After two years of Spanish in high school, and two more in college, I could conjugate verbs. I could read newspapers.
But I couldn’t order a drink in Valencia without the waiter switching to English.
Book knowledge had failed me. So I built a practice routine – an actual training plan, not unlike what a pianist or Shohei Ohtani might follow.
Here’s what it looked like for me:
- Daily reading in Spanish over coffee
- One podcast episode each day (Radio Ambulante or Coffee Break Spanish)
- Four Duolingo lessons per day
- Flashcards before bed
- Skype lessons twice per week with a professional tutor (plus homework)
- Informal conversation every Friday with a friend at the same level
- Weekly movie night in Spanish
- Periodic language meetups
- Motivational trips booked in advance (Mexico, Peru, Panama)
I clocked about 12 hours a week. It wasn’t spontaneous. It was structured. And it worked. Eventually, I hit a C1 level.
But what stuck with me wasn’t just the language. It was the scaffolding and the value of a conscious curriculum. The necessity of showing up even when it wasn’t exciting. The way goals became believable once broken into drills and rituals.
I’ve repeated this structure across domains ever since. Recently, I’ve applied it to Jiu Jitsu, chasing my blue belt with a bit of brute force, but also by mapping what “good” looks like and carving a pathway through constraints: classes, tutorials, a notetaking journal, periodic retreats, and enough frequency to build a rhythm without burning out.
But my real profession isn’t learning languages or martial arts. It’s building companies, leading teams, telling stories, crafting strategy.
So the deeper question returned: What does training look like for the knowledge worker?
What Is a Marketer Training For?
Most marketers (myself included) don’t start their careers with a defined curriculum. There’s no bar exam. No clearly defined ladder. The field is wide open. That’s part of the appeal (at least for those like me who cannot stand rigid constraints).
But the flipside to that freedom can feel like aimlessness, which can lead to its own flavor of burnout. Because without structure, growth becomes reactive. And when growth becomes reactive, it can feel overwhelming. You learn what your job throws at you. You specialize by accident. You feel behind because LinkedIn influencers tell you you’re behind.
To avoid that, I started by defining where I wanted to go.. I knew I wanted to build something. I wanted to run a company. That became my orientation point after stumbling upon entrepreneurship blogs in college.
First, I chased opportunities that would teach me what company building looked like up close, joining a pre-seed startup out of college as the first employee.
But throughout my career, I also focused my skill development on a few consistent pillars:
- Writing and communication – from journalism school to essays at CXL to a personal blog to memos to slide decks, this is the keystone.
- Decision making – sharpened at CXL through experimentation and decision theory, bolstered by a study of statistics, data, and behavioral science.
- Networking – cultivated at conferences, through content, and by constantly building weak ties that turn strong (and always following up).
- Operations and P&L fluency – an area I came to later, but now prioritize deeply as a founder.
I veered in and out of focus at various times, but these have been the through line for my practice. Often, I have used Ryan Holiday’s “swarm strategy” against a skill or knowledge area, deeply immersing myself in both active practice and knowledge accumulation: reading, writing, reflecting, getting feedback, setting reps, and building rituals.
The Benefits and Limitations of Scaffolding
Along the way, I stumbled into the concept of the T-shaped marketer – broad generalist knowledge across channels, with deep specialization in one or two. Mine became SEO and experimentation / CRO. At every company, I chose roles that let me deepen those spikes.
Being completely honest, I read an article by Brian Balfour in college about becoming a customer acquisition expert that used this model, and I just kind of stuck with it. But models are models.
I’m not even sure the T Shaped Marketer is a good model. It has worked for me, but I’m also naturally a dilettante, only recently having learned the benefits of committed focus. I think other models could probably work better for other people, time periods, or disciples.
More useful than the model itself was the act of having a model. It was a blueprint for me – a way to think through where to focus and what to ignore.
When the Terrain Shifts Underfoot
The wrench thrown into the equation here is that the terrain itself is morphing.
Unlike jiu jitsu or the Spanish language, marketing involves a complex interaction between consumers, platforms, brands and competition, the tools we use, and marketers themselves.
In marketing, there’s not even really a “right” answer often. As Rory Sutherland puts it, “The opposite of a good idea can also be a good idea.” So there’s a selection for creative capability and strategic flexibility.
But now, there’s AI.
Returning to the T Shaped Model, how does one expect to become a top 1% SEO expert when SEO itself is evolving so rapidly? Should a writer continue to practice writing, or should they shift to becoming an editorial cyborg – a human in the loop that builds AI systems through platforms like AirOps?
Everyone has an opinion, especially the vendors who are building in these emerging spaces. AirOps wants you to be a content engineer, Profound wants you to be an AEO specialist.
And everyone else is seemingly just becoming an influencer who is influencing others to influence (how many LinkedIn posts do you see that are simply reflections of posting on LinkedIn?).
Spanish didn’t change while I was learning it. Neither did the basics of Jiu Jitsu. But marketing? Marketing shifts. Platforms shift. Consumer behavior shifts. Entire toolsets evaporate. Today, we face the added complexity of AI reshaping not just the medium, but the meta – how work gets done, and who does it.
So how do you build a training routine in a landscape that refuses to sit still?
I personally use the barbell strategy.
On one end: robust, enduring skills like writing, decision making, data literacy, storytelling, systems thinking, networking and people skills.
These are the equivalents of cardiovascular fitness or musical ear training: never obsolete, always improvable.
On the other end: speculative, high-upside bets. For me, that includes:
- AI search / AEO
- AI operations and vibe coding
- Content engineering and workflow design
The middle of the barbell – the trends, the tools, the buzzwords (“ABM,” “Allbound,” “Nearbound”) – I mostly ignore. I track them, and generally understand what is going on in the space, but I don’t train them..
That’s a personal choice for me. I’m not saying it’s right for everyone. But I cannot feasibly keep track of every new marketing framework or trend and still stay sane and actually build what I’m trying to build.
“Play with the Tools”
A few phrases keep popping up in my ecosystem: “AI won’t replace you. Someone using AI will” and “no matter what you do, make sure you’re playing with the AI tools.”
I think these have some directional truth to them, but they’re incredibly vague and anxiety inducing. What does it mean to “play with AI tools?”
Since there are new tools coming out all the time, I like to apply specific constraints to make sure I’m using my time well. Essentially, I pick things I want to accomplish or projects I want to build, and I then select tools, skills, or knowledge that will help me see them to fruition.
I did this when learning R, which was a function of a larger goal to build technical skills (eventually focusing on Python and SQL as well). To bring my practice into focus, I picked a project at CXL: build data-driven user personas using clustering in R.
I was able to both build a useful and valuable project, and I also learned a ton about R through the process.
I do the same with AI tools today. Instead of entering the amorphous space of “playing with the tools,” and ending up in a Sora rabbit hole making videos of my dog, I pick projects. I want to automate content briefs. I want to build a tool that ingests voice of customer transcripts and outputs prompts to track in AI tools. I want to vibe code an interface for client feedback.
Then it’s possibly so filter the tools and skills needed to get to that endpoint, and in the process, you extrapolate the specific to the general (“This idea that there is generality in the specific is of far-reaching importance.” ― Douglas R. Hofstadter)
As an aside, learning R allowed me to, eventually, build out a custom data tool that enabled HubSpot to scale the Surround Sound SEO strategy that is now so important for AI search.
You never know how this stuff will play out!
My Practice Today
Okay, so how do I personally practice today? Some of my job as founder is marketing, of course, but most of my practice now relates to management and leadership.
Specifically, in that domain, we’ve hired a wonderful fractional COO who is not only providing direct value, but educating us on what it means to run a grown up, scalable business.
I deeply pore over P&Ls, financial forecasts, and I play around with models and ideas (many influenced by the book Thinking in Systems by Donella Meadows).
I’m deeply investing in what it means to attract, hire, and train talent. I’ve read dozens of books on the subject (shout out again to Tyler Cowen). I have dozens of “passive recruiting” coffee chats each month. I interview other hiring managers and functional leaders and see how they attract, hire, and train talent.
Probably most importantly, I’m very attuned to the market more generally. I spend my most valuable time close to the customer. This is low friction for me, as I take most of our sales calls. But I also sit on as many client calls as possible, run a few accounts myself, host and attend dinners and meetups in the city, talk to VCs about emerging trends, and generally overextend myself socially and collect as much information about SEO, AI search, and what is changing in the market as I can.
I still write a lot.
I write this weekly newsletter (mostly weekly). I write a personal newsletter each month. I write LinkedIn posts, memos for my team, memos for clients.
I don’t talk about this often, but I’ve spent the past year obsessed with the theme of “storytelling,” and I’ve built a daily practice of Homework for Life (from Matthew Dicks’ book Storyworthy), and I often practice different formats and structures of storytelling on this newsletter, and more so, on my personal newsletter.
I translate this storytelling practice into slide decks for prospects, all hands meetings for our team, and our sales pitch itself. I’ve tried to marry classic storytelling techniques with those adapted for sales and marketing (April Dunford’s Sales Pitch book is extremely useful here). All of this points to positioning and messaging, which I spend a lot of time thinking about. I even practice storytelling when I’m getting drinks with friends.
I spend somewhat less time developing specific data or technical skills. It is a better use of my time to identify people we can hire or contract who can do that, which circles back to my HR focus.
I’d say the backbone of all of my practice continues to be writing. Writing is the keystone habit that forces clear thinking, enables storytelling and communication practice, extends my networking reach beyond IRL interactions, and helps me communicate our positioning and messaging to the market. I think it will be even more important with the emergence of AI.
If I gave up everything else, I’d still write.
Want more insights like this? Subscribe to Field Notes
