Chapter 2. Finding Work
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 10 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 2024!

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

Rejecting Specialization

Using vibes and voice to attract the right clients

June 16, 2022

There are two types of indie consultants. There are those that have created a very clear specialization, you can look at their website and see something like “I help B2B SaaS companies with their content strategy” or “I help brands build audience via email”. The indie consultants that do this well seem very busy, well known and respected in their industry. It’s fairly easy to see from the outside what their work looks.

Then there are those who are… weirder, less legible, harder to define. Folks who’s website doesn’t have a tight “I do X for Y”. These people likely project a weird sensibility via their online writing and persona, building a body of work that points to a kind of vibe.

It’s easier to see from the outside when the first group is successful, and it’s fairly easy to imagine what the work looks like. The second group is much less legible. Are they successful? What kind of work do they even do?

There are plenty of success stories for the first group - lots of books, articles, podcasts and case studies. If you read around you might think that you should follow in their footsteps, that this path is both more successful and easier.

But I don’t buy it. I’ve been an indie consultant for 8 years and have built a network and community of fellow indies. I’ve had many open and honest private conversations with indies about money, success and anxiety. Through these conversations I’ve come to two realizations:

  1. For many indie consultants who have rejected the 9-5 of full-time employment, trying to specialize and box yourself in is a path to burnout and failure
  2. This second group of weird indie consultants is often just as successful as the first group (if not more so) - they’re just less vocal about it

So in this post I’m going to reject the commonly accepted wisdom and look at why specializing is hard, why it fails and what an alternative path looks like. The answer lies in developing strong opinions and a distinctive vibe.

Specializing is “not even wrong”

If you look around at common advice for indie consultants you’ll get told to specialize: to create a narrow definition of who you’re serving and what you offer.

You might think something like: “If only I could clearly articulate WHO my ideal clients are and WHAT they want, then I could figure out how to drive leads”. There’s plenty of conventional wisdom that supports this idea. As Philip Morgan says in his book The Positioning Manual for Indie Consultants:

To get ahead with your consulting business, you need to create visibility in the market and earn enough trust to make selling easier. These two things, visibility and trust, are much easier to get if you SPECIALIZE in something, in some way.

Philip is right about trust and visibility being important. Trust is important because we want senior clients primed for strategy work. Visibility is important because we need clients to know us and find us.

But specializing? Philip isn’t exactly wrong about specializing - in theory specializing is the most viable way to create a steady stream of clients. But, in practice, I often see this path being the wrong option. The problem is that good specialization is exceptionally hard. And mediocre specialization has two core problems:

  1. It attracts less senior, more tightly defined work that traps you in a mode of repeatable execution work
  2. It puts you in a well defined box that grinds against your identity

We think that the primary function of positioning is for the market - for clients to better discover and hire you. But I’d argue that positioning is primarily for your own ego. It’s an inner game of figuring out who you feel comfortable being, more than a driver of clients.

Specifically, many independent consultants are generalists - trying to find interesting, senior work. They crave an escape from the narrow confines of 9-5, and it’s incredibly difficult to reconcile a narrow specialization with your quest to be a senior generalist. This is a classic failure mode that I see time and time again: generalist indie consultants trying to fit themselves into a narrow positioning just to try and manufacture clients and in the process causing themselves stress, anxiety and ultimately burn out.

This anxiety is real. Feeling the peer pressure and established wisdom pushing you down a path to specialize - despite the fact that it grinds against your identity. You feel like you “should” do it. But I’d argue that for most indie consultants, you’d be better off leaning into your uniqueness and point of view as a way to generate senior clients consistently.

Why is Specializing Hard?

The problem with the advice to specialize is that it’s not even wrong! The advice is correct - IF you can create a narrow positioning, if you can become a visible, trusted expert in a particular niche then you will attract clients. It will solve your problems.

But it’s a big IF…

The advice is not even wrong because most independent consultants can’t create a narrow positioning. The problem is that we think choosing a specialization and positioning is based on looking at the intersection of work we’re good at and what the market wants.

This is hard enough to do - especially in the early days of consulting when you don’t have enough work yet to really understand what you’re good at or what the market wants. But once you start to figure out some kind of product/market fit for your consulting you start to uncover a third, hidden agenda:

This third agenda is why specializing can lead to burnout. We’re not just looking for product/market fit for our consulting work - but our consulting work is deeply tied to our identity and we need a way to make it sustainable. This third hidden question is why specializing is so hard and even impossible for many independent consultants. Even if you can choose a specialization that meets the top two circles - something that you are good at that the market wants - can you reconcile that with your sense of identity? Can you craft an identity that you feel comfortable with, that gives you energy? Are you comfortable with who you might become?

Example: The obvious and “correct” positioning for my own consulting work should have been some variation of SEO consulting. My history in the SEO industry meant that I had visibility and trust. I’d spoken at conferences all around the world, I’d worked with big brands.

But I also saw the SEO industry as a dead end for me personally. Not that SEO is doomed or irrelevant but it wasn’t the path I wanted to follow to ensure I was challenging myself, broadening my horizons and working on new creative challenges.

This led to a lot of internal angst. Should I follow the standard path and do the work that I’m well known for and can comfortably deliver? Ultimately I decided to iterate my way out of SEO - to take the familiar SEO work to pay the bills in the early days but to aggressively pursue bigger, more strategic and more creative kinds of work. It took me 1-2 years to feel like I’d really “escaped SEO” and was on a new path to new kinds of work.

This kind of internal angst is very common - there’s a clear path to follow but it’s known and well understood. And you didn’t set out as an independent to follow paths you’ve already walked…

The biggest fear of independent consultants when specializing is not just that it will narrow your options - but that will take you down a path you already know.

Many independent consultants are independent for a reason - we’re contrarian, we’re attracted to a myriad, varied array of work. We chase novelty and surprise - we’re often seeking an alternative path. And specialization doesn’t lend itself well to novelty and surprise.

Instead, especially in the early days of consulting, you’re chasing the greatest possible surface area of distinct clients in an attempt to better understand the interplay of what you’re good at, what people will pay for and who you want to be.

And it’s not just paying clients you’re chasing - you’re chasing senior clients paying good money for interesting work.

The Hidden Price Ceiling of Specializing

Good specializing is hard, because if you don’t do it well, you can end up trapping yourself. By creating a narrow positioning or specialization you make yourself more legible and understandable - you’re essentially optimizing for well-defined work. And well-defined work is less senior, less well paid and less interesting.

You can separate most work into two buckets: well-defined and ambiguous.

Well defined work is the kind of recognizable work where the client has clarity around both the problem and solution. This is the kind of standardized work that you see agencies pitch - things like “content strategy”, “user research”, “SEO audit” or “website design”. Well defined work has clear naming and down this path you see work that has an RFP and multiple competing vendors. Well define work is won by tight positioning.

Ambiguous work on the other hand is where either the problem or solution are not fully formed. Perhaps the client has a goal like “how do I expand my business into a new country?” but an unclear solution. Or perhaps they have a problem “growth has stalled for our agency” and lack clarity about both what is causing the problem AND what a solution would look like. Here the client doesn’t even know the shape of the work - so they need to rely on a kind of vibe to select the right consultant.

This distinction between well-defined and ambiguous work has a lot of implications…

Well Defined Work Ambiguous Work
Client has clarity of problem and solution Client lacks clarity on problem and/or solution
Requires strong positioning to capture Requires vibes and point of view to capture
Feels like freelancing Feels like a blend of coaching, consulting and advising
Standardized work with multiple competing vendors / agencies Non-standard work often in non-competitive pitching situations
Lower hourly price point Higher hourly price point
Less senior More senior
Tends to be shorter / project based More likely to lead to ongoing retainer
Requires clear case studies that show you’ve done this work before Requires alignment between ways of working and view of the world
Clients can come from “cold” channels Clients require warm intros and personal introductions
Able to be decomposed into tasks that a team can tackle (i.e. agency is a good fit) Hard to decompose into tasks so a good fit for a single individual (i.e. consultant is a good fit)

In short, not only is ambiguous work more fun and interesting - but crucially, it’s more senior. If you want to push into more senior work with long term well paid retainers, then you need to push into ambiguous work.

All Senior Work is Ambiguous

A VP of product or a CMO doesn’t get that role just because they are an expert in product management or an expert in marketing. They get that role because in addition to some product or marketing expertise they also have a blend of senior skills - across communication, leadership, management, vision and the ability to get things done.

As you get more senior, the focus and emphasis on narrow domain skills gets replaced with a more ambiguous blend of skills and expertise, a kind of executive presence.

The problem with a carefully crafted positioning is that it typically makes the wrong part efficient - it makes it easier for clients to hire you for well defined work. It allows greater legibility, trust and expertise around work which is well defined.

This is a trap that I see many indie consultants back themselves into - through creating a narrow positioning they end up optimizing for lower quality client work. They increase their dealflow for clients, but only for smaller, less valuable and less senior clients. This results in ending up delivering a lot of routine work. It can fill your pipeline but leave your soul empty.

Instead, what senior clients want from a consulting engagement is not just skills or expertise, it’s experience and momentum. They need to move their org in a direction that it’s currently resisting - and so they look to outside help to kickstart a new direction and provide fresh energy and momentum to get something new off the ground. (This is capacity building consulting like I’ve talked about before).

Great positioning, if you can pull it off, can lead to ambiguous work

Let’s acknowledge that great positioning and specialization can lead to ambiguous work. It’s very rare to see this kind of specialization - it’s very much the exception, not the rule. But let’s take a look at an example.

Example: Andy Raskin is a consultant specializing in “strategic narrative”. His website says:


In these engagements, I help venture-backed CEOs and their leadership teams align around a high-level story that powers success—in sales, marketing, fundraising, product development and recruiting—by getting everyone on the same page about strategy and differentiation.

This is a rare breed of specializing - that allows you to both define a senior audience and define the work, while still leaving room to drive a bus through in terms of how this work is actually delivered. Note that Andy’s use of “strategic narrative” is essentially defining a proprietary approach and type of work.

You easily imagine how this specialization allows for senior, ambiguous work that leads to ongoing retainers - I can imagine how this strategic narrative impacts every part of the organization so it could easily lead to all kinds of work. But - you have to ask yourself carefully if you’re able to create this kind of senior and ambiguous specialization… Most can’t.

(And as we’ll see later much of Andy’s success is due to his strong opinions, not just his positioning)

So, if we’re rejecting specialization and mediocre narrow positioning - how do we generate clients? Getting a steady pipeline of clients still requires trust and visibility - but we can understand it better through this lens of ambiguous, senior work.

Specifically, clients need trust that you can navigate the ambiguity reliably without close supervision. And you need to be visible, not just publicly but inside their inner circles. After all this senior ambiguous work often flows through dark leads in cozy spaces.

In the rest of this piece we’ll look at how strong opinions create the kind of trust and visibility required for senior, ambiguous work.

Part 1: Strong Opinions

Let’s return to the goal: sustainable client leads for well paid work without sacrificing our personal identity or narrowing our focus.

It turns out that having strong opinions with a distinctive vibe works remarkably well. Strong opinions:

  • Travel well - they’re designed for distribution and visibility in our networked age
  • Allow you to get good client/consultant fit for senior, ambiguous projects
  • Signal a creative energy that clients are looking for to catalyze change in their organization

But, unlike specialization, strong opinions don’t narrow down your options or grind against your identity as a generalist. Strong opinions allow for divergent, generative futures.

Example: My friend and fellow independent Behzod has a background in user research and instead of creating a strong specialization he covers all kinds of work related to user research under his studio moniker Yet Another Studio.

He has strong opinions. He has developed a point of view on a contentious topic within the user research community - whether or not to democratize research. He takes a stand with a strong opinion: Democratization is our job.

This single piece (which started as a podcast talk, became a conference talk and then a blog post) has generated a ton of client work for him - leads that come to him well primed not for him to “do user research” but to “create a user research practice” - specifically the kind of senior, ambiguous work that is better paid and longer term than simply executing on a user research project.

Let’s take a closer look at how this works:

Publishing Strong Opinions Gives You Visibility

This might seem obvious but it’s important to restate it: strong opinions are what distribution is made of. Every independent consultant should be working in public in some form - it’s how you generate awareness, clients and visibility.

But working in public is more than just publishing content - it’s about creating connections. We’ve explored before how working in public leads to expanded connections and how content drives leads even from weak ties. Working in public, producing content is about creating connections. About shaping your image in other people’s eyes. It’s how you build friends, collaborators, advocates and clients.

The key of course is to make content that’s memorable and distinctive. In short: content that has a point of view. Whether it’s a clearly articulated point of view with a rational argument or just an aesthetic and vibe.

Not sure how to start? Small-b blogging and blogpunk make a powerful combination.

How do you tell if you’re doing it right? As you build your publishing practice the only measure is connections. How many conversations are you having because of the things you publish? Forget audience size, forget pageviews - focus on crafting your voice. Focus on building a voice that makes people want to have a dialogue.

When you make the leap from full time employment to being independent you leave behind a lot of the traditional forms of authority - platforms are harder to access. When I worked for Distilled, an SEO agency I was speaking at 20-30 conferences a year. Since being independent I’ve spoken at… 4 conferences in 8 years?

Once the labels, platforms and access are taken away it’s much harder to create an audience, you need to create a voice for yourself.

Example: Lindsey Slaby is an independent consultant working on ambiguous and senior level consulting projects in the ad agency world. Lindsey specifically works at the messy areas that others shy away from: contracts, pricing, contracting, agency roster selection and more.

Over the years Lindsey has developed strong opinions about how the industry works, unafraid to shine a light on uncomfortable topics or take contrary positions. For example this piece on RFPs and why companies should be pitching agencies (when the received wisdom is that agencies should be pitching companies!)

Vibe Fit and Trust in Navigating Ambiguity

More than raw distribution though, exposing your style and sensibility is important. Not just for standing out in the networks and generating dialogue and discussion - but also because senior, ambiguous consulting work relies on navigating a trust gap like no other.

Having an opinion is like having taste. It demonstrates a sensibility and way of thinking that is key when a senior client is considering a consultant for a project.

As we outlined in the defined/ambiguous section - ambiguous work requires an extreme amount of trust. When the situation is well defined - clients don’t need as much trust because they can control the situation more closely: they have a better understanding of what’s going on, they are able to hire replacement vendors easily and they can rely on outside experts more comfortably.

For ambiguous work it’s not so easy. In this case the client is relying on the consultant to both diagnose the problem AND provide potential solutions. It’s often the case that the client is operating in unfamiliar territory and needs to simply trust the consultant in all kinds of ways. There’s no easy way to replace the consultant or verify the advice being given. Simply put, oftentimes the client (and sometimes consultant!) are operating outside of normal boundaries.

So trust is essential - but more than that, you need to trust that the consultant will make the right decisions even faced with unknown unknowns. This kind of taste is hard to signal with a positioning statement. To develop this trust in someone without actively working with them before requires a strong understanding of the person’s point of view and vibe, which is why sharing your point of view in depth matters.

Vibes & Destabilizing Energy

More than just trust however, ambiguous work requires a specific kind of energy. Consulting is about changing clients. You’re often an outsider, brought in to catalyze some kind of change that the client has been unable to change on their own. Playing this role of catalyst (or, said more strongly: destabilizer) is challenging. Push in the wrong direction and clients will reject you. Push too hard and the client will collapse into chaos.

This delicate balance means that senior leaders need to know that you can put yourself in their shoes. Less like a vendor where they tell you what to do, and more like a peer that they can spar with.

So prospective clients need to trust that you get not just how the industry works but how their specific culture functions. They are looking for a very specific kind of energy - enough energy to change and destabilize the org, to provoke the organization to change, to create momentum for new projects. But not the wrong kind of energy to tear the client’s organization apart - creating strife and disruption.

In short, vibe is how you find a good client/consultant fit.

Building vibes is a different kind of work from specializing. You’re not just demonstrating expertise and competence but compatibility.

In optimism as an operating system we explore the human side of consulting and the common trap of the negative consultant. As you think about exposing your vibe you need to think carefully about how to develop opinions that have a point of view without positioning yourself with the wrong kind of destabilizing energy.

So we’ve covered why specializing can be the wrong move, explored why having a point of view is useful for generating senior, ambiguous consulting work and why publishing and writing in public is the way to create a vibe that a client can trust and be compatible with.

But how do you develop a point of view? And in particular how do you do it authentically without resorting to cheap shots and portraying the wrong kind of negative destabilizing energy for potential clients?

Part 2: How to cultivate a point of view

Developing opinions is hard. Translating opinions into a credible point of view is even harder. Doing it without pissing people off is harder still!

The good news is that, unlike specializing, developing opinions, crafting a point of view and building a vibe is an iterative, generative process - once you start trying out your voice there’s a feedback loop that helps you develop your voice and strengthen your point of view.

It’s hard to see which parts of your experience and opinions are distinctive and resonate without sharing them. In my experience, it’s rarely the big grand vision that people are attracted to but rather something more mundane and grounded - something that has a clarity and weight about it that is distinctive.

Let’s explore two different approaches to finding your voice and point of view: “20% beefs” and the gap between industry and practice.

20% Beefs

This is a concept that Venkatesh created in his email newsletter Art of Gig. I’m quoting liberally from it because it’s no longer online (with Venkat’s permission):

The top 3 articles of the hundreds I’ve written, in terms of how much they drove cold inbound leads for consulting gigs, are the following. What feature do you think they have in common?

It’s not that they are dark and satirical or contrarian. I’ve written other dark/satirical or contrarian things that led to no gigs.

It’s not that they showcase deep expertise in a subject. They don’t. In fact they largely showcase my shallow, self-taught amateurishness on the underlying topics.

It’s not that they offer step-by-step playbooks to solving the problems they frame. They don’t.

The correct answer is that they each pick a beef worth picking, but not too strongly.

  • The Gervais Principle picks a beef against feel-good “nice” management thinking that dominated the pop-business literature at the time (I helped drive the surge of interest in darker understandings of business circa 2009-12 I think).
  • Entrepreneurs are the New Labor picks a beef against people in the tech sector shilling what has come to be known as “hustle porn” and flattering founders with a Hero self-image that blinds them to industry dynamics and debilitating behaviors.
  • Fat Thinking picked a beef with the lean six-sigma crowd in big corporations, and the lean startup crowd in the startup scene.

But importantly, none of these is what you might call “pure beef” where the fight and criticism of an opposed perspective are the main focus or content.

They are what you might call “20% beef.” Where the starting point is rejecting some core sacred-cow axiom of a prevailing orthodoxy, and then building something new and interesting, based on additional ideas and novel elements, on that foundation of principled dissent. It is something like rejecting Euclid’s parallel line postulate and going out on a limb to see if you can build a non-Euclidean geometry.

For example, the assumptions I rejected in my 3 articles above are:

  • Executives are nice and managers know what they’re doing (Gervais Principle)
  • Entrepreneurs/founders are heroes (New Labor)
  • Efficiency and optimization are good things (Fat Thinking)

So one good answer to how to bootstrap from 0 to 1 is: indie consultants bootstrap with beefs. It’s not the only way, and it’s certainly not the safest way, but it’s a fun way that is very intellectually satisfying and validating when it works, and is the opposite of soul-destroying and dehumanizing.

Venkatesh goes on to outline a bit of a “how-to”:

Discovering and developing a genuine beef into an artful calling card that lands you gigs is hard work. That’s why it’s a costly signal. You can’t fake it by simple bullshitting.

You have to put in the work of:

  1. Spotting a widespread pattern of disillusionment in the margins
  2. Identifying the prevailing orthodoxy driving the disillusionment
  3. Analyzing its foundations
  4. Rejecting one or more flawed premises driving the disillusionment
  5. Adding imaginative alternative premises
  6. Running with it to see where the whole thing can take you
  7. Becoming conscious of what and who you’re for and against
  8. Articulating it out there in public and standing behind it.

[…] The work is hard not because it takes effort or time. None of those articles took me more than a couple of days to write. The work is hard because it takes a certain amount of courage and a good deal of taste. If you don’t feel a bit of an adrenaline rush, a sense of a fight-or-flight, a sense of burning bridges, while working on them, you’re not doing it right.

20% beefs are like proof of experience - you can’t properly beef with an established way of thinking without first deeply understanding the orthodoxy. And I think this is the root of the power of 20% beefs - they demonstrate taste, point of view and experience all in one.

You can see how this recipe from Venkatesh is literally a playbook that you can follow - first through observing your own consulting work and the disillusionment that exists in the margins (from clients, agencies, fellow consultants etc) and then later from trying out some light rejections of the orthodoxy - both in private (with clients and potential clients) and in public (by blogging).

This line of inquiry is a healthy one for any consultant to take anyway - it’s the role of the consultant to play the fool and take contrary positions, ask stupid questions and check the first principles of everyone’s thinking.

The Industry/Reality Gap

20% beef is a recipe for developing a strong opinion - but it doesn’t really give you much insight into where to look. What kind of orthodoxy should you be analyzing and rejecting?

Looking at successful examples of 20% beef we see that there’s a common theme of analyzing the gap between theory and industry. The unique vantage point that the consultant has is the vantage point across multiple clients - sometimes across multiple industries too.

Through the nature of being embedded inside organizations, consultants often get a richer, closer look at how things are actually working. This enables you to develop a more realistic view of “how things work” than either in-house folks (who get to see inside a limited number of companies) and agencies (who only get to see the surface level of their clients).

Behzod’s example of “democratization is our job” was developed from first seeing how research operated inside Facebook and Slack and then from consulting with a range of other startups. It’s this view of “how things actually are” that allowed him to develop a beef.

Similarly, Lindsay Slaby’s perspective of “clients should pitch agencies” was developed from deep experience seeing how pitches actually work, and how much clients struggle to attract top quality talent - directly straddling the client/in-house divide and seeing the challenges from both sides.

In every industry there’s typically some kind of received wisdom that sounds like good rational advice but simply doesn’t hold up when faced with reality.

The trick is to look for advice that is “not even wrong” - advice that is correct in a certain sense but fundamentally unhelpful when applied to reality.

The consultant occupies a unique position being able to see both across multiple clients AND to see further inside client organizations than agencies can. By embedding yourself deeply inside client organizations and working with senior leaders you can see the real challenges they face and how they behave - you can get underneath the surface of “good sounding but useless” advice.

Here’s a simple example to illustrate the point. In the SEO industry the commonly accepted way of delivering SEO work is via SEO audits. It doesn’t take a genius to observe these SEO audits in practice to see that they’re commonly less than worthless.

Not only has every sufficiently large organization already received several SEO audits in the past from a variety of agencies and vendors but an SEO audit is also not the most effective way to drive change and achieve SEO goals. You can see how you could construct a 20% beef perspective for the SEO industry via rejecting SEO audits as a way of delivering work.


In conclusion, while the commonly accepted wisdom is to choose a niche and specialize, for many indie consultants it can be the wrong choice because:

  1. Specializing often optimizes for well defined work, which is less senior, less well paid and less interesting
  2. Specializing can grind against your identity as a generalist

Because of this, I’ve seen many indie consultants burn out trying too hard to fit themselves into a niche. Instead, developing a point of view and signaling a vibe can be more effective because:

  1. It optimizes for ambiguous, senior, well-paid work that is more interesting
  2. It doesn’t box you into a single identity
  3. You can iterate and explore your way towards a point of view

Developing a point of view is a long journey, and it’s not easy. But it’s a more forgiving path than specializing. Recently I’ve been toying with the idea of phases for indie consulting and you can see how the various phases align with how you notice, develop and share your point of view:

Year Phase Steer by Find clients by Point of view
0 Zero to one Sending invoices for any kind of work Any means necessary Put all your work in one place and try and make sense of it
1-2 Getting started Experimentation, figuring out your product / market / identity fit Being visible, starting a newsletter/blog, joining networks Notice what parts of your work and opinions make clients pay attention
3-4 Finding stability Cash freedom, number of good clients Beginning of POV development, writing around your topics, finding peers Writing consistently in public on topics you’re energized by
5+ Finding freedom Cash AND calendar freedom Direct POV development, starting communities 2,000 word essays on POV

And don’t forget to stay weird and foolish.