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What to do if no time-management apps, plans or hacks ever seem to work for you

I can tell you, because I was you.

It always seemed so great at first. I’d get latest app, or buy the gorgeous new planner, or read up on David Allen’s Getting Things Done method for the millionth time. And for a while there would be hope. I would create my to-do lists. I would calendar my tasks in all their color-coded glory. I would vow to follow my calendar No Matter What. This time I really would change. This time would be different!

Spoiler alert: it was not different. By the second or third day — let’s be honest, it was never the third day — I’d have ceased to look at the calendar or planner or app, much less follow its instructions. If I chanced to glance at it before quickly averting my eyes in shame, it would seem like it belonged to someone else’s week, one only tangentially related to the one I was currently having.

Don’t get me wrong, I was still getting some things done, and I was still doing what I thought of as triage. I could sit down at my desk, look through my inbox and survey my mental list of projects and decide which fire was most important to put out first.

But I wanted more from of my time than this. I had longer-term projects I cared about that were moldering because I could never carve out enough space in a week for them. I constantly felt behind and like key things were in danger of falling through the cracks. Time management had to be the answer. So why did it never work for me?

Because, as it turned out, I didn’t have a time-management problem — I had a time-management fantasy problem. And if you were drawn to this article, you probably do too.


The Litany of the Undone

The time-management fantasy appears in different guises, but it can be boiled down to a single statement: once finally I get time management right, I will finally get everything done. It doesn’t sound that bad, does it? If you’re like me, it probably sounds borderline unquestionable. Isn’t that the whole point of learning to follow a schedule properly and productivity hacks and all the rest of it? To finally be able to stop accompanying your own life with a running monologue about everything you’re not getting done? Plus brains are very good at this carrot- on-a-stick version of motivation.

For a lot of us, this Litany of the Undone is the background soundtrack for our lives. We get out of bed telling ourselves we should have been up half an hour ago. We start work with the knowledge that we’re still not at Inbox Zero. After lunch, we notice that our back burner projects have been sitting so long that they are approaching room temperature. We finish work mentally reviewing everything that’s still on our to do list. After work, it turns out that we haven’t left enough time to work out before dinner, and the fridge is full of mushy vegetables we failed to eat before they went bad. We fall asleep noting that we really should have gone to bed earlier.

The most insidious thing about this Litany of the Undone is that it’s so constant we eventually cease to really notice that it’s happening — except for that low-level, persistent sense that we pretty much suck at everything.

No wonder we cling to the time-management fantasy like a life-raft. We want to escape the soul-sucking negativity of the Litany of the Undone. We want to find a way to finally do every task featured on it so we can finally stop feeling like shit about ourselves every fucking minute. Unfortunately, the fantasy only winds up making the Litany louder, longer and more insistent.


Time Management vs. Time Machine

To see why this is the case, let’s look at an example of the fantasy in operation. I recently coached a client who was having trouble keeping to schedules she made for herself for her work days. I suspected I knew the issue, so I asked her to write out her to-do list for any given day, and then write down how long she thought each thing would take. The idea wasn’t to schedule it out over a day, but to see how many hours we were talking total.

Because we met on a Friday, she chose a Saturday for this exercise. Before doing it, she had the idea that this would amount to about a half day’s work, allowing her to finish up by about 1 pm and still enjoy some of her Saturday. Nope. It turned out it would have required twelve straight hours of work, without time to shower or eat.

What’s so striking is that she was obviously aware of how long these things would actually take, or she wouldn’t have been able to do the exercise. But if she hadn’t done the exercise, she would still have scheduled out all the items on her list into time blocks short enough make them fit before1 pm, despite that not being nowhere near enough time to actually do any of the tasks.

For example, she would have put ‘Revise Bill’s marketing plan’ down for 9:00 to 9:15 even though on another level she knew perfectly well it would take at least 45 minutes. And then when it hit 9.15 and she wa

s nowhere near done with the revision, she’d have been upset at herself for failing to follow her schedule yet again.

So what gives? Why would a terrifically smart and highly successful woman wind up lying to herself on her own calendar about the time required to do things? Why was she assigning herself days that were literally impossible to complete?

Because this is what happens when we begin from the fantasy that time management will make it possible for us to finally do everything we’ve been telling ourselves we should do. We start by lining up the full Litany with our calendar and trying to put make everything fit. When it doesn’t all fit, we don’t take anything off the list. We can’t take anything off, because the whole point of this exercise for us is to finally be able to do everything and escape the Litany. To take something off the list would be to fail before we even begin.

Instead, we do the only thing it seems like we can do: we start to fudge the timing. We shrink the duration of various tasks despite being aware of how long things actually take. We decide we’ll forego lunch and breaks. We push our wake-up time back to 5 am. In the end, we’ve created a schedule that requires us to somehow squeeze fifteen hours work into every eight. And then we yell at ourselves when we abandon the schedule on day 2.

So, the first problem is: we don’t need time management to do everything the Litany tells us to do within the time we have available — we would need an actual time machine.

time machine pod

And the second problem is: we think time management is a time machine, because we think that if we just managed our time properly, everything on the Litany would fit in our schedule.

In the end, we decide we're just not capable of finding the time-machine on-switch that we assume everyone else has apparently located. This is the time-management fantasy in operation.


The holding pen

Before I describe how we get out of this fantasy, I think it’s important to pause a minute to take stock of how self-reinforcing it is. It’s more than just a catch-22. It’s like a perpetual motion machine that runs on and generates self-condemnation.

Here’s the cycle in a nutshell: the louder and longer the Litany of the Undone, the more desperate we are to do everything on it so we can get some relief. The more desperate we are, the more we invest in the fantasy that by scheduling properly we will finally be able to do everything on the list. The more we invest in that fantasy, the more likely we are to overload our calendars and to schedule tasks as if they take a lot less time than they actually do. The more overstuffed our schedules are, the more we would need an actual time machine to get through them successfully. And the more we believe in the time-management fantasy, the more we blame ourselves when yet again the time machine fails to switch on. We wind up with one more seeming failure to add to our list, and the cycle begins again.

In order to escape this cycle, we need to stop believing the underlying principle of the Litany of the Undone, which is that we are the problem with this whole set up. Our supposed failure is the unifying feature of every part of the cycle. Can’t get everything done? Guess you didn’t work hard and fast enough! Got to the limit of how much you can do in the hours you have? Guess you didn’t try using the time machine! Can’t figure out how to switch on the time machine? Guess you aren’t committed enough!

Believing that we’re the problem feels awful. But to leave this belief behind, we have to choose on purpose. And at first that may be almost as difficult as thinking we’re the problem. As long as we hold out the fantasy of completing the Litany of the Undone, we can tell ourselves we will be able to avoid the kind of choices that the finite nature of time makes inevitable.

By telling ourselves we could do everything if only we tried a little harder, we avoid having to accept that we’ve chosen work over exercise or cooking over meditation, for example. We don’t want to have to make those choices, so rather than acknowledging that we have, we pretend we’ve just gotten temporarily stalled on the way to accomplishing both things. Which also means that we don’t get to decide whether we really want to keep the choices we are making or whether we want to change them.

When we’re living inside the time-management fantasy, these kind of choices all seem provisional and temporary: pending revision when we finally get our shit together. The result is, the decisions we make about how we use our time become a kind of holding pen we put our lives in, a place we park ourselves until we can figure out how to be efficient and productive enough to do everything and never have to choose.

voluntary self-penning area

Leaving the holding pen means recognizing that we are already choosing what to do with our time and deciding whether we want to keep those choices. Perhaps more challenging: it means deliberately choosing to leave some things undone.


Choosing on purpose

This was the last hurdle Sylvia cleared as she left her time-management fantasy behind. We had laid out a plan for the week that involved addressing a long-term goal, and she seemed especially excited about having made a realistic estimate for meeting it, which involved working on it the first hour of every day while her email was off. She had decided to prioritize that long-term project for the now-reasonable amount of time she had allocated to complete it.

I had a suspicion there might still be a bit of a time-machine thinking at work for her, though, so I pointed out that, in order to stick with her choice, she wouldn’t be able to add that hour of email on to the end of her day. She’d have to finish out the day with an hour’s worth of unanswered email. And I saw her face fall a little bit. It seemed that, in the back of her mind, she still hadn’t really faced making a choice between the long-term project and the hour of email. She had just been mentally shuffling things around so that she would do one earlier in the day and the other later.

But postponing it wouldn’t negate the need to choose; it would just kick the can of choice further down the road. Rather than deciding between the long-term project and an hour of email, she’d wind up having to pick between dinner with her partner and hour of email. As we talked about it, she realized she’d unconsciously made exactly that kind of choice a hundred times evenings in the past, and it wasn’t one she wanted to keep making. She decided not every email had to be answered in the time frame to which she had been holding herself. And then she proceeded to storm through the long-term project that week while remaining well inside the scheduled work time she’d allotted.

This is the beauty of leaving behind the time-management fantasy. When we start from the reality that both time and our capacities are finite, we stop yelling at ourselves for not being able to do the impossible.

And over time, the Litany of the Undone fades, not because we’ve finally completed it but because we no longer believe that’s the goal.

We stop waiting for the time machine to power up, and we prune the list of things we have to do instead.

With this kind of concrete, do-able list in hand, it often turns out that some of the energy and commitment we’d been seeking from time-management in the first place suddenly becomes a lot more possible.

It’s a lot easier to kick ass at a task if you aren’t anticipating the Litany of the Undone to start back up as soon as you finish.

Perhaps more importantly, it’s incredible how alive we become when we let ourselves out of the holding pen—when we stop waiting to really live until we think we’re finally productive enough to deserve it.

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