Upstartist Diaries

Where Experts Fall Short

When it comes to learning, I believe books offer the greatest return on investment. Hundreds of self-help and business books pack my Kindle. Where else can I get someone’s hard-earned lessons, distilled and painstakingly written, for $15?

It’s an astounding, almost comical bargain.

Yet, I discovered that even books have limits. In 2017, I was adrift, seeking direction. No number of bestsellers or esoteric masterpieces could help me breakthrough the fog.

I realized that I had to define and test my own rules for success – and update that book each week. I spent years experimenting with work, relationships and activities that made me end the day with a smile, a practice that I continue today.

The Cynefin Framework

One month ago, while in a leadership program, I found a framework that helped me see – with crystal clarity – where many success and business books fall short, and why I had hit the ceiling with experts.

It’s called the Cynefin Framework¹, and was created by David Snowden to help IBM in the late 90s. Cynefin (pronounced kuh-nev-in) is a Welsh word that means habitat or sense of place, and is meant to signify the multiple factors in our environment that influence us in ways we can never fully understand.


The big idea is to assess the context of the problem before acting. In other words, there is no one-size-fits-all process to problem-solving.

On the right side, or ordered space, cause and effect can be determined. On the left side, or disordered space, cause and effect is impossible to determine, or can only be determined in hindsight.

Each space requires a different problem solving process.

For simple problems, where cause and effect is predictable and repeatable, we should sense > categorize > respond. This is the domain of “Best Practices.” When it comes to content, imagine SOPs, frequently asked questions on support sites, or the “7-step guide to [insert something that has been done before]” listicle.

For complicated problems, where cause and effect is potentially knowable, and problems have several correct solutions, we should sense > analyze > respond.  This is the domain of “Good Practices” or of “Experts” who can help tease out cause and effect. Imagine bestselling business books, authority sites, podcast interviews and TED talks. 

For complex problems, where it’s difficult or impossible to determine cause and effect or a right answer, we should probe > sense > respond.  This is the domain of “Emergence” (my new favorite word). Imagine forums, groups and communities of practitioners experimenting at the edges of our known world (i.e. political movements, fundamental research, cryptocurrencies, genetics). 

For chaotic problems, where no relationship between cause and effect exists, we should act > sense > respond.  This is the domain of “Rapid Response,” where top-down, decisive and coordinated action thrives. Imagine responding to an unknown virus or act of war.

Finally, look at the disorder domain in the center. This is when we’re unsure or ignorant about the problem context. So, we default to assessing situations and taking action based on our personal preferences. Most of us live here.

For example, my default decision-making process is to seek expertise to solve problems. I did so my entire life until 2017.  The problem is that this method of problem-solving assumes knowable cause and effect. Starting a viable business and living a meaningful life don’t have correct solutions or predictable cause and effect. They exist in the domain of “Emergence.”

I didn’t have the vocabulary then, but much of my past 10-years has been learning how to survive in this complex space, where cause and effect are only evident in hindsight. It’s the uncertain, ambiguous world of gray, which is novel but mentally and emotionally exhausting.

The Cynefin Framework also explains why I’m obsessed about asking others about their perfect day, and why I feel uncomfortable giving anyone advice on hard life decisions (which are usually complex ones); I prefer questions that may lead them to their own truths or experiments. Everyone needs to write their own book.

In Chapter 2 of The Fail-Safe Solopreneur, I wrote about outsight – that in times of transition, you learn fastest from taking action. What else is outsight but the probing > sensing > responding required in the complex space? 

Our culture punishes failures and worships short cuts, so few of us prefer the complex space. When cause and effect and ideal solutions are not evident, the only way to learn is through iteration, which necessitates a lot of (often failed) experiments. Patience is also required, for only then can patterns – and a path forward – emerge.

The Cynefin Framework explains where so much of success advice falls short. Most readers crave the quick template, framework, and SOP to money, health, and success. Do this, do that, and boom, you’ll have A Four-Hour Workweek.

But, success advice can’t address complex problems, the ones we struggle with most in business and life.

Even worse, both egotistical experts and naive readers assume that solutions are one-size-fits-all answers. If business and success simply required a step-by-step plan or framework, everyone would be building million dollar companies and living their best life. Each person’s context, makeup and journey is unique.

So, if you feel like you’re at a dead-end with your learning, like I did with my hundreds of Kindle books, think about your problem-context. You may need to act in an entirely new way to break through.

What Content Will People Pay For in the Future?

I also believe the Cynefin Framework explains where solopreneurs in the content space need to move to build more valuable businesses. As a solopreneur who devours content – and is willing to pay for it – I’ve seen the money move from addressing simple > complicated > complex problems over the past 20 years. I’ll use Tim Ferriss as an example to illustrate this.

Simple Content (i.e. Best Practices) – 2000s

Instructions / Recipes / How To Blog Posts / Listicles / Books / FAQs / SOPs

Tim’s first book, The 4 Hour Week: Escape 9-5, Live Anywhere, and Join the New Rich (2007) and sections within, such as, “The Expert Builder: How to Become a Top Expert in 4 Weeks,” are titled like Lifehacker blog posts from 2005-10.²

Complicated Content (i.e. Experts) – 2010s

Guides / Books / Podcasts / Courses / Authority Sites / Consulting / Training

Tim started his podcast, The Tim Ferriss Show, in 2014, which strives to deconstruct the habits of world class performers. Podcasts, as a format, are perfect for more nuanced Q&A – where experts thrive. His podcast has gotten over 600 million downloads and one advertising spot now costs $43,200.

Tim’s last two books compile advice from experts appearing on his podcast: Tools of Titans (2016) and Tribe of Mentors (2017)

Complex Content (i.e. Emergent) – 2020s

Deep Conversations / Ecosystems / Groups of Practitioners / Reddit Subthreads / Daily Journals / Masterminds

Tim has built a constellation of elite practitioners in the emergent fields of biohacking, peak performance, psychedelics, and decentralized finance, to name a few.

His latest podcast episode is a 2 hour and 10 minute conversation with “Françoise Bourzat on Consciousness Medicine, the Art of Guiding Psychedelic Journeys, Finding Forgiveness, Salvia Divinorum, the Power of Chaos Music, and Inviting Sacredness (#519).”

This is about as far from “Become an Expert in 4 Weeks” as you can get.

In essence, Tim acts as a gateway to a constellation of thought leaders experimenting in the complex space. From the Wim Hoff method to ketogenic diets to longevity drugs, he brings his audience on a journey to explore the edges with world-renowned practitioners.

I feel like Tim’s journey mirrors many other content creator’s from Best Practices (listicles / best practices / e-books) to Experts (podcasts / webinars / training) to Emergence (building a content ecosystem of practitioners and facilitating connections that encourage experimentation).

From Expert to Emergent

Most “how to” information is free today, and accessible to nearly everyone. Getting expert, nuanced advice is also becoming more accessible through books, podcasts, online courses, free and ever-improving communication technologies like Zoom and of course, YouTube. I believe the next gold-mine for content creators will be creating spaces, channels and ecosystems that facilitate confronting and solving complex problems.

I believe the following 2 skills will be important to thrive as solopreneurs this decade:

Assessing Problem Contexts & Taking Action in Context-Appropriate Ways

Before taking familiar action, we must take a meta view of the problem. Can cause and effect be determined? What is the problem context? And what is our bias to solving problems?

Outside our business and personal lives, we can also hone this skill through role play. If you were running Company X, Organization Y, or Country Z, and facing the same problem, where would you locate the problem? What would you do?

Navigating the Complex Space (i.e. building up our tolerance for failure and prolonged uncertainty)

This a taxing, resource heavy space, a place of probing and experimentation. It’s time consuming, messy and often discouraging. But this is where the big problems and opportunities lie. We need to build up our endurance in this dynamic, impactful, and economically valuable space.³

As a solopreneur in the learning space, these are the questions I’m asking myself:

  1. How can I “hold the space” to help other solopreneurs manage complex business and life problems such as well-being? To me, this is about facilitating, connecting, and ecosystem building.
  2. What shared mission – beyond self-profit – would attract talented contributors to a rich learning ecosystem?
  3. What are the big problems in education with no right answers or cause and effect? How can I start connecting to others in these complex spaces? 

If our work can be reduced to “Best Practices,” we can be automated away. And if our content can be reduced to “Best Practices,” people expect it to be free.

It is one-step up to exist in the “Expert” domain. But there’s downward pressure on what “Experts” can charge i.e. anyone can now take courses from world-class universities and professors for free. If we only produce “Expert” content, the upside is often charging for our time as consultants, coaches, and speakers.

Working in the “Emergent” domain is riskier, but has asymmetric rewards. This is the realm of recent tech unicorns like Grab, Stripe, and Coinbase. In the content world, how can we build rich learning ecosystems, where our audience can connect, experiment, contribute, and come to their unique emergent solutions? And as solopreneurs, how can we get more adept at solving complex problems? 



¹ David Snowden and his team at Cognitive Edge have updated their diagram. They now say the complex space leads to “exaptive practices,” which means a feature having a function different than what it was intended for. For a 10 minute explainer, go to


² There are still benefits to self-help books. By making it seem easy, they get people to take action. Who doesn’t want a four-hour workweek? Tim Ferriss made it sound so easy that he inspired a global movement of location independent entrepreneurs, the most successful of which good-heartedly mock the book in hindsight. These entrepreneurs braved failure, anxiety, instability and loneliness to reach the mountaintop – and likely took years to get there. But they wouldn’t have started without a great writer and marketer like Tim selling the dream.

³ Vinod Khosla, founder of Sun Microsystems and a prominent venture capitalist, likens the complex space to the “fuzzy, unclear and uncertain” spaces at “the edges of the system.”

“In the edges where things are uncertain is where all the evolution is and where interesting changes in business or society happen. And unless you’re there, and learning fast from being there, and not being too arrogant to believe you know what’s going to happen, you’re not going to be in that learning edge of the wave where new things are happening… and that’s where failure happens often.”

– Vinod Khosla, Khosla Ventures


2 replies on “Where Experts Fall Short”

I love the depth of your insights here. I too was inspired by the 4 hour work week but since I’ve learned some of the realities of it the hard way I now gravitate more towards the concepts found in Deep Work! We looked the Cynevin framework 5 years ago as a way of analyzing Employee Engagement data. I just forwarded this to some of my team as it’s more relevant than ever to what we do.

I’m glad this struck a chord with you Dave! I’m still wrapping my head around Cynefin and its implications. Thanks for commenting here, and please, if you or your team think my ideas could use improvement or another perspective, please add here in the comments! Thanks for passing along…

I’ll also link to my summary of Cal Newport’s Deep Work:

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