Summer Check-In: New Clients, Old Friends, AI Clones, and a Trip to Boston
It's mid-August and I realized I haven't come up for air in a while. So here's what's been happening at Anneomaly this summer, because honestly, it's been one of those stretches where every week feels like three weeks and simultaneously like it’s just been 3 hours… and I mean that in the best way. I think.
The Best Kind of New Client Is an Old One
One of my favorite things about being almost twenty years into this career is that people come back. This summer we've picked up several new engagements from clients and colleagues I've worked with in past lives. People I haven't talked to in years reaching out and saying "hey, we need HubSpot help, and I remembered you."
That never gets old. And it's a good reminder that the relationships you build along the way matter more than any marketing strategy. Some of these folks knew me before Anneomaly existed. They knew me when I was figuring things out, making mistakes, learning the world in real time. And they still called.
We've also reconnected with a few past colleagues who moved to new companies and brought us with them. That's the kind of referral you can't make up. Someone changes jobs, pops up somewhere new, and one of their first moves is "let me call Anne." I don't take that lightly - I take it happily! I love it.
Boston for Business (And a Little Bit of History)
We took a long weekend trip to Boston this past weekend. Part client work, part sightseeing. We had a few meetings scheduled, which gave me the excuse to extend the trip and spend some time exploring.
We did all the things - the Tea Party Museum, the Freedom Trail tour, pizza and cannolis in the North End, and of course a Ghosts and Graveyards tour. Museums, events, exhibits... I'm a sucker for that stuff. Walking the Freedom Trail while also checking emails between meetings is peak "small business owner on vacation" energy - (Shannon - email me back about scheduling that lead scoring review!) You're never fully off, but you're also eating lobster bisque and reading about the Boston Tea Party, so it balances out. Oh, also, the new rain coat I got for the trip? Apparently a windbreaker technically, and was water resistant… not water repellant. See all of my pictures on my Instagram - @anneomalyanne
It was a nice change of scenery and a good excuse to turn a couple of client calls into a long weekend. Sometimes you just need to get out of your home office for a few days, even if the work follows you.
Building a Freelancer Course
This one has been simmering for a while, and this summer I finally put real time into it.
I've spent the last few months building a course for people who want to freelance in the HubSpot and marketing ops space. Not just "here's how to set up a profile on Upwork" (though we cover that). The real stuff. How to find your niche. How to position yourself. How to get clients. How to scope work. How to bill. How to deliver. How to handle the parts of freelancing that nobody talks about, like what to do when a client ghosts you mid-project or how to raise your rates without losing your mind.
I've been doing this for over a decade, and I've made every mistake. I've undercharged. I've overdelivered to the point of burning out. I've said yes to projects I should have said no to. I've also built something I'm really proud of. And I want to help other people do the same thing without the years of trial and error.
More on this soon. But it's been one of the most rewarding things I've worked on this year.
AI Video: Meet Edgar Anne
Okay, this one is fun. And weird. And I'm still not sure how I feel about it.
I've been experimenting with AI video generators to create talking-head style videos. The idea was simple: I want to put out more video content, but between client work, the course, and running the business, sitting down to record, edit, and produce videos just wasn't happening. The time commitment is real. Lighting, sound, editing, re-recording because you said "um" fourteen times, or LIKE, because I’m that age of millennial... it's a lot.
So I started playing with AI-generated versions of myself. And I've been calling them Edgar Anne. If you've seen Men in Black, you know the scene. The alien wearing Edgar's skin like a suit, not quite right, a little uncanny, but technically functional. That's Edgar Anne.
Some of the outputs are surprisingly good. Some of them are... deeply unsettling. The technology is impressive and improving fast, but I'm genuinely on the fence about whether it's right for our brand. There's something about authenticity and real human connection that's core to how we work. An AI version of me delivering a HubSpot tip might be efficient, but does it feel like Anneomaly? I don't know yet.
I'm still experimenting. I'll share more as I figure out where I land on this. But if you ever see a video of me and my mouth is moving slightly wrong, just know... that's Edgar Anne. Not me. Probably.
Helping Cecilia Launch Her Book
One of the coolest projects this summer was working with Cecilia Lynch to promote her new book, Stop Solving Problems: The Strategic Thinking System for Leaders at Every Level.
If you're an ops or sales leader (which, if you're reading this, you probably are), this book will make you uncomfortable in the best way. Cecilia's core premise is that the skills that made you successful, being responsive, being fast, being the person who fixes things, are the same skills that can keep you stuck.
She calls it the Tactical Thinking Trap. And there are four versions of it: Urgency Addiction (your calendar has no white space and you mistake speed for progress), Competitor Mimicry (someone else's moves are writing your strategy), Customer Request Fulfillment (you're solving the stated problem brilliantly but it's the wrong problem), and Problem-Focused Identity (fixing things is who you are, so the problems never quite go away permanently).
I read the first two chapters and immediately recognized myself in at least two of those traps. Urgency Addiction, for sure. And probably a little Problem-Focused Identity, because let's be honest, I love being the person who fixes things. That's literally the business.
But Cecilia's point isn't that problem-solving is bad. It's that when it's the only mode you have, you never get to the strategic work that would prevent the problems in the first place. That hit home.
If you're a leader who feels like you're working harder than ever but the same issues keep coming back, check out the book. It's worth your time. And Cecilia is brilliant. Working with her on the launch has been one of the highlights of the summer.
What's Next
The rest of the summer is full. Client work across the portfolio, more progress on the freelancer course, continued Edgar Anne experiments (send help), and probably another blog or two about the HubSpot updates that keep rolling in.
If you've made it this far, thanks for reading. I know these personal updates aren't everyone's thing, but I think there's value in showing what it actually looks like to run a small consulting firm. It's not all dashboards and workflows. Sometimes it's lobster rolls in Boston and arguing with an AI version of yourself about whether she blinks too much (or not enough - also, what is with the arm waving - do I wave my arms like that?!)
Happy summer.
Anne