How to Design a Different Future

Current Status: Ahead is a long read, so I’ll get out of the way as quickly as possible. I’m sitting at my desk on a Friday afternoon, drinking an ice coffee that somehow tastes like chocolate, and listening to The Lounge Lizards on the office Sonos. Bout ready to bounce for the weekend.

CB, June 3, 2016

Entrepreneurship doesn’t mean what you think it means. Not necessarily, anyway. It’s not about a particular method of creating something. It’s not about startups. It’s not about IPOs. And for the love of God, it’s not about disruption. It’s not even about millions billions money, really. It’s fundamentally about risk-taking and finding new and interesting ways to create value. And as we all know, value is a relative measure. Which means that though we cannot all be founders or owners, we can all be entrepreneurial. If we want to. But that — desire — must be true. Our culture has made an idol of entrepreneurship” to such a damaging degree that far too many people make choices that lead to waste and despair, when — and I truly believe this — they’d have been happier and more successful leading a very different kind of life. In fact, I think more people pursue leadership” and management” and the sorts of top-rung-of-the-ladder roles that are disproportionately rewarded in our culture than ever should because they are not given enough alternative models of success nor the proper chance to reflect upon what would truly be best for them. We’ve made an excellent business of rushing ourselves to market and we accept far too much collateral damage.

My perspective on this isn’t that unique. But it’s informed by my own path, along which I’ve come to rethink what it means to live and work many times, and will no doubt continue to. What I’d like to share with you is how my own perspective on entrepreneurship” has evolved, and offer a critique of the homogeneity of the contemporary model of the entrepreneur.

A little over a decade ago, I started my own business. Not knowing any better, I named it after a project I did in my final year at RISD. So I had my own business (Look at me, I’m an adult!) but it had a long, embarrassing, trying-way-too-hard-to-sound-smart name (nope, very much still a kid).

My business was design. So, pretty much whatever. Logos, identity systems, brochures, websites. I even made a commercial. The what didn’t really matter much to me then. It was just exciting to finally be paid! As a design student, you learn work all the time, so, naturally, I continued this way of life. I worked all the time. But since I got paid for the things I made, I rarely questioned the value of an hour of work, nor ever realized that I could have made more money working at Starbucks while working fewer hours. Yay, utilization!

Everyone around me was encouraging. I might even say impressed. See, graduating in the early 2000s was a lot like it is today: Lots of hungry and debt laden students competing for very few paid positions. It was very common to be a designer” while at the same time being a barista” or a guy who puts chicken wings in a bag for you.” I did that last thing, by the way. There were few viable alternatives if you wanted to make any professional progress while still doing important things like eating and having clothing. So to have started my own business was, to the onlooker who perhaps had not, pretty impressive. The fact that I had clients — more than one — who paid me — more on that in a moment — made me the Donald Trump of my cohort. I know, I know, terrible choice. But hey, I challenge you to picture any other rich person when you read the words rich person.” Sad.

Anyway, one day a friend stopped by my office while I was putting some invoices in envelopes. On my desk were also a few checks that had come in. Like, real, professional checks. The kind that don’t even have any handwriting on them. He saw them and practically fell off the edge of my bed, where he was sitting. You read that right. Bed. Because by office” I also mean bedroom.” Like I said, Trump. But the point is, he was impressed. There in front of him was the evidence that I had pulled this thing off. That I was making real money. That I was successful.

Over the course of that first year, several friends saw what I was doing and similar glimpses of what was for them a good enough indicator of success that they followed my example and started businesses of their own. This did not make me feel like a bishop of design entrepreneurship. It made me feel worried. It made me feel like a liar.

See, behind the perception that they had of what I was doing was the truth.

Their perception was that we were special. That we had brilliant ideas, talent to realize them, a tireless work ethic, and the drive to form all of that into something entirely our own. Their perception was that I had done that already and was well on my way to reaping the rewards. They looked at me and interpreted my life on the basis of three things that are guaranteed to skew the perspective of someone fresh out of college. First, worldview. They — we — had already been indoctrinated to revere the independent innovator. We learned at RISD that there was nothing we couldn’t make ourselves, nothing we couldn’t invent or improve. Outside of RISDs walls was a culture that worshipped the big idea and, naturally, the big ideator. Second, the value of reputation. I didn’t correct them when their observations were wrong or their praise unjustified. I wanted to be successful, and in our economy, reputation precedes riches. In the meantime, I’ll be honest: It made me feel good to be admired, even in small or silly ways. So I protected my own reputation at the expense of telling them how it really was. And finally, inexperience. My friends didn’t know enough to be able to look at my life and their perception of it and see where things didn’t add up. And I wouldn’t have, either, had I been them and they’d been me. It’s not like I was hiding some terrible secret, but Donald Trump probably never had a desk in his bedroom. And if he did, it was probably gold with marble columns for legs and some kind of water feature on it. Mine was plywood and milk crates.

The facts were not glamorous: Facing graduation and an intimidatingly sparse field of employment options, I started freelancing midway through my senior year. I realized this approach would be far less risky than moving out to LA and looking for entry level work there — something plenty of my classmates were doing. Ultimately, this was just an act of cowardice. Or, if I’m being kinder to myself, and act of playing-it-very-safe. So, I registered a business name and kept going. At best, I made OK work. Just OK. Most of my clients didn’t value design. And I certainly wasn’t helping them learn to value it more. I was 22, and I was cheap. Even so, it was a major effort to stay busy. I’d work 80 hours a week just to bill 25. I barely managed my finances. I probably earned just enough to transcend the poverty line. Everything I owned could fit in a couple of suitcases. I’d bike to client meetings. After my bike seat was stolen, I still biked to client meetings.

Not exactly an impressive sight.

After a year or so of this with not a whole lot of change, I realized that I was probably already looking at the ceiling if I didn’t find some way to learn what I clearly didn’t know. You know, like, the basics of design business. Project management, client services, financial measurement, marketing, sales, that sort of thing. I was really just winging it. I knew it, and it probably showed.

This epiphany came at an opportune time. I’d been doing some work for a guy who owned a small company just a short bike ride from where I lived in Providence. We’d been meeting up for coffee here and there and talking about design and business, which I saw as the beginning of a mentorship. I thought he was going to be my learning opportunity. As it turned out, he was recruiting me. I resisted this at first, thinking that it would be a compromise to walk away from my thing,” from my autonomy. But somehow I managed to look at it clearly and realize that taking this new job” was a necessary step in humility and toward learning all those things I knew I didn’t know.

That small company was Newfangled, where I still work today. It’s where I’ve learned everything I know about business and design. It’s where I’ve truly been able to be an entrepreneur, despite it not necessarily fitting the standard model for that. I didn’t found Newfangled. It had been around for 9 years before I joined the team. But, it’s where I’ve learned an alternative to the model of entrepreneur that we’re sold on a daily basis.

You know, the Founder with a capital F. The driven-from-birth, true-believer type. The one with the inexorable path toward success. That person’s story is a fairy tale. And yet, it’s a story we tell over and over again, despite it being a generally untrue description of reality for most people who have ever lived and ever will live. It certainly isn’t my story, and probably isn’t yours.

Let me tell you why.

This person is creative. This person is original. So far, so good. Who doesn’t want to be like that?

This person is driven to transform their ideas into tangible reality. He wants to change the world! He creates prototypes and refines them, perfecting a product. He creates complex systems to efficiently produce and deliver that product at mass scale. Jeez, we’re getting way more complicated now! Not everyone can do all that. Not hardly.

This person knows how to make his product desirable. He tells a compelling story and tirelessly promotes what he’s created. He tells you why it’s important. Why you want it. Somehow, he inspires and wins the adoration of his customers while ruthlessly devouring the competition. He creates new categories, repeating the process while building his empire. We’re getting close to myth here, people.

This person lives their work. Every moment is devoted to achievement. His achievement. He sets extremely ambitious goals, methodically reverse-engineers them, and takes only the most efficient steps forward. He reaps fortune and glory. He does this again and again. He does not lose.

(And yes, this person is often — too often — a man. A white man. A straight, white man. What gives? As it turns out, there are many not-straight, not-white, not-male people out there changing the world, and the more we celebrate that, the more there’ll be.)

Chances are (race, gender, and sexuality aside) you are not this sort of person anyway.

First and foremost, few people possess all of those strengths in equal measure. I know many brilliant people who — while they can certainly wrap their minds around the detail managed by various roles in a company — are happiest, most productive, and offer the most value to the big picture in cooperation with others. Or, in other words, focusing on the things they do best while relying upon others to do what they do best. It’s no coincidence that many of our treasured entrepreneurship stories begin with two people, rather than just one. It was Jobs and Wozniak; Gates and Allen; Brin and Page. I could go on and on. So why is it that despite the facts of history, we think that the successful CEO goes it alone?

Thankfully, many startup CEOs are coming clean about their struggles meeting their own expectations for what success might look like — there have been many op-eds along these lines over the past year. It’s not just that this sort of thing is hard — of course it is — it’s that the cultural narrative we’ve settled on is uninhabitable to most real people! Even the capable, sincere, and highly functional people from whom you’d expect great success to come easy. This may mean that whatever few cases do fit the narrative of the go-it-aloner — and they are very, very few — are not only the result of a variety of disparate factors glued together by luck, but also a very unique, rare, and quite possibly unappealing personality. You may want what these people have, but would you want to be them? There is an important difference there.

So it’s rare that there’s a sole hero at the center of these stories. But what about the plot structure itself?

Well, the linear component to the typical narrative is also misleading. And, it tends to be the thing we hear most about — the so and so never looked back and powered through story — and so we wrongly conclude that it’s a normative path to success. But it’s not. Realistic success narratives are much harder to string together because they’re ad hoc. They’re a long, curvy, choose-you-own-adventure style story of I did this, which led to this, which led to this, etc. But a simpler story, one in which I was certain that wanted this and so I relentlessly powered through to get it goddammit, is much more exciting and likely to cut through the noise.

But aren’t the ad hoc stories, in the end, more interesting? Isn’t there more mystery there? And isn’t at least mentioning the role of that mystery in our success narratives a more honest representation of reality?

After all, the mysterious twists and turns of reality don’t preclude your success or your failure. They’re simply the terrain. How you navigate them is the story you will tell. And the inherent diversity of the mysteries that will shape your life is a gift to us all, because they make plenty of room for nuance when it comes to defining how to achieve success, or even what success is!

You don’t have to try to reverse-engineer the paths of the Steve Jobses out there. In fact, it’s better that you don’t, because it probably won’t work. Steve Jobs worked hard, yes. Steve Jobs was brilliant, yes. But Steve Jobs also won a very particular kind of lottery. It’s not that there aren’t valuable things you can learn by studying a life like his, but you have the luxury of looking at his life in hindsight, going from effect and back to cause. He didn’t, and — when it comes to your own life — you won’t either.

Rather than trying to build a program for your life based upon the events of others’ lives, why not build a program for your life right now, based upon values you can embrace and trust will bring about good things in your life, and the postures you can take that put those values into practice.

What might that look like? That’s up to you.

You can stop reading there if you like. But I’d also like to share a few tidbits of random advice that might help you realize your vision, whatever it might be. These are not going to be about how to be creative or have good ideas. I think you’ve probably got that under control.

(1) Let go of entrepreneurship.”
Focus simply on having an impact. There’s really nothing else to add to that.

(2) Learn to perceive opportunity.
Everyone loves the life-as-story metaphor, myself included. But be careful to not go off the deep end and subscribe to a truly nutty belief like that you are the writer of your own story. A writer imagines a narrative with a start and end point and then systematically builds a plot that connects the two. We don’t do that. We stumble along the path blindly, learning as we go. You can’t write a story and experience it for the first time simultaneously. So which is more true of your life? Are you the writer, really, or the protagonist? It makes a difference.

When I was offered the job at Newfangled, I could have said to myself, no, mine is an entrepreneur story. the next chapter can’t be working for someone else.” But my goals, thank goodness, weren’t that specific at the time. They were to learn, to survive. I had the desire to be successful, which essentially just meant somehow gaining more influence and money than I had at the time. But I had no specific commitments to how that might be achieved.

In other words, it was about perceiving the next opportunity, not necessarily the final one.

This doesn’t mean that having an end-game in mind is wrong. It just means that you should realistically have a few end-games in mind, but a much more defined next step in place. You need to learn to run scenarios so that you can avoid the bad ones and encounter the good ones without brute force. Think of these as scenarios I can live with vs. those I cannot.

Have a loose agenda for life. It’ll make it much easier to have an impact!

(3) Experimentation results in being wrong, which is why you do it.
The thing that most disappoints me about our industry is that nobody really accepts experimentation. It’s ok if it’s part of a coolness doctrine — a-la Google’s 20% thing, which, by they way, they’ve tossed out — but when it comes down to real, deliverable working relationships, experimentation is practically anathema. For a design-school graduate, this is terribly annoying.

There is a professional spectrum along which expertise and experimentation lie. The variable that moves along this spectrum is the problem you’re trying to solve. As the problem grows in severity, the necessity of experimentation increases. Simple! Law knows this. Science knows this. Medicine knows this. In those areas, if you have a minor problem, like a small claim or the common cold, you’re going to get a rather boxed solution. But if you bring a truly severe problem to their office, the first thing out of a doctor or lawyer’s mouth will be, We can try this…” But marketers? They haven’t gotten the memo. And if you’re a designer, you’re probably working with marketers.

So your job is to work experimentation back into the professional vocabulary. Experimentation and confidence are not mutually exclusive, so we’ve got to be honest when we’re trying something. If you say try” with even the slightest apprehension, don’t expect to be given the chance. But believe in try,” and you will.

(4) Be platform agnostic.
I’ve designed for print, interactive media, and the web. I’ve designed systems and processes. I’ve consulted on all those things. Meanwhile, I’m keeping an eye on all kinds of other things that don’t yet impact my work but probably will. We all sit at the nexus of a variety of cultural, technological, and economic trend lines that will ruthlessly leave us behind if we make the wrong platform commitment. Instead, we need to think of design simply as a discipline of synthesis. Be flexible on the tools and context.

(5) Resist the container!
…and even the appearance of the container!

It was 18 years before Newfangled had a physical space that looked even remotely as beautiful or comfortable or stable as it should have. Not because we didn’t want nicer office space — nicer desks, nicer chairs, row after row of perfect, shiny mac workstations — of course we did. We’re only human! But there was always something else that we judged to be more important. To be more necessary. To be a better use of our time and resources. We never felt like we needed the perfect space to produce the right work. It’s always been about the work. Ask my colleagues. They’ll tell you about my Amish Dad tendencies and the crummy folding chair I sat in for years.

This isn’t meant to be a humblebrag. The point is, don’t be seduced by those beautiful pictures on Instagram of that latest startup’s digs. The truth is, they probably won’t last. It’s the quiet ones that have their priorities straight. They’re off working, probably in some room that doesn’t look like much.

In other words, don’t mistake rewards for goals.

(6) Learn to cooperate.
Entrepreneur used to mean someone who took on the full risk for an idea, including its funding. Today, entrepreneurs rarely do this. There is always someone else behind the scenes, and their name is probably on the checkbook. The unilateral, king of the mountain CEO ideal doesn’t really exist.

In the last few years, I’ve had numerous conversations with people who have startup ambitions — big ideas — and seem to think there’s some magic to making that happen. Like some secret recipe that makes it possible for them to do it all alone. I’ll usually probe around a bit to figure out what this person’s strengths are, and then my first bit of advice is almost always to find a partner. That’s disappointing to most people, which I find strange and maybe even a bit troubling. What is it about collaborating with someone who brings strengths to areas where you are weak that is unappealing? Is it admitting that you have weaknesses? If that’s it, then you’ve got a big problem that will weigh you down for as long as you ignore it. But more on ego in a moment.

Where I work, collaboration is essential. Mark O’Brien and I collaborate. He’s the CEO, I’m the COO. I don’t do what he does best as well as he does; he doesn’t do what I do best as well as I do. In the middle is plenty that we have in common — plenty of strengths, opinions, and perspectives — but it’s the differences that make our collaboration powerful. We’d be fools to think otherwise. This is true across our entire team.

(7) Get comfortable with uncertainty.
You can’t control uncertainty. That’s why it’s called uncertainty! But you can control how you feel about it. Comfort can be a byproduct of success, but it’s not a great goal by itself. In fact, don’t underestimate the value of discomfort, adversity, uncertainty. They’re powerful motivators. If you felt comfortable all the time and certain of everything, there’d be nothing for you to do, would there?

(8) Know yourself.
There is an independent agency run by a man I greatly admire. He’s one of those rare few that built it — slowly — from the ground up. But he learned that though he was able to build it on his own, he wasn’t going to keep it if he didn’t share the responsibility. He’s a wise man. In fact, he once wrote something that has really stuck with me. He was talking about how he has learned to empower the leadership at his firm — how to let them do their jobs to the best of their ability. He said he does this by making sure he has taken care of his ego at home. If he doesn’t have to satisfy his ego by micromanaging things, he can get out of the way and let the people he hired do the things he hired them to do.

We’ve all got an ego problem. It’s that we have one! The solution is not in denying your ego, it’s in taking care of it. If you don’t know yourself well, you’ll never figure out how to do that. Maybe that means making art at home. Maybe that means exercising. Maybe that means loving your kids. I don’t know. That’s up to you. But don’t expect to sustain success without figuring it out.

But there are two sides to the ego problem. Taking care of it in this way is about external damage control. But you’ve also got work to do to keep it from tearing you up inside. I think this should be pretty familiar territory for creative people especially. We’re an anxious bunch. We’ve got terribly high expectations. Those things set us up for disappointment and grief. So my last point:

Anxiety distorts time. Many of us are either living in the past or the future. That tends to produce behavior that is the result of regret prevention protocols,” not being truly present — with what is true right now and those around us that make that true. So ask yourself, what sort of life do you want to lead? Not have lead, but lead. As in now. Remember, we’re stumbling along the path blindly. Taking satisfaction in the path, not where we imagine the path leads, is far more likely to produce the sort of success that you desire, that you’re hoping to look back upon someday.

Success is not about a label, or even about being a certain kind of person. It’s about being you. Truly you.

So, with that — with whatever you’re doing, or whatever you aspire to do — I wish you all great success.

Heavy Rotation: Brian Eno’s new album.

Recent Tabs: Do you have eleven seconds to watch a person do an amazing thing with her body? Entire films in one, long exposure. Love how solid Rear Windows is. Shows just how much of that film’s frame is filled with a seated Jimmy Stewart. The Southern Sand octopus wins every game of hide-and-seek under the sea. a quarter of all the data out there isn’t even about humans…” As it turns out, Donald Trump is a shape shifting lizard” is an important safety message you need to read right now. The leader as explorer. Perhaps we should reevaluate magnetism’s importance.” The secrets of soothing spaceship sounds.


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