Tom Critchlow
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Three years on the road

A personal note on how it's all going...

October 24, 2017

Three years ago today I walked out of Google into the crisp autumn air of independence. My friend Jonathan Schnapp hosted a quit party for me at the Royal Palms shuffleboard club and I was suddenly out on my own.

It feels a lot like being on a endless road trip - a feeling of ultimate freedom interlaced with a nagging anxiety of being adrift with no stable home.

Overall, year 3 was wonderful and I feel incredibly fortunate to be able to pay the bills doing what I do and still get home most days to read Roxy some Harry Potter before she goes to bed.

Some quick highlights from the past 12 months:

The positioning for my work I came to last year is holding up pretty well. Here’s how I describe what I do when asked:

For content companies looking to invest in growth I’m the secret weapon embedded in your organization to build & lead strategic initiatives.

The focus on deep embedded work led to some very long client engagements and most of 2016 and 2017 was dominated by two large multi-year projects both of which wrapped up this summer. So the road ahead is opening up again. Time to roll down the windows, put on the roadtrip-mixtape and go where the wind blows!

So what’s top of mind for me as I head into the next year? I’ve broken it down into 5 obsessions:

Obsession #1: Workshops as work

All business problems are ultimately people problems. Sure, I love putting a good spreadsheet or presentation together but what really lights me up is getting in a room with clients and collectively going deep into what the actual challenges and opportunities are.

Almost all of my client engagements now start with an initial workshop (in person preferably) allowing us to cover a lot of ground and dive into the business without ignoring the weird, beautiful multi-faceted people involved in the process.

The best size for these workshops is 4-6 people and my best tip from Matt Webb is “always have something on the table”. It’s key to bring inspiration and outside thinking into the workshop to avoid it becoming purely insular. A good workshop ultimately has to be about the world and how the client fits into the world.

Not only that - but it’s too easy to think you know a client’s business but if you’re not close enough to smell them you’ll miss the necessary nuance needed to execute. I’m constantly guided by this lovely definition from Stripe Partners to view strategy as “an unfolding network of people, shared experiences and artefacts that is constantly being remade”.

Yes. Yes!

Obsession #2: Supporting independence

Over the past three years I’ve found myself a merry little band of independents. Those peeking through the cracks of late stage capitalism into the future - what Franco Berardi calls “fractals of time and pulsating cells of labor.” I’ve talked before about how useful it is to have a network around you when you’re on your own but specifically I’m starting to assemble a set of peers who are doing similar work - of course the joy is that everyone is doing their own unique blend of work but there’s enough overlap to feel like we can draw on each others experience.

I’m excited to keep connecting the dots here and helping those just starting out as well as learning from those who are far more experienced than I am. Perhaps look for an unconference of independents in 2018 if I can find the time… In the meantime, if you’re an independent consultant drop me a line, I’m always keen to chat.

For more here see my post a fieldguide for independent strategy consultants.

Obsession #3: Effective consulting

I’m increasingly coming to the idea that effective strategy consulting is all about ways of seeing (the phrase taken from the John Berger TV series). As a consultant your job is to bring new ways of seeing to the client and then turn those insights and realizations into strategy and execution.

I touched on this above with the workshops but how do you actually effect change within an organization? Anyone who tells you it’s easy is lying. For years I’ve tried to do more than produce reports and documents but I still feel like there’s a lot to learn and explore here.

In particular - I’m really interested in how much internal content within a company plays a role in the spread of ideas. I also coined the term consulting fast and slow which I really like and sums up a bunch of my thinking on this.

I dived in deep to explore this idea in my post the consultant’s grain.

I went on to write about the critical question of telling a client their content is not good enough. I wrote up that thinking here: how do you measure good content. That post explored surveys as a way of reflecting qualitative insights back into the client but I’m still looking for ways to reflect insights back into a business.

Obsession #4: Branding in the age of content

Much of my work involves content. But so much of content on the web is deeply flawed - there’s too much mediocre content written for no-one spread to everyone.

As a society we’re pawing our way through glossy content in a seamless, attention-less way.

Where does brand and emotion live in this world? It’s a provocation I’m struggling with but I think I’m starting to make some real progress and the more I look at it the more I think almost everyone is doing it wrong. That’s exciting. It either means I’m slowly going crazy, or… I’m on to something.

Watch this space. But there’s some notes here: branding in the age of content.

There’s so much more here.

Obsession #5: Weird work

Last year I wrestled with the idea of building a brand for my consulting work. Ultimately I decided not to go down that path but there’s still a nagging feeling there’s more interesting work to be done under a label that isn’t my own name. Like a record label, or an art collective, or a creative studio there’s the potential to carve out creativity into more weird forms than what I’m doing right now.

I’ve been inspired recently both by friends who are building creative studios and by the radical architecture movement of the 60s that saw groups like Archigram and Super Studio emerge - these hybrids of professional studio practice, art show, philosophy, small batch publishing, zines and just generally weird work.

So I’m starting to explore more creative avenues and partnerships to create more provocative work. Maybe it’s co-creating with clients? Or producing a zine internally for a client? Or maybe it’s becoming a something-in-residence at an organization to explicitly explore those alternative areas…

Who knows where that goes but I’m going to try and get a little more weird in 2018…

Thank you

Finally - thank you to everyone who came along for the journey with me. Friends, peers, blog readers, breakfast companions, late night whisky drinkers, clients and more. Thank you! Wouldn’t be here without you.

(For reference, here’s my update last year from two years on the road)

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