October 24, 2019

5 years on the road

Thoughts on sustainable independence

I’ve been independent 5 years today.

Exactly one year ago I posted 4 years on the road. After an incredibly busy summer, my retained revenue had just dried up and I ended on a cliffhanger:

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.

Later that afternoon I get a short note “We can do this if you still have Nov/Dec/(Jan?) free.” - an old proposal came back to life out of the blue.

Digging back through my email I see that I initially reconnected with this contact after posting my TWO years on the road piece:

Then, after some back and forth a dormant proposal came back to life and closed the afternoon of October 24th 2018:

5 days later I started in their office three days a week and I’ve been there for the past year.

Funny how things go.


Here’s some highlights and happenings from the past year:

  • Helped my partner Erin launch a Kickstarter for her kid’s book.
  • Begun a regular and consistent Wing Tsun practice at - feels great to get back into the groove
  • Didn’t travel even once for work - an incredible luxury for an independent consultant and highlights the privilege of working in NYC
  • Watched Roxy grow up (3.5 now!) and learn to tell jokes, brush her own teeth and so so much more. Baby #2 (a boy) on the way in December!
  • Continued tending to my networks via dinners, coffee meetings and more.
  • Attended a one day Masterclass from Jan Chipchase on sensemaking for impact which I really enjoyed
  • Spoke at the iAnnotate conference in DC on annotation for bloggers


Here’s the full 5 year view of work (each client being a different color):

And here’s just the last 12 months:

You can clearly see how much this one client has dominated my work over the past 12 months - something I’ll likely talk about soon as the feeling of being a “perma-lancer” is strong here and it has a bunch of pros and cons combined.

Mostly however I’m incredibly grateful to be able to have steady work all year.

Here’s some themes, ideas and notes:

Gratitude for my Blog & for Those That Blog

I’ve written 27 posts so far in 2019 and blogging continues to be one of the most long-term rewarding things I’ve done. The networks, connections and fun I’ve had has been immense. And(!) look back at that email from 2016 that led to a large client engagement for all of 2019. I wrote the post ways of seeing all about the weird ways that work finds you as an independent but *blogging continues to have a long-term compound interest effect.

Shout out to the modern 2019 blog-scenius folks. You know who you are.

Few of my fave blog posts from the last year:

  • Exploring the UX of annotations - this one led to me speaking at the Hypothesis conference in DC earlier this year
  • Building a digital garden - this one really struck a nerve and I love watching people build personal wikis and gardens off the back of this post.
  • Blogpunk - this is a small little idea but one that’s important. More to think about here. Shout out to Howard for the conversation that prompted this.
  • New Blogging - Blogchains - I set up the code for blogchains on the site and while it hasn’t quite stuck I’m keen to keep pushing on this format to see where it goes
  • Networked communities blogchain - this one started with Brendan Schlagel. I’m slightly stalled here because I’m due to write the next post and it’s currently 4000 words…. Lots of potential here though in blogchains and in the networked communities idea. Watch this space.

What Book Writing Means to Me

It’s crazy to think that only one year ago the book project was still a “maybe kinda” thing:

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.

Now - the book (working title: The Strategic Independent) is a firm capital-P Project. It’s happening.

See the outline here.

I’ve now got about 25k words written on the site deliberately under the strategic independent theme and another ~20k words in draft waiting to be finished.

Deciding to write a book was a big insight and drive that came from working with my coach last year (thanks Sunil!) and I’m incredibly grateful for the push. Being able to point to the book as a legitimate project and ambition is rewarding - most importantly because I’ve wanted to write a book (any kind of book!) for a long time so I get to scratch a “personal identity” itch.

But there’s another reason writing a book about independent consulting is valuable - because it allows me to treat this 5-year “on the road” journey as a single narrative journey connected together by my introspection, study and analysis of the practice of independent consulting. This helps me treat this venture as something that is building and growing (and that I’m personally growing!) rather than as a series of disconnected client gigs.

Still though - getting from words written to an actual book is hard! I’m confident that the book will get made in 2020 but it’s still gonna take a bunch of work…

Product Design Sprints

One new kind of work that I’ve found this year is partnering with designers to build product design concepts in a tight “sprint” fashion. I’ve done two of these and really enjoyed the process - being able to collaboratively switch back and forth between strategy and design has produced some really interesting projects for clients.

Of course, the down side is that both concepts that we worked on are somewhat in limbo with the clients. Speculative design has a habit of getting “stuck” or re-prioritised. In both cases the projects have had impact but just not in the ways we anticipated exactly.

I’d really like to do more of this work and I’d like to find ways to help un-stuck it better (or realize the adjacent value better). More to learn and experiment with here in 2020.

Little Futures

I’ve partnered with my friend Brian Dell to launch Little Futures which is a research studio to make futures thinking less abstract and more grounded - to shine a light on “arm’s-length futures”. Neither of us are really sure what this means but the core product is a weekly email newsletter where we write what can best be described as business zen koans. They’re fun and people seem to like them. Catch up here:

We’re having a ton of fun with these and I’m really excited to figure out how to make Little Futures a bigger part of 2020…

Money Musings

Overall 2019 was great and very stable revenue-wise but being independent forces you to think about money in new ways. I took a holiday during a client consulting project and as a result it was a 5-figure holiday due to time off client work. With baby #2 on the way in December I’ll take time of client work in Jan/Feb and that’ll likely end up being a 5-figure paternity leave.

These things are broadly “priced in” to what I charge but that’s a different story to actually experiencing the decisions - (“should I take a holiday to see family? is it worth 5 figures?”)

I’m posting this not to complain - these are all deliberate choices I’m making but rather thinking about and rationalizing money is a funny thing when you’re independent and I hope there’s value in talking about it and sharing stories. I think there’ll be a chapter in the book about this…

Thank You

In summary - 2019 was a year of grace, movement and joy both at work and at home and I’m incredibly grateful for everyone who helped and supported along the way. Too many names to list but a huge THANK YOU to everyone.

Onwards on the road.

As Jack Kerouac said:

“There was nowhere to go but everywhere, so just keep on rolling under the stars.”

More blog posts:

A Lil' Website Refresh

March 20, 2024

Work is a Place

March 6, 2024

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