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The final Yes! And... piece: 🃏The Contrary Consultant

Pictured: me, walking into a new consulting engagement

Orientation: hi, it's me Tom Critchlow - indie consultant, blogger and lover of bright clothing. You probably signed up at tomcritchlow.com

I'm really excited to publish a new piece today. It's the last in the 5 part Yes! And... series and wraps up the longest series of writing I've done to date. When I first read the book Impro by Keith Johnstone I had the idea for a blog post about the power of "Yes! And..." and opening up clients through learning from improv acting. As I began to write the words kept going and the initial draft became three separate pieces. In the process of writing those three pieces two more were spawned and finally the series is 15k+ words.

Phew.

Honestly I'm really proud of this series - I think it's some of my best writing and I'm exploring ideas and concepts that I think are lacking in the discourse around freelancing, independent work and consulting.

If you're new to the series here's the overview:

Part 1 - The Office is a Theatre for Work. This post looks at the central problem of “performing” work and how important it is for modern knowledge work. How to think on your feet without resorting to BS.

Part 2 - Optimism as an Operating System. This post highlights the tendency for consultants to be critical and to see everything as a problem and how optimism can be a more powerful tool, especially for long term retainers.

Part 3 - Blocking & Unblocking Clients. Treating clients as blocked actors we explore how to generate & co-create strategy. Ultimately finding that the consultant is often the one blocking the client.

Part 4 - Navigating Power & Status. How to get things done inside organizations by understanding power potholes and status switching.

TODAY! Part 5 - The Contrary Consultant. Embracing the fool & the power of not fitting in. We explore the identity of outsider and how to reconcile this with working inside client organizations.
 

Playing the Fool

This piece is important to me and explores the identity of indie consultants - from feelings of being an outsider to the fear of being an outcast. And ideas of generative destruction vs defensive destruction and how holding too tightly to your identity as an outsider can be damaging for clients.

There's even a 2x2 with yours truly on the graphic design 1s and 2s:


I'm excited to be done with the series and proud of this one in particular. Now I can finally move onto some other chapters and sections of the book!

I'd love to know what you think.

Much love. Stay weird and foolish,

Tom
 
#40
August 17, 2020
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Two salons for indie consultants this week!

WFH consulting has it's perks - like when your 4 year old daughter doodles in your notebook

​Hey - it's me Tom Critchlow - indie consultant, blogger, firehose drinker & now accidental organizer for a discord community for indie consultants.

Just a short note this week with some updates. The !& discord community (pronounced: Yes! And...) continues to provide stimulating discussions and connections with other indie consultant types. Open invites are closed but if you're on the tinyletter use this link to access.

Last week we hosted a discussion around "small group consulting" inspired by a set of articles and readings. We meandered to the point - but ended up with some interesting reflections around alumni networks - how powerful they are for indie consultants and how you might manufacture them if you're out on your own.

Read my writeup here: Generating an alumni network for indies

Perhaps this discord space might become almost like an alumni network?.....

Two Upcoming Salons This Week

  • Tues Aug 11th @ 1pm ET: a "hire me" page group crit session. RSVP here.
  • Fri Aug 14th @ 12pm ET: using Roam for indie consulting. RSVP here.


Some links

Here's some stuff:
  • For media aficionados this NYT interactive art critique is sublime in both medium and message. If anything I think it's *better* on mobile than desktop. (Makes me think - how hard would it be to replicate this in an AMP story format?)
  • Talking of custom essay formats - I have been collecting some examples in this Twitter thread. Ping me if you know of good examples!
  • My friend Kyle Monson is starting to do some "thinking in public" for his agency and I think it's a great example of how being open can be interesting. Follow, subscribe, etc. Kyle is one of the good ones.
  • Last week I pounded some ciders one evening and fired up a thread with some generic observations about business. People seemed to like it.
Next - look out for me finally finishing part 5 of the Yes! And... essay series, re-launching Little Futures with my friend Brian and a custom-essay-template-thing... What are you working on?

Much love,

Tom
#39
August 9, 2020
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Discord update #1: Focusing on indie consulting & next salon with Matt Webb

Programming: Hi there - it's me Tom Critchlow. I have a website with bright green boxes. I'm an indie consultant, blogger and art lover. Thanks for being here.
Live scene from our last discord + figma jam session

Just over two weeks ago (more or less on a whim) I set up a discord chat space. The idea was to create a slightly more cozy "chat" space for realtime interactions that wasn't Twitter. In two short weeks the community is now ~200 people and I have some clarity for what it's for:

Key Updates:

1) It's clear that the primary driver and value for this community is around independent workers and indie consulting. So that will be the focus of the community moving forward.

2) I'm closing the open invite to the discord. If you want to join grab this link. Moving forward I'm going to let people in more slowly and carefully. (Note: referrals are always welcome so ping me with reccs)

The two salon's we've run so far have been wild, chaotic and full of energy. I'm really inspired by the energy and conversations coming out of these. These sessions are not recorded but I wrote up the output from the two sessions:

The Indie Business Model Canvas V0.1 - check out this template for reflecting on your own indie practice. I created my own canvas (linked in the post) and found some useful reflections on my own business.

Notes on Thinking in Public - a wild garden of ideas around thinking in public. (Ping me if you want to hire me to help your organization create more interesting "thinking in public")
 

The Next Salon with Matt Webb

Matt Webb is a fellow indie consultant - ex-BERG and all round fascinating human. I've admired Matt's work and his thinking for years. He recently wrote a great little meditation on generating consulting work during the pandemic: Sales pipelines, consultancy, and navigating the lockdown and I instantly invited him to come run a salon session in the discord.

It's going to be a presentation from Matt followed by group discussion around lead gen and surviving as an indie during these times.

Salon: 11am ET next Tuesday 28th

Add the event to your calendar here.

See you there

Much love

Tom

#38
July 22, 2020
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Create an Indie Consulting Business Map - Salon 1pm Tues 21st

Programming: it's me, Tom Critchlow. your friendly internet weirdo. This one's a short one.

I wrote previously about starting a discord space for real-time interactions. Earlier this week we got together for a fun and chaotic session about "Thinking in Public".

It was a huge success - it felt intimate, useful & interesting. I wrote a bit of background about why it felt intimate and why that's important to me here: opening up in open spaces.

So - I'm going to do it again:

Tuesday (21st) - 1pm ET: Creating an Indie Consulting Business Model Canvas

To join - just show up the discord #salon voice channel at 1pm (invite link to discord here).

If you want to add it to your calendar RSVP here.

What this session is:
  • It's going to be a freeform open discussion and collaboration
  • Together we'll explore what a business model canvas might be for an indie consultant
  • We'll each sketch out our own version
  • Show & tell
Why you should join:
  • Firstly - I hope this session will help you understand your own indie consulting business more clearly
  • Secondly - it'll offer a look at other people's indie consulting practice to share notes and insights
It might look something like this. Or maybe something like this? I haven't decided yet. Hopefully we'll figure it out together!

Note: this will happen in figma so if you haven't I encourage you to play around with it a little beforehand. It's free and you can use it in your browser.

This session is specifically intended for indie consultants but weirdos of all stripes are welcome.

Much love

Tom
 
#37
July 16, 2020
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Thinking in Public - Tomorrow 1pm ET in my Cozy Discord Space

Programming: Hey - it's me: Tom Critchlow. This tinyletter is a more intimate space than my blog - on a more relaxed schedule. I write about indie strategy consulting and blogging. I always read the replies, so email me to say hi!

This Tinyletter has always felt more intimate than my blog posts - kind of like a B-side to the the polished hits on my blog (jk - hits?!). These notes feel somehow more cozy - like inviting my audience into a little fireside chat.

Writing a blog post invites any kind of public scrutiny - it's *designed* to be public. Whereas the Tinyletter has some stance of - *you kinda need to be on the list to read these*. As I mull this tension between public and cozy I realized there's room for a new space - a cozy chat space:

Let's unpack this:
  • Fast & public: This is Twitter - functioning like a public commons
  • Slow & public: This is my Blog - open to all, on a measured pace
  • Slow & cozy: This is my Tinyletter - a measured pace and a cozy intimate stance
  • Fast & cozy: This is a new space: Discord - a place for more intimate real-time experiences
 

Come Join my Discord

Discord is exploding in my circles - rapidly becoming the go-to tool for the coming wave of fragmented social spaces. Discord is quickly replacing Slack for this use case - and in fact Stewart Butterfield (Slack's CEO) said this is by design (behind Stratechery paywall):

Something interesting for me - because Discord spaces are free there are fewer power dynamics and I can feel free to make "my" discord space without imposing my power (and: importantly you create a Discord account, not a tomcritchlow discord account - so I can't read your DMs. A crucial distinction vs Slack).

So come join! Click this link to join the Discord space.

(By the way you can preview the Discord here)
 

Using my Discord Space for Salon-Style Chats

One of the great features of Discord is the voice-channels where you can "drop-in" for audio chats. This interaction feels more fluid and casual than a zoom webinar. I've got two voice channels right now - #salons and #co-working.

#salons is going to be where I host scheduled sessions - on all kinds of things. Watch this space for more info.

#co-working is going to be where we can just hang and chat when we want.

Got a suggestion for a small talk? Want to pre-test an idea before it becomes a conference talk or blog post? Ping me and we'll set up a salon for it.

Salon #1 - Thinking in Public tomorrow @ 1pm ET

The first salon is going to be tomorrow (Tuesday) 1pm ET in the discord space! We're gonna fire up a figma file, gather round and chat. It's going to be fun and weird and experimental. Hopefully it'll be useful for all kinds of folks who are thinking about how and why to think in public:

  • Hopefully it'll be useful for any agency / consultant types who are wrestling with "content marketing" and need a better way through
  • Hopefully it'll be useful for bloggers / writers who are wrestling with finding an audience and figuring out their style.
There's no eventbrite or reminder - just show up in the discord at 1pm tomorrow. If you want a calendar reminder reply with your email address.
 

More Links

This email is getting long so I'll keep these brief.

From me:
  • Quotebacks is finally ready for Firefox! If you've been waiting dive in and play around.
  • I wrote the next post in the quarantined independent blogchain: can calendly unbundle NYC? (where I also share some stats about where my client work has come from over the last 6 years)
From others:
  • Paul Millerd wrote a wonderful meditation about why you should be a creator online: We Need 100x More Creators Online
  • Aaron Z Lewis wrote a magnificent piece: The Garden of Forking Memes: How Digital Media Distorts Our Sense of Time
  • Toby Shorin wrote an also-magnificent *reply* to Aaron's piece: re: garden of forking memes
  • Sean Blanda wrote a really insightful exploration: Our remote work future is going to suck
Some great blog posts recently. Let's keep it up!

Much love - I hope you'll come join my discord, whether to chat or just to lurk and join the salons. Both are equally allowed!

Tom
#36
July 12, 2020
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Yes! And... Part 4: Navigating Status & Power

Quick reminder: I'm Tom Critchlow and this is my email newsletter where I talk about independent strategy consulting, blogging and more.

Back in December one of my posts hit the homepage of Hacker News: Yes! And... How to be effective in the theatre of work. That single post drove more than half of the subscribers on this email list (hi! welcome!).

Since then I've continued the series. Catch up here:
  1. How to be effective in the theatre of work
  2. Optimism as an Operating System
  3. Blocking & Unblocking Clients
And yesterday I just published the fourth part of the series:
 

Navigating Power & Status: How to get things done inside organizations by understanding power potholes and status switching

The archetype of "consultant" is usually one of the intellectual - someone who walks into an organization and *solves problems by being smart*. In my own work however, and increasingly in my writing, I'm discovering that this archetype is flawed and counterproductive.

Instead of problem solving - we should strive for capacity building: creating new capabilities with clients. This stance is by default more collaborative, longer term and more foundational.

And - it requires being able to actually get things done!

But... Anyone who's tried to get things done inside an organization knows that undercurrents of power, status and influence dictate who is able to get things done, which teams have favor, buy-in and more.

So - that's what this piece is all about. It's about navigating power & status inside a client's organization. Sensemaking, listening, watching and ultimately engaging with status transactions across the org. 

It's long but I hope it's useful for you:

Read it here: Yes! And... part 4: Navigating Power & Status

This book project is picking up momentum. I just redesigned the book outline on my site (including listing all the unwritten drafts!) so if you're looking for the best place to "see" the book start here.

Maybe next email I'll be ready to walk through some of the publishing options on the table......

With love

Tom
#35
June 24, 2020
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Roxy's First Blog Post

Hey there. Reminder: I'm Tom Critchlow and this is my tinyletter where I talk about blogging, independent consulting, media strategy and a bunch of other stuff.

My interests right now consist mostly of: parenting, blogging & consulting - and this email is about all three! But first, the thing I'm most proud of - Roxy's first blog post

Roxy's First Blog Post

As you can imagine there's a lot of talk about blogging in our household - and my daughter (4) is old enough to over-hear and join in with those conversations. As such - she wanted to write her own blog post! We used a combination of typing (she wrote "Roxy's first blog post" all by herself!), Google Docs speech-to-text and embedded audio files.

Check it out: disaster!

Roxy wanting her own blog post is one small example of "visible knowledge work". Because everyone is working from home now the lines between work / family / parenting / housework are melting away. Previously invisible knowledge work is now visible and legible for the whole family. I wrote about that for the latest Yak Collective report: The New Old Home.
 

Quotebacks - A tool to quote the web

Over the past few months I've been working with Toby Shorin to build a small tool for bloggers. Toby and I are interested in exploring new models of networked writing and increasing the dialogue between bloggers.

It's a Chrome extension (Firefox coming soon!) that allows you to grab snippets of text from around the web and embed them on your site just like an embedded tweet. They look like this:
Read more about the extension in my launch post (or just download the extension directly).

Let me know what you think!
 

Executive Sparring & "Tenure" for Indie Consultants


If you're an indie consultant you really should be subscribed to Venkatesh's newsletter Art of Gig. It's one of the few meaningful sources of knowledge for indie consultants out there. So I was honored to get to write a guest post for Art of Gig - all about "tenure" for indie consultants and how the "executive sparring" mode of consulting fits in.

Read it here: sparring as tenure

I'm proud of how this piece came out - and I tease a few concepts that I'm going to be writing more about - namely the compound interest effect of thinking in public and how it's crucial for indie consultants.

--

Finally - these are troubled times, but hopefully times of change. My voice is a small one but I'll state it explicitly: Black Lives Matter. A few things I've found:
  • This actblue link to donate to a bunch of bailfunds at once.
  • This link of supporting black leaders running for office
  • This thread on research-based solutions to stop police violence
--

Much love,
Tom


 
#34
June 9, 2020
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The Quarantined Independent & Improv Consulting

Hey, I haven't sent one of these emails in a while so let me re-introduce myself. I'm Tom Critchlow, a blogger, independent consultant and general internet trickster.

My family is doing OK in lockdown - we're healthy and coping. I think it's been hardest on the kids though...
My daughter giving side-eye while celebrating her 4th birthday via a Zoom party
I hope you and the ones you love are coping.

My last email went out in October 2019 (a.k.a when we were *younger*)​ so there's lots to cover. Let's dive in:
 

The Yes! And... Papers

As many of you know I've been writing a book over the past 18-months or so: The Strategic Independent - theory and practice for independent consultants.

Pre-pandemic I started a new chapter in the book that I was affectionately calling the Yes! And... papers. It's a series of writings around the idea of improv acting and how it relates to consulting work:
  1. Chapter 1 - How to be effective in the theatre of work
  2. Chapter 2 - Optimism as an operating system
  3. Chapter 3 - Blocking and unblocking clients
I hope you'll queue them up and read them - I think they're some of my best writing (and I was lucky enough to have chapter 1 at the top of Hacker News for a few days - which is where a lot of my new subscribers came from! hi! 👋).

There are two more chapters in this series waiting to be finished - but I've been interrupted twice now. Firstly by the birth of my son in December (hello Indigo! 👶) and then by a global pandemic.... Which leads me to:
 

Consulting "After Peacetime"

I put my Yes! And... papers on hold and... for a while didn't write anything. Until I realized that the mission for my writing about strategy consulting work for independents is to help independents in their consulting work. And indies are suffering right now.

So - I dusted off a new blogchain and fired up some faster, looser, more urgent writing around consulting through these weird times. The Quarantined Independent - so far there are 4 posts:
  1. Introducing the Quarantined Independent blogchain
  2. After Peacetime
  3. Collective Narratives & Sensemaking in Uncertainty
  4. The challenges of remote consulting (⚡ this one is the most interesting I think...)
These posts are questions more than answers - it's me feeling my way through ~all this~ and trying to navigate it somehow gracefully. I hope this writing helps - and I welcome comments, feedback and ideas.
 

Domestic Cozy Blogging

I've realized that I've become quite the crazy person. Blogging has become a core part of my identity - and fiddling with my blog has become a hobby and long-term interest for me. This.... will likely be no surprise to those of you who are close to me but it took me a while to realize.

When the pandemic started - I retreated into the domestic cozy world of fiddling with my blog and doing some internet trickery (honestly what I do is not coding, I prefer the word trickery). Some things:
  • A proposal for a library.json bookshelf format for bloggers (📚this one was very widely shared - watch out for the followup soon!)
  • New blogging 3: Blog Patterns (where I install site search on Jekyll and reformat how side notes work)
  • Tiddlyblink on Glitch (know about Tiddlywiki? even though it's 15 years old it might end up out-pacing Roam! lots of fun experimentation here right now)
Oh - and there's a totally top secret new project I've been working on specifically for bloggers. Want early access? Ping me.
 

Public Work

I'm usually pretty cagey about the clients I work with - high level strategic work helping clients build new capabilities is often slightly uncomfortable for the client and I tend to bias towards being discreet. I don't have case studies on my website for example.

But recently I've had two client projects bleed out into public (is this a consequence of the pandemic? unclear) so I thought I'd share:
  1. I'm working with HomeAdvisor on a strategic re-factoring and re-investment in SEO & content. As part of that I'm leading recruitment for a VP SEO based in Denver/NYC. I wrote up why it's so challenging to hire a VP-level SEO over on LinkedIn.
  2. I'm working with Google's Area 120 team on a new project called Keen, advising on product strategy and growth - it's an early product aimed at helping you expand your interests. Think of it like are.na with a personalized recommendation feed for every channel. I wrote up how I'm using it to follow some blogging trends.
Attaching my personal identity to consulting work in public is an odd experience, and likely one I'll blog about at some point but both projects made sense to blur the boundaries so here we are. Hope it gives a peek into my consulting work.

Music

I've been finding solace in these uncertain and often confusing and stressful times in some lovely (new to me) African music. Some favourites:

Nomalanga - Caiphus Semenya
Not yet Uhuru - Letta Mbulu

And - this live song from Valerie June is very life affirming.

I hope they can bring you a small amount of hope in these times.

--

Forgive the lengthy email - it's been too long. I'm going to get back on a roughly ~monthly schedule going forward.

Be well, stay safe, look after each other.

Write back? How are you?

Much love,
Tom
#33
May 5, 2020
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Five Years on the Road - On Blogging and Gratitude

Hey it's me, Tom Critchlow, your friendly neighborhood consultant/blogger/weirdo. This list has grown a fair amount since I last wrote to you all so as a reminder: you probably signed up at tomcritchlow.com and this newsletter covers: independent consulting, art/tech crossovers, media design and networked writing. Thanks for being here.

Five years ago I quit my job and went independent. The best metaphor I've found for being independent is like being on a road trip:

It's really two emotions wrapped tightly together - on the one hand the freedom of driving where you want with the windows down and the music blasting, while at the same time being untethered without a home or permanent shelter.

At times it can be dislocating and disorientating but mostly I've had an incredibly positive experience and I want to.... get a little squishy and emotional for a moment. Seriously - *thank you*. I literally would have not been able to make this journey happen without the friends, bloggers and networks I'm a part of. That means all of you on this newsletter. Thank you thank you.

For all of 2019 I've basically had one main retained client - and it came from my blog, re-kindled THREE YEARS AGO when I wrote my TWO years on the road post:


The power of networked writing... of networks.... of blogging. It's funny how things go.

I've talked about the power of small-b blogging before but I don't think people properly understand quite how *small* I'm talking. It's outrageous that my blog has such a meaningful impact on my life - clients, friends, connections - when it's this small:


If you're unsure about the leap into blogging, into consulting, into networked writing then consider this a kick in the ass - if I can carve out a small slice of living from this meager network then you can too!

Head on over to my blog post: 5 years on the road for the full recap, revenue charts and so on but mostly I wanted to give a big fat thank you to every single one of you.

I'd love to hear from you - hit reply and tell me what you're up to!

Thanks a million. Love you all.

Tom

PS - here's a few other posts I wrote since my last newsletter: occult ads and understanding marketing realities. The notion of brands as unknowable hyperobjects is top of mind right now. Ping me if you have thoughts or want to chat.
 
#32
October 23, 2019
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Portals, Podcasts & Punk

Hello everyone,

Just a quick reminder - I'm Tom Critchlow. A strategy consultant, blogger, art/tech weirdo and lover of the color green. You probably signed up for this on tomcritchlow.com

A few updates on what's going on - some interesting links and more. Let's dive in.

Portals

My latest writing in The Strategic Independent series is all about workshops - but actually it's not about the kind of workshop you're probably familiar with. Instead it's about creating a portal inside a client's organiztion so that you can bridge the outside/inside problem of consulting.

Workshops as portals - and how to create clarity in consulting work

I've had some great responses to this post so I hope you enjoy it. And - if you're digging the consulting writing I do I've collected all the posts into an Are.na channel here: the strategic independent.
 

Podcasts

Do you know Mark Pollard and his podcast Sweathead? You should! Mark is one of the best podcast interviewers around - I especially love how every episode just launches into it. Usually you're hearing the conversation in under 10 seconds. Contrast that to so many podcasts with the long meandering intro, the music, the about, the, the, the.... Ugh. Just get to it. Mark doesn't mess around. Love it.

Mark was kind enough to invite me on the show and we talk about bouncing around, making leaps, finding work and how confusing being an independent consultant can be sometimes.

Ok - but if you like podcasts you should also check out The Tension from my good friend Howard. They're playful, 4-5min episodes that are fun, weird and make you think.
 

Punk

Did you catch my post from a little while back on Blogpunk? This idea of keeping it weird and letting your personality shine through in your writing continues to excite and interest me. This is another little doodle from a recent chat with my friend Howard (the same from the podcast above):

What is this image all about? It's a 2x2 on blog vs book / fiction vs non-fiction. It maps the spectrum of writing choices you have (loosely, weirdly). I'll explain later in a post soon.

I hope you're finding ways to let your blogging be a little punk?

To that end - two things that I'm doing that are a little weird but very fun:

Little Futures is three issues in:
  1. Business Time - every company has a clock
  2. Learning - every company needs to learn
  3. Language - language is a problem
My blogchain with Brendan on Networked Communities is a few posts in and getting exciting:
  1. Brendan: weaving a public web
  2. Tom: blogging as a social act
  3. Brendan: sidewalk spaces & positive gatekeeping
I've got a very exciting fourth post to add to this blogchain and.... it's going to be very weird! It's not quite ready to share yet but it might introduce a new way to hang out together online....
 

Links

Few more interesting things I saw recently:

A zine all about sharing your work:

In my opinion writing is a public act, we must learn (even the most introverted of us) to share our work with a readership. See our work as worth sharing, our voices as worth hearing. It doesn't have to be a huge public gesture; it could be 10 copies among friends. Share.

This super weird essay on the computer mouse (best on desktop)

a scrolling lecture on the computer mouse

Counting the future - a weird thing that's hard to describe but worth the click.....

Counting the Future is a visual history of prediction; a collection of attempts to predict the future from data. It focuses specifically on the diagrammatic nature of statistical prediction and puts predictive diagrams in relation with each other through time, across disciplines and domains. The resulting epic meta-diagram aims to provide a new way to access the history of prediction: a subjective and incomplete map which invites multiple readings.

A sewists statement -from Nozlee Samadzadeh an artist's statement about sewing, nothing and everything:

It just turns out that MAYBE my artistic practice isn’t simply the production of clothing, it’s a long-term performance piece about labor that happens to produce clothing as artifacts of the performance. I’m kidding—kind of—

That's all I've got for now.

The next post in my strategy writing is all about "the jigsaw of independence" - it's about managing time, managing energy and staying sane as an independent. Ping me if you have thoughts or ideas here.

Much love.
Tom

#31
September 26, 2019
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Why I'm launching a new research/consulting studio called Little Futures

TL;DR - Hi, I'm Tom Critchlow a strategy consultant. I do media design consulting and blog about being an indie consultant. But today I'm launching a new venture: Little Futures - a research/consultancy studio in partnership with Brian Dell. The first output is a new weekly newsletter. Sign up here. Keep reading for the why.
I've written before about the tensions of branding your consulting practice. In my post (from 2016!) I explain why I didn't launch a brand for my consulting practice:
Personal branding, especially for (gasp!) a marketing consultant is terrifying. How do you escape being that arrogant person while still appearing professional and capable of well-paid work? How do I avoid putting a ferrari or a photo of me skydiving on my about page?! (The answer it turns out is remarkably easy - you just don’t put a skydiving or ferrari photo on the page).
But - that was two years ago and my thinking has evolved. I've evolved. I've grown. I'm still growing...

The truth is that I'm a little more comfortable with the consulting life right now. I've been doing this almost five years and for the last two years I've worked almost exclusively with media organizations.

But complacency will kill you, and I'm keen to keep growing and evolving.

(aside: for a great analysis of the growth stages for an indie consultant check out this post from Venkatesh's project Art of Gig: the gigwork hierarchy of needs)

The reality is that our identities are actually fractured illusions anyway - so the right move is not to re-brand my consulting work (tomcritchlow consulting is still sticking around as is) but rather I'm launching a new venture - a fork in the identity portfolio to deliberately venture into new kinds of work and new industries.

The idea is to try and get new kinds of work, not just more of the same. To attempt a few sectoral boundary crossings:

Enter Little Futures

So I'm launching a new venture. A research & consultancy studio called Little Futures. It's a partnership and collaboration with Brian Dell - a close friend and one of the sharpest thinkers I know.

Although Brian isn't a *very online* person like I am you've already been impacted by his thinking because almost everything I write goes through a discussion phase between the two of us. Brian has helped me understand markets, startups and people better than I could have on my own.

Both Brian and I have worked across media, brand, startups, consulting, strategy and research and we're excited to combine this into a new thing. What shape that thing takes is still amorphous but the first output is a weekly email that will showcase our thinking and perspective. Sign up here.

As Brian said - "if your job is change, Little Futures might be the best way to get to the Big Future."

The first email went out this morning on the subject of Business Time:

Little Futures 01 - Business Time


So I hope you'll join us and come along for the journey.

(*Note I had planned for this Tinyletter to be sent before the first Little Futures email went out but it turns out .club domains trip all kinds of interesting spam filters*)

Links

A few other goings on:
  • I started a blogchain with Brendan Schlagel on "Networked Communities". We're three posts in and I'm really enjoying the conversation. Start at the beginning.
  • As a relatively new dad (soon to be dad of two!) this piece from Craig Mod destroyed me. "my father taught me not one single thing"
  • I've really enjoyed following James Greig over the years - he's written some great things about independence but his most recent one is about going back to a job and it's a great little meditation: The unexpected pleasures of returning to employment from freelance life
Much love.

Tom
 
#30
September 9, 2019
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Finding space for creative projects (and Erin's Kickstarter launch!)

*Hey, it's me Tom Critchlow. Normally you can find me writing about digital media, indie consulting and so on but today's post is more personal. Back to regularly scheduled programming next tinyletter.*

My partner in crime Erin has been spending the last three years writing and illustrating a picture book for kids.

When our daughter was born the first instinct is just to hang on - to try and salvage some normalcy out of the chaos of parenting. But as Roxy got older you start to realize that they’ll grow into little humans, curious little humans. And that they learn mostly by watching, not through the “teaching” or “parenting” you do.

So we resolved to close the gap between who we were and who we wanted Roxy to see us as. In other words to put work into those things that mattered to us and to pursue the goals and projects that would align with who we wanted to be.

This might sound mushy but… Erin and I have carved out space for projects we really want to pursue. It's been a driving force for writing my book (The Strategic Independent) - my writing is coming but it’s further behind - and Erin’s spent the last 3 years dedicating her art practice to writing and illustrating a picture book for kids. It’s beautiful!

The Kickstarter just launched:

It would mean a lot to me if you could back the project, share it or just give a virtual high five. If you don't have kids yourself Erin's aiming to ship in time for the holidays so perfect for gifting!

How would you change the things you spend time on if your child was watching?

All my love
Tom
 
#29
July 29, 2019
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Help guide and shape my book by annotating the outline!

Hey friends!

For subscribers new and old - a reminder that I'm writing a book. Working title: The Strategic Independent.

For the past year at tomcritchlow.com I've been steadily writing longer and longer "chapter-like" pieces to try and write the book in public and flesh out my ideas. And I noticed that I've got about 30,000 words written on the blog (does that count as roughly 50%? is a book 60k words? sure!).

So I thought it would be fun to pause and take stock of the writing so far. Is it working? What holes in the book outline still need to be filled in?

I'd love your help!

I posted up the full book outline here:

https://tomcritchlow.com/2019/07/12/annotate-the-outline/

Please dive in with comments, suggestions and ideas for how to make this book something you'd like to read!

What struggles have you had in independent work? What ideas have you not seen explored elsewhere?

I'm using the tool Hypothes.is to power the annotations (think in-line comments just like Google Docs). It's a little clunky (especially on mobile!) but I like the concept and power of in-line comments on the web and Hypothesis are a non-profit (vs the adtech nightmare of Disqus). For now disqus is at the bottom if you feel safer there that's totally fine. Or twitter. Or just reply to the email right now!

I'd love to hear from you.

Thanks

Tom xo
 
#28
July 11, 2019
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The biggest mistake I've made in my consulting work in the past two years

I've been out on my own for almost 5 years now. The first two years or so of consulting were spent finding my feet. The basics of figuring out what my approach was, how to talk about it, how to find clients and so on.

But more recently I've spent the last few years trying to deepen my understanding of *how to be an independent consultant*.

In the course of this introspection and research I uncovered a critical flaw in the way I approach consulting. It's all about frameworks. They're highly effective tools but for too long I've been trying to bring off-the-shelf frameworks to client work and failing.

Instead I realized that I need to roll my own..

Here's my 5,000 word exploration of my own failures, theory of frameworks and 4 case studies from my own work:

How (and why) to roll your own frameworks in consulting engagements

For those new to this tinyletter (hi! thanks for subscribing!) this is part of an ongoing series of writings that will hopefully turn into a book-ish object later this year, working title: The Strategic Independent.

What do you think? I'd love to hear your experience with consulting, independent work, frameworks, co-creating mental models with clients and doodling. Leave a comment on the post or hit reply here!

(Aside: if you identify as an independent consultant you should really check out Art of Gig - it's a newsletter from Venkatesh Rao of Ribbonfarm fame all about consulting and it's delightful. $5 / month and worth every penny.)

In other (blog) news

Here's what else has been going on in the feeds:
  • Blogpunk - the idea that for most blogging, personality is the key ingredient. If you subscribe to the small-b blogging ideology then 
  • I've been extending my self-hosted wiki with some new tactics and scripts: planting new varietals in my digital garden (all about using screenotate to structure my screenshots) and using bookmarklets to script my static site (all about quickly generating markdown code with a bookmarklet).

What are you blogging these days?

Much love,

Tom

#27
June 26, 2019
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Independent Consulting (links of interest!)

Hello there to my little corner of the republic of newsletters!

Firstly - welcome to all of the new subscribers. Quick background and refresher for those who are new:

I'm Tom Critchlow, independent strategy consultant in Brooklyn, NY. This newsletter is mostly filled with musings on media, consulting, digital art and whatever else is interesting to me right now. I do a bunch of blogging over here: https://tomcritchlow.com/ and that's probably where you signed up. Welcome! (and of course, there's an unsubscribe button at the bottom).

This newsletter has no real theme or direction but there's just been an accumulation of *things* that I feel add up to a "thing worth sharing" but it's mostly just a list of links I've enjoyed recently...

Consulting Fiction - novels about consulting are pretty few and far between in my experience so it was a delight to stumble across Venkatesh Rao's old story The Art of Gig. This fast-paced adventure starts with a 2x2 and quickly dives head first into Structured Conversation Operations™.

This prompted me to make a (short) list of great works of fiction that appeal to the life of a consultant: stories about consultants.

Indie Consulting - what is indie consulting anyway? Venkatesh (again!) posted a deeply interesting and navel-gazing speculation on some different types of indie consulting in a twitter thread here. (Can you locate yourself on the 2x2?)

Oh - and Venkatesh just started a $5 / month newsletter for indie consultants specifically, called - you guessed it - the art of gig. You should subscribe right here - the first email goes out this week and it should be excellent.

Diagrams & Mental Models - a coffee meeting with a friend the other day blew my mind when he showed me a *new type of diagram*. Why is diagramming and doodling so powerful for consultants? I think it's because the unit of work is the mental model. Creating, challenging, clarifying mental models is the essence of a consultant (I think). Anyway - I've got a whole blog post brewing here but I'd love to hear from you: what diagrams and visualizations are your go-tos? Who have you learned from here? I posted a thread on Twitter and there's already some great responses. Add yours too!

Narrative & Consulting - Narrative arc is important to any consulting relationship. Controlling how the organization sees you and your work is very important and can make or break a contract renewing. My friend Arnold posted a really fascinating post managing the narrative arc where he links to a podcast from A16Z with Brian Koppelman. They explore the concept of "Showrunner" which was a new one to me but really feels like a great analogy to CMO (or consultant) within an organization. Have a listen and read Arnold's post and let me know how you think about managing the narrative arc in your work...

See also: I really *love* seeing independent consultants actually show their work so this post from buddy Elan Miller was wonderful to see. Real work! Real slides! Real thinking! Love it. Narrative-drive product development.

Book writing! - I've been writing about independent consulting work a bunch over the past 6 months and I'm starting to explore turning that writing into a book. Working title: The Strategic Independent. After my last post (called the strategic independent) and the positive reactions to it - I've started to consider finding an agent/publisher for this book. I've got ~20k words posted on my blog and another ~20k in draft so I think I have enough to talk about with an agent/publisher! Any intros or suggestions send em my way please.

Also - if you enjoyed my last post I recorded a podcast all about that post where I explain some of the thinking in more detail (and hilariously try and describe the diagrams with the podcast host!). Listen to the episode here on the Ditching Hourly podcast.

The art-business-consulting-made - This is an aside but as well as indie consulting I run an art business with my partner called Fiercely Curious and we have an art show in Manhattan this week May 1 - 5. More details here. Entry is $15 or something but I have VIP passes so hit me up if you wanna go! Erin does all of the curation for the show and I think it looks absolutely amazing.

Thanks for reading! As always - hit reply with anything on your mind. I reply to everything.

Tom
#26
April 29, 2019
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The Strategic Independent - the thesis for my book

Writing a book is hard! I mean, I'm sure this is not news for anyone who's tried... but until you *try* it's hard to understand the demons you have to wrestle to do the work.

I've been on-and-off-and-on-again writing a book since the beginning of last year but only in the past 3 months have I carved out a deliberate writing schedule and cadence for writing to really move this thing forward and start putting shape against it.

Originally - the premise for the book was "a book not about consulting but about being a consultant" - mixing theory and practice of how to do consulting but also the inner game of consulting (how it feels etc).

That's still mostly what the book is about but the word "consultant" kept bothering me - it is a word I identify strongly with (see: 4000 words in my recent post I, Consultant?). But not everyone identifies with the word consultant...

Instead - the phrase "The Strategic Independent" kept floating around my head. That's who I'm writing this book for. But what is a "strategic independent" anyway? I had a pretty good idea in my own head so I wrote it down...

The Strategic Independent

This post ended up at 4,500 words and includes a bunch of diagrams too!

The post itself is somewhere between a manifesto / philosophy / practical guide for doing independent work that is: well paid, interesting & effective.

But! The post is also really the foundational thesis and definition of audience for my book!

Anyway - hopefully you'll enjoy this one. I think it's a fun mixture of theory and concrete advice (with some personal stories thrown in too).

If you want to see the book outline as it starts to take shape I've been collecting and organizing here:

https://tomcritchlow.com/strategy/

And I've got a clear sense of at least another 3-4 posts. So watch this space.

As always - feedback is the lifeblood of writing so any ideas, comments, suggestions are more than welcome. Just hit reply and lemme know what you think!

Love

Tom xo
 
#25
April 3, 2019
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How do you find work as an independent?

It's probably the number one concern for independents - how do you find work? And once you start finding enough work to pay the bills - how do you find work that you are actually excited about?

There are many ways to do this but for my own work they hinge on the notion of networks. How do you build these networks? Where do leads come from? Is it all random?

All of this is what I address in my latest post Strange Attraction:


Yes, I might have gone off the deep end with the analogies (chaos theory, seagulls etc) but hopefully this helps make the piece enjoyable.

As I mention in the piece though - there are a million different ways to think about generating leads because there are a million different types of independent consulting work (and consultants!).

What's your experience building leads and finding clients? Hit the reply button!

Much love

Tx
 
#24
March 11, 2019
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The question of self-labeling as an independent is strangely vulnerable...

"The question of self-labeling as an independent is strangely vulnerable"...

Those aren't my words - Carson Mobley said them in response to my latest blog post but they really sum up the position well. How do you self-label as an independent? And why do the choices you make matter so much inside your own head?

Of course making up labels and language to describe yourself and the work you do matters to others - and it matters for clients and positioning etc. Of course. But it's in the inner game that is the strange one.

The headspace of trying to "live-up" to the labels that you yourself invented. The process of trying to "justify' their existence. It's an odd game. And sometimes a lonely one as an independent.

But there's hope - for one, once you realize that it's all poetry you can have fun with it! And you can invent multiple labels and identities for a variety of situations. Or you can choose a label only to shed it like a snake skin 12 months later. It's up to you.

All of that said - this inner game of labels matters! In particular, I've found in my own work that using a label like "consultant" or making a "consulting practice" helps relieve the pressure of invoicing and charging for my work (still to this day - every time I send an invoice I want to throw up).

Anyway - this piece is slightly dense and... I'm sorry-ish(?) for that but also I enjoy the depth and variety of rabbit holes that you might choose to follow:

I, consultant? - The struggle to define who you are as an independent and the promise of charging more for your work

Thank-you of course to Toby Shorin of Subpixel Space who helped edit and write this piece and provides some in-line commentary on the post. (and if you're not familiar with Toby's writing please you should dive in immediately).

What labels do you use? What struggles have you found in using them? Would love to hear your stories! Reply to the email or leave a comment on the disqus.

Thanks!

Tom xoxo
#23
February 26, 2019
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Open sourcing my drafts folder (and making a new wiki on my blog)

Hey bloggernauts!

It's been about four months since the last email - so I suppose I owe you both an apology and a celebration. Sorry you haven't heard from me - and/but yay for not taking up space in your inbox.

Client work has been steady and busy for the last 4 months so that's mostly what I've been doing. A little book writing as well - but oh my trying to write a book is hard work. Not so much the actual writing but the weight of carrying a (metaphysical) book on your shoulders all the time. It's a psychic load, that's for sure.

Anyway - this email brings us back to blogging. Or, more accurately networked writing. I've been very curious about the ways in which "internet-writing" is new, different and useful. So there's two things I want to draw you to:

Web-annotations

I wrote a post exploring the UX of web-annotations. Except - the title is a little misleading. UX is one (albeit important) part of the puzzle but more broadly annotations are an interesting and likely *new* part of the web. There's a new proposed W3C standards thing coming that I don't claim to fully understand but it involves annotations. But this piece breaks down some of the various solutions for allowing in-line comments on your own blog.

Be sure to stick around for the updates at the bottom of the post where I post what I think is a nice clean "standard" javascript script that anyone can use to embed annotations using Hypothesis.

Secondly...

I built a personal wiki

For some time I've been playing with three "modes" of information exchange on the web:

Streams - This is the fast-twitch flow that I personally use Twitter for. Plenty saturated at the moment.

Campfires - This is the blog (and more broadly the blogosphere that I read and engage with). Room to grow here but generally I’m satisfied.

Gardens - This is where there’s the widest gap for me personally. No place to store and evolve deeper longer-term thinking. Many of my friends have gravitated to Are.na but I just can’t get it to work for me.

So I went on to build my own solution using only text files and folders and published on the web using Jekyll/Github pages. There's a full writeup here:

Building a digital garden.

But - here's the semi-secret announcement for those of you on the email list, one of the folders of my wiki is my entire blog post drafts folder:


Be gentle, of course, these are my butterflies pre-flight! Fragile and delicate and almost non-existent in some cases. But maybe there's some that catch your eye? Perhaps encouragement is all that's needed to push some of them over the edge?

--

Because all of the above is about me I thought I'd throw in a few links I've enjoyed recently too:

- Blogging to exhale by Daniel Gray (a wonderful pairing to seeking inspiration? by Derek Sivers)

- The city is my homescreen by Dan Hill

- Nike x Architecture x Disaster Capitalism (032c)

--

That's all for now from this corner of the republic of newsletters. As always - hit reply with feedback, ideas or just to chat.

Tom


 
#22
February 17, 2019
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Ways of Seeing - a longer post (with a behind the scenes peek)

Hello again! Apologies for two emails in two weeks - way above my normal erratic email frequency.

As mentioned in the last email - I'm at the early stages of writing a book. It's got a working title I'm too scared to share but the subtitle is: The theory and practice of independent consulting.

Hopefully this resonates - I'm trying to amass a group of folks charting their own unique paths through independent / freelance / founder / self-employed life and provide a resource for those - especially those who dive into client environments.

My latest post is looking at that tension directly - how do you work in an environment where the culture is foreign? (and we know that their culture is going to eat your strategy for breakfast!) The post takes the central premise that you can learn a lot from art and ethnography in understanding culture and cultures.

(There's also the usual snark).

This post is 3,700 words and tries out a new style of writing but hopefully you'll enjoy it:

https://tomcritchlow.com/2018/10/29/ways-of-seeing/

As always - I'm forever grateful for those who contributed and reviewed drafts behind the scenes. I thought I'd show you a few of those and how they played out:

The first kind of feedback I love is inspiration for ideas and links I've not seen. For example the little grey book is a truly wonderful text and an addition from Robin:

The second kind of feedback I love is friends helping reign me in or add counters to my points, this really helps tighten up the "wild" sections and make my whole piece stronger and better. For example here's Thomas keeping me in check:

The third kind of feedback I love is where I'm forced to get off my theory and dive into practice. This comment from Sean and Susie directly helped me add a section talking about an actual client case study - this helps people connect to the ideas and also just makes the overall piece more interesting:

And finally - here's a really insightful remark from my friend Toby that cuts to the real "why" of the piece to help make it stronger. This comment forced me re-work the piece from start to finish to add a theme beyond "just" ways of seeing. Thank you Toby!

Anyway - I always enjoy this kind of insider baseball and I hope you do too. And of course hello and thank you to all who contributed thoughtful edits and comments!

Another thing you might notice about this blog post is the new format and layout. I've adopted a very slightly modified tufte css style:

This design has stronger readability for longer-form writing and hopefully allows me to start collecting all of this stuff in once place. It also lets me do these nifty sidenotes which I think are great:

Anyway.

I start a new client gig tomorrow so I can only imagine that you won't get another one of these emails for a little bit! Hopefully there's enough to chew on here. You can see that I've been thinking about this stuff closely for a long time!

As always - just because it's published the feedback process is not done - any and all feedback and comments are greatly welcomed. Hit the reply button!

Much love.

Tom
 
#21
October 28, 2018
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