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Entrepreneurship doesnât mean what you think it means. Not necessarily, anyway. Itâs not about a particular method of creating something. Itâs not about startups. Itâs not about IPOs. And for the love of God, itâs not about disruption. Itâs not even about millions billions money, really. Itâs 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 â desire â must be true. Our culture has made an idol of âentrepreneurshipâ to such a damaging degree that far too many people make choices that lead to waste and despair, when â and I truly believe this â theyâd have been happier and more successful leading a very different kind of life. In fact, I think more people pursue âleadershipâ and âmanagementâ 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. Weâve made an excellent business of rushing ourselves to market and we accept far too much collateral damage.
My perspective on this isnât that unique. But itâs informed by my own path, along which Iâve come to rethink what it means to live and work many times, and will no doubt continue to. What Iâd like to share with you is how my own perspective on âentrepreneurshipâ 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, Iâm 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 didnât 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 âdesignerâ while at the same time being a âbaristaâ or a âguy who puts chicken wings in a bag for you.â 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 â more than one â who paid me â more on that in a moment â 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 ârich person.â 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 donât 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 âofficeâ I also mean âbedroom.â 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 â we â had already been indoctrinated to revere the independent innovator. We learned at RISD that there was nothing we couldnât make ourselves, nothing we couldnât invent or improve. Outside of RISDâs walls was a culture that worshipped the big idea and, naturally, the big ideator. Second, the value of reputation. I didnât 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, Iâll 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 didnât know enough to be able to look at my life and their perception of it and see where things didnât add up. And I wouldnât have, either, had I been them and theyâd been me. Itâs 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 â something plenty of my classmates were doing. Ultimately, this was just an act of cowardice. Or, if Iâm 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 didnât value design. And I certainly wasnât helping them learn to value it more. I was 22, and I was cheap. Even so, it was a major effort to stay busy. Iâd 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. Iâd 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 didnât find some way to learn what I clearly didnât 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. Iâd been doing some work for a guy who owned a small company just a short bike ride from where I lived in Providence. Weâd 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 âmy thing,â from my autonomy. But somehow I managed to look at it clearly and realize that taking this new âjobâ was a necessary step in humility and toward learning all those things I knew I didnât know.
That small company was Newfangled, where I still work today. Itâs where Iâve learned everything I know about business and design. Itâs where Iâve truly been able to be an entrepreneur, despite it not necessarily fitting the standard model for that. I didnât found Newfangled. It had been around for 9 years before I joined the team. But, itâs where Iâve learned an alternative to the model of entrepreneur that weâre 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 personâs story is a fairy tale. And yet, itâs 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 isnât my story, and probably isnât yours.
Let me tell you why.
This person is creative. This person is original. So far, so good. Who doesnât 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, weâre 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 heâs created. He tells you why itâs 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. Weâre 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 â too often â 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 thereâll 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 â while they can certainly wrap their minds around the detail managed by various roles in a company â 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. Itâs 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 â there have been many op-eds along these lines over the past year. Itâs not just that this sort of thing is hard â of course it is â itâs that the cultural narrative weâve settled on is uninhabitable to most real people! Even the capable, sincere, and highly functional people from whom youâd expect great success to come easy. This may mean that whatever few cases do fit the narrative of the go-it-aloner â and they are very, very few â 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 itâs rare that thereâs 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 â the so and so never looked back and powered through story â and so we wrongly conclude that itâs a normative path to success. But itâs not. Realistic success narratives are much harder to string together because theyâre ad hoc. Theyâre 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 arenât the ad hoc stories, in the end, more interesting? Isnât there more mystery there? And isnât 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 donât preclude your success or your failure. Theyâre 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 donât have to try to reverse-engineer the paths of the Steve Jobses out there. In fact, itâs better that you donât, because it probably wonât work. Steve Jobs worked hard, yes. Steve Jobs was brilliant, yes. But Steve Jobs also won a very particular kind of lottery. Itâs not that there arenât 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 didnât, and â when it comes to your own life â you wonât either.
Rather than trying to build a program for your life based upon the events of othersâ 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? Thatâs up to you.
You can stop reading there if you like. But Iâd 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 youâve probably got that under control.
(1) Let go of âentrepreneurship.â
Focus simply on having an impact. Thereâs 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 donât do that. We stumble along the path blindly, learning as we go. You canât 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, âno, mine is an entrepreneur story. the next chapter canât be working for someone else.â But my goals, thank goodness, werenât 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 doesnât 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. Itâll 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. Itâs ok if itâs part of a coolness doctrine â a-la Googleâs 20% thing, which, by they way, theyâve tossed out â 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 youâre 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, youâre 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 lawyerâs mouth will be, âWe can try thisâŠâ But marketers? They havenât gotten the memo. And if youâre a designer, youâre probably working with marketers.
So your job is to work experimentation back into the professional vocabulary. Experimentation and confidence are not mutually exclusive, so weâve got to be honest when weâre trying something. If you say âtryâ with even the slightest apprehension, donât expect to be given the chance. But believe in âtry,â and you will.
(4) Be platform agnostic.
Iâve designed for print, interactive media, and the web. Iâve designed systems and processes. Iâve consulted on all those things. Meanwhile, Iâm keeping an eye on all kinds of other things that donât 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!
âŠand 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 didnât want nicer office space â nicer desks, nicer chairs, row after row of perfect, shiny mac workstations â of course we did. Weâre 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. Itâs always been about the work. Ask my colleagues. Theyâll tell you about my Amish Dad tendencies and the crummy folding chair I sat in for years.
This isnât meant to be a humblebrag. The point is, donât be seduced by those beautiful pictures on Instagram of that latest startupâs digs. The truth is, they probably wonât last. Itâs the quiet ones that have their priorities straight. Theyâre off working, probably in some room that doesnât look like much.
In other words, donât 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 doesnât really exist.
In the last few years, Iâve had numerous conversations with people who have startup ambitions â big ideas â and seem to think thereâs some magic to making that happen. Like some secret recipe that makes it possible for them to do it all alone. Iâll usually probe around a bit to figure out what this personâs strengths are, and then my first bit of advice is almost always to find a partner. Thatâs 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 thatâs it, then youâve 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 OâBrien and I collaborate. Heâs the CEO, Iâm the COO. I donât do what he does best as well as he does; he doesnât do what I do best as well as I do. In the middle is plenty that we have in common â plenty of strengths, opinions, and perspectives â but itâs the differences that make our collaboration powerful. Weâd be fools to think otherwise. This is true across our entire team.
(7) Get comfortable with uncertainty.
You canât control uncertainty. Thatâs why itâs called uncertainty! But you can control how you feel about it. Comfort can be a byproduct of success, but itâs not a great goal by itself. In fact, donât underestimate the value of discomfort, adversity, uncertainty. Theyâre powerful motivators. If you felt comfortable all the time and certain of everything, thereâd be nothing for you to do, would there?
(8) Know yourself.
There is an independent agency run by a man I greatly admire. Heâs one of those rare few that built it â slowly â from the ground up. But he learned that though he was able to build it on his own, he wasnât going to keep it if he didnât share the responsibility. Heâs 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 â 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 doesnât 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.
Weâve all got an ego problem. Itâs that we have one! The solution is not in denying your ego, itâs in taking care of it. If you donât know yourself well, youâll 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 donât know. Thatâs up to you. But donât 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 youâve 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. Weâre an anxious bunch. Weâve 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 âregret prevention protocols,â not being truly present â 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, weâre 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 youâre hoping to look back upon someday.
Success is not about a label, or even about being a certain kind of person. Itâs about being you. Truly you.
So, with that â with whatever youâre doing, or whatever you aspire to do â I wish you all great success.
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Heavy Rotation: Brian Enoâs new album.
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