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Are you should-ing all over yourself?

I had a period of my life where I lived out of my digital task manager. I had everything in there. Current goals, future plans, someday maybe things, as well as reminders of buying groceries, home routines, chores and next actions. The tool I used at the time was OmniFocus.

And it worked great. It’s super powerful and I turned into a power user, creating what OmniFocus calls Perspectives to slice and dice the views of my data to suit my contexts, regular reviews and everything in between.

But after a while I started to notice something. I developed a tendency to only enter the things I wanted to do later, as a reminder. But I didn’t enter the things I was going to do soonish. I kept them in my memory.

It was as if the things that were super important, I remembered anyway so I didn’t bother to write them down. And the things that I thought I should do were the things I entered into the task manager so I wouldn’t forget about them.

On the surface this looks like exactly what to-do-apps are for. Write down the things you need to remember. What can possibly be wrong with that?

A list full of should-do’s

Well what happened was that slowly and gradually, my task manager became full of bad conscience and guilt.

First of all, it looked like I got nothing done since the things I actually did were never entered into it. I very seldom checked off any tasks in the to-do app.

Second, notice the word “should” in the statement above.

My task manager became a graveyard full of should:s, ought to:s and when-I-have-time-for-it:s. Expectations of desired behaviour, dead ambitions and dreams that never got worked on.

This was horrible for my motivation, energy and even self-esteem.

Every week during my weekly review I was reminded of all the things I hadn’t accomplished yet. And there was no feedback about the things I actually had done, so the only feeling I was left with was that of having a mountain of stuff that never got done and a cloud of broken promises and bad conscience looming over me.

While the most obvious solution might look like cleaning out the to-do list and make a hard triage of what I actually wanted to keep in there, my solution looked a bit different.

Yes, I did perform a clean-up to make sure only relevant things were kept in there. I moved someday items, vague plans and ideas outside and reserved the to-do app for true commitments.

The other change I did was to really enter everything I was going to do into the task manager. It made quite an improvement as well. Because it feels good to check off a task.

By entering the stuff I knew I was going to do I made my work more visible. Instead of having my weekly review going through the exact same list of things-I-should-do-but-won’t-really, I now could see that I did do some progress this week.

But these things weren’t the game changer, something else was.

I changed the relationship I had with my task manager.

Turning into don’t-forget’s

Instead of seeing it full of things that I should do (making me feel bad about not doing them soon enough), I started to see it full of things that I didn’t want to forget.

The distinction is important.

Turning a should-do into a want-to-do makes a huge difference in the invisible load you are putting on your shoulders. Try changing every time you say “I should…” to “I want to…” and see for yourself.

This simple change will reveal the true source of motivation of a task, and sometimes even help you get motivated in the first place. Or show if you’re better off deleting the task altogether.

For illustration, take changing “I should wash up the dishes” to “I want to wash up the dishes”. It can reveal that you feel both

– “No, I actually don’t want to do the dishes right now”
– “But I do want the satisfaction of a clean kitchen”

You always have a choice, and all choices have a consequence. Using the word “should” hides the choices and the consequences from you, and tries to motivate you from the negative emotion of guilt.

Turning a should-do into a want-to-do also makes you think twice about what you enter into the task manager in the first place. Who says you “should” to this thing? Where does the motivation come from? Why do you want to do this?

Revealing the intrinsic motivations in this way often helps in overcoming the inertia of doing tasks that are unpleasant on the surface.

To do things that you for some reason dislike to do, but are key to achieving your desired outcome. Or showing you that no, in fact you do not desire this outcome enough to warrant the seeming discomfort of this particular task.

I have also begun to separate the feeling of being pushed to do something from feeling pulled to do something. I find feeling pushed to be more related to inner fears and wanting to conform to perceived outside expectations, while feeling pulled or called to do something usually comes from deeper inside.

Often the push is easier to adhere to because it’s very clear and well defined. It’s force is louder and stronger. The pull is softer and quieter and you need to actively seek it out and listen to it. But once you tap into it, the source of motivation is longer lasting and more satisfying because it’s closer to your core and who you truly are.

Changing the relationship to my task manager made all the difference in the world, because now I don’t see it full of things that have come from fear and judgement.

Instead it’s a place of choice which is so much more empowering.

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