No need for an introduction, here they are.
1. You don’t make plans
This is a no brainer. If you forget to plan, you plan to forget. Without planning, your mind, and therefore your life, is unordered and chaotic.
2. Your plans are not yours
Your plans will suck if they are just the lists of things that other people want you to do: your boss, your wife, your kids, your parents, your friends.
Just looking at your plans will fill you with resentment, or wistful longing for the dreams you gave up.
3. Your plans are too detailed
Most people don’t have the problem of making plans that are too detailed. But some do. Those that do are usually facing the same problem as those who don’t plan.
They’re avoiding the real work.
Planning should never be a way to escape the real work. It should not take more than ten minutes each day.
Making overly detailed plans also limits your spontaneity and creativity as the day goes by. Spending too much effort planning makes you attached to your plans so strongly that it’s harder to change them when you really should.
It’s the opposite problem as that of not planning. Where the unplanned life is too chaotic, the overly planned life is too rigid.
4. Not focused on next steps
This is a clearer way of saying your plans are too vague. Vague plans, in and of themselves, are not good or bad.
Maybe your plan is to tackle something that you’re unsure of. Your plans will necessarily be somewhat vague.
Maybe you are planning to have some freedom and openness to your day.
So rather than saying vague plans are bad, because they aren’t, let’s instead say that plans should be focused on next steps. If you have a project to tackle and don’t really know how it’s going to go, then the thing you plan is to brainstorm, or do research, or flesh out what needs to happen.
By focusing on next steps, you can make concrete progress towards your goals, even if you’re not sure what the path forward looks like.
There is another way to avoid focusing on next steps, and that is to focus on where you want to be in a month, or six months, or three years.
That’s wishful thinking, not planning.
Good planning starts with a long term vision, and then you figure out what your next step is. Spending a lot of time on short term goals or intermediate planning is a fool’s errand. As soon as the rubber meets the road, as soon as you do your next step, those intermediate plans will change. So just skip that step entirely.
5. You’re worried about priority
Worrying about priority is another type of masturbatory planning. Spending time marking tasks with high priority won’t magically make you overcome your avoidance or resistance in the moment. Priority is something you know already.
Every time you think through what you need to do you know what is most important.
And you still don’t do it.
Spending more time marking tasks with high priority, or tagging them, or labeling them, or color coding them – all of that is just avoiding doing the real work.
So keep it simple. And do the work.
6. You use three (or five, or seven) different tools
Splitting up your plans across multiple todo lists, a calendar or two, a separate task list for work, and then trying to do this all across multiple tools will only cause problems.
It’s more things to look at, more stuff to manage, more lists to forget, more ways to screw up.
But it’s also more features to learn, different ways of tracking work, adding work, etc.
Keep it simple, stupid!
Keep it stupid simple!
7. You have no rigorous system
Tools + Habits = System.
If you don’t have habits, you don’t have a system. Period.
If you don’t have a single place to put the idea that pops into your head, you don’t have a rigorous system.
8. Your system requires inhumane behaviors
You may have read the words “rigorous system” above and immediately thought that it would be inhumane. By that I mean, something that isn’t human, that isn’t designed for humans, built around human strengths and weaknesses.
But your system can be rigorous and humane at the same time. It can be simple, straightforward, and also natural and normal.
When you don’t plan at all, you’re using a system that requires inhumane behaviors – most obviously, remembering all of the things you need to do in modern life. It’s not something our brains were built for.
Alternatively, having a detailed plan that you need to check back in with every hour is also inhumane. It’s not natural to be ordered around constantly, even if it’s your past self dictating to your future self.
9. Your system isn’t ritualized
One way to make your system humane is to include rituals. Whether you call them rituals or habits doesn’t really matter.
Humans are built to enjoy the rituals, and rituals can put our minds and bodies into the right mode to get work done, or to envision the future, or to completely zone out.
Rituals are also self-perpetuating. Once you’ve developed the habit, you get stuck in a rut. But it’s a good one. And if you aren’t able to go through your ritual, then you get a little anxious, which is also good. Assuming your system is simple and humane.
10. You don’t trust your tool(s)
If you don’t trust your tools, your brain won’t let go of the things you add to them.
But if you trust that once you’ve added tasks or appointments that your tools will keep them and you’ll be reminded of those tasks and appointments at the right time, then you’ll be at peace. You can add reminders and know they’ll be there when you need them.
Having too many tools is a great way to lose trust in your tools, because there are more points of failure and more points
11. You don’t trust yourself
It’s more common to distrust yourself than your tool. The habit of using your tools effectively is much harder to acquire than the tool itself.
So if you don’t trust yourself to check it when you need to, then your brain will try to hold on to things but forget and fail because it’s inhumane.
12. You try to do too much
Once you have some successes with planning you’ll fall into the trap of planning too much.
It’s ok. It happens to everyone.
As long as you self correct, it won’t cause long term problems.
13. You have no way to learn from your mistakes
Without regular reflection and adjustment, you won’t improve.
A key part of an effective planning system is a time to take stock and make changes. Often they’ll be minor, like tackling less after realizing you’ve got too much on your plate.
Sometimes they’ll be major, like adding a new daily habit (this is harder to do than to say), or taking on a new job.
Before you can learn from your mistakes you have to identify them, and without a time and a place to do that, you have no hope.
Many religions have rituals designed to help you reflect on your life and work to make changes.
But whether you’re religious or not, you need a time to do that, and making it ritualized, like other habits in your planning system, will make it more meaningful and effective.
Now What?
So, there you have it – all the reasons your plans suck.
If you didn’t pick up two or three ideas to improve your process, your tools, or your habits, you didn’t read carefully enough.
Go back and try again.
Pick one thing to change, and do it for a week.
Let me know how it goes.