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Learning to Manage Procrastination

8 tips presented in context.

Rachel Fisher, CC 2.0
Source: Rachel Fisher, CC 2.0

I’ve written previously on procrastination. The format was standard: a list of tips. But some people are helped more by a contextual example, so here is a composite story of a how a procrastinator got better:

“You see, Tom, I have end-stage cancer. They give me six months to live. I’m angry that no one has written my biography even though I’m one of the richest CEOs on Earth. I hear you’re the best biographer but slow. So here’s what I’m offering you: If, before I die, you can complete a fair-minded 200-page biography of me, I’ll give you $10 million, a drop in my bucket but an ocean for you. Deal? I’ll give you until tomorrow to decide."

Even though it was the deal of a lifetime, tomorrow passed and Tom didn’t respond. He wrapped himself in a strait-jacket of yes-but, fear-of-failure rumination: “I take years, not months. The book will be crap. What if he hates it? What if I hate him?” Beyond Tom's specific concerns, he tended to escape the uncomfortable even if it would yield long-term gain.

Tom was viewing his glass as half-empty. Viewed half-full, he would have seen the project as a challenge: to write something good in six months: Many authors do, so why couldn’t he? And he could reduce the risk of the CEO hating the manuscript by showing him a chapter at a time and, where possible, accommodating the CEO’s feedback. And regarding Tom hating the CEO, that’s something he'd likely discover in the first day of interviewing him—a small investment given the $10 million dangle. His friend said, “Damn it. Be uncomfortable for a while if that’s what it takes.”

Those arguments and the guilt-trip pushed Tom enough that, three days later, he phoned. But the CEO said, “Sorry. I said, 'By tomorrow,' not three days. I have someone else now.” And he hung up. But sometimes it’s better to be lucky than good, so a week later, Tom got a call from the CEO: “I hated the guy I hired. He was getting the facts right but had no nuance, no humanity. You want to try it?”

Tom said, “Okay, let’s start next week. The CEO yelled, “A week?! A week for me is a hunk of my life. Your butt will start interviewing me right this minute.” Cowed, embarrassed, Tom said, “Give me a half hour to think.” “Fine.”

During the half-hour, Tom sat paralyzed, “How should I structure my interviews?" He struggled and struggled, weighing option after option and couldn’t decide. After 35 minutes, to avoid risking getting fired before he even started, he called with no idea of what he’d say. He simply blurted the first thing that came to his mind, “Tell me your first memory.” Jumping in with a one-second task is often key to breaking inertia; objects in motion tend to stay in motion.

The CEO was eager to work on his biography all day while Tom made every excuse for keeping it to two hours a day. The CEO tried bribing. Nope. The CEO tried threats. Nope. What finally worked was The Pomodoro Technique: They’d work for 20 minutes, then take 5 minutes off, work 20 more then 5 off, work 20 more and 10 off. That hour of work would constitute a “pomodoro.” “Tom, you will do six of those a day.” They settled on five.

And all was proceeding apace until Tom asked, “What was your greatest ethical lapse?” The CEO said, “I don’t want to lie and I don’t want to tell you.” Tom then spent the next 15 minutes trying to cajole him, after which Tom thundered, “The hell with you!” The CEO chided, “You can’t make me tell everything, Tom. We’ve wasted a lot of time and stress on something that ain’t going to get solved. From now on, when we reach a roadblock, we will struggle for just one minute and if we can’t make progress, we just skip it and move on.” Tom acceded.

As Tom’s friend suggested, after he had drafted the first chapter, he showed it to the CEO, who, except for a couple small requests, liked it: “Onward and upward!”

And so they completed the book in five months, with the CEO still compos mentis. But on reading the full manuscript, the CEO said, “You know, I just don’t like it. The whole thing makes me look shallower and more evil than I am. I’ll give you a $10,000 kill fee but this is not going to work.” In response, Tom violated the “one-minute struggle” rule big-time, arguing, arguing, and even had a lawyer write a threatening letter, although the lawyer said Tom was unlikely to win the case even if had as much money as the CEO to spend on top-of-the-line lawyers.

So Tom got a literary agent who tried to sell the book to a publisher, but no one bit. The consensus response: “CEO is just another fat cat with a not-particularly-interesting story or set of tips.”

So Tom self-published it on Amazon's KindleDirect, and ended up selling fewer than 100 copies, mostly to the CEO’s close associates and family members. But he felt he learned a lot from the project about how to manage his procrastination:

  • Success usually requires accepting short-term uncomfortability for long-term gain.
  • Try to see project problems as glasses half-full: How could you address that problem? Could you live with a negative outcome?
  • If you don’t have a deadline, give yourself one, even if it means writing a check to your least favorite political party, which you give to a friend to mail if you don’t complete the promised work by the agreed-on deadline.
  • Start now.
  • Break your stasis by starting with a one-second task and don’t overthink what that should be. (Recall how Tom began interviewing the CEO for the book.)
  • The Pomodoro Technique breaks a big project into manageable chunks.
  • When you reach a roadblock, struggle for just a minute. Then decide if additional struggle is worth it or whether to get help. That diminishes the amount of pain in a project, thereby reducing the tendency to procrastinate.
  • Sometimes you can do you best and still not succeed. Easier said than done but ask yourself if there's a way to salvage something from a failure.

I read this aloud on YouTube.

This is part of a series. The others are on Time Management, Finding Mr or Ms Right, and Refreshing a Stale Relationship and Managing Your Money.