Creative Wayfinding For Ambitious Optimists.

The Impossibility of Right Decisions

March, 18, 2023

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

There’s a maddening cycle that plays out every time I launch a new cohort of my course,  Podcast Marketing Academy.

I spend months planning the launch, tweaking the content, and making upgrades & improvements to the product as a whole, almost always requiring difficult decisions about what to prioritize in the limited time leading up to the launch.

Most of the components I’m looking to improve on have multiple potential solutions, any one of which might be the absolute best way to proceed.

And while it’s impossible to test all the options for every potential improvement to find that absolute best path forward, I do my best, using a mix of research, analysis, and intuition to make the right decisions about which projects to focus on and what approach to take.

Then, the launch rolls around.

Like clockwork, the moment it’s too late to change course is the moment I realize the choices I made were not, in fact, the ideal decisions.

In almost every case, there was another, better path forward that only becomes apparent when it’s too late to backtrack.

And yet, despite, seemingly failing to have ever made the best possible decision, the course and business as a whole continue to progress.

“Best” Decisions Are Hard to Come By

This streak of imperfect decision-making isn’t confined to my course, or business or creative work in general.

In fact, when I look back on my life as a whole, I can’t think of a single pivotal decision where I made the absolute best-possible decision.

This, despite countless hours spent researching, analyzing, journaling… and maybe most of all, agonizing over each and every one of those decisions, many of which felt like my entire future depended on me making the “right” choice in the moment.

Again, this isn’t to say those less-than-optimal decisions didn’t move me forward in generally the right direction. They simply weren’t the most efficient route.

At this point, I’m convinced it’s essentially impossible to make the “right” decision. Or at least the best possible decision in any given moment.

Every decision we’ll ever make is made with incomplete information.

The important decisions—the ones we agonize over—in particular. In fact, the lack of information is the entire reason we agonize over them.

It’s hard for me to imagine a scenario where, once a decision has been made and we’re able to measure and assess its effects, we couldn’t look back and piece together a more ideal course of action.

On the one hand, this prospect of being unlikely to ever make a single “best” decision for the rest of our lives is somewhat demoralizing.

On the other, however, it invites a sense of freedom and opportunity.

The Freedom of Imperfect Decision-Making

When we take the absolute best possible decision off the table as a goal, our options expand significantly.

Because while there can only be one best possible decision, there are perhaps infinite pretty good decisions that will move us closer to our goal.

Even decisions that—in the moment—result in what feels like a step backward often give us the perspective and clarity required to make more efficient, focused progress going forward.

What’s more, though it doesn’t often feel this way, the number of decisions that would genuinely result in the type of ruin we could never come back from is vanishingly small.

In practice, then, while it might be impossible to make the absolute best possible decision in any given scenario, it’s almost equally impossible to make a decision that doesn’t ultimately move us closer to our goal.

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This is a comforting thought.

And it simplifies our decision-making process significantly.

Rather than agonize for days, weeks, or months over a decision, we should strive simply to do the following:

  1. Identify the few potential scenarios that would lead to complete ruin. Pin them above your desk and avoid them at all costs.
  2. Make almost any other decision with the confidence that even if it isn’t the best possible decision, it will move us in the right direction regardless.

Rather than aiming for absolute efficiency and perfection, perhaps our goal should simply be to make pretty good decisions most of the time.

This is a pretty low bar to meet.

And while the best decision we can make in the moment is rarely the ideal decision overall, the ideal decision overall is rarely the best decision in the moment.

If we let them, decisions have a way of wedging themselves beneath our wheels and grinding our progress to a halt.

Better to make any decision that allows us to maintain our momentum rather than halting to wait for the perfect path forward to present itself.

Because it won’t. No matter how long we wait.

At least not until we’ve committed to another decision and it’s too late to reverse course, of course.

Life is a trickster that way.

All we can do then is shrug, wave as we go by, and enjoy the road we’ve chosen, knowing that in all likelihood we’ll end up at the same destination regardless.

C’est la vie.


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 wilderness between us and our unique creative potential?”

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.