Hey friend,
I just spent the last few weeks planning 2026, and honestly?
I started with this overwhelming feeling of "I need to do ALL THE THINGS" - grow the newsletter, scale the community, launch a video series, keep closing clients.
Everything felt equally important and equally urgent.
You, too?
Here's what actually helped me get clear, and what I'm betting might help you too as you plan your own year.
Problem: The Everything Trap
My initial brain dump looked like this:
- Newsletter needs to grow (but it feels all over the place)
- Community needs more structure (but I don't want to lose what makes it special)
- I want to double down on video (but I've only recently done it consistently)
- Oh, and I absolutely have to keep closing clients (because, you know, revenue)
All valid. All important. All completely paralyzing.
The breakthrough came when I stopped trying to plan everything at once and started asking better questions about each piece.
Process: One System at a Time
Instead of trying to solve "2026" as one big problem, I broke it down:
Newsletter first. The question wasn't "how do I grow my newsletter?" It was "what job should my newsletter actually do?"
Turns out I'd been trying to make it do three jobs: evergreen teaching, current events commentary, and behind-the-scenes interviews. No wonder it felt scattered.
The fix: Pick one premise. For me, that's showing how companies actually get customers.
And in between I’ll focus on my Content IP, "checkbox marketing,” and helping companies defeat it using my 5-step content framework.
My content shows it. Guest interviews show it. Everything ladders up to one clear idea.
Community second. Same approach. I wasn't asking "how do I grow ALL IN?" I was asking "what makes someone WANT to be part of ALL IN?"
The answer was… identity.
I don't join communities for perks. I join because membership says something about who I am.
So instead of adding more programming, we're doubling down on what already works: real conversations, members, and systems that let the community program/grow itself.
(Shoutout to Elfried Samba's work at Gymshark - his principle of "you are their identity" completely reframed how I think about community - you'd love his podcast)
Video third. This one's new for me. I've dabbled, but never committed.
~50k views in the past year across TikTok, YouTube and Reels.
Not bad.
But I want MORE.
The unlock was finding a format I actually WANT to do: short videos explaining sales psychology and cognitive biases. Each one follows the same structure and I just know these will crush.
What I Learned About Planning
1. Specificity beats ambition. "Grow the newsletter" is useless. "Ship 2 guest interviews per month + use my 5-step content framework" is a system I can actually run.
2. Ask different questions. Don't start with "what should I do?" Start with "what problem am I solving?" or "what job does this need to do?"
3. One thing feeds another. My newsletter interviews can become video clips. Community conversations surface newsletter topics. Video content builds authority that feeds client work. When things connect, growth gets easier.
4. Get help with the thinking. I used ChatGPT as a thinking partner through this entire process. Not to tell me what to do - to ask me better questions. The Socratic method works. Having something push back on your fuzzy thinking helps you get clear faster. Next step, share with friends (like you, reading this)
5. The unscalable stuff matters most. For the community, my "non-negotiables" are all manual: checking in with quiet members, connecting people who should meet, and personally welcoming new folks. That's what paid communities can't fake.
What's Actually Changing in 2026
Here's the short version:
Newsletter: One clear premise (how companies get customers), interviews with marketing leaders, no more roundups or news commentary. Success = more prospects citing "newsletter" as how they found me.
Community (ALL IN): Free and vetted, focused on identity over features, systems that run consistently instead of random event spikes. Success = members adding it to their LinkedIn profiles without me asking.
Video: Success = broad appeal AND building authority that ties back to what I actually sell.
Client Work (Content Strategy): Keep closing deals. Everything else supports this, but this is still what I love doing (and what pays the bills).
The Question I Keep Coming Back To
As you plan your 2026, here's the question that helped me most:
"What's the simplest version of this that would actually work?"
Not the impressive version. Not the version that looks good in a deck. The version you'd actually do every week without burning out.
Simple. Focused. Doable.
- Brendan
P.S. - If you want to see the full planning doc (including all the systems, flywheels, and growth levers), reply and let me know. Happy to share the behind-the-scenes.