People and Blogs: Tom Critchlow

Let's start from the basics: can you introduce yourself?

Hey I’m Tom Critchlow. I grew up in the North of England and moved to NYC ~15 years ago. I live in Brooklyn with my partner and two kids (9 and 5). They’re like electric smudges. Full of crackling potential and never quite where you expect them to be.

I’m best known I think for being an independent consultant working in digital media - I worked for myself for 10 years and blogged my way through that whole journey. I wrote an annual recap for 9 years in my series on the road and I wrote a whole book about the practice of sustainable independent consulting which I serialized on my blog: The Strategic Independent.

About a year ago I took a full time role which was a big narrative violation with my identity as an independent consultant but actually I’m also a deep nerd about organizational design and management theory so this has been a fun change of pace from being self employed and a chance to flex some different muscles.

My favorite color is Green.

What's the story behind your blog?

I’ve been writing online personally and professionally forever. As a teenager I wrote short stories and poetry online at Elfwood. Then in my early 20s, as a semi-professional poker player I’d post on the Two Plus Two poker forums. When I started working in SEO and digital media in the early ‘00s it was just kind of the done thing to blog - there was a culture of open sharing. We’d blog about stuff we were discovering, how Google worked, conferences we’d been to and so on.

But, after bouncing around various platforms like Tumblr, Medium and Svbtle, I eventually committed to tomcritchlow.com somewhere around 2015. That was the first year of going independent and so everything really started there. In 2016 I almost launched a brand for my consulting work but backed out and instead committed to blending my personal and professional writing on my blog. In hindsight that was a pivotal moment when online writing started to really become important and a part of my identity.

I’ve always gravitated towards loose, iterative, messy writing. Some of my most popular writing has been building a digital garden, small b blogging and writing, riffs and relationships.

Among my friends I’ve long been “the blogging guy” but it’s taken me a surprisingly long time to realize exactly *why* blogging is so important to me - it’s because it’s a form of creative expression that finds other people. Writing on the internet has always for me been in service of finding creative connections with others and I wish more people had an outlet for being themselves and finding other people.

What does your creative process look like when it comes to blogging?

No kind of routine or process has ever worked for me to write with any consistency - instead all of my writing either comes out of a random flash of inspiration or overdosing on coffee. Often both.

That said - maintaining a long list of drafts, post title ideas and quotes is kind of the raw materials from which inspiration comes. So I try and note down headlines, links and quotes when I find them that I might want to write about later. This is the “breathing in and out” of inspiration that Derek Sivers wrote about.

This is also why I built Quotebacks with Toby Shorin - a tool and protocol for quoting writing online. I’d love to find time to build more micro-tools for bloggers and the online writing ecosystem.

Do you have an ideal creative environment? Also do you believe the physical space influences your creativity?

Anywhere that has coffee will do.

A question for the techie readers: can you run us through your tech stack?

My site is built using Jekyll and hosted on Github Pages. You can see the whole repo here: https://github.com/tomcritchlow/tomcritchlow.github.io

There’s a bunch of other things that play a part:

• Buttondown for my email newsletter
• Plausible for analytics
• Hypothes.is for annotations on blog posts
• Commento for blog comments
• Are.na for saving links

I write posts in VScode in markdown and push them to Github to publish. I’m not sure I’d recommend this “bare metal” approach to blogging but it’s kind of fun because I can play around with whatever I want very easily. I’ve tried a tap stories format for my blog posts, or an archive of every external link on the site (1797 links at time of publish) or a digital garden or a publicly accessible feed reader.

This kind of “breaking the form” stuff is mostly just experiments but they’re always tons of fun.

Given your experience, if you were to start a blog today, would you do anything differently?

I wish I’d figured out why blogging is so important to me earlier. And committed to riffs. And written more. And written weeknotes. And not stopped blogging for two years when I worked at Google. And never written on Medium. And started an email list earlier. And really committed to Hypothesis as a platform. And built my own annotation system for the web. And posted more photos. And done more blogpunk. And linked out more. And written more about my kids. And shared more of what’s not working in my life. And written more. And written that damn junkfeeds essay. And doodled more. And. And. And.

Financial question since the Web is obsessed with money: how much does it cost to run your blog? Is it just a cost, or does it generate some revenue? And what's your position on people monetising personal blogs?

I don’t monetize my blog directly though like many others it’s been a springboard for…. literally everything? I’m not exaggerating when I say that I don’t think I’d have been able to sustain a 10 year independent consulting career without my blog.

But more than financial rewards, the friendships, discussions and connections that have come from blogging have changed my life.

Time for some recommendations: any blog you think is worth checking out? And also, who do you think I should be interviewing next?

A lot of the people I’d recommend have already been mentioned! I’ll try and add a few I haven’t seen mentioned:

• Alan Jacobs ranges across topics but is always thought provoking: blog.ayjay.org
• Shannon Mattern is one of the most prolific writers and thinkers in public that I think more people should really engage with! She posts blogs, syllabus, presentations and more all on her site.
• Jarrett Fuller talks design, education, architecture and more: jarrettfuller.blog and his excellent podcast: scratchingthesurface.fm
• Henrik Karlsson is one of the most engaging writers out there right now: henrikkarlsson.xyz
• Erin Kissane is a must read. Their series on Facebook and Myanmar was excellent and important. And I’m enjoying their latest project: wrecka.ge
• Sara Hendren writes excellent pieces on architecture, the built environment, bodies and I’ve been reading her blog forever:
• Frank Chimero is one of the greats and just redesigned his site, maybe more writing coming soon? His piece the web’s grain is one of my all time greats.

For the business nerds:

• Will Larson writes some great business pieces: lethain.com
• Cedric at Commoncog (mixture of free and paid) is writing the best business writing out there today: commoncog.com
• Dave Kellog posts some great stuff that is not the same business 101 advice you read elsewhere: kellblog.com
• Vaughn Tan has some excellent thought provoking bloggy pieces on business, uncertainty, Ai and meaning making: vaughntan.org
• When Mandy Brown writes I drop everything to read it, but in addition to A Working Library she’s got some great pieces focused on the world of work under her newer Everything Changes site.

Final question: is there anything you want to share with us?

I’m having a lot of fun writing a little series of provocations about near futures thinking with my friend Brian at Little Futures. We’re working on a print on demand recap soon so stay tuned for that.