Remember when I started an email newsletter last year and then stopped in January? And now it’s March. Yeah.
It went by the wayside because of a technical detail I’d glossed over when I was setting it up: in short, I'd used Beehiiv's own domain instead of my own. Images broke and I couldn’t track it to specific subscription forms. Small, annoying things — the kind that are easy to put off until putting it off becomes the habit.
But thanks to Claude, Gemini, and a few YouTube videos, I figured it out yesterday.
So, hi again.
As most of you know — about 18 months ago, I started How This Works co. But that's not the first change in my work, not by a long shot. For about the last 15 years, I’ve gone through a number of different kinds of work and modes. Let's count 'em:
web designer
UX designer
senior designer
service designer
design director
product strategist standing up a services practice with a signature offering, the Bullseye Customer Sprint
Of course, with stints of job hunting in between and some things on the side, freelancing and fractional work. But none of them were ever the same job, they don't have the same focus or the same parts. For instance, team management and budgeting matter when you're a design director overseeing $2M in billable work but it’s an unnecessary detail when you’re trying to reach a funded founder watching customers leave.
I knew this in theory but my LinkedIn profile had all sorts of deferred maintenance and leftover from previous works on it. Lots of stuff that I’d swept under the rug. Skills which are connected to recommendations and services.
Then last week, my friend Danita Delce — a fractional designer in Austin (LinkedIn) — mentioned she'd run her LinkedIn profile through an AI tool to optimize for LinkedIn's latest algorithm updates. Hm.
So I did the same. Pulled together LinkedIn's official announcements (starting with this one), found a few practitioners breaking down the practical side, dropped it all into a Claude thread, and pasted in my profile, my banner graphic, and a one-sheet on How This Works co, including my own Bullseye Customer framing.
And the thread had plenty of recommendations. Some landed, some didn't.
"Move product design out of your top three skills — it triggers 'freelancer' categorization." But I've been a designer for nearly 15 years. That's not noise. That's the foundation everything else is built on.
"List management consulting and business consulting as your service categories — that's where the retention budgets live." Maybe, but I'm not a management consultant persay. I’ve done a lot of that from the design swim lane. But right now, I'm someone who figured out how to run customer interviews in a way that actually changes what a team builds.
And then, at the end: "You are no longer a 'designer who does some strategy.' You are a strategic partner whose service is solving the $2M+ problem of customer churn."
The funny thing is I didn't ask it to rewrite who I am, I’d asked it to audit my profile.
True, Claude and Gemini were able to zero in on what the algorithm rewards. But it doesn’t know what I say on a call with a founder that gets head nods.
And then I remembered something I hadn't thought about in months.
Last year, Brad Diderickson (LinkedIn) and I were comparing notes on our respective practices. He was testing his own positioning language in conversations around being a corporate dropout and making a big change — 150+ of them now, which you can follow on his Substack. At some point in our convo, I described customer interviews as detective work, following evidence for future product failure — looking for what customers actually meant versus what they said.
Brad reflected it back to me and so I reluctantly tried "product failure detective" in my headline for a while.
In my eyes, it didn't quite fit and told Brad so back then, "I didn't like the nameplate. But I liked the scene of running a product failure detective agency. The feeling. I dunno.”
That's the thing about positioning language. You say it out loud. You say it over and over until you hear the gaps. Brad's been doing it for 150+ conversations. And then that’s what I did again when I recently revamped my LinkedIn profile with help from Claude.
Me and my dog (a Korean jindo) on a walk this morning
Open tabs in my browser right now
Daniele Catalanotto about how a shift to a "free" model for him has reduced overhead costs and technical complexity: https://store.swissinnovation.academy/blog/all-free-ripple-effects
Mike Montiero’s new book is in my shopping cart: https://www.mulebooks.com/store/how-to-die-and-other-stories
Rusty Foster and the urge to anthropomorphize AI: https://www.todayintabs.com/p/a-i-isn-t-people
Something else to consider
[Breakthrough ideas] emerge through iteration, through exploring different angles, through the friction of challenging initial assumptions and pushing beyond obvious solutions.
Storey's Creative Intelligence is a book about how good ideas actually develop — not in a flash, but through iteration, through trying the wrong version first, through the friction of someone pushing back on your assumptions. The detective agency headline was a wrong version and ‘strategic partner solving the $2M+ problem of customer churn’ was the algorithm's version. Neither was wasted because both moved something.
What I realized this week: I've been running positioning experiments the whole time. The detective detour, the skills cleanup, all of it. I just didn't call them experiments. I was fixing things that felt off.
Which is, now that I think about it, exactly what I help founders do with their customers.
If your profile — or your positioning — has been through a few different jobs, I'd love to hear what you've kept and what you've cut.
Skipper Chong Warson
Only humans buy anything, stop building for the wrong customer
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If you're not sure which customers are sticking around and why — that's exactly what we figure out together. Book an intro call at: howthisworks.co/start