19 DAYS AGO • 12 MIN READ

Why Most Planning Systems Fail (And How to Fix Yours)

profile

EVOLVEE

Join 200+ seekers on the path to inner growth, self-mastery, and purpose. Discover insights on manifestation, spirituality, and personal evolution every week.

Last week, we talked about deep work and time blocking, how to structure your day for focus and productivity.

But focus alone isn’t enough, you need to know exactly what to work on.

This week, we’re going deeper: how to plan your tasks effectively, eliminate overwhelm, and build a system that works for you.

Missed last week's newsletter? Read it here

“Most people feel best about their work the week before their vacation, but it's not because of the vacation itself. What do you do the last week before you leave on a big trip? You clean up, close up, clarify, and renegotiate all your agreements with yourself and others. I just suggest that you do this weekly instead of yearly.” - David Allen

Before a trip, you don’t just work, you wrap things up. You bring clarity to your tasks instead of leaving them scattered. That’s exactly what a good system should do daily and weekly, not just once a year.

I've always been a person who has a lot of ideas and things I want to do.

  • Build an app.
  • Writing online.
  • Create digital products.
  • Open a juice bar on the beach.
  • Invent a self-cleaning blender.

But having ideas isn’t the hard part.

The real challenge is making them happen. Most people never get further than just an idea in their head.

We all have ideas. And the difference between those who succeed and fail is simply one thing: action.

Most people spend more time thinking and talking about their idea rather than actually acting on it. I used to be like that.

I still go all over the place sometimes, but I always bring myself back to my plan and keep things simple, focusing on just a few projects and tasks at a time. That’s what actually moves things forward.

When you create a system, planning your week and days, you clean up a lot of mess in your head. Your mind doesn't have the capacity to store and remember everything. That’s why you need to wrap things up, clarify what matters, and make space, just like before a big trip.

That way, you’re not carrying unfinished tasks and random thoughts around all the time. You free up energy to actually move forward instead of just thinking about what needs to be done.

But even when you try to plan, it's easy to feel overwhelmed.

Too many tasks, no clear direction, before you know it, your to-do list becomes just another source of stress.

When Planning Becomes the Problem

It’s 6 AM. You wake up, do your morning routine, or just dive straight into coffee immediately.

You start your day motivated, get some work done. You might even implement time blocking and deep work for specific tasks like we discussed in last week's newsletter.

However, by 3 PM, you're drowning in unfinished work.

You’ve already completed a few tasks, but your to-do list is still stacked. You start feeling stressed, anxious, like you’re failing.

Five tasks left. Where do you even start?

You jump between them, trying to knock them out, but instead, you lose momentum.

The structure you started with in the morning? Gone.

Deep work and time blocking? Out the window.

Before you know it, you're scrolling TikTok and Instagram, avoiding the mess.

By the end of the day, you look back at your list, feeling like you worked all day yet accomplished nothing meaningful.

Most people struggle with planning because they overcomplicate it or don’t have a system.

Without a clear structure, you jump between tasks, never make real progress, and always feel behind.

And that feeling doesn’t just disappear.

The more unfinished tasks pile up, the more overwhelming it gets. You start second-guessing your priorities, constantly switching between what feels urgent and what actually matters.

Instead of working with clarity, you’re stuck in a cycle, one where the more you plan, the more chaotic things feel.

That’s when planning stops being useful and becomes just another form of procrastination.

When Planning Feels Like Another Job

Most people spend more time planning than actually doing.

Watching "I Tried 137 Productivity Tools. These Are The Best" on YouTube.

Tweaking their Notion setup for the 10th time this month.

Switching between planners, apps, and time management hacks.

I used to do the same thing.

I spent months jumping between different planning tools, hoping one would finally "fix" the chaos. But nothing stuck.

Because the problem wasn’t the system. It was the fact that I was always adjusting the system instead of actually doing the work.

Even when I got most things done, my mind was still racing.

At the gym. Out with friends. Sitting at a café, trying to enjoy a coffee.

The unfinished tasks never left me. My brain was still on.

I thought I needed a better system. A perfect system. But what I really needed was a way to shut off work at the end of the day.

If you’re here for The One Ultimate Planning Method™, you’re in the wrong place.

I can’t give you that. No one can.

Because everyone works differently.

But what I can give you is a clear, simple structure, one that actually works, without overcomplicating things.

Some days, I still don’t get everything done.

But the difference now? I don’t carry it with me. I’ve found a way to wrap up my day without feeling the weight of unfinished work.

I built my planning approach from people like Dan Koe and Cal Newport, refining it over time to fit my workflow.

And today, I’ll show you exactly how I remove the mess, minimize overthinking, and create space for real work without spending hours sorting my to-do list.

Why Your Planning System is Failing You (and How to Fix It)

"In character, in manners, in style, in all things, the supreme excellence is simplicity". - Henry Wadsworth Longfellow

I've been on this path of self-transformation, improvement and growth for a couple of years and one of the best things i've learned is to keep simplicity in mind with everything I do (except my goals and dreams, that where I go big).

Simplicity is especially powerful when it comes to planning.

It helps you to keep things clear, structured and easy to act upon.

Imagine packing for a trip.

You throw everything into your suitcase, just in case you need it. But when you arrive, it’s a mess. You can’t find what you need, everything is wrinkled, and you waste time searching through unnecessary stuff.

Now imagine packing light. Only the essentials. Everything fits, everything is accessible, and you move freely.

That’s what simple planning does, it keeps things clear, structured, and easy to act upon, instead of dragging extra weight with you.

Planning should be simple. But for most people, it’s just another layer of stress.

The Planning Trap: Why Most People Struggle with Planning

Most people think planning will solve their problems.

But in reality, planning itself often becomes the problem.

We overestimate how much we can get done.

We list 10 things for the day and feel confident we can finish them, only to end up with half-done tasks and growing stress.

Think about it.

How many times have you mapped out your time, feeling certain you could crush your to-do list, only to fall behind and wonder where the hours went?

I’ve been there.

For years, I thought planning was the answer.

If I could just get better at organizing my tasks, I’d be more productive. But instead, I kept drowning in unfinished work.

Planning felt like it was supposed to fix everything, but instead, it became another source of stress.

What if the problem isn’t planning itself, but the way we approach it?

That question changed everything for me.

About 1.5 years ago, I stumbled upon Dan Koe while searching for a better way to plan my projects. I wasn’t looking for another app or productivity hack, I was looking for something that actually worked.

And that’s when I realized: Planning isn’t meant to be a prison. It’s meant to be a safety net.

What I loved with Dans approach was that it felt so simple and easy.

In combination with looking into it even more, I also found out about Cal Newport, the planning and deep work guru.

That’s when I changed my approach. I stopped overcomplicating things and focused on a planning system that actually worked for me.

Here’s what I mean.

The Shift: Planning Should Be a Safety Net, Not a Jail Cell

As mentioned before, when planning, keep it simple.

You don’t want to trap yourself in a system that feels like a prison, but instead, make it easy to navigate, have clarity, and take action on tasks that matter most.

The fewer the tasks, the easier it is to execute.

Less doesn’t mean you won’t get things done. Keeping it simple reduces stress and boosts your self-esteem when you actually finish your list for the day and week.

If you have extra time left over? Great. Just pull in new tasks from next week’s list.

When I started implementing Dan’s planning system into my routine, it made a lot of sense.

  • You have a big goal (a project).
  • Assign it to a specific quarter.
  • Break it down into tasks for the next 3 months.
  • Each week, pick 1–2 tasks and work on them daily.

If you’re curious about this planning method, you can check out his Power Planner here (this isn’t an affiliate link, just sharing something that helped me gain clarity back in the day).

However, even though I see the value in this approach, it didn’t fully work for me.

Why?

Because my projects don’t always have a clear plan from the start. New tasks pop up along the way.

A lot of what I do is recurring, writing my newsletter, posting on X, working on a digital product. I don’t always know the exact steps ahead of time.

If your work is like this, where things change as you go, you’re better off focusing on weekly and daily goals instead of planning too far ahead.

That’s what I did.

But the main idea stays the same.

Why You Need a Trusted System

Our brains aren’t meant to store and organize tasks, they’re meant for creative problem-solving.

Mental clutter leads to stress, distraction, and decision fatigue. That’s why you need a trusted system to capture everything and organize it in a way that works for you.

Inside this system, you write down every task, idea, commitment, and project. You don’t have to overcomplicate it, just use whatever tool works best:

  • A physical notebook.
  • Apps like Notion, Trello, or a simple notes app.

The key is to get things out of your head and into a system.

Anything that stays in your mind creates stress and uncertainty.

For example, say a task pops up during the day, like sending an important email.

Instead of trying to remember it, you immediately write it down. Either act on it right away or sort it into your system to handle later.

Once I realized this, I stopped relying on my memory and started storing everything in a system.

Every task, idea, and commitment had its place. No more mental clutter, no more forgetting things.

Instead of carrying unfinished tasks in my head, I had a clear structure for capturing, organizing, and acting on them.

Now, let me show you exactly how to set this up.

The System: A Simple Planning Framework That Works

Before we get into the steps, I want to make one thing clear:

This isn’t about following a fixed system or making planning another thing to stress over.

It’s about making things easier. Giving yourself structure without overcomplicating it.

So as you go through this, take what fits and ignore the rest. The goal is to find a simple way to plan that actually works for you.

1) Organize Tasks by Projects (Create Your Lists)

Before you can plan, you need a clear overview of what needs to be done.

Instead of dumping everything into one big to-do list, organize your tasks by project.

Here’s how I do it:

Create a folder for each project.

For example, If you’re a entrepreneur, you might have folders like:

  • Digital Writing (Newsletter, X posts, Threads, etc.)
  • Product & Development (Design, Features, Marketing, etc.)
  • Self-Mastery & Learning (Personal Development, Health, etc.)
  • Other (Random life/work tasks that pop up).

Inside each project folder, list tasks in two categories:

  • Recurring tasks: Tasks you do on a regular basis (e.g., “Write X posts daily,” “1-hour deep work on the app”).
  • One-time tasks: Tasks that have to be done but aren’t recurring (e.g., “Fix landing page,” “Send email to dev team”).

This gives you a clear place to store all your tasks so they’re not just floating around in your head.

2) Plan Weekly by Pulling from Your Lists

Once your tasks are organized, it’s time to plan your week.

Every Sunday, review your task lists and decide:

  • Which recurring tasks will be done daily (already set).
  • Which new tasks should be done this week (pull from the project lists).
  • Prioritize based on urgency, deadlines, and importance.

Keep it simple:

  • Assign 1–2 key tasks per project per week.
  • If there’s extra time, pull from the list.
  • Don’t overload yourself, planning less means executing more.

Example:

  • Digital Writing: Write newsletter, 1 thread, daily X posts.
  • App Development: 1-hour deep work daily, update website, send outreach email.
  • Other: Renew passport, schedule a call with designer.

This keeps planning flexible while still giving you a clear roadmap.

3) Assign Tasks to Specific Days

Now that you know what needs to be done for the week, the next step is assigning tasks to specific days.

How to do it:

  • Every night (or morning), check your weekly plan and decide what to work on that day.
  • Recurring tasks are already scheduled.
  • For other tasks, assign them to a specific day (or leave them flexible if needed).

Example Daily Plan:

  • Monday: Write newsletter, X Posts, 1-hour deep work for app project, fix website bug.

If you want to know how to time block your days for better focus, check out last week’s newsletter here.

This helps you start every day with a clear plan instead of wasting time deciding what to do next.

4) Capture New Tasks as They Come In

This is the step that stops mental clutter.

Throughout the day, new tasks will pop up. Instead of trying to remember them, write them down immediately.

  • Create a capture folder or section (e.g., “Other” or “Inbox”).
  • Whenever something comes up, add it there.
  • At the end of the day, review and decide:
  • Do it today (if it takes less than 2 minutes).
  • Assign it to a specific day this week.
  • Move it to next week’s planning session.

Example:

  • Midday, you remember you need to email a client. Instead of stopping your work, add it to the capture list.
  • Later, during your planning review, you decide when to handle it.

This prevents you from constantly switching tasks and losing focus.

5) The Shutdown Ritual (End Your Workday with Clarity)

No matter how well you plan, some days will get messy.

You’ll overestimate how much you can do. Tasks will take longer than expected.

And that’s fine.

The most important thing isn’t to force everything into your schedule. It’s to avoid stressing over unfinished tasks and give yourself permission to shut down.

That’s where the Shutdown Ritual comes in, a concept I learned from Cal Newport.

It’s a simple way to wrap up your workday, clear your mind, and disconnect from work so you can actually enjoy your time off without carrying unfinished tasks in your head.

Here's how it works:

Step 1: Review Your Day & Sort Loose Tasks

At the end of your workday (for example, at 5 PM), go through your inbox, notes, and any new tasks that popped up.

  1. If something is quick (under 5 minutes), do it now.
  2. If it needs more time, schedule it for another day.

This ensures that nothing lingers in your mind. Everything is either completed or organized for later.

Step 2: Clean Up & Close Your Schedule

Once you’ve sorted tasks, acknowledge that your workday is done.

No more adding things to the list. No “just one more task.”

Give yourself mental closure by saying (or writing): "Shutdown complete."

Step 3: Make Room for Rest & Enjoyment

This is where most people get it wrong.

They finish work but still carry the stress with them. They check emails, think about unfinished tasks, and never fully switch off.

But when you intentionally close your workday, you create space for:

  • Spending time with family & friends.
  • Hitting the gym or going for a walk.
  • Enjoying hobbies, watching a show, or just doing nothing.

It’s about removing the pressure to always be working.

When you close your day with intention, you set yourself up for a stronger tomorrow.

By creating a simple system, capturing tasks as they come, and making space to actually rest, you remove the endless cycle of stress and unfinished work.

I’ve updated last week’s Deep Work + Time Blocking template with this simple planning structure. No fixed system, just inspiration to help you build your own.

Check out the template here: https://evolvee.kit.com/0ae32af7e4

See you next week.

That was it for today.

I hope you got value from this and, more importantly, that you actually try it out.

If this helped, let me know. And if you have any questions or insights, feel free to reply on email or DM for faster response on X (twitter.com/evolvee33), I read everything.

See you next week.

-Tomas

EVOLVEE

Join 200+ seekers on the path to inner growth, self-mastery, and purpose. Discover insights on manifestation, spirituality, and personal evolution every week.