November 10, 2022

8 Years on the Road

Getting lost and learning to steer by a new compass

Being self-employed feels a bit like being on an extended road trip. Untethered and free, but lonely and unsupported too. Ultimate freedoms combined with shallow roots. Every year I write a recap, around the anniversary of quitting my last job (Oct 24th, 2014). Here’s my recap of year 8.

First you shape your narratives and then your narratives shape you.

Despite writing about the power of narratives and saying things like “the indie consulting journey is all about crafting an identity” in the last year I think I still underestimated the power of narrative.

In 2021/2022 the SEO MBA ramped up, took on a life of it’s own and wrecked my personal narrative like a bull in a china shop. The next year is about picking up the pieces and reformulating my indie career.

But let me back up. First, some highlights:

  • Roxy is now in first grade - she just started wearing glasses, is sassy and creative and fun.
  • Indy is in pre-school, running around like a maniac wielding his “ninja swords”1
  • Both kids got their COVID vaccines, what a historic era for science, and what a strange era for kids…
  • We moved house - still in Brooklyn but with more space for the kids to bounce off the walls! Overall probably the right move but this consumed a significant amount of energy and stress this year.
  • This recap is a bit late (my indie-versary is Oct 24th) because I was in Australia for a client’s executive off-site for 10 days. The first time I’ve seen a client in-person since the start of the pandemic.

Consultant, or…..?

Almost exactly a year ago I launched the first SEO MBA course. I knew it was broadly speaking a good idea and I knew there was demand for it but it’s still rewarding to look at this chart and see how quickly it dominated my revenue (consulting revenue in blue, course revenue in red):

But/and this came with some psychological cost. I launched the SEO MBA without much of a plan - I just knew there was demand for it and I knew that teaching was something I wanted to do more of.

And now here we are with an almost 50/50 split between consulting and course revenue. Listen, I can’t complain! This is a huge success and I’m super grateful for everyone who’s supported and engaged with the SEO MBA. On the one hand you could view this 50/50 split as healthy - as a way to generate recurring revenue, diversifying revenue streams, becoming less reliant on client work etc etc.

All these things are true.

But on the other hand I feel this 50/50 split very keenly. I’ve clutched to the identity and narrative of “independent consultant” so strongly over the last 8 years that to suddenly find myself split between these identities has caused more internal anguish than I’d like to admit. Well, ok actually let me just admit it. It’s been hard. I’ve felt stuck. Paralyzed. Weirdly conflicted about simple things.

I don’t have the solution yet. But before we think about that let’s stick with the recap a little further.

Consulting Work Recap

I’m kind of a weirdo - I actually enjoy client work. There are a lot of indie consultants and freelancers that I think view client work as a means to an end, but don’t enjoy the rituals, cycles and pressures of the consultant/client dynamic. Not me. I love it! And perhaps the biggest surprise was that between moving house, vacation and growing the SEO MBA, as my client work declined my happiness also declined.

Especially at the start of the year I actively declined client work in favor of sprinting to launch a second course - and looking back I can see that there was a knock-on effect. While teaching is very rewarding (more on that in the next section), it’s not nearly as electric as consulting. At least not the way I’ve been doing it (again, more on that later).

In terms of the actual client work - I’ve done some of my best, and perhaps worst work this last year.

The good: kind of without noticing it the majority of my work is now P&L-first. What I mean by that is that because I’m working at the executive layer inside organizations every project is a kind of finance-first project. Things like:

  • What should our SEO strategy be? Let’s see what size of SEO team we can fit inside this P&L.
  • Which direction should we grow in? Let’s take a look at which business units are high margin/low margin and model out some assumptions about TAM and growth rate.
  • How do we invest in growth, while maintaining positive EBITDA? Let’s sequence the growth initiatives and make sure we’re realizing growth as we go.
  • How do I get clarity on this business? Well, let’s ensure the executive team’s dashboard is closer to profit and margin and combines input and output metrics.

I’m not sure if I’m getting more of this kind of work because I’m routinely interfacing with executive teams, or whether I’ve become better at this kind of work because of the time spent teaching these skills as part of the SEO MBA? Or, or! Maybe there’s a recession going on and everyone is now concerned about top line and bottom line….?

Probably some combination of the above.

It’s fun though to be able to stretch across a client organization to touch product, brand, marketing, operations and connect the overall strategy back to the reality of a P&L.

The bad: It wasn’t all rainbows though. In early 2021 I did a content strategy project for a big tech company and I think it was some of my best work. I connected the dots smoothly between brand positioning and content strategy. I loved that project! So this year I tried to adapt the same approach for a much smaller client and… it didn’t work so well.

I’ll probably write a proper post-mortem at some point but in essence I got the balance between strategy and stewardship wrong. The client pushed me to create a strategy, when they didn’t have the team in place to execute on it. The client told me that the strategy was still necessary since they were going to raise money soon. Foolishly I took them at their word - partly because I was excited to roll out my content strategy approach again - when in reality I should have pushed harder for the next most useful thing (which would likely have been a 2-3 slide version of the strategy for their VC investor deck to secure the funds combined with a focus on hiring their marketing team).

I’ve been using this phrase “the next most useful thing” as a guiding light for my consulting work - I’m obsessed with being useful not just right. I’ve always rejected the fancy presentation in favor of the next most useful thing, and I simply took my eye off the ball with this one. I’m not even sure the client views this project as a real disappointment, there was still some value in it, but I’m mad at myself personally for this one. A good reminder not to take your eye off the ball. And to push your clients beyond what they tell you the right answer is.

Anyway, while consulting work over the past year has been very patchy I just signed 3 new clients this week and I’m gonna be busy for a little bit. Feels good to get back into the consulting flow. Let’s crack open some P&Ls.


I’m going to write a separate full recap for the SEO MBA [live now!] because there’s a whole world there - but let’s look at some key pieces:

  • The email list launched early 2021 and is now 8,000+ subscribers. Unfortunately I think that number is a little off since Substack has been juicing growth aggressively in the last 6 months and I’m not sure those users are high quality. Still, this number is bigger than I would have guessed!
  • The first course, Executive Presence is truly the flagship course. It’s the most differentiated in the market and has sustained more demand than the second course The Art of Client Management. I’m super proud of both courses and think both are deeply valuable, but people want to learn executive presence more than they want to learn client management. One is aspirational in nature, where one is more functional.
  • Learning how to shoot video, produce courses and design teaching programs has been interesting and rewarding.
  • I made a whole 3rd course that I scrapped before launch because I didn’t think it was good enough.

When I designed the initial SEO MBA program I consciously avoided the live-teaching model of a cohort based course. I didn’t want to chain myself to that cadence and cycle of promotion/waitlist/course event. I think this was the right decision, but it also meant that a lot of my day to day with the SEO MBA is just me in front of a laptop. It’s “teaching” in the abstract but not in practical terms.

So as I think about evolving and next steps I need to think about how to make the teaching a bit more active and electric. I’ll likely dabble with live cohorts as a complement to the self-paced courses.

Meanwhile, the weekly office hours have continued and been a constant source of joy! The people that continue to show up here and invest time with the course really get a deep sense of growth from it. New perspectives, new jobs, new confidence, new clarity. These sessions end up being high value because everyone has a shared grounding from the course. I’m going to keep doing these.

But the future roadmap for the SEO MBA is very unclear. Step on the gas with growth, ads etc? Fold in courses by other teachers? Continue to launch new courses? Double down and focus on the executive presence course? Transition to a membership model? Something else?

We’ll see. I’m actively working my way through these questions right now. Shout if you have ideas.

Writing Recap

2022 was a great year for writing! In addition to the 20 SEO MBA newsletters I sent, I wrote 25 blog posts here on this site.

I even briefly tried to sustain a weekly blogging habit! This flushed the cache for a few of my old drafts, felt energizing and generated two HN homepages. Wild what a little bit of consistent output can do! Then the summer came, buying a house and life etc and I fell off the wagon. I’d like to get back there though (maybe this is the first of my weekly blogging habit again? Let’s check in next year).

My fave SEO MBA pieces I wrote this year:

  • Is SEO worth it? - taking a little 20% beef with the SEO industry over how we talk about “SEO” investment (spoiler alert, most of the benefit of SEO doesn’t come from the SEO team).
  • Nerding out on Nerdwallet - I loved writing this piece dissecting the Nerdwallet S-1 filing in detail. Helped me understand P&Ls a bit more and helped me deepen my understanding of commerce content.
  • The SEO skills maturity matrix - hopefully a very concrete and tangible career map for SEO folks, and also a rallying cry for the “soft skills” that the SEO MBA teaches.

My fave personal blog posts this year:

  • Jan 2022 - Map of Inquiry - trying to expose the questions that are alive and interesting for me right now. This helped create some through lines across various pieces of work and writing.
  • Electric Tables V0.1 - some personal R&D work! I absolutely loved creating Electric Tables. It was a great way to manifest a point of view through a prototype. Really proud of how this came out. I’d love to carve out more time for this kind of tinkering.
  • Notes on teaching & chairs - pondering my relationship to teaching and exploring my personal mental model for creating learning environments (see also bezier butts).
  • Some notes on executive dashboards - you can see how this emerged out of my consulting work this year. I’m very happy with how this post came out and it generated a bunch of conversations behind the scenes2.
  • Reflecting on things I failed to get done at Google - personal therapy dealing with my time working at Google a decade ago. I wish I’d written this post a few years ago but I simply wasn’t ready yet.
  • A map for indie living - maybe the best thing I’ve written about the indie consulting journey?! I bashed this out in an afternoon but people still reference this one. I think the “levels” I wrote about here really ring true for people and it comes with a set of practical ideas too. This map is going to make it into the book for sure!
  • Rejecting specialization - while this was the only actual writing I did this year for the book project I’m very happy with how it came out. This was a nice contrarian take and nails a few really important ideas about indie consulting (imho!)
  • Some notes on agency at work - as I’ve wrestled with a way to unify my work and my fragmented identity this idea of “increasing agency” has emerged as a very generative and important throughline. There’s more excavation to be done here but I really like this sense of purpose that sits across all different kinds of things I’ve been doing.

Just re-reading that list and exploring the writing from the past year I feel energized to keep going. I love writing. And it’s a big win this year that I’ve been able to do so much of it.

What’s that? Oh, the book. Yes! Hmm. I’m still very much gung-ho on the book project but it is becoming ridiculous how much it’s dragging on at this point. Between the house buying, building the SEO MBA and the identity crisis the book has very much taken a backseat. But if I’m honest maybe the book is the right kind of project to crack open the future and find new opportunities, new identities?

I’ve basically written the first draft of the book - what I need now is to find an editor who can be very hands on in helping turn the body of writing into a finished manuscript. Know anyone? Send them my way.

Networks work

A huge, truly heartfelt thank you to everyone who’s supported and helped me this year. More than in previous years I’ve had to lean on my network for support, advice, company and feedback. Folks like Brian, Toby, Elan, Behzod, Howard, Sean, John, Jim & the other Jim.

As I write this, Twitter is on the precipice. I’m not going to pretend I know how this plays out but we’ve never seen a platform like Twitter for converting casual internet connections into deep friendships and for all it’s troubles I hope that whatever emerges from this current mess (Twitter or otherwise) can sustain the next decade of internet-friends.

This past year has been a deep reminder of the power of networks. Much love to you all. ❤️❤️❤️

So, what’s next?

Oh haha you crazy fool. If you’ve read this far, I obviously have no idea. But, that’s the promise of indie living!

Here’s about all I know:

  • I’m not going to go “all-in” on the SEO MBA, at least not yet. Because consulting work is still generative and electric for me. I love it.
  • There is a bunch of relatively basic growth work to be done for the SEO MBA (email funnels, that kind of thing). Tune in next year to see if I can motivate myself to do them.
  • The SEO MBA “as is” has been a wonderful first step into teaching. Deeply rewarding (and lucrative!) but the next phase and evolution has to make teaching feel a bit more electric if it’s going to compete with my consulting work.
  • I’m going to pull myself out of this identity slump by sheer force of will. Watch me (tune in next year to see how that goes).
  • I’m excited to keep up the writing habit! Bloggy-blog-blog!

And finally, a big shout out to Paul Millerd. Fellow indie consultant, fellow course creator, fellow book author! Watching from afar I get the sense that Paul is just hitting his stride this year and it’s amazing to see. I love seeing other indie consultants thrive and come alive.

I’ll leave you with this piece from Paul on ambition:

Over the last couple of years, I’ve experienced a complete transformation and reawakening of my own curiosity and desire to do challenging things in life and work.  While similar to my early career enthusiasm, this feeling is deeper, more powerful, and likely sustainable.

I believe the best way to describe this shift is as a shift from legible ambition to illegible ambition. The reason so many people cling to default metrics of success is that other people understand them. Legible ambition is a story that your parents can tell their friends. We fear that not having such legible ambition means we will be cast out of our modern work-centered culture.

Illegible ambition is personal, hard if not impossible to describe to others, and might not lead anywhere impressive, sometimes for years. But it is also immensely powerful. Illegible ambition is about connecting to who we really are and doing work in a state that friend and fellow internet weirdo David Perell perfectly describes as “hearts on fire.”

While I relearn how to steer and orient myself on this independent journey, perhaps a shift to illegible ambition is required…

As ever, I sense the winds of change a-blowing.

  1. His arms. His ninja swords are his arms. They go everywhere with him 

  2. Curiously though this piece didn’t generate any direct client work. That wasn’t the point but I did kind of expect this to generate some interest. Perhaps it was too introspective for that…? 

More blog posts:

A Lil' Website Refresh

March 20, 2024

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