It’s Wednesday afternoon—the gravitational center of the workweek, where caffeine meets the existential murmur of "What exactly am I doing with my life?"
Today I want to talk about 2025 planning—for your clients, your business, and yourself.
There’s a duality to everything we do: working in and working on. It’s true for your business, your career, your personal growth—even your relationships. Working in is the grind—the endless email chains, Slack messages, and urgent-but-not-important fires that consume your day. But working on? That’s the architecture. The strategy. The long, quiet hours of thought that actually shape the future.
Both are necessary. One keeps the wheels turning; the other decides where the car is going.
The trouble comes when we confuse busyness with productivity. Being stretched thin isn’t a badge of honor if it means you’re sprinting in circles.
So, as we barrel toward the end of the year—and the symbolic turning of the page—it’s the perfect time to ask yourself some uncomfortable questions:
- What have I been building?
- Have I been moving toward my goals, or am I just holding things together?
- What’s the vision?
If you’re waiting until January 1 to start thinking about these questions, you’re already behind.
At AdVenture Media and AdVenture Academy, we’ve spent the past few weeks neck-deep in our own reckoning. We’ve been dissecting everything—the wins, the misses, the moments that felt electric, and the ones that drained the life out of us. When were we moving the needle? When were we just busy?
What’s fascinating is how clarity emerges from this process. Patterns surface. Weaknesses become opportunities. Strengths become systems. And if you allow yourself to dig deep enough, you’ll see not just where you’ve been—but where you could go.
The thing is, this isn’t just an intellectual exercise. It’s personal. It’s reflective. And if it’s done right, it’s transformative.
Close your eyes for a moment. Picture the person you want to become—not in a vague, motivational-poster kind of way, but in the details. How do they think? What habits define their days? How do they show up in the world?
Meditation on this vision is a necessary first step—but then you have to do the most paradoxical next exercise. Once you’ve imagined this future self, you need to ask yourself, what is the smallest possible step I can take to get there?
Maybe it’s committing to one dumbbell curl five times a week. Maybe it's emailing one client a week just a small token of thank you. These are the steps so small they barely register. No one will cheer you on, and there’s no immediate satisfaction to be found. And yet, this is the hardest part: lowering the bar so far that success is inevitable—yet unremarkable.
Because incremental progress compounds. One small step becomes two, then ten, then a habit, then a foundation. The person you want to be doesn’t emerge from massive, unsustainable effort. They emerge from showing up in ways that feel almost too small to matter—but matter more than you can imagine.
Here’s how we’re doing it: Ahead of our annual planning meeting, every member of our team is mapping out their own 2024 in two dimensions: the work they did and the work they want to do. Strengths. Weaknesses. Highs. Lows. The projects that lit them up and the ones that drained them. We’re bringing it all to the table—not just for ourselves but for each other.
And this is where the magic happens: in collaboration. There’s something uniquely powerful about aligning not just around goals but around meaning. Why are we doing this? Why does it matter?
So here’s my challenge to you: Take this week to do the same. Map out your year, not as a laundry list of tasks but as a narrative. What did you build? What did you learn? And most importantly, what do you want to create next?
I’ll leave you with this:
“You’ll never get anywhere if you don’t know where you’re going.”
Simple. True. And worth thinking about.
Let’s not wait until the calendar flips. Let’s start now.
For the rest of this week’s Windup, I’ll be walking you through three things: how I accidentally torched the bridge with Jordan Peterson (yes, that Jordan Peterson), why you absolutely need to grab free access to the Year-in-Review + 2025 Planning Template, and a few thoughts on closing out the year—because, as a deeply sentimental, goal-obsessed human being, I have entirely too much to say about it.
“Begin with the end in mind.”
— Stephen R. Covey (one of my favorite authors)
Rules for Life
A story from inside the agency...
I sometimes repeat some version of “Listen to people as if they have something worth saying.” I didn’t make that up. It’s Jordan Peterson’s ninth rule in his book 12 RULES FOR LIFE. The official rule is, “Assume that the person you are listening to might know something you don’t.”
The book has sold over 10 million copies and was among Amazon’s top 10 selling books in multiple markets every week for well over a year. To promote the book, Peterson embarked on a world tour, speaking to sold-out crowds, including at the Rosewood Ballroom, a 7,000-seat hall where the Dave Matthews Band launched one of their new studio albums. Considering Jordan Peterson is an aging psychologist in a three-piece suit and not one of the hottest rock and roll bands from the last decade, that’s pretty nuts. Peterson’s YouTube videos have been viewed billions of times, documentary films have been made about this life, and the NYT has called him one of the most influential and important thinkers alive today.
His insights into one’s relationship with themselves, and with others, have had a profound impact on my marriage and my parenting. He has helped me understand, and express, what it means to take responsibility—for myself and for others. I have so many questions I’d love the opportunity to ask him—and I’d pay good money for the chance to speak to him one on one. Many people who follow his lectures and teachings feel the same way.
Here’s the thing. I used to speak with Jordan Peterson twice a week.
Each call lasted forty-five minutes. He was one of my first clients. Jordan stumbled upon my AdWords YouTube tutorial and called for my help promoting his Self Authoring product. If you have any interest in journaling or figuring out where you’ve been, where you are, and where you want to go in life, I encourage you to check it out.Of course, this was all before Peterson was famous. To me, he was just another client I had to get through a bi-weekly call with. At the time, I was sleeping 2-4 hours a night, working on client campaigns, working on my own content, working on finding new business, and so on. I was always tired, but that didn’t really matter. If I had listened … or bothered to look up Peterson’s YouTube lectures—of which there were plenty, even back then—perhaps I wouldn’t have blown the opportunity.
When he came to New York, Frayde and I went to hear him speak at the Rosewood Ballroom. The lines to get in stretched around six city blocks. We paid the extra $150 for VIP seats, which included a photo-op and a meet and greet after the lecture. I shook his hand and told him that I used to manage his AdWords account and that we spoke twice a week over the phone for six months or so. He looked at me with compassionate eyes, like I was another fanatic in need of some encouragement (and willing to lie to get some), and said, “Oh, that’s nice.”
“No, for real,” I said. “I still have your PayPal login and password.” (this is true, by the way.)
He smiled wanly, and then security was kindly helping me find the exit.It’s unbelievably hard to do, and do consistently, but it’s worth practicing Rule Nine: Assume that the person you are listening to might know something you don’t.
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As the Year Ends, One Question Matters: Are You the Partner They Trust for 2025?
There are countless reasons why a brand decides to make a change. The most obvious—and most common—is poor performance. Maybe the last agency or freelancer was out of their depth, fumbling key strategies, or outright mismanaging the account. Other times, it’s not about numbers but the relationship: a sense that the agency has grown complacent, stopped innovating, and is simply coasting on autopilot.
In most cases, it’s not a single issue but a constellation of grievances orbiting around one undeniable truth: the client isn’t happy. They’re frustrated, disillusioned, and increasingly convinced that someone else could take the reins and steer their business toward better results.
Here’s where the real work begins: listening. Not just nodding along in a kickoff call, but really understanding the unspoken motivations behind their decision. It’s about uncovering what makes them tick, what keeps them up at night, and what they truly value in a partnership. Prove to them—every single day—that their trust isn’t misplaced. Show them that you’re relentless, thorough, and completely invested in their success. That you’re not just “in the account,” but that you’re in their corner (and on their account), leaving no angle unexplored and no opportunity untapped.
Now, here’s the thing most people miss: brands don’t just want the agency with the best performance; they want the agency they believe can deliver the best performance. There’s a world of difference. Hitting ROAS targets isn’t a guarantee of security—because if the client suspects they could do better with someone else, the relationship is already on thin ice.
Conversely, poor performance doesn’t necessarily mean you’ll lose the account—so long as the client believes in you. They need to see that you’re capable of navigating the challenges and turning the ship around. This industry isn’t built on performance alone; it’s built on trust. Earning it. Maintaining it. Proving, over and over, that you’re the best partner they could possibly have.
And yet, somehow, most people manage to screw that up. That’s usually when the client picks up the phone—and calls us.
So, as you reflect on this, think about it in the context of your bosses, your clients, your team, and your customers—and let this perspective shape the way you approach your 2025 planning.
For a comprehensive approach to 2025 media planning, I highly recommend Nechama Teigman's Strategy Lab. This course offers in-depth guidance on setting clear goals, developing effective media plans, budgeting, and effectively communicating strategies to stakeholders. If you have The Ultimate Digital Advertising Library (AKA: the All-Access Pass), it's already in your library. Just log in to access it here.
Isaac Rudansky
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