Taking Creative Risks

How comfortable are you with taking creative risks? Not the small step variety, mind you.

But the ones that are scary. That begins with a variation of “I’ve never done this before.”

For 2022, I’m going to advocate that you not only get out of your comfort zone, but you skydive out of it. Whoosh! Experience the thrill of doing something completely new. And risky.

Short on ideas? No problemo. Here are nine ideas that you can use to start.

Creative Risk Number One – Collaborate

Collaborate with someone or another company. Why go it alone? What if you partnered up and worked to achieve something new?

A new product. Fundraise for a charity. A live or virtual event. Maybe a design collaboration with a local artist.

Can you imagine the outcome when you combine two streams of imagination and creativity? Sometimes the best ideas feed off of the input of another.

Who out there may be a perfect fit for you? Are you open to this opportunity?

Examples: John Lennon and Paul McCartney, Andy Warhol and Jean-Michel Basquiat, Steven Spielberg and John Williams, Taco Bell and Doritos, Apple and Nike.

Creative Risk Number Two – Play

Take time to play. How much time do you give your mind and soul each week to playing around? No direction or outcome. Complete freedom to fail spectacularly.

An easy way to start is to use the two-word sentence, “What if?”

What if you did something in reverse order?

What if you added an ingredient?

What if you made it smaller?

What if you only used blue?

What if it was virtual?

What if it was free?

What if…?

This creative risk is all about learning from failure. You have to be open to it. Instead of counting wins, count and keep track of how many times you have played around and failed.

Example: WD-40. You’ve heard of this product. I’ll bet you have a can in your garage, cabinet, or junk drawer. (But you lost that red nozzle straw thingy) WD stands for “water displacement.” The number 40 means this was the fortieth attempt at getting it right. Would you be willing to fail thirty-nine times straight and still think up the winning formula at attempt number forty?

Creative Risk Number Three – Teaching

Try teaching someone something. They say “those that can’t do, teach.” Which I find somewhat insulting and wrong. Let’s amend that phrase to “those that can’t do, don’t teach very well.”

If you really want to know something, try teaching it to someone that doesn’t know anything about it. You have to start at the fundamentals. Which is the stuff that you forgot about forever ago.

I’ve personally found that when I teach people something, and we start at the basics, quite often a new approach or idea opens up. This happens when I’m showing someone something or they ask a question.

It’s like a little gift that you get back when you teach. “Hey, thanks for helping show Nancy how to do this. Here’s a little brain nugget for you. Enjoy!”

Example: This blog. Where do you think a lot of these content ideas come from anyway? I was talking and teaching someone something and then…bingo.

Creative Risk Number Four – Templates

Use a template. Want ideas faster? Start in the middle.

Sometimes the fastest way to iterate is to begin with a set of pre-conceived parameters.

How many variations can you produce when you already know the basic facts about something? Use one idea to wireframe your innovation or creative idea and build around it.

You have probably read the famous quote by Picasso, “Good artists copy, great artists steal.” Can you take one idea and turn it into something new? History is littered with people who used inspiration to spark a new idea.

Examples: Joseph Conrad’s “Heart of Darkness” and Francis Ford Coppola’s “Apocalypse Now,”, Howard Schultz’s enjoying the coffee culture in Milan as the inspiration for Starbucks. Metallica playing with a live orchestra.

Creative Risk Number Five – Distance

Quite often you can’t think up new and innovative ideas because you are too close to the problem.

Creative risky solution: Ask people that don’t know anything for ideas to solve your problem.

Sure, you are the expert. No doubt about it. But, when you try to tackle a challenge and it just isn’t working out, try asking someone else for their idea on how to solve it.

Why does this work? Because they are bringing their life experiences, skill, and knowledge to bear on the problem. They don’t know what is “right” or “wrong,” but I’ll bet they have a solution that you haven’t considered. The greater the distance between known expertise and the problem the more novel the new idea might be proposed.

Example: Thomas Edison famously brought in teams of people with different backgrounds for his Menlo Park invention factory. Also, any idea cooked up in the shower, driving your car, or mowing your lawn.

Creative Risk Number Six – Doodle

I’ve heard it before. “Marshall, I can’t draw a stick figure to save my life!”

Here’s the thing…people don’t try to draw because of one reason. Fear of what other people will think. This is the same reason why some people aren’t as creative as others. Fear is the limiting governor behind being stuck.

But what if you found a way to dig yourself out of that fear-induced ditch?

Enter the doodle.

I like doodles because they can be anything. Shapes, lines, words, scribbles, dots. It is all good.

I doodle in the margins. At the top or the bottom of a page. On Post-It-Notes. When I’m on the phone. During a conference call. When I’m watching a video.

By the way, I’m definitely paying attention and listening. But that act of doodling begins a memory map and an idea starter deep in my brain.

The act of doodling frees up the subconscious mind and allows it to wrestle with ideas and play with them. Here’s where you can connect one thought to another and actually record the connection!

What is also great about doodles is that they are temporary. They are not precious. Nobody paid a gazillion dollars at auction for a doodle. They definitely don’t have to be perfect.

Example: Read this fun article from Inc. on how doodles are “thinking in disguise.”

Creative Risks Number Seven – Gamification

Let’s face it, as people we hate boring. Anything we can do to make something go from zero to hero, we will jump in with both feet.

So think about the most boring aspect of your business. What is a complete yawner?

Gamification has been proven to help engage both employees and customers, create a better business culture, and change negative behaviors.

After all, “we are what we repeatedly do.” How can we encourage others to do the right thing?

Make a game out of it.

So think about how you can add gamification to your work process, business, or motivation needs.

  • Can you create a series of challenges (aka “training”) where the employee or customer can level up when they complete them?
  • What can you build that will reward positive behaviors? Rewards don’t have to be flashy or big.
  • How can you map out benchmarks and goals to obtain?
  • What are you going to do to track and report progress?

Examples: Cheers for Peers, Employee Training Programs, Company rewards program,

Creative Risk Number Eight – Imperfection

Many people don’t achieve much because they wait until “everything is perfect” to do anything. They sweat the details. Make a million revisions. Go over and over and over and over whatever it is they are working on and still don’t push send.

I have news for you. It doesn’t have to be perfect.

Steve Jobs was right. “Real artists ship.”

This means that you have to birth the baby. Hit publish. Launch before you are ready. Don’t worry so much about polishing it up. Just do it.

Everything you do in life and business is connected to your experiences of “what came before.” But you have to cross that goal line to learn stuff.

I’ll take published imperfection over the perfect thing that nobody sees because “it’s not ready yet.”

So take the risk. Launch your art into the world before you and the art is ready. It will be ok.

Example: Pablo Picasso made about 50,000+ works of art in his lifetime. He is undoubtedly one of the most famous artists of all time. He went through many different artistic periods and experimented constantly. How many of his works can you name? You have to put in the work.

Creative Risk Number Nine – Make Time

I have to ask you one question to wrap up this article. How much time are you devoting to creative thinking?

If you are like most people in this business, I’d guess it is about a zero. We are usually too busy putting out fires and getting orders ready to ship.

Sitting down and quietly spending time on creative thinking? Are you mad? Who has time for that?

Well, you should. This is a creative industry. Your main competition has creative people on their team too. And, let’s not forget that usually, our customers aren’t all that creative. That’s why they hire us in the first place.

Do yourself a favor. Take thirty minutes a week. Close the door. Get comfortable. Grab a pen and some paper. Start writing. Get to doodling. Make a sketch. Create a list of problems and think about how to turn those into opportunities.

The risk here is that you spent thirty minutes on something that wasn’t connected to an order. (Yet)

That’s my challenge for you today. Pick a creative direction and start.

There is no waiting this year. Do it.


“If you are not willing to risk the unusual, then you will have to settle for the ordinary.” – Jim Rohn

“The risk of a wrong decision is preferable to the terror of indecision.” – Maimonides

“Risk comes from not knowing what you are doing.” – Warren Buffett


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