In Real Life’s Mess I wrote about how organizing a lunch turned into a chaotic reminder of how unpredictable and complicated real-world interactions can be. Organizing that lunch began simply — pick a time and place, send a few emails, provide a clear way to engage, and manage RSVPs.

What I didn't, and couldn't, predict? All the big and little ways people would surprise me. I went in with an Apollonian game plan — neat, linear, direct. But life reacted with Dionysian chaos, throwing surprise after surprise from email miscommunications to extra attendees.

I want certainty, to set the rules and exploit them, but the real world is an exploration in chaos. I can see this as an insurmountable obstacle, and I can stop, give up, and maybe never try again. Or I can see the pushback. I can find harmony in the tension of opposites. If I accept both the plan and the pandemonium, I can do things and come out stronger, ready to tackle the next wall with a grin.

This is all so easy, so obvious when laid out. Except knowing how this dance works is akin to what Mike Tyson famously said, "Everyone has a plan until they get punched in the face."

Yes, you can just do things. That's step 1. But what about steps 2, 3, 4, and 5?

Keep pushing until you break through

When you begin to just do things, life pushes back. People get in the way (they're trying to just do things too). You face steps you didn't expect, work you don't know how to do. There's negotiation and compromise.

Doing things means slogging through the inertia of the way things are. Like trudging through two-foot deep mud, the mud sticks to you, holds your legs, weighs you down.

You have to keep pushing. That lunch was a mess of ignored or misread emails, late arrivals, and even waitstaff drama, yet it happened all the same. Everyone showed. The experience was a success. We'll do it again.

The lesson? Yes, you can just do things, but expect to hit walls. You must go full Kool-Aid Man, and smash through the brick with a grin and a shout: "Oh yeah!"

When it's tough, that's a sign that something big is happening. If you push with audacity, you will break through, going from "Can do" to "Can? Did."

The "You Can Just Do Things" process

This "You Can Just Do Things" steps are easy to lay out:

1. You can just do things.
2. You start doing.
3. The world reacts.
4. You keep pushing.
5. You get things done.

Easy to say, hard to do. Beyond routine tasks, "zero to one," creative work looks more like a sigmoid curve. So much effort with little to nothing to show for it. A Sisyphean struggle, this beginning point is where we most often quit. But if you keep going, things start working, and eventually, they accelerate.

Everything changes.

→ The creative act looks like nothing's happening ... at first

You begin. You push and push and push. Nothing seems to work until, like a sigmoid curve, a phase shift takes place. You go from zero to one, and everything changes.

Why doing things in the real world feels so hard

The creative act has always been this way: Hard. Today it feels harder still. Except the nature of people hasn't changed, so what has?

I think the difference is the pervasiveness of technology. Technology is a lever that makes it possible to turn less labor into more output. Mankind's knack for using technology to solve problems may very well be the real defining characteristic of the species.

Today, technology has encroached into nearly every facet of our lives. With global average screen time per day at nearly seven hours — close to half our waking hours — our default setting is, "There's an app for that." And there usually is. Tech has intermediated everything, from the default way we order goods and services to underpinning our food production and supply to making media creation easier than ever, too, ensuring we are never far from distraction. Consequence? We use more technology — algorithms — to determine what's attention-worthy. And at last we have artificial intelligence, which may upend everything.

Just over the last several weeks, I have had countless back-and-forth conversations across three, sometimes four, AI systems. These interactions are incredible for their depth. I use AI as a thought partner, marveling at how deeply it listens and how thoughtfully it recalls what I’ve said. I use AI as a coach, too, and like a coach it calls me out. I use AI as my personal, genius intern, helping me do more than I ever could have done alone, like generating bespoke illustrations (as for this post) or coding like in the HTML (above) or an annual step calculator I published for BirthdayShoes. It's hard not to love this amazing technology. I also worry about it trains me to believe shortcuts exist for everything, that I don't need anyone, not really.

Whether basic technology like a chat app or Amazon, or advanced technology like AI, what does the adoption of this technology displace? And how has it shifted my beliefs about what's possible? On the one hand, technology has made me more confident than ever about Step 1 — that "I can just do things." However, once I start doing (Step 2) and the real world pushes back (Step 3), it feels harder than ever. Technology has lulled me into believing doing should feel effortless, a series of keystrokes, taps, and step-by-step instructions. My digital reality hides all the hard work under layers of abstractions. The more I use innovative technology to do, the more I believe that this is what progress looks like — problems neatly solved by technology. Somewhere someone is doing things, and we all benefit, standing on the shoulders of their achievement.

Is this progress good?

We deem all of this technology "good," even as we become more and more dependent at every turn. In practice, we are like the kid who's learned to do math but can (finally!) use his calculator. We feel powerful. We are powerful so long as we stay within the confines of what our technology allows.

Soon we forget what it's like to live without our precious levers. The problems that aren't solved easily become problems we can't tackle. We look in earnest for new technological silver bullets and quick-fixes. We distract ourselves silly, resigned to live within the confines of a video-game life, a life that can become plastic, even brittle. We stop imagining life could be any different.

Deep down I worry how this could end. Should the time come when we can't use our technology, we'll be thrown into a chaos we don't understand and without the tools we need to survive. The real world will look disordered, uncertain and therefore unpredictable — incomprehensible. Our technological power taken from us, many would rage, cursing the sky like a child — or adult — whose WiFi has gone down permanently. Many will retreat completely, unwilling to let go of the past and unable to imagine a future without. Will we know what to do?

My prediction may seem dire. I'd agree except we already see evidence it's true. Take, for example, the hikikomori in Japan. These are people who have withdrawn from society entirely, overwhelmed by a real world they’re no longer equipped to face. Life as a hikikomori is possible because of technology — they can bring a digital facsimile of the world to their rooms, supported by a technologically advanced society. Technology makes this possible. But does it make this kind of life inevitable too?

If you squint your eyes you can see how mankind's knack for technology can become pathological. The trend is troubling, but the future is not yet written. All is not lost, not if we recognize the dependencies of technology, remembering there's more to the story in the real world. Not if we have courage enough to return to the Dionysian mess of the real world to "do things." Not if we keep pushing — Step 4! — through the chaos.

There is a balance to strike between resigning ourselves to a comfortable life of certainty and a dangerous life of possibility. My hope is to find that harmony, that beautiful tension of opposites that marries the power of technology with the power of my own agency. My aim is to jump into the fray of reality, engaging in the messiness of life. My prayer is to use technology more than it uses me because my agency is a gift, and I must use it wisely.

For believe me! — the secret for harvesting from existence the greatest fruitfulness and the greatest enjoyment is: to live dangerously!
—Friedrich Nietzsche, The Gay Science

The dangerous practice of life in real world

Hopes and prayers are not enough. I must practice engaging in the real world, facing down the unexpected and unpredictable. I must practice resilience and persistence to be strong. I must live dangerously.

So what am I doing? I start with awareness — that's the thrust of "You can just do things." Though I hear the deadly siren song of technology, I know that I can no more reject technology than reject my humanity. I will use technology to throw myself further, aiming to lever it to the hilt when I can but discard it when it dulls the danger of life. I won't blindly adopt technology without — at least and at first — guessing its costs. And for the technology I adopt, I won't blind myself from knowing what I can about its costs at last.

I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived. I did not wish to live what was not life, living is so dear; nor did I wish to practice resignation, unless it was quite necessary. I wanted to live deep and suck out all the marrow of life, to live so sturdily and Spartan-like as to put to rout all that was not life, to cut a broad swath and shave close, to drive life into a corner, and reduce it to its lowest terms, and, if it proved to be mean, why then to get the whole and genuine meanness of it, and publish its meanness to the world; or if it were sublime, to know it by experience, and be able to give a true account of it in my next excursion. 

— Henry David Thoreau, Walden

Most importantly, I will make a practice of returning to Thoreau's woods — the real world — to create, to be uncomfortable, to experience the mess of real life.

Practice can look like choosing to do all sorts of things "the hard way." I don't need to reinvent the wheel. Practice can mean organizing gatherings of men in the real world — I know how hard that can be! Or it can be as simple as picking up the phone to call a friend rather than firing off a text. It can involve getting lost instead of using turn-by-turn directions. It must mean exercising my body. Practice must mean challenging my mind — i.e., through focused attention and learning new things. Practice is surely even opting for food that hasn't been deconstructed and reassembled in a factory. Practice is doing things with the living, whether individuals, groups, businesses and organizations, or family.

Practice must unavoidably and always require asserting myself on the real world. If whatever I aim to do scares me, I'm doing something right.

What other ways exist to assert myself on the world without using technology? Also, what ways are there to use the power of technology to attempt things that have never been done before? Artificial Intelligence offers a power unlike any we've seen before. We live in exciting — and frightening — times. And if we are willing to do things, to keep pushing, to overcome the inertia and walls in our way, not only might we do more than we ever dreamed possible, but we may build a momentum that makes us unstoppable.

"Opportunities multiply as you seize them."
— Sun Tzu, The Art of War

I can just do things — so I will! And by doing things, I might find the harmony in the tension of opposites.

Thanks to my friend Isaiah Baker for editorial, from noticing and bringing my attention to the Apollonian/Dionysian to pushing me to make this more personal, to many other things. Finally, Zay has exemplified choosing to live dangerously — he left a high-paying, safe job at one of the most prestigious organizations in the world, Goldman Sachs, to go build a business in south Florida. You must read his story if you haven't. His example teaches me daily that if you want to fully immerse yourself into the Dionysian messiness of the real world, start a business.

Two days ago, I began organizing a discussion group lunch. This would be the group's second gathering, my first time organizing. Though fifteen people were invited, the round table at our chosen restaurant only comfortably fits nine.

(A discussion lunch can only be so big, anyway.)

The invite went out, and within hours, all seats were claimed. Everything was going smoothly ... until a new guest, a promising new addition since the first lunch, reached out. This individual had missed the cutoff but emailed me directly, asking to join. I responded right away, explaining we were maxed out for this lunch — but he’d be first in line if someone canceled. I also left open the possibility of squeezing in a tenth seat.

Unbeknownst to me, he’d also emailed another attendee and the organizer of the prior lunch. Unaware I’d already responded, both replied and pointed him back to me — unintentionally giving the impression there was still room at the table.

Ugh.

This guest was just acting in good faith, trying to get a seat. Meanwhile, though my original response made sense at the time, now it felt like a gaffe. Would I come off as rude to this man I'd never met? I probably appeared disorganized to him. Meanwhile, granting his request could make me look inconsistent with the broader group.

As these thoughts raced through my head, I took a breath. Everything is fine. This will work out. We'll let him join We’ll make it work. Nothing’s perfect. This is life.

This hiccup revealed something vital: Doing things in real life is messy.

Organizing anything involving people, decisions, and constraints — some unavoidable, some unforeseen — is fluid. You have to adapt. Life isn't a transaction but a negotiation.

This lunch was an example of how real life is full of challenges that don’t follow neat rules.

By comparison, digital life lets us dodge this mess. Digital has guardrails — enforced as defaults through software and the conventions of modern media. Online, we control the terms. Texts and emails are consumed on our schedule, shielding us from the real world’s chaos. Online, I can order goods, services, food, and never deal with anyone. Something profound is lost in this process.

That's not all.

Online is fake. Everything is curated. The news, communications, content — all are now products that have been crafted and readied for mass production and consumption by anyone ... or no one.

Online is safe. I know, people can be mean online, but the downside is almost always clipped. You can always block. Ignore. Leave unread. Close the tab.

Online is a game to be played. You get infinite lives, which makes you care less about the one life that matters.

No surprise, the more online I am, the less equipped I feel to handle real life. Digital makes me brittle. Navigating real-life messiness teaches me to surf uncertainty.

Things can go wrong and still turn out right. Take the entrepreneurial mindset that "you can just do things." This mindset demands assertion. You have to say yes even when you don't know exactly how the work will be done. You have to say no and push back even if it risks judgment. Doing things in the real world is a skill sharpened by practice. A digital existence, with its rigid, predictable structures, lets that agency atrophy.

(Schooling, with its rule-bound systems, does the same. But that’s another story.)

Our tech-driven world, obsessed with ease, helps us avoid friction. In the short term, we get the quick win, the instant gratification. In the long term, we lose more than we realize. Do you want to experience life passively? Or do you want to push through the chaos and change the world?

You can avoid dealing with the mess of real life — but you shouldn’t. Embrace the mess — that’s where life happens, where what you do is real.

Fourteen months ago I left Mural, my work home from home of nearly three years (May 2020–February 2023).

(You might recall I was at Fullstory, a SaaS company out of Atlanta, before. I am a shareholder there now.)

While at Mural, I built out content marketing and communications, managing everything from executive keynote presentations to assisting with a rebrand and "category creation" to writing and publishing a book. For nearly half of my time there I had no obvious manager, floating from CMO to CEO to CMO to CEO. It was wild. Too many things to mention.

It was a challenging three years. I learned a lot. Got a lot of XP.

I hope Mural and FullStory succeed, though I know fewer and fewer folks there these days.

Really, that's one of the problems with these tech companies. You could call it burn out, but you might as well call it burn up. As in, you're there, you fuel the growth of the business, you leave, and little evidence remains. Mostly ashes. Memories.

When the work is fully remote, well, it's stranger still. Like so much in our modern time, we see the clear benefits of technology, but we struggle to understand the hidden, abstract, long-term costs.

And if you didn't catch it, I wrote a book that hints at these problems last August: Exec on the Desk.

The present, Spring 2024

About December 2023 I decided to have a go at building out my own marketing practice.

So I founded R-ght. I started leaning into my network, talking to folks, bidding on projects. As anyone who has done this will tell you, this is a fun rollercoaster experience. I got various leads. Some were incredibly exciting and others more raw work.

One of my leads took me to a remote monitoring and management (RMM) software company for connected products called Canopy.

What is RMM for connected products?

What is RMM for connected products and Canopy?

Canopy provides remote monitoring and management software for B2B connected products — like self-checkout kiosks, digital signs, access control boxes, and even golf simulators.

Unlike "RMM" for IT — used to manage corporate tech like laptops, servers, and phones — Canopy offers mission-control, backend software to technical support and product teams. Canopy's RMM software acts as an agent for thousands of devices to be controlled remotely.

For example, Canopy makes it easy to remotely fix and upgrade that self-checkout lane you use. That way, it doesn't sit broken for days (or weeks), angering harried shoppers and store employees.

B2B connected products are pervasive, like it or not, and most of these remote devices require some serious backend magic to stay working.

So Canopy helps the makers of these devices weave software, hardware, peripherals, etc. together in a way that "just works" (to borrow on Steve Jobs' favorite phrase).

How I ended up at Canopy

You see, I got to know Canopy. I figured Canopy might become a client for R-ght.

Well, a couple months go by and out of nowhere they're asking me to lead up their marketing efforts.

So I took them up on their offer: I joined Canopy as Vice President of Marketing three weeks ago.

This is a great opportunity. There's much to do.

Unlike Mural or Fullstory, Canopy is the smallest company I've ever joined. It's also quirkily traditional, having its roots in professional services before becoming a software company two years ago.

Presently, I'm adjusting to a hybrid work setup. This is taking some time — literally. On those three days a week I trek into the office, I lose about five hours in total. It's the time to drive and all the time to prepare to head in.

But it's got benefits. Talk to me about it in six months.

Now what about R-ght?

Yeah, so about R-ght. Though the business didn't ever catch its stride, I'm happy with what I created:

Please go to www.R-ght.com and subscribe by email. During the days I was building out the business, I went ahead and built out some significant articles on concepts that nearly everyone would benefit from understanding:

• Agenda-setting theory: Understand what might be the most important concept of Internet existence — how media influences what you think.
• What you see is all there is: Daniel Kahneman's most important idea, apart from things like prospect theory, the focusing illusion, and other ideas, of course.
• The Anxious Generation Review: Jonathan Haidt's latest book

I want to keep going. R-ght scratches an itch. See you there?

The future you make

My beard grows grey. Time moves on. One job changes to another.

Life!

If you still keep up with me here, drop me a line sometime.

You can now speed run from blank page to fully illustrated book, published on Amazon, in 57 days (or less).

How do I know? Because I did it. And even taking nearly two months—and even having never self-published a book before—I estimate it only took around 80 hours of work to do. That's writing, illustration, and publication with zero outside help (apart from friends and family feedback). I also built a website and social media in this 57 days.

TL;DR

What did it take to get this done?

I had a solid idea—i.e. the concept "Elf on the Shelf meets corporate America." Mix it up with a backstory involving a magical consultant, the remote work vs. return to office dilemma, and all the typical absurdities of modern work ...

The story practically wrote itself. I suppose that's how the muse is, right?

The magic, for me, was in using AI + easy-to-use software + YouTube to provide the illustrations, the compositional power, and the self-publishing know-how to go from words to fully illustrated, laid out book across three formats.

The details

I have never authored and self-published a book before. But! I'm a creator with 30+ years creating under my belt—going all the way back to my childhood as an "artist." I was early in the "content" and web publishing game too. I've built websites to facilitate content creation for nearly 20 years now. Professionally, I make content for B2B SaaS companies, from blogs to ebooks to microsites and more.

That I could use generative AI (around 1500ish Midjourney prompts) to source my illustrative raw material.

Or that an easy-to-use tool like Canva would make it possible to create near-final layouts I could use for my hardcover (with finalization on Adobe InDesign,

Now I've created all kinds of content in the last 20 years. I could not have imagined this was possible a year ago or even 6 months ago.

But here we are. With readily available software (and YouTube for the blind spots) Exec on the Desk is out in the world (Get the book here).

✨

Timeline

Story ... I can do this (3 days)

June 27 — Begin a Google Doc and write the ~450 word story in 4 hours. Try Google Bard for ad hoc “rhymes with” help, as needed.

June 30 — 10 hours in, have rough layouts, having created illustrations using Midjourney for the first 7 pages of the book.

Start thinking, “I can create this entire book using AI in about 20 hours.”

Rapidly illustrating a book with AI (12 days)

July 1–12 — Learn that consistent characters for multiple illustrations require patience and lots of tinkering. 😅

Persevere with Midjourney to conjure up McKinsley and then a few dozen Execs.

In total, run between 1200–1500 Midjourney prompts (mostly remixes) to brute-force the creation of raw illustrations to further edit and compose into book layouts. Often do this “on the go”—i.e. running a prompt, walking away, coming back and remixing it, etc.

Note: Midjourney does not like to imagine a single banana. There are ways. 🍌

• Use Canva to compose illustrations and copy, laying out all the pages.
• Use Figma too for a plugin that helps with transparency, as needed.

Feedback + vacation (18 days)

July 13 — Share a draft of near-final book to friends+family for feedback. Based on feedback, revise and improve certain illustrations and compositions. Lots of revisions as perfectionist brain kicks in.

The publishing process (24 days)

July 31 — Begin creating print-ready book for self-publishing on Amazon KDP + IngramSpark.

Make lots of mistakes learning the details of layouts and bleed. Also learn and apply the basics with Adobe InDesign. Thankful for YouTube.

August 7 — Submit proof to IngramSpark. 9 days later receive physical proof of hardback book from IngramSpark to review. 🙌 Had one major layout improvement to make, which added 2-3 days to revise and approve a new proof—but I didn't even bother with a new physical hardcover proof.

August 18 — Create ebook and paperback for Amazon KDP, order paperback proof.

August 22 — All books confirmed live on Amazon

August 23 — Launch day 🎉

You have a genie in your pocket, technology offering to make your dreams a reality. Simply rub open your phone and tap away:

Need something? ... Amazon
Directions? ... Maps
Questions? ... Google, DuckDuckGo
News? ... 𝕏
Entertainment? ... TikTok, YouTube, Netflix, Instagram
Work? ... Email, Slack

For whatever you'd want to do, there's an app for that.

But there's a catch. Every gift from an app comes with a hidden cost.

The cost is buying products you don't need.
The cost is bewilderment about places.
The cost is naive belief in search results.
The cost is distorted facts as news.
The cost is losing common experiences.
The cost is bullshit work that never ends.

The benefit is clear. The cost is not. And the cost is still more than you think.

Apps bind you.

They determine how you can interact.
They deem what can be important—and what can't.
They set what you can see and what you can't.
They control who you can communicate with and how.

Apps constrain the possibilities, and by constraining, they change your capabilities. They change how you think. They set the table for what you can even think about.

Apps frame our existence today.

And everyone complies by simply opening them. We extend our hands and put the shackles on ourselves, the handcuffs so obvious that we are blind to them.

But there's hope.

The reign of apps exists only as long as you accept the bind. Realize the costs and constraints and throw off the chains.

Wake up. Wake up your family and your friends.

The technological trinkets and quick fixes are junk that's not worth the cost.

Usual frame: There's an app for that.
Reframe: Apps are traps.

See also an update to the parable of the blind men and the elephant — i.e. how you can hold an elephant in your hand.

Inspired by Scott Adam's Reframe Your Brain.

They keep saying if you want serendipity, you have to go to the office. Maybe all it takes is having a little fun with friends.

Exec on the Desk all started with a Slack message. A group of former, mostly marketing co-workers all regularly keep up with each other over a shared Slack instance.

One morning I shared a screenshot of a job posting from an Atlanta-based company that, while little known, makes a remarkably well-known Christmas product — i.e. magical, shelf-sitting elves that keep an eye on little boys and girls for Santa. These elves get up to all sorts of hijinks around the house, which kids love, and some parents love and others hate. (If you know you know.)

I shared this job posting over Slack, and a friend quickly responded with what he imagined it'd be like to work there:

"They will install an elf in your home office to report back your daily deeds to their Purity Board of Appropriate Behaviors"

That's when an absurd idea was born, the "Exec on the Desk"—a micro manager for knowledge workers everywhere, loyal to companies, always there to keep you productive and on task, in or out of the office. 😳

Next thing, another friend creatively mocked up a "manager doll" in Midjourney.

The synapses were firing. The muse was at work. That's serendipity.

From these humble but quick beginnings, Exec on the Desk was born. By midmorning, we'd joked about how the little Execs would work:

👉 "Add that extra 'fun' to work-from-home with a mini boss permanently scrutinizing your every action. Complete with the typical furrowed brow and canned corporate phrases."

👉 "Can't get time to talk over a tricky problem with your manager? Just tell the Exec on the Desk! Raise issues—complain all day long!—the Exec on the Desk will listen to it all and not do a damn thing about it!"

Soon I'd grabbed domains, imagining how to play out this silly little idea. All of this happened 90 days ago now. And truth be told, I didn't have the chance to do much of anything after that first day, being the last day of school and the beginning of summer break ... until a month later.

And that's when I drafted the story, putting words to digital paper, going from idea to publication of a book in less than 90 days—with the bulk of that done in 57.

Uncertainty is all around me. Not only do I not know what the day will bring, what the weather will be, or what surprises await behind every corner, but even the people I engage with! They are all unpredictable.

This is the nature of life. And while some level of unpredictability brings novelty, surprise, and excitement, too much uncertainty terrifies.

Modern life exposes me to a never ending stream of information bringing with it more uncertainty. Like the theoretical “butterfly effect,” events occurring around the world insist on proclaiming themselves to my world—whether it’s through social media, the news, or through the rapid proliferation of a novel virus literally crossing oceans in to infect my community …

Drowning in so much information paradoxically makes it harder to know what to do, what to think, how to live. What do I do about a novel virus? What do I think about the events in ________? How do I cope with knowing the suffering of human beings a world away? How do I quiet my uncertainty about the climate? About population growth? About the food that I eat?

On and on the uncertainty goes.

Today easy answers to all this uncertainty are available on demand. But there’s a problem. A decade ago I wondered about the problem of “confirmation bias”—that Google offered a way to confirm whatever strange idea I had. Today, I need not wonder. You can find any answer to life’s most uncertain questions. The right diet? Find an army of people who proclaim “_____ is the way, the truth, the light!”

Answers to uncertainty are everywhere and everywhere they contradict. See the people who are vehemently pro-[______], and see their enemies who are as dogmatically anti-[______]. Both sides, all sides, believe they know the truth. They believe with absolute certainty.

And so much certainty leads to more uncertainty.

The dogmatism cannot be trusted because paradoxically it is a sign of uncertainty. No one rages about what’s true. What’s known as true is not up for passionate debate.

What's true is apparent. What's true is certain.

So the dogmatism is a sign. It’s a sign many are now controlled by a dependency—the need to be certain.

So it is that desiring certainty goes from a natural, useful tendency to something more pathological.

And the pathology is now cultural. Modern man believes he can solve the riddles of reality. What can’t science tell us about the world? The universe?

Don’t adhere to a scientific world? That’s okay: What does your preferred God tell you is the answer?

Priests, experts, research, religion, answers, dogmatism … as far as the eye can see. If you want answers, you will find them.

What will make you happy? You do not know. But if you insist, someone, some product, some way to know will present itself, and you will accept it. Because you need to know.

How do you manage uncertainty? At the core, living in a world where you don’t have the answers, where we can’t know the answers, where the answers so strongly believed are probably—certainly—not the right answers …

How do you live this way?

And if you opt for certainty, the certainty of some system, what do you give up along the way?

I’m afraid we’re all going cyborg.

That might make you think of Luke Skywalker with his bionic arm or Darth Vader. Maybe it’s The Six Million Dollar Man (well before my time) or some blend of The Terminator. A cyborg is just a mix of man and machine where the machine—the technology—extends the man.

Man and machine.

Do you see what's before you? That screen you’re staring at, the one you’re holding in your hands, the one sending information directly to your brain through your eyes, the one doing your bidding through taps, scrolls, and swipes ...

That’s your extended mind.

• When was the last time you went anywhere you’ve never been before without using an app to tell you how to get there?
• How do you get information?
• How do you order products?
• How do you broadcast your life, your thoughts?

And the more we rely on our phones to extend ourselves into the world, the more like cyborgs we become. Yes, the interface between our extended selves is clunky—synapses mediated through glass, WiFi, camera sensors, speakers and screens. Yet it’s your extended self all the same.

Reflect on that for a moment. How does that make you feel? And what what does it mean for you, for me, everyone?

Analog to digital

Real life is messy. You take in the world through your eyes, your feet, your smell, your skin. “Real life” is analog. It’s full bandwidth and continuous, all cylinders firing. You take in more information than you can process and your focus directs your mind. You send out more information through your body, your face, your actions and inactions. To the extent that you can “escape” from real life, it’s done by physically separating yourself from others. You can’t really shut it off. Though you try.

Digital is clean. You open an app. You scroll. You click. Your eyes take the information in through words and pictures. Digital is binary. 0s and 1s. So clean. You can only take in what’s there. Low dimensionality. Only what you want.

You want to engage with the world? Send out information, edited however you want. You want to escape? Close that app. (Or open another one.)

That space between

What about all that space between? What fills in the gaps between all the zeroes and ones?

That’s the question before us all. Because the more we engage through those extended pocketable and oh-so-pampered rechargable and inexhaustible brains, the more we reach out and touch a virtual world through the smooth touch of glass, the more we run from the real world, the more our minds must fill in the gaps.

And boy do they. Using whatever decompression algorithms we have, within the context of whatever mood holds us, under the pressure of news, anxiety, social feeds, personal philosophy, politics, whatever ... we decompress all that’s presented to us. We bring that digital into our analog space. And though it’s as lossy, pixelated, and full of artefacts, because it’s the only information we have, we take it as truth.

This is life today. Zeros and ones served out and served up to us, held up as truth like so many filtered selfies, not real yet reality.

We’re going cyborg. And we need to face this and try to understand it. Because at some point the machine takes over.

Why does that happen? And what’s lost along the way ...

Clayton Christensen, the late author of The Innovator’s Dilemma and former Harvard Business School professor, made the case that to understand what motivates people to act, you first must understand what it is they to need to get done.

You need to know the why behind the what.

Christensen first articulated this outcome-driven innovation in a 2005 paper for the Harvard Business Review titled The Cause and the Cure of Marketing Malpractice, writing:

When people find themselves needing to get a job done, they essentially hire products to do that job for them ...

If a [businessperson] can understand the job, design a product and associated experiences in purchase and use to do that job, and deliver it in a way that reinforces its intended use, then when customers find themselves needing to get that job done they will hire that product.

Christensen’s theory is known as the “Jobs” or “Jobs to Be Done” theory (“JTBD”) because it’s built around a central question: what is the job a person is hiring a product to do? What is the job to be done?

If you can solve the mystery of Jobs to Be Done, you can build the kind of products people love ... like milkshakes for breakfast.

How Do You Satisfy Your Hunger on Your Commute?

Professor Christensen told a wonderful story to illustrate the Jobs to Be Done concept.

It starts with a fast food company’s attempt to make a better milkshake. The fast food company took a classic approach. They identified their target milkshake-slurping demographic and sent researchers to analyze this audience's milkshake preferences. Unfortunately, once the fast food company began making new, evidence-backed and "better" milkshakes based on the research findings, they discovered milkshake sales didn't improve, at all.

What went wrong?

This milkshake story is so good and so well told by Christensen, it's worth the four minutes it takes to hear the late Professor tell the story (YouTube; alternatively, read the transcript of the milkshake story included below).

How do you satisfy your hunger on your commute?

Professor Christensen tells a wonderful story to illustrate JTBD theory. It’s about a fast food company’s attempt to make a better milkshake. Said fast food company took the classic approach. They identified their target milkshake-slurping demographic, surveyed them about their milkshake preferences, implemented their findings, and didn’t improve milkshake sales whatsoever. What happened?

Christensen tells the milkshake story so well that we recommend you give him a listen (4 minutes, YouTube). Alternatively, the story is transcribed below.

Clayton Christensen talks about milkshakes.

We actually hire products to do things for us. And understanding what job we have to do in our lives for which we would hire a product is really the key to cracking this problem of motivating customers to buy what we’re offering.

So I wanted just to tell you a story about a project we did for one of the big fast food restaurants. They were trying to goose up the sales of their milkshakes. They had just studied this problem up the gazoo. They brought in customers who fit the profile of the quintessential milkshake consumer. They’d give them samples and ask, “Could you tell us how we could improve our milkshakes so you’d buy more of them? Do you want it chocolate-ier, cheaper, chunkier, or chewier?”

They’d get very clear feedback and they’d improve the milkshake on those dimensions and it had no impact on sales or profits whatsoever.

So one of our colleagues went in with a different question on his mind. And that was, “I wonder what job arises in people’s lives that cause them to come to this restaurant to hire a milkshake?” We stood in a restaurant for 18 hours one day and just took very careful data. What time did they buy these milkshakes? What were they wearing? Were they alone? Did they buy other food with it? Did they eat it in the restaurant or drive off with it?

It turned out that nearly half of the milkshakes were sold before 8 o’clock in the morning. The people who bought them were always alone. It was the only thing they bought and they all got in the car and drove off with it.

To figure out what job they were trying to hire it to do, we came back the next day and stood outside the restaurant so we could confront these folks as they left milkshake-in-hand. And in language that they could understand we essentially asked, “Excuse me please but I gotta sort this puzzle out. What job were you trying to do for yourself that caused you to come here and hire that milkshake?”

They’d struggle to answer so we then helped them by asking other questions like, “Well, think about the last time you were in the same situation needing to get the same job done but you didn’t come here to hire a milkshake. What did you hire?”

And then as we put all their answers together it became clear that they all had the same job to be done in the morning. That is that they had a long and boring drive to work and they just needed something to do while they drove to keep the commute interesting. One hand had to be on the wheel but someone had given them another hand and there wasn’t anything in it. And they just needed something to do when they drove. They weren’t hungry yet but they knew they would be hungry by 10 o’clock so they also wanted something that would just plunk down there and stay for their morning.

Christensen paraphrasing the commuting milkshake buyer:

“Good question. What do I hire when I do this job? You know, I’ve never framed the question that way before, but last Friday I hired a banana to do the job. Take my word for it. Never hire bananas. They’re gone in three minutes — you’re hungry by 7:30am.

“If you promise not to tell my wife I probably hire donuts twice a week, but they don’t do it well either. They’re gone fast. They crumb all over my clothes. They get my fingers gooey.

“Sometimes I hire bagels but as you know they’re so dry and tasteless. Then I have to steer the car with my knees while I’m putting jam on it and if the phone rings we got a crisis.

“I remember I hired a Snickers bar once but I felt so guilty I’ve never hired Snickers again.

“Let me tell you when I hire this milkshake it is so viscous that it easily takes me 20 minutes to suck it up through that thin little straw. Who cares what the ingredients are — I don’t.

“All I know is I’m full all morning and it fits right here in my cupholder.”

Christensen concludes:

Well it turns out that the milkshake does the job better than any of the competitors, which in the customer’s minds are not Burger King milkshakes but bananas, donuts, bagels, Snickers bars, coffee, and so on.

I hope you can see how if you understand the job, how to improve the product becomes just obvious.

Source: Clayton Christensen, YouTube

“Let me tell you when I hire this milkshake it is so viscous that it easily takes me 20 minutes to suck it up through that thin little straw. Who cares what the ingredients are — I don’t.

“All I know is I’m full all morning and it fits right here in my cupholder.”

Solving Jobs to Be Done With Empathy

How we confuse consumers with consumption.

Christensen’s milkshake story illustrates how asking a direct question—“What would make our milkshakes better?”—is a fast way to arrive at the wrong place.

Should we be surprised? Are milkshake buyers little more than their demographics? Of course not. "Demographic determinism" leads us to a dead end because demographics fail to predict intent.

And in this case, confusing the milkshake consumers with what they hope to do (Satisfy hunger, add excitement to a boring commute, or whatever they hope to accomplish), will result in developing “a one-size-fits-none product,” as Christensen put it. Worse, you can bet this product will do little to nothing for sales.

Meanwhile, a business organized around solving for the actual needs of consumers has a clear reason for being because it’s those needs that drive a customer’s behavior in the first place.

Remember: The consumer is not the same as what they consume.

It’s All About Intent! And Intent Starts With Empathy

Christensen's Jobs to Be Done framework brings to our attention something we all know: intent matters. Everyone has reasons for the choices they make—a need to meet, desire to fulfill, objective in mind, whatever! Shakespeare captured this quintessential insight about human nature some 400 years ago while writing Hamlet: “Though this be madness yet there is method in it.”

If you want to be effective at your job, you need to identify their job. You have to discover what need, desire, or objective they hope to satisfy.

Finding the method behind the madness—that is, the intent of the customer—begins with empathy. Whether you're a product manager, a support professional, a salesperson, marketer, whatever, if you want to be effective at your job, you need to identify their job. You have to discover what need, desire, or objective they hope to satisfy.

Empathy grounds us with a deep understanding of the customer's mind, putting us in that mindset so we can discover intent.

And when it comes to lovable products and customer experiences, you must direct that empathetic understanding toward solving for that intent. And you have to do it better than anyone else.

This is why it's so important to question whether the features we're building or product branches we're developing will do the job better than the nearest alternatives.

Because if the product being developed is built without customer needs in focus, you might find we’ve developed the most amazing product ... only it'll be one that no one wants.

People don’t want to buy a quarter-inch drill. They want a quarter-inch hole!

—Theodore Levitt, Harvard Business Professor

Using Jobs to Be Done to Build More Perfect Products

You can only find the right answer if you ask the right question.

So now you've got a firm grasp on Jobs to Be Done. How do you put it to work? How do you tap into empathy and discover customer intent?

Applying JTBD to understand consumer needs can be as simple as asking, “What did you turn to the last time you needed to do this?”

In Clay Christensen’s milkshake story, this question helped consumers to think back on a previous time they were in the same situation and needed that specific job done. That is, the milkshake buyer needed something to satiate their hunger—or their boredom—on their long commute to work.

It sounds so easy, except we all know how hard it can be to uncover exactly what jobs a customer needs doing.

Which is why we've put together a handful of questions you can ask that can help reveal clues to solve the JTBD mystery.

1. The Switching Question—"You're Fired!"

Is your product so good that your audience would ‘fire’ their current product in order to hire yours?

Reflect on the product you “fired” before hiring the current product. You can tease out why customers choose your product or service by considering what the customer used before they switched to your product. From there, thinking about the “why” can help clarify just what job needs doing.

The “fired” lens in the Jobs to Be Done framework can be used to understand how many once-successful businesses were displaced by competitors that simply did the job better. Examples:

• Netflix doing the job of Blockbuster — “I need something to entertain me ... but I don't want to work too hard to find it.”
• Uber, Lyft replacing taxis — “I need to get from point A to point B easily and painlessly.”
• Google — “I need to know ______ and I'm only willing to work so hard to find the answer.”
• Amazon — “I need to have ______ and I don't want to overpay for a product I'm not confident I'll like.”
• Smartphones — “I need _____” ... Truly smartphones are a JTBD powerhouse, fueling all kinds of businesses over the last 15 years.

Ask this critical question: “Is my product (or service) so good that my intended customer will stop using the product and make the switch?”

“What are people going to stop doing once they start using your product?”

— Jason Fried, Signal vs. Noise

Remember: If you can’t answer the “switching jobs” question clearly, could you reasonably expect a potential customer to?

2. The "WWYSYDH" Question

What does your product or service actually do for someone?

If you’ve seen the movie Office Space you certainly remember when “the Bobs” asked our slacker protagonist a simple question:

“What would you say you do here?”

This simple, straight-to-the-point question deserves some focused attention. If you articulate all the things the product actually does for a customer, you will paint an impression that will help you tease apart what job it is your customer is trying to get done.

Be both specific and general. The details matter more than you might think. The drill makes holes. The milkshake gives you food and it takes awhile to drink. Starbucks gives you energy and it also gives you a place to go. Make a WWYSYDH list.

Contrast your list with the product’s enumerated features. Do the features your product developed solve for the things on your list — the things your customers need doing?

If you’re struggling here, you might also try The 5 Whys. If you’re unfamiliar, this approach is simply asking and answering “Why?” where each answer you provide is further challenged by asking, “Why?”

3. The Hierarchy of Needs Question

Remember Maslow's hierarchy of needs? How does your product fill these needs?

Now it's time to go up a level. Think about Maslow’s hierarchy of needs. Christensen has written that, “With few exceptions, every job people need or want to do has a social, a functional, and an emotional dimension.”

• What social need does the product solve?
• What emotional need is being solved by the product?
• How will using the product make the customer feel?

While it may seem far-fetched to think of how a given product solves some intangible need of a customer, it makes sense: customers buy products for reasons (see above) that exist under specific circumstances (context). These reasons can be simple or incredibly complex. Meanwhile, because most of us don't question the underlying reasons for why we do the things we do, understanding how our behaviors satisfy our basic needs as human beings can be exceptionally difficult to articulate.

This is why the Jobs to Be Done framework can be extended to understand all sorts of things about others and yourself — from your career choices to your hobbies and relationships. You can ask yourself, “Why am I really doing ______? What is it I really hope to accomplish here?

Apply the Jobs to be Done framework introspectively and you may be surprised what you find.

Build More Perfect Produts With Jobs to Be Done

Now that you're well-versed in the Jobs to Be Done framework, take a second to look at your product roadmap. Does it lead to products that meet the specific outcome expectations of your customers? How could your product better fit their intent?

Evangelize the JTBD theory with your team members. Expect some lively discussion and at least a few "A-ha!" moments.

Apply the Jobs to Be Done lens to every business decision and you'll always have customers ready to hire your product for that job.

Note: There's a bit of thinking here. But it's thinking after doing.

The late Seth Roberts once wrote about his graduate school days, and how he got into self-experimentation. It was by way of the idea that, "The best way to learn is to do:"

Quoted from a 10 minute presentation by Seth Roberts (link long since lost to github, apparently)

Roberts practiced "learning by doing" throughout his life, always carrying out various experiments to see what he could discover.

It's a simple, intriguing idea: you can learn more by doing first than you can by thinking first.

Why might this be the case?

Ways Thinking-First Creates Problems

• Thinking adds unnecessary complexity before you've acquired the expertise born of experience, making it harder to interpret results,
• Thinking sets expectations, biasing analysis towards desired results, and
• Thinking is time-intensive, reducing resources that could be used doing.

It's not that thinking is bad. Rather, it's too easy for thinking to become un-tethered from reality. After all, "thinking" is just the running of simple simulations or models in our heads. Reality is far more rigorous and complex. Thus, by maintaining a bias to action (i.e. doing), we can stay grounded in reality.

Unfortunately, thinking-over-doing is pervasive in modernity, and the results aren't great.

Consider just a few (8) examples:

1. Our education system is built on thinking ... and horribly broken. The foundation of education is built on thinking over doing. School boards think through what subjects students should learn. Even when choice is introduced such as in college, there are enormous costs to trying a lot of disparate subjects.Not surprisingly, students get locked into fields of study only to learn when it's too expensive to do anything about it that they don't particularly enjoy their chosen major.
2. Thinking doesn't help you find a career. The same problem is seen with career choices. We think our way into a certain career versus learning what works and what doesn't work by simply trying out different types of work. We try to think our way into figuring out our passions. It just doesn't work.
3. You can't think your way out of your mental state. Or apply the idea to William Glasser's Control Theory. Glasser argues that it is difficult to impossible to change what we think or feel about something that happens to us. Our best course of action to change our mental state?Do something.
4. We don't know what will make us happy. Daniel Gilbert's Stumbling on Happiness. Gilbert makes the point that, "We insist on steering our [lives] because we think we have a pretty good idea of where we should go, but the truth is that much of tour steering is in vain … because the future is fundamentally different than it appears through the prospectiscope."Thinking through what we want is something we all do, yet it rarely is effective at leading to happiness. How often do we finally get what we want only to realize that the experience is not what we expected? This is a failure of thought.
5. The power of tinkering as a means of discovery. And as Nassim Taleb puts it, "Understanding is a Poor Substitute for Convexity" (See his paper on this — PDF).Nassim Taleb harps on over-reliance on thinking all the time. The Black Swan is essentially a book about hubris and the misguided belief that we can think through everything. (As another example, Taleb doesn't read the news because it formalizes thought, effectively handicapping our cognitive function by creating bias. Also, here's an old interview on EconTalk where Taleb talks about tinkering.)
6. The state. Or look at thinking over doing as it pertains to governments and political debate. Was there ever such an embodiment of preference for thinking over doing? Every government (generally) and every government program (specifically) is a thought-out experiment tested on a massive scale. Should it come as a surprise that governments and government programs are so dysfunctional?Observe how political philosophers consistently prefer thought to action, a la Folk Activism, dismissing attempts at trial and error or ignoring the importance of seeking new frontiers for experimentation, while arguing, "We've yet to see pure [ socialism | capitalism ]; therefore, you can't say it wouldn't work!"
7. Kids. I haven't read Bryan Caplan's Selfish Reasons to Have More Kids (Preface). However, in thinking about the question of children, two thoughts come to mind in relation to the doing/thinking problem (And both relate to Caplan's review of a study about how "Almost no one regrets having kids:"
   1. Couples who choose not to have kids have overthought the problem and will almost certainly regret their decision not to have kids.
   2. Parents who think they should only have two kids (for example) will likely end up wishing they had had more—it seems parents tend to think they should have more kids than they end up having!
   Having kids isn't like waking up and making an omelette, so I realize that this one fits into the doing-vs-thinking paradigm a bit loosely, but nonetheless, it's just another example of how thinking fails.

   (Since originally writing this I have had three kids! I still completely agree with the above sentiment.)



8. Life itself. Life is the result of trial and error performed on a massive scale and is ongoing. As complex as a DNA molecule may be, the individual building blocks are simple. So here's an example of doing (DNA replication) and simplicity leading to unfathomable complexity—life. Evolution is the triumph of doing and is clearly a thoughtless process.

Do More! (And Experiment Often!)

As Seth Roberts realized in his graduate days, "I should just do as many experiments as possible as opposed to trying to think of which ones to do." But why does doing first work better than thinking first? Perhaps it is because doing is fundamentally an iterative process: doing is trial. The idea of trial and error as a method of learning means making mistakes and learning from them.

Making mistakes and figuring out what doesn't work can also be desirable as evidence of absence. Perhaps it is the sheer number of trials that spur the creation of knowledge. Could it be that the more experiments, trials, and iterations, the greater the chance of winning the lottery and learning something truly worthwhile? Maybe so.

As a general rule (yes, exceptions surely exist!), consider putting thinking on hold in favor of action.

Stop thinking and start doing.

Follow whims, opportunities, gut instincts, and curiosities. Observe as much as possible. Expect failure and realize that it is through innumerable failed attempts that one can stumble on success.

Updated April 2019. Originally published April 16, 2009. With special thanks and gratitude for the late Seth Roberts.

There's a wonderful thing about the frontier. It's a place where the rules don't exist. Anything is possible ... so long as it sustains existence on the frontier.

America was a frontier—"The New World"—a place where humanity was able to experiment with new ways to exist as a society—ways forbidden by the prevailing powers in the Old World. Perhaps more than anything, frontiers lack structure and reigning institutions, regulations, and norms. It's within this vacuum that novelty has a chance.

The Internet, too, has been a frontier. A digital plane where new business models, new ways to engage and communicate, and more could all be tried.

Freedom is found on the frontier.

The tyranny of the status quo

And what's the opposite of the frontier but the rules, norms, and prevailing powers of the status quo? Ruling states, businesses, wealth, and more exert monopolistic constraints that choke out the possibility of alternatives. The chance for novel ideas.

It is the established order of things—the status quo—that makes it hard to think differently. So what do you do?

All is not lost

Thankfully, the status quo is stagnant ... systems wound up like a mechanical watch that can only work in a very calculated way. Rigid.

Over time, systems start opposing their proper purpose. They grow so large—or even so specialized—as to be inefficient, brittle, and unable to adapt to changing conditions.

This stagnation results in opportunity because the status quo can't adapt to changing conditions. And it's innate inefficiency means some are under-served. Before long, there emerges a possibility of new frontiers.

This is a cycle

It's this ebb and flow between the frontier and the status quo that we cycle back-and-forth, iterating and evolving over time. It's the way of evolution. It's the way of systems. It's the way of life. And it's been this way for millions of years.