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Getting Comfortable with Chaos
entrepreneur swimming in paperwork

I believe the number one thing holding entrepreneurs back today is their fear of chaos. Uncertainty. And all the unknowns and scheduling conflicts it brings.

Christopher Alexander explains the modern, unhealthy fear of chaos in his book, “The Timeless Way of Building,”

“. . .we have so far beset ourselves with rules, and concepts, and ideas . . . that we have become afraid of what will happen naturally, and convinced that we must work within a ‘system’ and with ‘methods’ since without them our surroundings will come tumbling down into chaos…”

And that,

“. . .Without method and more method, we are afraid the chaos which is in us will reveal itself. And yet these methods only make things worse.”

How many apps promise to improve collaboration, but only serve as a distraction? How many plugins or systems promise to improve our workflow, but result in lifeless products? With this in mind, it’s no wonder why innovation is stagnating; we’ve all but completely removed chaos from the creative process.

Via Forbes,

“. . .You can’t create a successful company, especially in this wide-open digital economy, without being comfortable with the unknown and the unknowable. Success is ultimately derived from chaos, in the absence of having all the answers. As Reid Hoffman, co-founder of LinkedIn, aptly puts it, ‘People that run these perfectly non-chaotic organizations somehow never build great companies.’”

As entrepreneurs, our world is fraught with chaos; in order to survive and thrive in it, we need to embrace entropy — not run from it.


5 Ways to Thrive in Chaos as an Entrepreneur


1. Let your ideas bleed into one another

In an interview with Billboard in 2015, renowned American entertainment entrepreneur Donald Glover stated, “I don’t separate things, all my ideas bleed into each other.”

He went on to explain,

“In my house, I have an empty room: I have my studio there, a whiteboard with the Atlanta scripts, a canvas for painting and all my albums and DJ equipment. I wake up every morning and I start grabbing things — spray-painting the walls, recording, writing.”

While you don’t need to have a spare room in your house to graffiti like Glover, entrepreneurs should be open to radical experimentation. Look beyond conventional use cases and verticals for your product/service — you could be leaving numerous opportunities on the table.

2. View “bad” ideas as progress

Whether it’s an unsuccessful app, a visual that misses the mark, or copy that isn’t persuasive, every entrepreneur comes up with “bad” ideas. It’s part of the job. Thinking that you should always have the Midas touch when it comes to your work isn’t only unrealistic – it’s unhealthy.

Instead of viewing your bad ideas as failures, view them as progress: by eliminating concepts that aren’t working, you are able to get that much closer to the right solution. Not only does this help you become less discouraged when your ideas don’t pan out, but it ensures you have a healthier outlook on the creative process.

My wife, an elementary school teacher, always reminds me that practice doesn’t make perfect – practice makes progress. Life lessons for children work well for me.

3. Strip down to the basics

All too often, entrepreneurs try to add in additional features to their product/service (aka feature creep) in an effort to make it more appealing. Unfortunately, this can make a product/service more alienating and confusing for customers than it was in the first place (read the story about the genesis of Instagram for a great example of this). Remember Alexander’s quote at the beginning of this article: more methods, rules, and concepts typically only makes things worse.

Instead of trying to make your product/service do everything for everyone, try reducing it to its core; you may discover that potential customers find it much more desirable.

4. Avoid perfection

The quest for perfection is one of the most perilous ego traps for entrepreneurs. It’s an ideal – something so unattainable that people mistakenly believe it must be worth pursuing. In reality, nothing is perfect, and products/services that aspire to be so often come off lifeless and boring.

5. Walk away, often

When you hit a development roadblock or challenging situation, take some time to walk away from your work. During this time, do completely other things (i.e. go on a hike, watch a movie, see friends) to refresh your mind.

When you return, you’re almost guaranteed to have new ideas. Chaos is like quicksand; the more you try to struggle against it, the deeper you’ll sink.


Entrepreneurs must learn to embrace chaos

It’s a natural feeling to want to avoid chaos — we crave certainty. It’s painful not knowing what’s around the corner. But avoiding it doesn’t help anybody, least of all ourselves. We’re at our best as entrepreneurs not when we reject chaos, but when we have the courage to confront and overcome it.


Stay hungry,