should provide you with is the ability to think on your own two feet, make informed decisions and not feel guilty about not having universal knowledge.

Keep up your creative caffeine, it makes for really enjoyable reading.


Thanks David, I really enjoyed this read. I definitely have suffered from feeling less than (even while excelling) my whole life. The challenges and triumphs that come with running a business can both relieve and exacerbate that. This is a welcome reminder to leverage the tools I have without feeling I have to compare myself to them.



Jessica S


You are speaking my language.  Actually, that of Career Vision.

For the last 3o years, we have been giving aptitude tests to help people discover their inborn talents. Aptitude testing identifies and measures where a person’s talents lie.  Those are the areas to concentrate on and develop.  Those are the areas of study that will come more easily and more quickly to you because they are part of your natural strengths ( put me in a biology class and I am your girl.  Put me in a math class and I want out). What comes naturally to one person is rejected by another because it is ‘too hard.’

I invite you to our website, and that the Ball foundation

I think you will find it interesting.

Accentuate the positive,

What about ‘business as a garden’? This fits better for me. We work in an ecosystem, interdependent on others not tinkering alone in a garage.

As Kate Raworth says in Doughnut Economics – goodbye spanner, hello secateurs:

“Say farewell to economy-as-machine and embrace economy-as-organism. Let go of the imaginary controls that promised to pull markets into equilibrium and, instead, get a feel for the pulse of the feedback loops that keep them continually evolving. It is time for the economists to make a metaphorical career change, too: discard the engineer’s hat and spanner, and pick up some gardening gloves and secateurs instead. …back in the 1970s, Friedrich Hayek himself suggested that economists should aim to be less like craftsmen sharing their handiwork and more like gardeners tending their plants.”

Yes, it foregrounds economics, but I think it applies just as well to businesses, organisations, enterprises. Imagine warm, full-of-life human beings working on a living thing that we’re part of, that we work with, that’s regenerative rather than tinkering with, working on, a cold machine, that’s (often) extractive. What do we need to do to help our garden thrive, to allow plants to flourish and produce, now and in the long term?

Thanks for writing Creative Caffeine, I always read it, and it always makes me think.

Best wishes


Hi, David

Your email is timely. I’ve always had trouble separating myself from my work whether it was when my work was school, or shoveling gravel, playing music professionally, or even now being a pastor. Some seasons I’ve been better at than others in recognizing that I am not my work.

Last week I spent significant time meditating on this old Hebrew Scripture attributed to Solomon, the wise king, on work. It highlights the difference you mentioned between the one who is able to wake up early for a fresh start and the one who is stuck in the drudgery of the daily grind:

There is nothing better for a person than that he should eat and drink and find enjoyment in his toil. This also, I saw, is from the hand of God, for apart from him who can eat or who can have enjoyment? For to the one who pleases him God has given wisdom and knowledge and joy, but to the sinner he has given the business of gathering and collecting, only to give to one who pleases God. This also is vanity and a striving after wind.
Ecclesiastes 2:24-26

Have a great week!



Art you smart enough?

Of course you are!

Now I’m not talking about astro-physics or building a Deep Mind computer.

But to run a company, to make a change in the world, to do something that makes a difference…

You’ve got what it takes.

The problem is you’ve probably questioned that your whole life.

School had grades, and you’re compared to everyone else around you and are reminded of where you stand since the first grade.

It’s a prescribed status, like the letters of your college or degree or lacks their off which supposedly act as a stamp of where you stand.

Except that it’s got no relevance to your success. These tests and systems are about a general knowledge.

But my guess is that in at leats one area of your life, you’re doing something that looks like genius to someone else.

And the funny thing about genius…

Most of them can barely tie their shoes.

Einstein can win the Nobel prize but Einstein with women….

Nicola Tesla trying to make a sales pitch, or take photos, or lead a team of 100 people…

See specific intelligence is just that, specific. They train their entire lives in one field and they are truly gifted, special and intelligent in that area, no doubt.

And I’m not saying there is a degree of difference in intelligence, general or specific.

But we’re in the computer age.

Do you want to compete on intelligence for smarts against a computer?

So, memorization is dead.

That radiologist who’s scanning simply went to school for 12 years to figure out how to do that.
But that job will soon be handed to the computer.

IBM Watson’s medical computer can stay up to date on the latest scientific research more than any doctor in the field… why? Because there’s over 100,000 new documents to be read each year to stay on top of the field.

But for a computer, that’s no problem.

So now what? What do we do?

You’ve got to look for the areas in your life that come naturally to you and difficult for others.

Are you smart enough?

Of course you are!

We’re not born doctors, or firefighters or authors or stylists…

We learn it somewhere along the way. Maybe we learned it in only just the past few years.

And what is intelligence, really?

See, it changes. If you no longer have to memorize or hold vast knowledge in your own head…

Intelligence is being able to figure it out, whatever situation comes up.

Intelligence is being able to lead others.

Intelligence is connecting ideas, things, people in a way that gives us a result.

Intelligence is finding elegance in a new option, seeing a new opportunity, asking a new question.

In this day in age, it’s how we connect ideas and apply ourselves.

And soon enough we’ll leverage the IQ of a computer, with the creative impetus of a Human!!

P.S. You don’t need inputs reinforcing the idea of what your IQ is. It’s like a placebo-label. Don’t let it stick!

P.P.S. What I mean is that sometimes we read articles about the successful that subtly convey we don’t have what it takes and that they’re superhuman.

The Naval Tweetstorm

Twitter is where culture meets conversation.

Instagram is too image based, and there are no discussions. I mean, I’m not going there to learn. It’s for shopping, flaunting, and sharing travel.

Facebook is the town square: where you bump into old friends and stay up to date.

But on Twitter…

Networks are being constructed, topics are being discussed and people are genuinely meeting each other and exchanging ideas.

Circles of people with influence are emerging, mostly in Tech but also in law, sports, investing, self-improvement, health:  All are sharing their insights publicly and regularly.

And the best rises quickly through these spheres thanks to the ease of sharing with the retweet, something Instagram and Facebook have somehow avoided, so things spread quickly…

Like this series of Tweets from @naval about “Wealth”.

Not only has Twitter stepped in to translate this into multiple languages, people are analyzing it, discussing it, drawing up illustrated versions of it.

I haven’t seen a social network move this quickly on something outside of Reddit.

So somehow Twitter is social media that makes me more intelligent. It’s shown me many books, sites, people that I wouldn’t have found otherwise.

In fact, I can’t keep up with my feed.

Sure, bots are rampant, and political Twitter is to be avoided… but…

There’s a quality conversation happening there!