When Planning Becomes Another Way of Not Starting

Oct 8

3 min read

A few years ago, I had a notebook filled with plans and ideas. Things I wanted to pursue. Changes I wanted to make. Goals I wanted to accomplish.

I had thought about them. I had written them down. For some, I had even spent time figuring out exactly how I could make them happen.

There was just one thing missing.

I wasn't actually doing them.

That made me think about a phrase we've all heard:

"If you fail to plan, you plan to fail."

There is definitely truth to it. Planning matters. It helps us organize our thoughts, anticipate challenges, and decide where we want to go.

But looking at that notebook made me realize something else.

Planning can feel a lot like progress.

Writing something down feels productive. Researching it feels productive. Creating a plan, making a spreadsheet, reading another article, or thinking through every possible scenario all feel like we are moving forward.

And sometimes we are.

But sometimes, planning can give us the feeling of progress without requiring us to actually make any.

A great plan sitting in a notebook doesn't change anything. An idea that stays in our head doesn't change anything. A goal written on a vision board doesn't change anything.

Eventually, something has to happen.

We have to act.

Which made me wonder whether another version of that familiar phrase might be useful:

If you fail to act, you act to fail.

Think about the things many of us have planned but haven't started. The book we wanted to write. The business idea we've been thinking about. The exercise routine we'll begin when life settles down. The career change we keep researching. The difficult conversation we know we need to have.

Why do some of these things stay in the planning stage for so long?

I've started to wonder whether sometimes it is because planning feels safer than action.

Planning doesn't require someone to say no. Planning doesn't reveal that our idea might not work. Planning doesn't force us to discover that we're not as prepared as we thought we were....Action does!

Once we act, we introduce uncertainty. We might make a mistake. We might fail. We might have to change direction.

And perhaps that is why another hour of planning can sometimes feel so much more comfortable than taking the first step.

The first action doesn't need to be big. It just needs to be real.

This is something I've had to remind myself of.

If you want to exercise but can't imagine finding an hour every day, maybe the first action is 10 minutes.

If you're thinking about changing careers but don't know exactly what you want to do, maybe it's one conversation with someone whose work interests you.

If you're considering starting a business, maybe you don't need a complete business plan yet. Maybe you need to test one assumption with one potential customer.

The first step doesn't have to solve the whole problem.

It just has to move you from thinking about something to doing something.

Sometimes clarity comes from action, not before it.

I think this is where I have gotten stuck before. I want enough information to feel confident that I'm making the right decision before I begin.

But sometimes that information simply isn't available until we start.

We act. We learn something. We adjust. Then we take another step.

This is something I see in coaching conversations too. We can spend a lot of time trying to think our way to certainty when what we may actually need is a small experiment that gives us new information.

Because there comes a point where more thinking stops helping us move forward and starts becoming another way of avoiding the uncertainty of beginning.

So now, when I catch myself thinking, "I need to plan this a little more," I'm trying to ask myself a different question: