Knowing what needs to be done is only part of the fuel that helps us move a project to finished. That doesn’t take into account all the underlying obstacles (many of our own making) that trip us up, and lead to procrastinating.
- You Don’t Have a Clear Reason or WHY
- Competing Priorities Pulling You in Multiple Directions
- Too Many Things on Your Action List
- Your End Goal Is Too Challenging… or Not Challenging Enough
- The Work Isn’t as Fun as the Eureka! Moment
- Project Cascades Keep Causing Displacement
- You’re Just Tired (But It Looks Like You’re Procrastinating)
- You Didn’t Leave Your Future Self Breadcrumbs
- Falling Down… On Celebrating Your Progress
- You’re Scared of Your Success
When a client comes to me about procrastination, or says “I know what I’m supposed to do, but I don’t do it,” I start by focusing on the issues or deeper reasons that lie beneath those behaviors. Many times after digging deep into what’s blocking the work, procrastinating turns out to no longer be a problem.
What I’ve witnessed again and again is we don’t need a ton of structure and motivation to do what it is we love. We don’t procrastinate on eating a bowl of ice cream. Given the chance, we will do it. (Read: A person who likes ice cream, and isn’t dairy intolerant.) Ice cream is a metaphorical placeholder for whatever activity you inherently enjoy.
If you’re struggling to get to finished, and it’s with something you enjoy, there has to be a source of friction somewhere. Here is a non-exhaustive list of frictions, or underlying reasons, that lead to procrastinating — each of which has its own solution built in. The overarching solution I’ve found (no matter which of the underlying reasons is at play) amounts to reacquainting people with what they truly value, and how to succeed by doing it.
Reason #1: You Don’t Have a Clear Reason or WHY
“Begin with the end in mind.” The sages all said it, but it doesn’t make it any easier. Given a big list of projects and tasks, it’s easy to lose context for why a given item is worthwhile. You might even know (in general) what needs to be done, but WHY it needs to get done, or how its completion stacks up with other action items, gets lost in the shuffle.
If ever you aren’t sure on the why, or the purpose, of your task, shift up to the next higher level of perspective, or unit of time. If you aren’t sure what needs to be done, shift down to a lower level of perspective, or a smaller time unit. Say that you’re looking at an item on your daily action list, and don’t know why it matters. Jump to the weekly or monthly perspective, and see how it fits.
You may need to make a couple of jumps. If you make those jumps and reach that larger, big-picture life perspective where your core values lie, and before-you-die goals, and still can’t see how an action item fits… it’s a candidate to drop. That’s right, drop completely.
There are certain things in life that need to get done, regardless of why. We also prioritize those accordingly. As an example, doing our taxes isn’t tied in an obvious way to a positive goal we have. But paying your dues to the government, and staying out of the red already has a pretty strong “why”.
If you’re dealing with tasks that have a clear-cut WHY, but you are still procrastinating, that’s when you need to refer to the other reasons and tactics listed here. Don’t give up yet.
Reason #2: Competing Priorities Pulling You in Multiple Directions
Even when you have an obvious “why” for everything on your list, you may actually find you still have competing tasks begging for your attention. This leaves you stuck in an unfortunate emotional tug-of-war, unable to invest your energy in any one project or task.
The most frustrating thing about this pulling in multiple directions dynamic is how silently exhausting it is. Ultimately not working because you’re too emotionally splintered is more exhausting than the energy output of doing any single item you have on your task list.
Our emotions play a massive role in our ability to finish projects. When people show me their action lists, each task is linked back to a feeling (or multiple feelings at once). Underlying emotions turn out to be either the fuel or the brakes, for higher-level cognitive activities. If your tasks are competing, it’s as much about the emotions attached to those tasks, as the nature of the tasks themselves.
Look at your inner landscape, not outside pull factors. What does each item bring up? Is it joy and confidence, or dread? Now a remedy. Choose the action item that matters most to you. To figure out which one that is, ask yourself:
- Which one task will advance the things that matter most to me?
- Which one of these tasks will I most regret NOT doing?
- Which one has a hard deadline that I must meet?
An additional insight: be mindful not to over-weigh items with hard deadlines since often that means you’re prioritizing OPP (Other People’s Priorities). We make other people’s deadlines “hard”, and leave our own projects in the “squishy” deadline camp. We hate letting other people down, so other people’s stuff regularly comes first.
If the questions above haven’t helped, I’ll parrot Anne Lamott: pick a bird. Do one thing on any single action item, for it’s better to make some progress on something than being stuck in the emotional tug-of-war of doing nothing.
Reason #3: Too Many Things on Your Action List
The previous reason (your competing priorities) is related to another major pitfall: having too many action items. If your planner or to-do list has too many individual tasks to do on a certain day or week, you’re set up to lose before you’ve even started.
Continuously extending our to-do lists (or in PF terms, our action item list) is a problem because our reach will always exceed our grasp. Our minds will keep saying, “You can do more.” When the mind starts storytelling — we could do it if we just moved this or that around — it’s not being kind or realistic to you. The majority of people find it difficult to do more than about five projects at any given point in time.
The Momentum app (set to launch this spring) allows for five or fewer action slots for exactly that reason. It’s a natural limit. The design is also meant to help with mindfulness about which five are going to get done. Think of it as rails to keep you from falling on the slippery stairs of shifting priorities, and creative projects.
Remember your action list is not the Epic List of Everything That Needs to Get Done. It’s a running dashboard of specific priorities you have decided you will attend to in a certain time frame. This week’s action list only spans projects to attend to this week; today’s action list only includes actions to attend to today. That means the thinking and deciding are done, so you can move on to the doing.
Still too many items? You likely haven’t done the decision-making requisite to make that list useful. It’s probably time for a cagematch to decide what matters most.
Reason #4: Your End Goal Is Too Challenging… or Not Challenging Enough
This is not the reason the project matters, it’s about the motivation to get it done. Motivation lives somewhere beyond the why connected to your personal vision of success.
Motivation also rests on what I call a ‘Goldilocks Principle’: work must hit a sweet spot between the obviously doable and the impossible. When there’s zero challenge to the task, you won’t be interested and won’t find your flow. If the challenge is too overwhelming, your head trash will work on you instead of you working toward a goal.
That sweet spot between difficulty and ease varies with the project and the person. I might struggle to finish a piece of writing, precisely because it’s a native or familiar topic. It may vary even in the same type of activity. Writing in general is easy for me. Writing about productivity is less so because I have higher standards for myself.
If you look at the end goal of completing an action and find that it’s either underwhelming or overwhelming, adjust the difficulty level appropriately. That is, decide what level of success you want, and what you feel comfortable imagining.
If you’re already using the SMART goals framework, you’ll be leaning heavily on the R for realistic. But what’s realistic is malleable based upon your priorities, effort, and the people you bring in to help achieve those goals.
Reason #5: The Work Isn’t as Fun as the Eureka! Moment
Ever feel incredibly fired up about a project only to find that when the moment arrives to start working on it, you’re no longer excited at all? This pattern is common and comes up often during the implementation phase of the creative process.
There’s a natural high to that “Eureka!” moment, but it’s followed by the more difficult part known as the work. Solving a plot gap in a narrative is a rush; reworking the entire novel, not as much. Identifying a bug in the code base is a rush; refactoring the entire code base isn’t.
We have a tendency to make our action list just after we’ve had the Eureka moment, and are riding that high. We’re not considering that down the line we may not have that juice, or remember we had it in the first place. When you’re struggling to do the work, the first thing to do is go back to the WHY (Reason #1). Knowing why you’re on a project in the first place helps you get through the trenches.
But it bears stating: sometimes projects relevant three months ago just aren’t anymore. That’s normal and natural. It may be that they’re less exciting than new projects you’re involved in. If you’re feeling unclear, it may be that your desires are at odds (see Reason #2). If you can’t find the WHY for that original project that stacks up favorably, remove the item from your action list for a while.
If and when it pops back up in the future, vet it against your current projects. Then you’ll know if it matters. If, after all that process, the project *still* keeps getting bumped, it probably doesn’t need to be done. Period. The fact you can do something doesn’t mean you should do it.
Reason #6: Project Cascades Keep Causing Displacement
As I’ve discussed elsewhere, a project cascade is when one project gets behind, causing another to slide, and another project falls behind as a result. It goes on like that until you’ve spent more time adjusting and managing the slippage than working on your projects.
This is the cause of much of the pressure that creates procrastinating behaviors. When projects are sliding, we end up with conflicting desires around our focus, and our action lists end up too full. Most of the time, we’re dealing with downstream consequences from prior choices, which we now have to deal with today. (“Downstream consequences” is so much more fun and easier to say than “second- and third-order effects,” but they’re functionally the same.)
Project cascades are based on a theory called Hofstadter’s Law: things take longer than we think (even when we account for Hofstadter’s Law). Since ‘Project A’ takes longer than we thought, and ‘Project A’ precedes ‘Project B’, ‘Project B’ has to slide. The reason for this is that in Project World, where most of us now live, we’re usually running multiple projects at once. When we cross a threshold for the number of projects we can run simultaneously, the net effect is sliding, cascading projects.
The snake pit herein is how easy it is to forget or discount that a sliding project displaces another project down the line since we can do only so much in any slice of time. Booting a project to next week is easy on paper, or on a screen, but in reality, this means displacement: whatever else we had planned for next week has to move or get triaged. Coupled with the psychological tendency for us to place a heavier weight on current pleasure or pain over our future pleasure or pain, this explains a lot about the feelings we catch when everything catches up with us.
Re-focusing on fewer important projects shouldn’t be underestimated. I’ve learned, and keep being forced to relearn, how precarious a too-full deck of projects really is… and how easy it is to miss small actions needed to keep all the bigger actions running. All it takes is a few days of missed actions to create a week of project delays… and then the sliding starts.
Having fewer projects allows you to focus on getting your highest priority projects done. A throughput of finished projects trumps a load of projects-in-progress any day.
Reason #7: You’re Just Tired (But It Looks Like Procrastination)
Procrastination might not come from the deeper-level reasons listed here, but instead from the simple fact, you may need some downtime.
Think about the ice cream metaphor, for what you enjoy doing the most. There comes a time when we’re tired even of ice cream if we are forced to eat it constantly — or there can also be times when we’re too tired from other aspects of our life to enjoy it. We’re all facing increased pressures in our day-to-day life due to the hyperfast world we’re living in, and technology continues to increase the demands on our time, energy, and attention. Technology has connected us with a 24/7 world of customers, collaborators, fans (potential or otherwise), and influencers, but that doesn’t make it easier to get important projects done — on the contrary, it makes it more difficult.
In the span of human development, this has happened overnight, which means the new requirements, expectations, and opportunities have been a net addition to our already over-full plates. While we’re figuring out how to make it all work, we’re working more. (Work isn’t necessarily a negative word around here; but it has to be balanced with other aspects of life, including recovery time.)
But the result of working more is that we’re just more tired. It’s a natural case of cause and effect. And because we’re so busy, it’s hard to find the time to treat our bodies as more than a head transportation vehicle, so our sleep, eating, and energy cycles are disrupted, too. It’s vital to realize that more quality downtime leads to more quality uptime. You deserve to give that to yourself. How else will you manage to do the best work you’re capable of accomplishing?
Reason #8: You Didn’t Leave Your Future Self Breadcrumbs
It’s all too common: you use all your available time to finish a work session as best you can, before sliding into something else, without a pause. But it’s that white-knuckled focus and slide pattern that makes getting started on the same project next time incredibly challenging. We assume we’ll be able to get back into the project before it goes cold on us, but life has an annoying habit of not following our plans. Anything can happen between the end of one focus block and the next, which gets you spun around, or lost in the woods. Through hard-won experience, I’ve boiled this down to two principles:
1) It’s simple to tell what the next step is at the end of a working session.
2) It’s incredibly hard to figure out those steps at the start of the following session.
When we’re doing our best work, it’s entrancing and easy to keep going; and that’s what makes the burn of losing track of where we were so rough. The colder the project trail is, the harder it is to get started again, making us avoid our best work entirely. ‘Leaving breadcrumbs’ amounts to making an easy path for yourself to get back there. Per the Grimms Brothers’ fairytale (in case it’s been a while since you’ve heard it) Hansel and Gretel leave a breadcrumb trail to avoid getting lost in the woods. (We can overlook their crumb trail being eaten by animals.)
If you decide to try this, it helps if you A) leave yourself enough time to leave breadcrumbs and B) out of kindness to your future self, recognize in advance that the momentum you have now likely won’t be there at the start of the next working session. Your breadcrumbs could look like any of the following examples:
- 2-3 sentences at the end of your current draft telling you where to pick up next time.
- Comment in a spreadsheet on what you need to do next, with a highlighted reminder to “START HERE”
- Notecard in a document or book you’re reading: just where you left off with a brief sentence on your thoughts from last time.
What you’re going for is a straightforward, consistent process that becomes second nature to you. My breadcrumbs tend to be hashtags directly in the document, like “#NextSession: Rework this to use a different metaphor.” I’ll often leave it with a question, since I’ll either resolve the question while I’m thinkwalking or, if the thought goes cold, it gives me a specific place to start next time.
As you ruminate over your work, you may have an insight, epiphany, or realization. The 5–10 minutes it takes to leave breadcrumbs is a gift your future self will appreciate. (See also the 10–15 split technique.)
Reason #9: Falling Down… On Celebrating Your Progress
Doing our best work requires mid- to long-term project timeframes that take place over several months or years. Completing one phase of a project also tends to kick off three or four more projects. Together these delays can create discouragement, even when you’re actually succeeding.
It’s difficult to see your progress when you’re in the trenches. But that’s precisely why celebrating your successes and recognizing your progress are some of the best things you could possibly do to motivate yourself to keep going. Not giving yourself credit or celebrating your efforts often enough, could explain a lot about why you’re finding it hard to keep going.
Focusing on all the things you could’ve done better steals the joy of your best work, and makes it a grind. If you haven’t celebrated yourself, when it’s time to dive into the next phase of a project, deep down, you might feel a sense of “why bother?”
That project only may be valuable in some distant future. It’s natural to de-prioritize the best work if whatever is in front of you… damn near anything… feels easier to get done, or will see results faster. That pile of emails may not be important, but it’s nice to see the transformation from not done to done.
Our motivation shifts if, and when, we allow ourselves to celebrate. Common practice is allowing ourselves to celebrate only at the end of a big project (assuming it’s successful, judged by other people’s standards). That amounts to a work/project celebration every year, or three. That’s a long time to grind.
Celebrating phases of projects involves thinking in phases from the beginning, by converting long stretches of work into shorter, more human time frames. A celebration offers cognitive tracking: it’s a reminder to take a pause, get your bearings, and start again with a more accurate plan. Even an online celebration helps keep your success pack abreast of your work, knowing that the pack is moving the ball forward. Let yourself feel and receive the acknowledgment of the hard work you’ve done.
On a final note, celebrating — regardless of the outcome — allows us to let the past be the past. Win, lose, or draw, it’s done. And you get to move on, better than before.
Reason #10: You’re Scared of Your Success
Without knowing it, people often become convinced that life is made up of no-win scenarios. These mental projections relate to any number of issues, but a central one a surprising amount of people tell themselves is that in order to be successful, we have to give up something important to us.
While we can’t go into all the specific no-win scenarios we convince ourselves of here, there are three general kinds that always seem to show up:
- Success will cause relational harm (with families, friends, and so on)
- The Success-vs-Virtue Myth
- The “What If I Can’t Do It Again” Trap
At play here is that we won’t allow ourselves to visualize the best-case scenario of what our life and work might be. Some refer to this as a negativity bias, but ultimately it’s a near-reactive flinch — away from what’s possible and towards what’s more comfortable, doable, and safer.
During the planning process, it comes up when we over-weight the failure we’re counterposing against the success we’re imagining. It comes up in the execution since we don’t play to win, trying instead to mitigate or prevent the failure we assume will come with winning.
Once you see the no-win scenario you’ve created or accepted, it’s simple to defang. (I’ve said it before, and I’ll say it again: simple does not equal easy.)
Mediocrity being the safe play is only partly true. It’s true in the short term and in the day-to-day decisions and compromises you have to make. But in the long run, it’s the worst thing for your thriving in life, business, or career. We don’t overcome no-win scenarios by choosing mediocrity; we overcome them by breaking the internal rules that create these scenarios.
Reason #11: What’s True for You?
Those are ten of the possible reasons keeping you stuck instead of finishing the best work you’re capable of doing. It’s not an exhaustive list; I can’t know your personal friction or blocking point. Only you can know your friction, and learn how to tame it. Use the reasons I listed here as some example tools to figure out your own unique host of challenges and solutions.
Which of the above reasons most resonate with you now? Which ones do you see as a recurring pattern for you? Did I miss something important?
And, more importantly, what will you do today and this week to address these root causes?
Hint: You probably can’t go wrong with prioritizing and scheduling some quality downtime.