Introduction

Who the book is for, and where we're going

The New York Times had a guacamole problem and they’d hired me to help. No, this wasn’t about peagate - when the times tweeted a pea-based guacamole recipe and pissed off the GOP and Barak Obama. No, this wasn’t about avocado politics, the looming reckoning of climate & labor emergencies that will re-shape our national conversation about labor and climate change.

Those issues would all come later. This was a more mundane issue: SEO (search engine optimization).

But it still felt high stakes to me - I was sat in the New York Times building, an imposing tower that defines an entire region of Manhattan - and it was only my second client since quitting my job and becoming an independent consultant.

Six months earlier the New York Times had assembled a new team to build new digital products. Headed up by Sam Sifton, editor at the NYT for 20+ years.

I was sat facing Sam Sifton, in a room covered by brightly colored post-it notes and printed mockups of website designs. This would be a familiar scene for any startup or technology company but felt rebellious or less typical for an imposing old institution like the New York Times.

I tried to explain the guacamole problem in plain language:

“The problem is that you have 26 recipes - and they all say “guacamole recipe” on them. When someone searches in Google, which one should they land on? Which one is the best guacamole recipe? And how do we differentiate the other 25?”

At the core of the problem was a tagging of all of their recipes - ensuring that we could index, display and talk about recipes in a way that optimized for how people could search for and find recipes.

The meeting went well. Sam liked the presentation and it felt like I’d explained the issues in a way they could understand and grapple with. As the meeting was wrapping up Ben French, then Executive Director, New Products, pulled me aside and confided that while he agreed that the guacamole problem was a real problem - the NYT Cooking site had only launched six months ago and the team had just spent a ton of time and cost on re-tagging every single recipe. Going through that process again felt insurmountable both from a cost perspective, but also an internal political perspective - it would make them look stupid to have to go back and ask for more money to re-do work they’d just done.

I’d come to learn many times over my consulting career that clients have a surprising amount of detail. No problem is easily solved, no solution is easily rolled out. There’s always layers of complexity lurking under the surface.

Walking out of the Times building I remember feeling a mixture of frustration and satisfaction. Satisfaction and delight at the ability to work on complex, interesting problems with a client as good as the New York Times - and stimulated by the creative challenge of how to help the Cooking team’s problem which was as much a technical information architecture one as much as an internal politics one.

But at the same time I was frustrated that the work I was doing was bounded inside this “SEO” container - limiting the impact of the work and sphere of influence I could have at the New York Times and trapping me back into a mode of work I thought I’d left behind.

I’d started my career doing SEO work but I’d deliberately left that identity and focus behind when I went to go work at Google. I spent two years there working on big ideas at Google scale(self driving cars, quantum computers, AI, those kinds of things). After quitting my job at Google I was excited to step into innovation, strategy and “big picture” work for clients. So it was rude awakening to find myself doing “SEO” work all over again.

Was this just a big step backwards? Would I ever be able to do the kind of work I wanted to do, working for myself?

6 Years Later…

Six years later in my consulting journey I’d find myself back working with the New York Times - in a matter of chance presenting to Sam Sifton again, who was still involved in new product initiatives at the Times. This time doing an entirely new kind of work: advising a senior executive on their internal status and influence and partnering with them on an innovation sprint to design a new product for the Times.

This work was not about solving problems but about being a co-pilot to my client, helping them to assemble a team, helping them to run the project and leading the project across research, product and design to ideate new products.

Pure “SEO” work was in the rear-view mirror. I was 6 years into my consulting journey and felt like I was just hitting my stride.

The first time I was brought in to work with the New York Times it was via my friend John. His friend Hannah worked at the New York Times and she was asking around for a recommendation. John, a close friend of mine and someone I used to work with put my name forward.

6 years later I’d come back to work with the Times via a friend Dorothy - someone I’d actually interviewed with before I even quit my job back in 2013 (over 7 years previously!).

The Three Themes of the Book

This journey with the New York Times as a client sets the stage for the journey I want you to discover reading this book. My hope is that the book can help you with the practicalities, like how to generate clients, but also with the intangibles of expanding the kinds of work you do - doing it on your own terms, finding the kind of work that lights you up so that you can sustain your freelancing and consulting career for a very long time.

Three big ideas from the work with the New York Times anchor the themes of the book: how clients come through your network, why changing clients is hard and requires delicate work, and how your personal narrative and identity is a key component of your success.

1. Interdependent Networks

From independence to interdependence. The first few chapters look at how generating clients is truly a function of your network - and that networks have some surprising properties (like you’re statistically likely to have fewer friends than your friends)

Chapter 2: strange attraction Chapter 3: weak ties and strong intros Chapter 4: rejecting specialization

How to generate clients, how to reconcile the idea of “positioning” that is typically hard for indie consultants.

2. Improv as a tool to change clients

Giving advice is a tricky business, and it can feel frustrating. Clients get in the way of your good ideas all the time! But if you want to build a sustainable, effective consulting practice you need to find a way to enjoy the resistance. To embrace the fact that changing clients is hard.

Changing clients is hard. They’re primed to reject change, they’re designed to be stable systems. As an outsider we need to first understand the real reason we’re there and then find surprising ways to effect change.

The archetype of the fool helps us navigate the internal/external role of the consultant. In this section we’ll also explore why perhaps “solving problems” isn’t the real role of the consultant in the first place.

3. The inner game of consulting

In this section we address some of the causes of burn out: energy management, overwork, and identity. The benefits of consulting are easy to understand: money, time, freedom. But the downsides are harder to anticipate: grinding of gears with your relationships, managing your ever-changing identity, sustaining your curiosity and intellectual interest in the work.

The Consultant’s Grain

A few years ago I went hiking in the redwoods with my family. These trees are hundreds of years old, and grow to be hundreds of feet tall. Standing next to one you can place your hand on the trunk and feel a deep thrumming

Looking at the tree rings of a redwood tree you can see a kind of story told over centuries as the tree grew. And yes, this extended vacation traveling through California was enabled by my consulting practice - the cash and calendar freedom to travel and spend time with family.

Just like the redwoods, every consultant is unique. Your personal story and history is written in the grain of your rings. There’s no escaping who you are. But you can recognize and embrace the introspective work to understand your own ideas, perspective, strengths and yes flaws.

My hope with this book is to give you some practical advice but also expand your way of looking at consulting and maybe, just maybe help you transform your practice. To help you build your own weird, unique practice that embraces your own grain.

Enjoy, The Consultants’ Grain.

Tom Critchlow, June 2023

Discarded writing

It was only my second consulting gig after quitting my job and going independent - sat in the imposing New York Times offices I was in a room that is familiar to startups and technology companies but perhaps less familiar to companies like the New York Times: a room with the walls covered in post-its, print outs of web design mockups and whiteboard scribbles. The NYT Cooking team was part of a new digital products team - building new technology products out of the editorial materials and expertise across the times. And like I said, they had a guacamole problem. I was sat facing Sam Sifton - an extremely enthusiastic, charismatic and senior figure and long time-editor of 20+ years at the New York Times. Sam didn't know much about SEO but he was willing to engage. I was trying to explain the guacamole problem in plain language: > "The problem is that you have 26 recipes - and they all say "guacamole recipe" on them. When someone searches in Google, which one should they land on? Which one is the best guacamole recipe? And how do we differentiate the other 25?" This was my second consulting --- In 2015 the New York Times tweeted out a pea-based recipe for Guacamole and all hell broke loose. Before the week was out, the Texas GOP was saying "The @nytimes declared war on Texas when they suggested adding green peas to guacamole." and even Barak Obama was “Respect the NYT but not buying peas in guac." What would later become known as "peagate" was a classic mid 2010s classic social media firestorm. And maybe it was a little, tiny bit my fault? Rewind the clock to one year before - it's 2014, the New York Times had a guacamole problem and they'd hired me to help. I was sat in a large meeting room, walls covered in post-its and page designs printed on the wall, presenting to the NYT Cooking team. I was there to help with their SEO problems. On the other side of the table sat Sam Sifton, a charismatic beaming enthusiastic figure and also a long-time editor of 20+ years at the New York Times. Sam didn't know much about SEO b but was willing to engage. I was trying to explain the guacamole problem in plain language: > "The problem is that you have 26 guacamole recipes - and they all say "guacamole recipe" on them. When someone searches in Google for "guacamole recipe" which one should they land on? Which one is best? And how do we differentiate the other 25?" This project was my second freelance consulting project since I quit my job and I was feeling incredibly fortunate and frustrated at the same time. On the one hand I was sat inside a magnificent building (you know what Times Square is named after right?), working for an amazing brand - the kind of brand you aspire towards working with, and it was only my second freelance client! On the other hand - the work was firmly SEO work, and I was viewed as the "SEO consultant" in the room. Yes, the kind of work I knew very well but not the kind of work that I had dreams and aspirations towards. And yet, even though this was on the surface a kind of work that I wasn't that excited about it still provided opportunity for the client to contain a surprising amount of detail. One of the hard things about consulting is that "simple" recommendations rarely prove to be simple. This NYT project was no different - I was feeling pretty good after managing to explain the problem with their taxonomy and tagging structure in a way that Sam Sifton would understand. But it turns out that diagnosing the problem was simply the first step in a long, complicated journey. As the meeting was wrapping up Ben French, then Executive Director, New Products, pulled me aside and confided that while he agreed that the guacamole problem was a real problem - the NYT Cooking team had just spent a ton of time and cost on re-tagging every single recipe. Going through that process again felt insurmountable both from a cost perspective, but also an internal political perspective - it would make them look stupid to have to go back and ask for more money to re-do work they'd just done. We'd have to find another way. This is the part of any client engagement that gets me excited - where you realize that there's a real texture to a client's problems. There's no simple "re-tagging" project - it's a mixture of internal politics, creative ideation and maneuvering to help the client find a version of the project that will be effective AND get buy-in internally to be able to be implemented. ## About Me My background - what I bring to the table. I've been doing some form of "consulting" work since 2007. First helping launch an SEO agency - I ran the consulting part of the business, first doing the work myself, then managing a team of consultants working on client work. Later I'd join Google and work with the Creative Lab and BizOps teams - straddling various forms of intrapreneurship - effectively consulting with various teams and projects across the business (including designing presentations for Sundar who would go on to become Google's CEO). Since 2014 I've been an independent consultant working for myself across a variety of clients. The work has evolved in that time from tactical "SEO" work to more senior and less well defined work I do today like advising CEOs, putting together business cases for investment and more. Throughout my own journey I've found that writing about independent consulting was generative and useful for me personally, that people liked it and that a lot of my best advice ran counter to some of the accepted wisdom. Hence this book. There are as many different approaches to consulting and freelancing as their are consultants and freelancers. So why write a book at all? Why claim to offer advice? Well this book isn't really about advice. It's hopefully a guide that can help you integrate "what works" with "what works for you" - to enable a weird, messy, creative practice to emerge that can sustain, feed and nourish you for a decade plus. That's why this book is called The Consultant's Grain - your own unique ideas, perspective, and yes your flaws - they all play a part of making your own unique practice and you need to do the introspective work to understand yourself in order to be able to properly construct a practice that can sustain a decade or more of work. Tom Critchlow, 2023.

The Strategic Independent

1. Intro

2. Becoming Independent

3. Finding Work

4. Ways of Seeing

5. Yes! And...

6. Chronos & Kairos

7. The Inner Life of Consultants

8. Appendix