The Un-Comfort Zone with Robert Wilson: Deadlines Work, MASSAGE MagazineAs I sit here writing this column against the deadline, I’m reminded of my days as a young advertising copywriter when I occasionally needed a deadline as motivation to finish a boring project. The deadline did more than motivate me to finish—more often than not, it was what finally stimulated enough creative thinking to move me forward. In other words, it motivated me to think outside of the box.

“Think outside of the box.” Boy, has that phrase become overused. People so often tell us we need to think outside of the box that it has fallen into the realm of cliche. Nevertheless, it is still true. Sometimes, however, we need to be put into a box first before we can think outside of it. A deadline is such a box.

I used to believe that the more freedom I had, the more creative I could be; but it doesn’t necessarily work that way. Ingenuity needs to be motivated by something, and if the desire to achieve isn’t there, then an uncomfortable boundary may work.

Have you ever watched a man or a woman with one leg run a marathon or compete in downhill snow skiing? I have, and every time I’m deeply impressed because I have both of my legs and I can’t do either one. I used to wonder why they were able to do so much more than me when I was the one born with the greater advantage.  Now I can see the difference is they were challenged by a boundary, and I wasn’t. Some of them might even argue they were the ones born with the greater advantage. Being unable to walk made them uncomfortable, and conquering their disability became a powerful motivating factor. They had to get out of that box!

Think of creativity as a prisoner trying to bust out of jail. When your resources and opportunities are limited, you must become innovative. A good illustration of this is the World War II movie The Great Escape. It is an amazing tale of ingenuity. Men with little to work with escape from a German POW (prisoner of war) camp. In addition to digging three tunnels without shovels, they made hand-drawn traveling documents and identification papers that looked authentic enough to pass for ones made on a printing press. Now that was a box to get out of!

I have enjoyed working for myself most of my adult life. People frequently tell me they wish they could be self-employed like I am. They say such things as, “If I could just get one client, then I could quit my job.”  My response is always the same, “Until you quit your job, you are never going to find that first client. There is nothing like the deadline of a rent or mortgage payment staring you down at the end of the month to motivate you to get out and look for clients.”

Everyone works under some kind of deadline. Deadlines force us to prioritize our responsibilities; they limit procrastination and they help us achieve our work-related goals. But we often lack deadlines in our private lives. We are not given deadlines to accomplish our most important personal goals, and without those boundaries, procrastination can creep in and destroy our best intentions. The trick is to impose a deadline upon yourself—but it has to have some teeth to work.
Here’s how to do it: Write down your goal. Then, set a reasonable date for which you can achieve it. Next, go to your bank or attorney and set up an escrow account. Now, add the teeth—put into the account an amount of money that will hurt to lose: $1,000; $10,000; $100,000; you decide. Set it up so that if you haven’t achieved your goal by the deadline, then the funds go to a favorite charity. Or, you can make it even more motivating: Let the funds go to your worst enemy!

If you’re not ready to try that, then try the buddy system. Pair up with a friend and each of you take responsibility to follow up on the other one. You can get together once a week and check on each other’s progress. If goals aren’t being met, then nag each other into the “Un-Comfort Zone!”

Robert Evans Wilson, The Un-Comfort Zone with Robert Wilson: Deadlines Work, MASSAGE MagazineRobert Evans Wilson, Jr. is a motivational speaker and humorist. He works with companies that want to be more competitive and with people who want to think like innovators. For more information on Wilson’s programs, please visit