Master Big Projects with Ease: A Simple, Effective Planning Strategy

Today we’re diving into something I know so many of you struggle with – planning and executing those big, scary projects without feeling completely overwhelmed. You know what I’m talking about, right? Those projects that make you excited but also make your heart race a little faster because they seem so enormous.

And let me tell you, I’ve been exactly where you are. In fact, I’m embarking on a big, scary project myself – creating and launching 30 podcast episodes in 30 days! Yes, you heard that right – this is day one of that journey!

I know, it sounds crazy, right?

But stick with me, because I’m going to share exactly how I planned this massive undertaking, and more importantly, how you can apply these same strategies to any big project you’re dreaming about. Think of this as your behind-the-scenes look at how I prepared for this challenge.

Before we dive in, I want you to think about a project you’ve been putting off. Maybe it’s launching that course you’ve been dreaming about, writing your book, or completely overhauling your business systems.

Whatever it is, keep it in mind as we work through today’s episode, because I’m going to give you the exact framework I use to turn those overwhelming projects into manageable, achievable goals.

The idea for my 30-day podcast challenge actually came from my experience with NaNoWriMo a few years ago. And for those who aren’t familiar, that stands for National Novel Writing Month and it’s when you write a novel in a month – we’re talking 30,000 words!

NanoWriMo takes place every year in November and so I was thinking about participating again, but I wanted to do something a little different. I didn’t want to write a book, but I wanted to do some kind of content project.

And around the same time, I was thinking about this, I was doing yoga one day and the yoga channel I watch on YouTube does these 30-day yoga journeys. And I thought, hey, what about a 30-day podcast journey?

So here we are.

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Prefer to listen? Check out episode 20 of the podcast: How to Plan and Execute a Big Project Without Feeling Overwhelmed

Planning and Preparation

I knew that if I wanted to pull this off, I would need to be super intentional about how I approached it. So, I made some key decisions upfront: I decided to keep the episodes shorter, about 10-15 minutes each instead of my usual 20-25 minutes.

I also chose to spend the month of October on prep work, rather than creating any new content. That’s something that came out of my NanoWriMo experience. They call in Preptober.

Let me tell you why this prep phase is so crucial. When you’re doing something as intense as creating daily long-form content, you can’t afford to waste time wondering what to do next or getting stuck in decision fatigue. Every minute counts.

So, I used the resources from my Content Planning Toolkit and tweaked them a bit for this challenge.

Supercharge your content strategy and achieve your business goals with our Content Planning Toolkit - the must-have tool for female solopreneurs.

I also know myself well enough to recognize my tendency to overthink things. So, I brainstormed a list of all the places I tend to get stuck in overthinking or perfectionism and I tackled as many of them as possible during the prep month.

This list included things like:

Outlines – I batched all the outlines in two sittings. I gave myself a time limit to get them all done in 2 hours.
Titles – I wrote all the titles in one batch (this was after I had outlines in place).
Deciding what kind of Instagram posts to share. now that may not seem like a big deal, but it’s a task where I often get stuck. So, I just went ahead and made those decisions and wrote them down. And I don’t have to think about that again.

This was honestly really good because I didn’t allow my perfectionist brain to take over. I gave myself permission to be imperfect throughout this project.

Related post: Overthinking Your Content Strategy?

Common Mistakes

Before we dive into the how-to, let’s talk about two major pitfalls that can derail even the most exciting projects.

The first one is under-planning. You know that saying from Ben Franklin, “if you fail to plan, you are planning to fail”?

It’s so true! I see this all the time with my students – they get so excited about an idea that they just jump right in. And while that enthusiasm is great, without proper planning, you might suddenly realize the project is way bigger or more complex than you thought. That’s when overwhelm kicks in, and projects end up abandoned.

Let me share a quick story about this. Last year, one of my students in my content planning course came to me super excited about launching a membership site. She had the passion, the expertise, and even some content ready to go.

But she jumped in without really planning the tech setup or content delivery schedule. Three months in, she was completely overwhelmed trying to manage all the things – the tech, create content, and serve her members all at once.

She reached out to me for advice, and I suggested she pause everything and create a proper project plan – which actually saved her time in the long run!

But here’s the flip side – and I’ve totally been guilty of this one – over-planning can be just as problematic. You can get so caught up in making everything perfect that you never actually start. Or you don’t even have time to start. You plan everything down to the tiniest detail, only to have circumstances change, forcing you to waste time replanning everything.

The Solution: Phase-Based Planning

So, what’s the sweet spot? I’ve found that breaking any big project into distinct phases is super helpful. Let me walk you through each phase and show you exactly how I applied this to my 30-day podcast challenge.

Phase 1: Brainstorming

This is where you let your creativity run wild! For my podcast project, I created a high-level content map spreadsheet. I reviewed all my existing blog posts for potential repurposing opportunities – that was the low-hanging fruit. The key here is to write everything down. Don’t judge your ideas yet; just get them all out.

During this phase for my 30-day challenge, I also generated a 52-week content plan from Marketing Magic, which is one of my favorite AI tools. The 52-week content plan helped me fill in the gaps and create a well-rounded plan for 30 episodes that covers all my content pillars.

But here’s what really made the brainstorming phase so powerful: I didn’t just think about content. I thought about all the potential roadblocks and challenges too.

What if I got sick? What if my mic broke? What if I ran into issues with my editing software?

And since this is November, what will I do for Thanksgiving? Because, I don’t want to have to worry about creating an episode on Thanksgiving Day. So, I pre-planned, what am I going to do about that?

This might sound negative but trust me – acknowledging and planning for potential problems actually reduces anxiety and makes you more confident in your plan.

Phase 2: Research & Decision Making

This is the phase most people skip, but it’s actually crucial! For my project, I:

Reviewed my existing podcast metrics to understand what resonates with my audience
Created a modified workflow template specifically for these shorter episodes. And I really streamlined and cut out all of the extras and the nice to-dos.
Analyzed my best-performing content to identify patterns and themes

However, this phase isn’t just about gathering information – it’s about making informed decisions. For example, my research showed that my audience particularly loves episodes that combine practical tips with personal stories. This insight shaped how I structured the outlines for each of the 30 episodes.

Here’s a pro tip: Use your research & decision-making phase to create what I call “decision filters.” These are criteria that help you make quick decisions later in the project.

For my podcast challenge, I created three specific decision filters. First, “Does this content fill gaps in my existing inventory?” This is going to help me fill out pillars that are a little light.

Second, “Does this content relate well to my paid offers?” Because let’s be honest – we’re running businesses here!

And third, “Can I create this content quickly without extensive episode-level research?” This will be crucial for maintaining the daily pace of the challenge.

Having these clear filters made it so much easier to choose topics and it will enable me to stick to my production schedule.

Phase 3: Planning

This is where we get tactical, and I’m going to break it down into three key steps:

1. Break the Project into Milestones

For my podcast challenge, I created 30 content packs upfront – one for each episode. This took about 45 minutes total, but it will eliminate so much daily friction as I go through the next 30 days. Each content pack includes:

Episode outline
Meta information – like the episode number, target keyword, meta description for the show notes, that kind of information
Repurposing ideas for social media
The links to include in the show notes

And by the way, my content pack template is one of the tools included in my Content Planning Toolkit that I mentioned earlier.

2. Focus on One Milestone at a Time

I set up my project in chunks: project planning, content planning, admin setup, and batch creation of graphics. Each milestone had its own focus time, which prevented that overwhelming feeling of trying to juggle everything at once.

Here’s how I structured my milestones:

Week 1: Project planning
Week 2: Content planning and outline creation
Week 3: Admin setup & streamlining workflow
Week 4: Graphics for the show notes pages and for Pinterest and Instagram

3. Create Specific Action Steps

Instead of vague tasks like “prep podcast,” I broke everything down into super specific steps:

Create 30 Asana tasks (one per episode)
Set up 30 folder structures in Dropbox – this is tedious stuff that I could get out of they
Create all featured images in one Canva document
Draft standard AI prompts for show notes and social media
Pre-plan all social media posts
Create email announcement templates

The magic happens when you make these action steps so specific that there’s no room for confusion or procrastination. For example, instead of “create graphics,” my task read “Create 30 graphics using the featured image template in Canva.”

Phase 4: Execution

Now here’s the beautiful part about doing all this prep work – when it comes time to actually execute your project, it should feel almost effortless. I know that might sound pie in the sky but stay with me here!

When you’ve done the work upfront to create those clear action steps, set up your systems, and batched similar tasks together, execution becomes more about following your roadmap than making constant decisions.

Think about it like this – have you ever followed a recipe where you gathered and measured all your ingredients before starting to cook? That’s called mise en place in cooking, and it’s exactly what we’re doing here with project planning!

For my podcast challenge, execution looks like this: I open my computer each morning, check my content map for the day, and get straight to work. No wondering what I’m going to record, no scrambling to create graphics, no last-minute panic about show notes. Everything is templated, systematized, and ready to go.

My only job during execution is to show up and do the work, meaning record the episode, then edit and publish it. And then the follow-up steps of announcing it to my email list, posting on Instagram, sharing it with my private community, those types of things.

Execution (or as I like to say “working the plan”) is so much easier when you’re not also trying to make a thousand tiny decisions at the same time!

Here’s what makes execution smooth:

Every task is specific and actionable
Templates are ready to go
Graphics are pre-designed or even pre-created
Systems are set up and tested
Folders are organized and waiting
Promotional content is pre-planned

The key is to trust the process you’ve created. Yes, things might come up that require adjustments – that’s just life! But because you’ve done such thorough preparation, you have the mental space and energy to handle those curve balls when they come your way.

Action Steps for Your Project

Now, let me give you some concrete steps to tackle your next big project:

1. Start with Your Why

Write down your project’s purpose and how it aligns with your bigger goals. Keep this visible throughout the project (I like to add this as note in my Asana project).

Ask yourself:

How does this project serve my audience?
What problem does it solve?
How does it fit into my larger business vision?
What specific outcomes am I hoping to achieve?

2. Set Your Boundaries

Decide upfront what success looks like and what you won’t compromise on.

For me, an important boundary was not letting work on an episode carry over to the next day. Because I knew if I did let work carry over, I would not be able to keep up the pace of one episode per day. I would get behind and then I would just get completely overwhelmed.

Consider:

What are your non-negotiables?
What resources (time, money, energy) are you willing to invest?
What sacrifices are you not willing to make?
How will you maintain work-life balance during the project?

3. Create Your Project Framework

Break your project into major milestones
Assign rough deadlines to each milestone
Focus on one milestone at a time
Break each milestone into specific, actionable tasks
Create accountability checkpoints
And build in buffer time for unexpected challenges

4. Set Up Your Systems

Choose your project management tool (I use Asana)
Create templates for recurring tasks
Set up your folder structure to organize your project assets
Batch similar tasks together
Automate what you can
Document your processes as you go

5. Plan for Obstacles

Think about what might trip you up and plan solutions in advance. I mentioned earlier that I brainstormed a list of everything that tends to push me into overthinking and perfectionism. And I came up with a plan to deal with those areas ahead of time.

So, consider:

What are your typical stumbling blocks?
Where might you need help or support?
What backup plans should you have in place?
How will you handle unexpected setbacks?

Wrap Up: Big Project Planning Strategy

Remember, the goal isn’t perfect planning – it’s effective planning. You don’t need to have everything figured out before you start. What you need is a clear framework that gives you confidence and keeps you moving forward.

I want you to take action on this right away. Grab your notebook or open a new document and write down that big project you’ve been thinking about. Then, use the framework we discussed today to start breaking it down into phases and actionable steps.

And I’ve got something special for you! It’s my Project Plan Checklist, which will be super helpful, especially if you’re new to project planning. It will help you make sure you’ve covered all the bases. You can grab your copy below.

Free Project Plan Checklist

Remember, you don’t have to do this alone. Share your project plans with me over on Instagram @toniakendrick– I would love to see what you’re working on so that I can cheer you on!

Want to remember this for later? Save it to your favorite Pinterest board.