The Creator's Guide to Annual Planning: Lessons from a Million-Dollar Creator Business

Last week on Creator Toolbox, Colin (my co-host and founder of The Podcast Host and Alitu) walked me through his annual planning system. I was so impressed that I told him I'd go back and take notes - and I figured I might as well share those notes with you too.

Colin's been refining this approach since 2015, when he first started The Podcast Host, which would transform from "just a blog" into a seven-figure creator business in 2025. What started as a simple planning exercise has evolved into a comprehensive system that now helps guide our entire company.

I'm implementing this system myself right now, so let me break down how it works and how you can apply it to your own creator business.

Rather listen? Here's the episode!

Start With Weekly Reflection

The foundation of Colin's approach is deceptively simple: weekly reflection.

"I spend an hour every Monday morning thinking about my week ahead and the week just gone," he told me. "I write a little journal entry - it doesn't need to be fancy or big, sometimes it's just a couple of sentences."

What's fascinating is how these quick entries become invaluable over time. I've often struggled to remember what happened even a month ago, let alone track patterns over a year. This simple habit solves that problem.

The Annual Review Process

When December rolls around, here's how to turn those weekly reflections into a proper annual review:

Step 1: Review Your Weekly Entries

The magic happens when you read through your entire year of reflections in one sitting. Patterns emerge that you'd never notice in the day-to-day grind.

Colin shared a perfect example from his recent review: "I realized I was just not managing my Asana in any way the right way. I mentioned this a bunch of times, like maybe five to 10 times during the year... looking back, I remember myself dragging tasks from one week to the next constantly in Asana the whole time."

That insight led him to completely redesign his task management system for 2024. Here's how he's restructuring it:

• Calendar view with only 1-2 realistic tasks per day (no more overloading)
• A separate space for new ideas and inspiration
• A backlog for less important but still valuable items
• Weekly review of the ideas inbox
• Monthly review of the backlog to resurface important items

"I'm going to have different space for ideas, essentially," Colin explained. "And my calendar in Asana, my calendar view is gonna only contain very realistically one or two tasks per day. And they are the most important tasks of that day."

It's exactly the kind of practical improvement that's hard to spot when you're in the thick of things. Without the annual review process, that pattern of constantly moving tasks might have continued indefinitely.

Step 2: The Big Questions

Next, Colin uses a set of reflection questions that cut right to the heart of your year. These are an updated version of the questions Colin read out from an old annual review:

1. What major themes or patterns kept coming up?
2. What accomplishments are you most proud of?
3. What were the failures, mistakes or disappointments you experienced?
4. What good things do you think were missing from last year?
5. What not-so-good things were there too much of last year?
6. What are your big lessons or new principles taken from reflecting on last year?

I particularly love that second question about acknowledging your accomplishments. As creators, we're often so focused on what's next that we forget to recognize our own achievements.

Step 3: The Yes/No Lists

This next part comes from Colin's experience with the Fizzle community (shoutout to Caleb Wojcik, now CEO of SPI). Create two crucial lists:

1. Things to Say Yes To: Activities and opportunities you want to embrace
2. Things to Say No To: Areas where you need to set boundaries

Colin gave a great example in our chat: "I'm going to say yes to more speaking engagements this year. But equally, I know that actually going to events is draining for me and it takes too much time and too much money. So I'm going to say no to in-person events and I'm only going to do virtual ones."

These lists become your decision-making framework for the year ahead. When new opportunities arise, you can quickly check if they align with your "yes" list or belong in the "no" category.

Step 4: The 80/20 Analysis

This part comes from Tim Ferriss, and it's all about identifying what really moves the needle:

• What 20% of activities, experiences, or people caused 80% of your negative emotions or outcomes?
• What 20% of activities, experiences, or people produced 80% of your most positive emotions and outcomes?

Planning the Year Ahead

Now comes the fun part - looking forward. Here's how Colin approaches it:

Step 1: Set Your Themes

Rather than jumping straight to goals, start with themes. What do you want this year to be about?

In my own planning session this week, I'm focusing on themes like:

• Creating more consistent, high-impact content
• Building stronger relationships with our community
• Developing new skills in video creation

Your themes might be completely different - that's the point. They should reflect your unique situation and aspirations.

Step 2: Create Aligned Goals

Under each theme, set specific goals. For example, under my "consistent content" theme:

• Publish two substantial pieces per week
• Create a content calendar one month in advance
• Develop a backlog of emergency content

Step 3: Schedule Review Points

This is crucial - and something Colin admits he missed last year: "I should have had in my calendar my quarterly or even six-monthly review."

Don't make the same mistake. Schedule your check-in points now:

• Monthly theme review
• Quarterly goal assessment
• Mid-year comprehensive review

Step 4: Make It Visible

"There's nothing beats having a bit of paper on the wall to really focus your thoughts and make sure you're reminded all the time," Colin insists. When we had our office in Dundee, the walls were covered with our goals and themes.

Working remotely now? Print it out and put it by your desk, or make it your desktop background. The key is keeping it visible.

Making It Work for Your Creator Business

One thing I love about Colin's system is how flexible it is. Whether you're a solo creator or building a team, these principles can adapt to your needs. The key is consistency in reflection and regular review.

A final insight from Colin about the personal/professional balance: it changes as your business grows. When he was a solo creator, everything was integrated. Personal goals like taking a mid-week cycling break sat alongside content creation targets - because what's the point of being your own boss if you can't enjoy the flexibility?

But as our team has grown, the planning process has evolved. Company-wide goals and planning now happen separately with the team. "Anything that involves the team is part of the company planning process," Colin explains. "And anything that is literally just stuff work that I do personally goes into my personal planning."

For most creators starting out though, keeping it all together makes sense. Your creator business is deeply personal - embrace that in your planning.

Ready to put this into practice? Start with that weekly review habit. It's the foundation everything else builds upon. Remember, the goal isn't perfection - it's progress. Take what works from this system and make it your own.

And if you're looking for more insights into building and running a creator business, join Colin and me every week on the Creator Toolbox podcast. We're sharing everything we learn as we build, so you can do the same.