Will Freedom from Deadlines in Early Retirement Be a Good Thing?

or Could a Procrastination-Free Life Be a Real Possibility?

As early retirement gets closer, something that we find ourselves getting especially impatient about is the arbitrary nature of deadlines. Of course this is something that we’ve always known and felt, but while in the past this was something we could accept and move on, now it’s something that frustrates us, especially because of the “when it rains, it pours” phenomenon, which mandates that work deadlines must all cluster together to create these overwhelming and undoable masses of tasks that have to be completed simultaneously and impossibly.

To make matters worth, we are both world class procrastinators. As Association for Psychological Science fellow Joseph Ferrari reminds us, “While everybody may procrastinate, not everyone is a procrastinator.” He found that 20 percent of people are true, chronic procrastinators, though I think we might even be in some elite subclass within that. And this quote from him shows that he gets us: “It really has nothing to do with time-management,” he says. “To tell the chronic procrastinator to just do it would be like saying to a clinically depressed person, cheer up.”

So here we are: riddled with deadlines but fundamentally incompatible with them, and unable to just do it. We deal with the deadlines, of course, mostly through the horrible help of what Wait But Why calls the panic monster. But we rarely feel good about what we produce with the panic monster in our faces.

It’s no wonder, then, that we find ourselves yearning — OFTEN — for the not-so-distant future date when all of those work deadlines will magically :::POOF::: away. But:

Will living a life free from deadlines really be a good thing? Let’s dive in.

Here’s the answer: Um, duh, yes, of course it will be an awesome thing, that’s why we’re aiming to retire early. What a stupid question. End of post.

Just kidding. But before we can answer the question, let’s look at the role procrastination plays in our lives and what that has to do with all of this:

Procrastination’s Power in Our Lives

Research on procrastination is all over the map, and it feels like a still-nascent field for psychology. Sort of like how dietary research tells us that fat is horrible for us and good for us, that cholesterol is killing us and is harmless, and that sugar is the real culprit but is probably also fine. Bottom line: researchers still haven’t quite cracked this nut. Some research suggests that procrastinators have higher rates of depression, anxiety and — most tellingly — impostor syndrome, that feeling that you’re not worthy of your success and that you don’t know what you’re doing. Other research, like some of the stuff in this TED Radio Hour, suggests that procrastination is linked to higher creativity and non-linear thinking (though whether that is causation or correlation is unclear).

Mr. ONL feels that impostor syndrome in a big way. I feel it a little bit, but mostly just feel a huge sense of overwhelm that occasionally flows over into helplessness when work moves too fast. We’d love to think that we’re both those mythical procrastinating creative, non-linear thinkers, but we’re often too stuck in the dark playground to experience the joy of the creativity when it shows its head. (Though other times, inspiration strikes before the instant gratification monkey can get in the way, and posts like this one just fall out of me. Or then there’s this post you’re reading, which I’m writing at 2 in the morning, maybe just minutes before you read it. Because I even procrastinated in writing my procrastination post.)

(By the way, the “panic monster,” “dark playground” and “instant gratification monkey” language is drawn directly from Wait But Why‘s fantastic post series on procrastination. A must read for anyone with the affliction. And if you think that me maintaining this blog regularly is proof that I’m not actually a procrastinator, gaze upon this perfect bit of wisdom from WBW’s Tim Urban on blog writing: “Writing regularly with an immediate audience is an example of a terrific match for a procrastinator’s personality, because it puts his Panic Monster in the optimal location—it aligns the Panic Monster with his most important endeavor.” But then, he adds, “I pulled a lifespan-reducing all-nighter to finish this post.” I know that feeling, pal.)

Procrastination and Deadlines

For years we beat ourselves up about being procrastinators, I read books about how to stop doing it and we each tried a million to do list strategies. Eventually, though, we both just kinda resigned ourselves to the fact that this is how our brains are wired, and there’s no changing them. So we started to connect a different set of dots instead of the cause and effect of our incompatibility with much of work:

In this new way of thinking, procrastination isn’t the problem. Deadlines are the problem, the more arbitrary the worse. If only we could escape deadlines, we’d be happy. (Because, you know, “If only we could get to X, then we’d be happy” is a totally non-magical way to think. *sarcasm) Even if we don’t try to link the end of deadlines with something as lofty as happiness, removing deadlines from our life would have to have a positive impact like this, right?

Aw nuts, still back at happiness. Well let’s just go with it then, and ask the tough question:

Will Fewer Deadlines Actually Lead to Happiness?

In The 7 Habits of Highly Successful People, Stephen Covey talks about something called the Eisenhower Matrix, because Dwight Eisenhower was apparently a great master of efficiency and prioritization:

Good old Ike would like us to focus on the top row tasks most of all, those that are important but not urgent, and those that are important and urgent. Those tasks that are not important are not worthy of our time.

Unfortunately, procrastinators tend to dwell in those bottom row tasks — those that are not important or urgent, and those that are urgent but not important. Sometimes the panic monster forces us to focus on the upper right tasks, those that are important and urgent, but we rarely get to the ones that are the most important of all: the important but not urgent tasks.

Things that fall in the important but not urgent category are: writing a book, taking on a new creative endeavor that our soul is yearning for, planning that big trip we’ve always wanted to take, or anything else that stirs up a lot of resistance. (The War of Art, the book the notion of “resistance” comes from, is another must read for any procrastinators who wish to create in spite of ourselves.)

All of the big plans we’re making for our early retirement hinge on being able to tackle some important but not urgent tasks, preferably quite a few of them — writing beyond this blog, planning big trips and climbing expeditions all over the world, discovering new avenues for creativity. None of those things have deadlines associated with them, and it would be all too easy to fritter away the months and years without ever getting around to them, just as I wrote my college thesis in a two-day stretch rather than pacing myself and doing it over the course of the year.

Rethinking Deadlines

We’ve mapped out our purpose and feel good that we know what will make us feel fulfilled after we’re no longer working:

Though it doesn’t rise to the level of deal-breaker, it’s hard to think that we’d feel fulfilled and like we’d spent our time in a worthwhile way if we didn’t end up doing any of these things in early retirement. We’ll always stay open to the possibility that life will take us in a direction we never could have imagined, and that we’ll do all kinds of other amazing stuff that was never on our radar before, but it’s hard to believe our situation would change so much that we’d completely change our purpose or what interests us.

Which means: If we actually want to check some of this stuff off our list, we have to make a plan for getting things done. Which means: Deadlines.

We’ve accepted that deadlines will always be a necessary evil in our lives. Though we want to create as much space as possible for unstructured exploration, we know that we need an impetus to do the important stuff, not just the instant gratification stuff.

What will change is who is setting the deadline and what it means.

We’re still hopeful that the end of our careers will also spell the end of the arbitrary, meaningless deadlines, as well as those imposed on us by others, all of which seem to coincide with one another. We can be smart about setting them, and make sure they don’t conflict with each other. And we can try to align them to dates that make sense for that goal, so that there’s some meaning behind it.

But if we want to live the purpose-driven life we envision for ourselves — or, frankly, just a life where we do more than the instant gratification thing each day — then we need to embrace some form of deadlines. Deadlines may not make us happy, but living a meaningful life sure does, and we now realize we can’t have one without the other.

What Do You Think?

Any other chronic procrastinators out there? (I’m guessing yes — reading blogs is an A+ way to procrastinate!) Anyone else thought about what place deadlines may or may not have in your post-work life? Will you struggle to check important things off your life list, or are you more naturally self-motivated? Let’s talk about all of it in the comments!