Time Management and Procrastination: What Works

This post distills what has worked best for my clients who have a problem with time management and procrastination.

Sometimes, a person doesn't care enough to manage time well. S/he knows that a productive life is better led than a slothful one, but is impeded by depression. Or, having been beaten up in life’s first rounds, it’s hard to come out for the next round. Or his or her life is in such disarray that managing time better feels insignificant, like polishing the brass on the Titanic.

Of course, those are tough situations, but if that's where you are, your best shot is to defer thinking about time management and instead first take baby steps to improve your life, whether it's to take walks, see the dentist, clean a corner of one room, cut back even a bit on your substance abuse, get a job you can easily get even if it’s barista, or help someone worse off. That can boost your spirits, self-esteem, and gratitude.

The next step for such people and the starting place for everyone else is the following list of tips, presented in chronological order.

Your to-do list. Get in the habit of writing all your appointments in your phone or computer’s calendar or in a paper week-at-a-glance calendar. Keep your to-dos that don't have an appointed time on a memo cube on your desk or in your phone’s notepad. Check both often.

Curate potential tasks. Do you want to do the task? Some tasks are wisely procrastinated—Perhaps you actually would be more in the mood tomorrow. Or maybe you should delegate the task to someone else. Or maybe you needn’t do it all—You conclude that you have better things to do with your time.

Find the motivation, by picturing the benefits of doing it and liabilities of not? By proving that sonofabitch wrong? By giving yourself a reward, even for 10 minutes of work? Or just by imagining that you'll feel good checking off that item on your to-do list?

Choose your approach. Some tasks can only be done one way, but often, you have a choice of whether to choose a fun, easy, fast, or higher-quality approach. For example, how well researched does that report need to be? If you’re a people person, could you replace some of the spreadsheets with interviews? Would listening to music while you work be worth whatever distraction it causes? Do you need to just create a few talking points for that talk or is it worth the time to start by writing a script and then distilling it to an outline?

Should you start with the easy? Maybe that’ll get you going and once in motion, suddenly, you're tackling the hard part — or maybe not. But at least you’ll have gotten the easy part done, which is more than you did before.

Should you start with the hard? Mark Twain quipped that we should start each day by eating a live frog—That guarantees that the rest of your day will be easier. Okay, so maybe that's a bit much, but perhaps while you’re fresh, put in a few minutes on that toad of a task?

Should you end with the hard? Especially if you’re a night person, perhaps, like Emily Dickinson, you're more likely to get something done when everyone else is asleep, no distractions.

Beware excess rumination. If you stop ruminating before having made every effort at perfection, yes, you're more likely to fail. But ask yourself whether the benefits of replacing additional rumination with action outweigh the liabilities. Remember that doing the task creates the possibility that once you’re started, you’ll revise your plan, you'll succeed and so get praise, or at least not criticized.

And even if you fail, there may be a lesson(s) to be learned that can boost future chances of success. At minimum, you'll likely feel better about yourself for having tried and failed than if you sat on the sidelines, ruminating excessively, procrastinating excessively, choosing more pleasant but less helpful activities.

Write baby steps? If it’s a complex or long task, you may want to write the baby steps, the milestones that you can check off as they’re done. That feels good. If you don’t know a wise way to break down a task, is there someone you should ask?

The moment of truth. That’s when you’re deciding, consciously or not, whether to do the task or something more pleasant. That’s when you have to force yourself, yes force yourself, to do the first few-second part, then the second few-second part. An object in motion, well, you know.

The longer you procrastinate, the harder it is to start. Fear builds, for example, that the task is onerous so you wait 'til last-minute and the work is done rushed, poorly, your having suffered with guilt all the while. Force yourself to start now is key to getting things done well and with less pain. Worst case, it's done early, not hanging over your head, freeing you up for other tasks, and you and people will be impressed with you.

Take micro-breaks. A break’s length has a quick point of diminishing returns. Certainly, when stressed, it's worth taking a deep breath or three and a few-second stretch. So are few-minute breaks every hour. For most people, a break's cost-benefit starts to diminish after those few minutes.

The one-minute struggle. Getting started is usually the hardest part but the next hardest is when you reach a stumbling block. Try the one-minute struggle technique. Usually, if you haven’t made progress in a minute, additional struggle will only create bad memories of doing tasks, thus making you more likely to procrastinate in the future. So after a minute without progress, decide if another minute is worth it, whether to get help, whether you can do the project without conquering that roadblock, or whether you should go on with the project and later, with the benefit of having done more of it and with fresh eyes, take another crack at that problem.

Create time pressure. For example, if you'd like to break at noon, say “I’m going to enter all my 1099s before noon."

Some people need additional ideas to manage time and procrastination:

Pomodoro. This technique is named after the tomato-shaped kitchen timer but any timer will do, including the one in your phone. Set the timer for 25 minutes and get to work. When it chimes, take a five-minute break to do whatever you feel like. Repeat.

They say sitting is the new smoking. The Pomodoro technique helps you get out of your chair.

Punishment payment. You send (perhaps PayPal is easiest), $50 to a friend, instructing him or her to donate it to your least favorite political candidate if you don’t get the task done in time.

Peer pressure. Some people are motivated by daily or weekly check-ins with a friend, support group, or by posting progress on social media.

Ritualizing. Should you do some annoying but necessary recurring task before allowing yourself to eat dinner? Should you schedule exercise time daily with a partner? Should you block-off X hours on your weekly calendar for some project and treat it inviolably, as you would a doctor’s appointment?

Persistence is overrated. For example, if a job seeker has received 20 rejections and no responses, rather than doing the same thing and expecting a different result, recognize the wisdom in Emerson’s admonition that a foolish consistency is the hobgoblin of little minds and Kenny Rogers’ more folksy version: "You gotta know when to hold ‘em, know when to fold ‘em, and know when to walk away.” After some failures, the right question is, “Would my next set of efforts most likely yield results by persisting with the same goal and approach, making minor changes, or by pursuing a new direction?”

Bonus activities for more enduring change

Recognize that being productive is core to the life well-lived. This is an opinion that flies in the face of the work-life-balance exhorters but is perhaps my most deeply held belief. Even if your work is mundane, people live a better life if they’re highly productive during the standard workweek and beyond. I have much more respect for the person who spends hours 40 to 60+ doing their work well than someone who opts to spend those hours on sports, NetFlix, videogames, shopping, and chatting. If you can embrace that foundational principle, you will not even want to procrastinate. You will feel good about choosing work over play.

Address Peter Pan Syndrome. Some people just won’t grow up. And it’s understandable. Especially if you don’t feel great about yourself and your life, it can be tempting to bury thoughts of responsibility and just do the minimum to get by. Is that okay for now, or is it time for you to give yourself a wake-up call?

Identify and focus on your priorities. Many people claim that their time is swallowed by exigencies, that there’s too little time for discretionary priorities. Everyone has exigencies but, in discretionary time, good time managers ever ask themselves, “Is this central? What activity would better serve one of my core goals?” What’s your core goal or three, the things you care most about? Should you spend more of your discretionary time on one of those? For example, my deepest belief is that research toward an ethically available intelligence “pill” would do the most to enhance humankind. When possible, I spend my time and money in the service of that goal.

Just say no? “Nice” people say yes to requests they know they should decline. If even a good friend asks you to, for example, help him or her move and you feel there’s a wiser use of your time, see if you can muster the strength and wisdom to tactfully decline.

Address fear of failure? Psychotherapists often attribute their clients’ procrastination to fear of failure. At least with my clients, it’s more often caused by too often choosing fun over a task. But if you think fear of failure is operative, remember that successful people fail often but have gotten in the habit of quickly seeing if a lesson’s to be learned, then taking the next step forward.

Get better at estimating time. Many people underestimate the time a task will take. There's only one way a task can take the minimum time and countless ways it could take longer. That's why wise tradespeople appropriately add a perhaps 25 percent fudge factor to the time they think a project will take. If you tend to underestimate time, add 25%.

Log. Many people don’t realize where the time goes. Do you want to log your activities for at least one day? If so, set the your phone’s timer for 15 minutes. Each time it chimes, in a few words, in your phone’s notepad or paper memo pad, write how you spent the previous 15 minutes. The act of writing it will make you more conscious of how long 15 minutes is (Many people don’t have that important sense) as well as motivate you to be more productive. At the end of the day, review your log to see what you’d like to do the same or differently tomorrow.

Revisit your major time sucks. Do you want to try to telecommute at least part time? Spend less screen time? Chatting time? Getting high time? Shopping and chopping for unnecessarily time-consuming meals? Processing/ruminating and more time taking low-risk actions? Forgoing your second cousin twice-removed's third wedding in Winnetka?

Use the gas-pedal metaphor. We default to our natural speed, whether cautious or pedal-to-the-metal. Good time managers choose the speed appropriate to the task. For example, a hand surgeon sweats every detail to avoid cutting a nerve that could render a finger useless, yet when sewing up the patient, doesn't worry about whether the space between stitches is precisely even.

Telecommute. By design, the government is building fewer freeways, which lengthens driving commutes, yet mass-transit is usually more time-consuming still. Where I live (the San Francisco Bay Area), many people spend two or more hours every day in stressful, gas-wasting, polluting, commute traffic. Should you ask your boss if you might, if only on a trial basis, telecommute for part of the week?

Learn just-in-time. Courses, let alone degrees, are major time-sucks, and much of what is learned isn’t practically useful or is learned en masse so by the time you need it, you’ve forgotten it or it has become obsolete. Of course, credentials often help your career, but the price in time as well as money, is frequently not worth it, especially if you keep learning on a just-in-time basis: When you need to learn something, ask a co-worker, read an article, watch a video, attend a webinar, a day-long intensive, etc. If you need proof of your learning, log your learning activities and major learnings, and present those when requesting a salary review or in applying for a job.

Have a sponge activity at the ready. We all spend time waiting: in traffic, supermarket line, doctor’s office, etc. Your phone contains activities that can usefully sponge up your waiting time. For example, Google/Safari-search for a helpful article or video. Or read or listen to an audiobook. As I walk my doggie, I usually bring along a problem I need to think about.

Hire a personal assistant? Rich people know the benefit of a personal assistant: someone to do the $20/hour work so you’re freed to do the $100/hour work or to retain time: Even the rich know they’ll run out of time before running out of money. Many middle- and even perhaps working-class people might also be wise to hire a personal assistant, if only for a few hours a week, to handle errands, child pick-ups and drop-offs, domestic chores, waiting at home for the repair person, etc.

Take mini-vacations. The 8-day/7-night, let alone two-week-long vacation may be more for the travel packager’s benefit than yours. Preparing for a long vacation is time-consuming and stressful, and on return, you’re usually facing a stressful pile. Day trips and overnights tend to yield the optimal time-benefit—For most people, it’s wiser to have 14 of those during the year than two-week-long vacations.

Be Buddhist about it. Resist looking back to past failures and unfair treatment. Also resist looking ahead to that daunting mountain of tasks and worries ahead. Try to stay in the moment: doing what you need to be doing then, feeling good about each bit of progress.

Ask a friend. Sometimes, we just don’t know what we’re doing wrong. Do you have a friend who gets a lot done and might be willing to watch you for an hour or talk through your typical weekday and weekend to offer suggestions?

Forgive yourself. Failure is frequent and wallowing rarely helps. I know you’ve heard it before but it’s true: You’re human; you’ll screw up. Successful people fail but quickly see if there’s a lesson to be learned and then quickly rebound by taking the next baby step forward. Easier said than done, but it’s a worthy aspiration.

I hope there's at least a nugget of value here for you.

I read this aloud on YouTube.