Rear view of man in business suit with briefcase standing at a fork in the road.

“You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.” Tina Fey

The line between thoughtful consideration and overthinking is different for everyone, and just like the line between telling the whole truth and some version of the truth, very easy to see in other people. We’ve all had the experience of listening to a friend or loved one going back and forth on a decision for the umpteenth time and wanting to scream, “Just do something already!”

At the same time, sitting still and reflecting on something important often feels like a luxury. So many of us have a powerful story running in the background that says there already isn’t enough time for everything that has to be done—taking more time to think seems impossible. And yet, we know that one hour of planning eliminates 3-4 of redundancy or waiting for additional information.

So how do you know when you’ve given a decision enough consideration and are not overthinking it? Practice. And a timer.

Quantifying how long you want to budget for considering a decision is an easy way to get out of the math guessing game and into action. Working in increments of 15 minutes, set a timer and isolate yourself so you can focus on whatever you are trying to figure out. Don’t check your email or your phone. Don’t get up and make the bed or tidy up your kitchen counters. Sit still and concentrate. No doubt your mind will wander, that’s to be expected—what you’re trying to do is observe yourself making a decision while also being in the experience of making a decision.

If you do this a few times, you’ll start to get a good sense of how long you need when making various kinds of decisions. Decorating decisions take X amount. Where your kid goes to school takes Y amount. What you want your next job to look like takes Z amount.

Once you’re made up your mind, it’s time to go down the chute.

If you’ve ever gone ziplining or jumped out of an airplane or ridden a ride at an amusement park, you’ve had the experience of being launched into something. When it’s your turn, there is no time to overthink it—you’re strapped onto the cable, or pushed out of the plane, or locked into your seat and the motor starts. Instead of focusing on all the people growing impatient with your fear or inability to act, remember (or imagine) how it felt as soon as you let go. That’s freedom. That’s what is waiting for you at the top of the slide. The fear is temporary—liberation is forever.

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About The Author

Andrew Mellen's picture

Andrew Mellen is an organizational expert, public speaker, and the #1 best-selling author of Unstuff Your Life!

Andrew has helped tens of thousands of people worldwide to declutter and simplify their lives while regaining time for the things that matter.

A sought-after authority on organizing and productivity, Andrew's addressed audiences from The Great British Business Show to TEDx. 

Corporate clients include American Express, Genentech, NetApp, Time, Inc., and the US Depts. of Education and Homeland Security.

The media has dubbed Andrew “The Most Organized Man in America.” He writes a featured column called “Ask The Organizer” in Real Simple. In addition, he has written for and/or appeared in: The Wall Street Journal, Los Angeles Times, The New York Times, Oprah Magazine, America Now, The Lisa Oz Show, The Nate Berkus Show, Oprah & Friends, Martha Stewart Living Today, ABC, NBC, CBS, CW11, HGTV, DIY Network, LiveWell Network, KnowMoreTV, Better Homes & Gardens, Ladies' Home Journal, Woman's Day, Family Circle, USA Today, GQ, InStyle, All You, Tricycle: The Buddhist Review, Healthy UK, American Way, numerous trade and travel publications, and NPR.

He leads workshops and speaks internationally while maintaining a private practice working with clients ranging from Fortune 100 companies, trade associations, and non-profits to CEOs, award-winning filmmakers, and authors, as well as overwhelmed parents everywhere. 

In 2013, Andrew founded Unstuff U®, the world's first completely virtual personal organization training center, offering classes, workshops, and other online resources for businesses and individuals. 

Andrew is a member of the Experts Collective and serves on the faculty of the New York Open Center in New York City. He speaks frequently on the intersection of spirituality and organization at places including Omega Institute, San Francisco Zen Center, Tassajara, All Saints Church, JCC Manhattan, and the Center for Spiritual Enlightenment, among others.

Previously, Andrew was an award-winning playwright, actor, producer, and director and the former Artistic Director of Alice B. Theater (Seattle), DC Arts Center (Washington, DC), and Shuttle Theater Company (New York). He is a contributing author to Yes Is the Answer: (And Other Prog-Rock Tales).

Andrew lives by his motto: More Love, Less Stuff!® 

Find him on the web at andrewmellen.com.

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