Elle Luna: An Artist at Best or Designer at Worst?

Ever heard of Elle Luna? You’ve probably touched her work. She was a crucial designer behind three of the biggest apps in Silicon Valley – Medium, Mailbox, and Uber. Uber 1.0 was super ugly until she came around, Mailbox was built under her design lead, and scaled Medium from the earliest days.

Sounds like an accomplished, fulfilling career, no? Elle didn’t feel that way. She jumped from success to success never feeling content. She started having dreams about a white room with nothing in it, visions that she couldn’t escape. So she did the logical thing, and went to Bali for 6 weeks in order to find herself.

In Bali, she spent her time in a hut without walls, painting portraits of local villagers and discovering a love of textiles. The experience empowered her to pursue artistry full time, so she went back to San Francisco, found the white room of her dreams on Craigslist, filled it with paint, and has since left her designer days behind her entirely. Pretty heartwarming, right?

She even wrote a viral blog post about the experience that turned into a fan favorite book: The Crossroads Between Should and Must. Should is all the things that society says you should do, and Must is what your inner self says you must do. Needless to say Elle has embraced her Must, and she encourages many others to do the same.

It’s a fantastic parable for doing what you love. Girl works hard, hits the big time, isn’t satisfied, and quits the real world to go do what she loves. This is straight out of Eat, Pray, Love.

When I heard Elle’s story, I loved it. But then I saw her art, and the narrative changed. Her story morphed from a guiding light to a cautionary tale. Something about the whole thing just seemed inherently wrong to me. My greatest fear in life is that I don’t live up to my potential, and to me, the story of Elle Luna is exactly that.

I have no business telling Elle how to live her life. She’s happy, she’s making a living, she’s creating art, and what I think is completely irrelevant. I don’t mean to disparage her or what she’s doing. But her story is too perfect of a parable. not to share.

A Tale of Passion Pursued, or Potential Eschewed?

I don’t like Elle’s art. It’s not that I hate it – it just doesn’t speak to me. I think her moon banners are trite, her portraits unexceptional, and her sketches are ordinary at best. It’s professional art, but nothing special when compared to other professional art. That’s my opinion, and it’s moot, since she has an audience paying hundreds of dollars for it.

But that’s the thing – Elle didn’t start off as an artist. She was a designer, and a damn good one at that. Look at how gorgeous AND useful her app designs are. They’re pretty, simple, and effective. Few can deny the value that she has added to those projects. Meanwhile, I’m not the only one who doesn’t care about her art. Some love it, some don’t care, and most people aren’t affected; whereas her designs were unanimously praised, and used the world over.


As John Maeda phrases it above, design is the intersection of art and science (subjective and objective value in my phrasing), both beautiful and useful. She went from being a talented designer who positively impacted millions of peoples’ lives in the most meaningful of ways (reading, communication, transportation), to an unexceptional artist who makes a few wealthy art collectors’ lives marginally better. The value of her creations became subjective and limited in scope.

Must Is Easy When You’re Elle Luna

What if everyone did that? What if everyone chose Must over Should? It’s the classic artist utopia offered after the Singularity, when robots become capable of taking care of humanity’s every need, freeing us to become artists and do whatever we like (or Must!). But in the meantime, somebody needs to clean the toilets, take out the trash, and sell products. I doubt any of those are personal Musts, which means that if we all followed Elle’s lead, we’d all lose our jobs. And most people aren’t as privileged, successful, or wealthy as Elle Luna to make the artist jump sustainable.

Would she have been a successful artist if she didn’t have that glowing design career behind her. What if she starting making art right after high school instead of going to IDEO? Would anybody care? Would she be successful? Would she love her life more? Those are big what-ifs, but unless you have 3 triple A apps to your name, they are the questions you will be grappling with, not Should vs Must.

Here’s another angle – what if her art was as successful as her designs? What if her personal brand was as well known as Ubers’? Art offers a very different kind of value than scientifically useful design, but it is value nonetheless. Making something people like to look at isn’t quite the same as streamlining daily processes, but both have value. Indeed, the value of a designer is a commodity, while the value of an artist is not – any talented designer can streamline a process, but the work of an artist is 100% unique.

An Artist at Her Best, or a Designer at Her Worst?

The tale of Elle Luna can be told as that of an artist embracing her true calling after years of languishing under the Man, or it can be told as that of a designer throwing aside her impressive talent for helping others in order to help herself. I see it as the latter, but I can understand why someone would see it as the former.

I come off as an arrogant, unfeeling Objectivist in this way. Who am I, or Ayn Rand for that matter, to tell Elle or anyone how they should spend their life? Then Rand is just another Man doling out Shoulds and holding us back from our Musts, which is not what I believe. I’m all about Musts and loving your job. But I’m also all about adding value to society.

If Elle is happy as a designer and ecstatic as an artist, should she forego that extra joy in order to pay her dues to the rest of the world? She owes us nothing, but if the Venn diagram below is apt, art is more of a passion than a purpose. (or maybe I’m just a fogey businessman who doesn’t understand the value of art).


Can Must Come With Should?

If Elle’s lifestyle is happy, fulfilled, and sustainable, that’s all that matters. It’s once she tells others to do the same that get uncomfortable. I disagree because I value design for many over art for the few, and think that it’s simply not possible for most people to embrace their Musts today (without her star power).

Perhaps the right answer is a balance. For now, everyone does as they Should, and need more Must in their life. But overcorrecting the scales and going full Must is just as bad. Perhaps to live well, one needs both Should and Must.

An artist who loves making art nobody else loves is just as bad as a scientist who spends their life writing theoretical papers with zero applications. Both love their lives, both struggle to get paid, and nobody (other than them) cares. If everyone embraced their Musts (Kant’s categorical imperative), the majority would be making stuff nobody else cares about. Isn’t a world where we’re making stuff we love to make that’s also loved by others the best possible? That’s the world I’m groping for.

Is Elle Luna in that world? I suppose she is, since she’s enriched my life and millions others with her design, her story and (apparently) her art. And if she inspires even one more person to embrace their Must rather than their Should, she’s a true hero.

Weekly Review #89: Burning Man on boats, Millionaire timeblocking, and plagiarized romance

I attended an event called Ephemerisle this weekend, which is basically a libertarian Burning Man on boats in the Stockton Delta. Which means you get a whole lot of seasteaders along with the normal Burner folk, and a few Stockton dirtbags who live on boats full time. Naked people, makeshift boats, and salty joke abounded. I rode a swing on a spinnaker sail, which is something I’d never even seen before, and was so fun it seemed like it should be illegal.


Marketing Stack is a curated directory of startup marketing tools - bookmarking that for sure! Likewise, Gigantic post on Knowing which SaaS metrics really matter and how to measure them is a bible.

My friend Vishal opines that Marketing Shouldn’t Be a Dirty Word in Silicon Valley. The smartest young people go into consulting because marketing gets a bad rap. And when hiring marketers people have no idea what to ask for. I hadn’t thought of that!

TechCrunch analyzed all the Billion dollar companies so far and has some learnings to share - founders are older than you think, on average.

Joseph Walla has grown a company to 41 million in revenue, twice. Here’s ten tips he’s learning along the way (charge ASAP!)

Alex Moore says there’s nothing wrong with email, just how we’re using it. Stop spamming, use ccs correctly, and we’ll be fine.

Dear VCs – stop asking for future revenue projections. Sincerely, Dave Mcclure (and everyone else)


Forbes notes that few millionaires use todo lists, but many of them do time block their days. That’s something I’ve noticed with the Habitual Hustler interviewees as well….

Ben Casnocha has a thoughtful piece on the US, Germany, and Europe. 

  • Does a Facebook engineer who makes it easier to turn your profile picture into a gay flag (as happened after the Supreme Court ruling) possess more power in shaping social/political issues than a high ranking elected official who gives a speech on the same topic? The levers of power are changing.

Silicon Valley founder Ryan Allis has a gigantic 1000 page plus Slideshare on everything he’s learned. Agree with the general message, but he’s maybe a little too overzealous?

Chandler Bolt dropped out of college to make a school to help people self publish, and it’s on track to make 1 million. Biz insider is getting pretty good at this rags to riches stories, I’ll give it that.

Remember the scammy Kindle tactics from last week? The author tried it out himself, with an interracial romance book. Big response! So big that the romance writers came out of the woodwork to pillage him.


Cotopaxi festival looks interesting – it’s a mobile powered social scavenger hunt with proceeds going to charity. I bet there are more classic games out there waiting to be leveled up by smartphone integration.

The Great Discontent interviews creative people about failure, and it’s kicking ass. Why? Vulnerability is exciting.

Before Reading, Ask Yourself Who It’s Written For

In Ryan Holiday’s excellent book Trust Me I’m Lying, he relates his alarming experiences as a Marketing Director at American Apparel, the infamous yet successful company. One of the main takeaways is how online news is mostly poisonous edutainment, although everyone treats it as important. In order to avoid getting caught up in the never-ending cycle of page views, clicks, and profit, he recommends one simple rule:

What Do I Intend To Do With This Information?

Before reading , ask yourself “What am I going to do with this information?” Simply being conscious of your intentions as a reader will filter out the things you really want to read from what is merely in front of you. 

As a reader, you may read something to learn more about something, or for entertainment, or because you trust the writer to put out great content. In other words, the information is either intrinsically pleasurable, or helps you attain some knowledge based goal, or you absorb it because you know the writer consistently puts out material that is one of the above.

It’s okay to read for entertainment alone, of course, as long as you are aware that that’s what you’re doing. If you’re reading entertainment and treating it as useful, that’s when things start to get dangerous. At least with a reality show the line between fun and fact is more clearly delineated. Ryan’s question helps you be intentional and aware of the info you’re putting into your head.

What Was I Intended to Do With This Information?

This is a great heuristic, but I think there’s another equally helpful side to the question. “What does the writer want me to do with this information?” Why did they publish this? What were their intentions? The answers there are more insidious. 

There are plenty of great reasons to write. It’s a fun hobby, it helps you examine your thoughts outside of your own head, and it is a good way of transmitting information to a specific person. But there’s only one reason to publish – you want people (anyone!) to read it. The question is why?

There’s only two reasons – either they think it’s something worth sharing (entertaining or artistic for fiction, helpful or important for nonfiction), or they stand to gain from the reader having read it. They’re either selfless or selfish. You benefit from consuming the information, or they benefit from you having consumed it, whether in the form of page views, clicks, conversion, or something as nebulous as ‘thought leadership’.

Needless to say, you should stay away from the stuff that exists solely to benefit the author. When they care more about page views than readers, thought leadership than trust, or conversions than visitors, then you become a peon, of no worth to them beyond the attention you bestow. Why read that stuff when you can read things that benefit you?

Content Companies Explicitly Milk You

For established content producers, the moneymaking methods are obvious. Companies exist to make money, theoretically by getting paid in proportion to the value they provide to society. Content mills like Buzzfeed and Upworthy value your clicks over your trust, so they churn out mindless fluff scientifically formulated to make you share. Again, there’s nothing wrong with entertainment, but when the creator cares more about you sharing it than enjoying the piece itself, your time is better spent elsewhere.

Publications with  ‘journalistic integrity’ like the New York Times value your continued attention more than your shares, so they stick to long-form well researched content.  These writers take great effort to gather the information, create a narrative, and present it to you cohesively. They’re writing it because they think it’s a story worth being told, not just to make money. But in the end, they need you to keep coming back in order to stay in business.

New Web Personalities Vary

The new web personalities play the same game, but with varying strategies. Some place the reader first, like Leo Babauta of ZenHabits. He makes business decisions using the maxim “Would this be better for my readers?” That’s why his websites are clean and ad-free – his goal is to make the reading experience pleasant. This engenders enough trust to keep the readers coming back, which allows him to make a sustainable living off of his writing using indirect methods like affiliate links. His readers trust that he is sharing what is best for them, not for him.

Meanwhile, there’s plenty of examples of scammy internet entrepreneurs who use direct marketing tactics to make as much money as possible off of you while providing minimal value. You can see them from a mile away – every word of their blog is copywriting intended to get you to buy something, their sites value annoying pop-ups over a quality reading experience, and their information products cost thousands of dollars. Many of them really do provide value, but it is rarely proportionate to the money you pay.

The line between scammy internet author and honest blogger gets blurred with people like Tony Robbins and Joe Rogan, but whether you think they’re writing for you or for themselves is up to you. I think in general that personal blogs are better places to find content with the reader in mind than corporate ones. Many startup founders maintain blogs just to share their learnings, and make nothing off of them. They’re sharing what they’ve learned, and nothing more. Whereas any corporate interest is trying to make money off of you one way or another.

It’s true that some publishers have journalistic integrity, and aren’t trying to milk you for all your worth. Again, it’s up to you to decide for yourself. But at least ask the question – who was this written for, me or them?

Weekly Review #88: Sketchy Kindle ebooks, better headlines, and the self as an illusion

I wrote a piece on e27 about why it’s so hard to disrupt email, check it out.


Crayon - lets you see what old website copy looked like, see how it has been optimized

Here’s 1000 words that elicit special responses when used in headlines - so use em all!

Hilarious startup webcomics are here - “I’m not unemployed, I’m pre revenue”


Confessions of the underground world of Kindle ebooks, part 1 – this guys makes bank plagiarizing public domain works using ghostwriters on Amazon self publishing, and here’s how. Similarly, This woman’s story about leaving her job to start a book editing marketplace is fascinating.

Gigantic post about what Ben Casnocha learned from 10k hours with Reid Hoffman offers plenty of insights that anyone can learn from.


Sam Harriss on why the self is an illusion gets trippy real fast. But is it actionable? How would I act differently if ‘I’ don’t exist?

Alan Watts on how to live with presence  offers advice we can all use, every day.

This Drone delivering drinks in a crowded restaurant is surprisingly stable.

Have you realized you control your life?

from Wackystuff on flickr

When did you realize you control your life?

I’m serious – have you realized it yet? I hope you have. Many people go through their entire lives without realizing it.

In youth we are shepherded through the years by school, and in adulthood we are shepherded to work by the need to pay the bills. There are vacations and weekends where you have a moment to breathe, during which you may ask yourself ‘What would I do with my free time once I got tired of diversions like drink and entertainment?’ But then Monday comes around, and you push aside these errant thoughts in favor of more pressing matters. There’s too many Hows and Whens in your life to think about Why.

Thus it is a sad reality that many people don’t realize they control their  lives until retirement, when they suddenly have all the time in the world without many obligations. Free from the tyranny of being told what to do, they realize that they are capable of whatever they want, and moreover, they always had been. They realize that money, skill level, location, and network were all self-imposed restrictions that dissolve once you attack them in earnest. Even bad health from being elderly is a false barrier.

The worst part is the opportunity cost, the knowledge that you spent your whole life needlessly catering to the demands of your parents, your professors, your boss, and your spouse when you could have catered to yourself all along. You could have filled your life with ‘mini-retirements’ (as Tim Ferriss calls them), satisfying your bucket list throughout life in spurts rather than all at once near the end. The sooner you realize you control your life, the more life you have to control.

If you don’t take control of your life, somebody else will. And their plans for you will never compare to the ones you dream up. However, breaking out of one’s powerless default reality is not easy. It’s cozy, comfortable, familiar. Taking the red pill isn’t easy, and ignorance is bliss. An active lifestyle takes some work, but it is so much more rewarding than a passive one. The first step is to step off the rails, either by not doing something you are expected to, or by doing something nobody expects you to.

Eschewing college is one way to start

During a recent Thiel Foundation Summit, I met many smart young people who had all realized that they were in control of their own lives far sooner than most. Indeed, the very act of deciding not to go to college is evidence of life control, since college has become the default action.

Anything other than the default action (when taken intentionally rather than contrarily) is probably better for you. My blogger colleague Tynan once wrote about how he looks down on people who live ‘normal lives’, because it is evidence of a passive life. What are the chances that the default choice of the rest of the world is right for your unique needs as an individual? The chances are microscopic – what likely happened was that you didn’t actually think it through, and instead took the easy option that everyone else does. 

Once I realized how all these active people had in common, I took delight in figuring out exactly when their life took a turn for the intentional.  I’m curious about such events, because if we can help more people gain control of their own lives, the rest is easy. Once a person is empowered with a sense of agency and curiosity, the rest is up to them. As the saying goes, ‘give a man a fish and you feed him for a day; teach a man to fish and you feed him for a lifetime.’ I say “Show a man the reins of your life and you inspire him for a day; but give a man the reins of his own and you inspire for a lifetime.”

Their answers varied. One guy hated authority from the start, and so he categorically disregarded anything people told him to do. Another read a book about Ben Franklin and was inspired by his eccentric lifestyle. Another wanted to make more money and impact than he felt could be achieved normally, so stepped onto his own path.

Others found gap year scholarships that allowed them to escape the rat race for a while and really think about where they were going. One guy just noticed that he was more productive in the morning, even though he knew he wasn’t a morning person, and the desire to find out why was enough of an impetus to start.

For me it was my year abroad in Barcelona. I realized that I could travel anywhere; that nothing was holding me to one place. If I could go anywhere, I could be anyone, and if so, why not be the best person I could be? Everything since then has been a quest to find out what that looks like.

“I never wanted what I thought I did”

One answer was repeated again and again. “I finally got what I thought I had always wanted, and I realized that I had never truly wanted it in the first place.” This, to me, is the shortest and most elegant way to put it, and an analogue for life in general. It is the same sentiment that every unfulfilled retiree feels. They got what they wanted and realized it wasn’t truly wanted; instead it was something they were told to want.

It’s not money you want, it’s freedom. It’s not a conventionally beautiful spouse you want, it’s someone you find attractive who loves you for who you are. It’s not the degree, job, qualifications, or any other bullshit credential that you need, but rather the ability to deliver what you promise.

Society presents distorted views of what is truly wanted, as we create proxies and abstractions of the real things in question. It’s up to us to realize that they’re presenting the reality they want you to see, and all you need to do to get the life you prefer is to see the reality that you want to see.

How can we help people take control?

So what’s the real life version of the red pill? What would a bootcamp designed to make you take control of your like look like?

There’s the scholarship option –  pay for a young person to spend time on their own figuring out what they want to do free of the need to pay bills. Perhaps right after high school or college – all they need is some breathing space to figure out what they want, exempt from the stated desires of the rest of the world. You could do this in college, but theres drinking and girls and grades and all sorts of frivolous distractions that would prevent people from really looking at themselves (or at least this was my case).

There could be a scholarship that does not give money, but rather experiences. Someone has wanted to vacation in the Bahamas all their life? Own a motorcycle? Go skydiving? Make it happen. This service could act as a sort of Make A Wish foundation for those who are not about to die. Allow them to fulfill what they always wanted, and make them realize it was never a real end goal. And since it was not, start them questioning: what is?

These are expensive solutions, though they are likely to have higher success rates. The cheaper routes could entail motivational speakers inspiring people in person, or publishing an inspiring book (like The 4 Hour Workweek or Black Hole Focus) that shows others how live the way they’d like to. Yet these solutions are not individualized to each person’s experience – they are one size fits all. There’s a big difference between giving a person the power to control their own life and exposing a person to someone who already controls their life. The former can only be done internally, but perhaps the latter can ignite the former.

The ability to recognize yourself as the sole purveyor of your personal destiny, and the next step of figuring out what you want that destiny to be, are the most powerful tools that you can give a person. Why don’t we give it to more?