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Navigating Uncertainty for Entrepreneurs & Creatives

I hold space for vast amounts of uncertainty in my life – creatively, entrepreneurially, existentially. My closest teammates, friends, and family know this.

But not everyone is temperamentally disposed to invite uncertainty. I respect that. So, I also train clients to navigate uncertainty in ways that work for them when branding, rebranding, and advancing next endeavors with far-future horizons.
I use a framework called Fertile Confusion. It’s a process I use to convert confusion into innovation and break-throughs.

The Birth of a Framework
Ten years ago I was walking and talking with a former CEO through the Hudson Valley woods. He had gotten “booted” from his own company in the city and wasn’t sure where he was going next. Dialogue as I loosely recall it:

Him: “I’ve known for years what I’m supposed to do, how I’m supposed to show up. That’s all in the air now. I can see a few fleeting ideas for what’s ahead but otherwise, it’s all murky.”

Me: “It sounds as if who you thought you were is dissolving, and you can’t really see whom you could become. You’re caught between selves. Something like that?”

Him: “Oh my god, yes.”

Me: “How can we keep this stage fertile? You know, creative?”

Him: “What do you mean?”

Me: “I mean, how do we assure you don’t run back to something like that old self, that same occupation that you may or may not want? How do we fertilize the confusion?”

Hence, the birth of a concept and framework that I’ve been tracking for a decade.

Fertile Confusion is a state in which you refrain from seeking easy solutions or revert to old patterns long enough to advance or abandon a new, complex endeavor. Confusion arises typically between the desire to keep things safe and the soulful push to shake things up out of integrity.

Fertile? Two conflicting forces, ideas, or concepts come together to seed this pregnant phase of possibility.

Common situations when confusion can be fertilized:

  • The multi-book author wants to Break Brand and become known for something else – but she fears that’s foolish and doesn’t know what that “something else” might be.
  • The CEO of a dozen years wants to pursue what his own ideas and identity are outside of the company – but he fears looking foolish and doesn’t know what his own viable ideas might be.
  • The wellness coach wants to put her ideas on the line by at last coming forward and public with her signature brand – but she fears being attacked and does know what her brand might be.

Fertile Confusion arises when we’re in profound transition by necessity, circumstance, or calling, or all of the above. It arises among executives in transition. Among people rebranding as an opportunity for deeper dive growth. Among creatives venturing into terra incognito.

How do You Fertilize Confusion?
When you’re in a stage of fertile confusion, how do you keep it fertile and creative? What elements or practices or partnerships help you?

If you’re experiencing Fertile Confusion, know you’re not alone. I pack-sourced that question on my Facebook Wall, by the way. Here are just some of responses from our TW Community

The common metaphors among entrepreneurs and creatives I’ve interviewed and worked with on this stage often relate to incubation and emergence. Incubation: going within, stillness, solitude, centring. Emergence: coming out, announcing, renewed confidence, vision, mission.

I want to tweak something here, though. I want to suggest especially this: Prolonged incubation should not be endured in prolonged isolation.

Here are 3 suggestions.

#1 Reframe From Crisis to Quest
“As a writer,” fiction writer Charles Baxter once told me, “I don’t think I have just one mid-life crisis. You’re perpetually uncertain and in change.” Indeed!

Consider Fertile Confusion less as a crisis and more as a quest for a new solution, a new design, or a new identity. Whether we’re talking about your life or a creative project in the context of your life, a quest is marked by adventure, creative risk, resourcefulness, and meaningful change.

This is the mindset that unites the Questers from 16 countries in our free Quest Community of business artists.

Which leads me to the next points.

#2 Experiment
Business artists create like artists, experiment like scientists, and earn like entrepreneurs.

Convert your uncertainty into an experiment. Are you unsure if your new product idea will sell? Create a prototype and test. Are you unsure if you want to stick with a topic of influence? Create a testable talk and start testing the talk in front of low-stakes audiences. Are you unsure how next you’re going to deliver value in a venture of your own? Find a collaborator or two willing to take a low-stakes risk with you and test out delivering.

Operate hypothetically: If I do X, Y will happen. Test. Gather the data. Test again. Gather the data.

Remember being 8 years old, and testing how far you could jump? Yeah, that mindset with a little more edge and skin in the game.

#3 #DIT
Really, you have to find the right collaborators, confidantes, or mentors to help you do three things: Get perspective on your vision. Help you build the skill set or craft set necessary. Cheer you on or warn you that you’re about to fly off a cliff.

If you’re looking for a group of people you can share your creative ideas with, a community to lift you up, offer feedback and help you step into doing your best work, I invite you to join our Tracking Wonder Quest Community.

In our community, you’ll gain weekly inspiration, access to special meetups, and opportunities to find allies online and in your region of the planet. Our free community is comprised of professionals, entrepreneurs, creatives, teachers, coaches, and consultants (many of whom align with being introverted)  from 15 countries, dedicated to doing business from a place of authenticity and wonder. Join us.





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