Creative Wayfinding For Ambitious Optimists.

Creative Tire Chocks: How to Identify & Remove the Tiny Obstacles Keeping You Majorly Stuck

January, 7, 2023

🧭 This blog post is adapted from my Creative Wayfinding Newsletter.

If you ever find yourself parking a trailer, tire chocks are an invaluable piece of equipment.

Tire chocks are essentially wedges, often concave and plastic (though 2×4 pieces of lumber are commonly used as well) that are placed behind or in front of the wheels of a vehicle to keep it from rolling.

When placed intentionally, these simple tools perform their job remarkably well.

Unfortunately, the same principles of leverage that allow tire chocks to keep everything from jumbo jets to 450 tonne mining trucks in place, also apply to our creative projects.

Only, we don’t often realize the chock is in place.

If you’ve ever found yourself inexplicably stalled on a project that you can’t seem to make progress on, chances are, there’s an unseen chock wedged in a key location.

And until you find it and remove it, chances are, you’re not going anywhere.

Overcoming a Year-Long Chock

Until recently, I had been stuck on a tire chock with one of my projects for more than a year.

The project is a quiz audit allowing podcast creators to answer a series of questions about their current approach to marketing and then receive a personalized grading and breakdown of each of the categories of marketing.

I was excited about the idea, knew it would be incredibly valuable for my audience of podcast creators, and recognized that it was going to be a central part of the  Podcast Marketing Academy  marketing strategy going forward.

Despite my excitement and the clear incentives, however, I found myself inexplicably stuck.

For a year.

Finally, a couple weeks ago, I forced myself to sit down and do a simple brain-dump a list of possible questions that might eventually make up the audit.

Almost like magic, as soon as I had written down the first few questions and their possible responses, the rest of questions followed.

From there, I signed up for the quiz software I’d been eyeing since I first had the idea for the audit, uploaded up the quiz and quickly set up the scoring system.

Then, I designed the landing page, wrote out all the copy and analysis on the results page, and scripted out the follow-up email course.

Within just a few days, the project I’d been stalled on for more than a year was nearly complete.

So what happened?

The (Unfortunate) Power of Leverage

At first glance, it seems silly that a simple low-stakes task like brain-dumping a list of potential questions might be the chock that holds up an entire project.

And yet, in my experience, almost all creative project chocks are equally small and seemingly simple.

Which is exactly why we overlook them.

The truth is, if placed in juuuuuust the right location, even a tiny chock can hold back the weight of a much larger object.

In fact, relatively small 100 lb chocks are routinely used to prevent the aforementioned 450 tonne (1,000,000 lb) mining trucks from rolling down hills.

Is it so surprising, then, that seemingly insignificant tasks routinely stall our creative projects?

The good news is that despite chocks being both plentiful and incredibly effective in their ability to prevent our progress, in the end, they’re fairly easy obstacles to overcome.

At least if we know where to look for them and how to remove them.

Three Types of Creative Chocks

A chock keeping a project in place can be almost anything. But in my experience, they most commonly fall into one of three categories.

  1. An external circumstance that needs to fall into place
  2. An action or task to complete
  3. A decision to be made

Let’s have a closer look at each type.

An External Circumstance That Needs To Fall Into Place

These chocks show up most regularly in projects involving other people.

In these cases, the chock is often a task or decision that someone other than us needs to make for the project to move forward.

Another type of chock in this category might be that the timing isn’t quite right for our project and we need to wait for the conditions to change for our project to be viable.

This category of chocks are particularly frustrating because, while we may be able to influence the situation, we don’t have direct control to remove the chock ourselves.

Fortunately, these types of external chocks are less common than the other two categories, over which we have full and direct control.

An Action or Task to Complete

Perhaps most commonly, the chock on a creative project is one, often simple task that holds the rest of the project up until it’s been completed.

This was the case in my own quiz audit project.

And as in my case, the reason we tend to avoid and procrastinate on these tasks is often not the work involved with the task itself, but an underlying lack of clarity.

That lack of clarity might be centered on whether this is, in fact, the right task to work on, whether it will achieve the desired result, how to approach the task in the first place, or any number of other doubts, big and small, rational and irrational.

The irony is that these tasks are often exceedingly small, taking no more than 15 or 30 minutes to knock out of the way, paving the way for the rest of the project to roll downhill and build momentum.

And yet, our desire for certainty before starting them often keeps us inert for weeks, months, or even years.

When encountering this type of chock, the most productive action we can take is to simply force ourselves to take the first step forward without perfect clarity.

Because more often than not, once we take that step, we realize we already have all the clarity we need.

A Decision to be Made

The final category of creative chock is a decision that must be made in order for a project to move forward.

This might be a decision about which software to use for a project, how to allocate tasks among your team, mapping out a schedule, or determining the priority of a given project in relation to other initiatives.

These chocks are perhaps the most insidious, because we’re often not aware of them.

These decisions can be large and important, but as with most chocks, are more often small and inconsequential, though often magnified in scope and significance in our minds.

To remove these chocks, I personally like to convert them into a task, getting them out of the vague recesses of my brain and into my task manager where I can schedule them to be addressed.

In most cases, when made plain and approached directly, a decision I’ve spent weeks mulling over can be made in a matter of minutes or even seconds.

Removing Creative Chocks & Building Momentum

For all the problems chocks make for us, they present an incredible opportunity.

Because once we train ourselves to spot and remove them, we quickly realize that most of the challenges keeping us from progress are not giant, immovable boulders blocking our path, but tiny pebbles to be nudged aside.

Once out of the way, we then build momentum, making it harder for future chocks to slow or stall us.

The first step when we’re stuck, then, is to identify the type and location of the chock.

Personally, I’ve created a field in my Notion project management system specifically to write down the current chock that’s holding each project up.

Because, if a project isn’t moving forward, it’s almost certainly because of a chock.

Clearly identifying the chock as specifically as possible reduces my frustration around projects I feel stuck on and gives me a clear map to getting them moving.

Once the chock has been identified and removed, the next step is to focus on building momentum.

Chocks are most easily placed when we’re standing still, such as at the start of a project or between distinct phases such as moving from building a product to marketing it.

But they also have a way of lodging themselves in front of the wheels of projects that aren’t getting our full time or attention.

To avoid this, it’s helpful to choose your timing to remove your current chock wisely, ensuring you have the bandwidth to continue rolling with the project once the impediment has been removed.

If you don’t, there’s a good chance the next task in line will quickly solidify into a new chock, stalling any potential to build momentum.

Of course, no matter how much momentum we build, various chocks will always find a way to stall and disrupt our work.

They call to mind Archimedes’ famous quote about leverage, which in this case, might be slightly rephrased as:

“Give me a wedge and a gap to place it, and I shall hold back the world.”

Learn, to spot and remove them, however, and the world is yours for the taking.


Explore how to navigate a creative life that matters

This article originally appeared in my weekly Creative Wayfinding Newsletter. Each issue is the product of a week of work, and contains something not available for sale.

A fresh perspective, a shot of encouragement when you need it most, and maybe even some genuine wisdom from time to time.

Each week, we explore a different facet of the question “How do we navigate the wilds of creating work that matters?”

It’s something I’m proud to create and I’d be honoured to share it with you.


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    Hi, I'm Jeremy, I'm glad you're here.

    No matter what you create, I'm guessing you spend a good amount of time feeling lost, hopeless, and unsure about how to get from where you are to where you want to be.

    So do I. And so does everyone doing creative work.

    This is the Creative Wilderness.

    Every week, I publish a new article in my Creative Wayfinding newsletter about how we as creators and marketers can navigate it with more clarity and confidence.

    If you're building something that matters, but aren't quite sure how to take the next step forward, I'd be honoured to have you join us.