Kickstarting Your Creativity for Career Change

“Every child is an artist, the trick is to stay one as you grow up.” –Pablo Picasso
It’s possible no one has ever told you that you are creative. It’s even possible you’ve been told the opposite: that you are not a creative person.
There’s a deeply ingrained belief in our society that creativity equates solely to being able to produce creative works of art. “Creative people” live in a different domain from the rest of us regular human beings; they’re the painters, the novelists, the virtuosos and zany artistic types. Those people are creative, the story goes, and everyone else is not.
This idea that creativity is the domain of only a chosen few is a myth we must bust early and often. The reality is that we are all creative. Sometimes we just need help tapping back into our creative current. The future of our Escape, no matter how big or small requires it.
Albert Einstein said: “We cannot solve our problems with the same thinking we used when we created them.” Similarly, we cannot Escape unfulfilling work and build a career on our own terms operating by the same code that led us here. We need a new approach.
What is Creativity?
It’s easy to think that creativity is all about painting, writing, dancing or singing. We prefer a broader definition. Creativity is more about being free to explore and create something without worrying about a fixed outcome. Put another way by Tom and David Kelley, cofounders of IDEO design firm: “Creativity is something you practice, not just a talent you’re born with.”
Creativity is an act and a choice. We can choose to approach almost every moment of our lives with a sense of creativity. The problem is if you don’t use part of your brain often, like an unused muscle, your creativity can feel flat and weak. Creativity can atrophy.
In its purest sense, creativity looks a lot like play. Think back to when you were a child in your moments of pure innocence and play. You had the freedom to create imaginary lands or sing made-up songs or dress in the whatever outfit you could get your hands on. You probably didn’t care much about labels like “I’m creative” or “I’m not the creative type”; you were just playing.
At some point along the way, someone may have shaken this foundation for you. Maybe someone laughed at something you created, or you felt judged or experienced some other embarrassing moment that taught you “I’m not good enough” when it came to acts of creation. This moment may have convinced you to hang up your paintbrush or your dance or some other form of expression. The words “I’m not creative” might have become etched in your mind.
For most of us, life eventually becomes less about imaginary worlds and more about the real one. The need for facts and figures overtakes the joy of playfulness, fun, and fantasy. In other words, we become grown-ups.
The Little Prince by Antoine de Saint-Exupéry is a classic piece of literature on the sorrows of growing up. This movie trailer gives a refreshed overview of the book and is sure to pull on your heartstrings.
The Kelley brothers of the famed IDEO design firm have echoed similar thoughts. From their HBR article Reclaim Your Creative Confidence:
“Most people are born creative. As children, we revel in imaginary play, ask outlandish questions, draw blobs and call them dinosaurs. But over time, because of socialization and formal education, a lot of us start to stifle those impulses. We learn to be warier of judgment, more cautious, more analytical. The world seems to divide into “creatives” and “noncreatives,” and too many people consciously or unconsciously resign themselves to the latter category.”
Ken Robinson’s “Do Schools Kill Creativity”, the most popular TED talk of all time, argues that the misplaced belief of “I am not creative” has roots in our education system, which removes space judgment-free creation time in favour of more analytical and fact-based subjects.
“My contention is that creativity now is as important in education as literacy, and we should treat it with the same status.” –Ken Robinson
Why is creativity important for career change?
So what if we’ve lost touch with our creativity––why does it matter for our career change? Even if you have no plans to move into a creative field, being able to imagine new and different possible selves to grow into, apply innovative approaches, scan for exciting opportunities and generate new options for yourself––all of these are creative acts. There are other forces at play as well that make creative necessary:
The human need to create is innate. The urge to create is a fundamental human trait. This trait has gone largely unappreciated at work today is largely a hangover of 20th-century industrialisation. In our community survey in 2015, “lack of creativity and innovation” in one’s job is one of the primary drivers of unfulfilling work.
Ideas are the new currency. The 21st century looks vastly different than any century we’ve seen. In a world where manual labor is being replaced by machines and knowledge, work can be outsourced, the ability to creatively solve problems is more important than ever before. The ability to come up with and implement innovative ideas might be your greatest asset, especially if you’re building a portfolio-like career or working freelance.
Creativity is a sought-after trait. Even if you have no plans to work for yourself, chances are your employer will be looking for someone who can access their own creativity. According to an IBM survey of CEOs, creativity is the most sought-after trait in leaders. Creativity is essential to success,regardless of role, discipline, industry––whether or not you’re in a “creative” field.
“Creativity is an essential skill for leaders trying to make a difference. Yet developing the ability to think and act creatively remains a thorny challenge. While there’s a hunger for skill development, elevating creative confidence doesn’t happen via traditional modes of executive education.” —Tim Brown, CEO IDEO
Creativity allows us to imagine new possibilities. We know that the same old problem solving won’t bring us new answers. When we’re thinking about career change, we need the ability to think of and engage with things differently in order to see with new perspectives and come up with new approaches and ideas. We need a period of creativity in order to think about possibilities instead of probabilities and to tap into the quiet dreams that live inside of ourselves.
What stops us from creating?
If creativity is simply something we do, rather than someone we are, then why don’t we do it more often? One reason may be the psychological hangover of being told “you’re not good enough” in some form or another. Another reason is that creating things is hard. It takes time, dedication and patience to tap into our creative current, especially if our creativity has atrophied over time.
In their work at Stanford’s, Tom & David Kelley have uncovered 4 fears that keep us from creating:
1. Fear of the messy unknown
2. Fear of being judged
3. Fear of the first step
4. Fear of losing control
Creation takes resilience. Doing the work is hard because it requires us to carve out time in our busy days to make something that can feel superficial and unnecessary. Especially when we feel like our creations are falling on deaf ears, the discipline of creation requires our grit and persistence.
The second part of the equation of creation makes it difficult as well: sharing what you’ve created. Sharing your creations, big or small, invites criticism, ridicule, and judgment. Making something and sharing it can feel a bit like standing naked on high street. You and your creations are exposed. Creation equally requires us to embrace vulnerability.
Tap Back Into Your Creativity & Act Like an Artist
Even if we’re not on an artistic path, there is still much to can take from the artistic world to help us tap back into our creativity. Here are five ways to approach your Escape as an artist would.
1. Get familiar with “The Resistance”
In his book The War of Art, Steven Pressfield puts a name to the frictional force that weighs on artists whenever they’re trying to create their art. He calls it “The Resistance.”
“Resistance is a repelling force. It’s negative. Its aim is to shove us away, distract us, prevent us from doing our work.”
Sometimes Resistance manifests as people (family, friends, foes), situations (disasters, deadlines, disease), or internal turmoil (self-doubt, perfectionism, lack of confidence). Resistance loves to encourage us to move away from things that matter deeply to us when the path gets difficult and demanding. If you look closely, Resistance is the same boulder that lives between you and your Escape.
Resistance sounds a lot like the force that drives us away from the things that matter to us. It’s similar to Rob Archer’s Experiential Avoidance. It’s the thing encouraging us to make “away move” in the face of discomfort and the unknown. Acknowledging that this force exists and calling it out by name is an empowering first step–moving forward in spite of Resistance is the next.
2. Don’t wait for inspiration.
When the author William Faulkner was asked whether he writes on inspiration or on a schedule, Faulkner replied: “Well, of course, I write on inspiration. Fortunately, it strikes every morning at a quarter past nine.”
It’s tempting to think that the greatest artists, entrepreneurs, and radical career-changers are always feeling confident and oozing with inspiration. The truth is that they don’t wait for inspiration to strike before they get to work on their art, their business or their transition. They do a little bit, every day, even when they’re not inspired.
Waiting for inspiration before you begin is a surefire way to never start. Showing up and working on your escape, even when you’re not feeling inspired (especially when you’re not feeling inspired) is the quickest route to becoming inspired.
3. Exercise your idea muscle.
Author and entrepreneur James Altucher has a simple daily practice. Every day he picks a topic and generates 10 new ideas around that topic. The quality of the ideas matters little. Most will probably be rubbish. He may not execute on the ideas or do anything tangible with them. That’s beside the point. His point is to make his brain sweat and work out what he calls his “idea muscle.”
Like any muscle, your “idea muscle” is one that can atrophy over time. It’s easy to think you’re not creative or that you don’t have any new ideas or you’ve run out of fresh ones. It could be that your idea muscle needs to be re-engaged and strengthened. This is something we’ll touch on in more depth in Week 5 around curiosities and ideas.
4. Do it daily.
Excellent artists were not great when they first started. They became great first by starting, and then by continually doing. They share a common sense of persistence and discipline. Like in Faulkner’s daily writing practice or Altucher’s 10 ideas a day, excellence comes from showing up everyday and working at it.
Similarly, great Escapes do not happen all at once. They happen over time through little daily actions. Like an artist chisels away at her craft, so too must we chisel away at our escape. Think little steps. Think repeated motions. Make a habit of doing the work necessary. It doesn’t even need to be a creative practice. U.S. Navy Admiral William H. McCraven suggests simply making your bed in the morning.
“If you make your bed every morning, you will have accomplished the first task of the day. It will give you a small sense of pride, and it will encourage you to do another task, and another, and another. And by the end of the day that one task completed will have turned into many tasks completed.”
Put another way by Aristotle: “We are what we repeatedly do. Excellence, then, is not an act, but a habit.”
5. Engage in play.
It’s rare that we allow ourselves to play. Yet that’s exactly how most artists approach their work. The best ideas, breakthroughs, and opportunities don’t come from strangling them with seriousness. They come about when we play. Letting ourselves go wild and have fun is a luxury we rarely allow. When all feels lost, grab a marker, grab a ball, grab a friend, and just play.
“Play is a state of mind – it’s a way to approach the world. Whether your world is a frightening prison or a loving playground is entirely up to you.” –Charile Hoehn, author of Play It Away.
A Helpful Reminder: You’ll Probably Be Bad Before You’re Good
One of the hardest parts of accessing your creativity or executing on any sort of creation, art or otherwise, is in the beginning. The part when frankly, you’re pretty shit. co-founder Alexis Ohanian perhaps says it best: “Sucking is the first step to being sorta good at something.”
Ira Glass of NPR’s This American Life says something similar:
And the Kelley brothers as well:
“Creativity is something you practice, not just a talent you’re born with. The process may feel a little uncomfortable at first, but…the discomfort quickly fades away and is replaced with new confidence and capabilities.”
As you begin to access your creativity, or even in the beginning stages of your Escape as a whole, you might feel terrible at it. That’s completely normal. Much like your Escape as a whole, you build creative confidence through small, bold and consistent steps.

Making a successful career change is hard and it takes time, but we’ve created our Career Change Accelerator to make it a lot less lonely and a lot more fun. Join us to accelerate your career change in an exciting new direction – find out more.

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