Why planning might not be a good idea (How peering into the future quashed true love)


When I was a senior in high school my true love was a sophomore in college. That was back in the day when long distance calls were expensive, and we wrote piles of earnest letters full of angst and idealism.

One day I received a letter that signaled the beginning of the end of the relationship. That was the letter in which my boyfriend announced how many children we would have and what we should name our first son.*


In a flash, our love affair, which had up to that moment been overflowing with promise and possibility, gave me a feeling of impending doom. I could feel the walls close in.

You could even say it gave me the creeps.

And I wanted out.

Your business is like a love affair

If you love your work, your business is a sort of love affair. And the possibilities for your affair are always much, much greater than you can imagine. That’s because your personal imagination is necessarily constrained by your personal experience and knowledge.

But fortunately and marvelously there is a vast field of possibility beyond the limits of your personal imagination. That field of possibility emanates from the formless energy behind all things. Some call it Mind. Some Source. Some the Divine.

Whatever you call it, it’s bigger than you are. Way bigger.

And that’s a good thing.

Planning can foreclose possibility

When you plan too soon or too much, you foreclose that field of possibility. Not only does this severely limit your options, it can leave you feeling boxed in. Pushed around.

And quite naturally, you’ll want out.

Wanting out doesn’t mean you don’t want to be in business

Wanting out because you experience your business as confining and a source of pressure doesn’t necessarily mean you don’t want to be in business.

It could simply mean that you have a healthy aversion to living a smaller life than you were designed to live.

It could simply mean that your personal imagination isn’t offering you possibilities that light you up. Possibilities that engage and inspire you.

Possibilities that would make being in business a creative, stimulating, satisfying adventure.

Planning isn’t a bad thing

I’m not saying you shouldn’t plan. Planning has its place. It’s quite helpful when it comes to following through on an idea.

It’s great for managing how you’ll do things.

It’s terrible for revealing what things to do.

Planning is great for getting from point A to point B.

It’s terrible for deciding whether or not point B is a good place to go.

How to plan for a wide open future

The key to planning for a wide open future is to recognize that vast field of possibility and orient yourself around it. Here’s what that might look like.

Remember the vast field

Remember that there is a vast field of possibility far beyond what is available to your personal imagination. Relax and notice your connection with it. (This is one of those irritating things that requires not doing rather than doing. Sorry about that.)

Start with a blank slate

Step back from your good ideas. Give yourself some breathing room. Get curious.

Trust the value of glimmers and inklings

As your curiosity expands, you’ll catch glimmers of possibility. You’ll have inklings of what might be cool to do. These are important. Trust that they have value and don’t be in a hurry to nail them down.

Pay attention to what shows up

As you heed your glimmers and inklings, pay attention to what shows up. Have conversations. Ask questions. And stay with the attitude of curiosity rather than pushing for an answer.

Let yourself be guided by a nice feeling

When an emerging possibility is accompanied by a nice feeling, move toward it. Take the next natural step–the very next one–and let go of what steps 2 through 10 should be.

Let the future surprise you

My teenage love affair died because it shut off more possibilities that in opened up. That doesn’t have to happen to your business. Put possibilities before planning and get out of the way.

You may surprise yourself with how much you want to be in business.

* Don’t get me started on why he didn’t think of a name for our first daughter.

Main photo credit by Jer Kunz via Flickr

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8 Responses to Why planning might not be a good idea (How peering into the future quashed true love)

  1. I couldn’t agree more Molly. A couple years a go, I was working with a coach who was forcing me to plan out an entire year of sales and what would make up those sales. Although I’m naturally a planner, the amount of detail they wanted made me feel boxed in. As I tried to implement the plan, I found my creativity and excitement for my business shut down. The first quarter of the year was terrible personally and financially. I re-thought the plan. Re-set my goals. Loosened up the expectations and the rest of the year was fantastic.

    Thanks as always for the reminder, Molly!

    • Molly says:

      I hear you, Jen. Planning can be great, but as you say, it can box us in. When that happens, we shut down, which is a great way to get stuck!

  2. Wow-wow-wow-wow. Wow again. I am getting chills. This is SO perfect for me to hear today as year-end harvests of 2013 starts to turn to plantings for 2014. Yesterday, a “business does not compute for me” miasma overtook me for awhile. My creativity, connectivity, commitment, and love, all together in a sacred bundle (a “practice” or series of practices that some might look at as a biz)— considering this as a source of sustenance on all levels, and looking at it as “love affair” …… giving planning a place at the table without it owning the table…. This is a big opening for a massive shift for me. Thank you.

  3. Oh Molly. This thinking is as alien to me as going out to dinner without a penny in my pocket or showing up to a painting workshop with no paint. My mind has been infected and my life maimed by plan, plan, plan and follow the plan.

    I love this idea. I crave this freedom in my thinking and mindset. This sounds like so much more fun than the last year of my tiny little business. I always seem to be beating myself up because I’m not doing all the “marketing and business” things I need to do, or I must not be doing them right because I am not a famous, wealthy artist. Pooh, Pooh.

    Please expound on this subject. Please write more blogs on this mindset. This time of the year, the time of joy and family and celebration. Also the time for tallying up the only measure many people acquaint with success, $$$. My art success has many facets for me personally, which is probably just as well!

    Happy Holidays! Happy Life Everyday!

    • Molly says:

      Thank you, Linda. I look forward to writing more about this. I know from personal experience–with my own business and that of my clients–how the pressure to plan and get everything right can steal the joy from working for yourself. And when the joy goes away, why do it?

  4. I love this. “When an emerging possibility is accompanied by a nice feeling, move toward it. Take the next natural step–the very next one–and let go of what steps 2 through 10 should be.”


    • Molly says:

      Yes, Laureen. Letting go of steps 2-10 is so important. Otherwise planning keeps us from taking that critical first step.

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