3,573 Days On The Road

If there’s one constant through my independent consulting journey, it’s that the road ahead is full of surprises. At the end of my last reflections 9 years on the road, I wrote:

“I think I’ll be doing some version of consulting for the next 20 years.”

Ha, well.

October 24th, 2014 I quit my job at Google and went out on my own. Over the next decade I worked with over 45 clients large and small all over the world. On August 5th, 2024 I took a job. So this is a special off-season “on the road” update and likely the last of these posts for a while.

The Story So Far

This series is called on the road because being an independent consultant for me felt a lot like being on a long road trip. Untethered from a stable home, with the open road ahead - the wind in your hair, but also with a feeling of loneliness, of always moving on, of always having to pack up and get back in the car, get back on the road and look for the next place to sleep.

“because he had no place he could stay in without getting tired of it and because there was nowhere to go but everywhere, keep rolling under the stars…” ― Jack Kerouac, On the Road

I’m not going to lie - independent consulting was a magical time. It afforded an incredible amount of freedom - both time freedom and money freedom. Some highlights from the last 10 years:

• The first time a “real business” signs your SOW and pays your invoice you start to feel the horizon opening up in front of you. Just a limitless sense of operating outside of boundaries and without constraints. (Year 1)
• The first time you get hired for truly, deeply interesting work - the kind of work you would legitimately want to be involved in even if they weren’t paying you. (Year 2)
• The emotional, financial and time freedom to invest yourself in all kinds of quasi-work activities (like blogging) and non-work activities (like Kung Fu).
• The agility and optionality of being independent to be able to take an 18-month road trip during COVID, while the kids were young (year 6)
• The space to be able to remain intellectually interested in the work, studying, reading papers and writing essays - while doing the work but not being so overloaded to be able to pick your head up and think.
• The ability to attract a rag tag band of fellow indie travelers - to find fellow weirdos, vagabonds and eccentrics to be able to draft off of, talk to and ask for advice. There are no good formal support structures for indie consultants but there sure are some magical half-hidden loose networks that function the same way.

So why take a job?

Half way through a 40-year career

Will Larson is a bit of a role model for me - someone who’s done time as both an independent and as a full time employee and blogged through all of it. In his great piece A 40 year career:

So as I pondered my father’s retirement, the question that caught hold of me was: How would I approach my work differently if focused on growth and engagement, and if I measured eras not in equity and IPOs but instead in decades? I’d focus on a small handful of things that build together, with each making the others more impactful as they compound over time.

I’d focus on pace, people, prestige, profit and learning.

I turned 40 last year so I’m about half way through give or take. And one thing I noticed about the last 12-18 months of consulting was a deceleration in learning.

Consulting has had plenty of ups and downs but there always felt like there was a kind of forward momentum - a feeling that each opportunity was fresh. Even if some clients were more interesting than others there was always a sense that each client taught me something new. I’d leave each consulting engagement with new eyes and a fresh perspective on the world.

But the last 12-18 months have felt… less so like that. Perhaps it’s simply the harder economic climate that sucks the fun out of the room? Or perhaps I was simply pushing through my own plateaus? Either way if you read back through 8 years on the road and 9 years on the road there’s a definite sense of feeling stuck, feeling like change was needed.

So. When the opportunity came up to go full-time with a consulting client - where I knew the people and I could see there was plenty of interesting challenges to get stuck into, I decided to take it. A change of pace, a change of environment, a change in learning. Let’s see where the rabbit hole goes!

More on the specific opportunity in a separate post…

10 Years of Consulting in Charts

Let’s have a quick data interlude. First, the aggregate view of 10 years of consulting:

Some notes:

• 2024 was my best year ever in absolute terms (by a whisker, beating out 2018). And that only counts Jan-July!
• You can see how much the SEO MBA propped up some slow years in consulting 2022/2023.
• Oh boy to be young in the summer of 2018 again 😍

And now for the more detailed view of the last 10 years (forgive the Google Sheets color formatting)

Some notes:

• There are a variety of small little projects that aren’t even plotted on the chart - you can see how the last 10 years have been dominated by large, retained clients (the average length of a retained client was > 18 months last time I checked)
• The SEO MBA (light grey) really propped up the last few years of income (or was it that focusing on the SEO MBA left less time for consulting?)
• April 2023 - April 2024 was a very long dry stretch for consulting.
• My longest running client (blue) was 2016 - 2024, with a brief gap during covid (you know who you are, much love ❤️)

Writing

The three things I’m most proud of from my indie consulting journey are:

1. Doing good work for good clients
2. Supporting other indie consultants on their journeys
3. Writing

Writing and consulting for me are deeply inter-twined. Venkatesh Rao, prolific blogger and writer was my first real indie-consulting role model and the freedom to write as I wanted over the last 10 years has been truly magical.

I’m proud of the book on indie consulting even if it’s still not quite an actual book yet. The process of writing it in public has been super rewarding and is one of the things that allowed me to attract a roster of other independent weirdos to my orbit. Much love to every single one ❤️.

Ok, so let’s talk about the book for a second. After dragging my feet for far too long already I decided to PROPERLY focus on the book for a season at the start of this year. That process led to a very-close-to-finished manuscript. It’s an actual book! Not just a collection of blog posts… But as the year progressed it became clear that I needed to get back to work to keep some money coming in and the book once again fell to the back burner.

So it’s still the plan to get the book finished and published, but I’m also kind of done making excuses. There are clear moments, especially over the last few years, where I could have prioritized the book over free time. But instead I chose to take the time and spend it in other ways - with the kids or on other adventures. So when is the book going to be finished? Ha, well tune in next year and let’s see how far I got.

Meanwhile, although I didn’t post a lot of posts this year, there are a few I really enjoyed writing and I definitely stuck to my mantra - anytime I felt stuck I wrote a blog post. Magic.

• Narrative Aircover & Compound Narrative - how to start (and end?!) an indie consulting career. With narrative.
• Manifesting my dream clients for 2024 - I didn’t end up working with any of these companies but the post certainly stirred up a bunch of interesting meetings
• Don’t give advice, be useful - the best ending to any of my essays to date I think
• Notes on search and AI - a classic riff, with more questions than answers…
• How do you cultivate customer-centric executives - still a problem I’m interested in
• Work is a place - some musings on WFH
• LinkedIn is not a social or professional network, it’s a learning network - not sure what I was trying to do here but I still think this through-line is interesting
• Working with founders who have conviction and taste - perhaps the best articulation of the kind of clients I work best with

Onwards

Thank you to everyone who supported along the way, thank you to everyone who hired me, thank you to everyone who read my blog.

So, what’s next? I’m still finding my feet transitioning into a full time thing but there’s one thing that I really hope I can figure out - and that’s the ability to keep blogging through it.

Blogging after all, is the way through.