During the month of July, we publish “best of” content. The following article was first published on June 29, 2011.

Dear Crucial Skills,

I tend to procrastinate overwhelming work projects until the last minute and know this bad habit is keeping me from advancing in my career. I feel like I’ve tried everything, but nothing has helped. I don’t know how to change. Can you help me?

Habitual Procrastinator

Dear Procrastinator,

Funny you should ask. I’ve managed to put off writing my response to you for three weeks now! But I’m flying home from Chicago and our editor, Angela, is firmly but politely requesting I get off my rear—so here goes.

We recently found that procrastination is a pretty pervasive problem. In fact, it is one of the top three Career-Limiting Habits we identified in a recent study. For some, these habits have cost them pay or promotions. But even those who can’t count an absolute cost of the habit acknowledge they could have achieved significantly more in their career if it hadn’t been for this chronic weakness.

I fall into the category of people who can point to specific losses caused by procrastination. At age seventeen, a partner and I wrote one of the first accounting applications for the newly emerging microcomputer industry. It was an instant success with our immediate clients, and I knew that if I would invest time standardizing the software and creating high-quality documentation for it, we could make millions. I didn’t. And within a year, a competitor went to market in that uncontested space and cashed in. Live and learn, eh?

But the good news is I’ve discovered a few simple sources of influence that have a remarkable effect on my energy, focus, and productivity in these crucial moments. I also got an enormous number of responses on our Crucial Skills blog and on Facebook from clever readers who have found their own ways to kick this habit.

Without further delay, here are some ideas:

Make It Motivating

• Make it a game. Even noxious tasks become engaging when we give them the characteristics of a game: focus, time limit, and a scoreboard. When I sit down to work, I make my scoreboard. I write down the number of things I want to get done before I relax. I limit my list to the number of things I can reasonably accomplish. It’s remarkable how motivating it is to check things off my list. Several readers actually use a timer. I think that’s a great idea to increase the “game” sense of focus, and to link the experience to a promise of reward.
• Repeat motivating statements. A couple of readers keep motivating statements at hand that help them reframe the decision they’re making in their crucial moment. Suzy said, “My favorite procrastination advice is, ‘If you have to eat a frog today, do it first. If you have to eat three frogs today, eat the biggest one first.'” Donald added, “I put this note on my PC: ‘Production Before Perfection’ to remind myself to create something even if it is imperfect and then focus on perfection.”

Build Skills

• Read a book. Lots of people have found useful tools in books that help them increase and focus their mental energy more effectively. Some favorites were The NOW Habit by Neil Fiore, The Procrastination Equation by Piers Steel, and Getting Things Done by David Allen.
• Treat productivity like a skill. Pick a small amount of time to focus your attention, then stop. Brett said, “Here’s a mantra I’ve found very effective at battling my own tendency to procrastinate. It’s four simple words: Make progress every day. Once I get started on something, even if it’s with the mental goal of saying ‘I’m only going to do this one thing for fifteen minutes’, it often leads to more. When it doesn’t, at least I have the satisfaction that I did indeed make some progress that day.”

Get Support

• Find a friend. Barb shared an experience where she learned from a friend: “You can learn to overcome [procrastination] by pairing with someone who has a different style. My boss, the ultimate procrastinator, and I worked together for many years. We made a great team. Instead of being a thorn in one another’s side, we used one another as a means of support and a sense of balance in how we approached our work. He knew he could count on me to develop a quick plan and start executing. I learned there are advantages to letting some things percolate so you don’t have to retrace old ground as projects often get redirected midstream.”
• Set boundaries with others. One reader recommended setting aside time to deal with problems: “A large part of managing yourself is managing who is allowed to interrupt you and when. One of the techniques I now employ is a ‘problem hour.’ As e-mails, phone calls, or other issues interrupt me, I push them to my problem hour. If the issues arise after my problem hour, it’s assigned to the next day’s problem hour.”

Reward Yourself

• Plan fun. Cecelia uses rewards to motivate herself: “My two favorite ways to deal with procrastination balance short- and long-term rewards. Sometimes going to my home office to work feels like being sent to my room. To change that mindset, I focus on how much better life is going to be once the task I’d rather avoid is over.”
• Pick a treat. Erin rewards herself by taking a break: “Dedicate an hour to a difficult task and then reward yourself by going to get a Starbucks coffee, or by having a chat with a coworker as a break.”

Structure for Success
Lots of readers used structural tricks to help make productivity easier. In fact, you’ll recognize lots of structural ideas even in the other sources of influence I listed above. Here are some favorites:

• Break it down. Divide big things into manageable amounts, then decide what manageable part you will accomplish next. Jim shares this story: “My mother died eight years ago and I received forty boxes of stuff to sort through. Three months ago, I started filing or discarding one box a week.” Thinking about one box is motivating. Forty is overwhelming.
• Leave some fun for next time. One trick I use with writing tasks is to never stop until I am on a roll. I make sure that, when I pause my writing, I know what I want to write next—so getting restarted will be easier. If, on the other hand, I finish a complete idea, I’ll have to start next time with the painful experience of figuring out what is next. Pause your work at a place that makes restarting feel motivating.
• Make an appointment with yourself. Erin also recommends you “Schedule slots of time into your schedule similar to a meeting time. Then make sure that time is dedicated only to the task. Schedule the most unwanted tasks first thing. By the afternoon, you are out of energy and more likely to procrastinate.”
• Build fences. Create an environment where you won’t be distracted. For example, turn off e-mail notifications, put your phone where you can’t see or hear it, close your door, and put in earphones. Some people even use software that shuts down internet access to help reduce wandering impulses.

Don’t overwhelm yourself by trying to do everything on this list at once—just pick an idea or two, experiment with it, and act like a scientist examining your own behavior as you see what makes you feel more motivated and productive.

It’s worked miracles for me. I never made millions on microcomputer software—but I finished this column!

Thank you to everyone who shared suggestions. If you have any other ideas you’d like to share, please post them on the blog.

Best wishes,
Joseph