How to start planning when you’d really rather not

What’s the plan?

Well, if you tend to get stuck acting like an Ad Libber, there isn’t one. That’s because, more often than not, things work out for you on the fly. You rely on luck, a quick mind, and the fearlessness to wing it. With minimal effort the world usually works in your favor.

Until it doesn’t. Until that luck you count on stops meaning off-the-cuff charmer and starts requiring a fully prepared person.

Yes, planning is hard. There’s a whole bunch of career disciplines devoted to it, for Pete’s sake. But, on occasion, even the most brilliant of us need to chart out a course before diving in.

Fortunately, not all planning requires spreadsheets and Roman numerals and gobs of research. When your back is against the wall, start by identifying your planning kryptonite — what is it that makes you so adverse to it?

It just so happens that Unstuck’s mini-quiz can help you do that. Then, the next time a plan is called for, you can use the exercises in our “Painless Planning” printable worksheet to move forward.

Ad Libber mini-quiz: Think of a time when your situation required some sort of plan but you didn’t have one, even though deep down you knew you probably should. Then quickly answer the following three questions:

How did you Feel when you didn’t have a plan?
A. Exasperated.
B. Unconcerned.
C. Guilty.

What did you Think when you didn’t have a plan?
A. If I could only…
B. It’ll get done, one way or another
C. I work best under pressure.

What did you Do when you didn’t have a plan?
A. Kept looking for solutions.
B. Hoped for the best anyway. Figured it would all work out in the end?
C. Put off thinking about it.

If you chose mostly A answers, read about Roundabout Libbers, below. Mostly Bs, you’re likely a Free-Spirit Libber. Cs are Last-Minute Libbers. If you had a mix of letters, you’re a hybrid, which means you’ll find parts of yourself in all three types.

A. When you act like a Roundabout Libber
You usually take the long way home — which makes yours such a great journey. You find insight and inspiration along the way that straightforward thinkers often miss. But when it comes to creating a plan of action, it feels like you have too much information. So you keep circling in a maze of ideas without a map to make them work.

You need a system that helps you act on your creativity. Call on your powers of invention to conjure a new form of planning, one that works like your mind does, not someone else’s. Instead of a beginning, middle, and end, consider multiple starting points for more flexibility. Each direction you try will push toward the center, where the solution is often found.

Try this micro-planning exercise.

B. When you act like a Free-Spirit Libber
Your easygoing nature keeps you open to life’s foibles. You take things as they come, and people love you for it. A strict timeline, however, hems you in. Gone is the surprise and spontaneity that makes life interesting. That’s when your congenial nature turns contrary as you try to find a way to avoid it.

You need to get comfortable with accountability so you feel less restricted. Believe it or not, there is joy to be found in planning. It provides a sense of purpose and an expectation for success. Planning lets you put both feet in so you try harder (and that builds trust). In the end, you’re free to enjoy the satisfaction of a job well done.

Try this accountability mind-shift exercise.

C. When you act like a Last-Minute Libber
You’re in good company — and lots of it. Without a plan in place, you can put off the inevitable until the pressure builds, which you rely on to get going. The nasty irony of procrastination is the inner nagging, which spoils the carefree time you’re longing for.

You need to discover the luxuries that come with starting earlier. Truth: When you cram things into not enough time, you usually encounter an unforeseen obstacle, putting you even further behind the eight ball. The best part about ample time is that you have more than one chance to get it right. You also get a good night’s sleep.

Try these tips to double-cross procrastination.

DOWNLOAD THE PRINTABLE WORKSHEET: Painless Planning: How to get from A to Z when making a plan just isn’t your thing

Stop Your Procrastination Tip CardsWhat’s stopping you now?
Attack your delay tactics in the moment with Unstuck’s Stop Your Procrastination Tip Cards, which address 10 of the most common excuses we tell ourselves.
Learn more>


More Unstuck Advice

Instant Insight: Stay true It's the easiest thing in the world to get swept away by the allure of a new fashion, new scene, or new crowd. It's also just as easy to feel the need...
How to protect your calm from secondhand anxiety It’s tiring to be around someone who complains, thrives on drama, or is always high-strung and rushing around. After spending time with this p...
Instant Insight: Help out whenever you can We tend to think of good deeds in important, but grandiose contexts — volunteering in soup kitchens, donating to charity, giving out kidneys. But to h...