Chapter 4. Yes! And...
Theory & Practice for Independent Consultants

Why write a book about independent consulting?

Every independent consultant and freelancer takes a unique path. There's no blueprint to follow. But some of the challenges are shared: how to find clients? how to create your own identity? how to make a sustainable life out of being independent?

I've been an independent consultant for almost 8 years (more about me) and I'm writing this book in public, free online. It's filled with ideas and concepts that helped me, and might help you too.

The plan is to turn this into a real book by the end of 2022!

Catch me on twitter: @tomcritchlow

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1. Becoming Independent
6. The Inner Life of Consultants
The Strategic Independent: Theory & Practice for Independent Consultants

The Contrary Consultant

Embracing the fool & the power of not fitting in

August 18, 2020

This is the final piece of the 5-part Yes! And… series exploring the relationship between the theatre of work and the consultant as improv actor. Catch up on chapter 1 here.

Many independent workers are outsiders. However, as an indie consultant there’s often a pressure and anxiety to fit in - to step back inside “the system” working within the established processes and rules of the client organization.

This pressure to conform causes anxiety for an indie consultant - fitting in directly conflicts with your outsider and solitary nature - and gets magnified when working with high status actors like senior executives, CEOs, investors, and founders.

How do you resolve the tension of this duality - of being an outsider on the inside? As an actor outside the system, working to change the client’s systems the key is remembering your purpose:

When helping clients do new things, your job is to fight the status quo. New things don’t emerge from fitting in.

Even further - in this post I’m going to try and unpack the ways in which you can feel empowered by not fitting in. In fact, the key is to embrace the ways in which pushing back against the status quo and leaning into your outsider status can be rewarding and fulfilling.

Remember: when helping clients do new things, their mental models and incentive structures actively work against the change needed. This puts you at odds with the status quo at their organization.

And yet, in Optimism as an Operating System I said:

“If you walk in the door with a problems-focused mindset ready to criticise the client you’ll get rejected by the organization like a bad virus.”

So which is it? How do we rail against the system without criticising the client? How do we create a positive environment and at the same time disrupt the status quo?

The archetype we’re looking for is the fool:

Part 1: The Fool

The fool represents someone outside the system - the archetype of the fool is the court jester, an advisor and confidant to the royal court.

In King Lear, the fool has the ear of the king and is the only one capable of telling the truth. In the tarot the Fool card is one of the major arcana and can be either un-numbered, or 0 (low) or 22 (high).

The fool is contrary, naive and uneducated - but at the same time wise and capable of surprise and delight. An outsider, but with the ear of the ruling class.

The idea of the jester as a change agent has been explored before - this paper Fooling Around: The Corporate Jester as an Effective Change Agent for Technological Innovation by Tom McMaster, David Wastell and Helle Zinner Henriksen1 has some great observations and draws parallels between key change agent traits and the traits of the jester:

So playing the fool can be effective if you’re seeking to drive change - but it’s not just about being effective, I believe the archetype of the fool runs deeper and independents can gain strength and power from playing the fool and not fitting in.

The Contrary Fool

The Yes! And… series (start from the beginning with part 1 here) is inspired by the book Impro and here I want to draw inspiration from Keith Johnstone. He has a whole section called “Notes on Myself” where he has a passage on contrariness:


At about the age of nine I decided never to believe any-thing because it was convenient. I began reversing every statement to see if the opposite was also true. This is so much a habit with me that I hardly notice I’m doing it any more. As soon as you put a ‘not’ into an assertion, a whole range of other possibilities opens out-especially in drama, where everything is supposition anyway.

When I began teaching, it was very natural for me to reverse everything my own teachers had done. I got my actors to make faces, insult each other, always to leap before they looked, to scream and shout and misbehave in all sorts of ingenious ways. It was like having a whole tradition of improvisation teaching behind me. In a normal education everything is designed to suppress spontaneity, but I wanted to develop it.

As a perpetual outsider this idea of continual questioning, spontaneity and provocation felt true.

I re-wrote this contrariness section in my own words focused on my own practice:

The Contrary Consultant

Every consulting engagement starts with reversing the client’s beliefs - challenging every foundational notion to see where there are strongly held beliefs, and where there are inconsistencies. A “not” opens up a problem and reveals all strategy is supposition anyway.

During a consulting project it’s natural for me to misbehave in all sorts of ingenious ways relative to the status quo - to craft alternatives to the existing structures. Normal business operations are designed to suppress spontaneity but I seek to develop it.

I have personally integrated these two archetypes - contrariness from Keith Johnstone and the fool from the tarot - into a personal approach to consulting that seeks surprise, questions over answers and can speak truth to power.

This idea of contrary consultant - playing the fool archetype - is helpful because it reminds me that… there is no choice. Indie consultants are often not just outsiders but perpetual outsiders. There’s a value in being contrary - but there’s no way out for perpetual outsiders. We’re often weirdos and oddballs who can’t help but question and poke the status quo… So creating a sense of purpose, identity and acting that “resolves” this tension is deeply important.

Let’s take a closer look at themes of the fool: surprise, questioning & speaking truth to power:


Even though the client has hired you to change their organization - convincing them to change can still be challenging. Organizations are explicitly designed to prevent too much change too fast (even if many employees will deny this and corporate marketing will try to convince you otherwise). Think about how much chaos would be generated if every employee with an idea could act on it…

So, in order to convince a client to do something new, you need to be able to surprise them. To bring a client to not just a desire for change but also novel insight that provokes them to take action - to shake them from their status quo.

I wrote about interrupting routines to create surprise in chapter 3 - blocking and unblocking clients:

This paralyzed reaction to the “make up a story” prompt is exactly the same as many employees and teams when faced with a question of “doing a new thing” (i.e. building a new capacity).

Further - employees and teams are heavily incentivized to maintain the status quo. Even if it’s made clear the importance of doing something new their muscle memory is built around maintaining and optimizing the status quo…

As weirdos, outsiders and fools we’re often well placed to generate surprise. It can come in the form of new insights about the industry & competitors, it can come from questioning routine assumptions and “the way things are done” or it can come from just doing things in your own way.

These surprises are all designed explicitly to generate new momentum and to unblock clients - to demonstrate that there is a way forward when before there seemed none, to create new initiatives from scratch - and they require a healthy disregard for fitting in.

Before you can surprise a client, however, you need to find some truth - truths about the situation, about their beliefs, about the project you’re working on. This requires you to take the process of asking questions seriously.


Remember how naive the fool is. Especially at the start of an engagement it’s key to try and assemble a mental model of the client’s organization from first principles - and the only way to that is through questioning. Questions are one of the most powerful tools you have as a consultant.

When you ask a question and the client answers how do you respond?

  • Beginner consultant: here’s an answer to your problem…
  • Experienced consultant: here’s some possible answers to your problem…
  • Advanced consultant: let me ask another question…
  • Guru consultant: ok, let me ask the same question another way…

Don’t take shortcuts or assumptions - start at the beginning.

Leaping to the “solution” phase of consulting too soon is a mistake. (In fact many consulting engagements literally never get to the “solution” phase - there’s just a continual cycle of exploration). And further - clients are often pretty bad at describing their own problems2.

Questions and inquisition are at the heart of good consulting - you can’t truly know the problem until you understand:

  • What the client thinks the problem is
  • What the actual problem might be
  • How the current system operates
  • Why the current system caused the problem
  • Why the current system can’t solve its own problem

This requires a beginner’s mind - and a healthy curiosity. I wrote about this contrary line of questioning in my piece on workshops:

Don’t look for smart questions, look for dumb questions. “Ok, this might be a stupid question but why don’t we just build this the way we built the last one?”.

My favorite dumb question: “Seems like you have a good handle on the problem and the solution - what do you need me for?”

Playing the naive fool is perfect for asking “dumb questions” that provoke reaction and surface truths - ideally some truths about the organization, the situation and your point of contact as a human - and allow you to get some insight into “what is really going on here?”

Once we’ve assembled some truths and we’ve started some surprising behaviors it’s time to speak truth to power.

Speaking Truth to Power

The unique viewpoint of the consultant - and the unique ability to act as an outsider (and a fool!) provide you as the consultant a special opportunity to say things that people inside the organization might have trouble with.

Remember - the fool in the tarot is part of the major arcana but neither high nor low. Often un-numbered. When working in highly political orgs I like to think of myself as the “un-numbered VP” - part of the major arcana but unlike the others.

This ability to speak truth to power is a fine line - playing the fool and being an outsider doesn’t automatically give you the right to run your mouth. Instead you still need to carefully size your moments and positions to attempt to shine a light on the truth. Truth is dangerous. But the truth here can unlock great forces of change within an organization.

There’s three ways organizations are blind to the truth: blind to the obvious, blind to the outside world and blinded by politics. Let’s unpack them one by one:

Blind to the Obvious

As a consultant trying to build new capacities you often end up “strolling across the organization” - meeting many different parts of the business and working with teams and individuals at all levels and departments. When you stroll across the organization you often pick up a pretty complete picture of the organization as it is today without the frame and bias of previous experience, previous activity and history. In short - you get a clear eyed view of what is going on, without any baggage.

This allows you to point out things that are “obvious” but that people internally might not want to talk about - or might have conditioned themselves to be blind to.

Example: Working with a media company to overhaul their strategy people were looking for big ideas - when the smallest idea was the most powerful. That the content was simply not good enough. People internally were so wrapped up in how the work was made, the process that made it, why it’s made etc that they ceased looking at the output in any objective manner and had abstracted it to reports in spreadsheets. My ability to point out that the output was simply not good and below competitors was helpful and surprising. No one argued that the content was high quality - but it was still a surprise for someone to point it out to them.

Blind to the outside world

In addition to strolling across the client’s organization, as a consultant you stroll across many different organizations as you work with multiple clients. As you stroll across organizations you’re able to bring a little bit of the outside in. Often, when I work with an organization, there’s a team who have been advocating for some change for a long time without success. They feel frustrated and demoralized because of their inability to change the system. Often (not always!) it can be the consultant’s place to dust off the argument and re-frame it with some additional external context that helps executives finally agree to the change3.

Example: I was working with the market leader in a category who was getting complacent with growth. A simple survey of satisfaction of their website vs their competitors showed how their market position was under threat. I presented this alongside some internal change agents who had a suite of changes they wanted to lead and helped them gain executive buy-in through a sprinkling of external reality.

Blinded by Politics

The consultant often holds a very unusual role inside an organization - simultaneously a senior figure and an outsider at the same time. The consultant has no place on the map. Because of this - especially in larger political organizations - it’s possible for the consultant to be able to say things without agenda.

Of course, let’s be real, no speech is apolitical and nothing the consultant does is without agenda. But in the eyes of the CEO/board - a consultant can sometimes be seen as less biased than a suite of VPs all jockeying and vying for a small number of SVP spots. The consultant has their own agenda but it’s often orthogonal to the org chart and job title politics that VPs play.

In this way - the consultant can have a small voice and a big impact on issues where the organization is otherwise politically deadlocked. 4

Example: working inside an organization attempting a large re-org each VP presented their own budgets and headcount plan to the c-suite. Obviously every team pitches for more than they need so the CEO turned to me as a more impartial judge of what teams actually need - not in a formal way but rather in a hallway conversation - I’m a source of “truth” in a highly political situation.

Use this speech wisely.


So far we’ve looked at productive, positive versions of the fool archetype - but negative versions abound. Now in part 2 let’s consider some of the potential flaws that come with being a perpetual outsider and weirdo…


Part 2: The Dangerous Fool

I’ve spent the last few years actively seeking out and building a peer group of other indie consultants so I’ve seen many different flavors of weird. There are as many different flavors of indie consultants as there are different flavors of rejections that drive us - because to be independent requires a rejection - either the system rejected you or you rejected the system.

Some start out weird and get rejected by the system - some get rejected by the system and, untethered from structure, become weird. Either way you develop your own sense of weirdness and eccentricity.

From all the indie consultants I’ve met however there is a consistent behavior that can be dangerous - that is holding too tightly to your weirdness and outsider nature.

Productively Weird vs Defensively Weird

Many outsiders are distrustful and skeptical of “the system” - almost by definition the system has not worked for them - so they’re skeptical. And further, outsiders are fearful of conforming because it’s seen as the first step on a path to fitting in.

So outsiders rebel against the system - they become contrary, surprising and question everything. This is healthy but can be taken too far, this energy can be channeled in unproductive ways and can come across as defensive instead of generative.

I think about it like this: when asked to do something that feels like fitting into the system (such as lead weekly standups), I often find myself having defensive reactions and inclinations to distance myself. My knee-jerk reaction rejection and emotions span fear (what if I become just like an employee?), disgust (that’s beneath me) and distrust (do they see me as not capable of surprise?).

It’s important to recognize when you are projecting these emotional responses on the client. Examples of this might include “this organization doesn’t have anyone to run standups?” or “these standups are a waste of time” or “I should be doing something more important”. These defenses are a response to the perceived threat of compromising your identity and position as an outsider, your fear of being “taken over” by the organization.

The game to play here is to view fitting in as a disruptive act. To enjoy fitting in - the fool masquerading as status quo. The joy of fitting in is understanding how the status quo works to successfully overthrow it.

I like to think about this as focusing on generative destruction not defensive destruction. Remember - you’re there to change the client’s organization, but you’re not there to burn it down. And every client organization is likely far more functional than you give it credit for - sure there will be broken, counterproductive and inefficient parts of the system but the system as a whole is more functional than you think.

So pick your battles carefully - maybe you don’t want to lead the weekly standup meeting, but that doesn’t necessarily mean you should rail against stand up meetings as a practice. Maybe you don’t want to create a weekly report but by doing so you can attend the weekly executive meeting.

Forming a complete and integrated self identity is hard work and takes time (and by the way is something no one ever tells you when you start out on your own). I’ve written about this before in my piece I, consultant - but the gist is this: if you can find an identity you’re comfortable with you’ll feel safer making “insider transgressions” - i.e. fitting in at times. And often you’ll find that your assumptions about fitting in was flawed in the first place.

It’s important to look in the mirror and attempt to clearly see the client and your own behavior in context. In chapter 3 I claimed that often you’re the one blocking the client:

All of this talk of blocked clients however misses something important - in my own work, 80% of the time when you feel the client is blocked - it is you the consultant that is blocking the client!

The consultant’s ego places a high value on your own ideas - you want to be the hero that has the “right” answers. And in fact you can feel like a fraud if you work on a consulting project where you don’t have any original ideas.

This thinking will lead you into trouble.

So tread carefully, question the ego and seek to develop a strong sense of identity. Swallow your pride and seek ways of generative destruction not defensive destruction.

Remember: your outsider identity gives you energy and drive but can be taken too far.

You have to be careful not to fit in for too long though….

The Dangerous Fool: Outsider or Outcast?

The fear of the fool is to be an outcast. To transition from outsider to outcast (or worse to clueless). To be an outcast is to be an outsider that isn’t allowed in. For a free player consultant (vs a process consultant see definition) we’ve explored the winning move of surprise, but there are two losing moves:

  1. Fitting in for too long. Through fitting in and following the rules for too long we lose our outsider status and lose the ability to surprise our client. This path leads to employee-dom.
  2. Being boring. Even if we don’t follow the rules and fit in - if we fail to bring surprise then we become boring for our point of contact. This path leads to being marginalized and ignored - an outcast.

We can visualize this map in a 2x2 (drawn from the perspective of the free-player consultant or fool):

Becoming clueless - i.e. an insider incapable of surprise - is bad, but worse is being an outcast. The fear for indie consultants who are trying to “stay alive” (in the samo burja sense of live players and dead players) is becoming an outcast - being fully and completely rejected not just by one organization but by all organizations.

When client work dries up I feel this existential terror. Have I stopped being able to surprise clients?

The way through this is to recognize surprise as a core part of your identity - to be weird in ways that bring delight to clients. To prance, dance and perform for clients in ways that test boundaries, that explore new territory and question assumptions but without being rejected wholesale and becoming an outcast.


Recognizing and developing a sense of identity that is true and strong as an indie consultant is hard. It’s a long road. I hope this Yes! And… series has given some hope for those wrestling with organizations - attempting to change them, to see them, to work with them without falling into clueless or outcast status. To be effective and playful.

I sent a draft of this piece to an old client and she said this:

“Sending these over in case it sparks something….

Humor, Humility, and Humanity

These are words that come to mind when I hear “wink and a chuckle”. Initially I think Santa Clause and his deep belly laugh. I ask: “How does one discover or sustain childlike wonder in the workplace? How do we find humor when stakes are high and serious means business? How do we find humility in a world that has historically rewarded hubris?”

Rather than try and integrate this comment into the essay I want to leave it as is. How does one sustain childlike wonder in the workplace?

Form Keith Johnstone and Impro one last time:

What happens in my classes, if the actors stay with me long enough, is that they learn how their ‘normal’ procedures destroy other people’s talent. Then, one day they have a flash of satori—they suddenly understand that all the weapons they were using against other people they also use inwardly, against themselves.

Perhaps through changing clients we can change ourselves.

Thank you to the folks who reviewed early drafts: Toby Shorin, Erin Przekop, Brian Dell, Joel Christiansen, Richie Bonilla, Stew Fortier, Paul Millerd, Alexa Scordato, Josh Thompson, Nathan Snyder & Will Critchlow

  1. Thank you George Walkley for tipping me off to this paper! 

  2. Dear clients, don’t take this too personally - turns out everyone is terrible at describing their own problems! 

  3. Sidebar: There’s three ways to convince a company to do things: human stories (employees/customers are unhappy - look at them! - we must change), data stories (look at this compelling data, we must change) and competitive stories (unless we change, competitor X will crush us). 

  4. In this way the consultant can often break a stalemate - you can unlock projects and budgets that have been debated about for a long time. The outside voice can validate ideas and trigger change. Be mindful however that in breaking a deadlock you may end up choosing sides unwittingly….