Affiliate marketing is a wild ride, isn’t it? Some days, you’re the genius matchmaker connecting brands and consumers; other days, you’re staring at spreadsheets wondering if you accidentally became an accountant. And then, looming in the distance, there’s annual planning. Look, I get it. Mapping out an entire year sounds about as fun as alphabetizing your receipts. But here’s the kicker—it makes everything better. Trust me, I’ve seen it.
When I sat down to chat with affiliate marketing guru Will Gaines, we didn’t just talk about planning—we tackled it. Will’s got over 15 years of experience making affiliate marketing look easy (spoiler alert: it’s never easy), and he shared how using a tool called the wheel marketing calendar can totally transform the game. This calendar isn’t just about dates; it’s about strategy, creativity, and, dare I say, avoiding those heart-stopping “Oh no, we forgot about Black Friday!” moments.
If the thought of planning makes you break out in a cold sweat, you’re not alone. But what if I told you it could actually be fun? Or at least, more fun than sorting socks? Stick around and find out why planning smarter might just become your new favorite hack.
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What is a Wheel Marketing Calendar?
When it comes to annual planning, the concept of a wheel marketing calendar stands out as a game-changer. This tool isn’t just a schedule—it’s a vision. It helps marketers map out the year ahead by proactively identifying critical dates, holidays, and market opportunities. Whether you’re leveraging well-known shopping events or inventing your own brand-specific campaigns, the wheel calendar is about staying ahead and leading with intention. It ensures your strategies are powered by data and creativity, not last-minute scrambling.
Meet Will Gaines

For those who haven’t met him yet, Will Gaines is a force to be reckoned with in the affiliate marketing world. With over 15 years of expertise, he started his career as an analyst before stepping into the role of a freelance consultant. Will specializes in building agile affiliate strategies and has a knack for breathing life into complex concepts. His true passion? Making organization and strategic planning accessible—and even exciting—for marketers.
How to Make Wheel Marketing Calendar Planning Fun
Rather than being a dreaded task, annual planning can become an exciting and invigorating process.
Here are Will’s top strategies for making it happen:
1. Harness Historical Data
Data is your best friend. Analyzing past performance isn’t just about looking back; it’s about predicting what’s ahead. Will recommends layering data from previous years to identify recurring patterns, peak seasons, and potential slowdowns. With this insight, you can time your campaigns for maximum impact and prepare creative solutions for sales dips.
2. Invent Unique Opportunities
Marketers often wait for industry-wide events to align campaigns, but why not create your own opportunities? Will shared how his team at WP Engine once invented a brand-specific holiday during a naturally slow season. This bold move not only boosted engagement, but it also showcased the power of innovative thinking in staying relevant year-round.
3. Collaborate Across Teams
Annual planning doesn’t happen in a vacuum. Will emphasized the importance of working across teams—like email marketing, content, or paid media—to combine talent and insights. This collaboration ensures your campaigns are cohesive and far-reaching, enhancing their chance of success.
4. Showcase Leadership Skills
Stepping up during the planning process is an excellent way to demonstrate leadership. By taking initiative, aligning goals, and presenting well-thought-out strategies, you position yourself as more than an affiliate manager—you become a strategic leader within your company.
5. Learn Through Experimentation
Every plan has its share of triumphs and flops. Will reminded us that failures aren’t setbacks; they’re lessons. Experimenting with bold ideas, even if they don’t always hit the mark, increases your creative arsenal and prepares you for future success. Every misstep is an opportunity to grow.
5 Major Takeaways from the Podcast

If you’re on a mission to master your annual planning, here are the top lessons from my chat with Will that you won’t want to miss:
💡 The Power of Planning Ahead: Start early and set your sights on key dates, trends, and opportunities for the year.
💡 Data-Driven Decision-Making: Use historical trends not just to analyze, but to anticipate and prepare for what's next.
💡 Creativity Differentiates You: Invent distinctive promotional events that will help your brand stand apart from competitors.
💡 Teamwork Amplifies Impact: Collaborating with other marketing departments leads to more robust, comprehensive campaigns.
💡 Be Proactive, Not Passive: Taking the lead in planning signals that you’re a visionary, invested in the company’s success.
Wheel marketing calendar episode wrap-up.
Annual planning doesn’t have to feel like a chore. Seriously, it’s not just about filling out calendars and pretending you’ve got it all figured out. Will Gaines showed us that it’s about taking control, shaking things up, and laying the groundwork for campaigns that actually work—and maybe even earn you a few pats on the back. You’ve got the tools, the strategy, and the chance to set the tone for an amazing year. Why not take it?
Sure, the road to affiliate greatness has its potholes, but that’s where your creativity, teamwork, and a good dose of data come to the rescue. Whether you’re inventing a wild new holiday to boost sales or collaborating like a pro with other teams, you’ve got what it takes to make magic happen.
And hey, if planning still makes you cringe a little, just think of it this way—it’s way more exciting than tackling laundry day, and the payoff is a heck of a lot sweeter. Here’s to a year packed with clever ideas, standout strategies, and maybe even a little fun along the way. Go crush it—you’ve got this.
| Timestamp | Summary |
|---|---|
| 00:18 | Meet Will Gaines, an expert with insights on the wheel marketing calendar. |
| 01:23 | Discover Will Gaines’ expertise in affiliate marketing using the wheel marketing calendar. |
| 01:56 | Will dives into consulting and how the wheel marketing calendar drives strategy. |
| 02:39 | Why annual planning and the wheel marketing calendar are crucial for marketers. |
| 03:08 | Understand the essential components of a successful wheel marketing calendar strategy. |
| 05:22 | Learn the best timing to start your wheel marketing calendar planning process. |
| 06:56 | Strategies to inspire your team to adopt the wheel marketing calendar. |
| 07:16 | Analyze market cycles with the wheel marketing calendar to predict key trends. |
| 09:07 | Use data to enhance accuracy and effectiveness in your wheel marketing calendar. |
| 14:04 | Build content calendars using insights from the wheel marketing calendar. |
| 16:08 | How affiliate managers can show leadership through the wheel marketing calendar approach. |
| 18:35 | Keep your data organized for actionable results with the wheel marketing calendar |
| 20:51 | Learn from missteps to strengthen your future wheel marketing calendar campaigns. |
| 23:30 | Final reflections and ways to connect with Will Gaines about the wheel marketing calendar. |

Dustin Howes
AFFILIATE MARKETING CONSULTANT
Dustin Howes is a partnership nerd spreading the good word about performance marketing. He is the chief coach at performancemarketingmanager.com and is dedicated to helping companies grow their performance marketing channels. He also provides affiliate manager training and private consultations, helping companies find the right solution for their budget.
Find out more about Dustin here.






