Trying to craft the perfect plan is a fool’s errand. I hardly recommend it. For the most part, I say dive headfirst into the unknown and let things unfold naturally.
But let’s take a beat.
Because a little bit of planning usually does help, even for the most adventurous of adventurers.
The trick is balancing when you should think ahead and when you should stay flexible to see what happens.
This is the No Compass guide on how to get better at planning (without over-planning).
Put another way, the art of having some structure while staying open to the unknown.
Let’s get to it.
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1. Become An Essentialist
You can do anything, just not everything.
This one was hard for me to accept (I still struggle).
But for every decision, there’s a tradeoff. If I split my attention between too many things, nothing grows.
Essentialism is the art of less, but better. Getting rid of the trivial many for the vital few.
This comes from the book Essentialism, by Greg McKeown (a good read, if you’re into reading).
To get better at planning in my own life, I first needed to focus. That meant putting some of my passions on the chopping block.
(or at least the back burner)
Knowing what’s most important to you and your vision right now is powerful stuff and helps narrow your focus.
2. Keep A Second Brain
Have you ever been lying in bed, waiting to fall asleep, when you suddenly have a great idea (or remember something you need to do the next day)?
It’s usually something simple that’ll be “easy” to remember. So you tell yourself “pfff, I’ll remember that.”
So you fall asleep.
Then you wake up completely blanking on what the hell that thing was you were supposed to remember.
So annoying lol.
Our minds are neat, but sometimes they need a hand. I like to get better at planning by simply jotting things down and planning my life or projects with a second brain.
I use my Notes app for quick stuff, Google calendar for important reminders, and Notion for the more serious life and project planning.
3. Break Down the Big Stuff
Great planning is strategic.
And one of the best ways to add a strategic element to your plans is to break them down into smaller steps.
This is an exercise in reverse engineering, whereby you take a bigger goal or project, and deconstruct it into its smaller component pieces. It looks like this:
Define your main goal
Break down your main goal into micro goals
Break down each micro goal into smaller nano goals
After you’ve broken down your bigger tasks into nano goals, just focus on the nano.
Understanding these smaller steps not only makes it easier to tackle bigger projects, but it makes completing them more realistic.
Because looking up at the peak of a big mountain is overwhelming. But taking things one step at a time isn’t.
4. Have Backup Plans
Things don’t always go exactly as expected. Planning ahead (expecting this) helps.
So when you’re forced to pivot, you’re ready to go with a plan B, C or more.
For example, let’s say I’m planning to take a weekend trip out of town. My original plan is to drive to the destination and stay at my favorite hotel.
But what if, on my way, I get a message from the hotel saying they’ve been forced to temporarily close due to a fire. What do I do then?
Or what if my car broke down the day before I was scheduled to leave?
In both of these situations, having a backup plan (for those random, rogue situations) would come in serious handy.
Of course, this also doesn’t mean I need to be paranoid and over-plan for every single thing in my life. But for the important stuff, it’s helpful.
It’s a ways to increase your control and build a more sustainable planning system.
5. Use Systems
No planning tip list would be complete without mentioning the importance of building a good, repeatable system.
A system is a workflow. It’s a personal step-by-step action plan for things in your life.
Having a series repeatable steps makes it easier to meet goals and complete tasks. A lot of the ideas in this post support a good system. So let’s bring it all together.
A good system includes:
Clear goals and objectives
Your weaknesses or bottlenecks
Workarounds and solutions to any weaknesses or bottlenecks
A way to track or manage your workflow
A schedule and process for working through your tasks
A way to review and reflect (adjusting things as needed)
6. Make Things Visual
I’m a bit of a visual learner. But creating diagrams, charts or mind maps makes planning easier to remember and manage.
You can use free mind map tools (like mind meister) or simple design software like Canva. You can also leverage AI to make things even easier. Just search for tools that suit your needs.
For example, you could feed ChatGPT your data and information (creating a custom GPT) and have it create a logical workflow for you based on your lifestyle and goals.
Whatever tool or strategy you use, making things visual makes planning easier.
7. Stay Open
If I’m ever too strict with my plans, I might miss better paths forward or opportunities that come up along the way.
There’s a time to double down and focus, but there’s also a time to pivot. Knowing when and how to choose is personal and a bit of an art.
I use intuition, body scanning and simply asking myself what I really want to do in life. Alignment is key.
And if I really don’t know, I choose the path that’s the most fun and I find myself getting lost in flow. Play is a powerful strategy for clarity and momentum.
Anyways, that’s all I’ve got for today. Happy planning.
Later ✌️
Want More? Nice. Here’s More.
Procrastination gets a bad rap.