#1 Skill Entrepreneurs Need to Have

Instructions for how to get out of your own way

A large subset of the population are “solopreneurs”. Entrepreneurs who work alone. Tres chic, no? And, while working by ourselves, for ourselves has a long string of perks like unlimited bathroom breaks and flexible work hours all night long, it also comes with one elephant-sized drawback: in a bind, there is no one to help us but our own fool selves.

This goes for professional speakers too. To the outside eye, speaking may seem a glamorous, high-paying career choice, complete with international travel and multilingual applause, but when the speaker’s bureau or publishing house comes knocking for new content, the professional thought leader feels the same pulmonary quickening experienced by the rest of the solopreneur world.

What if I never think of another meaningful idea again?

This is usually followed by much drinking and rocking back and forth on the living room floor.

Now stop, stop, stop before you make yourself sick! We have a tool to combat this Writer’s Block — yes, we do! It is the mighty Brainstorm!

(Thunder crash!)

Yes, yes, I know you think you know what a brainstorm is, but have you ever really done it? Did you know psychologists have spent the last 50 years developing guidelines to help you do it better? And that all over the globe the best design thinkers and change-makers are using brainstorming to create new innovations?

Best part? We can do this by ourselves, solo!

So quickly, why do we need a “process” for brainstorming? Isn’t it just thinking really hard? While we know we want the best solutions to our problems, we also tend to want them right now. Haste almost always is a baseball bat to the knees of creativity. These guidelines are rules of engagement for ourselves so we don’t let our neediness get in the way of finding the best solutions.

I’ve adapted them from Creative Problem Solving: An Introduction by Donald J. Treffinger, ‎Scott G. Isaksen, ‎and K. Brian Stead-Dorval.


The 4 Guidelines for Effective Brainstorming

1. Withhold all judgement

When brainstorming, refrain from judging an idea negatively (“no, that’s not it”) or positively (“yes, that’s it!”). Our brains cannot generate ideas and evaluate those ideas at the same time, the two processes conflict. Any judgement, even a positive one, will slow the ideation process, shrinking our options to a mere handful of possible solutions to the problem. If you want positive support while brainstorming try, “You’re doing a great job at brainstorming. What other ideas do you have?”

2. Go for quantity

I explain to my clients that asking our brains for new ideas is like tapping a beer keg: the first five ideas are foam, they’re airy and unoriginal, but if you pour through all of that fluff you get to the golden nectar you’re thirsting for — the elusive New Idea. We can be so eager for that one, perfect answer to our problem, that we forget the need for newness. Original ideas come after first flushing out the ideas we’re already aware of, the ones our brains have deemed safe or appropriate. I frequently ask clients to generate 100 ideas when they’re brainstorming.

What’s the use of wasting your time with all those ideas? You’ve got to trust your brain on this one. If you’ve thought of the idea, there must be some value in it, although you may not see the value at first. You may not use idea #99 to solve this particular problem, but you may be able to learn from the idea or use it later on.

3. Go for wild and crazy

If you already knew how to solve your problem, well, it wouldn’t be a problem would it? To solve it, you’ll have to think in a way that is different than you have before. You’re going to have to challenge yourself and — Warning! — it’s going to feel wild and crazy. Not only am I giving you permission to go there, but I demand that you do. Don’t give me any safe ideas! Give me bold ideas! And why not? It’s fun to think wild, it doesn’t hurt anyone to think crazy, and it will train your mind to see greater possibilities.

4. Make connections

Our brains think linearly and brainstorming is no exception. You’ll find that one idea will lead to another and another and then, usually around idea #20, you’ll see your train of thought dry up. Now what? Connect that idea to a totally different idea and see what those thoughts create. Here’s an example: a client of mine is a mixed medium artist and disliked how off-brand (and boring) the exchange of business cards was for her. Brainstorming, she connected the idea of the business card exchange to her art and synthesized the idea to create a mini painting on the inside of an antique cigarette case to be used as her business card holder. Now, every time she pulls out a business card, she’s showing her art and impressing the pants off her buyers with her creativity. Connecting at its finest! (Check out her work: Deborah Liljegren.)


The brainstorming process is a skill, make no mistake, and a darn fun one to develop. It can be difficult to keep the ideation process open. That’s okay, it’s like a muscle and it will get easier with practice. It’s what kids do when they play, what we all once did: withhold judgement, go for quantity, go for wild and crazy, and make connections.

Enjoy your brainstorming!


About the Author

Kelsey Crouch is a story sleuth and audience relationship coach. Sign up to receive Subtext the Creatives’ Newsletter, and connect with her on Twitter and LinkedIn.

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