October 24, 2018

Four Years on the Road

Sustainability, Independence & The Unknown

October 24th is the anniversary of when I quit my last full time job to head out as an independent consultant. Catch up with 2 years on the road and 3 years on the road

Four years on the road. The metaphor of the road-trip still rings true - a sense of not having a stable home but rather having to make your home wherever you are. Unmoored and untethered. Dislocated from the system.

The benefits are strong - being in control of your own life in a really fundamental way continues to be deeply rewarding, even more so while my daughter Roxy is young. Of course there’s tradeoffs - the hardest fights continue to be the quest for a stable identity, meaning and understanding which direction you’re supposed to be driving in.

But overall year 4 was a good one.


Some quick hits:

  • This year I had almost zero business travel. As a consultant this is the dream - and a direct consequence of building a strong local presence here in NYC (and of course there being plenty of work on my doorstop)
  • Roxy is 2.5 now and scooting, telling jokes and making up songs. A daily source of inspiration and grounding. And a constant reminder of how important a flexible schedule is as we navigate sickness, school dramas and more.
  • A quiet start to the year which enabled a trip through Uruguay followed by a manic summer period of intense work (more on that below). A good reminder to trust the process and embrace both the quiet times and the busy times.
  • A steady evolution in the size of clients, seniority of the work and confidence in my model.
  • I started working with a professional coach at the start of the year and have had a very rewarding experience and it’s nice to feel like I can justify an accountability partner, mentor and cheerleader!
  • Started and paused The Malcontents, a podcast with my buddy Sean Blanda. I found the process of recording a podcast super rewarding but as a side project for both of us it’s been tough to prioritize and focus on. I’m convinced some form of podcasting will return for me but not sure exactly what format yet…

Peaks and Valleys

When I was first starting out on my own my friend Dave Dawson said you have to embrace the quiet times and the busy times. Work nights and weekends when you have to, but make sure you go biking 11am on a Tuesday too when you can. You have to embrace the whole lifestyle to get the benefit.

This has been more true than ever this year - this is four years of consulting work (with each color being a different client):

You can see the quiet start to the year and then the frenzy over the summer! And if you squint enough you can make out the cycles of work coming through:

Some thoughts looking at this graph:

If you go all the way back to the beginning of the journey the first 9 months were pretty bumpy and sporadic until I hit two stable retained clients at the same time. One of those lasted two years and the other I’m still working with today(!).

That retained revenue is the secret to so much. In my mind it’s the key to doing interesting work and to creating a sustainable business. I’ve got more to write about how I focus on retained revenue and how I end up working with clients for years at a time but I teased it in my strategy and stewardship post:

For a long time I resisted the execution and project management of my strategy work with clients. I felt like if I got caught up in the weeds I was going to be doing work that wasn’t as interesting and wasn’t as well paid as the strategy work.

But the truth is this - strategy that lives in docs and presentations is worthless. And businesses live and die by the momentum of projects. So helping clients at critical points to move the chains forward - often in incredibly tactical ways, but always within the wider strategic framework - is deeply valuable.

In month 1 I’m always doing strategy. In month 6 I’m often overseeing specific pieces of content production. Then back again into strategy in month 9 as we review and check in.

At the start of this year with a few projects wrapping up I had a quiet period and then two meaty projects over the summer nearly crushed me. Thankfully I’d shored up emotional and psychological strength in January to hunker down and lean into the busy period.

And finally, note how slow I am right now. For the first time since June 2016 I’m at a lull. It feels nice to be cruising out of the city with the windows down and the music playing finally free again! We’ll see how long before the deamons appear nibbling at my heels demanding revenue.

Tending to my Networks

My network is the most valuable part of my business and I have continued to invest and cultivate new friends, new faces and new connections. There’s a semi-regular dinner series that I host with an amazing group. There’s regular coffee meetings. Writing and creating new connections.

Building a network of peers - weirdos and misfits like myself who are trying to figure out their own path through the world has been not only rewarding but also deeply valuable. All of my leads come via my network so I see this as a deliberate activity to grow my consulting business but also a necessary task to ensure that I have a support network should I need it (and to provide a support network to others!).

This network has provided some sense of stability to this independence. And some social interaction :)

I’ve also been slowly and steadily growing my tinyletter audience. As this grows I anticipate that this will become an increasingly interesting part of my intimate network - sharing thoughts there feels very different from blogging so it’s fun to flex a different type of writing there.


There’s a lot of angst around positioning. I think many independents struggle with it - I’ve struggled with it! But I’m starting to find some peace here. I realized that the game of positioning is not an external game - it’s not so much about the face you present to the market as much as it’s the story you tell yourself internally!

This realization has helped me better understand what it is I’m chasing (a stable identity!) and also to understand that it’s never going to fully materialize.

Looking back my previous attempt at positioning isn’t wrong per se but it’s perhaps overly… simplistic? generic?

This is from last year:

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

Earlier this year I uncovered (invented?) the concept of Media Design. I took a stab a definition as follows:

Media Design is the practice of designing effective systems of content within the overlapping ecosystems of technology, distribution, production and experience.

With the uncovering of media design earlier this year my positioning and narrative is basically I do strategic media design work through strategy and stewardship.

This is a less concise framing but I think adds some more nuance to the kind of work I do and feels like it rings true.

Some example client work from this past year:

  • Put together a high level content vision for a business that creates content at significant scale across 20+ websites and many international markets. A mixture of strategy to decide the right thing invest in and people to understand how they might adapt to the vision to get it done. Fun stuff.
  • Led audience development for a digital magazine that had very little digital infrastructure, supporting them through a large transition period as they were spun out of a holding company to be independent which included a complete digital re-platforming and building a new audience development team internally
  • Supported a media company you’ve definitely heard of as they went the other way and were acquired by an umbrella brand. A fascinating merging of cultures. This was an interesting project where the strategy was relatively modest but required a ton of process work to help them do new things in new ways between two teams that had different cultures.

As an aside - I’m finding writing case studies to be challenging. Who’s story is it to tell when you’re so deeply embedded in a client’s organization that you’re essentially just one of the team? Something to chew on.


2018 has been a great year for writing! Tons of blogging that I’m proud of. Some of my personal faves from the past year:

But blogging is only the surface… I’m starting to think about writing a book. It’ll be something like a manual for other independent consultants - based off my writing around the consultant’s grain and a fieldguide for independent consultants and attempting to thread the needle between theory and practice.

I have an outline for the book and my plan right now is to blog most of it - getting the heart of the writing out on my blog over the next year or so to build up a body of work that I can hire an editor to partner with and dress up into a book.

Writing longer form is hard though! It feels very much like learning a new skill. But I’m excited about the challenge and while client work is slow it’s good to have a project to keep me productive and engaged. I’ve got the first longer piece of writing coming out in the next week or so that’s deliberately designed to fit into a book-like object so I’m excited to do more of that kind of writing and to get better at it.

The Year Ahead

So what next?

I’m floating in this funny space - I trust the process now more than I ever have and I feel confident more work will come along. But at the same time what that work will look like is a mystery right now!

The road ahead is open. The windows are down. The mixtape is on. So far so good. Onwards where the road will take me.

Much love and thank you to everyone who’s supported me on this journey so far. There are too many to list here but I love you all.

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This post was written by Tom Critchlow - blogger and independent consultant. Subscribe to join my occassional newsletter: