The E-Factor: The 10 Traits of Successful Creative Entrepreneurs

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Post-industrial capitalism is giving creative people a new way to both do what they love and put food on the table. The possibilities are practically endless, but there’s a reality about it that you must accept before you start: it is not going to be easy.

If you had a traditional brick-and-mortar business, you could write up a business plan, give market indicators, and go around and pitch it to banks and investors. These strategies have always had varying degrees of success, but they were understood as part of the process of “starting a business.” Internet businesses fall under the category of “high-risk ventures,” so don’t expect much help from banks and investors; luckily, you don’t really need them to get started. But they’re not the only ones that will withhold help from you.

The government is not particularly keen on Internet businesses, either. Uncle Sam wants you to start a brick-and-mortar business, hire a bunch of employees, and pay for their insurances and taxes. Your state wants your revenue to be taxed to fill its coffers. They want you to participate in industrial capitalism, and while they’re not going to set up a lot of roadblocks to keep you from doing your own thing, expect to play their rules without getting the big benefits they give industrial capitalists.

Most disturbingly, the people around you will likely be the biggest source of resistance. The type of entrepreneurialism we’re discussing falls outside what most people understand by a large margin. If you’re reading this, you’re part of a small percentage of people who understand that the Internet of today is not the Internet it was at the turn of the century. It may be hard for you to understand, but really, there’s a significant number of people in our society that still don’t get email. Never forget that you are already way ahead of the curve.

Given that people don’t understand the promise of the Information Age and that mass media does a good job of hyping every potentially bad thing that can happen on the Internet, many people will be a bit suspect of what you’re doing. Entrepreneurs always have to deal with people around them anticipating their failure, but Internet entrepreneurs have to deal with three stigmas: 1) if you’re making money online, you’re scamming or cheating people, 2) if you are making money, sooner or later you will fail or people will catch on and you’ll have to get a job, and 3) what you’re doing is not “real” work.

But there’s a deeper problem: your existence will make them uncomfortable. You are living a life that you’re defining day in and day out, and you’ll have that annoying habit of asking people what makes them come alive. They’ll see the through-and-through smile that exudes from you doing what you love and they will be uncomfortable because it will shatter their self-imposed worldview that we have to separate what we love from what we do to make money. They’ll resent your walking to the mailbox in your sweatpants as they walk into their houses in their work clothes.

You may think I’m painting a grim picture, but the truth of it is that these are fairly common experiences. You are, in fact, a renegade and a pioneer, and societies have ways of coping with you. It’s schizophrenic, but it’s the way it is.

Introducing the E-Factor

You’ll be sailing uncharted waters, and while many of us are out on the same sea, your course to port will be different. To make it to port, you’ll have to get good at piloting your own ship. This is where the E-Factor comes in.

I’ve been thinking for a while now about the best way to describe what makes creative entrepreneurs successful, and I’m now at the point where I’m willing to say that it’s not one characteristic or trait, but instead a cluster of traits and characteristics. Some people will be more driven than others, and some will be more ingenious than others, but you’ve got to have a mixture of both to some degree to make it.

The E-Factor is that combination of mindsets, behaviors, and characteristics that separates creative entrepreneurs from everybody else. You can talk to certain people and they’ll have everything they need to make something happen, but at the same time, you know they’ll never do it. Though it’s hard to put your finger on what it is, the E-Factor is almost palpable once you’ve worked with enough entrepreneurs. (And, for what it’s worth, it came out to ten traits accidentally – I wouldn’t do that to you.)

Here’s a stab at the components of the E-Factor:


Whether it’s desperation, extreme frustration, passion, or flat-out audacity, you’ve got to have something in you that’s driving you. And this fire has to be fueled by something inside of you – you can’t really get it from someone else. I like to call this the “burning why” – people that have the “burning why” only really need help figuring out how to do what they’re trying to do; once they get that plan, they’re off to the races.

Ability to Show Up (Perseverance)

While on first pass, you may think that being able to show up and being driven are the same thing, in reality, they’re different. You can be driven without being able to show up over the long term, and you can show up without being driven (most people show up to their jobs everyday, after all). And I want to focus here on the long-term; there will be days where you just don’t have it in you. But it’s the ability to show up over the course of weeks and months that makes the difference between people who quit on a great idea and those who make great ideas into a great success.


You must be able to defy the crowds. People will tell you that what you’re doing can’t be done. Your loved ones will be scared you’ll fail, and they’ll go paternalistic and tell you about the “Real World” and suggest that it’s wiser to get a job. They’ll have “great ideas” about what you should do although they have no idea of what you’re actually doing. You can’t ignore everybody, because good ideas come from unexpected sources, but you’ll have to learn to hear what people are saying, (perhaps) acknowledge it, and then defy them anyway. Accept that their resistance is almost always due to their own Stuff and not yours.


The days where you could oaf your way into success have long since past. The world moves too quickly, and change happens in weeks instead of years – sticking to what worked last year may work, and it may not. The more inventive and clever you are, the faster you’re able to solve a problem, the better you’re able to recognize good opportunities, the better you’ll be able to keep up with what’s going on or remain fluid enough to navigate your path.


Opportunities and ideas can come about quickly, and many of them are more time-sensitive than we realize. A good partnership opportunity may have a half-life of a few weeks after it’s recognized to be realized – after those few weeks, the relationship has lost its fizzle. Ideas lose their spark when left too long. Learning to act quickly enough to keep ideas and opportunities hot can make the difference between you building momentum and you starting your venture over every day.

Comfort with Discomfort

You probably started your entrepreneurial journey because you were uncomfortable with something before hand – you decided to do something different because you were uncomfortable. Unfortunately, that line of thinking is counter to what will make you successful as an entrepreneur. After a while, you’ll learn that that discomfort trigger is actually letting you know that what you’re doing is worth doing – it’s a sign that you’re onto an opportunity or idea that’s worth seeing through. Think of how many people reach a wall of discomfort and stop, and how many opportunities are on the other side of that wall.

Let me be clear here: you should never do things that violate your character or who you want to be, but learn the difference between those things that make you uncomfortable because they violate your character and those things that make you uncomfortable because they’re big or you’re not sure that you can do it or you’re not sure that it’ll pay off.

The other piece to this is that change can be uncomfortable. You will go through a period of radical change that you may not anticipate. You may learn more in the first year of your venture than you have in the last decade. You may open yourself up to new worldviews that cause resultant changes in who you are. To be uncomfortable with growing is to limit your ability to excel; you must choose between comfort or excellence.


To start the entrepreneurial journey is to accept some risk, but you have to see that “riskiness” is only one factor to determine whether you should do something. And you’ll have to get more fine-grained about what’s at risk, as there are good reasons to weigh things differently in different circumstances. For instance, a few hours of your time spent on an opportunity that may not bear fruit may make sense when your venture doesn’t have momentum but not make sense when it’s in a high-momentum peak. Instead of thinking about risks, think about opportunity costs; it’s helpful to make this shift because you realize that what you’re currently doing has its own opportunity costs that need to be weighed against other options. And get comfortable with failure.


This is a hard one, because people think that entrepreneurs are super-confident in themselves or their venture. The confidence here is about believing that what you’re doing is worth the shot and that you’ll be able to manage what comes, not that your venture is a certain success or that you can master anything. You have to be confident enough to know that you know enough or are competent enough, but not so confident that you think you know or can do everything – it’s in this fine balance that you can keep growing. And any time you think your venture is certain to be successful, stop for a second and reevaluate your assumptions; it’s when we’re certain of success that we’re most likely to fail.


If you don’t have any idea of where you’re trying to go, how do you know if you’re getting closer or further away from that destination? Without vision, it’s easy to get caught into the trap of not knowing what to do, so you do a lot of things half-ass or you do nothing out of confusion. Figure out which direction you’re headed (for now), and make small steps in that direction everyday.

So you could have made this step instead of that one? It’s better to make a few missteps that keep you moving in the right direction rather than being paralyzed while trying to figure out which step is the one you should take right now. You’ll never have complete information until it’s too late to act on it – but you can start with your vision and move in that direction now.


Start with what you have and work from it. Keep expectations and needs low, but keep effort and hope high (hat tip Naomi). Play every card you have to its fullest, and constantly work to add new cards to your deck. Learn the difference between an expense and an investment; curtail the former and maximize the latter.

Everything in Moderation

Just as with any other virtue, any of the components of the E-Factor can be taken to the extreme to the detriment of you and your venture. An extreme deficiency in the components will hamper your ability to grow and excel in your venture. The key is to develop each in moderation. To know what’s moderate for you, you have to know yourself and understand your situation – there’s no easy answer there.

Notice that I said “develop” the traits, and I really mean develop in the sense that these are not traits we’re born with. Again, like the other virtues, these traits are taught and learned. Some of us were lucky enough to have people that started honing these traits early; others of us had to learn them on our own late in the game. But the fact of the matter is that they’re not inherited traits that we’re born with, and now is as good of a time to start as any other.

Cognitive learning is a critical part of the developmental process, but it’s only a small part. Actually developing these traits is a matter of practice, which means if you want to be better at them, you’ll have to start practicing them.

No one is going to start this for you. I started this post the way I did to highlight that 1) there are a lot of disincentives for going this route and 2) you’re not likely to get much help in the initial phases. You won’t have to do it all alone, and if you tried to do so, you would probably fail. But the start begins and ends solely with you.

But how and where can you start? Stay tuned…I’ll publish the next part of this series on Friday.

Photo Credit: ilovepiano

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  1. says

    Right on Charlie! In a way I think you folded two posts into one with this one. First, unless you’re willing to invest a considerable level of effort, you may never overcome the obstacles that you will inevitably encounter. Second, the ten traits that you mention are key to success, and you may need to do some work to develop those skills if they don’t come naturally to you. All that sounds daunting, but really, it’s just like any other large goal – develop a clear objective, figure out the first few steps, and get started.

    I’d also like to point out one thing that I have definitely learned the hard way. It’s so easy to get hung up on chasing shortcuts that we don’t ever get to doing the fundamental core work to bring our vision to reality. There is definitely a time and place for optimization, but a lot of times it’s best to just dig in and plow through what needs to be done. I know, that’s another post, and you’ll probably get to that.

    It’s funny how memes pop up in different places in the blogosphere around the same time. Scott Young blogged about the effort threshold today.

    Mike Stankavichs last blog post..Blog suffers near-death experience

  2. says

    Yes Charlie, much wisdom here. I’d add comfort with ambiguity, since there are almost never answers or clarity about what is “right”. Best you can get to most days is the best guess I can come up with given what I know.

    Christine Martells last blog post..Continuing to process

  3. says

    I totally agree that successful creative entrepreneurs in this era are a new breed and many of the old ways of thinking that got people success in their businesses 20 years ago don’t necessarily apply anymore (like extensive long-term planning, methods of controlling, leaders who dictate). Those are a good list of 10 traits – many of them evergreen traits for success in any era.

    I think this new era is requiring some particular skills that haven’t been required for success in the past. Here are the 4 “Agile Living Strategies” for success in this era, as I see it:
    1.) Having the ability to keep a calm, clear and resourceful mind amidst chaos, change and uncertainty.
    2.) Understanding the psychological stages of the change process and being able to hold yourself and others steady as you lead yourself and others through change.
    3.) Being able to use your whole mind – straddling the left-brain-directed thinking styles (processes, logical & strategic thinking, technology) and the right-brain-directed thinking styles (creativity, story-telling, relationship skills, and collaborative skills).
    4.) Having the ability to question the “rules” of the status quo and the skills to elegantly break whatever rules you need to, to give you the liberty to custom-design your life- and workstyle, and be noticed as remarkable in the market.

    I’m looking forward to the next post in this series – really enjoying them!


    CathDs last blog post..Agile Living Strategies for Turbulent Times

  4. says

    Charlie, you really hit it. All the things you are saying have been things I’ve felt for years. This way of life is so rewarding, but can be very difficult too. It’s hard to get support when people think you sit at home eating bon bons all day.

    I also totally agree with your E-Factor assessment. When I started, I didn’t have some of those characteristics, but they develop after time. You really need to possess most of them in order to survive.

    I wish I had something more to add, but I think you really hit the nail on the head with this series. I can’t wait to read the next!

    Naomi Niless last blog post..Crowdsourcing and Spec Work – My Thoughts

  5. says

    Oh! Funny to see “the way I am” all listed out, and the subtext is brilliant (‘comfort or excellence’ to me reads: “you can be excellent without being perfect” since I’m comfortable putting things off until I can have them perfect.) Thanks for that.

    And for naming all the stuff that comes naturally, although you remind me that I need to improve at Lean-ness (an elaborate system when a start-up isn’t busy becomes a huge burden when business ramps up), and Moderation, but, um, I may put off tackling that one until I can get it right ~ tee-hee~ ! Thanks, and keep up the good works ~


  6. says

    Charlie- great post! I especially enjoyed your use of defiance to describe how successful entrepreneurs must push past the doubts of others (and sometimes self-doubt as well).

    Reginald – I think you include a great point…being teachable and one’s resourcefulness are critical components to success as a creative entrepreneur!

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