In my experience, people easily fall into one of two camps. Those who dislike planning and jump into action as soon as possible, and those who love planning… a little too much.

I love planning, making lists, and organizing things. If you are anything like me, you enjoy thinking through every minute detail before starting a new personal project. The more complex the project, the better!

During the planning process, I can live out the entire project in my imagination. In planning, everything gets accomplished. Everything feels simple, linear, achievable, and exciting!

Planning is as fun as watching a movie where the heroine overcomes all obstacles and achieves her ultimate goal. She is beautiful and popular and does everything with ease. She effortlessly wins!

On the other hand, execution is not as sexy. Execution is disciplined and shows up consistently even after the initial excitement wears off. She requires overcoming resistance and navigating roadblocks.

Execution is the nerdy girl who is less popular because she skips parties to do her math homework. She is reliable and predictable. Others might call her a buzzkill because she always does the reasonable thing.

Planning Is Helpful When Used Right

Planning is a powerful tool that can help us manage personal projects, facilitate progress, and reduce stress. 

Planning helps us set appropriate goals, map out activities, coordinate our schedule, and ensure the optimal use of our resources (mainly time and money). 

The trick for making the most of this tool is to match the level of planning with the specific project at hand. Not every personal endeavor requires planning in the most minute details. 

Detailed planning can be beneficial for projects that are limited in scope. For example, planning out a busy afternoon – where you have to run multiple errands, make dinner, and finalize a PowerPoint presentation – is beneficial since you need to identify efficiencies and make time for everything.

Similarly, planning the details of your next house party can be very helpful. How many people do you expect? Will you order some catering or make the food yourself? Who is bringing what? You could always wing it, but there will likely be some planning around the details of the party.

For a small project like this, feel free to go all out. Plan the details. Diagram to your heart’s content, write a beautiful color-coordinated list, or build an exciting table in Excel (whatever floats your boat). 

Just remember that, while extremely fun, planning is only a tool, not the end goal.

Planning Can Be Too Much Fun (Beware)

For me, the planning process involves the following:

• Identifying all the steps I could think of.
• Figuring out the logical dependencies between various activities and their proper sequence.
• Imagining what it will feel like to reach the final outcome.

I make a lot of assumptions, romanticize the project, imagine the soundtrack playing in the background as I work through the plan, and fall in love with the much better version of me that will be crossing the finish line.

The planning process itself feels like an accomplishment. After a long session of planning the details of a new personal project, I need a cigarette. (Now, keep in mind that I don’t smoke. This is just a visual I have internalized from Hollywood movies.)

Throw in some free-hand diagramming with neat arrows and shapes or an exciting tabular representation of project tasks for peak enjoyment. Color-coded, please!

It doesn’t get any better than this. It is as intoxicating as sniffing the inside of a new book.

The Lure of Overplanning (Procrastination)

While planning is an important step, it means nothing if you don’t execute. It is easy to hide behind planning and use it as a form of procrastination. Obviously, you never get the desired result if you never do the work.

Overly detailed planning becomes an issue when working on a long-term project (that will take several days, weeks, or months to accomplish). This is especially true if the project has a certain level of complexity or considerable scope.

In this case, planning everything at once is usually detrimental. That’s because a complex project over a longer timeframe will have a lot of unknowns that are frankly unknowable until you actually start doing the work.

Any time you plan something new, you make assumptions about how things will go. Later, when you are in the trenches, some assumptions turn out to be false.

In the planning stage, you don’t know what you don’t know. This means that your attempts to lay out every single step are pointless. You need to remain flexible and be prepared to have your assumptions challenged.

Planning Through Progressive Elaboration

So how do you plan for a more complex personal project? You do it iteratively using progressive elaboration.

“Progressive elaboration involves continuously improving and detailing a plan as more detailed and specific information and more accurate estimates become available.”

(ProjectManagement.Com)

Here is how to use progressive elaboration for your personal projects:

1. Clarify the vision for your project.

Start with a high-level view of where you are now (current state) and where you want to be when the project is over (desired future state). What will success look like?

2. Identify milestones to reach along the way.

Assign a reasonable timeline to each milestone. The milestones will also serve as checkpoints where you assess your progress and evaluate whether you are moving in the right direction.

3. Plan details towards the first milestone.

Once you have the broad picture outlined, do more detailed planning focusing on the project’s first leg (up until the first milestone). If you need to chunk this first leg into sub-milestones, do it. Work through the details that will go into reaching the first sub-milestone.

4. Schedule a checkpoint.

Decide when to have your first touchpoint or review session, and put it on your calendar. That’s it! That is all the planning you need at this point.

5. Start doing the work.

Now get started on execution. As you work towards the first (sub)milestone, you will learn more about the project constraints, discover unforeseen challenges, learn what works and what doesn’t, and maybe even find that some tasks are easier than anticipated.

6. Review your progress.

When you reach the first checkpoint, review what has gone well and what has not. Does your end goal still feel doable? Is the project timeline still reasonable?

7. Repeat steps 2 through 6.

Adjust your original plan as needed based on the checkpoint. Plan the details of the next leg of your project. Execute. Review.

How to Know You Have Planned Enough

If you still feel unsure about when to move from planning to doing, here is a short list to keep you on track. Start executing your plan once:

• You have a high-level understanding of where you are headed (vision).
• You have identified milestones to help you move towards the big goal.
• You are clear on the very next steps to take.
• You have scheduled a touchpoint to evaluate your progress.

I find that this is just enough planning to get moving on your project. You have a clear direction and enough of a roadmap to know that you are on the right path. You know enough to move forward.

Take action as soon as you know what to do next. Keep going until you have reached the first milestone or touchpoint.

And once you have evaluated your progress thus far and made the necessary adjustments, plan the next chunk of your project.

Rinse and repeat until the project is done.

Happy planning to you, and may the odds be in your favor!

Disclaimer: Progressive elaboration is a concept I borrowed for the discipline of Project Management. I am a certified Project Management Professional through the Project Management Institute.