How to Use a Day Plan Without Wanting to Stab Your Eyes Out

If you’re a creative type like me — or if you simply have a soul — at some point in your life the thought of day plans and organizers has made you want to hurt someone. (Unless you’re the natural organizational and planner geek, then kudos to you. You can skip this article). I know, because I’ve been there. Creating and following a day plan is something I still struggle with. In fact, that’s why I’m writing about a day plan right now. I can’t even begin to fathom trying to follow a weekly plan. I’m just not at that level yet.

Anyway, we’re here to figure out how to follow a plan without inducing violent thoughts and suicidal tendencies.

So the purpose of a day plan is to get more done, right? It’s supposed to help you get things done, while reducing the stress of procrastination. You know that. But you can’t get past the feeling that following a plan is putting a noose around your neck and suffocating your spontaneity.

We know the purpose of the day plan, but how do we get past all those negative associations and dissenting feelings? It took me a long time to realize that a plan isn’t necessarily set in stone. It’s not a rigid quota of tasks that I must do. If I don’t complete them all, I’m not a failure. It’s a guideline to aim for, not a dictating oppressor. Misunderstanding this caused a lot of initial resistance for me.

When I plan my day, I inevitably don’t complete everything I wanted to. I end up feeling like I failed and start resenting the plan again. It’s the plan’s fault, damnit! “#${54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} conformity, #${54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c}@ the plan!” I say.

Being the control freak I am, it’s hard for me to let go and realize that if I don’t finish everything, it’s okay. So I tell my planner I didn’t mean what I said and beg for forgiveness. It’s a love-hate relationship. I realize the point of planning is having more time to do the things you actually want to do. (This is the second biggest love-hate element of our relationship, I have a hard time harmonizing productivity and happiness.) So I schedule time for the little things I enjoy; like 30 minutes of blog reading I call “research.”

The problem is that I underestimate how much time it will take to get things done. I don’t take into account unavoidable interruptions and distractions. ADD is hard.

So what do I do when I end up spending more time than I anticipated on a particular project? Yeah, you guessed it. I take out my “fun time” and sacrifice it for the sake of productivity. What happens? I end up resenting my day plan even more. I curse her rigidness, but secretly worship her illustrious productivity allure. Damnit woman, why must you torture me like this!

As you can see, there are a few problems I and many other spontaneous-minded people face with trying to follow a plan. But does it have to be like this? Can’t we just work it out?

So here’s what I’ve learned. Hopefully this can help you follow a day plan without wanting to hurt someone:

1. It’s just a plan, seriously. Your plan isn’t meant to be an untouchable finality. It’s meant to help you, not control you. Realize that if you don’t finish everything on your list, it’s okay. It’s going to be all right. I promise.

2. Prioritize ruthlessly. While dreaming up your award winning plan — which will ensure your world domination — think about what’s really most important. If you could only accomplish 2 things today, what would they be? What about 1 thing? At the end of your day, what would make you the happiest knowing that you finished? Put that first in your day. Your day isn’t finished until you complete that 1 thing. Everything else is secondary and must be sacrificed at any cost.

3. Be realistic. I know you want to organize your entire stamp collection, clear out your inbox, and write your master thesis “How ergonomic staple removers will change your life”, but let’s be realistic. Rome wasn’t built in a day and your amazing new tape dispenser business won’t be either. The best way to ensure that you don’t end up hating your plan is to underestimate. If you think something will take an hour, give yourself an hour and a half. Remember, ADD is hard.

4. Don’t sacrifice your free-time. Don’t sacrifice that ten minutes you allotted to pick your nose and disengage from the cubicle machine. The purpose of your plan is to help you improve your life, not make it worse.

If you’re trying to liberate your life, you need a plan. But you don’t need to sacrifice your sanity. Remember: You work your plan, your plan doesn’t work you.

Jonathan is the author of Illuminated Mind – The less boring side of personal development. You can subscribe to his here, or get more from him on twitter.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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